Winding Cypress

Updated September 2026 · Jesse McGreevy and Marc Comisar, Domain Realty

McGreevy and Comisar are the team Winding Cypress sellers call first, and the team buyers call when they want the recorded documents read to them plainly. Jesse McGreevy and Marc Comisar lead Domain Realty Group, the #1 Team in Southwest Florida since 2012, and are Top 1% Real Estate Agents Nationally Since 2008, with over $900 million in personal sales between them. Winding Cypress is a gated, master-planned community in Naples, Florida. It sits north-east of US 41 (Tamiami Trail East) and east of Collier Boulevard (County Road 951) in unincorporated Collier County, ZIP 34114, and DiVosta Homes, a PulteGroup brand, built all 766 of its homes between 2015 and 2023.

The 766 homes come in three builder product lines: 152 attached villas in the Villa Series, 406 detached homes on 50-foot homesites in the Classic Series, and 208 detached homes on 65-foot homesites in the Estate Series, per the unit census in the Winding Cypress Community Development District’s fiscal 2026/27 final budget. They sit inside about 1,176 acres across five recorded plats, of which about 818 acres are recorded preserve tracts, per Collier County’s parcel layer. The Picayune Strand State Forest boundary is about 140 meters, under a tenth of a mile, from 7478 Winding Cypress Drive on the state’s conservation lands layer.

Winding Cypress has one homeowners association, one community development district and one clubhouse for every home. Its amenities are bundled into the association’s assessment, so there is no club to join and no equity membership, and the 2026 approved budget posts the full annual total for each series: $7,067.22 for an Estate home, $6,657.76 for a Classic home and $6,247.75 for a villa. Winding Cypress is not age-restricted: the Amended and Restated Declaration recorded in February 2024 contains no housing-for-older-persons provision and defines a family to include children.

We built this guide the way we price a listing here: from the recorded Declaration and its amendments, the district’s budgets and bond notices, the five recorded plats, Collier County’s parcel, zoning and flood layers, FEMA’s current map, the builder’s archived pages and the Southwest Florida MLS. Every figure carries its source and its date, and where the public record stops, we say so.

Why McGreevy and Comisar Are the Best Realtor for Winding Cypress

McGreevy and Comisar are the best realtor for Winding Cypress because the case rests on the record: the #1 team in Southwest Florida since 2012, Top 1% of agents nationally since 2008, over $900 million in personal sales, and a Winding Cypress read built from the Declaration, the district’s budgets, the recorded plats, FEMA’s map and the MLS.

Data updated: September 2026 (Southwest Florida MLS, Development: Winding Cypress, pulled September 23, 2026)

If you’re searching for the best realtor for Winding Cypress, whether you’re ready to sell your Winding Cypress home or buy your next one, McGreevy and Comisar is the team that delivers. We lead Domain Realty Group, the #1 real estate team in Southwest Florida since 2012, Top 1% Nationally since 2008, with over $2.5 billion sold as a team and $900 million in personal sales between Jesse and Marc. As the leaders of Domain Realty Group our team has closed over $2.5 billion in real estate, and Jesse and Marc together account for over $900 million in personal sales inside that number.

Recent Winding Cypress track record (last 12 months):

• 48 Winding Cypress homes sold between September 24, 2025 and September 23, 2026, for $38,718,900 in total dollar volume, per the Southwest Florida MLS (Development: Winding Cypress, pulled September 23, 2026).
• Median sale price $807,500 across all 48 sales, the midpoint of the two middle sales ($800,000 and $815,000). Single-family homes: 35 sales, median $875,000. Attached villas: 13 sales, median $575,000.
• Median 73 days on market (46 of the 48 sales carry a days-on-market figure) and a median sale-to-list ratio of 95.67%; 7 of the 48 homes sold at or above their list price.
• Highest-priced sale: $1,495,000, 7412 Winding Cypress Drive, closed March 11, 2026, a 3,656-square-foot home. The 48-month record is $1,895,000 for 7513 Winding Cypress Drive, closed January 4, 2024.
• On September 23, 2026, 9 homes were for sale and 2 were pending, about 2.2 months of supply.

In the last 12 months we tracked every one of those 48 Winding Cypress closings against the county roll, street by street and plat by plat, and that is the read we bring to a listing appointment here.

For luxury Winding Cypress sellers: Premium marketing, cinematic video, drone, professional photography, qualified-buyer database, discretion + off-market capability when needed.

A Winding Cypress sale also runs on paperwork ordered in the right sequence: the estoppel certificate, which states the account balance and the association’s own fee; the buyer’s resale capital contribution, $1,050 per resale in 2025 according to the association’s 2025 audit; the association’s Certificate of Approval, which the Declaration requires the association to record and does not let it withhold on a sale; the district assessment tier for the lot, which differs by product and by phase; and any FEMA Letter of Map Revision based on Fill for the lot, which can change a buyer’s flood insurance requirement. We put all of it in the listing file on day one.

Honors and recognition:

• Top 1% Real Estate Agents Nationally Since 2008
• 5 Star Award for Customer Satisfaction for 21 Straight Years. Only 5 out of 21k+ Licensees (Gulfshore Life Magazine)
• #1 Team in Southwest Florida since 2012
• McGreevy and Comisar and their Domain Realty Group team have sold over $2.5 Billion in Real Estate
• McGreevy and Comisar alone have over $900 million in Sales
• Nationally Recognized Top Producing Realtors
• Platinum Sales Production Award Winners

Jesse McGreevy is a top-reviewed Winding Cypress realtor, and the quotes below are five-star client reviews reproduced in each reviewer’s own words. Read the full set on the McGreevy and Comisar Google Business Profile.

★★★★★ “If you’re looking for a Realtor in Naples (or nearby areas), Jesse is your guy. I referred a friend to him for a winter home search. He has great connections, sharp negotiating, and he found them an off-market brand new build. Highly recommend!” Verified Google review

★★★★★ “I have had 13 real estate transactions and this is the most professional and helpful agency that I have ever worked with. Marc actually called me with a response to my questions and concerns on a Sunday evening. The resources that this agency has access to goes above and beyond any other I have ever worked with. The professional process that they use to present your home for sale goes beyond anything I have ever experienced. If any one is thinking about selling, Domain Realty should be the only agency that you should use to represent you and your home. You will not be disappointed.” Verified Google review

★★★★★ “Marc was great! He helped us find a place that matched our needs, without trying to upsell us into something too big. And he’s helped us settle into the area. 100% recommendation!” Verified Google review

Selling your Winding Cypress home? Get a free Winding Cypress home valuation, or Call Jesse direct at (239) 898-6072. Confidential conversations are welcome for luxury listings. Our guide to selling your home in Winding Cypress covers pricing by series and plat and the flood and CDD file.

Buying a home in Winding Cypress? Call Marc at (239) 287-5873 for a personalized buyer consultation, or read how we represent buyers in Winding Cypress.

Office: 24031 S Tamiami Trl #101, Bonita Springs, FL 34134 · Jesse McGreevy: (239) 898-6072 · [email protected] · Marc Comisar: (239) 287-5873

Jesse McGreevy (Sales Associate) and Marc Comisar (Broker Associate) are licensed Florida REALTORS® with Domain Realty; Florida real estate licensure is regulated by the Florida Real Estate Commission (FREC).

Key Takeaways

Winding Cypress is a gated DiVosta community of 766 homes in East Naples where the public record answers most buyer and seller questions directly. These eight facts matter most: what sells for how much, what the two assessments add up to, what the flood map says, who can live here, and what the community does and does not have.

Data updated: September 2026

• 766 homes: 152 attached villas, 406 Classic homes on 50-foot homesites and 208 Estate homes on 65-foot homesites. The Winding Cypress CDD’s fiscal 2026/27 budget and the association’s 2026 approved budget both count 766, all of them fee-simple homes on platted lots, with no condominiums.
• A $875,000 median single-family sale and a $575,000 median villa sale. Those are the trailing 12-month Southwest Florida MLS medians (September 24, 2025 to September 23, 2026; 35 single-family and 13 villa sales), at $405.92 and $370.01 per square foot of living area.
• 2.2 months of supply and a 95.67% median sale-to-list ratio. Nine homes were active on September 23, 2026 against 48 closings in 12 months, a tight inventory position in which buyers still negotiated about 4% off list at the median.
• The 2026 association assessment runs $6,247.75 to $7,067.22 a year by series, and it went down about 1%. The approved budget bundles lawn and irrigation care, the clubhouse, reserves and a $484 food-and-beverage minimum; there is no club initiation fee or equity membership.
• The district adds $1,643.98 to $2,338.98 a year on the tax bill. Every home pays $794.98 of district operations and maintenance, plus bond debt of $849 to $1,544 by product and phase, per the CDD budget, before the 4% November discount.
• FEMA’s current map puts Winding Cypress in Zone AE, with a base flood elevation of 8.0 feet. The National Flood Hazard Layer returned Zone AE at all 13 addresses we sampled on the map effective February 8, 2024; about 15 homes hold their own FEMA letters moving the lot or structure to shaded Zone X. The community is in hurricane Evacuation Zone D on the county layer.
• Winding Cypress is an all-ages community, and its schools are A-rated through middle school. The district’s own address lookup assigns Lely Elementary, Manatee Middle and Lely High for 2026-27, graded A, A and B in the state’s 2026 school grades.
• There is no golf course, no marina and no lake use. The 2026 Rules list 4 clay tennis courts, 8 pickleball courts and 4 bocce courts, and bar fishing, boating and swimming in the district’s 29 stormwater lakes. The nearest beaches are about 21 to 23 minutes away without traffic.

Table of Contents

This guide to Winding Cypress runs from daily life and the market, through the community’s origins, land, governance and full fee stack, the home series including the villas, The Club and its amenities, storms, flood zones and insurance, schools, healthcare, drive times, what is being built nearby, the comparisons buyers ask for, and both FAQ sets. Jump to what you need, or read it in order.

Start here

• Why McGreevy and Comisar Are the Best Realtor for Winding Cypress
• Key Takeaways
• Table of Contents

Living here and the market

• What Is It Like to Live in Winding Cypress as a Homebuyer?
• What Is the Winding Cypress Real Estate Market Doing Right Now?

Origins, land and governance

• How Did Winding Cypress Come to Be?
• How Big Is Winding Cypress, and What Zoning Governs It?
• Who Governs Winding Cypress?
• What Will You Actually Pay to Own a Home in Winding Cypress? (The Fee Stack)
• What Types of Homes Make Up Winding Cypress, Including the Villas?

Club and amenities

• What Is in The Club at Winding Cypress, and Do You Have to Join?
• Does Winding Cypress Have a Golf Course?
• How Far Is Winding Cypress From the Beach?
• How Many Pickleball and Tennis Courts Does Winding Cypress Have?
• What Fitness, Pool and Walking Amenities Does Winding Cypress Offer?
• Where Can You Eat Inside Winding Cypress?
• What Clubs, Classes and Events Happen in Winding Cypress?

Storms, flood, insurance and services

• How Storm-Ready Is Winding Cypress?
• What Flood Zone Is Winding Cypress In?
• What Should You Know About Insuring a Home in Winding Cypress?
• Which Schools Serve Winding Cypress?
• Where Is the Nearest Hospital to Winding Cypress?
• How Long Are the Drives From Winding Cypress?
• What Is Being Built Near Winding Cypress?
• How Do the Gate, Leasing, Pets, Utilities and Trash Work in Winding Cypress?

Comparisons and decisions

• Winding Cypress vs Verona Walk: Which DiVosta Community Fits You?
• How Does Winding Cypress Compare With Other East Naples Communities?
• What Are the Honest Pros and Cons of Buying in Winding Cypress?

Selling, experts and answers

• Thinking of Selling Your Winding Cypress Home? List With the #1 Team in Southwest Florida Since 2012
• Your Local Real Estate Experts
• Frequently Asked Questions, Buyer Edition
• Frequently Asked Questions, Seller Edition
• Sources and Authoritative References
• Downloadable Documents

What Is It Like to Live in Winding Cypress as a Homebuyer?

Living in Winding Cypress means a gated, all-ages DiVosta community of 766 homes in unincorporated East Naples, with about 818 acres of recorded preserve, 29 stormwater lakes, a clubhouse with a poolside restaurant bundled into the association assessment, and a hospital, a Publix and an interstate exit within about 11 minutes of the gate.

Data updated: September 2026

Winding Cypress is a newer, quieter kind of Naples neighborhood. Every home was built by one builder over nine years, from the first recorded closing on June 30, 2015 to the last on December 21, 2023, per the Collier County Clerk’s recorded first and last builder deeds. Most of the streets carry the names of Florida plants: Live Oak, Jacaranda, Pennyroyal, Cocoplum, Blackberry, Bromeliad, Geranium. Most homes back onto either a lake or a preserve, and the preserve is not a landscaped buffer but a recorded, permanently protected wetland and forest system that joins a 74,138-acre state forest.

Where Winding Cypress sits in East Naples

Winding Cypress sits north-east of US 41 (Tamiami Trail East) and east of Collier Boulevard (County Road 951), with US 41 as its south-west border. The district engineer’s 2015 report places it in the “Northeast quadrant of the intersection of Tamiami Trail East (US 41) and Collier Boulevard”, and the Census Bureau draws a census-designated place around it under its own name, Winding Cypress, on the 2020 TIGERweb layer. Verona Walk borders it to the north.

The main entrance is at Winding Cypress Boulevard and Collier Boulevard. No city limit touches the community: Collier County handles zoning, permits and inspections, the mailing address is Naples 34114, and fire and rescue come from the Greater Naples Fire Rescue District, per the county’s fire district layer. Every drive time on this page is measured from the Collier Boulevard gate with OpenStreetMap routing without traffic; January to April adds time on Collier Boulevard and US 41.

A gated, all-ages community by covenant

Winding Cypress is not age-restricted. The association’s Amended and Restated Declaration, Articles and Bylaws, adopted by the members on February 5, 2024 and recorded on February 16, 2024 at Official Records Book 6330, Page 3383, contains no housing-for-older-persons clause, and its definition of “Family” includes children. The builder sold it the same way: DiVosta described its Mystique plan in 2020 as “well-suited for families and empty nesters alike,” per Florida Weekly (December 3, 2020). DiVosta is a PulteGroup brand, separate from the company’s Del Webb brand.

Winding Cypress is gated. A gatehouse with attendants serves the Collier Boulevard entrance, backed by license-plate readers and a virtual callbox, and a second, automated rear gate with a barcode reader and cameras serves the south end, per the association’s Visitors and Agents page and its September 2025 board minutes. Residents issue guest passes through a mobile app. The Declaration itself disclaims any obligation to provide security, so we describe the entrance as gated rather than as a security service.

Three product lines on one plan

The 766 homes follow DiVosta’s three product lines, set out in the builder’s Winding Cypress digital brochure. The Villa Series is 152 attached, paired villas on Jacaranda Lane and the 7093 to 7202 block of Live Oak Drive. The Classic Series is 406 detached homes on 50-foot homesites, with plans such as the Palmary, Prestige, Prosperity and Mystique running from about 1,670 to 3,037 air-conditioned square feet. The Estate Series is 208 detached homes on 65-foot homesites, with the Pinnacle, Tangerly Oak and Stonewater plans running from about 2,488 to 3,894 air-conditioned square feet.

The builder’s specification is the same across the line: steel-reinforced concrete block construction, engineered roof trusses with hurricane tie-downs, a tile roof and galvanized steel hurricane shutters as standard, with impact glass as an option. On the Southwest Florida MLS, the median living area of a single-family home sold in the last 12 months was 2,158 square feet, and of a villa 1,554 square feet. The home-types section later in this guide takes each series, plat and street in turn, and gives the villas their own treatment.

Life beside 818 acres of preserve

The preserve is the defining feature of Winding Cypress. On Collier County’s parcel layer, 818.27 of the 1,176.24 acres on the five Winding Cypress plats are recorded preserve tracts, about 70 percent of the platted land, and a perpetual conservation easement granted to the South Florida Water Management District on July 10, 2014 protects the conservation areas inside the community’s parent tract. Beyond the preserve lies the Picayune Strand State Forest, 74,138 acres managed by the Florida Forest Service.

Residents see the preserve from a wooden boardwalk that leads to a sheltered overlook and a bird wading overlook; the boardwalk closes at sunset, and the 2026 Rules do not allow entry into the preserve itself. The surrounding lands are home to Florida panthers, black bears, wood storks and red-cockaded woodpeckers, per the Florida Fish and Wildlife Conservation Commission’s Picayune Strand page, and in January 2025 a family of four black bears was filmed walking through Winding Cypress, per WINK News. The same forest brings seasonal smoke: the Florida Forest Service runs prescribed burns in Picayune Strand, including an 818-acre burn that began on December 10, 2025, per WINK News.

The clubhouse at the center of daily life

Daily life gathers at The Club at Winding Cypress, 7180 Winding Cypress Drive, on the 6.61-acre association Tract G, built in 2016 per the state roll. DiVosta marketed a 17,500-square-foot clubhouse, and its builder, DeAngelis Diamond, describes a 22,000-square-foot amenity center. Around it sit a heated resort-style pool with lap lanes, a spa, a fitness center with a Movement Room, clay tennis, pickleball and bocce courts, two dog parks and a community garden, per the association’s amenities page. The Shady Palm Café, a poolside bar and restaurant, is run by the association with its own manager and chef.

Membership comes with the home. The clubhouse is owned by the homeowners association, access is by key fob, and the cost is inside the assessment, so there is no initiation fee, no equity membership and no non-resident membership. The association lists official clubs from pickleball, tennis and bocce to a book club, a garden club, water aerobics and card groups on its Clubs page. The amenity and club sections later in this guide cover each facility in detail.

Full-time and seasonal owners

Winding Cypress is a mix of year-round residents and seasonal owners, and the association has measured it. In the association’s certified October 2025 survey, 360 of the 766 households responded, and 56.3 percent described themselves as full-time residents and 43.7 percent as part-time. In practice that means a fuller clubhouse calendar from about November to April, with dances, craft fairs and ticketed season-end parties, and a quieter summer when the Shady Palm Café shortens its week.

Errands, schools and the hospital within minutes

The daily errands are close. From the Collier Boulevard gate, OpenStreetMap routing without traffic puts the Publix at Freedom Square 1.7 miles and about 4 minutes away, Physicians Regional Medical Center on Collier Boulevard 2.2 miles and about 3 minutes away, Interstate 75 at Exit 101 6.1 miles and about 11 minutes away, Fifth Avenue South in downtown Naples 9.8 miles and about 18 minutes away, and Southwest Florida International Airport 38.8 miles and about 49 minutes away. The Naples Pier is 11.1 miles and about 21 minutes away, and Tigertail Beach on Marco Island 11.4 miles and about 23 minutes.

For families, the district’s 2026-27 address lookup returned the same three schools for every address point on the 13 streets tested: Lely Elementary, Manatee Middle and Lely High, all within about 7 minutes of the gate. The schools, hospitals and drive-time sections later in this guide carry the full tables.

One front door shared with Verona Walk

One detail most buyers never hear about until closing is the entry drive. Winding Cypress and Verona Walk, its northern neighbor and the other DiVosta community in the same planned development, share facilities on the entry road from Collier Boulevard under a recorded Cost Sharing Agreement dated February 24, 2014 (Official Records Book 5011, Page 1411). The Winding Cypress association operates, maintains, insures and replaces the shared road, bridge, fountain, drainage and entry-road landscaping, and the Verona Walk association pays 31 percent of those costs in quarterly installments. Utilities and each community’s entry signage are excluded.

When we walk a Winding Cypress buyer through the association’s budget, this is one of the lines we point to, because it explains why the Winding Cypress association maintains, insures and budgets for a road, a bridge and a fountain that also serve the homes of its neighbor. It is also a reminder that the two communities, although they share a builder, a front door and a high school, are governed separately, with separate associations, separate districts and separate budgets.

What Winding Cypress does not have

A buyer should know the absences as clearly as the amenities. There is no golf course inside Winding Cypress; the nearest public golf is at Lely Resort’s Mustang and Flamingo Island courses, which require no membership, about 2.6 road miles and 7 minutes from the clubhouse, per Lely Resort Golf. There is no marina and no boat access to the Gulf, and boats and trailers must be kept in a garage under the Declaration. The 29 lakes are stormwater lakes owned by the community development district, and the 2026 Rules allow “no recreational or other access (including but not limited to fishing and water toys),” so fishing, boating and swimming are not allowed.

There are no condominiums and no apartments: every home is a fee-simple home on its own platted lot, and the attached product is a paired villa, not a condominium or townhome. There is no spa-services business on site. And Winding Cypress is no longer a new-construction community: DiVosta’s archived page read “Only one opportunity remains” on December 9, 2023, and the builder’s last recorded closing followed on December 21, 2023. A Winding Cypress purchase is a resale purchase, which puts the weight on the documents a seller provides: the estoppel certificate, the district assessment tier for the lot, the flood determination and the association’s Certificate of Approval.

Choosing the agent for a Winding Cypress move

A resale community with one builder, three product lines, two district debt tiers and a flood map that changed in 2024 rewards an agent who reads the documents before pricing the home. If you are comparing agents for a Winding Cypress sale or purchase, our guide to the best real estate agents in Naples sets out production, reviews and license history on the public record.

Selling in Winding Cypress? Get a free Winding Cypress home valuation, or Call Jesse direct at (239) 898-6072. Buying in Winding Cypress? Call Marc at (239) 287-5873, or read how we represent buyers in Winding Cypress.

What Is the Winding Cypress Real Estate Market Doing Right Now?

Winding Cypress recorded 48 closed sales in the 12 months to September 23, 2026, at a median of $807,500, with single-family homes at a median of $875,000 and attached villas at $575,000, per the Southwest Florida MLS. Inventory is tight at 2.2 months of supply, and homes sold at a median 95.67% of list price.

Data updated: September 2026 (Southwest Florida MLS, Development: Winding Cypress, pulled September 23, 2026; trailing 12 months = sales closed September 24, 2025 to September 23, 2026)

Every figure in this section comes from one Southwest Florida MLS search on the Development Name Winding Cypress, which returned exactly one dictionary entry and no neighboring community to exclude: 181 listings closed in the last four years or active or pending on September 23, 2026. Each listing carries the MLS Building Design label its listing agent chose, either “Single Family” or “Villa Attached”, and the tables split the market on that label. Every median is the middle sale of its group, and where a count is even the median is the midpoint of the two middle sales, both shown. Price per square foot is each sale price divided by that home’s MLS living area, then the median of those ratios; it is a living-area figure and is never comparable to a county-roll figure measured on total area under roof.

The twelve-month MLS picture

Winding Cypress closed 48 sales in the trailing 12 months, for $38,718,900 in volume, per the Southwest Florida MLS.

Source: Southwest Florida MLS, Development: Winding Cypress, closed September 24, 2025 to September 23, 2026, pulled September 23, 2026. Two sales were entered into the MLS after closing and carry no days-on-market figure, which is why the days-on-market medians use 46 and 33 sales.

Two readings matter most. The first is the gap between the segments: at the median, a Winding Cypress single-family home sold for $300,000 more than a villa and for about $36 more per square foot of living area. The second is the negotiating room: the median home sold at 95.67% of its final list price, and only 7 of 48 sold at or above list, so a buyer should expect to negotiate and a seller should expect to price for it.

One caution on the segment split. The Building Design label is entered by the listing agent, and county records place at least two Live Oak Drive homes that sold in this window under the single-family label on the block of attached villas between 7093 and 7202 Live Oak Drive. We publish the MLS medians exactly as the MLS reports them, and we read the single-family and villa lines as close approximations rather than exact counts.

Single-family homes and villas, side by side

The single-family market in Winding Cypress spans the Classic and Estate series, and the MLS carries no field that tells a 50-foot homesite from a 65-foot homesite, so the 35 single-family sales are one line. They ranged from $575,000 to $1,495,000, with a median of $875,000 and $405.92 per square foot of living area, and a median of 76 days on market.

The villa market is narrower and faster. The 13 villa sales ranged from $455,000 to $635,000, with a median of $575,000 and $370.01 per square foot of living area, and sold in a median of 50 days. The three lowest-priced sales of the year were all villas on Jacaranda Lane: $455,000 for 7642 Jacaranda Lane on November 17, 2025, $460,000 for 7658 Jacaranda Lane on March 12, 2026, and $470,000 for 7638 Jacaranda Lane on June 24, 2026.

At the top, the three highest-priced sales of the year were $1,495,000 for 7412 Winding Cypress Drive (March 11, 2026, 3,656 square feet of living area), $1,475,000 for 6912 Cocoplum Street (May 13, 2026) and $1,260,000 for 6839 Winding Cypress Drive (November 21, 2025). Over the four years of MLS history we pulled, the record is $1,895,000 for 7513 Winding Cypress Drive, closed January 4, 2024.

Where the 48 sales happened, street by street

Sales in the last 12 months were concentrated on the community’s longest streets. Street names follow Collier County addressing.

Source: Southwest Florida MLS, Development: Winding Cypress, pulled September 23, 2026. Six streets recorded no MLS sale in the window: Lily Way, Wiregrass Court, Arrowhead Way, Chenille Court, Greenbriar Court and Bromeliad Drive. With 766 homes on 15 residential streets, a street with no sale in one year is common and says nothing about demand for it.

The year before, for comparison

In the prior 12 months, September 24, 2024 to September 23, 2025, Winding Cypress recorded 40 closed sales, so closings rose 20 percent to 48 this year, per the same Southwest Florida MLS search.

Source: Southwest Florida MLS, Development: Winding Cypress, pulled September 23, 2026.

Read together, the two years say the market held its level while its mix shifted. The all-home median was $807,500 in both years, built from different middle pairs. The single-family median rose 1.7 percent, from $860,000 to $875,000, while the single-family price per square foot of living area slipped 2.8 percent, from $417.66 to $405.92, which means larger homes made up more of this year’s sales. The villa median rose 2.7 percent, from $560,000 to $575,000, and villa days on market fell from 107 to 50. These are small samples, 31 and 35 single-family sales and 9 and 13 villa sales, so a handful of closings can move any of these medians.

Four calendar years of Winding Cypress sales

The calendar-year view shows where Winding Cypress peaked and how far it has come back, per the same Southwest Florida MLS search.

Source: Southwest Florida MLS, Development: Winding Cypress, pulled September 23, 2026. Our search began on September 24, 2022, so 2022 is not shown as a full year.

The single-family median peaked in 2024 at $1,000,000, reset about 14 percent in 2025 to $860,000, and is up about 4.1 percent in 2026 to date at $895,000. Villas peaked earlier, at a $710,000 median in 2023, fell to $537,000 in 2025, about 24 percent below the peak, and are up about 7.1 percent in 2026 to date at $575,000. A second public record agrees on the 2024 peak: the Florida Department of Revenue’s qualified-sale file for 2025 roll purposes, served on the state’s statewide cadastral layer, also shows a 2024 single-family median of $1,000,000, on 31 qualified sales. Qualified sales are arm’s-length transfers screened under the Department’s sale qualification codes; they are a different record from the MLS, and we cite them only as corroboration.

What is for sale now, and months of supply

On September 23, 2026, 9 Winding Cypress homes were active on the Southwest Florida MLS, 1 was pending with a contingency and 1 was pending.

Source: Southwest Florida MLS, Development: Winding Cypress, pulled September 23, 2026. The two pending listings were at $1,200,000 (pending with contingency) and $799,900. Months of supply is the number of active listings divided by the average number of closings per month over the last 12 months.

At 2.2 months of supply, Winding Cypress inventory is tight: a seller faces few competing listings, and a buyer who wants a specific series or street may wait for one. The asking prices on the seven active single-family homes, a median of $1,250,000, sit well above the $875,000 median single-family sale of the last 12 months. Against a median sale-to-list ratio of 95.67%, that gap is where the next few closings will settle the question of whether 2026 ends closer to the 2024 peak or to the 2025 reset.

What the numbers mean for sellers and buyers

For a seller, three facts from this section carry most of the pricing work. The villa market moved fastest this year, at a median of 50 days on market, so a well-presented villa priced at the market tends to go quickly. The single-family market spans a wide range, from $575,000 to $1,495,000, so the comparable sales for a Classic home on a 50-foot homesite and an Estate home on a 65-foot homesite on a preserve lot are not the same sales, even though the MLS does not separate them. And the district’s debt tier, which is higher on the Phase 3 streets, belongs in the pricing conversation, because a buyer compares the whole annual carrying cost.

For a buyer, the tight inventory argues for preparation: an approved loan, a view on which series and which phase fit, and a clear read of the flood determination and the district assessment for the specific lot. The median sale-to-list ratio says there is still room to negotiate, but the 7 of 48 sales at or above list say it is not universal.

Thinking of Selling or Buying in Winding Cypress, Where 48 Homes Sold in 12 Months?

Winding Cypress sold 48 homes in the last 12 months, at a median of $875,000 for a single-family home and $575,000 for a villa, and only 9 were for sale on September 23, 2026. If you own here, a valuation grounded in the street, the series, the phase and the district tier of your home is the place to start: get a free Winding Cypress home valuation, or Call Jesse direct at (239) 898-6072 for a confidential conversation. If you are buying, Call Marc at (239) 287-5873, and read how we represent buyers in Winding Cypress before you tour.

How Did Winding Cypress Come to Be?

Winding Cypress was built by DiVosta Homes on Barron Collier land entitled in 1999 as the southern part of the Winding Cypress Development of Regional Impact, whose northern part became Verona Walk. DiVosta bought the land in three takedowns from 2014 to 2018, opened its model park on March 14, 2015 and closed its last home in December 2023.

Data updated: September 2026 (Collier County Clerk recorded instruments, district records, builder archive captures and dated news, retrieved September 23 and 24, 2026)

Barron Collier land and the 1999 approval

The land under Winding Cypress belonged to Barron Collier Company, which signed the approval as landowner. On December 14, 1999, the Collier County Board of County Commissioners adopted Development Order 99-4 by Resolution 99-467, approving the Winding Cypress Development of Regional Impact, per the Notice of Adoption recorded on April 14, 2000. A Development of Regional Impact is Florida’s review process, under Chapter 380 of the Florida Statutes, for projects large enough to affect more than one county. The notice’s legal description runs from the south line of Sabal Palm Road down to US 41, across all of Sections 26 and 35 and parts of Section 34 of Township 50 South and Sections 2 and 3 of Township 51 South, Range 26 East.

The development order was amended by Resolution 02-302 in 2002, a 2006 resolution corrected a scrivener’s error in it, and in 2007 Barron Collier used a state law change, Chapter 2007-204, to extend every phase, build-out and expiration date by three years, per the Notice of Extension recorded on January 18, 2008. The zoning that governs both communities today is the Winding Cypress Planned Unit Development, covered in the next section.

Verona Walk first, Winding Cypress second

The approval covered two communities, and they were built a decade apart. DiVosta took the northern land first: Barron Collier deeded it to DiVosta and Company in 2003 by a special warranty deed recorded on September 3, 2003, with about $22.2 million of consideration, and that land became Verona Walk, which DiVosta sold through 2012. The southern land, called “Winding Cypress South” in the recorded easements, stayed with Barron Collier through the downturn that followed 2007.

