Sell Your Home in Winding Cypress, FL

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

Why Sell Your Winding Cypress Home With McGreevy and Comisar?

Winding Cypress in East Naples is a gated DiVosta community of 766 homes where 48 sold in the last twelve months and every sale is now a resale. McGreevy and Comisar, Top 1% Real Estate Agents Nationally Since 2008, price by series, plat and flood file, and prepare the association, district and FEMA paperwork before the listing goes live.

This page is written for the owner. If you want the full picture of the community itself, the plats, the club, the flood map street by street and the schools, read our complete Winding Cypress community guide, which this seller guide sits beside, and our wider Naples real estate guide for the city around it. Everything below answers one question: how to sell a home inside the Winding Cypress gates for the most money, with the fewest surprises, on a timeline you control. Call Jesse McGreevy direct at (239) 898-6072 whenever you want to talk it through.

Sell Your Winding Cypress Home With the #1 Team in Southwest Florida Since 2012

Jesse McGreevy and Marc Comisar have been Top 1% Real Estate Agents Nationally Since 2008 and the #1 Team in Southwest Florida since 2012. They personally run the pricing conversation, the marketing build, the negotiation and the association and district paperwork on every listing they take. If you are comparing listing agents across the whole city before you choose one, our guide to the best real estate agents in Naples sets the teams side by side on the public record: reviews, licence history and published production.

The Credentials, Stated Plainly

• 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

Those are career numbers across Lee and Collier County. As the leaders of Domain Realty Group, our team has closed over $2.5 billion in real estate. Learn more about the wider team at DomainRealtyGroup.com.

Our Record Behind This Page

Domain Realty, our brokerage, closed 658 transaction sides in Naples in the 60 months to October 5, 2026, $521.5 million in volume counted by side, per the Southwest Florida MLS pulled that day. McGreevy and Comisar are the #5 real estate team in Florida in the 2026 RealTrends rankings. In the last 12 months we tracked every one of the 48 Winding Cypress closings in the Southwest Florida MLS, set them against Collier County’s recorded sales, and read them against the five recorded plats, the association’s budget and the district’s budget. Every figure below carries its source and its date, and when we sit down with you, the source screens come to the table too.

How We Work a Listing, and Who Actually Does It

You get Jesse and Marc, not an assistant with a template. Marc Comisar runs the field side: showings, buyer agent conversations, contractor coordination, gate registration and inspections. Jesse McGreevy runs pricing, marketing, data and the association, district and flood paperwork. Reach Jesse at (239) 898-6072 or Marc at (239) 287-5873, and read more about the partnership on our about McGreevy and Comisar page.

What Makes Selling in Winding Cypress Different?

Selling in Winding Cypress differs from most Naples sales in four ways: the homes trade as three product lines across five recorded plats, the plat sets the buyer’s district assessment, the association must be told of the sale but cannot block it, and FEMA’s 2024 map places the community in Zone AE, so the flood file travels with every listing.

Data updated: September 2026 (Winding Cypress CDD FY2026/27 budget and HOA 2026 Approved Budget, retrieved 23 Sep 2026)

One Gate, Three Product Lines, Five Plats

Winding Cypress holds 766 homes: 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 on five recorded plats, Phase One, Phase 2, Phase 2C, Phase 2 Replat and Phase 3, holding 153, 245, 23, 143 and 202 homes, per Collier County’s parcel layer. A villa on Jacaranda Lane and an Estate home backing onto preserve on the Phase 3 plat share a gatehouse and a clubhouse, and very little else in how they price.

The Association Must Be Told, but Cannot Say No

Under the recorded Amended and Restated Declaration, recorded in February 2024 at Official Records Book 6330, Page 3383, an owner notifies the Winding Cypress Homeowners Association at least 20 days before closing. The association cannot disapprove a sale; it issues a Certificate of Approval that is recorded in the county’s official records, like this sample purchaser certificate. That is a cleaner path than many Naples clubs offer, and it is still a date that belongs in the contract from the first draft.

The Buyer Pays the Resale Capital Contribution

The recorded Declaration assigns the resale capital contribution to the purchaser and lets the Board set the amount each year. The association’s 2025 audit records $1,050 per resale in 2025, collected on 45 resales that year. The transferee is your buyer, not you, so the contribution belongs on the buyer’s side of the closing statement, and the estoppel certificate is where the current amount is confirmed.

Every Home Is Now a Resale

DiVosta Homes, a PulteGroup brand, recorded its first Winding Cypress sale to a buyer on June 30, 2015 and its last on December 21, 2023, per the Collier County Clerk’s first and last builder deeds. There is no builder inventory competing with your listing inside the gates. Your competition is the handful of other owners selling this season, and new construction outside the gates, which we cover in the pricing section below.

Key Takeaways for a Winding Cypress Seller

• Winding Cypress has 766 homes: 152 attached villas, 406 Classic Series homes on 50-foot homesites and 208 Estate Series homes on 65-foot homesites, built by DiVosta from 2015 to 2023.
• The Southwest Florida MLS recorded 48 closings in the twelve months to September 23, 2026, for $38,718,900: single-family homes at a median of $875,000 and villas at $575,000.
• Homes sold at a median 95.67 percent of list price after a median of 73 days on market, and only 7 of 48 sold at or above list.
• There were 9 active listings on September 23, 2026, about 2.2 months of supply, while active single-family listings asked a median of $1,250,000, well above what the last year of sales supports.
• The association must be told at least 20 days before closing but cannot disapprove a sale, and the buyer pays the resale capital contribution, $1,050 in 2025.
• The district assessment runs $1,643.98 to $2,338.98 a year by product and plat, and homes on the Phase 3 plat carry the higher debt line, which your buyer will compare.
• FEMA’s map effective February 8, 2024 places Winding Cypress in Zone AE with a base flood elevation of 8.0 feet NAVD88, and about 15 homes have their own FEMA letters placing them in shaded Zone X.
• Collier County holds 230 Elevation Certificates on Winding Cypress streets, free on request, and a seller who puts the certificate in the listing file answers the first underwriting question before it is asked.

Is Now a Good Time to Sell in Winding Cypress?

For a well-priced home, yes. The Southwest Florida MLS shows 48 Winding Cypress closings in the twelve months to September 23, 2026, with only nine homes for sale on that date, about 2.2 months of supply. Supply favours sellers, but buyers still negotiate: the median home closed at 95.67 percent of its final list price.

Data updated: September 2026 (Southwest Florida MLS, development name Winding Cypress, pulled 23 Sep 2026)

The Twelve-Month MLS Picture

Every figure comes from one Southwest Florida MLS search on the development name Winding Cypress, which returned one dictionary entry and no neighbouring community to exclude. The single-family and villa split follows the building label each listing agent chose. Price per square foot is each sale price divided by that home’s MLS living area, then the median of those ratios; it is never comparable with a county roll figure measured on a different area basis.