When DiVosta returned, it bought the southern land in three recorded takedowns totaling $31,776,750:

Source: Collier County Clerk of Courts, Official Records, deeds as linked. Spread over the 766 homes that were built, that is about $41,500 of raw land per homesite, before any road, lake or clubhouse was built.

The same day as the first takedown, July 10, 2014, two other instruments were recorded that still shape the community. Barron Collier granted the South Florida Water Management District a perpetual Deed of Conservation Easement over the conservation areas of the 1,167.9-acre “Winding Cypress South” parcel, limited to passive recreational uses. And the Barron Collier entity that held the oil, gas and mineral rights recorded a Waiver of Surface Exploration Rights over the first takedown, so those rights stayed with the seller without a right to explore from the surface.

The association, the Declaration and the district, 2014 to 2015

DiVosta built the governing structure before the first home closed. It incorporated Winding Cypress Homeowners Association, Inc. on January 30, 2014, Florida not-for-profit document number N14000000923, per the Florida Division of Corporations. It signed the entry-road Cost Sharing Agreement with the Verona Walk association and Barron Collier on February 24, 2014. The original Declaration was recorded on November 25, 2014, at Official Records Book 5097, Page 2640, and was replaced by the Amended and Restated Declaration recorded in February 2024.

The Winding Cypress Community Development District followed. Collier County created it by Ordinance 2015-48, adopted September 9, 2015 and effective on filing on September 10, 2015, over about 358 acres, the developed footprint of the community. The district financed the roads, drainage and lakes with Series 2015 bonds for the first two phases and Series 2019 bonds for Phase 3, which is why every Winding Cypress home still carries a district debt line on its tax bill today, per the recorded Series 2015 and Series 2019 assessment notices.

Pre-sales, the model park and the first closings

DiVosta began pre-selling in December 2014 from a temporary sales center at Verona Walk, at prices from $263,990 to $419,990, per its archived page of December 15, 2014. A permanent sales center at 7225 Wiregrass Court and three decorated models, the Summerwood, the Martin Ray and the Pinnacle, followed, and the Model Park Grand Opening was held on Saturday, March 14, 2015, per the builder’s archived page of March 13, 2015. The first builder-to-buyer closing was recorded on June 30, 2015.

The builder’s “starting from” prices climbed steadily through the build-out, per its archived pages:

Source: DiVosta archived pages of December 15, 2014, March 13, 2015, September 18, 2016 and July 21, 2019. These are base prices before options and lot premiums, not sale prices.

The entry Serenity plan rose about 18.6 percent in four and a half years. By December 2020, DiVosta was pricing its new single-family plans “starting from the $400s to $700s,” per Florida Weekly. Today’s resale medians, $875,000 for a single-family home and $575,000 for a villa, sit far above every one of those launch prices.

Building out, 2015 to 2023

Construction ran phase by phase for nine years. The clubhouse was built in 2016, and DiVosta’s page that September carried an “Amenity Construction Update.” In March 2019 the builder released 200 more homesites, per the Business Observer (March 28, 2019); by June 2019 it had passed 500 homes sold, per Florida Weekly (June 6, 2019); and in late 2020 it introduced four new plans, the Mystique, Prestige, Prosperity and Palmary, with “homesites are now available in the final phase,” per Florida Weekly (December 3, 2020).

Counting DiVosta-to-buyer deeds in the Clerk’s Official Records index by year gives the pace of the build-out:

Source: Collier County Clerk of Courts, Official Records index, DiVosta Homes, L.P. deeds whose legal description reads “Winding Cypress Lot”.

Sell-out and the hand-over to owners

The build-out ended in December 2023. DiVosta’s page read “Only one opportunity remains” on December 9, 2023, and its last recorded Winding Cypress closing followed on December 21, 2023. By then the builder had already handed the community’s land to the two bodies that own it today. In October 2021 DiVosta deeded the lake tracts and most of the preserve tracts to the community development district, per the recorded deed to the district, and in January 2022 it deeded the roads, the clubhouse tract and the other common tracts to the homeowners association, per the recorded quit-claim deed.

Owners took control of the association board by February 2022: the association’s 2022 annual report is the first to list an owner board rather than builder officers. The district followed more slowly. DiVosta still controlled the district’s landowner election in November 2022, residents were appointed to three district seats in June 2023, per the district’s June 29, 2023 meeting book, and Seats 1, 3 and 5 go to resident voters in the general election on November 3, 2026, per the Clerk’s published qualifying-period notice.

One piece of the land never left the builder. DiVosta still holds a 230.22-acre preserve remainder of Phase 2 Tract P1, carried at a just value of $100 on Collier County’s parcel layer. The record does not say why that remainder was not conveyed with the other preserve tracts; it is conservation-restricted preserve with no development value.

The lake-bank question of 2023

The hand-over left one open question, and a buyer reading the district’s budgets will see its effect. On June 6, 2023, the newly resident-controlled district board authorized a preliminary investigation of potential claims against DiVosta over lake banks “not being in good repair,” after the South Florida Water Management District inspected the lakes, per the district’s June 29, 2023 meeting book. The district then commissioned a full lake assessment from LJA Engineering, dated March 21, 2024, which counted 29 lakes and logged hundreds of bank conditions, most of them erosion behind homes.

No lawsuit or settlement appears in the public record we reviewed. What does appear is the cost: the district’s operations and maintenance assessment rose from $232.06 a home in fiscal 2022/23 to about $795 in fiscal 2023/24, driven by a lake-bank remediation line, and has held at $794.98 since, per the district’s fiscal 2022/23 and fiscal 2026/27 budgets. The fee stack section of this guide carries the full district line by line.

Storms during the build-out

Winding Cypress was built through two of the region’s defining hurricanes. Irma made its final Florida landfall near Marco Island in September 2017, per the National Hurricane Center’s tropical cyclone report, while DiVosta was still building. After Hurricane Ian in September 2022, the district’s minutes of its November 1, 2022 meeting record that “No significant damage was noted by the community,” per the district’s February 7, 2023 meeting book. The storm and flood sections later in this guide carry the full record, street by street.

How Big Is Winding Cypress, and What Zoning Governs It?

Winding Cypress covers about 1,176 acres across five recorded plats, of which about 818 acres are recorded preserve tracts and about 358 acres form the developed district footprint. Winding Cypress is zoned under the Winding Cypress Planned Unit Development, Ordinance 02-35 as amended, most recently by Ordinance 2014-09, a PUD it shares with Verona Walk.

Data updated: September 2026 (Collier County parcel, PUD and future land use layers; recorded plats; district ordinance and engineer’s report; retrieved September 23 and 24, 2026)

Acreage is the most misquoted fact about Winding Cypress, because at least six different numbers circulate and they measure different things. The figures below are the ones the public record supports, each with what it measures.

What each acreage figure measures

The two numbers that describe the community a buyer lives in are the first two: about 1,176 acres on the plats, about 818 of them preserve. The district footprint, about 358 acres, matches the plats almost exactly once the preserve is taken out: 1,176.24 acres less 818.27 acres of preserve leaves 357.97 acres, within a tenth of an acre of the ordinance.

How the 1,176 acres are used

The county’s parcel layer divides the 828 parcels on the five plats into five classes.

Source: Collier County Growth Management GIS, Parcels layer, retrieved September 2026. Shares are rounded.

The 766 home lots take up less than an eighth of the land. That is the single number that best explains how Winding Cypress feels: a compact neighborhood of homes and lakes set into a much larger preserve. The largest preserve tracts are Phase 2C Tract P2 at 260.30 acres, owned by the district, and the 230.22-acre Phase 2 Tract P1 remainder still held by DiVosta; the largest lake tract is Phase 3 Tract L-3 at 18.50 acres.

The five recorded plats

Winding Cypress was platted in five instruments between 2015 and 2018, recorded in the Collier County plat books.

Source: Collier County Clerk plat index (the Phase One entry is linked; the others are in the same index) and the county parcel layer for home counts.

Phase One holds the clubhouse tract and most of the preserve-edge lots; Phase 3 is the newest section, built from 2019 to 2023, and carries the higher Series 2019 district debt. In 2015 the district engineer planned about 781 homes; 766 were built. The home-types section later in this guide carries each street’s product and the villa blocks in detail.

One PUD, two communities

The zoning that governs Winding Cypress is the Winding Cypress Planned Unit Development, Ordinance 02-35, as amended, most recently by Ordinance 2014-09, per Collier County’s list of PUD ordinances. The original 1999 rezone, Ordinance 99-93, was replaced by Ordinance 02-35 in 2002, and the PUD was amended again in 2002, 2009 and 2014. The Winding Cypress PUD, about 1,928 acres approved for 2,854 units, covers both Verona Walk and Winding Cypress; about 2,686 homes are built in it, 1,920 in Verona Walk and 766 in Winding Cypress. The county’s PUD master list now marks the project built out.

The PUD still matters to an owner, because it sets what can change on the common land. In March 2026, when owners appealed a site-plan change converting a clay tennis court into pickleball courts, the Collier County Hearing Examiner’s notice described the clubhouse land as the 6.61-acre Tract G in “the Recreational District of the Winding Cypress Planned Unit Development, Ordinance No. 02-35, as amended.” The appeal was denied, and the amenity section of this guide covers the courts as they stand.

On the county’s future land use map, Winding Cypress sits in the Urban Residential Fringe Subdistrict, and it lies outside the county’s Coastal High Hazard Area. It is in County Commission District 1, per the county’s projects layer.

Lakes, wetlands and the permits behind them

The water system was engineered before the first home. The district engineer’s 2015 report planned 83.4 acres of lakes (17.2 in Phase 1, 43.4 in Phase 2 and 22.8 in Phase 3), sized roads and basins for a 25-year, 3-day storm and buildings for a 100-year, 3-day storm, and sent the lakes’ regulated outfalls to “the natural wetland slough system that expands through the center of the development.” Stormwater runs from gutters and inlets to the lakes, which are linked by large pipes and controlled by structures at their outfalls.

The system operates under South Florida Water Management District environmental resource permit 11-02132-P and its modifications, whose permittee for Winding Cypress and Phase 3 is now the district, per the water management district’s permit layer; the Verona Walk Town Center sits under a separate modification held by the Verona Walk association. The federal wetland permit is U.S. Army Corps of Engineers file SAJ-1996-01924. The conservation easement of July 10, 2014 binds the protected areas to passive recreational uses in perpetuity, which is why the preserve behind a Winding Cypress home will stay preserve.

Homes by year built

The state’s 2025 roll records an actual year built for the homes, and the pattern follows the build-out: the busiest years were 2016 to 2019, and the Phase 3 homes date from 2019 to 2023.

Source: Florida Department of Revenue statewide cadastral layer, 2025 roll, actual year built, retrieved September 2026.

Who Governs Winding Cypress?

Winding Cypress is governed by two bodies. The Winding Cypress Homeowners Association, a Florida not-for-profit incorporated in 2014 and managed by Seacrest Southwest Property Management, owns the roads, clubhouse and recreation tracts. The Winding Cypress Community Development District, a Chapter 190 special district created by Collier County in 2015, owns the lakes and most of the preserve.

Data updated: September 2026

The split matters to every buyer because the two bodies bill in different ways. The association is a private corporation run by a board the owners elect, and it bills its assessment quarterly. The district is a unit of local government with its own elected board of supervisors, a budget adopted at a public hearing, an annual audit and its own line on the November property tax bill. There is no master association above the homeowners association and no separate villa, Classic or Estate association below it.

The Winding Cypress Homeowners Association

Winding Cypress Homeowners Association, Inc. is a Florida not-for-profit corporation, document number N14000000923, filed January 30, 2014 and active, per the Florida Division of Corporations. It is the only association in the community. A starts-with search of the state’s corporate register for the Winding Cypress name returns the association, two service marks the association registered in 2025 and an unrelated private rental company, and nothing else: no villa association, no neighborhood association and no condominium association, per the Division of Corporations name list.

Membership is automatic with the deed. Every one of the 766 homes, whether an attached villa on Jacaranda Lane or an Estate home on a 65-foot homesite on Pennyroyal Drive, belongs to the same association, pays into the same budget and has the same access to the clubhouse, courts and pool.

Owners took control of the association board by February 2022, the year its 2022 annual report lists the first owner board, and DiVosta deeded the roads, clubhouse and common tracts to the association in January 2022, per the recorded quit-claim deed. The public record holds no single dated turnover meeting; those two records are what fix the handover. The current five-member board is listed on the association’s 2026 annual report, filed April 10, 2026.

The governing documents and how they change

The community’s constitution is the Amended and Restated Declaration of Covenants, Articles of Incorporation and Bylaws, adopted by the members on February 5, 2024 and recorded February 16, 2024 at Official Records Book 6330, Page 3383, per the Collier County Clerk’s image. It replaced the original Declaration that DiVosta recorded on November 25, 2014.

Two recorded changes shape how the owners run the place today. In November 2023 the owners lowered the vote thresholds for amending the documents to a majority, recorded at Official Records Book 6301, Page 3443 (Clerk record). That lower bar is the reason the full restatement could pass three months later. And on September 12, 2025 the association recorded a hurricane shutter amendment to Section 9.20 at Official Records Book 6507, Page 955 (Clerk record; association copy).

Below the Declaration sit the board’s Rules and Regulations. The association posts both the May 2024 Rules and the 2026 Rules, final draft, which carries the current amenity inventory. The Declaration outranks the Rules, but the Rules are what the architectural reviewer and the manager apply day to day.

Seacrest Southwest and the on-site staff

The association is managed by Seacrest Southwest Property Management, 1044 Castello Drive, Suite 206, Naples 34103, (239) 261-3440, per the association’s contact page. The management company is a community association manager; it does not list or sell homes. The on-site team works from the association office at the clubhouse, 7180 Winding Cypress Drive, (239) 732-7171, and the roles it lists are a general manager, an activities director, a maintenance supervisor and the Shady Palm Café’s own manager and chef.

That on-site bench is larger than many Collier associations of this size carry, and it is paid for inside the assessment. The 2026 approved budget carries a single HOA operating component of $3,103.79 per home that funds management, staff, insurance and administration, per the 2026 Approved Budget.

The Winding Cypress Community Development District

The Winding Cypress Community Development District is an independent special district under Chapter 190 of the Florida Statutes. Collier County created it by Ordinance 2015-48, adopted September 9, 2015 and effective on filing September 10, 2015, over about 358 acres, which is the developed footprint of the community. Its district manager is Special District Services and its counsel is Kutak Rock, per the district’s website. It appears on the state’s official special district list and files its bond disclosures as an MSRB EMMA issuer.

Control of the district has moved to the residents in stages. DiVosta ran the 2022 landowner election, recorded in the February 7, 2023 board book; residents have held board seats since mid-2023, per the June 29, 2023 special meeting book; and Seats 1, 3 and 5 go to resident voters in the general election on November 3, 2026, per the Clerk’s 2026 qualifying period notice.

The district holds its budget hearing each summer. The fiscal 2026/27 budget was heard on July 23, 2026, per the Clerk’s legal notice and the hearing book, and its assessment is collected by the Collier County Tax Collector on the November tax bill, per the district’s FAQ page.

Who owns and maintains what in Winding Cypress

The division of duties follows the land. The district owns the lakes and most of the preserve tracts, which DiVosta deeded to it in October 2021 (Clerk record); the association owns the roads, the clubhouse on Tract G and the recreation and buffer tracts. In 2025 the association assigned the district its drainage and lake-maintenance easements on the Phase 2, Phase 2 Replat, Phase 2C and Phase 3 plats, recorded at Official Records Book 6441, Page 1629 (Clerk record), which put lake banks and their drainage under one owner.

The rules buyers ask about first

The rules that decide whether Winding Cypress fits a buyer’s plans are in the recorded Declaration and the 2026 Rules. In plain terms:

• Leasing: a minimum of 30 continuous days and a maximum of one year, no more than three leases in a calendar year, 30 days between lease start dates, whole home only, and Board approval required. Tenant screening runs through Tenant Evaluation, per the association’s lease and sale application flyer.
• Sales: the owner notifies the association at least 20 days before closing. The association cannot disapprove a sale; it records a Certificate of Approval for the buyer, as in this sample recorded certificate.
• Pets: up to three household pets; pit bulls, wolf hybrids and aggressive dogs are excluded; pets on a leash or carried; no invisible fences.
• Vehicles: boats, trailers, recreational vehicles, commercial vehicles, motorcycles and golf carts are kept in the garage; no overnight street parking. Golf carts must be registered with the association, insured, driven by a licensed driver and may not leave the community.
• Fences: tightly restricted and subject to architectural review; the current Rules allow only equipment screening. Above-ground pools are prohibited.
• Irrigation and signs: irrigation connects to the non-potable line, and signs, real estate signs included, need Board consent or Rules permission.
• Hurricane shutters: temporary shutters may go up no more than 72 hours before a storm and must come down within 72 hours after; an absent owner with permanently affixed shutters may keep them closed from June 1 to November 30, under the 2025 amendment.
• Architectural review: the reviewer has 60 days to respond, and the association may hold a refundable deposit of up to $5,000 on a project.

Two of these matter most in a sale. The three-leases-a-year cap and the 30-day minimum rule out short-term vacation rental, which protects the owner-occupied feel of the streets and narrows the investor pool. And the association’s inability to disapprove a sale means a closing date is set by the buyer, the seller and the lender, not by a board meeting calendar.

Is Winding Cypress age-restricted?

Winding Cypress is not age-restricted. It is an all-ages community under its recorded covenants: the Amended and Restated Declaration defines a household “Family” to include children and carries no age covenant. The age rules that do exist are amenity rules, not ownership rules: the fitness center bars anyone under 13 and requires residents aged 13 to 18 to be accompanied, per the May 2024 Rules.

What the association does not do

The Declaration expressly disclaims any obligation to provide security, so the accurate description of the entrance is a gated community with gatehouse attendants at the Collier Boulevard entrance, license-plate readers and a virtual callbox, not a security service. The association also does not run a bulk cable or internet contract: the 2026 budget carries a Cable line of $4,000 for the entire association, so owners contract television and internet service individually, per the 2026 Approved Budget.

Buying or Selling in Winding Cypress? Talk to the Team That Reads the Budget First

One association, one district and a 2026 assessment that fell about 1% from 2025 make Winding Cypress easier to underwrite than most East Naples communities, but only if the estoppel, the district line and the lease rules are in the file on day one. McGreevy and Comisar are Top 1% Real Estate Agents Nationally Since 2008, and we pull those documents before a listing goes live or an offer goes out. Selling? Start with a free Winding Cypress home valuation, or Call Jesse direct at (239) 898-6072. Buying? Call Marc at (239) 287-5873, or read how we represent buyers across Southwest Florida.

What Will You Actually Pay to Own a Home in Winding Cypress? (The Fee Stack)

Owning a Winding Cypress home in 2026 means an HOA assessment of $6,247.75 to $7,067.22 a year by series, a CDD assessment of $1,643.98 to $2,338.98 a year by product and phase, a $261.91 garbage charge and county property tax at 10.5058 mills. Buyers also pay a $1,050 capital contribution at closing.

Data updated: September 2026

Every figure below comes from a published primary document: the association’s 2026 Approved Budget (final October 29, 2025), the district’s fiscal 2026/27 Final Budget, the association’s 2025 audit and three real 2025 Collier County tax bills. Nothing here is an estimate from a listing.

The Winding Cypress fee stack at a glance

CDD figures are the gross budget amounts, before the 4% discount for paying the tax bill in November.

The HOA assessment by series, line by line

The association builds each home’s assessment from six components. Five are identical for every home; only the maintenance component, which pays for lawn care and irrigation, is priced by the front footage of the lot, which is why the three series pay different totals.

Source: Winding Cypress HOA 2026 Approved Budget. The 2026 assessment went down, not up: the Estate quarterly bill fell from $1,662.31 in 2025 to $1,645.80 in 2026, about 1.0% lower. That is a rare line in a Southwest Florida budget season and it is worth putting in front of any buyer comparing carrying costs.

What the HOA assessment covers, and what it does not

The assessment pays for the lawn and irrigation of every home, the common areas and their landscaping, the gatehouse and access control ($220,000 budgeted for vehicular access control in 2026), the clubhouse, pool, courts and fitness center, the on-site staff, the activities program and its events calendar, the Shady Palm Café subsidy and a reserve contribution. DiVosta’s own brochure listed the dues inclusions as community amenities, the activities director, lawn maintenance and irrigation, common-area maintenance and the gated entry.

It does not pay for golf (there is none), a security service (the Declaration disclaims one), bulk cable or internet (owners contract individually), homeowners or flood insurance, or the district’s assessment, which arrives separately on the tax bill.

The food-and-beverage minimum and the Shady Palm assessment

Two lines in the assessment exist because Winding Cypress runs its own restaurant. The Shady Palm component, $223.89 per home in 2026, and the food-and-beverage minimum, $484 per home in 2026 (included in the totals above), together fund the Shady Palm Café. The 2026 budget projects $790,000 of restaurant revenue and a planned net loss of $171,500 that those two lines cover, per the 2026 Approved Budget.

The minimum is a spend-it-or-lose-it credit, not a surcharge: owners draw it down on food and drink at the Shady Palm during the year. The recorded mechanism is the Declaration’s food-and-beverage section, amended by a corrective amendment at Official Records Book 6146, Page 1291; the amount owners are actually billed is the one the Board adopts in each year’s budget. The Board held a town hall on Shady Palm member cards and funding on July 7, 2026, per the approved town hall minutes, so a buyer should read the 2027 budget when it is adopted this fall.

The CDD assessment by product and phase

The district’s assessment has two parts: an operations and maintenance charge that every home pays equally, and a debt charge that repays the bonds that built the roads, drainage and utilities. The debt charge depends on two things, the product (villa, 50-foot or 65-foot homesite) and the assessment area (Phases 1 and 2, repaid by the Series 2015 bonds, or Phase 3, repaid by the Series 2019 bonds).

Source: Winding Cypress CDD fiscal 2026/27 Final Budget. Three of the five tiers appear exactly on real 2025 tax bills: $1,854.98, $1,643.98 and $2,223.98.

A Phase 3 home pays about $475 to $485 a year more district debt than a like-sized home in Phases 1 and 2 ($1,429 against $954 on a 50-foot homesite; $1,544 against $1,060 on a 65-foot homesite). The Phase 3 plat covers Pennyroyal Drive, Cocoplum Street, Greenbriar Court, Bromeliad Drive and the south end of Winding Cypress Drive. Assessment areas do not follow the plat lines perfectly: about 10 lots recorded on the Phase 2 family of plats carry Phase 3 (Series 2019) debt, so the tier for a specific address is read from its own tax bill, never from its street alone.

Why the CDD operations charge rose, and what it pays for now

The district’s operations and maintenance charge rose from $232.06 in fiscal 2022/23 (FY2022/23 budget) to about $795 in fiscal 2023/24 and has held at $794.98 since (FY2025/26 budget). The driver is the lake banks. The district’s engineer, LJA Engineering, assessed all 29 lakes in March 2024 (lake assessment), and the fiscal 2026/27 budget carries a $300,000 lake-bank remediation line and reports a lake-bank reserve of $366,062 as of July 1, 2026.

The practical reading for a buyer: the jump already happened, the charge has been flat for three budget years, and the district is funding the repair from a reserve rather than a special assessment. The district’s 2025 audit and its financials page carry the detail.

How long the CDD bonds run

The debt charge ends when the bonds do. On January 1, 2026 the Series 2015 bonds, which carry Phases 1 and 2, had $6,035,000 outstanding and mature in November 2045; the Series 2019 bonds, which carry Phase 3, had $3,940,000 outstanding and mature in November 2049, per the FY2026/27 budget and the recorded notices of special assessments for the Series 2015 and Series 2019 bonds. A handful of homes have prepaid their debt share; the district’s budget records the prepayments by assessment area, and a buyer can ask for a payoff figure through the closing agent.

Property taxes and three real Winding Cypress tax bills

Winding Cypress homes paid county property tax at 10.5058 mills on their 2025 bills, under Collier millage code 21, and the rate is identical across the two millage codes that split the community for administrative purposes. Greater Naples Fire Rescue District’s 2.0000 mills sits inside that total. Florida’s homestead exemption and its Save Our Homes cap apply to a primary residence, per the Florida Department of Revenue.

Three real 2025 bills, pulled from the Collier County Tax Collector, show what the whole stack looks like on paper:

Each of those bills carries exactly two non-ad valorem lines, the Winding Cypress CDD and District 1 Garbage at $261.91; no other county special assessment applies. The ad valorem part resets after a sale because the Save Our Homes cap does not transfer with the house (a portability credit may move with the seller), so a buyer should budget from the purchase price, not from the seller’s bill.

One-time costs at a Winding Cypress resale

The buyer pays the resale capital contribution at closing: $1,050 per resale in 2025, per the association’s 2025 audit, which also records 45 resales that year. The Declaration assigns the charge to the buyer and lets the Board set the amount each year. It goes into the association’s capital fund, not to the seller or the manager.

The estoppel certificate, the association’s statement of what is paid and owed, is capped by the state at $299, plus $119 for expedited delivery and more if the account is delinquent, under the DBPR fee schedule that implements section 720.30851 of the Florida Statutes. The association’s actual fee prints on the certificate itself. The Declaration also allows a transfer and lease application fee; its current amount is not in any public association document, so it appears in the application packet at the time of sale.

What a year costs before insurance and property tax

Adding the 2026 HOA total, the fiscal 2026/27 CDD total and the $261.91 garbage charge gives a fixed annual carrying cost for each product and phase, before property tax, insurance and utilities. The sums are our arithmetic on the published figures:

So the fixed cost of owning in Winding Cypress runs from about $8,150 to about $9,670 a year, or about $680 to $805 a month, before the property tax bill and the insurance premium. The villa sits at the bottom of that range; an Estate home on the Phase 3 plat sits at the top.

Special assessments

No HOA special assessment appears in the recorded documents or on the association’s public pages through September 2026; none was found in public records. The association funds replacements through its reserve line ($606.32 per home in 2026) against the Rimkus 2025 Reserve Study Update, and the district is funding its lake-bank work from its own reserve. The estoppel certificate for a specific home is the document that confirms, on the day of closing, that nothing further is owed.

What Types of Homes Make Up Winding Cypress, Including the Villas?

Winding Cypress has 766 homes in three DiVosta product lines: 152 attached villas in the Villa Series, 406 detached homes on 50-foot homesites in the Classic Series and 208 detached homes on 65-foot homesites in the Estate Series. Every home is fee-simple, built from 2015 to 2023 across five recorded plats.

Data updated: September 2026

There are no condominiums or apartments in Winding Cypress: every parcel is a fee-simple single-family lot on the county roll, attached villas included, per the Collier County parcel layer. The product counts come from the district’s unit census in its fiscal 2026/27 budget, and the series names are DiVosta’s own, from its Winding Cypress brochure.

Three series, 766 homes, one association

Sources: CDD FY2026/27 budget; HOA 2026 Approved Budget; DiVosta brochure.

The Southwest Florida MLS records the same split in its Building Design field, as “Single Family” or “Villa Attached”, and the market figures below use those labels exactly as listed. In the 12 months to September 23, 2026, the MLS recorded 35 single-family closings at a median of $875,000 and 13 villa closings at a median of $575,000 (Southwest Florida MLS data, pulled September 23, 2026).

The Villa Series: where the attached villas are

The 152 villas are fee-simple attached villas, built in pairs, with each owner holding title to the villa and its own small lot. They sit on two streets. Jacaranda Lane carries 110 of them across the Phase 2 and Phase 2 Replat plats (the street’s one detached home is 7673 Jacaranda Lane), and the 7093 to 7202 block of Live Oak Drive carries 40 more on the Phase One plat, per the county parcel layer; the district bills 152 villa units in its FY2026/27 budget. No villas were built on the Phase 3 plat.

Most villas went up from 2015 to 2019, the first years of the build. That timing puts them close to the clubhouse and the earliest-completed streets, and it puts a share of them on the preserve edge: 24 villa lots touch a recorded preserve tract, by our overlay of the county’s recorded lot and tract lines.

Villa prices: what the MLS shows

In the 12 months from September 24, 2025 to September 23, 2026, the Southwest Florida MLS recorded 13 villa closings in Winding Cypress:

Source: Southwest Florida MLS data, pulled September 23, 2026 (Building Design “Villa Attached”). The three lowest closings in the community over the year were all villas on Jacaranda Lane, at $455,000, $460,000 and $470,000.

The villa market has turned. The prior 12 months (September 2024 to September 2025) recorded 9 villa closings at a median of $560,000, so the median rose 2.7% to $575,000 and the median time on market fell from 107 days to 50. By calendar year, villa medians ran $710,000 in 2023 (11 closings, the peak), $610,000 in 2024 (11), $537,000 in 2025 (9) and $575,000 in 2026 through September 23 (11). The samples are small, a dozen sales a year, so one unusual closing moves a median; the direction across all three measures (price, days on market and volume) is still the same. On September 23, 2026 two villas were active, at $575,000 and $599,900, which is 1.8 months of villa supply against the trailing year’s pace.

The villa fee tier: HOA and CDD

The villa is the least expensive product to carry in Winding Cypress on both bills. Its 2026 HOA total is $6,247.75, $410.01 less than a Classic home and $819.47 less than an Estate home, because the lawn and irrigation component ($955.86) is priced by lot front footage, per the 2026 Approved Budget. Every other line, from the clubhouse to the reserves, is the same for a villa as for the largest Estate home, and so is the access: a villa owner pays for, and uses, the full amenity program.

On the tax bill, every villa sits in the Phases 1 and 2 assessment area and pays the district’s lowest debt tier, $849, for a total CDD charge of $1,643.98 in fiscal 2026/27, per the district budget. Add the garbage charge and the villa’s fixed carrying cost is about $8,153.64 a year before property tax and insurance. The one real villa bill we pulled, 7666 Jacaranda Lane’s 2025 bill, totalled $6,671.25 without a homestead exemption.

The Declaration also lets the association levy a separate Villa Assessment for costs that apply only to villas (Section 4.1(G)); the 2026 villa total above is the published figure, and the estoppel certificate for a specific villa lists every assessment that applies to it.

Villa maintenance, insurance and the shared wall

Owning an attached villa here is closer to owning a detached home than owning a condominium. Under Section 7.2 of the Amended and Restated Declaration, each villa owner maintains his or her own villa and must carry casualty insurance at full replacement value; the association may, but is not required to, take on villa maintenance. The Declaration adds party-wall, shared-roof and party-fence rules that govern how the two halves of a pair share repair costs and decisions. The association still mows and irrigates the villa’s lawn under the maintenance component of the assessment.

For a buyer, three documents matter at contract: the Declaration’s villa sections, the wind mitigation report on the villa (roof covering, roof-to-wall connection and opening protection drive the premium), and the neighbor’s side of the shared roof, because a roof on a paired villa is one system over two titles.

Who the villas suit

The Villa Series is the entry point to Winding Cypress. A villa buyer gets the same gate, clubhouse, clay courts, pool and restaurant as an Estate owner at about $300,000 less than the single-family median ($575,000 against $875,000 over the trailing 12 months), with the lowest HOA and CDD charges in the community and a 1,554-square-foot median living area that is simple to lock and leave. Buyers weighing a villa usually compare it with a detached Classic home on a 50-foot homesite; the trade is a shared wall and a smaller yard against roughly $300,000 of price and about $515 a year of fixed charges. Buyers who want a larger lot and room for their own pool land in the detached series instead.