Tight Supply and Real Negotiation Are Both True

Two months of supply is a seller-favourable reading anywhere in Collier County. A median sale to list ratio of 95.67 percent says buyers still take about four percent off the final list price. They are not in conflict. Few Winding Cypress homes are for sale at any moment, so a buyer has little to choose from, but the buyer who does engage has usually toured Verona Walk, Hacienda Lakes and Naples Reserve the same week and knows what each costs to carry. The seller who wins is the one whose first price already survives that comparison.

Asking Prices Have Run Ahead of Sales

On September 23, 2026 the seven active single-family listings in Winding Cypress asked a median of $1,250,000, from $920,000 to $1,349,500, while the 35 single-family homes that sold over the prior twelve months closed at a median of $875,000. That is a gap of about 43 percent between today’s asks and last year’s sales [our arithmetic]. Some of it is mix, since larger Estate homes are over-represented among the active listings, but most of it is optimism. The homes that close are the ones priced against closed sales, not against a neighbour’s asking price.

The County Deed Record Agrees With the MLS

We also ran every recorded Winding Cypress sale through Collier County’s own public files. Counting only DOR-qualified sales of improved homes, from September 2025 through the newest recording in the county’s file, June 19, 2026, Collier County’s recorded sales show 39 qualified sales at a median of $835,000, from $455,000 to $1,495,000. All 39 were resales and none was a first sale from the builder, which matches DiVosta’s last recorded sale in December 2023. The county file ends earlier than the MLS window, so the counts differ, but the range is identical at both ends. Most new homes in builder-heavy communities never reach the MLS; in Winding Cypress the builder has left, the MLS sees the market, and the two independent records tell the same story.

Where Today’s Nine Active Listings Sit

The nine active Winding Cypress listings on September 23, 2026 were seven single-family homes from $920,000 to $1,349,500 and two villas at $575,000 and $599,900. Two more homes were pending, at list prices of $1,200,000 (with a contingency) and $799,900, both on Winding Cypress Drive. Villa supply was the tightest in the community, at 1.8 months, against 2.4 months for single-family homes. That is your live competition, and in a market this thin every one of those homes is a comparable your buyer will tour the same afternoon.

Thinking of Selling Your Winding Cypress Home? Start With a Written Valuation

With 2.2 months of supply, a 95.67 percent median sale to list ratio and asking prices running well ahead of closed sales, the first price you publish is the most important decision of the sale. Request a written opinion of value through our Winding Cypress home valuation request or the McGreevy and Comisar free home valuation, or call Jesse McGreevy direct at (239) 898-6072. Buying instead? See how we represent buyers in Naples or call Marc Comisar at (239) 287-5873.

How Have Winding Cypress Prices Moved Since 2023?

Winding Cypress single-family prices peaked in 2024 at a $1,000,000 median, reset about 14 percent to $860,000 in 2025 and stand at $895,000 for 2026 through September 23, per the Southwest Florida MLS. Villas peaked earlier, at $710,000 in 2023, fell to $537,000 in 2025 and have recovered to $575,000.

Data updated: September 2026 (Southwest Florida MLS, closed sales by calendar year, pulled 23 Sep 2026)

Four Calendar Years, Single-Family and Villa

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. Our search began on September 24, 2022, so 2022 is not shown as a full year. A second public record agrees on the 2024 peak: the Florida Department of Revenue’s qualified-sale file, served on the state’s statewide cadastral layer, also shows a 2024 single-family median of $1,000,000.

The Year-Over-Year Read

Closings rose 20 percent, from 40 to 48. The all-home median held at $807,500 in both years, built from different middle pairs. The single-family median rose 1.7 percent while its price per square foot slipped 2.8 percent, which means larger homes made up more of this year’s sales. The villa median rose 2.7 percent and villa days on market halved. These are small samples, and a handful of closings can move any of them.

What the Peak and the Reset Mean for a Seller Today

An owner who bought from DiVosta between 2015 and 2020 usually holds a substantial gain, because the builder’s own base prices started at $263,990 for the Serenity plan in December 2014 to the $400s to $700s for single-family homes in its December 2020 release, per DiVosta’s archived 2014 community page and Florida Weekly’s 2020 report. An owner who bought a resale in 2023 or 2024 faces a different conversation, about where today’s market sits against the purchase price. We would rather have that conversation with the recorded numbers on the table than with a portal estimate that ignores them.

Why Winding Cypress Turns Over at About Six Percent a Year

Forty-eight closings against 766 homes is about 6 percent of the community changing hands in a year [our arithmetic]. That is enough comparables to price from, but not enough to rescue a mispriced listing quickly, because the next sale of your own series on your own plat may be months away. A slow, steady market rewards the listing that is ready on day one, with its price, its district line and its flood file already answered.

How Does Winding Cypress Compare With Its East Naples Neighbours for a Seller?

Among five East Naples gated communities measured on one yardstick, Winding Cypress single-family homes sold at a median of $875,000, within 1 percent of Hacienda Lakes and about 36 percent below Naples Reserve, and kept the highest median share of list price, 96.26 percent. That position tells a seller which buyers will cross-shop the home and at what price.

Data updated: September 2026 (Southwest Florida MLS, single-family closings September 24, 2025 to September 23, 2026, pulled 23 Sep 2026)

One Yardstick, One Dataset

Method: the same Southwest Florida MLS search for every row, single-family homes only, each community by its own development name in the MLS dictionary, one median function for every figure. Fiddler’s Creek and Treviso Bay include golf-membership product; Winding Cypress and Hacienda Lakes have no golf course. Winding Cypress villas are left out because the comparison is single-family to single-family.

Hacienda Lakes Is the Price Twin

Hacienda Lakes closed 38 single-family homes at a median of $867,500, $7,500 below Winding Cypress, but its median home was larger, 2,475 square feet of living area against 2,158, so it traded at $364.61 per square foot against $405.92. When a buyer says Winding Cypress is expensive per foot, this is the comparison to answer: the buyer is paying for a newer single-builder DiVosta home, bundled amenities with no club to join, and a preserve setting beside a state forest, and a Winding Cypress listing has to show those things in the first photographs and the first lines of the remarks.