The Classic Series: 406 homes on 50-foot homesites

The Classic Series is the largest product line in Winding Cypress, 406 detached homes on 50-foot-wide homesites, per the district’s unit census. DiVosta’s brochure lists the later Classic plans with their air-conditioned areas: Palmary, 1,943 to 2,063 sq ft; Prestige, 2,080 to 2,257 sq ft; Prosperity, 1,670 to 1,790 sq ft; and Mystique, 1,889 to 3,037 sq ft. Earlier releases sold under the Abbeyville, Martin Ray, Summerwood, Cressida and Infinity names, per DiVosta’s archived 2015 and 2019 community pages. The four newest plans were introduced in late 2020, per Florida Weekly.

A Classic home pays the middle HOA total, $6,657.76 for 2026, and a CDD charge of $1,748.98 in Phases 1 and 2 or $2,223.98 on the Phase 3 plat.

The Estate Series: 208 homes on 65-foot homesites

The Estate Series is 208 detached homes on 65-foot-wide homesites. Its plans, per the DiVosta brochure, are Pinnacle, 2,488 to 3,676 sq ft; Tangerly Oak, 2,589 to 2,938 sq ft; and Stonewater, 2,852 to 3,894 sq ft of air-conditioned area. The Estate specification added whole-house gutters and DiVosta’s “Tubes in the Wall” feature as standard. Estate homes carry the highest HOA total, $7,067.22 for 2026, and a CDD charge of $1,854.98 in Phases 1 and 2 or $2,338.98 in Phase 3.

The MLS does not separate Classic from Estate; both file as “Single Family”, and no public record classifies each lot by width, so the detached market is reported as one segment. Over the 12 months to September 23, 2026 that segment recorded 35 closings at a median of $875,000, a median of $405.92 per square foot of living area, a median living area of 2,158 sq ft, a 96.26% median sold-to-list and 76 median days on market, with sales from $575,000 to $1,495,000 (Southwest Florida MLS data, pulled September 23, 2026). The top of that range, $1,495,000 for 7412 Winding Cypress Drive on March 11, 2026, was a 3,656-square-foot home, the size band of the largest Estate plans.

Floor plans and what they first sold for

DiVosta opened pre-sales in December 2014 from a temporary sales center at Verona Walk, with prices from $263,990 to $419,990, per its archived December 2014 page. The Serenity design started at $263,990 that month and at $312,990 by July 2019; the Martin Ray started at $341,990 and $412,990 over the same dates, per the archived 2019 page. By December 2020 DiVosta was marketing its single-family homes “from the $400s to $700s,” per Florida Weekly. Those were base prices before lot premiums and options, and they are history, not today’s market; the MLS figures above are today’s market.

The five recorded plats

Sources: Collier County Clerk plat index; county parcel layer. The five plats sum to 766 homes. Phase One has the most preserve-edge homesites of any plat, 40 of the 70 lots that touch a recorded preserve tract; Phase 3 homes are the newest, built 2019 to 2023, and carry the higher Series 2019 district debt.

Street by street

Home counts: Collier County Property Appraiser records served through the county parcel layer; villa total per the CDD budget; closings: Southwest Florida MLS data, pulled September 23, 2026.

What the county roll says the homes are worth

On Collier County’s 2026 preliminary roll, the median county just value is $495,624 for an attached villa and $743,973 for a detached home, per Collier County Property Appraiser records served through the county parcel layer. County just value is an assessment figure for the tax roll, not a sale price, and it runs below what the same homes sell for on the MLS; the gap is one reason a new owner’s first tax bill is often higher than the seller’s.

What Is in The Club at Winding Cypress, and Do You Have to Join?

The Club at Winding Cypress is the community’s clubhouse and amenity campus at 7180 Winding Cypress Drive, built in 2016 and owned by the homeowners association. Membership is mandatory and bundled into the HOA assessment: there is no initiation fee, no equity, no separate club dues and no membership for non-residents.

Data updated: September 2026

“The Club at Winding Cypress” is DiVosta’s marketing name; the association and its Rules call the building the Amenity Center or the clubhouse. It sits on Tract G, a 6.61-acre association tract on the Phase One plat, per the county parcel layer, and the state roll dates it to 2016, per the Florida Department of Revenue cadastral file.

How big is the Winding Cypress clubhouse?

Two builders give two figures because they measured two things. DiVosta marketed a 17,500-square-foot clubhouse, per its archived 2016 community page. The general contractor that built it, DeAngelis Diamond, describes a 22,000-square-foot amenity center that takes in the clubhouse, catering kitchen, library, fitness center, aerobics studio, resort-style pool, spa, barefoot bar, bocce and tennis courts and walking trails, per its project page. The campus is several structures, each with its own roof in the association’s 2025 reserve study: the clubhouse, the pool bath house, the Shady Palm Café and the guardhouse.

The rooms inside

The 2026 Rules list the indoor rooms by their current names: the community event room and internet café, the library, the catering kitchen, men’s and women’s locker rooms, the fitness center with its Movement Room, and the HOA office, with complimentary Wi-Fi throughout. DiVosta’s brochure used older names for some of the same spaces, a ballroom, a card room and a lounge, and added an outdoor barefoot bar and grill, a natural-gas fire pit and an outdoor yoga deck. Outdoors, the 2026 inventory is the pool and cabana deck, the spa, fireplace and fire-pit areas, the Shady Palm Café, 4 clay tennis courts, 8 pickleball courts and 4 bocce courts.

Do you have to join, and what does membership cost?

There is nothing to join. Every owner is a member of the association by owning a home, and the amenities are funded inside the assessment, so the 2026 HOA totals of $6,247.75 (Villa), $6,657.76 (Classic) and $7,067.22 (Estate) are the whole cost of amenity access, food-and-beverage minimum included, per the 2026 Approved Budget. There is no equity club to buy into, no initiation fee at purchase (the $1,050 resale contribution goes to the association’s capital fund) and no tier of membership above the basic one.

The flip side is that the club is closed to outsiders. Amenity use is limited to owners, their tenants, their families and their guests; guests who do not live in the home must be accompanied; only owners may rent the rooms; and an owner must be in good standing with the association to use them, per the 2026 Rules. Access is by key fob: two are issued with the home and extras cost $25 each.

The staff and the budget behind the club

An activities director, a general manager and a maintenance supervisor work on site through Seacrest Southwest Property Management, and the Shady Palm has its own manager and chef, per the association’s contact page. DiVosta sold the community with a full-time activities director, and the position has stayed. The 2026 budget funds $220,000 for vehicular access control and a reserve contribution of $606.32 per home, and it records the 2025 work in the 2025 Year in Review: new pool heaters, three tennis courts resurfaced, all four bocce courts resurfaced, boardwalk repairs and an expanded pool deck.

Reserving a room

Owners can reserve the internet café, the event room, the catering kitchen, the Movement Room and the library through the activities director for a private event, under a rental agreement with fees, per the 2026 Rules. Hours for each amenity are posted in the HOA Rules and change with the season.

Does Winding Cypress Have a Golf Course?

Winding Cypress does not have a golf course. No golf appears in the association’s website, its 2026 Rules, its reserve study, DiVosta’s brochure or the contractor’s amenity-center page. The nearest golf is public: Lely Resort’s Mustang and Flamingo Island courses, about 7 minutes from the clubhouse, with no membership required.

Data updated: September 2026

Proven: no course inside the gates

The absence is documented five ways. The association’s website and amenities page, the 2026 Rules, the 2025 reserve study (which lists every component the association must eventually replace), DiVosta’s brochure and DeAngelis Diamond’s amenity-center page all describe the amenities without a golf course, a driving range or a putting green. Instead of fairways, about 818 acres of recorded preserve tracts surround the homes, per the county parcel layer.

That shapes the cost. Winding Cypress owners pay no golf dues, no golf capital charge and no food-and-beverage minimum tied to a golf club; the only minimum is the $484 Shady Palm credit.

The nearest golf courses

Lely Resort’s two public courses, the Mustang course by Lee Trevino and the Flamingo Island course by Robert Trent Jones Sr., are open to the public with “no membership required,” per Lely Resort Golf. They sit about 2.6 road miles and 7 minutes from the Winding Cypress clubhouse (OpenStreetMap routing without traffic, clubhouse origin; January to April adds time). A Winding Cypress golfer plays pay-as-you-go 36 holes minutes from home and keeps the club decision separate from the house decision.

Golf carts inside Winding Cypress

Golf carts are allowed on the community’s private roads but not beyond them. A cart must be registered with the association each year, insured, kept in the garage and driven by a licensed driver, and it may not leave the community, per the 2026 Rules and the Declaration.

How Far Is Winding Cypress From the Beach?

Winding Cypress is about 21 to 23 minutes from the nearest Gulf beaches without traffic: 11.1 miles and about 21 minutes to Naples Pier, and 11.4 miles and about 23 minutes to Tigertail Beach on Marco Island, measured from the Collier Boulevard gate. The Jolley Bridge onto Marco Island is 8.6 miles and about 14 minutes away.

Data updated: September 2026

“How far is Winding Cypress from the beach?” is the question Google surfaces most often for this community, so we measured it rather than estimating it. Every route below starts at the main gate, Winding Cypress Boulevard at Collier Boulevard, and uses the public OSRM routing engine on OpenStreetMap data, without traffic. From January to April, season adds time on Collier Boulevard and US 41.

Drive times from the gate to the beaches

Two routes, two beach styles. Naples Pier puts an owner on the city’s beach in Olde Naples, a few blocks from Fifth Avenue South (9.8 miles, about 18 minutes from the gate). Tigertail Beach on Marco Island is a county beach park with a lagoon and a wilder beach across it, per Collier County Parks.

Beach parking for Winding Cypress owners

Collier County property taxpayers and full-time residents qualify for a free annual beach parking permit that is valid at Collier County and City of Naples beach parking, per Collier County Parks’ beach parking page. Without the permit, Tigertail Beach charges $10 to park, per Collier County Parks. Winding Cypress owners pay Collier property tax, so the permit is part of the package with every home here, seasonal owners included.

Boating: no marina, and the lakes are off limits

Winding Cypress has no marina, no boat slips and no boating on its lakes. The 29 lakes are stormwater lakes owned by the Community Development District, and the 2026 Rules give residents “no recreational or other access (including but not limited to fishing and water toys)”; fishing, swimming and boating are not allowed. Boats and trailers must be kept in the garage under the Declaration.

Boaters trailer to the Gulf instead. The nearest public launch is the Collier Boulevard Park Boat Ramp, just north of the Marco Island bridge on Collier Boulevard, which reopened on August 13, 2025 after an upgrade with a new seawall, ramp and floating dock; launching costs $10 and parking is free with the Collier resident beach permit, per Collier County. Measured from the clubhouse, Marco Island’s Rose Marina is 11.0 miles and about 21 minutes, and Port of the Islands, on US 41 toward the Ten Thousand Islands, is 14.7 miles and about 23 minutes (OpenStreetMap routing without traffic, clubhouse origin).

Rookery Bay and Collier-Seminole State Park

The nearest water most owners use is not a beach at all. The Rookery Bay Environmental Learning Center is 2.3 miles and about 4 minutes from the gate, the front door of the Rookery Bay National Estuarine Research Reserve, which runs guided boat tours from the reserve, per Rookery Bay and the Florida Aquatic Preserves profile. Collier-Seminole State Park, 9.1 miles and about 16 minutes from the clubhouse, covers 7,271 acres with a boat ramp and a 13.5-mile canoe and kayak trail on the Blackwater River, per Florida State Parks.

How Many Pickleball and Tennis Courts Does Winding Cypress Have?

Winding Cypress has 4 Har-Tru clay tennis courts, 8 pickleball courts and 4 Har-Tru bocce courts under its 2026 Rules. The count changed in 2026, when the homeowners association converted a fifth clay tennis court into four asphalt pickleball courts after a Collier County Hearing Examiner appeal of the site plan was denied.

Data updated: September 2026

The courts sit beside the clubhouse on the association’s recreation tract, lighted, and are reserved and used under the court rules in the 2026 Rules. The association’s public amenities page still carries the older court count; the 2026 Rules are the current inventory.

Four clay tennis courts

The tennis courts are Har-Tru clay, a slower, softer surface than hard courts, and the association’s Clubs page describes “beautifully maintained clay courts.” A contractor maintains them five days a week, and in 2025 the association resurfaced three of the clay courts to fix drainage and added new canopies, per the 2025 Year in Review and the September 16, 2025 board minutes. The reserve study lists court lighting, fencing, a hydration system, shade structures and a grandstand seating area. The Tennis Club organizes play.

Eight pickleball courts, and how the count got there

Winding Cypress opened with four pickleball courts. In 2025 the Board took a proposal to convert clay tennis court 5 into four more, per the Pro Court conversion proposal. The site plan was appealed, and the Collier County Hearing Examiner heard the matter on March 13, 2026 (ADA-PL20260000118, per the Clerk’s legal notice); the appeal was denied, and the conversion went ahead in 2026, per the April 14, 2026 and May 19, 2026 board minutes. The 2026 Rules count 8 pickleball courts; the association has not published a completion date.

The conversion was not quiet: the 2025 and 2026 board minutes record a pre-suit mediation demand over it and a commissioned pickleball sound study. A buyer looking at a home near the courts should read those minutes. The Winding Cypress Pickleball Club charges $20 per person for 2026, per its membership form.

Four bocce courts

The four bocce courts are Har-Tru, all resurfaced in 2025, lighted on timers, with a storage shed added the same year, per the 2025 Year in Review. The Bocce Club runs league and social play.

More courts beyond the gates

For tournament-level pickleball, East Naples Community Park has 59 pickleball courts plus 6 championship courts and is the home of the US Open Pickleball Championships, per Collier County Parks. It is 7.0 miles and about 14 minutes from the Winding Cypress clubhouse (OpenStreetMap routing without traffic, clubhouse origin).

What Fitness, Pool and Walking Amenities Does Winding Cypress Offer?

Winding Cypress offers a heated resort-style pool with lap lanes, a spa with a waterfall and poolside cabanas, a fitness center with commercial Matrix equipment and a Movement Room for classes, two dog parks, a community garden and a wooden boardwalk to a sheltered preserve overlook. All are included in the HOA assessment.

Data updated: September 2026

The fitness and pool program is the most-used part of the amenity campus. The association’s certified 2025 Fitness Survey, answered by 360 of 766 households in October 2025, found the most common gym time to be 8 a.m. to noon (36.4% of respondents) and 45.2% of full-time respondents using the gym more than eight times a month.

The pool and spa

The pool is one heated resort-style pool with lap lanes, not a separate lap pool, with a spa and cascading waterfall, lounge chairs and cabanas, per the association’s amenities page and the DiVosta brochure. The pool heaters were replaced in 2025 and a sand area was paved to widen the pool deck the same year, per the 2025 Year in Review. There is no lifeguard; a lap lane is kept open for swimmers, children 12 and under need adult supervision and every visitor is accompanied by a resident, per the 2026 Rules.

The fitness center and Movement Room

The fitness center is equipped with Matrix commercial treadmills, ellipticals, cycles, a leg press, a Smith machine, benches and free weights, per the component inventory in the 2025 reserve study, and the Board kept adding equipment in 2026, per the June 16, 2026 minutes. The Movement Room next door hosts fitness and dance classes, chair yoga among them. The fitness center is limited to residents 13 and older, with those 13 to 18 accompanied by a resident. There is no day spa or massage business on site; “spa” at Winding Cypress means the heated spa beside the pool.

The boardwalk, dog parks, garden and walking path

The quiet amenities are the ones that make Winding Cypress feel like a preserve community. A wooden boardwalk runs through the preserved landscape to a sheltered overlook, and there is a separate bird wading overlook; the boardwalk closes at sunset and entry into the preserve itself is not allowed at any time, per the amenities page. Repairs on the boardwalk’s east side were completed in 2025 and the west side followed.

Dog owners get two dog parks, one for small dogs and one for large, refurbished with new benches, pavers, tables and umbrellas in 2025 and 2026. The Garden Club tends an organic community garden with individual plots, and a walking path runs through the community. Beyond the gates, the Picayune Strand State Forest lies about 140 meters from 7478 Winding Cypress Drive, per the Florida Natural Areas Inventory conservation lands layer; its public trails are reached by road, per the Florida Forest Service.

Where Can You Eat Inside Winding Cypress?

Inside Winding Cypress you eat at the Shady Palm Café, a poolside bar and restaurant run by the homeowners association with its own manager and chef, open to residents and their guests. Every home funds it through a $223.89 Shady Palm assessment and a $484 food-and-beverage minimum in 2026.

Data updated: September 2026

A resident-only restaurant is uncommon in a community without golf, and the Shady Palm is the center of Winding Cypress social life: happy hours, live entertainment nights and themed specials run through it, per the association’s April 2026 community update.

The Shady Palm Café

The Shady Palm is a separate building on the amenity campus with its own roof and kitchen equipment in the reserve study. It serves lunch and dinner by the pool with a full bar, closes two days a week in summer, runs a daily happy hour and books entertainment on Wednesdays and set weekends; current hours are posted by the association on its amenities page. It serves residents and their guests only and is not available for private catering, per the 2026 Rules. The association hired a new restaurant general manager and added televisions and entertainment wiring in 2025, per the 2025 Year in Review.

How the Shady Palm is funded

The café runs as its own fund inside the association budget. For 2026 it budgets $790,000 of revenue ($450,000 food, $170,000 liquor, $75,000 beer, $75,000 wine and $20,000 non-alcoholic drinks) and a planned net loss of $171,500, which the Shady Palm assessment and the food-and-beverage minimum cover, per the 2026 Approved Budget. The $484 minimum is credit an owner spends at the café during the year. The funding model was the subject of a July 7, 2026 town hall, per the approved minutes.

Groceries and restaurants outside the gates

Freedom Square, at US 41 and Collier Boulevard, is 1.7 miles and about 4 minutes from the gate, with a Publix, Burlington and HomeGoods, per its owner Brixmor, and a row of restaurants along its frontage. A second Publix at 8585 Collier Boulevard is 2.6 miles and about 5 minutes north. The restaurants of Fifth Avenue South in Olde Naples are 9.8 miles and about 18 minutes away (OpenStreetMap routing without traffic, from the gate).

What Clubs, Classes and Events Happen in Winding Cypress?

Winding Cypress runs a full-time activities program through an on-site activities director, with official clubs for pickleball, tennis, bocce, books, gardening, crafts, water aerobics, cards and games and Corvettes, plus a season calendar of pool-deck dance parties, DJ afternoons, karaoke, a holiday craft fair, Oktoberfest and a ticketed season-end party.

Data updated: September 2026

The program is funded inside the HOA assessment, organized by the activities director with a resident Events and Activities Committee, and it is busiest in season, when part-time owners are in residence.

The official clubs

The association’s Clubs page lists the resident clubs:

• Pickleball Club, $20 per person for 2026 (membership form)
• Tennis Club, on the four clay courts
• Bocce Club, on the four Har-Tru bocce courts
• Book Club, meeting monthly in the Amenity Center event room
• Garden Club, which tends the community garden plots
• Chatty Crafters, meeting weekly in the internet café
• Water Aerobics, in the resort pool up to six days a week
• Cards and Games, with Samba, Hand-Foot-Elbow, Bunco, Mahjong and poker
• Corvette Club

Clubs book their rooms and courts through the activities director, and owners can reserve the event room, internet café, catering kitchen, Movement Room and library for private events under a rental agreement, per the 2026 Rules.

A sample Winding Cypress season

The association’s weekly community update for the week ending April 10, 2026 (newsletter) shows what the end of a season looks like: a dance party on the pool deck, DJ afternoons at the Shady Palm, a live band, a karaoke night, themed food specials and a ticketed Farewell Party to close the season. Earlier in the year the calendar carried a Holiday Craft Fair in the event room, Oktoberfest at the Shady Palm, a community blood drive, food trucks, art classes and a group trip to spring training, per the 2025 Year in Review and the September 16, 2025 board minutes.

Full-time and seasonal owners

The calendar follows the residents. In the association’s certified October 2025 survey, 56.3% of responding households said they live in Winding Cypress full time and 43.7% part time, with 360 of 766 households answering; among part-time owners, 51.8% stay four to six months, 29.3% seven to eight months and 18.9% up to three months, per the 2025 survey results.

Nature, wildlife and the preserve next door

Some of the best-known Winding Cypress moments are not on any calendar. The community backs onto the Picayune Strand, whose state forest and wildlife management area are home to Florida panthers, black bears, wood storks and red-cockaded woodpeckers, per the Florida Fish and Wildlife Conservation Commission. A family of four black bears was filmed walking through Winding Cypress in January 2025, per WINK News. The Florida Forest Service manages the forest with prescribed burns, and the association posts the county’s planned-burn map for owners each year (2026 planned burns).

Ready to Live the Winding Cypress Calendar, or Hand It to the Next Owner?

Winding Cypress sells on its amenity program: 8 pickleball courts, 4 clay tennis courts, a resident-only restaurant and a full-time activities director, with no club to buy into. We price and market Winding Cypress homes around exactly that. Selling? Get a free Winding Cypress home valuation, or Call Jesse direct at (239) 898-6072, text or call. Buying? Call Marc at (239) 287-5873 before the season’s listings go live, or see how McGreevy and Comisar represent buyers.

How Storm-Ready Is Winding Cypress?

Winding Cypress homes were built from 2015 to 2023 in steel-reinforced concrete block, with engineered roof trusses, hurricane tie-downs and galvanized steel shutters as the builder standard. The community sits in Collier County Evacuation Zone D, landward of US 41, and its district recorded no significant damage after Hurricane Ian.

Data updated: September 2026

Storm readiness in Winding Cypress is a record question, not a feeling. The public record gives us four things to measure: how the homes were built and under which code, which evacuation zone the county assigns, what the National Hurricane Center’s surge model shows street by street, and what actually happened here in Irma, Ian, Helene and Milton. We walk through each below, and the flood-map and insurance sections that follow pick up the same thread.

How the homes were built

DiVosta’s own specification sheet for Winding Cypress lists “steel-reinforced concrete block construction,” “professionally engineered roof trusses with hurricane tie-downs for wind protection,” a tile roof, and “galvanized steel hurricane shutters” as standard, with “optional impact glass available” (DiVosta Winding Cypress digital brochure). The same brochure lists double-pane, low-E windows and roof underlayment placed where leaks are most likely. DiVosta, a PulteGroup brand, backs its homes with a 10-year limited structural warranty (The DiVosta Promise); the earliest Winding Cypress homes, closed in 2015, are now past that window, and the newest, closed in 2023, still have part of it left.

One caution matters for a resale buyer. The brochure we read is the closeout-era edition, so it describes the standard spec late in the build. Which openings on a particular home carry shutters and which carry impact glass is recorded, home by home, on its wind mitigation report (form OIR-B1-1802), not in any community-wide document. Ask for that report before you write an offer; it also drives the insurance discounts covered below.

The building-code era of Winding Cypress homes

Florida’s building code changed twice while Winding Cypress was going up. According to the Florida Building Commission’s effective-dates sheet, the 2010 Florida Building Code took effect March 15, 2012; the 5th Edition (2014) took effect June 30, 2015; and the 6th Edition (2017) took effect December 31, 2017. The permits recorded on Winding Cypress Elevation Certificates run from 2014 to 2019 (Collier County Elevation Certificates layer), so the earliest Phase One homes were permitted under the 2010 code, most Phase One and Phase 2 homes under the 5th Edition, and the Phase 3 homes permitted in 2018 and 2019 under the 6th Edition. The code in force is set by the permit application date, which each home’s permit file shows.

Every Winding Cypress home is therefore a post-2012 Florida Building Code home. That is the whole reason several older-home insurance hurdles, from the four-point inspection to the roof-age rules, do not apply here yet. We do not publish a design wind speed for the community: no site-specific code record for these permits was retrieved, and a contour estimate is not a substitute for the number on a permit.

Evacuation Zone D, and what that means in practice

Collier County’s Hurricane Evacuation Zone layer (last edited August 20, 2026) places every one of the 13 Winding Cypress addresses we sampled, from Live Oak Drive in Phase One to Bromeliad Drive in Phase 3, in Evacuation Zone D. Zone C begins about a kilometer west, near Collier Boulevard. Anyone can check a single address in the county’s evacuation zone lookup.

Collier County orders evacuations by zone letter, and the recent record is useful. Before Hurricane Ian in 2022 the mandatory order covered Zone A, the coastal area, per the National Weather Service Miami Ian summary. Before Hurricane Milton in 2024 the orders covered Zones A and B (NWS Miami Milton impact narratives). Zone D, and so Winding Cypress, was not ordered out in either storm. In practice that means a Winding Cypress owner should listen for “Zone D” by name; an order for Zones A, B or C does not reach these streets, even though Zone C starts just west of the entrance.

When leaving is the right call, the route out is short on paper: I-75 at Exit 101 is 6.1 miles and about 11 minutes from the Collier Boulevard gate without traffic, measured with OpenStreetMap routing (OSRM route engine). Evacuation traffic is a different animal, so seasonal owners who leave before a storm season usually make their plans in June, not in the week of a watch.

Storm surge scenarios by street

Evacuation Zone D and “no surge” are not the same thing, and we would rather show you the model than soften it. The National Hurricane Center’s National Storm Surge Risk Maps model a near-worst-case hurricane arriving at high tide for each category. We read those maps at 13 Winding Cypress addresses:

Three honest readings follow from that table. First, the south-west Phase 3 streets, which sit closest to US 41 and the coastal flood area, are the first to show modeled surge, beginning at Category 1. Second, most of the community shows surge from Category 2, and every sampled street shows it from Category 3. Third, these maps are planning scenarios that assume the worst track at the worst tide; they are not a forecast, and they are not a history. The surveyed floor heights in the flood section below are the numbers that set how a particular house relates to water.

Hurricane Irma, 2017

Irma came ashore almost next door. The National Hurricane Center’s Tropical Cyclone Report on Irma records that “Irma made its final landfall near Marco Island, Florida, at 1930 UTC 10 September,” and that “the Naples Municipal Airport reported a 123-kt wind gust.” Across Collier County, the report states, at least 88 buildings were destroyed and 1,500 badly damaged. Winding Cypress was only partly built in September 2017: Phase One homes had been certified in 2015 and Phase 2 permits were still issuing through 2016 and 2017.

The federal flood-claim record for the area is thin. FEMA’s OpenFEMA NFIP claims data shows three flood insurance claims in the Census block group that contains Winding Cypress, all from Irma, and none of the three was paid. That block group covers about 25.8 square kilometers against the community’s roughly 4.8, so it includes older neighborhoods too, and the three claims cannot all be read as Winding Cypress homes.

Hurricane Ian, 2022

Ian was the surge storm for Collier County. The NHC’s Tropical Cyclone Report on Ian states that “Maximum inundation of 6 to 9 ft AGL occurred in Naples” and that “The NOS tide gauge on Naples Pier measured 6.18 ft above MHHW before the station was destroyed.” The NWS Miami Ian summary places the heavy surge flooding in Collier “south/west of Tamiami Trail/US 41,” which is the coastal side of the road; Winding Cypress sits on the landward, north-east side of US 41.

Inside the gates, the record is the district’s. The Winding Cypress Community Development District’s November 1, 2022 minutes record the line we quote exactly: “No significant damage was noted by the community” (CDD board meeting book, February 7, 2023, holding the November 2022 minutes). The OpenFEMA claims file shows zero Ian flood claims in the Census block group, while ZIP 34114 as a whole logged 146 Ian claims, most of them in older coastal neighborhoods.

Helene and Milton, 2024

The 2024 season brought two storms close. The NHC’s Tropical Cyclone Report on Milton records “Maximum storm surge inundation of 3-5 ft AGL” from Bonita Beach through Marco Island, and the NWS Miami Milton narratives estimate that about 85 percent of Collier County customers lost power. The OpenFEMA claims file shows no Helene or Milton flood claims in the Winding Cypress block group. No news report we found names Winding Cypress in damage coverage for either storm.

What the Declaration says about shutters and storm season

The association’s rules anticipate storm season in writing. A Certificate of Amendment recorded September 12, 2025 (Official Records Book 6507, Page 955) rewrote the shutter section of the Declaration: temporary shutters may go up no more than 72 hours before a storm and must come down within 72 hours after it, while owners who are away for the season and have permanently affixed shutters may keep them closed from June 1 to November 30. New permanent shutters and impact-glass changes still go through architectural review under the Amended and Restated Declaration.

For a seasonal owner, that amendment is the practical rule of the whole section: close up in June if you leave, keep the fob and gate app current for anyone checking the house, and keep the home’s wind mitigation report, elevation certificate and any FEMA letter in one folder. Those three documents answer most of the questions a buyer, an insurer or an adjuster will ask later.

What Flood Zone Is Winding Cypress In?

Winding Cypress is in FEMA flood Zone AE on the flood map effective February 8, 2024, at every address we sampled, with a base flood elevation of 8.0 feet NAVD88. About 15 homes hold their own FEMA letters moving the lot or house to shaded Zone X, so check each address before assuming.

Data updated: September 2026

The short answer surprises buyers who read older listing remarks, because for several years the whole community was treated differently. The builder-era map changes from 2015 to 2019 no longer carry over to the current map, and the flood zone that matters today is the one on the 2024 map, lot by lot. Here is the record.

The 2024 flood map for Winding Cypress

The map is Collier County’s (community number 120067). FEMA’s National Flood Hazard Layer panel index shows Winding Cypress on four panels, 12021C0604J, 12021C0608J, 12021C0612J and 12021C0616J, all effective February 8, 2024. Collier County confirms the date in its 311 knowledge base and its 2026 Floodplain Protection Newsletter.

On FEMA’s flood hazard zones layer, all 13 addresses we sampled across the five plats return Zone AE, a high-risk Special Flood Hazard Area with a base flood elevation. FEMA’s Letter of Map Revision layer shows no community-wide map revision in effect.

Base flood elevation: 8.0 feet NAVD88

The base flood elevation, or BFE, is the height FEMA expects the 1-percent-annual-chance flood to reach. On FEMA’s BFE lines layer, the line nearest every sampled Winding Cypress address carries 8.0 feet NAVD88. That single number is the benchmark every elevation certificate in the community is measured against, and it is the number to hold up against a home’s surveyed floor height.

Flood zone by street and phase

Every sampled address, by street and recorded plat, with the FIRM panel and the National Hurricane Center’s modeled surge at Category 1 and Category 3 (FEMA flood zones, FEMA panels, NHC surge maps):

*At 7626 Arrowhead Way and 7666 Jacaranda Ln the flood-zone polygon also carries a static elevation value of 7.0 feet; the mapped BFE line nearest both addresses is 8.0 feet. Chenille Court and Wiregrass Court were not in the sample, so we do not assign them a zone here; check those addresses individually.

The pattern lines up with the storm section above. The whole community is AE, the south-west Phase 3 streets see modeled surge first, and Phase One, Phase 2 and Phase 2C streets sit a step further from the coastal flood area.

Why the builder-era map letters no longer count

Between 2015 and 2019, DiVosta obtained phase-wide Letters of Map Revision based on Fill (LOMR-F) that removed whole phases from the flood zone on the older 2012 map. One example is Case 15-04-9413A for Phase One lots 1 to 138 (FEMA LOMR-F 15-04-9413A); another is Case 19-04-5181A for most of Phase 3 (FEMA LOMR-F 19-04-5181A).

When the 2024 coastal restudy produced the current map, FEMA’s own layer marked those phase-wide letters “Superseded” or “Not incorporated” (FEMA LOMA and LOMR-F layer). In plain terms, the community went back inside the Special Flood Hazard Area on February 8, 2024, and a listing remark written from the old letters is out of date. That is why we never describe Winding Cypress as outside the flood zone.

Single-lot FEMA letters since 2024

Owners have responded lot by lot. Since the 2024 map took effect, FEMA has issued 16 single-lot LOMR-F determinations covering 15 homes in Winding Cypress, each moving a lot or a structure to shaded Zone X, a moderate-risk area outside the Special Flood Hazard Area (FEMA LOMA and LOMR-F layer). They cluster on two streets: Live Oak Drive in Phase One and Cocoplum Street in Phase 3. The most recent we read, Case 26-04-3737A dated June 24, 2026, covers a Live Oak Drive lot and supersedes that lot’s 2015 determination (FEMA LOMR-F 26-04-3737A).

Every one of these letters carries the same caution: the federal mandatory purchase requirement no longer applies to the lot or structure, but the lender “has the option to continue the flood insurance requirement.” For a buyer, the practical step is simple: ask the seller whether the home has a post-2024 FEMA letter, get a copy, and put it in front of your lender and your insurance agent in the first week of the contract.

Surveyed floor heights: what the elevation certificates show

An elevation certificate is a surveyor’s record of a house’s floor height against the flood map. Two Winding Cypress certificates we read in full bracket the community:

The Live Oak Drive certificate is public in the county’s own file (Elevation Certificate, 7093 Live Oak Dr). Across the certificates we reviewed, finished floors run from about 9.4 to 10.7 feet NAVD88, roughly 1.4 to 2.7 feet above the 8.0-foot BFE (our arithmetic). That margin is the reason flood premiums on newer homes in this area are modest, as the insurance section shows.

230 elevation certificates on file with Collier County

Collier County’s Elevation Certificates layer holds 230 certificates on Winding Cypress streets, filed with permits from 2014 to 2019: Live Oak Drive 78, Jacaranda Lane 36, Winding Cypress Drive 34, Mockingbird Court 22, Lily Way 16, Blackberry Drive 15, Chenille Court 9, Clamshell Lane 8, Cocoplum Street 5, Wiregrass Court 4 and Geranium Way 2. The later Phase 3 streets, Pennyroyal Drive, Greenbriar Court and Bromeliad Drive, and Arrowhead Way in Phase 2 do not appear in that layer; for those homes the certificate is usually in the builder’s closing package or can be requested from the county’s floodplain staff. The county’s floodplain hotline is (239) 252-2942, per its 2026 Floodplain Protection Newsletter.

Collier County’s Community Rating System class

Unincorporated Collier County is a Class 5 community in FEMA’s Community Rating System, which earns flood policies inside the Special Flood Hazard Area a 25 percent discount and policies outside it 10 percent, per FEMA’s NFIP Community Status Book and the county’s 2025 Floodplain Protection Newsletter. Winding Cypress homes, being Zone AE, sit in the 25 percent tier unless a FEMA letter has moved them out.

How to check a specific Winding Cypress home

For any address, four documents settle the question. The FIRMette for the address from FEMA’s map service shows the zone and panel. The home’s elevation certificate shows the floor height. Any post-2024 LOMR-F letter shows whether the lot or structure is out of the high-risk area. And the seller’s Florida flood disclosure, covered in the insurance section, states known flooding and past flood claims. We pull all four at the start of every Winding Cypress transaction, so a buyer’s lender and insurer see the same file the listing side does.

What Should You Know About Insuring a Home in Winding Cypress?

Insuring a Winding Cypress home turns on three records: the Zone AE flood map and any FEMA letter for the lot, the home’s elevation certificate, and its wind mitigation report. Newer single-family homes in this Census block group paid a median of about $1,270 for NFIP flood coverage on 2026 terms.

Data updated: September 2026

No public record prices a homeowners policy for a specific Winding Cypress address, and we will not guess one. What the record does show is how flood rules apply here, what flood policies nearby have cost, what Florida’s largest insurer charges on average in Collier County, and which inspections a buyer will and will not be asked for. Those are the numbers below.

Flood insurance and what your lender may require

Because Winding Cypress is Zone AE on the 2024 map, a lender making a federally backed mortgage will require flood insurance on most homes. There are two situations a buyer can be in:

1. The home has no post-2024 FEMA letter. It is rated in Zone AE, the lender requires a flood policy, and the elevation certificate drives the rate.
2. The home has a single-lot LOMR-F moving it to shaded Zone X. The federal mandatory purchase requirement no longer applies to that lot or structure, but, in FEMA’s words on every such letter, the lender “has the option to continue the flood insurance requirement” (FEMA LOMR-F 26-04-3737A).

Either way, many Winding Cypress owners keep a flood policy voluntarily, because the rate for a home with good floor elevation is modest and the model in the storm section shows surge reaching every street in a major hurricane.

What NFIP flood policies cost nearby

FEMA publishes anonymized policy data by Census block group. In the block group that contains Winding Cypress, 2026-term National Flood Insurance Program policies on single-family homes built 2014 to 2021 had a median cost of about $1,267 for homes rated Zone AE (37 policies) and $1,266 for homes rated Zone X (76 policies); the middle half of the AE policies ran from about $1,235 to $3,053 (OpenFEMA NFIP Policies). The median building coverage was $250,000, the NFIP maximum for a home.

Read those figures carefully. They describe newer single-family homes in this Census block group, which is larger than Winding Cypress and includes other subdivisions; they are not quotes for Winding Cypress homes. Under FEMA’s Risk Rating 2.0, a home’s first-floor height and its cost to rebuild weigh more than the zone letter, which is why the AE and X medians sit almost on top of each other here.

Citizens and the flood-coverage requirement

Citizens Property Insurance Corporation, the state-created insurer of last resort, now requires flood coverage on its wind policies in stages. Policies with wind coverage on homes in a Special Flood Hazard Area must carry flood insurance (Citizens, flood insurance coverage rules). Because Winding Cypress is Zone AE, that requirement applies to a Citizens policyholder here unless the lot has its own FEMA letter moving it out of the high-risk area.

Citizens rates in Collier County for 2026

Citizens’ 2026 Rate Kit shows Collier County averages moving in different directions by product:

These are county averages across every home age and value, not Winding Cypress quotes. A 2015 to 2023 concrete block home with shutters or impact glass and a documented wind mitigation report generally shops differently from the county average, which is exactly why the reports below matter.

Wind mitigation reports

A wind mitigation inspection on the state form OIR-B1-1802 documents the roof covering, roof-deck attachment, roof-to-wall connection, roof shape and opening protection that Florida insurers must consider for credits. The Florida Office of Insurance Regulation’s wind mitigation resources note that a report is valid for up to five years, and a new version of the form took effect April 1, 2026. For a Winding Cypress home, the report is where the hurricane tie-downs, the tile roof and the shutters or impact glass from the builder’s spec get recorded as insurable features.

Four-point and roof inspections

Citizens’ inspection rules require a four-point inspection (roof, electrical, plumbing, heating and air) for homes more than 20 years old. The oldest Winding Cypress homes, finished in 2015, reach that age from about 2034 (our arithmetic). Tile roofs need proof of at least five years of remaining life only after 50 years under the same rules, so the roof-age rule is not a factor in Winding Cypress today. Some private carriers set their own inspection rules, so ask your agent before you bind.

My Safe Florida Home grants

The state’s hardening grant program is not a lever here. My Safe Florida Home grants require a home built before January 1, 2008, and every Winding Cypress home was built from 2015 onward. The value in these homes comes from what DiVosta built in, not from retrofits.

The Florida flood disclosure

Since October 1, 2025, Florida law requires a seller of residential property to disclose known flooding, flood insurance claims and federal flood assistance received on the home, at or before the contract. The Florida Senate staff analysis of CS/CS/HB 1049 (2024) explains the requirement, created as section 689.302 of the Florida Statutes. A Winding Cypress seller who has a clean claims history and an elevation certificate in hand should lead with both; a buyer should read the disclosure next to the FEMA map, not instead of it.

The documents to gather before closing

Selling a Winding Cypress home and want the flood and wind file ready before the first showing? Get a free Winding Cypress home valuation, or Call Jesse direct at (239) 898-6072. Buying, and want the elevation certificate and any FEMA letter in front of your lender on day one? Call Marc at (239) 287-5873, or read how we represent buyers in Winding Cypress.

Which Schools Serve Winding Cypress?

Winding Cypress is zoned for Lely Elementary, Manatee Middle and Lely High for 2026-27, per Collier County Public Schools’ own address lookup, which returned the same three schools for all 774 address points on the community’s streets. Lely Elementary and Manatee Middle earned an A in 2026; Lely High earned a B.

Data updated: September 2026

A note for the many Winding Cypress owners without school-age children: the zoned schools still matter at resale, because families shopping East Naples filter by them. The assignment below comes from the district’s own tool, address by address, not from proximity or a rating website.

Zoned schools, address by address

We ran every address point on the 13 interior streets the district’s system lists for Winding Cypress, 774 in all, plus 13 sample addresses, through the lookup behind Collier County Public Schools’ zoning tool for the 2026-27 school year (CCPS address lookup, 2026-27). Every one returned the same three schools, with no rezoning flag, and the 2025-26 lookup returned the same three.

Grades are from the Florida Department of Education’s 2026 school grades file; Lely High’s enrollment is from the NCES Common Core of Data; drive times are OpenStreetMap routing from the Collier Boulevard gate without traffic.

Lely Elementary School

Lely Elementary serves pre-kindergarten through fifth grade at 8125 Lely Cultural Parkway, with 499 students in 2024-25 (CCPS school profile). It earned an A in each of 2024, 2025 and 2026 on the state’s grades, with 67 percent of possible points in 2026 (FLDOE 2026 grades). It is about 4 minutes from the Winding Cypress gate.

Manatee Middle School

Manatee Middle serves grades 6 to 8 at 1920 Manatee Road, in the same 34114 ZIP code as Winding Cypress, with 781 students in 2024-25 (CCPS school profile). It earned a B in 2024, then an A in 2025 and 2026.

Lely High School

Lely High serves grades 9 to 12 at 1 Lely High School Boulevard, with 1,475 students in 2024-25 (NCES). It earned a B in 2026 after an A in 2025. The school’s curriculum page lists Cambridge AICE courses, Advanced Placement with the AP Capstone option, dual enrollment with Florida SouthWestern State College, the FGCU collegiate high school option for juniors and seniors, and an Embry-Riddle aviation and drone dual-enrollment program; the district profile lists career academies in Criminal Justice, Engineering, Information Technology, Medical and Aviation. Lely High does not offer the International Baccalaureate.

Why Manatee Elementary is not on this list

Manatee Elementary is the closest elementary campus to Winding Cypress, which is why older builder materials and some websites list it. The district’s own 2026-27 lookup does not assign it to any Winding Cypress address. Zoning follows the district’s boundary, not the shortest drive, so we publish the lookup result.

School choice and out-of-zone requests

Collier County runs controlled open enrollment. For 2026-27 the district’s priority windows have closed, but out-of-zone and school-choice seats are still available by application, and the district accepts a fully executed purchase contract as proof of a move into a zone (CCPS Parental Choice). That matters for families buying in Winding Cypress mid-year: the contract, not the closing, starts the paperwork.

Charter schools within a reasonable drive

Tuition-free public charter schools add options. On the state’s 2026 grades file, Marco Island Academy, a charter high school at 2255 San Marco Road on Marco Island, earned an A in 2024, 2025 and 2026, and it is about 12.7 miles and 23 minutes from the Winding Cypress gate without traffic (Marco Island Academy). Marco Island Charter Middle School also earned an A in all three years. Charter admission is by application or lottery at each school.

Private schools

Several private schools sit within about 25 minutes. Tuition below is each school’s own published 2026-27 figure:

In season, January to April, the drives north on Collier Boulevard, Davis Boulevard and Livingston Road take noticeably longer than these free-flow times.

Colleges nearby

Florida SouthWestern State College’s Collier Campus, at 7505 Grand Lely Drive, is about 2.5 miles and 5 minutes from the Winding Cypress gate, and it is Lely High’s dual-enrollment partner. Florida Gulf Coast University’s main campus in Fort Myers is about 30.4 miles and 40 minutes away by I-75.

Where Is the Nearest Hospital to Winding Cypress?

The nearest hospital to Winding Cypress is Physicians Regional Medical Center, Collier Boulevard, at 8300 Collier Boulevard: 2.2 miles and about 3 minutes from the gate without traffic, with a 24-hour emergency room and 130 licensed beds. The region’s Level II trauma center is Gulf Coast Medical Center in Fort Myers, about 50 minutes away.

Data updated: September 2026

Healthcare is one of the quiet strengths of the Winding Cypress location. A full hospital and a walk-in clinic are each about 3 minutes away, and both of Naples’ larger hospital campuses are within half an hour. Licensed bed counts and state program designations below come from the Florida Agency for Health Care Administration’s Florida Health Finder, the state licensure record.

Physicians Regional Medical Center, Collier Boulevard

Physicians Regional’s Collier Boulevard hospital holds 130 licensed acute beds and AHCA listings as a Primary Stroke Center and for Level 1 Adult Cardiovascular Services, with an emergency department (AHCA Florida Health Finder). The hospital’s own page describes a 24-hour ER, an ACC-accredited Chest Pain Center, and outpatient radiology, laboratory, rehabilitation, wound care and hyperbaric medicine on the campus (Physicians Regional, Collier Boulevard). From the Winding Cypress gate it is 2.2 miles, about 3 minutes, north on Collier Boulevard.

Walk-in and urgent care

For the sprained ankle and the Saturday fever, NCH Medical Group Immediate Care Southeast, at 7717 Collier Boulevard, is 1.7 miles and about 3 minutes from the gate and open every day. The same NCH Southeast cluster on Collier Boulevard houses imaging, outpatient therapy and cardiology offices, which keeps most routine appointments within a few minutes of home.

NCH Baker Hospital, downtown Naples

NCH Baker Hospital, at 350 7th Street North, holds 391 licensed beds and AHCA listings as a Comprehensive Stroke Center with Level 2 Adult Cardiovascular Services (AHCA Florida Health Finder). It is about 10.7 miles and 20 minutes from the Winding Cypress gate without traffic, by Collier Boulevard and US 41.

Physicians Regional Pine Ridge

Physicians Regional’s Pine Ridge hospital, at 6101 Pine Ridge Road, carries AHCA listings as a Comprehensive Stroke Center with Level 2 Adult Cardiovascular Services (AHCA Florida Health Finder). It is about 12.2 miles and 18 minutes from the gate by I-75, often the quicker run to a higher-level cardiac or stroke program than downtown in season.

NCH North Naples and pediatric emergencies

NCH’s North Naples Hospital campus holds 311 licensed beds, including a neonatal intensive care unit (AHCA Florida Health Finder), and NCH describes its McDonald Pediatric Emergency Department there as Collier County’s 24-hour pediatric ER (NCH Emergency Services). It is about 19.2 miles and 27 minutes from the Winding Cypress gate.

Level II trauma: Gulf Coast Medical Center

Southwest Florida’s state-designated Level II trauma center is Gulf Coast Medical Center, at 13681 Doctors Way in Fort Myers, which AHCA lists as a Level 2 Trauma Center (AHCA Florida Health Finder). Lee Health moved its regional trauma center there in January 2022 (Lee Health press release). From the Winding Cypress gate it is 39.4 miles, about 50 minutes by road; in a true trauma case, EMS makes the transport decision, by ground or air.

Fire rescue and emergency response

Winding Cypress is inside the Greater Naples Fire Rescue District, per Collier County’s fire district layer. The nearest station is Station 23, at 6055 Collier Blvd, about 3.6 road miles and about 8 minutes without traffic from DiVosta’s former sales center at 7225 Wiregrass Court. The district’s published materials do not give an ISO fire-protection class for the community; an insurer’s declarations page shows the class it rates.

A realistic care map for a Winding Cypress household

How Long Are the Drives From Winding Cypress?

From the Winding Cypress gate on Collier Boulevard, Publix is about 4 minutes away, I-75 about 11, Fifth Avenue South about 18, the Naples Pier about 21 and Tigertail Beach on Marco Island about 23, all measured without traffic. Southwest Florida International Airport is about 49 minutes. January to April adds time on Collier Boulevard and US 41.

Data updated: September 2026

Every time in this section is measured from one origin, the junction of Winding Cypress Boulevard and Collier Boulevard, the community’s main entrance, using OpenStreetMap road data and the public OSRM routing engine on September 23, 2026. OSRM has no traffic model, so these are off-peak, free-flow figures; in season, and at school hours on Collier Boulevard, real drives run longer. A handful of rows are measured from the clubhouse at 7180 Winding Cypress Drive instead, about a kilometer inside the gate, and each is labeled.

Everyday errands

The daily loop is short. The Publix at Freedom Square, at US 41 and Collier Boulevard, is 1.7 miles and about 4 minutes from the gate (Publix, Freedom Square); the same center holds Burlington, HomeGoods and the restaurants along its Restaurant Row (Freedom Square property). A second Publix, at 8585 Collier Boulevard, is 2.6 miles and about 5 minutes north. Florida SouthWestern’s Collier Campus and Lely Elementary are each within about 5 minutes, and the hospital is 3.

Beaches, Marco Island and the water

The most-asked question about Winding Cypress is how far it is from the beach, and the measured answer is about 21 to 23 minutes. The Naples Pier is 11.1 miles and about 21 minutes from the gate; Tigertail Beach on Marco Island is 11.4 miles and about 23 minutes; the Jolley Bridge onto Marco Island is 8.6 miles and about 14 minutes. Collier County property taxpayers and full-time residents qualify for a free annual beach parking permit that works at county and City of Naples beach lots (Collier County beach parking information); without one, Tigertail charges $10 to park (Tigertail Beach Park). Isles of Capri is 9.2 miles and about 16 minutes, and the Collier Boulevard Park Boat Ramp just north of the Marco Island bridge reopened August 13, 2025 (Collier County news).

Downtown Naples and the shopping districts

Fifth Avenue South is 9.8 miles and about 18 minutes by Collier Boulevard and US 41. The larger north Naples shopping districts are farther: Waterside Shops is 16.3 miles and about 26 minutes, and Mercato is 18.5 miles and about 29 minutes, both by I-75 and Pine Ridge Road. For a Winding Cypress owner, downtown dinner is a 20-minute drive out of season and a longer one in February.

Airports and the interstate

I-75 at Exit 101, the Collier Boulevard interchange, is 6.1 miles and about 11 minutes north. Naples Airport, the general-aviation field with charter service, is 9.5 miles and about 17 minutes. Southwest Florida International Airport (RSW) in Fort Myers, the region’s commercial airport, is 38.8 miles and about 49 minutes by I-75 and Daniels Parkway. Marco Island Executive Airport is about 4.9 miles south of the community; Winding Cypress sits outside the county’s airport overlay (Collier County Airport Authority).

Parks, preserves and sports

The Rookery Bay Environmental Learning Center on Tower Road is 2.3 miles and about 4 minutes from the gate, the nearest door into the estuary. The Paradise Coast Sports Complex is 6.8 miles and about 12 minutes. From the clubhouse, Collier-Seminole State Park is 9.1 miles and about 16 minutes, and East Naples Community Park, home of the US Open Pickleball Championships, is 7.0 miles and about 14 minutes.

The full drive-time table

Measured from the clubhouse instead of the gate: Lely Resort’s public golf courses 2.6 miles, about 7 minutes; Collier-Seminole State Park 9.1 miles, about 16 minutes; Marco Island’s Rose Marina 11.0 miles, about 21 minutes; Port of the Islands 14.7 miles, about 23 minutes. All routes are OpenStreetMap routing without traffic, run September 23, 2026.

What Is Being Built Near Winding Cypress?

Near Winding Cypress, the adopted 2050 plan funds widening Collier Boulevard to six lanes between Manatee Road and Tower Road, while a US 41 overpass and a Benfield Road extension remain unfunded. A second Collier County Costco is approved about 3 miles north, and new neighborhoods, including Summerlit’s 249 homesites, are rising within about a mile.

Data updated: September 2026

The civic pipeline around Winding Cypress is a mix of road plans with real dates, private projects already under construction, and one large environmental project that just finished next door. We list what the public record shows and say plainly where it stops. Nothing below changes the gate, the fee stack or the zoning inside Winding Cypress itself.

Collier Boulevard widening, Manatee Road to Tower Road

The Collier Metropolitan Planning Organization’s 2050 Long Range Transportation Plan, adopted December 11, 2025, lists Collier Boulevard (SR 951), south of Manatee Road to north of Tower Road, widen from four to six lanes in its cost-feasible plan, with construction in Plan Period 2 and a present-day cost of $14.80 million. That is the stretch of Collier Boulevard just south of the community’s entrance, toward Rookery Bay and Marco Island. The plan’s technical compendium also lists Collier Boulevard from Barfield Drive to US 41 as an unfunded resilience need.

The US 41 overpass at Collier Boulevard

The same plan lists an overpass carrying US 41 over Collier Boulevard as an unfunded roadway need, with no cost and no schedule. The Collier MPO’s FY2027 to 2031 Transportation Improvement Program, approved June 12, 2026, carries no construction project at the US 41 and Collier Boulevard intersection, and the Florida Department of Transportation’s District One project list for Collier County shows only resurfacing work nearby. For the next several years, the intersection a Winding Cypress owner drives through most is what it is today.

The Benfield Road extension

The 2050 plan also lists Benfield Road from Hacienda Lakes Parkway to US 41 as a new two-lane road on a four-lane footprint, unfunded. The plan’s public-comment record states that Collier County identified the preferred alignment in its Benfield Road corridor study, and the comments describe that alignment tying into Naples Reserve Boulevard at US 41, east of Winding Cypress (2050 LRTP). Being unfunded through 2050, it is a long-horizon item rather than a near-term change.

A second Costco, about 3 miles north

Collier County approved a second Costco, about 162,700 square feet, at Collier Boulevard and Rattlesnake Hammock Road in October 2025, as WGCU reported. The Marco Eagle reported in March 2026 that the store was targeting a fall 2026 opening. We have not seen an opening date confirmed. From Winding Cypress it is roughly 3 miles north on Collier Boulevard.

New neighborhoods within about a mile

Collier County’s development applications layer and its planned unit development layer show several projects close by:

More rooftops mean more traffic on US 41 and Collier Boulevard over time, and more shopping and services close by. None of these projects shares a gate, an association or a district with Winding Cypress.

The Picayune Strand Restoration Project, next door

The largest project near Winding Cypress is environmental, and it is finished. The South Florida Water Management District’s Picayune Strand Restoration Project restores natural water flow across the former Golden Gate Estates land east of the community, and it was declared complete at a ribbon cutting in January 2026 (Everglades Foundation; Rep. Mario Diaz-Balart). Its Southwest Protection Feature, a levee and canal system north of US 41, exists to hold flood protection for the developed land beside the forest. No public document we found models the project’s effect on water levels in Winding Cypress specifically, so we do not claim one.

The Picayune Strand State Forest boundary itself is about 140 meters, under a tenth of a mile, from 7478 Winding Cypress Drive, per the Florida Natural Areas Inventory conservation lands layer. The forest covers 74,138 acres, per the Florida Forest Service. That neighbor is the reason the community’s east side will stay green; it is also the reason for the prescribed-burn smoke covered in the next section.

Land use and the Coastal High Hazard Area

Collier County’s Future Land Use layer places Winding Cypress in the Urban Residential Fringe Subdistrict, and the community lies outside the county’s Coastal High Hazard Area. The county’s development applications layer puts it in County Commission District 1.

Public safety

Winding Cypress is in unincorporated Collier County, so the Collier County Sheriff’s Office is the law-enforcement agency (CCSO patrol districts). The Florida Department of Law Enforcement’s incident-based data for the Sheriff’s Office jurisdiction show 153.5 violent offenses and 714.0 property offenses per 100,000 residents in 2024, down from 239.8 and 922.3 in 2021 (FDLE FIBRS offense detail). Those are county-wide figures for everything the Sheriff’s Office covers; no official crime figure is published for Winding Cypress alone.

How Do the Gate, Leasing, Pets, Utilities and Trash Work in Winding Cypress?

Winding Cypress has one gatehouse entrance on Collier Boulevard with attendants, license-plate readers and a virtual callbox, plus an automated rear gate. Leases run 30 days to one year, no more than three a year, with Board approval. Owners may keep up to three pets. Collier County supplies water, sewer and trash; Florida Power and Light supplies electricity.

Data updated: September 2026

These are the working rules of daily life, and they come from three documents: the Amended and Restated Declaration, recorded February 16, 2024, the HOA’s 2026 Rules and Regulations (final draft) and its May 2024 Rules. Where a detail is not in the public record, we say so rather than fill it in.

The main gate on Collier Boulevard

The main entrance is Winding Cypress Boulevard at Collier Boulevard, past a fountain the community shares with Verona Walk under a recorded 2014 cost-sharing agreement. The entrance has a gatehouse with attendants, resident and guest lanes, license-plate readers and a virtual callbox; the HOA moved its credentialing to a mobile system in 2025 and 2026, with plate readers at all gates, app-based credentials and mobile guest passes (HOA Board minutes, September 16, 2025). The 2026 budget carries $220,000 for vehicular access control (HOA 2026 Approved Budget). The public record does not state the attendants’ hours, and the recorded Declaration says the association is not obligated to provide security services, so we describe the entrance as gated and attended, nothing more.

The rear gate

A second, automated rear gate, with a barcode reader and cameras, serves the south end of the community. The public record does not state who may use it or its hours, so we leave it there; residents get the details at move-in.

Guests, vendors and real estate agents

Residents issue mobile guest passes through the gate app, and the HOA keeps a public Visitors and Agents page for guests, contractors and real estate professionals. Two key fobs come with each home for the clubhouse and amenities; extra fobs cost $25 each, per the Rules. Amenity hours are posted in the HOA Rules, and they change, so we do not repeat them here.

Leasing rules

The Declaration sets the rental rules, and they are tighter than in many East Naples communities:

• Minimum term: 30 continuous days.
• Maximum term: one year.
• Frequency: no more than three leases per calendar year, with at least 30 days between lease start dates.
• Whole home only: no renting a room or part of a home.
• Approval: every lease needs Board approval, with tenant screening through Tenant Evaluation, per the HOA’s lease and sale application flyer.

The Declaration allows the association to charge an application fee, but the current amount is not published. For an investor, the practical result is that Winding Cypress works for seasonal renters on 30-day to one-year terms and not for weekly vacation rentals.

Buying: notice, not approval

For a sale, the owner notifies the association at least 20 days before closing, and the association then records a Certificate of Approval (sample recorded certificate). Under the Declaration, the association cannot disapprove a sale. The buyer pays a $1,050 resale capital contribution (the 2025 figure in the HOA’s 2025 audit; the Board sets it annually), and the estoppel certificate fee is capped by Florida law, per the DBPR estoppel fee schedule.

Pets

Each household may keep up to three household pets. The Declaration excludes pit bulls, wolf hybrids and aggressive dogs, requires dogs to be leashed or carried outside the home, and does not allow invisible fences. The community has two fenced dog parks, one for small dogs and one for large, per the HOA’s amenities page.

Vehicles, boats and golf carts

Boats, trailers, recreational vehicles, commercial vehicles, motorcycles and golf carts must be kept in the garage, and overnight street parking is not allowed. Golf carts must be registered with the association, insured and driven by a licensed driver, and they may not leave the community. Owners with a boat should plan on off-site storage; the nearest public launch, the Collier Boulevard Park Boat Ramp, is covered in the drive-times section.

Fences, pools and exterior changes

Fences are tightly restricted and require architectural review approval; the current Rules allow only equipment screening. Above-ground pools are prohibited. The association’s architectural reviewer has 60 days to respond to an application and may require a refundable deposit of up to $5,000. Irrigation must connect to the community’s non-potable line.

Water, sewer and electric

Water and sewer service comes from the Collier County Water-Sewer District; the district conveyed the community’s utility facilities to the county by a recorded conveyance (Clerk record; Collier County water service area layer). Electricity is Florida Power and Light, per the federal electric retail service territory layer.

Natural gas

DiVosta marketed Winding Cypress as a natural-gas community and listed TECO Peoples Gas as the provider in 2015 (DiVosta Winding Cypress page, archived March 2015). Whether a given home has gas service today is shown on its utility bills.

Internet and TV

There is no bulk cable or internet package in the HOA’s 2026 budget, which carries only a $4,000 cable line for the association as a whole (HOA 2026 Approved Budget). Each owner contracts internet and TV individually, and providers vary by address.

Trash and recycling

Trash collection is Collier County’s, billed on the property tax bill. The 2025 bill for 7478 Winding Cypress Drive shows $261.91 for District 1 solid waste (Collier County Tax Collector, 2025 bill). There is no separate trash bill to set up at closing.

Mail, ZIP and transit

Winding Cypress addresses carry a Naples mailing address and ZIP code 34114. Collier Area Transit runs routes 11 and 24 along US 41 and Route 21 on Manatee Road (Collier Area Transit routes); inside the gates, the community is a car-and-golf-cart place.

Wildfire smoke and wildlife

Living beside a state forest has two everyday consequences. The Florida Forest Service runs prescribed burns in Picayune Strand, including an 818-acre burn that began December 10, 2025 (WINK News), so seasonal smoke is part of life here; the HOA posts the county’s planned-burn map for owners (2026 planned burns map). Collier County as a whole carries a “very high” wildfire-risk rating, higher than 97 percent of US counties, per the USDA Forest Service Wildfire Risk to Communities tool. The April 2026 Newman Road Fire in Picayune Strand, 1,733 acres, led to evacuations in other neighborhoods, not Winding Cypress (WGCU).

The wildlife is the other side of the same coin. A family of four black bears was filmed inside Winding Cypress in January 2025 (WINK News), and the Florida Fish and Wildlife Conservation Commission lists Florida panthers, black bears, wood storks and red-cockaded woodpeckers among the species of the Picayune Strand Wildlife Management Area. Keeping trash in the garage until pickup day and the dog on a leash goes a long way.

Moving in or moving on

The logistics above are the questions we answer most often on Winding Cypress showings, from the three-lease cap to the $1,050 contribution at closing. Thinking of selling? See what your Winding Cypress home is worth today, or Call Jesse direct at (239) 898-6072. Buying, and want the lease rules, gate setup and utility transfers handled before you arrive? Call Marc at (239) 287-5873, or read how our buyer representation works.

Winding Cypress vs Verona Walk: Which DiVosta Community Fits You?

Winding Cypress and Verona Walk are next-door DiVosta communities on Collier Boulevard in East Naples, built under one planned development on land from one landowner. Winding Cypress is the newer and smaller of the two, with 766 homes finished from 2015 to 2023; Verona Walk has 1,920 homes and began selling in 2003.