What Naples Reserve and the Golf Communities Tell a Seller

Naples Reserve, Fiddler’s Creek and Treviso Bay all traded higher per foot than Winding Cypress, from $470.78 to $736.68, and all three kept a smaller share of their list price. For a Winding Cypress seller they mark the ceiling a buyer is choosing not to pay. Our guides to Naples Reserve and Treviso Bay cover those communities in full. The practical point is simple: Winding Cypress sellers kept the most of their asking price of the five, 96.26 percent, while posting the longest median days on market, 76. Patient pricing close to the comparables is what worked here in the last twelve months.

Winding Cypress vs Verona Walk: Which Market Will Your Buyer Come From?

Winding Cypress and Verona Walk are next-door DiVosta communities on Collier Boulevard, and most buyers tour both. Winding Cypress has 766 homes built from 2015 to 2023 and a twelve-month median sale of $807,500; Verona Walk has 1,920 homes and a median of $494,000. Your listing must show a Verona Walk shopper what the difference buys.

Data updated: September 2026 (Southwest Florida MLS, Winding Cypress pulled 23 Sep 2026 and Verona Walk pulled 24 Sep 2026; Verona Walk CDD FY2026/27 adopted budget)

Why Your Buyer Tours Both

Verona Walk borders Winding Cypress to the north, the same builder built both, and the two communities share part of an entry road under a Cost Sharing Agreement recorded in 2014, under which the Verona Walk association pays 31 percent of the shared road, bridge, fountain, drainage and landscaping costs. A buyer who drives in to see your home has very likely seen a Verona Walk listing on the same trip. Our guide to Verona Walk, the larger DiVosta community next door, covers that community in the same depth.

The Decision Table

Sources: the Winding Cypress HOA’s 2026 Approved Budget, the Winding Cypress CDD’s FY2026/27 Final Budget, the Verona Walk CDD’s FY2026/27 adopted budget, and the Southwest Florida MLS, trailing twelve months for each community, windows ending a day apart. Winding Cypress splits attached and detached by the MLS building label; treat the two split rows as close cousins rather than identical cuts.

Who Should Choose Which

Choose Winding Cypress if you want newer DiVosta construction from 2015 to 2023, a detached home on a 50-foot or 65-foot homesite or a newer attached villa, an association whose full assessment is published before you offer, and a setting beside about 818 acres of recorded preserve, and you accept a higher district line into the 2040s. Choose Verona Walk if you want a lower price of entry, a larger community with twice the sales, an association-owned Town Center with no club initiation and a smaller district line, and you are comfortable seeing the association assessment first on the estoppel certificate.

What the Comparison Means for Pricing Your Winding Cypress Home

The median Winding Cypress sale ran $313,500 above the median Verona Walk sale, about 63 percent, but the gap per square foot of living area was about 29 percent, $394.83 against $306.19 [our arithmetic]. Much of the difference is home size and the detached mix rather than price per foot. Your listing has to earn the per-foot premium in the photographs and the remarks: construction year, the published fee stack, the preserve, the courts. And because the district line runs about $900 to $1,350 a year higher here, a seller who shows the buyer the exact line for the home’s plat early turns an objection into a known number. Jesse McGreevy at (239) 898-6072 will tell you which buyer pool your specific home will meet.

Selling in Winding Cypress While Buyers Compare Verona Walk? Get a Written Valuation First

A Winding Cypress home sold at a median of $807,500 over the last twelve months while the Verona Walk median was $494,000, so your list price has to explain the difference before a buyer asks. Request a written opinion of value through our Winding Cypress home valuation request, or call Jesse McGreevy direct at (239) 898-6072. Touring both communities as a buyer? Read how we represent buyers in Naples or call Marc Comisar at (239) 287-5873.

How Do We Price a Winding Cypress Home?

We price a Winding Cypress home from the recorded sales of its own series and plat, adjusted for plan, lot, preserve or lake frontage, condition, district assessment level and flood file, then test the number against the live listings and what a buyer’s appraiser will find. We never start from a community median or an automated estimate.

Data updated: September 2026 (Southwest Florida MLS pulled 23 Sep 2026; Winding Cypress CDD FY2026/27 budget; Collier County parcel layer)

We Start With Your Series, Not the Community Median

The MLS building field offers “Single Family” and “Villa Attached” for Winding Cypress and nothing else, so it cannot tell a Classic Series home on a 50-foot homesite from an Estate Series home on a 65-foot homesite, and every portal that reads the MLS shows one undifferentiated single-family market. The series has to be read from the homesite width, the floor plan and the recorded plat. 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, running from about 2,488 to 3,894 square feet under air. That is the first sort we do before any number is discussed.

The Plat Sets the District Assessment

Source: the Winding Cypress CDD’s FY2026/27 Final Budget. The Series 2015 bonds for Phases 1 and 2 mature in November 2045 and the Series 2019 bonds for Phase 3 in November 2049. Two otherwise similar homes, one on the Phase 3 plat and one on Phase 2, differ by roughly $475 to $485 a year in debt alone, and a careful buyer capitalizes that difference into the offer. About ten lots recorded on Phase 2 family plats carry Phase 3 debt, so we read your own tax bill rather than assume from the street.

Where the 48 Sales Happened, by Plat and Street

By street, 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 one each on Cocoplum Street, Clamshell Lane and Geranium Way, per the Southwest Florida MLS joined by address to Collier County’s parcel layer. Six streets had no MLS sale in the window: Lily Way, Wiregrass Court, Arrowhead Way, Chenille Court, Greenbriar Court and Bromeliad Drive. A street with no sale in one year is common with 766 homes on 15 residential streets, and it means your comparables will come from the same plat and series on a neighbouring street.

Why Automated Estimates Miss in Winding Cypress

Automated valuation models need dense, similar sales. Winding Cypress produces about four sales a month across three product lines, five plats with two district debt levels, roughly 70 lots that touch recorded preserve, and flood files that differ lot by lot where FEMA has issued individual letters. A model that blends a Jacaranda Lane villa with an Estate home on Winding Cypress Drive describes neither, and a model that reads the MLS cannot see the series at all. Buyers see those estimates too, which is one more reason your list price needs a written, sourced rationale behind it.

Preserve, Lake and the Value Drivers a Model Cannot See

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 the county’s parcel layer [our geometry]. Public data do not isolate a preserve or lake premium: 48 sales in a year is too small a sample to separate view from size, plan and condition, so we price it from the specific sales that had one. Upgrades matter too: impact glass where DiVosta made steel shutters standard, pool and cage additions, and interior finishes all move the number, and each is measurable from the recorded sales of the same series.

Pricing Against the Live Competition

With nine active listings and a 95.67 percent median sale to list ratio, your list price is judged against the homes a buyer can see the same day. We walk those listings, read their price histories and set your number where it wins the comparison rather than where it merely matches it. A price that looks sensible against the $1,250,000 median ask can still sit for a season when the closed single-family median is $875,000.