Data updated: September 2026

Buyers who tour one of these communities almost always tour the other. They sit side by side in ZIP 34114, they were built by the same company, DiVosta Homes, a PulteGroup brand, and they share a zoning approval, a school feeder pattern and part of an entry road. The differences that decide the choice are in the records: the age of the homes, the size of the community, what the amenities are and who owns them, what the fee stack adds up to, how FEMA maps the ground, and what the last twelve months of sales say about price. This section sets those records side by side, one yardstick at a time, and ends with a plain answer to who should choose which.

Our own guide to Verona Walk, the larger DiVosta community next door, covers that community in the same depth as this page covers Winding Cypress. Every cell below comes from a recorded document, a government layer, an association or district budget, or the Southwest Florida MLS; where the public record does not reach a yardstick for one community, the cell says so rather than guessing. A fee, rule or flood fact from one community never carries over to the other, even though they share a builder and a front door.

Why these two communities are compared

Winding Cypress and Verona Walk are two halves of the same approval. Collier County adopted the Winding Cypress Development of Regional Impact as Development Order 99-4 in December 1999, and the Winding Cypress PUD, about 1,928 acres approved for 2,854 units, covers both Verona Walk and Winding Cypress, per Collier County’s PUD layer and the county’s list of PUD ordinances. Barron Collier owned the land under both. DiVosta took the Verona Walk land first, with the first deed recorded September 3, 2003 in the Collier County Clerk’s official records, and bought the Winding Cypress land in three takedowns from 2014 to 2018.

Verona Walk borders Winding Cypress to the north. The two communities also share entry-road facilities: under a Cost Sharing Agreement recorded in 2014 among DiVosta, both homeowners associations and Barron Collier, the VeronaWalk association pays 31 percent of the shared road, bridge, fountain, drainage and landscaping costs. Both also sit under one master environmental resource permit family, 11-02132-P, at the South Florida Water Management District, whose permit layer lists the Winding Cypress phases under the Winding Cypress CDD and the Verona Walk Town Center under the VeronaWalk association. Few neighbors share this much and still differ so much in age, scale and cost.

The decision table

Sources, Winding Cypress column: the HOA’s 2026 Approved Budget, 2026 Rules and Regulations (final draft), Amended and Restated Declaration and 2025 audit; the Winding Cypress CDD’s FY2026/27 Final Budget; DiVosta’s archived 2016 community page for the clubhouse size; the Clerk’s first and last DiVosta-to-buyer deeds; FEMA’s National Flood Hazard Layer and LOMR-F points; Collier County’s evacuation zone layer; the district’s address lookup and the Florida Department of Education’s 2026 school grades. Verona Walk column: the VeronaWalk Homeowners Association and its recorded Declaration; the Verona Walk CDD’s fiscal 2026/27 adopted budget and FY2025 audited report; the association’s resale capital contribution notice; the resident Pickleball Club; DiVosta’s 2012 feature list; FEMA’s National Flood Hazard Layer and its 2024 revalidation letter for Collier County. Market rows for both communities: Southwest Florida MLS, explained below.

Twelve months of sales, the same search for each community

Both communities were searched the same way in the Southwest Florida MLS: by the MLS development name, residential sales closed in the trailing twelve months, with one median function applied to every figure. Winding Cypress was pulled September 23, 2026 for sales closed September 24, 2025 to September 23, 2026; Verona Walk was pulled September 24, 2026 for sales closed September 24, 2025 to September 24, 2026.

Winding Cypress’s all-home median of $807,500 is the midpoint of its two middle sales, $800,000 and $815,000, because 48 is an even count. Its attached and detached split follows the MLS building label on each listing; Verona Walk’s split follows the county’s building footprint, so treat the two split rows as close cousins rather than identical cuts. Both samples are small enough that one or two sales can move a median, and both windows end within a day of each other.

Read plainly, the market rows say three things. First, the median Winding Cypress sale ran $313,500 above the median Verona Walk sale, a gap that reflects a newer and more heavily detached housing stock (614 of Winding Cypress’s 766 homes are detached, against about half of Verona Walk’s). Second, the gap per square foot of living area is smaller, $394.83 against $306.19, about 29 percent. A 63 percent gap in median price against a 29 percent gap per foot means much of the difference is home size rather than price per foot. Third, Verona Walk trades more often and a little faster: 97 closings against 48, a median of 53 days on market against 73, and a sale-to-list ratio of 96.31 percent against 95.67 percent.

Where Winding Cypress comes out ahead

Newer construction. Every Winding Cypress home was built from 2015 to 2023, per Florida’s statewide cadastral roll, and DiVosta’s community spec sheets describe steel-reinforced concrete block walls, engineered roof trusses with hurricane tie-downs, tile roofs and galvanized steel hurricane shutters as standard. Newer construction matters most at insurance time: Citizens Property Insurance requires a four-point inspection on homes over 20 years old, a line the oldest Winding Cypress homes, built in 2015, will not reach until the mid-2030s, while a Verona Walk home completed in 2005 crossed it in 2025.

More courts, and clay tennis. The HOA’s 2026 Rules (final draft) list 4 Har-Tru clay tennis courts, 8 pickleball courts and 4 Har-Tru bocce courts; four of the pickleball courts came from converting a fifth clay tennis court in 2026, after the Collier County Hearing Examiner heard an appeal of the site plan on March 13, 2026. Verona Walk’s resident Pickleball Club lists six pickleball courts.

Preserve on a much larger scale. The five Winding Cypress plats cover about 1,176 acres, and about 818 of those acres are recorded preserve tracts, per Collier County’s parcel layer; the developed district covers about 358 acres. The Picayune Strand State Forest boundary is about 140 meters from 7478 Winding Cypress Drive on the Florida Natural Areas Inventory conservation lands layer, and about 70 home lots (46 detached and 24 villa lots, 40 of them in Phase One) touch a recorded preserve tract.

Fees you can read before you make an offer. The Winding Cypress HOA posts its approved budget on its own site, with a per-series total for 2026: Villa Series $6,247.75, Classic Series $6,657.76 and Estate Series $7,067.22 a year. The VeronaWalk association does not publish its assessment; a Verona Walk buyer sees it on the estoppel certificate.

A sale the association cannot block. Under the Winding Cypress Declaration, an owner notifies the HOA at least 20 days before closing, and the HOA cannot disapprove a sale; it records a Certificate of Approval in the public record.

A shorter minimum lease. Winding Cypress allows leases from 30 continuous days to one year, no more than three a year, with Board approval. Verona Walk’s recorded Declaration sets a four-month minimum. For an owner who wants to rent a month or two in season, Winding Cypress is the more flexible of the two.

Where Verona Walk comes out ahead

A lower price of entry. Verona Walk’s twelve-month median sale was $494,000 against $807,500 in Winding Cypress, and its attached homes sold at a median of $440,000 against $575,000 for Winding Cypress villas, per the Southwest Florida MLS figures above. A buyer who wants this stretch of Collier Boulevard for less money starts in Verona Walk.

A smaller district bill that ends sooner. Verona Walk homes pay the Verona Walk Community Development District $744.85 to $992.85 a year depending on home type, per its fiscal 2026/27 adopted budget, and its refunding bonds mature in 2035 and 2037. Winding Cypress homes pay $1,643.98 to $2,338.98 a year, and the district’s Series 2015 and Series 2019 bonds run to November 2045 and November 2049, per the Winding Cypress CDD budget. At each end of the two ranges the Winding Cypress figure is roughly $900 to $1,350 higher.

Two pools, a post office and a bigger town center. Verona Walk’s Town Center belongs to its association, so there is no club to join and no initiation fee, and it holds two pools, six pickleball courts, a restaurant and a post office. Winding Cypress has one resort-style pool with lap lanes and no post office.

Scale and liquidity. With 1,920 homes, Verona Walk offers more choice at any moment and more comparable sales for pricing: 97 closings in twelve months, a median of 53 days on market and a sale-to-list ratio of 96.31 percent.

More homes already amended out of the high-risk flood zone. FEMA issued 121 structure-specific map amendments for Verona Walk homes in 2024, 120 of them placing the house in Zone X, and revalidated the builder-era phase-wide amendments in its 2024 revalidation letter. In Winding Cypress, the builder-era letters were superseded on the 2024 map, and about 15 homes have their own letters placing them in shaded Zone X, per FEMA’s LOMR-F layer.

What the two communities share

For all their differences, a buyer choosing between Winding Cypress and Verona Walk is choosing between two homes that share most of their daily geography and several of their records:

• No age restriction in either. Winding Cypress’s recorded Declaration contains no housing-for-older-persons clause and defines “Family” to include children; Verona Walk’s association describes its community as open to all ages, and its recorded Declaration contains no age restriction either.
• The same zoned public schools. The district’s address lookup returns Lely Elementary, Manatee Middle and Lely High for every Winding Cypress address point checked for 2026-27, and the same three schools serve Verona Walk. The Florida Department of Education’s 2026 grades are A, A and B.
• The same evacuation zone. Both communities sit in Collier County Evacuation Zone D on the county’s evacuation layer, and neither was ordered out for Hurricane Ian or Hurricane Milton.
• The same hospital. Physicians Regional Medical Center, Collier Boulevard, with a 24-hour emergency room, is 2.2 miles and about 3 minutes without traffic from the Winding Cypress gate, per OpenStreetMap routing and the hospital’s state licensing profile.
• No golf, no marina. Neither community has a golf course or boat slips; the nearest public golf for both is at Lely Resort, where the Mustang and Flamingo Island courses require no membership.
• The same county services. Both are in unincorporated Collier County, both mail to Naples 34114, and both are served by the Greater Naples Fire Rescue District and the Collier County Sheriff’s Office.

What the fee comparison can and cannot show

The fee comparison is where buyers most often get stuck, so it helps to be precise about what each community publishes. Winding Cypress publishes both layers. The HOA’s 2026 Approved Budget sets a total for each series, including a $484 food-and-beverage minimum and a $223.89 Shady Palm assessment, and the CDD’s budget sets the district assessment for each product and phase. Add the county’s $261.91 solid-waste charge and the carrying cost before property tax and insurance runs from about $8,153.64 a year for a villa to about $9,668.11 for an Estate Series home on the Phase 3 plat (our sums of the published lines).

Verona Walk publishes one layer. Its district assessment is public, $744.85 to $992.85 a year, but its association assessment is not published; the amount for a specific home appears in the association’s annual budget and on the estoppel certificate issued for every resale. Until a buyer sees that certificate, a like-for-like total for Verona Walk is not possible from public documents, and any comparison that claims one is guessing. What can be said is that the district line alone is about $900 to $1,350 a year lower in Verona Walk, and that the capital contribution works differently: a flat $1,050 in Winding Cypress in 2025, against one quarter of the annual assessment for the home type in Verona Walk.

Who should choose Winding Cypress, who should choose Verona Walk

Choose Winding Cypress if you want newer construction (2015 to 2023), a detached home on a 50-foot or 65-foot homesite or a newer attached villa, clay tennis and eight pickleball courts, fees you can read in full before you offer, and a lot that may back onto some of the 818 acres of recorded preserve beside the Picayune Strand State Forest, and you accept a higher CDD line until the 2040s and a Zone AE flood map that makes elevation paperwork part of every purchase.

Choose Verona Walk if you want a lower price of entry, a larger community with more homes and more sales to choose from, a Town Center with two pools, a restaurant and a post office, and a smaller CDD line that ends in the 2030s, and you are comfortable with older homes, a four-month minimum lease and an association assessment you will first see on the estoppel certificate.

Both are gated DiVosta communities on one road with the same schools, so a buyer can tour both in a single afternoon. We represent sellers and buyers in each, and we price them against their own sales first, never against each other’s medians.

Selling a Winding Cypress home and wondering how it prices against Verona Walk? Get a free Winding Cypress home valuation, or Call Jesse direct at (239) 898-6072. Touring Winding Cypress and Verona Walk as a buyer? Call Marc at (239) 287-5873, or read how we represent buyers in Winding Cypress.

How Does Winding Cypress Compare With Other East Naples Communities?

Winding Cypress sits between Hacienda Lakes and Naples Reserve on price, with no golf and no equity club. Among five East Naples communities searched the same way in the Southwest Florida MLS, its single-family homes posted the highest sale-to-list ratio and the longest median days on market over the last twelve months.

Data updated: September 2026

Verona Walk is the natural rival, but it is not the only community a Winding Cypress buyer compares. South and east of Naples, along US 41 and Collier Boulevard, four other gated communities draw the same buyers: Hacienda Lakes, Naples Reserve, Fiddler’s Creek and Treviso Bay. Fiddler’s Creek and Treviso Bay include golf-membership product, Hacienda Lakes has no golf, and the MLS search does not state golf for Naples Reserve; their prices span more than two to one. To put all five on one yardstick, we ran the same search for each in the Southwest Florida MLS on September 23, 2026: single-family homes only, sales closed in the prior 365 days, each community by its own development name in the MLS dictionary (one entry each, so no neighboring development leaks into a row), with medians computed the same way for every row.

The benchmark table: five communities on one yardstick

Source: Southwest Florida MLS, single-family homes (MLS building label), sales closed September 24, 2025 to September 23, 2026, pulled September 23, 2026. Medians from an even count, such as Naples Reserve’s 50 sales, are the midpoint of the two middle sales. Winding Cypress villas are not in this table because the comparison is single-family to single-family; the Winding Cypress villa median over the same twelve months was $575,000 on 13 sales.

Reading the table: price versus price per foot

The two price columns tell different stories, and the difference is the useful part.

On median price, Winding Cypress sits in the middle of the pack. Its $875,000 single-family median is within 1 percent of Hacienda Lakes ($867,500), about 36 percent below Naples Reserve ($1,372,500), about 33 percent below Fiddler’s Creek ($1,299,500) and about 58 percent below Treviso Bay ($2,062,500) [our arithmetic from the table].

On price per square foot of living area, Winding Cypress sits higher than its median suggests. At $405.92 it runs about 11 percent above Hacienda Lakes ($364.61), even though the two medians are nearly identical. The reason is size: the median Winding Cypress home that sold had 2,158 square feet of living area, the smallest of the five, against 2,475 in Hacienda Lakes. Against the golf and larger-lot communities, Winding Cypress runs about 14 percent below Naples Reserve per foot, about 20 percent below Fiddler’s Creek and about 45 percent below Treviso Bay.

On negotiation, Winding Cypress sellers kept the most of their list price. Its median sale-to-list ratio of 96.26 percent is the highest of the five, narrowly ahead of Naples Reserve at 96.21 percent. It also posted the longest median days on market, 76, so the pattern in the last twelve months was patient pricing rather than fast sales: homes that sat longer but closed nearer their asking price.

On range, Winding Cypress is the tightest market of the five. Its single-family sales ran from $575,000 to $1,495,000, a narrower spread than any peer. A product line of three DiVosta series, all built from 2015 to 2023, produces a more predictable market than a community with several builders, several decades of construction or golf-membership homes at the top.

Every figure in this table is a single-family figure over a small sample, and one large sale can move a median. The table is a benchmark, not a forecast, and the right price for a particular home still comes from sales of its own series, phase and lot.

Naples Reserve

Naples Reserve, a lakes community of several builders off US 41 east of Collier Boulevard, is the community Winding Cypress buyers most often weigh when they want newer construction with more water. Collier County’s PUD Master List of June 11, 2026 lists the Naples Reserve Golf Club PUD at 688 acres with 1,075 homes built, and the Naples Reserve Community Development District’s document library counts 22 district-owned lakes covering 214.76 acres. Its single-family median in the benchmark, $1,372,500, is about 57 percent above Winding Cypress’s, and its median home is larger, at 2,602 square feet of living area. Where Winding Cypress was built by one builder in three series, recorded deeds in the Collier County Clerk’s official records show eight builders at Naples Reserve. Buyers who choose Winding Cypress over Naples Reserve usually do so for the lower price, the single-builder consistency and the preserve setting; buyers who choose Naples Reserve usually do so for the larger lake system and larger homes.

Treviso Bay

Treviso Bay, the gated East Naples golf community, sits at the top of the benchmark: a single-family median of $2,062,500 on 20 sales, $736.68 per square foot of living area and a median of just 25 days on market, the fastest of the five. The MLS search for Treviso Bay includes golf-membership product, which Winding Cypress does not have. For most Winding Cypress buyers, Treviso Bay is a different price bracket rather than a direct alternative; it matters to this page mainly as the upper anchor of the East Naples market, and as the answer for a buyer who decides golf inside the gates is worth more than twice the median price.

Hacienda Lakes and Fiddler’s Creek

Hacienda Lakes is Winding Cypress’s closest match on price. The two single-family medians, $867,500 and $875,000, are $7,500 apart, and neither community has golf. The difference is what the money buys: Hacienda Lakes’s median home that sold was larger (2,475 square feet of living area against 2,158) at a lower price per foot ($364.61 against $405.92), and its sales ran across a much wider range, up to $2,840,000. A buyer who wants the most square feet for about $870,000 will look hard at Hacienda Lakes; a buyer who wants a smaller, newer DiVosta home beside a state forest will lean to Winding Cypress.

Fiddler’s Creek is the largest market in the benchmark, with 98 single-family sales in twelve months, and its MLS search includes golf-membership product. Its single-family median of $1,299,500 and $505.53 per foot put it well above Winding Cypress, and its sale-to-list ratio, 94.81 percent, was lower. For a buyer choosing between them, the question is usually golf: Winding Cypress has none inside the gates, and the nearest public golf is at Lely Resort, about 2.6 road miles and 7 minutes from the clubhouse without traffic.

Where Winding Cypress fits

Put together, the benchmark places Winding Cypress as the newer, non-golf, single-builder option in the middle of the East Naples price range: close to Hacienda Lakes on price, well below the golf communities, and the tightest and most list-price-faithful market of the five over the last twelve months. Its amenity package is bundled into the HOA assessment with no equity membership and no non-resident members, per the HOA’s 2026 Rules (final draft), which is the other half of why it trades below the golf communities per square foot.

Selling in Winding Cypress and want to know which of these markets your buyer is also shopping? Get a free Winding Cypress home valuation, or Call Jesse direct at (239) 898-6072. Comparing East Naples communities as a buyer? Call Marc at (239) 287-5873, or read how we represent buyers across Southwest Florida.

What Are the Honest Pros and Cons of Buying in Winding Cypress?

Winding Cypress’s strengths are on the record: homes built from 2015 to 2023, about 818 acres of recorded preserve, one HOA with every amenity bundled and a hospital 3 minutes away. Its trade-offs are just as documented: a Zone AE flood map, a CDD line into the 2040s and carrying costs above $8,000 a year.

Data updated: September 2026

Every community has a list like this, and most pages print only the first half. We print both because the buyers who close happily in Winding Cypress are the ones who knew the second half before they wrote an offer, and the sellers who get their price are the ones who answered it in the listing. Each item below carries the document behind it.

The pros, with the record behind each

• Newer homes, built to a stated spec. Every home was built from 2015 to 2023, per the state’s cadastral roll, and DiVosta’s spec sheets list steel-reinforced concrete block construction, engineered trusses with hurricane tie-downs, tile roofs and galvanized steel shutters as standard, with a DiVosta 10-year limited structural warranty.
• Preserve on a scale few communities match. About 818 of the roughly 1,176 acres on the five plats are recorded preserve tracts, per Collier County’s parcel layer, and the 74,138-acre Picayune Strand State Forest begins about 140 meters from 7478 Winding Cypress Drive.
• One association, amenities bundled. There is one homeowners association, no villa or neighborhood sub-associations, no equity club, no separate membership and no non-resident members; the clubhouse, pool, courts and café are paid for inside the assessment, per the HOA’s 2026 Approved Budget.
• An assessment that went down. The 2026 Estate Series quarterly assessment, before the food-and-beverage minimum, fell from $1,662.31 to $1,645.80, about 1.0 percent, in the same budget.
• Racket sports on clay and hard courts. Four Har-Tru clay tennis courts, eight pickleball courts and four Har-Tru bocce courts, per the 2026 Rules (final draft), and a resident Pickleball Club whose 2026 dues were $20 a person.
• A restaurant by the pool. The Shady Palm Café, a poolside bar and restaurant run by the HOA with its own manager and chef, per the HOA’s amenities page.
• A-rated elementary and middle schools. Lely Elementary and Manatee Middle both earned an A in the 2026 state grades; Lely High earned a B.
• A hospital and urgent care within minutes. Physicians Regional Medical Center, Collier Boulevard, is 2.2 miles and about 3 minutes from the gate, and NCH Medical Group Immediate Care Southeast is 1.7 miles and about 3 minutes, both without traffic.
• Inland, in Evacuation Zone D. Every sampled address is in Zone D on the county’s evacuation layer; after Hurricane Ian, CDD minutes recorded that “No significant damage was noted by the community.”
• A flood insurance discount. Unincorporated Collier County is Class 5 in FEMA’s Community Rating System, worth a 25 percent discount on eligible flood policies in the Special Flood Hazard Area, per FEMA’s community status record.
• A sale the HOA cannot block. The HOA must be told at least 20 days before closing but cannot disapprove a sale, under the Declaration.
• A tight, seller-leaning market. Nine homes were for sale on September 23, 2026, about 2.2 months of supply, and homes sold at a median 95.67 percent of list price over the prior twelve months, per the Southwest Florida MLS.

The cons, with the record behind each

• Zone AE on the current flood map. FEMA’s map effective February 8, 2024 places every sampled Winding Cypress address in Zone AE, with a base flood elevation of 8.0 feet NAVD88, per the National Flood Hazard Layer. A lender will usually require flood insurance unless a home has its own FEMA letter moving it to shaded Zone X, and only about 15 homes do.
• A CDD assessment into the 2040s. Homes pay $1,643.98 to $2,338.98 a year before the 4 percent November discount, per the CDD’s FY2026/27 budget, until the Series 2015 bonds retire in November 2045 and the Series 2019 bonds in November 2049.
• A district line that rose sharply once. The district’s operations and maintenance assessment rose from $232.06 in FY2022/23 to about $795 in FY2023/24 and has held at $794.98 since; the driver is lake-bank remediation, budgeted at $300,000 for FY2026/27, after a 2024 lake assessment logged erosion across the 29 lakes.
• Carrying costs above $8,000 a year before tax and insurance. HOA, CDD and county solid waste together run about $8,153.64 a year for a villa to about $9,668.11 for an Estate Series home on the Phase 3 plat (our sums of the published lines).
• No golf, no marina, and lakes you can only look at. The lakes belong to the CDD and the Rules allow no recreational access, including fishing, boating and swimming; boats, trailers and golf carts must be garaged.
• About 21 to 23 minutes to the beach. Naples Pier is 11.1 miles and about 21 minutes, and Tigertail Beach on Marco Island 11.4 miles and about 23 minutes, from the gate without traffic.
• Prescribed-burn smoke and wildfire risk. The Florida Forest Service burns in Picayune Strand, including an 818-acre prescribed burn that began in December 2025, and the USDA Forest Service rates Collier County’s wildfire risk as higher than 97 percent of US counties.
• Leasing limits. The Declaration allows no more than three leases a year, each of 30 days to one year, with Board approval, which rules out short-stay rentals.
• Tight exterior rules. Fences are tightly restricted and need architectural approval (the current Rules allow only equipment screening), above-ground pools are prohibited, and signs, including real estate signs, need Board consent or Rules permission.
• A contested court conversion. The 2026 conversion of a clay tennis court into four pickleball courts went to a Hearing Examiner appeal, and 2025 and 2026 HOA board minutes record a pre-suit mediation demand over it; the HOA has not published a completion date.

Who Winding Cypress suits, and who it does not

Winding Cypress suits a buyer who wants a newer DiVosta home with a clay-court, pickleball and poolside-café routine inside the gates, preserve beside the back lanai, A-rated elementary and middle schools, and a hospital minutes away, and who is comfortable budgeting $8,150 to $9,670 a year in association, district and solid-waste charges before tax and insurance. It suits less well a buyer who wants golf or boating from home, a walk to the beach, short-stay rental income, or the lowest possible carrying cost; Verona Walk next door and the golf communities in the benchmark above answer those needs better.

What sellers should take from this list

A Winding Cypress seller can turn most of the cons into answered questions before a buyer asks them. The flood question is answered by the home’s Elevation Certificate, which Collier County likely already holds (the county’s Elevation Certificate layer shows 230 on Winding Cypress streets), and by any FEMA letter for the lot. The CDD question is answered by the district’s budget table for the home’s product and phase. The carrying-cost question is answered by the HOA’s published budget for the series. A listing that carries all three from the first day removes the three most common reasons a Winding Cypress buyer pauses.

Thinking of selling? Get a free Winding Cypress home valuation, or Call Jesse direct at (239) 898-6072. Weighing the pros and cons as a buyer? Call Marc at (239) 287-5873 for a straight conversation about whether Winding Cypress fits, or read how we represent buyers in Winding Cypress.

Thinking of Selling Your Winding Cypress Home? List With the #1 Team in Southwest Florida Since 2012

If you’re searching for the best Winding Cypress listing agent, or thinking, ‘I need to sell my house in Winding Cypress…’, McGreevy and Comisar sell Winding Cypress homes on the record. Buyers ask three things first: what the flood letter says, what the CDD costs and what the HOA charges. We answer each from the record.

Data updated: September 2026

Selling in Winding Cypress means selling one of 766 fee-simple DiVosta homes in three series, in a community where the builder closed its last sale in December 2023 and every home now changes hands as a resale. In the last 12 months we tracked 48 Winding Cypress closings, each one pulled and checked in the Southwest Florida MLS, and they show a market that rewards preparation: homes that arrived with their paperwork answered sold close to their asking price, and homes that did not waited. A Winding Cypress listing competes first with homes of its own series on its own plat, then with Verona Walk next door, then with Hacienda Lakes and Naples Reserve. As the leaders of Domain Realty Group our team has closed over $2.5 billion in real estate, and that is the discipline a Winding Cypress listing needs: a price built from sales of the same series and phase, a file that clears the HOA’s 20-day notice and estoppel without a delay, and a flood and insurance packet that answers the underwriter before the underwriter asks.

Honors and recognition:

• Top 1% Real Estate Agents Nationally Since 2008
• 5 Star Award for Customer Satisfaction for 21 Straight Years. Only 5 out of 21k+ Licensees (Gulfshore Life Magazine)
• #1 Team in Southwest Florida since 2012
• McGreevy and Comisar and their Domain Realty Group team have sold over $2.5 Billion in Real Estate
• McGreevy and Comisar alone have over $900 million in Sales
• Nationally Recognized Top Producing Realtors
• Platinum Sales Production Award Winners

★★★★★ “Marc made an extremely stressful time of selling my parents’ house easier because of his expertise, compassion, and diligence. I cannot thank him enough and I would recommend him without reservation.” Verified Google review

What Winding Cypress Homes Sold For in the Last 12 Months

In the 12 months from September 24, 2025 to September 23, 2026, 48 Winding Cypress homes sold for a combined $38,718,900, per the Southwest Florida MLS (development name Winding Cypress, pulled September 23, 2026):

• Single-family homes: 35 sales, median $875,000, $405.92 per square foot of living area, median living area 2,158 square feet, a median of 76 days on market and a median 96.26 percent of list price; sales ran from $575,000 to $1,495,000.
• Villas: 13 sales, median $575,000, $370.01 per square foot of living area, median living area 1,554 square feet, a median of 50 days on market and a median 94.76 percent of list price; sales ran from $455,000 to $635,000.
• Whole community: median $807,500 (the midpoint of the two middle sales, $800,000 and $815,000), $394.83 per square foot of living area, a median 95.67 percent of list price and a median of 73 days on market across the 46 sales that carry a days-on-market figure; 7 of the 48 homes sold at or above their list price.
• The top of the market: $1,495,000 for 7412 Winding Cypress Drive (3,656 square feet, March 11, 2026), $1,475,000 for 6912 Cocoplum Street (May 13, 2026) and $1,260,000 for 6839 Winding Cypress Drive (November 21, 2025). The highest sale in the last 48 months was $1,895,000, for 7513 Winding Cypress Drive on January 4, 2024.
• Where the sales were: Winding Cypress Drive 12, Jacaranda Lane 12, Live Oak Drive 10, Pennyroyal Drive 6, Mockingbird Court 3, Blackberry Drive 2, and one each on Cocoplum Street, Clamshell Lane and Geranium Way.
• Inventory on September 23, 2026: 9 homes for sale, 7 single-family homes at a median list price of $1,250,000 (from $920,000 to $1,349,500) and 2 villas at $575,000 and $599,900, plus 2 pending sales at $1,200,000 and $799,900. That is about 2.2 months of supply for the community, 2.4 for single-family homes and 1.8 for villas.

Two numbers in that list matter most to a seller. The first is the gap between the single-family median list price on the market today, $1,250,000, and the single-family median sale over twelve months, $875,000: current asking prices sit well above what the last year of sales supports, and the homes that close are the ones priced against sales rather than against neighbors’ asking prices. The second is the sale-to-list ratio of 95.67 percent: buyers still negotiated about 4 percent off list, so a list price with no room in it tends to sit.

How Winding Cypress Prices Moved From 2023 to 2026

Source: Southwest Florida MLS, closed sales by calendar year, pulled September 23, 2026. The 2024 single-family median is the midpoint of two middle sales that were both $1,000,000, and the 2026 figure is the midpoint of $890,000 and $900,000.

Single-family prices peaked in 2024 at a $1,000,000 median, reset about 14 percent in 2025 and are recovering in 2026, up 4.1 percent on the median so far. Villas peaked earlier, at $710,000 in 2023, fell about 24 percent to $537,000 in 2025 and are up 7.1 percent in 2026. On a trailing twelve-month basis, closings rose from 40 to 48, about 20 percent; the single-family median rose 1.7 percent, from $860,000 to $875,000, while single-family price per square foot slipped 2.8 percent, from $417.66 to $405.92, meaning larger homes made up more of the sales; and the villa median rose 2.7 percent, from $560,000 to $575,000, while the villa median days on market halved, from 107 to 50. These are small samples, and a handful of sales can move any of them.

The Winding Cypress Seller Playbook: Price by Series, Phase and Lot

Winding Cypress does not trade as one market, and a single community median tells a seller very little. The community has three product lines, and each one prices on its own: 152 attached villas in the Villa Series, 406 Classic Series homes on 50-foot homesites and 208 Estate Series homes on 65-foot homesites, per the CDD’s FY2026/27 budget. We price a Winding Cypress home first against sales of the same series, then adjust for plat, lot, condition, upgrades and the home’s flood record.

The MLS makes that harder than it should be. Its building-design field offers “Single Family” and “Villa Attached” for Winding Cypress and nothing else, so it has no value for Classic or Estate, and every portal that reads the MLS shows Winding Cypress as one undifferentiated single-family market. The series has to be read from the homesite width, the floor plan and the recorded plat, which is exactly the work we do before we set a price. DiVosta’s brochure names the plans: Classic Series plans such as the Palmary, Prestige, Prosperity and Mystique, and Estate Series plans such as the Pinnacle, Tangerly Oak and Stonewater, which run from about 2,488 to 3,894 square feet under air.