The Top of the Market, Read Carefully

The highest Winding Cypress sale of the last twelve months was $1,495,000 on Winding Cypress Drive in March 2026, a home of 3,656 square feet of living area. At about $409 per square foot of living area [our arithmetic], it sold within a few dollars of the single-family median per foot, $405.92. The lesson for a seller at the top of this market is that size carried the price, not a per-foot premium. The 48-month record is $1,895,000, set in January 2024, the year single-family prices peaked. An Estate home priced above the recent top needs a reason a buyer can see.

How Do We Market a Winding Cypress Home?

We market a Winding Cypress home to the buyer who is actually buying here: a full-time or seasonal Florida resident choosing a newer DiVosta home with bundled amenities and preserve views, often already renting nearby or comparing Verona Walk. That means architectural and aerial photography, video, a clear fee stack, database outreach and registered, well-run showings through the gate.

Data updated: September 2026 (HOA certified survey October 2025; HOA 2026 Approved Budget)

Who Actually Buys in Winding Cypress

The association’s own certified October 2025 survey, answered by 360 of 766 households, found 56.3 percent full-time and 43.7 percent part-time households, per the 2025 survey results. Your likely buyer is therefore one of two people: a Florida household moving within Collier or Lee County, or a seasonal buyer arriving for the January to April window who wants a lock-and-leave home with the clubhouse, courts and café already running. Winding Cypress is not age-restricted, and the listing should say so plainly.

Photography, Aerial and the Preserve Story

Winding Cypress sells from the air. About 818 of the roughly 1,176 acres on the five plats are recorded preserve tracts, the 29 stormwater lakes thread between the streets, and the Picayune Strand State Forest boundary sits about 140 meters from 7478 Winding Cypress Drive on the state’s conservation lands layer. Professional architectural photography, aerial and twilight capture, floor plans and a video walkthrough are standard on every McGreevy and Comisar listing, not an upgrade you pay for.

Where the Listing Gets Seen

The listing goes into the Southwest Florida MLS and out through its syndication, onto our own sites, and into targeted email and social campaigns to our database of Southwest Florida contacts. In a community with about four sales a month, the buyer is often already in a database, already renting in East Naples, or already touring the neighbouring communities on Collier Boulevard, so finding that person is a database problem before it is an advertising problem.

Showings Through the Gate

Visitors and agents follow the association’s Visitors and Agents process at the Collier Boulevard gatehouse, where attendants work alongside license-plate readers and a virtual callbox, and residents issue mobile guest passes through the SAGE app, per the association’s September 16, 2025 Board minutes. We register every showing ahead of time so no buyer is held at the gatehouse.

Signs, Open Houses and the Community Name

The recorded Declaration requires Board consent or permission in the Rules for any sign, and it names real estate signs specifically, so we clear signage and open-house plans against the current Rules and Regulations before the listing goes live. Section 16 of the Declaration also restricts using the Winding Cypress name or logo in promotional material except to identify where a property is. Your listing names the community as its location; it never uses the association’s logo or implies its endorsement.

Discreet and Off-Market Options

Not every Winding Cypress seller wants a Sunday open house. An estate, a divorce, a health change or a move north are often better handled quietly, through direct agent-to-agent outreach across the East Naples communities on Collier Boulevard and US 41. Less exposure can mean a lower price, and we will tell you plainly which way that trade lands for your home.

How Do We Negotiate a Winding Cypress Contract?

Jesse McGreevy and Marc Comisar negotiate every Winding Cypress offer themselves, and where the median home closed at 95.67 percent of list, that negotiation is where a seller’s money is kept or lost. We prepare answers on flood, insurance, the district line, the association fee and the timeline before the first offer arrives.

Data updated: September 2026 (Southwest Florida MLS, pulled 23 Sep 2026)

Partner-Level Negotiation, Never an Assistant

The person who priced your home is the person across the table from the buyer’s agent. Offers are not relayed by a coordinator, and counteroffers are not written from a template. That matters most in a market with nine active listings, where each serious buyer may be the only one for weeks.

Reading a 95.67 Percent Market Correctly

A median sale to list ratio of 95.67 percent does not mean every buyer expects about four percent off. It means many Winding Cypress homes were listed above what the market would pay: the 35 single-family homes that sold had a median list price of $925,000 against a median sale of $875,000. A home priced on the recorded evidence gives the buyer less room to argue, and we defend that price with the same evidence in the negotiation.

Flood, Insurance and Inspection Questions Answered Before the Offer

Winding Cypress homes were built from 2015 to 2023, so most insurers will not ask for a four-point inspection yet: Citizens Property Insurance requires one only on homes over 20 years old. The questions that do arise are the flood zone, the Elevation Certificate and the wind mitigation credits, and we put all three in the listing file on day one so the buyer’s insurance agent can quote the home in a day rather than a week.

Building the 20-Day Notice Into the Contract Dates

Because the Declaration requires notice to the association at least 20 days before closing, we write the contract dates around that notice and send it the week the contract is signed, together with the estoppel request. The buyer’s application runs through Tenant Evaluation under the association’s sale and lease application flyer. None of it is hard; all of it is a date, and a closing slips when nobody owns the date.

Which Recent Winding Cypress Sales Matter Most to Your Price?

The Winding Cypress sales that matter most are in your own product line and plat. Over the twelve months to September 23, 2026 the MLS recorded 35 single-family closings at a median of $875,000, from $575,000 to $1,495,000, and 13 villa closings at a median of $575,000, from $455,000 to $635,000.

Data updated: September 2026 (Southwest Florida MLS, pulled 23 Sep 2026)

By Product, From the MLS

The MLS carries no field that separates the Classic Series from the Estate Series, so the 35 single-family sales are one line here, and the split is exactly the work a pricing analysis has to do by hand.

The Top of the Single-Family Market

The three highest single-family sales of the year were $1,495,000 on Winding Cypress Drive in March 2026, $1,475,000 on Cocoplum Street in May 2026 and $1,260,000 on Winding Cypress Drive in November 2025. Cocoplum Street sits on the Phase 3 plat, which carries the higher district debt line, and still produced the second-highest sale of the year, which tells a seller on Phase 3 that the district line is a negotiating point rather than a ceiling.

The Villa Floor on Jacaranda Lane

The three lowest sales of the year were all villas on Jacaranda Lane: $455,000 in November 2025, $460,000 in March 2026 and $470,000 in June 2026. The villa median of $575,000 sits more than $100,000 above that floor, so condition, updates and position within the pair explain most of the villa range. A villa seller should price against the villas that sold near the median, and should show a buyer exactly what separates the home from the three at the bottom.