Four details that are specific to Winding Cypress move the number:

• The plat, because it sets the CDD debt. Homes on the Phase 3 plat carry Series 2019 debt of $1,429 (50-foot) or $1,544 (65-foot) a year, against $954 or $1,060 for the same homesite widths on Phases 1 and 2, per the CDD budget. A buyer comparing two otherwise similar homes will notice a difference of roughly $475 to $485 a year.
• The lot, because preserve is the view people pay to see. About 70 lots touch a recorded preserve tract, 40 of them in Phase One, per the county’s parcel layer. No public data measures a preserve premium in Winding Cypress, so we price it from the specific sales that had one.
• The flood record, because it sets the buyer’s insurance quote. A home with its own FEMA letter placing it in shaded Zone X and a current Elevation Certificate presents very differently to an insurer than one without, even on the same street; surveyed floors on the two certificates we read in full sit about 2.1 and 1.4 feet above the 8.0-foot base flood elevation, and about 1.4 to 2.7 feet across all the certificates we reviewed.
• The openings, because they drive the wind premium. DiVosta made galvanized steel shutters standard and impact glass optional, so a home with impact glass and a current wind mitigation report hands the insurer documented credits to apply, and we put that report in front of buyers early.

For context only, Collier County’s 2026 preliminary roll puts the median just value of a Winding Cypress villa at $495,624 and of a detached home at $743,973. Those are county estimates as of January 1, not sale prices, and they are measured on a different area basis from the MLS, so they are never a pricing tool on their own.

What Winding Cypress Buyers Ask First, and the Record That Answers Each

The Documents File We Build for Every Winding Cypress Listing

A Winding Cypress sale runs on paperwork, and the order matters. The file we assemble before a Winding Cypress home goes on the market:

• The HOA estoppel certificate. It states every assessment owed on the home, and the Declaration requires the HOA to issue it within 10 business days. Florida’s section 720.30851 caps the fee, and the current DBPR schedule sets the cap at $299, plus $119 for expedited delivery; the HOA’s actual fee prints on the certificate.
• The homeowners’ association disclosure. The statutory disclosure summary for a home in a homeowners’ association, under section 720.401.
• The CDD disclosure and the home’s assessment line. Florida’s section 190.048 requires a disclosure to buyers of property in a community development district, and we attach the district’s budget table for the home’s product and phase so the buyer sees the exact figure.
• The flood disclosure, Elevation Certificate and any FEMA letter. Florida’s residential flood disclosure, created in 2024 and summarized in the Florida Senate’s bill analysis, requires sellers to disclose known flooding, flood insurance claims and federal flood assistance. Because Winding Cypress is mapped Zone AE, the Elevation Certificate and any FEMA letter for the lot belong in the file on day one.
• The wind mitigation report and roof record. A current wind mitigation report on the state form, valid for up to five years under Florida OIR guidance (a new form took effect April 1, 2026), plus the roof permit date and whether the home has impact glass or shutters.
• The HOA’s sale steps. Notice to the HOA at least 20 days before closing, the buyer’s $1,050 capital contribution and the HOA’s recorded Certificate of Approval, which the HOA cannot withhold for a sale, under the Declaration.

What Is Your Winding Cypress Home Worth? Get a Free Valuation in 60 Seconds.

Start with a free Winding Cypress home valuation. It takes about a minute, and Jesse follows up with the sales that actually fit your home: the same series, the same plat and CDD tier, and, where it matters, the same flood record, not a community median that mixes a Jacaranda Lane villa with an Estate Series home on Winding Cypress Drive. Prefer to talk first? Call Jesse direct at (239) 898-6072.

(239) 898-6072, text or call. Confidential conversations welcome.

Who is the best listing agent for Winding Cypress?

McGreevy and Comisar lead Domain Realty Group, the #1 Team in Southwest Florida since 2012, and have been Top 1% Real Estate Agents Nationally Since 2008, with over $900 million in personal sales, which makes them among the most experienced listing teams a Winding Cypress seller can hire. We list a Winding Cypress home with its record in hand: the HOA budget for its series, the CDD line for its plat, and FEMA’s file and the county’s Elevation Certificate for its address. Call Jesse direct at (239) 898-6072 or get a free Winding Cypress home valuation.

What is my Winding Cypress home worth?

A Winding Cypress home’s value starts with its product line. Over the 12 months to September 23, 2026, single-family homes sold at a median of $875,000 and $405.92 per square foot of living area, and villas at a median of $575,000 and $370.01, per the Southwest Florida MLS. Series, plat, preserve frontage, condition and flood record then move the number, which is why a valuation built from sales of your own series beats any community median. Get a free Winding Cypress home valuation or call Jesse direct at (239) 898-6072.

Does the Winding Cypress HOA have to approve my buyer?

No, not in the sense of a veto. Under the Winding Cypress Declaration, you notify the HOA at least 20 days before closing, the HOA cannot disapprove the sale, and it records a Certificate of Approval in the county’s official records. Leases are different: every lease needs Board approval, and tenants are screened through the HOA’s Tenant Evaluation process. Build the 20-day notice into the contract timeline from the start.

Will my buyer take over the Winding Cypress CDD assessment?

Yes. The CDD assessment is a lien on the lot until the bonds are paid, so it stays with the home and appears on the buyer’s county tax bill each November. For fiscal 2026/27 it runs from $1,643.98 a year for a villa to $2,338.98 for a 65-foot homesite on the Phase 3 plat, before the 4 percent November discount, per the CDD budget. Showing the buyer the exact line for your plat and homesite width, early, turns a question into a known number.

Does my Winding Cypress home need a FEMA letter to sell?

No, but it helps. Winding Cypress is mapped Zone AE on FEMA’s map effective February 8, 2024, so most buyers with a mortgage will need flood insurance. About 15 homes have their own FEMA letters placing them in shaded Zone X, searchable by address on the FEMA Map Service Center; a lender may still require coverage, but the letter usually changes the quote. If your home has one, or if its Elevation Certificate shows a floor well above the 8.0-foot base flood elevation, it belongs at the front of the listing.

How do buyers and agents get through the Winding Cypress gate for showings?

Visitors and agents follow the HOA’s Visitors and Agents process at the Collier Boulevard gatehouse, where attendants work alongside license-plate readers and a virtual callbox, and residents can issue mobile guest passes through the SAGE app. We register every showing ahead of time, so no buyer is turned away at the gate, and we clear any sign or open-house plans against the Rules first, because signs, including real estate signs, need Board consent or Rules permission.

Your Local Real Estate Experts

Jesse McGreevy and Marc Comisar are the McGreevy and Comisar team behind this guide to Winding Cypress, and they lead Domain Realty Group from an office on US 41 in Bonita Springs, north of Naples. Jesse leads the listing side, and Marc works with buyers across Collier and Lee counties, including the East Naples communities along Collier Boulevard.

Jesse McGreevy is a top-reviewed Winding Cypress realtor on Google. Jesse McGreevy, Sales Associate, and Marc Comisar, Broker Associate, built the team on a simple idea: the seller or buyer who understands the record before the first showing negotiates from strength.

McGreevy and Comisar lead Domain Realty Group, a full-service Southwest Florida real estate team. Learn more about our team at DomainRealtyGroup.com. Read more on our about the McGreevy and Comisar team page.

• Top 1% Real Estate Agents Nationally Since 2008
• 5 Star Award for Customer Satisfaction for 21 Straight Years. Only 5 out of 21k+ Licensees (Gulfshore Life Magazine)
• #1 Team in Southwest Florida since 2012
• McGreevy and Comisar and their Domain Realty Group team have sold over $2.5 Billion in Real Estate
• McGreevy and Comisar alone have over $900 million in Sales
• Nationally Recognized Top Producing Realtors
• Platinum Sales Production Award Winners

How we handle a Winding Cypress listing. Before a word of this guide was written, we read the Winding Cypress Amended and Restated Declaration and its recorded amendments, the HOA’s 2026 budget, Rules, reserve study and 2025 audit, the Winding Cypress Community Development District’s budgets, engineer’s report and lake assessment, FEMA’s flood map and its letters for the community, Collier County’s parcel, zoning, evacuation and Elevation Certificate layers, the five recorded plats, and the school district’s own address lookup. When we list a Winding Cypress home we put that work to use. We price it against sales of its own series and plat, because the MLS cannot tell a Classic Series home from an Estate Series home and buyers can. We pull the home’s CDD line for its product and phase, its FEMA record and its Elevation Certificate before the listing goes live, so the buyer sees all three on day one. We give the HOA its 20-day notice as soon as a contract is signed, and we register every showing at the gate ahead of time. As the leaders of Domain Realty Group our team has closed over $2.5 billion in real estate, and on a Winding Cypress listing the record comes first.

Jesse McGreevy and Marc Comisar are top-reviewed on Google, and the quotes below are five-star client reviews reproduced in each reviewer’s own words. We publish no aggregate score and no star-rating widget. Read the full set on the McGreevy and Comisar Google Business Profile.

★★★★★ “Jesse listened to what we were looking for and found us exactly what we wanted. Jesse was always available to answer any questions and helped us through the entire process.” Verified Google review

★★★★★ “He was quick to respond with any questions about the purchase of our new home and made sure everything went smoothly! We highly recommend him as an agent!” Verified Google review

★★★★★ “Jesse and his team were the most professional and communicative people throughout the entire process! Always available and helpful! Highly recommended!” Verified Google review

• Jesse McGreevy: (239) 898-6072 · [email protected]
• Marc Comisar: (239) 287-5873
• Office: 24031 S Tamiami Trl #101, Bonita Springs, FL 34134

Jesse McGreevy (Sales Associate, SL3101296) and Marc Comisar (Broker Associate, BK3060671) are licensed Florida REALTORS® with Domain Realty; Florida real estate licensure is regulated by the Florida Real Estate Commission (FREC).

License status for either name can be verified through the Florida Department of Business and Professional Regulation’s public licensee search, the authority of record for Florida real estate licensure.

Selling a home in Winding Cypress? Get a free Winding Cypress home valuation, or call Jesse direct at (239) 898-6072.

Buying in Winding Cypress? Call Marc at (239) 287-5873, or read how we represent buyers in Winding Cypress.

Frequently Asked Questions, Buyer Edition

Data updated: September 2026

These are the questions buyers ask about Winding Cypress, answered from the public record: where the community sits, who governs it, what the association and the district bill each year, what FEMA’s map says, which schools serve each address, how far the beach is, and what the market has done over the last 12 months. Market figures come from Southwest Florida MLS data pulled September 23, 2026; every other figure links to the document it comes from. Where the record is silent, the answer says so.

Where exactly is Winding Cypress?

Winding Cypress sits north-east of the intersection of US 41 (Tamiami Trail East) and Collier Boulevard (County Road 951) in East Naples, with US 41 as its south-west border and Verona Walk directly to its north. The district engineer’s Master Engineer’s Report of September 22, 2015 places the project in the “Northeast quadrant” of that intersection. The main gate is on Collier Boulevard at Winding Cypress Boulevard, and the clubhouse and HOA office are at 7180 Winding Cypress Drive, per the HOA’s contact page.

Is Winding Cypress in the City of Naples?

No. Winding Cypress is in unincorporated Collier County and uses a Naples mailing address, so county government, not the City of Naples, handles its zoning, permits and services. The US Census Bureau also treats Winding Cypress as its own Census Designated Place, shown on the 2020 TIGERweb Census Designated Places layer. Fire rescue comes from the Greater Naples Fire Rescue District and law enforcement from the Collier County Sheriff’s Office, per the county’s fire district layer.

What ZIP code is Winding Cypress?

Winding Cypress homes carry ZIP code 34114 with a Naples, Florida mailing address. Collier County Public Schools’ address lookup and the Census geocoder both resolve 7478 Winding Cypress Drive to Naples 34114. The same ZIP covers much of East Naples along Collier Boulevard and US 41, so when you search listings by ZIP alone you will also see Verona Walk, Naples Reserve and other nearby communities; search by the community name to see Winding Cypress homes only.

How far is Winding Cypress from the beach?

From the Collier Boulevard gate, the nearest beaches are about 21 to 23 minutes away without traffic: Naples Pier is 11.1 miles and about 21 minutes, and Tigertail Beach on Marco Island is 11.4 miles and about 23 minutes, measured with OpenStreetMap routing. The Jolley Bridge onto Marco Island is 8.6 miles and about 14 minutes. January to April adds time on Collier Boulevard and US 41. Collier County property taxpayers and full-time residents qualify for a free annual beach parking permit valid at county and City of Naples beach lots; without it, Tigertail Beach Park charges $10 to park.

Is Winding Cypress gated?

Yes. The Collier Boulevard entrance has a gatehouse with attendants, plus license-plate readers and a virtual callbox, and a second, automated rear gate with a barcode reader and cameras serves the south end, per the HOA’s April 2026 community update and its 2025 reserve study. The 2026 budget carries a $220,000 vehicular access control line. The recorded Amended and Restated Declaration expressly disclaims any obligation to provide security, so read the gate as access control, and the HOA does not publish gatehouse staffing hours.

Is Winding Cypress age-restricted?

No. Winding Cypress is not age-restricted. The recorded Amended and Restated Declaration, Articles and Bylaws, recorded February 16, 2024 at Official Records Book 6330, Page 3383, contain no housing-for-older-persons clause, and the definition of “Family” includes children. The HOA’s 2026 Rules set age rules for specific rooms instead: the fitness center bars children under 13 and requires ages 13 to 18 to be accompanied. The builder was DiVosta Homes, a PulteGroup brand, not PulteGroup’s age-restricted brand.

How many Winding Cypress owners live there full time?

The HOA’s certified October 2025 survey found 56.3% of responding households live in Winding Cypress full time and 43.7% part time; 360 of the 766 households answered. That split shapes the community calendar, with the busiest months for clubs, dining and events running from late fall through spring. The 2020 Census counted 697 residents in the Winding Cypress Census Designated Place, per the 2020 TIGERweb layer, but that count was taken before build-out finished in 2023, so it understates today’s population.

Who built Winding Cypress?

DiVosta Homes, a PulteGroup brand, built all 766 homes in Winding Cypress, and DiVosta also built Verona Walk next door. DiVosta bought the Winding Cypress land from Barron Collier interests in three recorded takedowns: July 10, 2014 ($5,025,000), April 30, 2015 ($15,356,250) and June 22, 2018 ($11,395,500), a total of $31,776,750. The builder’s Winding Cypress digital brochure describes the three product lines, the floor plans and the construction specifications. The first DiVosta sale to a buyer was recorded on June 30, 2015.

Is DiVosta still building in Winding Cypress?

No. DiVosta’s last sale of a new Winding Cypress home to a buyer was recorded on December 21, 2023, and every home now sells as a resale. The builder’s deeds by year trace the build-out: 67 in 2015, 127 in 2016, 114 in 2017, 111 in 2018, 109 in 2019, 83 in 2020, 90 in 2021, 53 in 2022 and 9 in 2023, per the Collier County Clerk’s Official Records index. DiVosta deeded the lake tracts and most of the preserve tracts to the CDD in October 2021 and the roads and common tracts to the HOA in January 2022.

How many homes are in Winding Cypress?

Winding Cypress has 766 homes: 152 attached villas in the Villa Series, 406 Classic Series homes on 50-foot homesites and 208 Estate Series homes on 65-foot homesites, per the unit census in the CDD’s FY2026/2027 budget. The HOA’s home page and the 2026 HOA budget also count 766. The district engineer planned about 781 homes in 2015; 766 were built. The HOA’s 2026 budget counts the detached split as 408 Classic and 206 Estate, a two-lot difference from the CDD’s census that neither document explains.

What floor plans are in Winding Cypress?

DiVosta’s Winding Cypress brochure lists the Estate Series plans on 65-foot homesites as Pinnacle (2,488 to 3,676 air-conditioned square feet), Tangerly Oak (2,589 to 2,938) and Stonewater (2,852 to 3,894). Classic Series plans on 50-foot homesites include Palmary (1,943 to 2,063), Prestige (2,080 to 2,257), Prosperity (1,670 to 1,790) and Mystique (1,889 to 3,037). Earlier designs sold from 2015 to 2019 include Abbeyville, Martin Ray, Summerwood, Cressida and Infinity, per DiVosta’s archived 2019 community page. Builder square footage is air-conditioned area, which differs from the MLS living-area figure.

How big is Winding Cypress, and how much of it is preserve?

The five recorded Winding Cypress plats cover about 1,176 acres, and about 818 of those acres are recorded preserve tracts, per Collier County’s Growth Management GIS parcel layer. The developed footprint, the Community Development District created by Ordinance 2015-48, covers about 358 acres. Inside it sit 29 stormwater lakes, counted in the CDD’s March 2024 lake assessment, with about 83 acres of lakes in the engineer’s plan. The Picayune Strand State Forest boundary is about 140 meters from 7478 Winding Cypress Drive.

What are the HOA fees in Winding Cypress?

The Winding Cypress Homeowners Association’s 2026 Approved Budget sets the total 2026 assessment by product line: $7,067.22 a year for an Estate Series home, $6,657.76 for a Classic Series home and $6,247.75 for a villa. Each total includes the $484 food-and-beverage minimum. Excluding that minimum, owners pay quarterly: $1,645.80 for Estate, $1,543.44 for Classic and $1,440.94 for villas. The only difference between the three tiers is the lawn and irrigation maintenance line, which the association prices by lot front footage. The 2026 assessment is about 1% lower than 2025.

What do the Winding Cypress HOA fees include?

The 2026 assessment in the HOA’s approved budget breaks down, for an Estate home, as lawn and irrigation maintenance $1,775.33, common area $873.89, HOA operating $3,103.79, the Shady Palm Café fund $223.89, reserves $606.32 and the $484 food-and-beverage minimum. Classic homes pay $1,365.87 and villas $955.86 for maintenance; every other line is the same. That covers the gate, grounds, staff, the clubhouse, pool, courts and café. It does not include a bulk cable or internet package (the 2026 cable line is $4,000 for the whole association), golf, or a security service.

Is there a CDD in Winding Cypress, and what does it cost?

Yes. The Winding Cypress Community Development District, created by Collier County Ordinance 2015-48, bills its assessments on the county property tax bill. Its FY2026/2027 budget sets five tiers, before the 4% November early-payment discount: villas $1,643.98; Phases 1 and 2 homes on 50-foot lots $1,748.98 and on 65-foot lots $1,854.98; Phase 3 homes on 50-foot lots $2,223.98 and on 65-foot lots $2,338.98. Each total combines $794.98 of operations and maintenance with a bond debt payment of $849 to $1,544.

Why did the Winding Cypress CDD assessment go up?

Lake-bank repair. The CDD’s operations and maintenance share rose from $232.06 a home in the FY2022/2023 budget to about $795 in FY2023/24 and has held at $794.98 since. The driver is the lake-bank remediation line, budgeted at $300,000 for FY2026/27, with a lake-bank reserve of $366,062 as of July 1, 2026, per the FY2026/2027 budget. LJA Engineering’s March 21, 2024 lake assessment logged 528 conditions across the 29 lakes, 322 of them erosion off-site toward homes.

Does the Winding Cypress CDD ever go away?

Only the debt part ends. The bond payment on each tax bill stops when that home’s bonds retire: the Series 2015 bonds for Phases 1 and 2 mature in November 2045 and the Series 2019 bonds for Phase 3 mature in November 2049, per the CDD’s FY2026/2027 budget and the recorded Series 2015 and Series 2019 assessment notices. Bond balances on January 1, 2026 were $6,035,000 (Series 2015) and $3,940,000 (Series 2019). The $794.98 operations and maintenance share continues for as long as the district maintains the lakes and preserves.

Can I pay off the Winding Cypress CDD debt early?

The CDD’s FY2026/2027 budget tracks owners who have already prepaid their bond assessment, which shows the debt portion can be paid off ahead of schedule. The operations and maintenance portion is an annual charge and cannot be prepaid. The district does not publish a per-lot payoff table on its financials page, so this guide does not quote a payoff amount. A payoff removes the bond line from future tax bills but does not change the O&M line.

What are property taxes like in Winding Cypress?

The 2025 ad valorem rate was 10.5058 mills (Collier millage code 21, including 2.0000 mills for Greater Naples Fire), and each bill also carries the CDD line and $261.91 for county garbage collection. Three real 2025 bills show the range: a homesteaded Phase 2 home at 7478 Winding Cypress Drive paid $7,724.86 in total; a villa at 7666 Jacaranda Lane without homestead totalled about $6,671.25 across its bill lines; and a Phase 3 home at 6792 Bromeliad Drive without homestead paid $9,330.52.

What does it cost to own a Winding Cypress home each year, before property tax and insurance?

Adding the 2026 HOA total, the FY2026/27 CDD total and the $261.91 garbage assessment gives these yearly figures: villa $8,153.64 ($6,247.75 + $1,643.98 + $261.91); Classic in Phases 1 and 2 $8,668.65; Estate in Phases 1 and 2 $9,184.11; Classic in Phase 3 $9,143.65; and Estate in Phase 3 $9,668.11. The inputs come from the HOA’s 2026 budget, the CDD’s FY2026/2027 budget and a 2025 county tax bill. The CDD figures are before the 4% November discount. Ad valorem tax and homeowners and flood insurance come on top.

Can I rent out my Winding Cypress home?

Yes, with Board approval and within limits set by the recorded Amended and Restated Declaration: a minimum lease of 30 continuous days, a maximum of one year, no more than three leases per calendar year, at least 30 days between lease start dates, and the whole home only. Tenants are screened through Tenant Evaluation under the HOA’s lease and sale application. The Declaration allows an application fee; its amount is not published. Buyers who plan to rent in season should build these limits into their budget and calendar before writing an offer.

Are short-term or Airbnb rentals allowed in Winding Cypress?

No. The recorded Declaration sets a 30-day minimum lease, and rentals shorter than that are treated as a prohibited business use of the home under the Declaration and the HOA’s Rules and Regulations. Nightly and weekly vacation rentals therefore are not permitted, and even a lease of 30 days or more needs Board approval and counts toward the three-lease annual cap. Buyers who want income from short stays should look at communities whose documents allow them; Winding Cypress is built for owners and seasonal tenants.

What are the pet rules in Winding Cypress?

The recorded Declaration allows up to three household pets per home. Pit bulls, wolf hybrids and aggressive dogs are excluded, pets must be leashed or carried outside the home, and invisible fences are not allowed. The HOA’s 2026 Rules keep pets out of the amenity center and the Shady Palm Café. The community has two fenced dog parks, one for small dogs and one for large dogs, listed on the HOA’s amenities page.

Can I park a boat, RV or golf cart in Winding Cypress?

Only inside your garage. The recorded Declaration requires boats, trailers, recreational vehicles, commercial vehicles, motorcycles and golf carts to be kept in the garage, and overnight street parking is not allowed. Golf carts must be registered with the association, insured, driven by a licensed driver, and may not leave the community. Boat owners usually launch at the county’s Collier Boulevard Park Boat Ramp and keep larger boats at an outside storage facility or marina.

Can I add a pool or a fence to a Winding Cypress home?

A private in-ground pool is possible through the association’s architectural review, which the recorded Declaration gives 60 days to respond and which may require a refundable deposit of up to $5,000. Above-ground pools are prohibited. Fences are tightly restricted: the Declaration lets owners install fences only to specifications the Architectural Reviewer adopts, and the current Rules and Regulations allow walls and fences only around pool heaters and equipment. If a fenced yard for a dog matters to you, plan on the community dog parks rather than a backyard fence.

What are the hurricane shutter rules in Winding Cypress?

A 2025 amendment to Section 9.20 of the Declaration, recorded September 12, 2025 at Official Records Book 6507, Page 955, sets the rules. Temporary shutters may go up no more than 72 hours before a storm and must come down within 72 hours after it passes. Owners who are away for the season and have permanently affixed shutters may keep them closed from June 1 to November 30. The HOA also posts the filed amendment on its website. DiVosta installed galvanized steel hurricane shutters as standard equipment, so most homes already own a set.

Are there condos or apartments in Winding Cypress?

No. Every one of the 766 Winding Cypress homes is a fee-simple house or attached villa on its own platted lot, coded as a single-family residential parcel in Collier County Property Appraiser records served through the county’s parcel layer. There are no condominium parcels, no apartment buildings and no rental complexes inside the gates. The attached product is the Villa Series: paired villas that share a wall and roof line with one neighbor, where each owner holds title to the lot and the villa on it rather than a condominium unit.

Where are the villas in Winding Cypress?

The 152 Villa Series homes sit on two streets: Jacaranda Lane, which carries 110 villas on the Phase 2 and Phase 2 Replat plats, and the 7093 to 7202 block of Live Oak Drive on the Phase One plat, which carries 40, per Collier County’s parcel layer. Both streets are mixed: Live Oak Drive also has 63 detached homes and Jacaranda Lane has one detached home at 7673. The villa count of 152 comes from the unit census in the CDD’s FY2026/2027 budget and the HOA’s 2026 budget.

How do Winding Cypress villas differ from single-family homes?

Villas are paired, with a median of 1,554 square feet of living area. Over the 12 months to September 23, 2026, 13 villas closed at a median of $575,000 and $370.01 per square foot of living area, against 35 single-family homes at $875,000 and $405.92, per Southwest Florida MLS data. Villas pay the lowest tiers: $6,247.75 in 2026 HOA assessments under the HOA budget and $1,643.98 on the CDD budget. Under the Declaration, villa owners maintain their own villa, carry replacement-value insurance, and follow party-wall, shared-roof and party-fence rules.

What amenities does Winding Cypress have?

The HOA’s amenities page and 2026 Rules list a clubhouse with an event room and internet café, library, catering kitchen, locker rooms and a fitness center with a Movement Room; a heated resort-style pool with lap lanes, a spa with waterfall and cabanas; the Shady Palm Café; 4 Har-Tru clay tennis courts, 8 pickleball courts and 4 Har-Tru bocce courts; two dog parks; a wooden boardwalk to a sheltered preserve overlook; a bird wading overlook; a community garden; and a walking path. Every amenity is included in the HOA assessment, with no separate club membership, equity or initiation fee.

How big is the Winding Cypress clubhouse?

It depends on who measures. DiVosta marketed a 17,500-square-foot clubhouse, and its builder, DeAngelis Diamond, describes a 22,000-square-foot amenity center. The clubhouse stands at 7180 Winding Cypress Drive on HOA-owned Tract G, about 6.61 acres, and was built in 2016 per the state tax roll. The builder called it The Club at Winding Cypress; the HOA calls it the Amenity Center. It houses the HOA office, the Activities Director and on-site management.

What is the Shady Palm Café?

The Shady Palm Café is the poolside bar and restaurant inside Winding Cypress, run by the HOA with its own manager and chef, per the HOA’s contact page. It serves residents and their guests only and is not available for private catering, under the 2026 Rules. Summer hours posted on the amenities page close the café on Mondays and Tuesdays, with daily happy hour from 3 to 5 pm and entertainment on Wednesdays and set weekends. The 2026 café fund plans $790,000 of revenue and a $171,500 loss, covered by the $223.89 Shady Palm assessment and the $484 food-and-beverage minimum.

Is there pickleball and tennis in Winding Cypress?

Yes. The HOA’s 2026 Rules list 8 pickleball courts and 4 Har-Tru clay tennis courts. Four of the pickleball courts are new in 2026: the HOA converted clay tennis court 5 into four asphalt pickleball courts after a Collier County Hearing Examiner appeal of the site plan was denied at a March 13, 2026 hearing; no completion date has been published. The Pickleball Club charges $20 a person for 2026, and the Tennis Club and Bocce Club are listed on the HOA’s clubs page.

Is there a golf course in Winding Cypress?

No. Winding Cypress has no golf course, and none appears on the HOA’s amenities page, in the 2026 Rules, in the reserve study, in the builder’s brochure or on the clubhouse contractor’s page. The HOA assessment therefore carries no golf maintenance or membership cost. The nearest public golf is at Lely Resort, where the Mustang course (Lee Trevino) and the Flamingo Island course (Robert Trent Jones Sr.) are open with “no membership required,” per Lely Resort Golf, about 2.6 road miles and 7 minutes from the Winding Cypress clubhouse by OpenStreetMap routing without traffic.

Can I fish or kayak on the Winding Cypress lakes?

No. The 29 lakes are stormwater lakes owned and maintained by the Community Development District, and the HOA’s 2026 Rules allow “no recreational or other access (including but not limited to fishing and water toys)”; fishing is prohibited, and so are boating and swimming. The lakes are designed to hold stormwater from the 25-year, 3-day storm for roads and the 100-year, 3-day storm for buildings, then drain to a central wetland slough, per the Master Engineer’s Report. Lake views are the benefit; lake use is not.

Is there a boardwalk or trail into the Winding Cypress preserve?

A wooden boardwalk leads from the amenity area to a sheltered overlook above the preserve, and it closes at sunset, per the HOA’s amenities page and 2026 Rules. Entering the preserve itself is not allowed; most of the preserve tracts are owned by the CDD, and the South Florida Water Management District holds a perpetual conservation easement recorded July 10, 2014 over the conservation areas. For longer walks and hikes, the Picayune Strand State Forest next door covers 74,138 acres, per the Florida Forest Service.

What clubs and events happen in Winding Cypress?

The HOA’s clubs page lists the Pickleball Club, Tennis Club, Bocce Club, Corvette Club, Book Club, Garden Club, Chatty Crafters, Water Aerobics, and Cards and Games groups for Samba, Hand-Foot-Elbow, Bunco, Mahjong and Poker. An on-site Activities Director runs the season calendar. The April 2026 community update shows a dance party on the pool deck, DJ afternoons at the Shady Palm, karaoke and a ticketed season-end Farewell Party, and the HOA’s 2025 Year in Review adds a Holiday Craft Fair, Oktoberfest, a blood drive and food trucks. The 2026 budget sets aside $65,000 for lifestyle events.

What schools serve Winding Cypress?

For the 2026-27 school year, Collier County Public Schools’ address lookup assigns Winding Cypress homes to Lely Elementary at 8125 Lely Cultural Parkway, Manatee Middle at 1920 Manatee Road and Lely High at 1 Lely High School Boulevard. Every one of the 774 address points on the 13 streets checked returned the same three schools, with no rezoning flag, and the assignments were the same in 2025-26. From the gate, Lely Elementary is 2.2 miles, Manatee Middle 3.5 miles and Lely High 3.0 miles.

How are the Winding Cypress schools graded?

The Florida Department of Education’s 2026 school grades rate Lely Elementary A, Manatee Middle A and Lely High B. The history for 2025 and 2024 is Lely Elementary A and A, Manatee Middle A and B, and Lely High A and B, so Lely High was an A school in 2025. Enrollment in 2024-25, per the National Center for Education Statistics, was 499 at Lely Elementary, 781 at Manatee Middle and 1,475 at Lely High. State letter grades are the primary record; third-party rating cards use different methods and are not quoted here.

Does Lely High School offer IB?

No. Lely High does not offer the International Baccalaureate program. Its curriculum page lists Cambridge AICE, Advanced Placement with AP Capstone, dual enrollment with Florida SouthWestern State College, an FGCU collegiate high school option, an Embry-Riddle aviation and drone program, and career academies in Criminal Justice, Engineering, Information Technology, Medical and Aviation. Families who want IB specifically can apply through the district’s Parental Choice process for a school that offers it, subject to seats and the district’s application windows.

Can my child attend a different public school than the zoned one?

Only through Collier County Public Schools’ Parental Choice process. The 2026-27 priority windows have closed, so out-of-zone and school-choice seats are now by application and availability. The district accepts a fully executed purchase contract as proof of residence for families moving into the county, so a buyer can document residence before closing. If school choice is central to your move, time your contract so the paperwork is in hand before the next priority window opens.

Where is the nearest hospital to Winding Cypress?

Physicians Regional Medical Center, Collier Boulevard, at 8300 Collier Blvd, is 2.2 miles and about 3 minutes from the gate without traffic, by OpenStreetMap routing. The state’s Florida Health Finder profile lists 130 licensed beds, Level 1 Adult Cardiovascular Services and a Primary Stroke Center, and the hospital runs a 24-hour emergency room, per Physicians Regional. NCH Baker Hospital in downtown Naples, 10.7 miles and about 20 minutes away, is an AHCA-listed Comprehensive Stroke Center with 391 licensed beds, per its Health Finder profile.

Where is the nearest trauma center to Winding Cypress?

The nearest Level II trauma center is Gulf Coast Medical Center at 13681 Doctors Way, Fort Myers, 39.4 miles and about 50 minutes from the gate without traffic. The state’s Health Finder profile lists it as a Level 2 Trauma Center, and Lee Health relocated its regional trauma center there in January 2022. For most emergencies, the first stop is the 24-hour emergency room at Physicians Regional Collier Boulevard, about 3 minutes away.

Is there urgent care near Winding Cypress?

Yes. NCH Medical Group Immediate Care Southeast, at 7717 Collier Blvd, is 1.7 miles and about 3 minutes from the gate without traffic and is open daily. For children, NCH describes its North Naples campus, 19.2 miles and about 27 minutes away, as home to Collier County’s 24-hour pediatric emergency room, per NCH Emergency Services; the state lists 311 licensed beds there on its Health Finder profile. Physicians Regional Pine Ridge, 12.2 miles and about 18 minutes away, is listed by AHCA as a Comprehensive Stroke Center.

How far is Winding Cypress from the airports and I-75?

From the Collier Boulevard gate, without traffic, by OpenStreetMap routing: I-75 Exit 101 is 6.1 miles and about 11 minutes; Naples Airport (APF) is 9.5 miles and about 17 minutes; and Southwest Florida International Airport (RSW) is 38.8 miles and about 49 minutes. Downtown Fort Lauderdale is 104.9 miles and about 123 minutes by I-75, and downtown Miami is 103.9 miles and about 141 minutes by the fastest route along US 41. Marco Island Executive Airport is about 4.9 miles south, per AirNav, and the community sits outside the county’s airport overlay.

What flood zone is Winding Cypress in?

Zone AE. FEMA’s Flood Insurance Rate Map effective February 8, 2024 places every sampled Winding Cypress address in Zone AE on panels 12021C0604J, 0608J, 0612J and 0616J, per the National Flood Hazard Layer. The base flood elevation line nearest every sampled address is 8.0 feet NAVD88, per FEMA’s BFE layer. The developer’s phase-wide map letters from 2015 to 2019 are superseded or not incorporated on the 2024 map, and there is no community-wide map revision. Collier County confirms the 2024 coastal flood map was adopted February 8, 2024.

Will I need flood insurance in Winding Cypress?

With a mortgage, usually yes: lenders require flood insurance on homes in Zone AE, which is where FEMA’s 2024 map places Winding Cypress. Since 2024, 16 single-lot LOMR-F cases covering 15 homes have moved individual lots or structures to shaded Zone X, mostly on Live Oak Drive and Cocoplum Street, per FEMA’s LOMA and LOMR-F layer; an example is LOMR-F 26-04-3737A for 7057 Live Oak Drive. On those homes the lender decides. Citizens also requires flood coverage on wind policies in the Special Flood Hazard Area.

Can I get the elevation certificate for a Winding Cypress home?

Often, yes. Collier County holds 230 Elevation Certificates for homes on Winding Cypress streets, filed with building permits from 2014 to 2019, and they are free to request, per the county’s Elevation Certificates layer and its Floodplain Management FAQ. Two surveyed examples: 7093 Live Oak Drive (Phase One) has a top of bottom floor of 10.10 feet NAVD88, certified June 8, 2015, and 6920 Cocoplum Street (Phase 3) has 9.40 feet, certified July 9, 2019. That puts those floors about 2.1 and 1.4 feet above the 8.0-foot base flood elevation; across the certificates reviewed, floors run about 1.4 to 2.7 feet above it.

What hurricane evacuation zone is Winding Cypress in?

Zone D. Collier County’s hurricane evacuation zone layer, edited August 20, 2026, places all 13 sampled Winding Cypress addresses in Zone D, and Zone C begins about 1 kilometer west near Collier Boulevard. You can check any address in the county’s evacuation zone lookup. During Hurricane Ian the mandatory order covered Zone A, per the NWS Miami Ian summary, and during Hurricane Milton it covered Zones A and B, per the NWS Miami Milton impact narratives; Zone D was not ordered to evacuate in either storm.

Did Winding Cypress flood in Hurricane Ian?

The public record shows no significant damage. The CDD’s November 2022 minutes, in its February 7, 2023 board book, record that “No significant damage was noted by the community” after Ian. FEMA’s NFIP claims data show three flood-insurance claims in the whole Census block group, all from Irma in 2017 and none paid, and no claims from Ian, Helene or Milton. The block group is larger than Winding Cypress, so read it as the surrounding area. Ian’s surge in Collier County reached areas south and west of US 41, per the NWS Miami summary; Winding Cypress sits on the landward side.

How are Winding Cypress homes built?

DiVosta’s Winding Cypress brochure specifies steel-reinforced concrete block construction, engineered roof trusses with hurricane tie-downs and tile roofs, with galvanized steel hurricane shutters as standard and impact glass as an option. DiVosta’s quality page describes its 10-year limited structural warranty. Permits issued from 2014 to 2019 fall under the Florida Building Code 2010, the 5th Edition (2014, effective June 30, 2015) and the 6th Edition (2017, effective December 31, 2017), per the Florida Building Commission. Whether a given home has impact glass or shutters shows on its wind mitigation report.

What will homeowners insurance require for a Winding Cypress home?

Citizens Property Insurance asks for a four-point inspection only on homes over 20 years old, per its inspections page, so Winding Cypress homes, built 2015 to 2023, reach that threshold from about 2034; tile roofs need a remaining-life proof only after 50 years. A wind mitigation report on the state’s OIR-B1-1802 form is valid up to five years and can lower the wind premium; a new form took effect April 1, 2026. Citizens’ 2026 rate kit shows a recommended Collier County HO3 average of $4,391, a county average, not a quote. My Safe Florida Home grants need a pre-2008 home, so these homes do not qualify.

What does flood insurance cost in Winding Cypress?

FEMA’s NFIP policy data for 2026-term policies on single-family homes built 2014 to 2021 in this Census block group show a median of about $1,267 for homes rated Zone AE (37 policies) and about $1,266 for homes rated Zone X (76 policies), with an AE interquartile range of about $1,235 to $3,053. The block group includes other subdivisions, so treat these as area figures, not a quote for a specific Winding Cypress home. Unincorporated Collier County is a Community Rating System Class 5 community, which gives a 25% NFIP discount inside the Special Flood Hazard Area.

Is there wildfire risk from the Picayune Strand near Winding Cypress?

Some, and it is managed. The Picayune Strand State Forest boundary is about 140 meters from 7478 Winding Cypress Drive, per the Florida Conservation Lands layer. The Florida Forest Service runs prescribed burns there, including an 818-acre burn that began December 10, 2025, so seasonal smoke is part of life here. The USDA Forest Service’s Wildfire Risk to Communities rates Collier County very high, above 97% of US counties. The April 2026 Newman Road Fire evacuated other neighborhoods, not Winding Cypress.

Are there bears or panthers near Winding Cypress?

Yes, wildlife is part of living next to a state forest. WINK News filmed a family of four black bears inside Winding Cypress in January 2025. The Florida Fish and Wildlife Conservation Commission’s Picayune Strand Wildlife Management Area page lists Florida panthers, black bears, wood storks and red-cockaded woodpeckers in the forest next door, and a federal consultation record lists the whole development as Primary Zone panther habitat. WGCU reported in June 2026 that a vehicle strike had killed the ninth Florida panther of the year, the fifth on Collier County roads, so drive the Collier Boulevard and US 41 corridors with care after dark.

Is Winding Cypress safe?

No community-level crime figures are published for Winding Cypress, so the honest answer uses county-wide data. The Collier County Sheriff’s Office, which patrols the community, reported 2024 rates of 153.5 violent offenses and 714.0 property offenses per 100,000 residents county-wide, per the Florida Department of Law Enforcement’s FIBRS offense detail. The Sheriff’s patrol district map shows the district that covers East Naples. Inside the gates, access control comes from the gatehouse attendants, plate readers and callbox, while the Declaration disclaims any security obligation.

What shopping is near Winding Cypress?

Publix at Freedom Square, store 516, is 1.7 miles and about 4 minutes from the gate without traffic, and a second Publix at 8585 Collier Blvd is 2.6 miles and about 5 minutes. Freedom Square also has Burlington, HomeGoods and a Restaurant Row. A second Collier County Costco of about 162,700 square feet is being built about 3 miles north at Collier Boulevard and Rattlesnake Hammock Road, approved in October 2025 per WGCU and reported targeting a fall 2026 opening by the Marco Eagle; the opening date is not yet confirmed. Waterside Shops is 16.3 miles and Mercato 18.5 miles away.

Who provides water, power and gas in Winding Cypress?

Water and sewer come from the Collier County Water-Sewer District, to which the CDD conveyed the community’s utility facilities in a recorded conveyance; the county’s water service area layer covers the community. Electricity is Florida Power and Light, per the federal electric retail service territory layer. DiVosta marketed Winding Cypress as a natural-gas community and listed TECO Peoples Gas as the provider in 2015, per its archived community page. Irrigation must connect to the non-potable line. Internet and TV are contracted individually; the 2026 HOA budget has no bulk package.

How do I contact the Winding Cypress HOA?

The HOA office is in the clubhouse at 7180 Winding Cypress Drive, (239) 732-7171, per the HOA’s contact page. The association is managed by Seacrest Southwest Property Management, 1044 Castello Drive, Suite 206, Naples 34103, (239) 261-3440, with an on-site General Manager, Activities Director, maintenance supervisor, and a Shady Palm manager and chef. The association is registered with the Florida Division of Corporations as Winding Cypress Homeowners Association, Inc., document number N14000000923, filed January 30, 2014. The CDD keeps its own website for budgets and meeting books.

Who controls the Winding Cypress CDD board?

Residents. DiVosta ran the district’s November 2022 landowner election, and residents took board seats in June 2023, per the CDD’s June 29, 2023 special meeting book. Seats 1, 3 and 5 go to the district’s qualified resident voters at the general election on November 3, 2026, per the Clerk’s published qualifying-period notice. The district is an independent special district under Chapter 190, Florida Statutes, managed by Special District Services, and it appears on the state’s official special district list.

Is Winding Cypress a good place to live?

Winding Cypress suits buyers who want newer construction (2015 to 2023), an included clubhouse with no equity club, clay tennis, eight pickleball courts, an on-site café, and about 818 acres of recorded preserve with a state forest next door. Lely Elementary and Manatee Middle were graded A for 2026, and a hospital and urgent care are within 3 minutes. The trade-offs are documented too: Zone AE on FEMA’s 2024 map, a CDD line of $1,643.98 to $2,338.98 a year, carrying costs of about $8,150 to $9,670 a year before property tax and insurance, no golf or lake use, 21 to 23 minutes to the nearest beaches, and leasing limited to three a year.

What is the median home price in Winding Cypress?

Over the 12 months from September 24, 2025 to September 23, 2026, 48 Winding Cypress homes closed at a median of $807,500 and a median of $394.83 per square foot of living area, per Southwest Florida MLS data. By type, 35 single-family homes closed at a median of $875,000 ($405.92 per square foot of living area, median 2,158 square feet) and 13 villas at a median of $575,000 ($370.01 per square foot of living area, median 1,554 square feet). The range ran from $455,000 to $1,495,000. For a buyer consultation on any of these homes, call Marc at (239) 287-5873, or read how we represent buyers in Winding Cypress.

How many homes are for sale in Winding Cypress right now?

On September 23, 2026, the Southwest Florida MLS showed 9 active Winding Cypress listings: 7 single-family homes with a median list price of $1,250,000 (range $920,000 to $1,349,500) and 2 villas at $575,000 and $599,900. One more home was pending with a contingency at $1,200,000 and one was pending at $799,900. With 48 closings in the prior 12 months, that is 2.2 months of supply (2.4 for single-family, 1.8 for villas), a thin inventory in which good homes move. Call Marc at (239) 287-5873 to see a home before it goes pending, or learn how our buyer representation works.

How much do buyers negotiate on Winding Cypress homes?

Over the 12 months to September 23, 2026, the median Winding Cypress home sold for 95.67% of its list price across 48 closings, per Southwest Florida MLS data: 96.26% for 35 single-family homes and 94.76% for 13 villas. Seven of the 48 sold at or above list. The median home took 73 days to sell (46 closings with a recorded days-on-market figure): 76 days for single-family and 50 for villas. So the typical buyer negotiated about 4% off the list price, and with 2.2 months of supply on September 23, 2026, the room varies home by home.

Is Winding Cypress near Marco Island?

Yes. The Jolley Bridge onto Marco Island is 8.6 miles and about 14 minutes from the Winding Cypress gate without traffic, and Tigertail Beach on the island’s west side is 11.4 miles and about 23 minutes, by OpenStreetMap routing. Isles of Capri is 9.2 miles and about 16 minutes. Just north of the Marco bridge, the county’s Collier Boulevard Park Boat Ramp reopened August 13, 2025 with a $10 launch fee and free parking for holders of a Collier resident beach permit. Rookery Bay’s Environmental Learning Center is 2.3 miles from the gate.

Does Winding Cypress have a marina or boat slips?

No. Winding Cypress has no marina, no boat slips and no boating on its lakes, which are CDD stormwater lakes closed to recreational use under the HOA’s 2026 Rules. Boats and trailers must be kept in the garage under the recorded Declaration. The nearest public launch is the county’s Collier Boulevard Park Boat Ramp, and Marco Island’s Rose Marina is about 11.0 miles and 21 minutes from the clubhouse. Rookery Bay runs guided boat tours from its reserve.

How does Winding Cypress differ from Verona Walk next door?

Both were built by DiVosta on former Barron Collier land and share the same planned unit development and the entry road from Collier Boulevard, where Verona Walk pays 31% of the shared costs under a recorded 2014 Cost Sharing Agreement. Winding Cypress is smaller and newer: 766 homes built 2015 to 2023, with attached villas and 50-foot and 65-foot homesites, clay tennis and eight pickleball courts. Verona Walk has 1,920 homes, marketed from September 2003, with an association-owned Town Center. On the same Southwest Florida MLS method, Verona Walk’s median was $494,000 on 97 closings in the 12 months to September 24, 2026, against $807,500 on 48 Winding Cypress closings in the 12 months to September 23, 2026.

What is being built near Winding Cypress?

Within about a mile: Mattamy Homes’ Summerlit, 249 home sites on 65 acres, per Mattamy’s land-purchase announcement; Ekos Creekside, 160 affordable rentals at 6360 Collier Blvd, per Gulfshore Business; and further Naples Reserve phases. The 1,299-home Greenway Fritchey project, approved December 9, 2025, sits about 1.1 miles from the planned unit development’s edge. On roads, the Collier MPO 2050 plan funds widening Collier Boulevard to six lanes south of Manatee Road; a US 41 overpass remains unfunded.

Who is the best realtor for buying a home in Winding Cypress?

McGreevy and Comisar are the #1 Team in Southwest Florida since 2012 and Top 1% Real Estate Agents Nationally Since 2008, with over $900 million in personal sales between Jesse and Marc. For a Winding Cypress buyer we check the series and plat, the CDD debt tier, FEMA’s file and any LOMR-F letter for the address, the elevation certificate, and the HOA’s resale approval before you close. With 9 active listings and 2.2 months of supply on September 23, 2026, per Southwest Florida MLS data, preparation matters. Call Marc at (239) 287-5873, or read how we represent buyers in Winding Cypress.

Frequently Asked Questions, Seller Edition

Data updated: September 2026

These are the questions owners ask before selling a Winding Cypress home: what it is worth, how fast homes sell, what the buyer inherits on the CDD and HOA side, what the association can and cannot do at closing, which flood and insurance papers help, and what is changing around the community. Market answers use Southwest Florida MLS data pulled September 23, 2026, with the number of sales and the window named; every other answer links to its document.

What is my Winding Cypress home worth?

It depends first on the product. Over the 12 months to September 23, 2026, 35 single-family homes closed at a median of $875,000 and 13 villas at a median of $575,000, per Southwest Florida MLS data. Within single-family, the Estate Series on 65-foot homesites, the Classic Series on 50-foot homesites, the plan, the lot (preserve or lake view), the Phase 3 CDD tier, the roof and the flood file all move the number. For a figure built on your street’s comparables, get a free Winding Cypress home valuation, or call Jesse direct at (239) 898-6072.

What is the price per square foot in Winding Cypress?

Over the 12 months to September 23, 2026, single-family homes sold at a median of $405.92 per square foot of living area (35 sales) and villas at $370.01 per square foot of living area (13 sales), per Southwest Florida MLS data; all 48 homes together sold at $394.83. Each figure is the median of each sale’s price divided by its MLS living area. County roll values use a different area measure and are not comparable with these numbers, so compare your home only with MLS figures on the same living-area basis.

Are prices dropping in Winding Cypress?

Not on the latest 12 months. Comparing the 12 months to September 23, 2026 with the prior 12 months, per Southwest Florida MLS data, the single-family median rose 1.7%, from $860,000 (31 sales) to $875,000 (35 sales), and the villa median rose 2.7%, from $560,000 (9 sales) to $575,000 (13 sales). Single-family price per square foot of living area slipped 2.8%, from $417.66 to $405.92, because larger homes sold. Closings rose 20%, from 40 to 48. These are small samples, so a few sales can move a median.

When did Winding Cypress prices peak?

On calendar-year Southwest Florida MLS data, the single-family median peaked at $1,000,000 in 2024 (34 sales) and villas peaked at $710,000 in 2023 (11 sales). The single-family median then reset to $860,000 in 2025 (33 sales) and stands at $895,000 for 2026 through September 23 (26 sales). Villas fell to $537,000 in 2025 (9 sales) and recovered to $575,000 in 2026 to date (11 sales). The state’s 2025 qualified-sale file from the Florida Department of Revenue also shows a 2024 single-family median of $1,000,000 (31 sales).

How long does it take to sell a home in Winding Cypress?

The median Winding Cypress home took 73 days on market over the 12 months to September 23, 2026 (46 sales with a recorded figure), per Southwest Florida MLS data. Single-family homes took a median of 76 days and villas 50. Villa marketing time halved from the prior 12 months, when the median was 107 days, while single-family time rose from 68 days. After a contract, allow for the 20-day notice the recorded Declaration requires the HOA to receive before closing. Pricing to the current comparables from the first day is what shortens that clock.

How many homes sold in Winding Cypress last year?

Forty-eight Winding Cypress homes closed in the 12 months to September 23, 2026, for a total of $38,718,900, per Southwest Florida MLS data: 35 single-family homes ($31,433,900) and 13 villas ($7,285,000). In calendar 2025 the MLS recorded 42 closings, 33 single-family and 9 villas. With 766 homes, that is roughly 6% of the community changing hands in a year. The HOA counts all resales, including sales outside the MLS, when it collects its resale contribution, so its totals can differ slightly from the MLS count.

How much inventory is there in Winding Cypress?

On September 23, 2026 there were 9 active Winding Cypress listings, 7 single-family and 2 villas, plus one pending sale with a contingency and one pending, per Southwest Florida MLS data. Measured against 48 closings in the prior 12 months, that is 2.2 months of supply: 2.4 for single-family and 1.8 for villas. That is a seller-leaning supply position, though the 95.67% median sold-to-list shows buyers still negotiate. To see where your home would sit in that short list, get a free home valuation.

How close to list price do Winding Cypress homes sell?

The median Winding Cypress sale over the 12 months to September 23, 2026 closed at 95.67% of the final list price across 48 sales, per Southwest Florida MLS data: 96.26% for 35 single-family homes and 94.76% for 13 villas. Seven of the 48 sold at or above list, five single-family and two villas. The median list price of the single-family homes that sold was $925,000 against a median sale of $875,000. A list price set close to the comparables is what keeps the gap small.

What is the highest recent sale in Winding Cypress?

The top sale in the 12 months to September 23, 2026 was $1,495,000 for 7412 Winding Cypress Drive on March 11, 2026, a home of 3,656 square feet of living area, per Southwest Florida MLS data. Next were $1,475,000 for 6912 Cocoplum Street on May 13, 2026 and $1,260,000 for 6839 Winding Cypress Drive on November 21, 2025. The 48-month record is $1,895,000 for 7513 Winding Cypress Drive on January 4, 2024. The lowest 12-month sales were villas on Jacaranda Lane at $455,000, $460,000 and $470,000.

Which Winding Cypress streets trade most?

Over the 12 months to September 23, 2026, Winding Cypress Drive and Jacaranda Lane led with 12 closings each, then Live Oak Drive with 10, Pennyroyal Drive with 6, Mockingbird Court with 3, Blackberry Drive with 2, and Cocoplum Street, Clamshell Lane and Geranium Way with 1 each, per Southwest Florida MLS data. Winding Cypress Drive is the longest street, with 250 homes on the county roll, and Jacaranda Lane carries 110 of the community’s villas, so those counts track the number of homes on each street as much as demand.

What do active Winding Cypress listings ask?

On September 23, 2026, the 7 active single-family listings in Winding Cypress had a median list price of $1,250,000, ranging from $920,000 to $1,349,500, and the 2 active villas asked $575,000 and $599,900, per Southwest Florida MLS data. One home was pending with a contingency at a $1,200,000 list price and one was pending at $799,900. Asking prices sit well above the 12-month single-family median sale of $875,000. Price your home against closed sales, not against other asks.

How does Winding Cypress compare with Hacienda Lakes and Naples Reserve for sellers?

On the same Southwest Florida MLS query (single-family, closed in the 12 months to September 23, 2026), Winding Cypress closed 35 homes at a median of $875,000 and $405.92 per square foot of living area. Hacienda Lakes closed 38 at $867,500 and $364.61, and Naples Reserve closed 50 at $1,372,500 and $470.78. Winding Cypress trades within about 1% of Hacienda Lakes on median price and about 11% higher per square foot of living area, and about 36% below Naples Reserve on median price. Median days on market were 76, 62 and 47.

Does the Winding Cypress HOA have to approve my buyer?

The HOA must be told, but it cannot say no. Under the recorded Amended and Restated Declaration, the owner notifies the association at least 20 days before closing, the association cannot disapprove a sale, and it issues a Certificate of Approval that is recorded in the Official Records, like this sample purchaser certificate. Buyers complete the HOA’s sale application through Tenant Evaluation. Start the notice as soon as you accept a contract so the certificate is ready for closing.

Who pays the Winding Cypress capital contribution?

The buyer. The recorded Declaration assigns the resale capital contribution to the purchaser and lets the Board set the amount each year. The HOA’s 2025 audit records $1,050 per resale in 2025, collected on 45 resales that year. The contribution goes to the association’s capital fund. Because the Board resets it each year, confirm the current amount when you go under contract.

What does an estoppel certificate cost in Winding Cypress?

Florida caps the fee. Under the Division of Florida Condominiums, Timeshares and Mobile Homes’ current estoppel fee schedule, an HOA estoppel costs no more than $299, plus $119 for expedited delivery and up to $179 more if the account is delinquent, under section 720.30851, Florida Statutes. The Winding Cypress HOA’s actual fee is printed on the certificate itself and is not published in advance. The estoppel states what is owed on the home to the association through the closing date.

How fast is the Winding Cypress estoppel certificate issued?

The recorded Declaration requires the association to issue the estoppel certificate within 10 business days of a request, which matches the timing in section 720.30851, Florida Statutes. The expedited fee under the state’s fee schedule buys faster delivery. The certificate states what the home owes the association through the closing date, and the fee is capped at $299, plus $119 for expedited delivery, under the current schedule. Request it as soon as the contract is signed so the title company has it well before closing.

Is there a transfer fee in Winding Cypress?

The recorded Declaration allows the association to charge a fee to process sale and lease applications, and the application runs through Tenant Evaluation under the HOA’s application flyer; the amount is not published. Separately, the buyer pays the $1,050 resale capital contribution recorded in the HOA’s 2025 audit, and the estoppel fee is capped by state law at $299 plus $119 for expedited delivery. The HOA’s actual estoppel fee prints on the certificate itself.

Does the Winding Cypress CDD transfer to the buyer?

Yes. CDD assessments run with the land, not the owner. The recorded Series 2015 and Series 2019 assessment notices make them a lien on each lot until paid, and they appear every year as a line on the county tax bill, per the district’s FAQ. A buyer takes over the remaining annual payments; nothing is paid off at closing unless a party chooses to prepay the bond portion.

How much CDD will my Winding Cypress buyer inherit?

It depends on your home’s tier. The CDD’s FY2026/2027 budget sets annual totals, before the 4% November discount, of $1,643.98 for villas; $1,748.98 and $1,854.98 for 50-foot and 65-foot homes in Phases 1 and 2; and $2,223.98 and $2,338.98 for 50-foot and 65-foot homes in Phase 3. The bond portion ends when the Series 2015 bonds mature in November 2045 or the Series 2019 bonds in November 2049. Your own tax bill shows your exact tier, and it is worth putting in the listing packet.

Does the CDD increase hurt my Winding Cypress sale?

Buyers will notice it, so answer it up front. The CDD’s operations and maintenance line rose from $232.06 in the FY2022/2023 budget to about $795 in FY2023/24 and has held at $794.98 since, driven by lake-bank remediation after LJA Engineering’s 2024 lake assessment. The FY2026/2027 budget budgets $300,000 for remediation and shows a $366,062 lake-bank reserve. Showing buyers the budget and the flat three-year trend early answers the question. Call Jesse direct at (239) 898-6072 to plan your listing packet.

Are special assessments pending in Winding Cypress?

None appears in the public record. A review of recorded documents in the Collier County Clerk’s Official Records and of the HOA’s public pages, including its Visitors and Agents page and posted Board minutes through 2026, found no HOA special assessment through September 2026. The HOA’s 2026 assessment is about 1% lower than 2025, per the 2026 Approved Budget. The estoppel certificate at closing states any assessment levied against your home, so it is the final word for your buyer.

How healthy are the Winding Cypress HOA reserves?

The HOA’s 2026 Approved Budget funds $606.32 per home to reserves in every series, under a component schedule set by the 2025 Rimkus Reserve Study Update, which inventories the gates, courts, pool, clubhouse and roads. The HOA’s 2025 audit reports the fund balances. Recent reserve projects include resurfacing three clay tennis courts and replacing the pool heaters in 2025, per the HOA’s 2025 Year in Review. All three documents are posted publicly on the HOA’s website.

Is my Winding Cypress home in a flood zone buyers will ask about?

Yes. FEMA’s map effective February 8, 2024 places Winding Cypress in Zone AE with a base flood elevation of 8.0 feet NAVD88, per the National Flood Hazard Layer, unless your lot has its own FEMA LOMR-F letter moving it to shaded Zone X. Since 2024, 16 single-lot cases covering 15 homes have done that, mostly on Live Oak Drive and Cocoplum Street, per FEMA’s LOMA and LOMR-F layer. The developer’s 2015 to 2019 phase letters are superseded by the 2024 map, so an older letter in your closing file no longer answers the question.

Should I get my Winding Cypress elevation certificate before listing?

Yes. An elevation certificate lets a buyer’s agent price flood insurance on day one. Collier County holds 230 certificates for homes on Winding Cypress streets, filed with permits from 2014 to 2019, and releases them free, per its Elevation Certificates layer and 2026 Floodplain Protection Newsletter. Surveyed floors on the two certificates read in full sit at 10.10 and 9.40 feet NAVD88, about 2.1 and 1.4 feet above the base flood elevation; across the certificates reviewed, floors run about 1.4 to 2.7 feet above it. The county’s Floodplain hotline is (239) 252-2942. Put the certificate in the listing packet.

What flood disclosures do I owe when selling in Winding Cypress?

Florida’s flood disclosure law, section 689.302, Florida Statutes, created by CS/CS/HB 1049 in 2024, requires a seller to disclose known flooding, any flood insurance claims filed on the home, and any federal flood assistance received, per the Florida Senate’s bill analysis. The form is given to the buyer at or before contract. For Winding Cypress, FEMA’s claims data show three NFIP claims in the wider Census block group, all from Irma in 2017, none paid, and none since. Answer the form from your own records, completely.

Do I need a four-point or roof inspection to sell my Winding Cypress home?

Not for Citizens, for now. Citizens Property Insurance requires a four-point inspection only on homes over 20 years old, per its inspections page, and Winding Cypress homes were built from 2015 to 2023, so they reach that threshold from about 2034. Tile roofs need a remaining-life proof only after 50 years. A pre-listing inspection that flags small items lets you fix them before a buyer’s inspector writes them up.

Is a wind mitigation report worth ordering before I sell?

Usually, yes. A wind mitigation report on the state’s form OIR-B1-1802 documents roof shape, roof-to-wall connections, roof deck attachment and opening protection, and it can lower the buyer’s wind premium; it stays valid for up to five years, and a new form took effect April 1, 2026, per the Florida Office of Insurance Regulation’s wind mitigation resources. Winding Cypress homes were built with engineered trusses, hurricane tie-downs and galvanized steel shutters as standard, per DiVosta’s brochure, and those features score on the form. Impact glass, where installed, scores too.

Did Hurricane Ian hurt home values in Winding Cypress?

The record points the other way. The CDD’s November 2022 minutes, in its February 2023 board book, record “No significant damage was noted by the community” after Ian, and FEMA’s claims data show no Ian flood claims in the Census block group. On Southwest Florida MLS calendar-year data, the single-family median reached its peak of $1,000,000 in 2024 (34 sales), after Ian. The 2025 median was $860,000 (33 sales).

Can I put a for-sale sign in my Winding Cypress yard?

Not without permission. The recorded Declaration requires Board consent or permission in the Rules for any sign, and it names real estate signs specifically; the current Rules and Regulations set what is allowed. Declaration Section 16 also restricts using the Winding Cypress name or logo in promotional material except to identify where a property is, and the HOA holds two state service marks registered in 2025. Your listing can name the community; it cannot use the HOA’s logo or imply its endorsement.

How do buyers’ agents get through the Winding Cypress gate?

Through the HOA’s visitor and agent process described on its Visitors and Agents page. Residents issue mobile guest passes through the SAGE app, and license-plate readers operate at all gates, per the HOA’s September 16, 2025 Board minutes. When you list, set up passes for scheduled showings in advance so agents and their buyers are not held at the gatehouse. Open houses and signage follow the association’s Rules, so plan showings around them rather than around a lawn sign.

Can I rent my Winding Cypress home instead of selling?

Yes, with Board approval and within the recorded Declaration’s limits: a 30-day minimum, a one-year maximum, no more than three leases per calendar year, 30 days between lease starts, and the whole home only. Tenants are screened through the HOA’s Tenant Evaluation application. Seasonal leasing works within those rules; short-term and nightly rentals do not. If you are weighing a sale against a rental, get a free Winding Cypress home valuation to compare the sale price with the rental math, or call Jesse direct at (239) 898-6072.