What a Buyer’s Appraiser Will Use

When your buyer is financing, the lender’s appraiser will look first for closed sales of the same product within the last six to twelve months, and in Winding Cypress that usually means a handful of sales of the same series. We assemble that comparable set before you list, including the older or farther sales an appraiser may be forced to use when your plan has not sold recently, so the price we recommend is one the appraisal can support.

What Does It Cost to Sell a Home in Winding Cypress?

Selling a Winding Cypress home costs the negotiated brokerage commission, Florida documentary stamp tax on the deed at $0.70 per $100, the association’s estoppel certificate fee, a municipal lien search and prorated property taxes. In Collier County the buyer customarily pays the owner’s title policy, and the buyer, not the seller, pays the $1,050 resale capital contribution.

Data updated: September 2026 (Florida Statutes 201.02 and 720.30851, DBPR estoppel fee schedule, HOA 2025 audit)

Documentary Stamp Tax on the Deed

Florida charges $0.70 per $100 of consideration, or portion thereof, under Florida Statutes 201.02, and a Florida seller customarily pays it on a residential resale. At the Winding Cypress single-family median of $875,000 that is $6,125. At the villa median of $575,000 it is $4,025, and at the year’s top sale of $1,495,000 it is $10,465. It is the largest fixed cost of selling after commission and appears on your closing statement as one line.

Title Insurance and the Collier County Custom

In most Florida counties, including Lee County, the seller customarily chooses the closing agent and pays the owner’s title policy. In Collier County the custom flips and the buyer customarily chooses and pays. Nothing in the statutes fixes the allocation, so the contract controls, and a seller moving within Southwest Florida should confirm it in writing rather than assume the Lee County habit. Florida sets the title premium itself under Florida Administrative Code Rule 69O-186.003, so the rate is the same whichever title company is used.

The Estoppel Certificate

Every Winding Cypress sale needs one estoppel certificate, from the Winding Cypress Homeowners Association; there are no villa or neighbourhood sub-associations. The Declaration requires it within 10 business days of a request, matching Florida Statutes 720.30851, and the current DBPR fee schedule caps the fee at $299, plus $119 for expedited delivery and up to $179 more if the account is delinquent. The association does not publish its actual fee in advance; it prints on the certificate. In Collier County practice the seller customarily pays it.

The Fees Your Buyer Pays, Not You

The recorded Declaration places the resale capital contribution on the purchaser, and the association’s 2025 audit records it at $1,050 per resale. The Declaration also allows a fee for processing sale and lease applications, run through Tenant Evaluation; the amount is not published. The buyer also takes over the district assessment on the next tax bill. Knowing which side of the ledger each item belongs on is the difference between a clean closing statement and a last-week argument.

Commission After the NAR Settlement

Since August 17, 2024, offers of buyer broker compensation cannot be advertised in the MLS, buyers sign written agreements with their own agents, and every commission is fully negotiable and not set by law, per the National Association of REALTORS settlement guidance. What you negotiate with us is the listing side, and whether to offer anything toward the buyer’s agent is a separate decision we make together, off the MLS, based on the buyers your home is likely to meet.

A Seller Net Sheet at the Winding Cypress Single-Family Median

The proration line is 181 days of the $7,724.86 combined 2025 tax bill of a homesteaded Phase 2 home, which already includes that home’s district assessment and solid-waste charge, per the Collier County Tax Collector [our arithmetic]. Florida property taxes are paid in arrears, which is why the seller credits the buyer. Your own net sheet uses your contract price, your bill and your closing date, and we build it with you before you sign a listing agreement.

What Must a Winding Cypress Seller Disclose Under Florida Law?

A Winding Cypress seller owes the buyer the Florida Statutes 720.401 homeowners association disclosure summary before the contract is signed, not at closing, plus the community development district disclosure, the flood disclosure created in 2024 and the property tax disclosure summary. Every Florida seller must also disclose known material facts that are not readily observable.

Data updated: September 2026 (Florida Statutes 720.401, 190.048, 689.302 and 689.261, retrieved 24 Sep 2026)

The HOA Disclosure Summary Is Owed Before Contract

Florida Statutes 720.401 says a prospective parcel owner “must be presented a disclosure summary before executing the contract for sale,” and on a resale the parcel owner supplies it. The contract must carry the statutory voidability warning. If the summary is missing, the buyer may cancel within three days after receiving it or before closing, whichever comes first, and that right cannot be waived. Winding Cypress has one homeowners association and no condominiums, so every Winding Cypress seller falls under this Chapter 720 duty. Confirm the form with your closing agent or attorney; this is information, not legal advice.

The Community Development District Disclosure

Florida Statutes 190.048 requires a disclosure to buyers of property inside a community development district, and the Winding Cypress CDD, created by Collier County Ordinance 2015-48, covers the developed footprint of about 358 acres. The recorded Series 2015 and Series 2019 assessment notices make the debt a lien on each lot until paid. We attach the district’s budget table for your product and plat so the buyer sees the exact figure rather than a range.

The Flood Disclosure

Florida’s residential flood disclosure, 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. Answer it from your own records, completely. Because Winding Cypress is mapped Zone AE, the Elevation Certificate and any FEMA letter for your lot belong beside the form.

The Property Tax Disclosure Summary

Florida Statutes 689.261 requires that a buyer of residential property receive a property tax disclosure summary at or before contract, warning that the buyer should not rely on the seller’s current taxes. In Winding Cypress, where a homesteaded seller may carry years of Save Our Homes cap, that warning describes a real change in the buyer’s carrying cost, which we explain in the ownership-cost section below.

What the Winding Cypress Declaration Assigns to Each Side

The recorded Declaration splits the transaction cleanly. The seller notifies the association in writing at least 20 days before closing. The buyer completes the association’s application through Tenant Evaluation and pays the resale capital contribution. The association issues the estoppel certificate within 10 business days of a request and records a Certificate of Approval, which it cannot withhold for a sale. Who owes what and when is fixed by the covenant; the current dollar amounts print on the estoppel.

Known Defects and Johnson v. Davis

Under Johnson v. Davis, a Florida seller who knows of facts materially affecting value that are not readily observable must disclose them. For a Winding Cypress home that means prior water intrusion, insurance claims, roof and plumbing history, open permits and any shared-roof or party-wall history on a villa. Disclosing early costs a negotiation; concealing costs the deal.

How Does the Flood Map Affect Selling a Winding Cypress Home?

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, so most buyers with a mortgage will need flood insurance. About 15 homes have their own FEMA letters placing them in shaded Zone X. A seller’s Elevation Certificate and any such letter shape the buyer’s quote.

Data updated: September 2026 (FEMA National Flood Hazard Layer and LOMR-F points, Collier County Elevation Certificates layer, retrieved 23 Sep 2026)

Street by Street

Sources: FEMA’s National Flood Hazard Layer and BFE lines, one sampled address per street, and the National Hurricane Center’s storm surge risk maps, which show a worst-case scenario rather than a forecast. Chenille Court and Wiregrass Court were not sampled, so the table assigns them no zone. Your own address governs; check it on the FEMA Map Service Center.

The Builder-Era Letters No Longer Answer the Question

From 2015 to 2019 the developer obtained phase-wide FEMA letters that moved whole phases out of the high-risk zone. On the 2024 map those letters are superseded or not incorporated, per FEMA’s LOMR-F layer. A seller who finds one of those older letters in the original closing file should not present it as the home’s current flood status. What does answer the question is a single-lot letter issued since 2024, and 16 of those cases, covering about 15 homes, mostly on Live Oak Drive and Cocoplum Street, have moved individual lots or structures to shaded Zone X. A lender keeps the option to require flood insurance even then, but the letter usually changes the quote.

Elevation Certificates and Surveyed Floors

Collier County holds 230 Elevation Certificates on Winding Cypress streets, filed with permits from 2014 to 2019, and releases them free, per its Elevation Certificates layer and 2026 flood protection newsletter; the county’s floodplain line is (239) 252-2942. Surveyed floors on the two certificates read in full sit at 10.10 feet NAVD88 on Live Oak Drive, certified in 2015, and 9.40 feet on Cocoplum Street, certified in 2019, about 2.1 and 1.4 feet above the 8.0-foot base flood elevation. Put your certificate in the listing file before the first showing.

A Letter of Map Revision for a Single Lot

If your certificate shows the lot and structure above the base flood elevation, a single-lot request to FEMA may be worth filing before you list. FEMA’s online Letter of Map Change portal and the MT-1 application forms set out the process. Fifteen neighbours have already done it since 2024. Whether your lot qualifies is a survey question, and the certificate is where the answer starts.

Evacuation Zone D and the Storm Record

Every sampled Winding Cypress address sits in Collier County Evacuation Zone D on the county’s evacuation layer, landward of US 41, and Zone D was not ordered out for Hurricane Ian or Hurricane Milton. After Ian, the district’s November 2022 minutes, in its February 2023 board book, record that “No significant damage was noted by the community.” FEMA’s claims data show three flood insurance claims in the wider Census block group, all from Irma in 2017, none paid, and none for Ian, Helene or Milton.

Insurance Credits a Buyer Will Ask About

Unincorporated Collier County is Class 5 in FEMA’s Community Rating System, worth a 25 percent discount on eligible flood policies inside the Special Flood Hazard Area and 10 percent outside it. Flood policies on newer single-family homes in this Census block group had a median cost of about $1,270 in 2026 terms, per FEMA’s anonymized policy data, which covers more than Winding Cypress alone. DiVosta built with steel-reinforced concrete block, engineered roof trusses with hurricane tie-downs and galvanized steel shutters as standard, per its brochure, and those features score on a wind mitigation report, valid for up to five years, with a new state form in effect since April 1, 2026.

What Will Your Buyer Pay to Own a Winding Cypress Home?

A Winding Cypress buyer pays the association assessment for the series, the district assessment for the product and plat, the county solid-waste charge and property tax reset to market value. Before tax and insurance, those three lines run from about $8,154 a year for a villa to about $9,668 for a Phase 3 Estate home.

Data updated: September 2026 (HOA 2026 Approved Budget; Winding Cypress CDD FY2026/27 budget; Collier County Tax Collector 2025 bills)

The Association Assessment by Series

Source: the association’s 2026 Approved Budget, with home counts from the district’s unit census. The assessment covers lawn and irrigation maintenance by lot frontage, common areas, operations and staff, the clubhouse and amenities, the Shady Palm Café fund of $223.89 and reserves of $606.32 per home. The 2026 assessment is about 1 percent lower than 2025, which is a line worth putting in the listing.

The District Assessment and When It Ends

The district assessment appears on the county tax bill each November, from $1,643.98 for a villa to $2,338.98 for a 65-foot homesite on the Phase 3 plat, before the 4 percent November discount, as the pricing table above sets out. The debt part ends when the bonds retire, November 2045 for Series 2015 and November 2049 for Series 2019; the $794.98 operations and maintenance part continues. The district budget also tracks owners who have prepaid their bond assessment, so the debt part can be paid off; the operations part cannot.

Why the District Line Rose Once

The district’s operations and maintenance line rose from $232.06 in the FY2022/23 budget to about $795 in FY2023/24 and has held at $794.98 since. The driver is lake-bank remediation after LJA Engineering’s 2024 lake assessment of the community’s 29 lakes; the FY2026/27 budget carries $300,000 for remediation and a lake-bank reserve of $366,062 as of July 1, 2026. Buyers will see the jump in any history they pull, and three flat years since is the answer.

The Property Tax Your Buyer Inherits

The 2025 Winding Cypress tax rate was 10.5058 mills in Collier millage code 21, with the same rate across the community’s two millage codes, plus the district line and a $261.91 solid-waste charge. Save Our Homes caps follow the owner, not the house, so the home is reassessed after the sale. Applied at 10.5058 mills to the $875,000 single-family median, the ad valorem illustration is about $9,193 a year before any exemption [our arithmetic], against $7,724.86 in total paid in 2025 on one homesteaded Phase 2 home including its district and solid-waste lines. That illustrates the mechanism, not a quote for any home.

The Worked Carrying Cost

Our sums of the published lines. The solid-waste charge is from the Collier County Tax Collector 2025 bill. A listing that shows the buyer the right row for the home answers the first question every Verona Walk comparison raises.

What the Assessment Does Not Include

No bulk cable or internet package appears in the association’s 2026 budget, so owners contract service individually. There is no golf course and no marina, and we describe the community as gated, with gatehouse attendants, which is exactly what the recorded documents support. The lakes are district stormwater lakes, and the Rules allow no fishing, boating or swimming. No association special assessment was found in recorded documents or the association’s public pages through September 2026.

What Is Different About Selling a Winding Cypress Villa?

Winding Cypress villas are 152 fee-simple, paired homes on Jacaranda Lane and the 7093 to 7202 block of Live Oak Drive, with no condominium regime. Villa owners maintain and insure their own villa under party-wall and shared-roof rules, pay the lowest association and district amounts, and sold fastest this year, at a 50-day median.