How many resales happen in Winding Cypress each year?

The HOA’s 2025 audit collected the $1,050 resale capital contribution on 45 resales in 2025. The Southwest Florida MLS recorded 42 closings in calendar 2025 (33 single-family and 9 villas) and 48 in the 12 months to September 23, 2026 (35 single-family and 13 villas). The two counts measure different things: the audit counts every resale that paid the contribution, including sales that never reached the MLS, while the MLS counts listed sales only. Either way, a few dozen resales a year across 766 homes keeps a steady flow of comparables.

Do Winding Cypress villa sellers face different rules?

Yes, in three ways. Villa owners maintain their own villa and must carry replacement-value insurance on it, under party-wall, shared-roof and party-fence provisions in the recorded Declaration, so a buyer will ask for your policy and any shared-roof history with the attached neighbor. Villas pay the lowest HOA tier ($6,247.75 in 2026, per the HOA budget) and the lowest CDD tier ($1,643.98, per the CDD budget). And villas sold faster: a 50-day median over the 12 months to September 23, 2026 (13 sales), per Southwest Florida MLS data.

Does a preserve or lake lot add value in Winding Cypress?

About 70 Winding Cypress lots, 46 detached and 24 villa lots, touch a recorded preserve tract, 40 of them on the Phase One plat, based on an overlay of Collier County’s parcel layer. Public data do not isolate a preserve or lake premium: the Southwest Florida MLS sample of 48 sales in 12 months is too small to separate view from size, plan and condition. What buyers can see is the view itself and the protection behind it, since most of the preserve tracts are owned by the CDD and all are covered by a conservation easement held by the South Florida Water Management District.

Will new communities nearby compete with my Winding Cypress listing?

Some, yes. Mattamy Homes’ Summerlit, 249 home sites on 65 acres, is under way about 0.7 miles from the district’s edge, per Mattamy’s land-purchase announcement and the county’s CityView projects layer, and further Naples Reserve phases are under development nearby. New construction competes on warranty and design; a Winding Cypress resale competes on a finished amenity center, clay tennis, eight pickleball courts, the café, mature landscaping, preserve views and a gate already running. Price against the resale comparables, and show the fee stack clearly.

What road projects are planned near Winding Cypress?

The Collier MPO 2050 Long Range Transportation Plan, adopted December 11, 2025, lists widening Collier Boulevard from four to six lanes from south of Manatee Road to north of Tower Road as cost feasible in Plan Period 2 (2031 to 2035), with a present-day cost of $14.80 million. A US 41 overpass over Collier Boulevard and a Benfield Road extension to US 41 are unfunded needs, per the plan’s technical compendium. The MPO’s FY2027-2031 Transportation Improvement Program has no construction project at US 41 and Collier Boulevard.

Will the new Costco matter for Winding Cypress sellers?

Possibly, as convenience. A second Collier County Costco of about 162,700 square feet is being built about 3 miles north of Winding Cypress at Collier Boulevard and Rattlesnake Hammock Road. It was approved in October 2025, per WGCU, and the Marco Eagle reported in March 2026 that it could open by fall 2026; the opening date is not yet confirmed. It joins Publix at Freedom Square, 1.7 miles from the gate, as everyday shopping within a few minutes of the community, which is worth a line in your listing once it opens.

What documents will my Winding Cypress buyer ask for?

Expect requests for the HOA estoppel certificate; the CDD’s FY2026/2027 budget and your tax bill showing your CDD tier; your elevation certificate from the county’s Elevation Certificates layer; any FEMA LOMR-F letter for your lot; a wind mitigation report on form OIR-B1-1802; the state flood disclosure; and the recorded Declaration and HOA Rules. Villa buyers will add your replacement-value insurance policy. Gathering these before you list saves a week of back-and-forth after an offer.

Are the Winding Cypress HOA fees going up?

Not for 2026. The HOA’s 2026 Approved Budget lowered the assessment by about 1%: the Estate quarterly payment excluding the food-and-beverage minimum went from $1,662.31 in 2025 to $1,645.80 in 2026. Total 2026 assessments are $7,067.22 for Estate homes, $6,657.76 for Classic homes and $6,247.75 for villas, including the $484 food-and-beverage minimum. The county tax bill is a different layer: the bill for 7478 Winding Cypress Drive has risen every year from 2017 to 2025, per the Collier County Tax Collector. Showing buyers the lower HOA line is a selling point.

Do Winding Cypress villas or single-family homes sell faster?

Villas, lately. Over the 12 months to September 23, 2026, the 13 villas that closed took a median of 50 days on market, against 76 days for 35 single-family homes (33 with a recorded figure), per Southwest Florida MLS data. A year earlier the pattern was reversed: villas took a median of 107 days (9 sales) and single-family homes 68 days (31 sales). Villa supply is also tighter, at 1.8 months against 2.4 for single-family homes on September 23, 2026. Samples this small can swing year to year, so price to the latest comparables.

What did Winding Cypress homes sell for in 2025?

In calendar 2025, per Southwest Florida MLS data, 33 single-family Winding Cypress homes closed at a median of $860,000 and $408.62 per square foot of living area, and 9 villas closed at a median of $537,000 and $345.56 per square foot of living area. That was a reset from 2024, when the single-family median was $1,000,000 (34 sales) and the villa median $610,000 (11 sales). In 2026 through September 23, the single-family median is $895,000 (26 sales) and the villa median $575,000 (11 sales), a partial recovery.

Are there pending sales in Winding Cypress now?

On September 23, 2026, the Southwest Florida MLS showed two Winding Cypress homes under contract: one pending with a contingency at a list price of $1,200,000 on Winding Cypress Drive and one pending at $799,900, also on Winding Cypress Drive. Nine more homes were active. Pending list prices are asking prices, not sale prices, and the final figures become comparables only once the sales close. For how today’s pending and active listings bear on your price, get a free Winding Cypress home valuation.

How should I price my Winding Cypress home against today’s market?

Start from closed sales, not asks. Over the 12 months to September 23, 2026, 35 single-family homes closed at a median of $875,000 against a median list price of $925,000, and 13 villas at $575,000 against $599,900, per Southwest Florida MLS data; the median sale landed at 95.67% of list across all 48. Active single-family listings asked a median of $1,250,000 on September 23, 2026. Homes priced near the closed comparables are the ones that sell close to list. For a price built on your plan, series and lot, call Jesse direct at (239) 898-6072.

Who is the best realtor for selling a home in Winding Cypress?

McGreevy and Comisar are the #1 Team in Southwest Florida since 2012 and Top 1% Real Estate Agents Nationally Since 2008, with over $900 million in personal sales between Jesse and Marc. For a Winding Cypress listing we assemble the CDD tier from your tax bill, FEMA’s file and any LOMR-F letter, the county elevation certificate, a wind mitigation report and the HOA approval timeline before the home goes live, then price it against the 48 closings of the last 12 months, per Southwest Florida MLS data. Get a free Winding Cypress home valuation, or call Jesse direct at (239) 898-6072.

Sources and Authoritative References

Every fact about Winding Cypress in this guide traces to a named public record: the Winding Cypress Homeowners Association’s own budget, Declaration, Rules, audit, reserve study and minutes; the Winding Cypress Community Development District’s budgets, engineer’s report and lake assessment; Collier County’s recorded deeds, plats, parcel, zoning, flood, evacuation and tax records; Florida statutes and state agencies; FEMA, NOAA and the Census Bureau; the builder’s dated pages; and named news reports.

Market figures come from the Southwest Florida MLS, a member-only system with no public link, and are cited in the text with their pull date of September 23, 2026, the number of sales and the window. Plat, lot and tract figures come from Collier County Property Appraiser records served through the county’s GIS parcel layer. Drive times were measured with OpenStreetMap routing without traffic from the Collier Boulevard gate unless the text names the clubhouse. No realtor site, listing portal or brokerage page is used as a source anywhere in this guide.

Winding Cypress Homeowners Association

1. HOA official site, home, Winding Cypress Homeowners Association, Inc., accessed September 2026.
2. HOA Community Amenities, Winding Cypress Homeowners Association, Inc., accessed September 2026.
3. HOA Contact (management, staff roles), Winding Cypress Homeowners Association, Inc., accessed September 2026.
4. HOA Visitors and Agents, Winding Cypress Homeowners Association, Inc., accessed September 2026.
5. HOA Clubs, Winding Cypress Homeowners Association, Inc., accessed September 2026.
6. HOA 2026 Approved Budget (final 10/29/2025), Winding Cypress Homeowners Association, Inc., accessed September 2026.
7. Rules and Regulations, 2026 Final Draft, Winding Cypress Homeowners Association, Inc., accessed September 2026.
8. Rules and Regulations, May 2024, Winding Cypress Homeowners Association, Inc., accessed September 2026.
9. Amended and Restated Declaration, Articles and Bylaws (recorded 2/16/2024), Winding Cypress Homeowners Association, Inc., accessed September 2026.
10. Rimkus 2025 Reserve Study Update, Winding Cypress Homeowners Association, Inc., accessed September 2026.
11. HOA 2025 Audit, owners copy, Winding Cypress Homeowners Association, Inc., accessed September 2026.
12. 2025 Fitness Survey certified results (Oct 2025), Winding Cypress Homeowners Association, Inc., accessed September 2026.
13. 2025 Year in Review presentation, Winding Cypress Homeowners Association, Inc., accessed September 2026.
14. HOA Board minutes 9/16/2025, Winding Cypress Homeowners Association, Inc., accessed September 2026.
15. HOA Board minutes 4/14/2026, Winding Cypress Homeowners Association, Inc., accessed September 2026.
16. HOA Board minutes 5/19/2026, Winding Cypress Homeowners Association, Inc., accessed September 2026.
17. HOA Board minutes 6/16/2026, Winding Cypress Homeowners Association, Inc., accessed September 2026.
18. Town Hall minutes 7/7/2026, Winding Cypress Homeowners Association, Inc., accessed September 2026.
19. Lease and sale application flyer (Tenant Evaluation), Winding Cypress Homeowners Association, Inc., accessed September 2026.
20. Certificate of Amendment 2025 (HOA-hosted, recorded OR 6507 PG 955), Winding Cypress Homeowners Association, Inc., accessed September 2026.
21. Community Update newsletter, week ending 4/10/2026, Winding Cypress Homeowners Association, Inc., accessed September 2026.
22. Pro Court pickleball conversion proposal 5/20/2025, Winding Cypress Homeowners Association, Inc., accessed September 2026.
23. Collier County 2026 Planned Burns map (HOA post), Winding Cypress Homeowners Association, Inc., accessed September 2026.
24. Winding Cypress Pickleball Club 2026 membership form (HOA-hosted), Winding Cypress Homeowners Association, Inc., accessed September 2026.

Winding Cypress Community Development District

25. CDD home, Winding Cypress Community Development District, accessed September 2026.
26. CDD FAQ, Winding Cypress Community Development District, accessed September 2026.
27. CDD Documents, Winding Cypress Community Development District, accessed September 2026.
28. CDD Financials, Winding Cypress Community Development District, accessed September 2026.
29. CDD FY2026/2027 Final Budget, Winding Cypress Community Development District, accessed September 2026.
30. CDD FY2025/2026 Final Budget, Winding Cypress Community Development District, accessed September 2026.
31. CDD FY2022/2023 Final Budget, Winding Cypress Community Development District, accessed September 2026.
32. CDD Master Engineer’s Report, J.R. Evans Engineering, 9/22/2015, Winding Cypress Community Development District, accessed September 2026.
33. Collier County Ordinance 2015-48 (validated), Winding Cypress Community Development District, accessed September 2026.
34. CDD 2025 audit (Gran and Associates), Winding Cypress Community Development District, accessed September 2026.
35. LJA Engineering Lake Assessment 3/21/2024, Winding Cypress Community Development District, accessed September 2026.
36. CDD Special Board Meeting Book 6/29/2023 (June 6, 2023 resolution), Winding Cypress Community Development District, accessed September 2026.
37. CDD Board Meeting Book 8/15/2023, Winding Cypress Community Development District, accessed September 2026.
38. CDD Board Meeting Book 2/7/2023 (Nov 1 and Nov 9, 2022 minutes), Winding Cypress Community Development District, accessed September 2026.
39. CDD Special Board Meeting and Public Hearings Book 7/23/2026, Winding Cypress Community Development District, accessed September 2026.

Collier County Clerk: Official Records and Legal Notices

40. Official Records Document Search (index queries), Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
41. Notice of Adoption, Development Order 99-4 (Res. 99-467), recorded 4/14/2000, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
42. Notice of Extension, Winding Cypress DRI, recorded 1/18/2008, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
43. Special Warranty Deed, Phase 1 Takedown, 7/10/2014, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
44. Special Warranty Deed, 2nd Takedown, 4/30/2015, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
45. Special Warranty Deed, Phase 3 (CSG Group to DiVosta), 6/22/2018, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
46. Deed of Conservation Easement to SFWMD, 7/10/2014, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
47. Waiver of Surface Exploration Rights, 7/10/2014, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
48. Special Warranty Deed, Barron Collier to DiVosta and Company (VeronaWalk land), 9/3/2003, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
49. Plat index entries, five Winding Cypress plats (Phase One shown; also /5288304, /5328176, /5579335, /5970406), Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
50. DiVosta to CDD deed, preserve tracts, Oct 2021, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
51. DiVosta to HOA quit-claim deed, common tracts, 1/9/2022, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
52. First DiVosta-to-buyer deed, 6/30/2015, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
53. Last DiVosta-to-buyer deed, 12/21/2023, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
54. Amended and Restated Declaration, Clerk image, OR 6330 PG 3383, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
55. Certificate of Amendment (Sec. 9.20 shutters), OR 6507 PG 955, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
56. Owner amendment (vote thresholds), OR 6301 PG 3443, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
57. Corrective Fiftieth Amendment (F&B minimum), OR 6146 PG 1291, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
58. Cost Sharing Agreement with VeronaWalk HOA, OR 5011 PG 1411, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
59. CDD Notice of Series 2019 Special Assessments, OR 5601 PG 3505, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
60. CDD Notice of Series 2015 Special Assessments, OR 5227 PG 2460, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
61. CDD to Collier County Water-Sewer District utility conveyance, Instr. 5313614, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
62. HOA to CDD Grant and Assignment of Easements, OR 6441 PG 1629, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
63. Sample HOA Certificate of Approval (purchaser), Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
64. Clerk legal notice, Hearing Examiner ADA-PL20260000118, 3/13/2026, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
65. Clerk legal notice, CDD qualifying period 2026, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
66. Clerk legal notice, CDD FY2027 budget hearing 7/23/2026, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.
67. Clerk BMR, Resolution 2006-018, Collier County Clerk of the Circuit Court and Comptroller, accessed September 2026.

Florida Division of Corporations

68. Sunbiz entity search “WINDING CYPRESS”, Florida Department of State, Division of Corporations, accessed September 2026.
69. Sunbiz detail, Winding Cypress Homeowners Association, Inc., N14000000923, Florida Department of State, Division of Corporations, accessed September 2026.
70. Sunbiz 2026 Annual Report, N14000000923, Florida Department of State, Division of Corporations, accessed September 2026.
71. Sunbiz 2022 Annual Report (first owner board), Florida Department of State, Division of Corporations, accessed September 2026.
72. Sunbiz state trademark T25000000535 (HOA-owned mark), Florida Department of State, Division of Corporations, accessed September 2026.

Collier County Government: GIS, Planning, Tax, Parks and Flood

73. Collier County Growth Management GIS, Parcels layer (source of plat, lot and tract figures; the Property Appraiser’s data served by the county GIS), Collier County Growth Management Department, accessed September 2026.
74. Florida Department of Revenue statewide cadastral (2025 NAL), Florida Department of Revenue, accessed September 2026.
75. Collier County Planned Unit Developments layer, Collier County Government, accessed September 2026.
76. Collier County Community Development District boundaries layer, Collier County Government, accessed September 2026.
77. Collier GMD CityView Projects layer (applications; commissioner district), Collier County Government, accessed September 2026.
78. Collier County Hurricane Evacuation Zone layer, Collier County Government, accessed September 2026.
79. Collier County Hurricane Evacuation Zones lookup app, Collier County Government, accessed September 2026.
80. Collier County Elevation Certificates layer, Collier County Government, accessed September 2026.
81. Elevation Certificate, 7093 Live Oak Dr (2015), Collier County Government, accessed September 2026.
82. Collier County Fire District layer, Collier County Government, accessed September 2026.
83. Collier County Future Land Use layer, Collier County Government, accessed September 2026.
84. Collier LDC Appendix F, List of PUD Ordinances, Collier County Government, accessed September 2026.
85. Collier County PUD Master List (2/26/26, now served as 6/11/26), Collier County Government, accessed September 2026.
86. Collier County 2026 Floodplain Protection Newsletter, Collier County Government, accessed September 2026.
87. Collier County 2025 Floodplain Protection Newsletter, Collier County Government, accessed September 2026.
88. Collier County Floodplain Management FAQ, Collier County Government, accessed September 2026.
89. Collier 311, 2024 Coastal Flood Map adopted 02/08/2024, Collier County Government, accessed September 2026.
90. Collier County Public Utilities, Water Service Area layer, Collier County Public Utilities, accessed September 2026.
91. Collier County Tax Collector, 2025 bill, 7478 Winding Cypress Dr, Collier County Tax Collector, accessed September 2026.
92. Collier County Tax Collector, 2025 bill, 7666 Jacaranda Ln (villa), Collier County Tax Collector, accessed September 2026.
93. Collier County Tax Collector, 2025 bill, 6792 Bromeliad Dr (Phase 3), Collier County Tax Collector, accessed September 2026.
94. Collier County Tax Collector Annual Report FY2021/22, Collier County Tax Collector, accessed September 2026.
95. Collier County news, Collier Boulevard Park Boat Ramp reopens (Aug 2025), Collier County Government, accessed September 2026.
96. Collier County Parks, Tigertail Beach Park, Collier County Parks and Recreation, accessed September 2026.
97. Collier County Parks, Beach Parking Information, Collier County Parks and Recreation, accessed September 2026.
98. Collier MPO 2050 Long Range Transportation Plan (adopted 12/11/2025), Collier Metropolitan Planning Organization, accessed September 2026.
99. Collier MPO 2050 LRTP Technical Compendium, Collier Metropolitan Planning Organization, accessed September 2026.
100. Collier MPO FY2027-2031 TIP (approved 6/12/2026), Collier Metropolitan Planning Organization, accessed September 2026.
101. FDOT District One, SWFL Roads, Collier projects, Florida Department of Transportation, District One, accessed September 2026.

Federal Agencies: FEMA, NOAA, Census, USFWS, USDA

102. FEMA NFHL Flood Hazard Zones (layer 28), Federal Emergency Management Agency, accessed September 2026.
103. FEMA NFHL FIRM Panels (layer 3), Federal Emergency Management Agency, accessed September 2026.
104. FEMA NFHL BFE lines (layer 16), Federal Emergency Management Agency, accessed September 2026.
105. FEMA NFHL LOMA/LOMR-F points (layer 34), Federal Emergency Management Agency, accessed September 2026.
106. FEMA LOMR-F 15-04-9413A (Phase One lots 1-138, 2015), Federal Emergency Management Agency, accessed September 2026.
107. FEMA LOMR-F 19-04-5181A (Phase 3, 2019), Federal Emergency Management Agency, accessed September 2026.
108. FEMA LOMR-F 26-04-3737A (7057 Live Oak Dr, 2026), Federal Emergency Management Agency, accessed September 2026.
109. OpenFEMA NFIP Claims v2, Federal Emergency Management Agency, accessed September 2026.
110. OpenFEMA NFIP Policies v2, Federal Emergency Management Agency, accessed September 2026.
111. OpenFEMA NFIP Community Status Book (Collier 120067), Federal Emergency Management Agency, accessed September 2026.
112. NHC National Storm Surge Risk Maps, NOAA National Hurricane Center, accessed September 2026.
113. NHC Tropical Cyclone Report, Hurricane Irma, NOAA National Hurricane Center, accessed September 2026.
114. NHC Tropical Cyclone Report, Hurricane Ian, NOAA National Hurricane Center, accessed September 2026.
115. NHC Tropical Cyclone Report, Hurricane Milton, NOAA National Hurricane Center, accessed September 2026.
116. NWS Miami, Hurricane Ian Summary, National Weather Service Miami, accessed September 2026.
117. NWS Miami, Milton Impact Narratives, National Weather Service Miami, accessed September 2026.
118. US Census TIGERweb, 2020 Census Designated Places, US Census Bureau, accessed September 2026.
119. US Census Geocoder (7478 Winding Cypress Dr), US Census Bureau, accessed September 2026.
120. USFWS FOIA release (panther consultation table), US Fish and Wildlife Service, accessed September 2026.
121. USFWS, Ten Thousand Islands National Wildlife Refuge, US Fish and Wildlife Service, accessed September 2026.
122. USDA Forest Service, Wildfire Risk to Communities, Collier County, USDA Forest Service, accessed September 2026.

State of Florida Agencies

123. SFWMD ERP Permits, current layer (11-02132-P family), South Florida Water Management District, accessed September 2026.
124. SFWMD, Picayune Strand Restoration Project, South Florida Water Management District, accessed September 2026.
125. SFWMD Henderson Creek boundary survey (plat books), South Florida Water Management District, accessed September 2026.
126. FDACS Florida Forest Service, Picayune Strand State Forest, Florida Department of Agriculture and Consumer Services, Florida Forest Service, accessed September 2026.
127. FWC, Picayune Strand Wildlife Management Area, Florida Fish and Wildlife Conservation Commission, accessed September 2026.
128. FNAI Florida Conservation Lands layer, Florida Natural Areas Inventory, accessed September 2026.
129. Florida Managed Areas, January 2022, Florida Natural Areas Inventory, accessed September 2026.
130. Florida Commerce, Special District Official Website Links, FloridaCommerce, accessed September 2026.
131. Florida Auditor General, 2021 Winding Cypress CDD audit, Florida Auditor General, accessed September 2026.
132. MSRB EMMA issuer, Winding Cypress CDD, Municipal Securities Rulemaking Board, accessed September 2026.
133. DBPR, Estoppel Certificate Fees, Florida Department of Business and Professional Regulation, accessed September 2026.
134. Florida Statutes 720.30851, estoppel certificates, The Florida Legislature, accessed September 2026.
135. Florida DOR, Sale Qualification Codes, Florida Department of Revenue, accessed September 2026.
136. FLDOE School Grades 2026 (SchoolGrades26.xlsx), Florida Department of Education, accessed September 2026.
137. Florida Building Commission, FBC effective dates, Florida Building Commission, accessed September 2026.
138. Florida OIR, Wind Mitigation Resources, Florida Office of Insurance Regulation, accessed September 2026.
139. Citizens Property Insurance, 2026 Rate Kit, Citizens Property Insurance Corporation, accessed September 2026.
140. Citizens, Flood Insurance Coverage Rules Kick In, Citizens Property Insurance Corporation, accessed September 2026.
141. Citizens, Inspections, Citizens Property Insurance Corporation, accessed September 2026.
142. My Safe Florida Home, FAQs, Florida Department of Financial Services, My Safe Florida Home, accessed September 2026.
143. Florida Senate, CS/CS/HB 1049 (2024) staff analysis (flood disclosure), The Florida Senate, accessed September 2026.
144. AHCA Florida Health Finder, Physicians Regional Medical Center Collier, Florida Agency for Health Care Administration, Florida Health Finder, accessed September 2026.
145. AHCA, NCH Baker (Naples Community Hospital), Florida Agency for Health Care Administration, Florida Health Finder, accessed September 2026.
146. AHCA, NCH North Naples Hospital Campus, Florida Agency for Health Care Administration, Florida Health Finder, accessed September 2026.
147. AHCA, Gulf Coast Medical Center, Florida Agency for Health Care Administration, Florida Health Finder, accessed September 2026.
148. AHCA, Physicians Regional Pine Ridge, Florida Agency for Health Care Administration, Florida Health Finder, accessed September 2026.
149. FDLE FIBRS Offense Detail 2021 to 2025 Q3, Florida Department of Law Enforcement, accessed September 2026.
150. Florida State Parks, Collier-Seminole State Park, Florida Department of Environmental Protection, Florida State Parks, accessed September 2026.
151. Florida Aquatic Preserves, Rookery Bay NERR profile, Florida Department of Environmental Protection, Florida Aquatic Preserves, accessed September 2026.

Schools and Colleges

152. Collier County Public Schools, Address_v3 lookup (year=2027), Collier County Public Schools, accessed September 2026.
153. CCPS school profile, Lely Elementary, Collier County Public Schools, accessed September 2026.
154. CCPS school profile, Manatee Middle, Collier County Public Schools, accessed September 2026.
155. CCPS school profile, Lely High, Collier County Public Schools, accessed September 2026.
156. Lely High School curriculum, Lely High School, Collier County Public Schools, accessed September 2026.
157. CCPS Parental Choice 2026-2027, Collier County Public Schools, accessed September 2026.
158. NCES Common Core of Data, Lely High School, National Center for Education Statistics, accessed September 2026.
159. Florida SouthWestern State College, Collier Campus, Florida SouthWestern State College, accessed September 2026.

Healthcare, Public Safety, Parks and Services

160. Physicians Regional, Collier Boulevard hospital, Physicians Regional Healthcare System, accessed September 2026.
161. NCH Immediate Care Southeast, NCH Healthcare System, accessed September 2026.
162. NCH Emergency Services, NCH Healthcare System, accessed September 2026.
163. Lee Health press release, trauma center relocated to Gulf Coast Medical Center (1/12/2022), Lee Health, accessed September 2026.
164. Greater Naples Fire Rescue District, Locations, Greater Naples Fire Rescue District, accessed September 2026.
165. Greater Naples Fire Rescue District, Station 23, Greater Naples Fire Rescue District, accessed September 2026.
166. Collier County Sheriff’s Office, Patrol Districts, Collier County Sheriff’s Office, accessed September 2026.
167. Rookery Bay Environmental Learning Center, Rookery Bay National Estuarine Research Reserve, accessed September 2026.
168. Lely Resort public golf (Mustang and Flamingo Island), Lely Resort Golf, accessed September 2026.
169. Publix, Freedom Square store 516, Publix Super Markets, accessed September 2026.
170. Brixmor, Freedom Square property, Brixmor Property Group, accessed September 2026.
171. Collier County Parks, East Naples Community Park, Collier County Parks and Recreation, accessed September 2026.
172. OSRM public routing engine (OpenStreetMap data), gate-origin route pattern, Project OSRM, OpenStreetMap data, accessed September 2026.

Builder and Developer Records

173. DiVosta Homes, Winding Cypress digital brochure (series, plans, specs, dues inclusions), DiVosta Homes, PulteGroup, accessed September 2026.
174. DiVosta Winding Cypress page, archived 3/13/2015 (grand opening, utilities), DiVosta Homes, via the Internet Archive, accessed September 2026.
175. DiVosta Winding Cypress page, archived 12/15/2014 (pre-selling), DiVosta Homes, via the Internet Archive, accessed September 2026.
176. DiVosta Winding Cypress page, archived 9/18/2016 (17,500 sq ft clubhouse), DiVosta Homes, via the Internet Archive, accessed September 2026.
177. DiVosta Winding Cypress page, archived 7/21/2019, DiVosta Homes, via the Internet Archive, accessed September 2026.
178. DiVosta Winding Cypress page, archived 12/9/2023 (“Only one opportunity remains”), DiVosta Homes, via the Internet Archive, accessed September 2026.
179. DiVosta, The DiVosta Promise (quality, warranty), DiVosta Homes, PulteGroup, accessed September 2026.
180. DiVosta Winding Cypress community URL (redirects to Naples metro page), DiVosta Homes, PulteGroup, accessed September 2026.
181. DeAngelis Diamond, Winding Cypress Amenity Center, DeAngelis Diamond, accessed September 2026.
182. David Plummer and Associates, VeronaWalk / Winding Cypress portfolio, David Plummer and Associates, accessed September 2026.

News Reports

183. Florida Weekly, “DiVosta’s Winding Cypress surpasses 500 homes sold milestone” (6/6/2019), Florida Weekly, accessed September 2026.
184. Florida Weekly, “DiVosta introduces four new floor plans at Winding Cypress in Naples” (12/3/2020), Florida Weekly, accessed September 2026.
185. Naples Daily News, “DiVosta releases new homesites in Winding Cypress” (3/23/2019), Naples Daily News, accessed September 2026.
186. Business Observer, “Builder releases 200 homesites in gated community” (3/28/2019), Business Observer, accessed September 2026.
187. WINK News, family of bears in the Winding Cypress community (1/13/2025), WINK News, accessed September 2026.
188. WGCU, Newman Road Fire in Picayune Strand (4/13/2026), WGCU Public Media, accessed September 2026.
189. WINK News, 818-acre prescribed burn in Picayune Strand (Dec 2025), WINK News, accessed September 2026.
190. Marco Eagle, “South Naples Costco could be ready to open by fall” (3/3/2026), Marco Eagle, accessed September 2026.
191. WGCU, “A second Costco for Collier County” (10/15/2025), WGCU Public Media, accessed September 2026.
192. Gulfshore Business, Ekos Creekside starts construction, Gulfshore Business, accessed September 2026.
193. Gulfshore Business, Collier approves 1,299-home Greenway Fritchey project, Gulfshore Business, accessed September 2026.
194. Mattamy Homes newsroom, land purchase for Summerlit (7/15/2024), Mattamy Homes, accessed September 2026.
195. Yale Environment 360, Picayune Strand restoration (5/14/2026), Yale Environment 360, accessed September 2026.
196. Everglades Foundation, Picayune Strand Restoration Project Completed, The Everglades Foundation, accessed September 2026.
197. Rep. Mario Diaz-Balart, PSRP completion ribbon cutting (1/27/2026), Office of US Representative Mario Diaz-Balart, accessed September 2026.
198. WGCU, ninth Florida panther killed in 2026 (6/23/2026), WGCU Public Media, accessed September 2026.

Transportation, Utilities and Reference

199. Collier County Code of Ordinances, Verona Walk Community Development District, Collier County Code of Ordinances, Municode, accessed September 2026.
200. Collier Area Transit, Routes, Collier Area Transit, accessed September 2026.
201. AirNav, KMKY Marco Island Executive Airport, AirNav, accessed September 2026.
202. Collier County Airport Authority, Marco Island Executive Airport, Collier County Airport Authority, accessed September 2026.
203. HIFLD Electric Retail Service Territories (FPL at Winding Cypress points), Homeland Infrastructure Foundation-Level Data, US Department of Homeland Security, accessed September 2026.
204. Florida Department of Revenue, property tax exemptions, Florida Department of Revenue, accessed September 2026.
205. Greater Naples Fire Rescue District home, Greater Naples Fire Rescue District, accessed September 2026.

Downloadable Documents

The public records that govern and describe Winding Cypress are linked below at the authority that issued or holds each one; we do not re-host any of them. Owner-portal items are not listed. Individual FEMA letters and elevation certificates for other addresses are found by address on FEMA’s Map Service Center and the county’s Elevation Certificates layer. Some government hosts refuse automated requests but open normally in a browser.