Data updated: September 2026 (Southwest Florida MLS pulled 23 Sep 2026; recorded Declaration; HOA 2026 budget)

Maintenance and Insurance Sit With the Villa Owner

The recorded Declaration makes each villa owner responsible for maintaining the villa and carrying replacement-value insurance on it, with party-wall, shared-roof and party-fence provisions governing the attached neighbour. A villa buyer will ask for your current policy, your roof record and any shared-roof or party-wall history, and a seller who has that folder ready removes a week of back-and-forth after the offer.

Villa Results and Live Competition

The 13 villas that closed in the twelve months to September 23, 2026 sold at a median of $575,000, $370.01 per square foot of living area, on a median living area of 1,554 square feet, with a median 94.76 percent of list price and a median of 50 days on market, per the Southwest Florida MLS. Two villas were active on September 23, 2026, at $575,000 and $599,900, and villa supply was 1.8 months, the tightest in the community. A villa priced near the median meets a buyer who has very few alternatives inside the gates.

The Live Oak Drive Coding Caution

The MLS building label is chosen by the listing agent, and county records place at least two Live Oak Drive homes that sold this year under the single-family label on the villa block 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. For a villa seller on Live Oak Drive, it means the right comparables may be hiding under the wrong label, and we find them by address.

Which Winding Cypress Rules Affect a Sale?

Five recorded Winding Cypress rules shape who will buy and how they will use the home: leases of 30 days to one year with Board approval and no more than three a year, a limit of three household pets, vehicles such as boats and golf carts kept in the garage, tight fence and pool rules, and hurricane shutter timing.

Data updated: September 2026 (Amended and Restated Declaration recorded 2024; Rules and Regulations; 2025 shutter amendment)

Leasing Rules

Leases must run at least 30 continuous days and no more than one year, with no more than three leases per calendar year, 30 days between lease starts, the whole home only and Board approval, under the recorded Declaration. Rentals under 30 days are treated as a prohibited business use. An investor buyer needs to hear that on the first call, and seasonal leasing fits comfortably inside it.

Pets

The Declaration allows up to three household pets, excludes certain breeds and aggressive dogs, and keeps pets leashed and out of the amenity center and café. A buyer with a large household of animals should hear the limit before writing an offer, not during the application.

Vehicles, Boats and Golf Carts

Boats, trailers, recreational vehicles, commercial vehicles, motorcycles and golf carts must be kept in the garage, and there is no overnight street parking. Golf carts must be registered, insured and driven by a licensed driver, and may not leave the community. For a Naples buyer with a boat, that decides the purchase, so we qualify buyers on it early rather than lose a contract over it.

Fences, Pools and Exterior Changes

Fences are tightly restricted and require architectural review approval; the current Rules allow only equipment screening. In-ground pools go through architectural review, which carries a 60-day response period and a refundable deposit of up to $5,000, and above-ground pools are prohibited. A buyer who plans a pool or a cage extension should know the process on day one.

Hurricane Shutters

Under the 2025 amendment recorded at Official Records Book 6507, Page 955, temporary shutters may go up no more than 72 hours before a storm and must come down within 72 hours after, and absent owners with permanently affixed shutters may keep them closed from June 1 to November 30. That is a useful answer for the seasonal buyer who asks how the home is closed for summer.

How Long Does It Take to Sell a Winding Cypress Home?

A well-priced Winding Cypress home took a median of 73 days on market over the last twelve months, 76 for single-family homes and 50 for villas, plus a contract period that includes the association’s 20-day notice, the estoppel and the buyer’s financing. Listing ahead of season, with the flood and district file prepared, shortens both halves.

Data updated: September 2026 (Southwest Florida MLS, pulled 23 Sep 2026)

Season and the East Naples Buyer

Naples buyer traffic concentrates from January through April, when seasonal buyers are in town touring communities, so the best time to be ready is the autumn before. With 43.7 percent of households part-time in the association’s own survey, the seasonal buyer is a large share of your market, but the 56.3 percent full-time share means a real summer buyer exists too, fewer but more serious, meeting thinner competing inventory. We look at what else will be listed in your product line and price band before recommending a date.

A Realistic Sequence

In the four weeks before listing: valuation, your Elevation Certificate and any FEMA letter, a wind mitigation report, photography and a draft disclosure package with the district budget line for your plat. At contract: notify the association in writing, order the estoppel and send the buyer the application route. During the contract period: inspections, appraisal, insurance binding and title work. Before closing: the association records its Certificate of Approval and the estoppel figures go onto the closing statement.

Selling While You Are Up North

With 43.7 percent of Winding Cypress households part-time, many sellers are not in Florida when the right buyer appears. Marc Comisar manages showings, contractors, inspections and walkthroughs on site, and Florida closings routinely use remote signing and mail-away packages, so an owner can sell without flying down. Canadian and other foreign sellers should bring in a CPA early for FIRPTA withholding.

What Should Your Listing Say About Life Around Winding Cypress?

A Winding Cypress listing should sell the life as well as the house: a clubhouse bundled into the assessment, 4 clay tennis, 8 pickleball and 4 bocce courts, the Shady Palm Café, a boardwalk to a preserve overlook, a hospital about 3 minutes from the gate, and A-rated zoned elementary and middle schools.

Data updated: September 2026 (HOA 2026 Rules final draft; OpenStreetMap routing from the Collier Boulevard gate, without traffic; FLDOE 2026 school grades)

The Club, Courts and Café

The clubhouse, marketed by DiVosta as a 17,500-square-foot clubhouse and described by its builder, DeAngelis Diamond, as a 22,000-square-foot amenity center, is owned by the association and paid for inside the assessment, with no equity club and no non-resident members. The association’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 clay tennis court in 2026. The Shady Palm Café is the association’s poolside bar and restaurant, run with its own manager and chef.

Preserve, Boardwalk and Picayune Strand

A wooden boardwalk leads to a sheltered overlook that closes at sunset; entry into the preserve itself is not allowed. Beyond the preserve tracts lies the 74,138-acre Picayune Strand State Forest, managed by the Florida Forest Service, which also runs prescribed burns there. Buyers who love the setting will ask about both the wildlife and the smoke, and an honest listing answers both.

Beaches, Shopping and the Hospital

From the Collier Boulevard gate, without traffic, Publix at Freedom Square is 1.7 miles and about 4 minutes away, Physicians Regional Medical Center on Collier Boulevard 2.2 miles and about 3 minutes, Naples Pier 11.1 miles and about 21 minutes, and Tigertail Beach on Marco Island 11.4 miles and about 23 minutes, per OpenStreetMap routing. Collier County property taxpayers qualify for a free beach parking permit, per Collier County Parks. January to April adds time on Collier Boulevard and US 41.

Schools Zoned to Winding Cypress

For the 2026-27 school year the district’s address lookup returns Lely Elementary, Manatee Middle and Lely High for Winding Cypress addresses, and the Florida Department of Education’s 2026 grades are A, A and B. Buyers with children should confirm their specific address with Collier County Public Schools, and a listing can state the zoned schools with that caveat.

What Is Changing Nearby

A second Collier County Costco, about 162,700 square feet, is being built about 3 miles north at Collier Boulevard and Rattlesnake Hammock Road, targeting fall 2026 per WGCU; the opening is not yet confirmed. The Collier MPO 2050 plan funds widening Collier Boulevard to six lanes south of Manatee Road in the 2031 to 2035 period. New construction nearby, including Mattamy’s 249-home-site Summerlit about 0.7 miles from the district’s edge, competes on warranty; a Winding Cypress resale competes on a finished amenity center and mature landscaping.

How Do You Get a Free Winding Cypress Home Valuation?

You get a free Winding Cypress home valuation by requesting one online or calling Jesse McGreevy at (239) 898-6072. It is a written opinion of value built from recorded sales of your own series and plat, with your buyer’s district line, association assessment and flood file beside it. There is no cost and no obligation to list.

What a McGreevy and Comisar Valuation Includes

You receive the MLS and county-recorded sales for your series and plat with their dates and sources, a price per square foot analysis on the MLS living-area basis, the live competition with price histories, the association and district amounts your buyer will underwrite, your flood zone and any Elevation Certificate or FEMA letter on file, and a recommended list price with a defensible range. Request it through our Winding Cypress home valuation request or the McGreevy and Comisar valuation form.

How to Reach Us Today

Call Jesse McGreevy direct at (239) 898-6072 or email [email protected]. Call Marc Comisar at (239) 287-5873. The office of McGreevy and Comisar is at 24031 S Tamiami Trl #101, Bonita Springs, FL 34134. Bring your address, your timeline and the one thing you are most worried about, and you will get a straight answer.

Why the Valuation Comes Before the Listing Agreement

In a market with nine active listings, a 95.67 percent median sale to list ratio and asking prices well above closed sales, the price decides the sale. We would rather you see the evidence and the number before you commit to anything, and many owners use the valuation to decide whether to sell this season or next. Few homes here come up for sale at once, so the next owner who sells should call us first.

What Do Sellers Say About Working With McGreevy and Comisar?

McGreevy and Comisar are a top-reviewed listing team on Google, and the quotes below are genuine five-star client reviews from that profile, 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 reviews profile, and judge Winding Cypress service by it.

A Seller on Follow Through

★★★★★ “Jesse was very professional, helpful and kept in touch with ideas and suggestions which developed into a sale. Highly recommend his company for their excellent follow through.” Verified Google review

Follow through is what carries a Winding Cypress contract through the association’s 20-day notice, the estoppel and a buyer’s flood insurance quote.

A Client Who Sold and Bought in One Move

★★★★★ “Marc was extremely helpful in the sale of our old home and getting our new home to the condition that we wanted it to make it ours. He has been available to us for every step of our journey, even after the transaction closed.” Verified Google review

A Winding Cypress seller moving within Southwest Florida has two transactions to run as one plan.

A Client on Market Knowledge

★★★★★ “Their knowledge of the Southwest Florida market really stood out, and you can tell they genuinely care about their clients and getting the best results possible. They were always available to answer questions, kept us informed every step of the way, and paid attention to every detail.” Verified Google review

A Client on the Process

★★★★★ “I had a great experience working with Marc Comisar and Jesse McGreevy. They were professional, knowledgeable, and made the entire process feel smooth from beginning to end.” Verified Google review

A Client on Buying or Selling

★★★★★ “Jesse and Marc are extremely knowledgeable about Southwest Florida real estate! If you are looking to buy or sell property, look no further than Domain Realty and their amazing team!” Verified Google review

Why Does a Winding Cypress Specialist Matter When You Sell?

A Winding Cypress specialist matters because the facts that decide a sale here live in recorded documents rather than in a listing feed: three product lines the MLS cannot separate, a district assessment set by the plat, a 20-day association notice, a buyer-paid capital contribution, and a Zone AE flood map with lot-by-lot FEMA letters.

Jesse McGreevy

Jesse McGreevy is a licensed Florida REALTOR and Sales Associate with Domain Realty, a co-founder of the brokerage, and one half of McGreevy and Comisar, Top 1% Real Estate Agents Nationally Since 2008. He started in Southwest Florida real estate in October 2004 and launched his own team in October 2008. He runs pricing, marketing, data and the association, district and flood paperwork. Reach him at (239) 898-6072, and read his profile on the Jesse McGreevy agent page.

Marc Comisar

Marc Comisar is a licensed Florida REALTOR and Broker Associate with Domain Realty and the other half of McGreevy and Comisar. He runs the field side: showings, gate registration, buyer agent conversations, inspections and the on-site management that lets a part-time Winding Cypress owner sell without flying down. Reach him at (239) 287-5873, and read his profile on the Marc Comisar agent page.

What a General Naples Agent Tends to Miss Here

A general agent may price an Estate home off the community’s single-family median, treat a Phase 3 home as if it carried the Phase 2 district line, present a superseded builder-era flood letter as current, put the resale capital contribution on the seller’s side of the statement, or send the association its notice in week three of the contract. None of those errors is exotic, and each one costs a seller time or money.

How Winding Cypress Compares With Other Naples Seller Markets

Every Naples community sells differently. Audubon Country Club in North Naples requires every buyer to join its club and trades about twenty homes a year behind two gates, as we explain in our guide to selling a home in Audubon Country Club. Winding Cypress sits at the other end of that spectrum: amenities bundled into one association, no club application, and an association that cannot block a sale.

Are You Also Buying Your Next Home in Southwest Florida?

When a Winding Cypress seller is moving within Collier or Lee County rather than leaving Florida, the sale and the next purchase are one financial plan. We run both sides together, including the timing of two closings and the Save Our Homes portability claim that can carry accumulated tax savings to your next Florida homestead.

Buying and Selling in the Same Season

A Florida homesteader who sells and establishes a new Florida homestead may transfer accumulated Save Our Homes benefit, within statutory limits, by filing with the new homestead application, per the Florida Department of Revenue. The January 1 test matters, because homestead status is fixed on that date each year. We sequence both closings around that calendar. If you are buying, start with how we represent buyers in Naples or call Marc Comisar at (239) 287-5873.

Buying Inside Winding Cypress Again

Some owners move within the gates, from an Estate home to a villa on Jacaranda Lane, or from Phase One up to a newer Phase 3 home. If your next home is here, see how we help buyers purchase in Winding Cypress, and read the full Winding Cypress community guide for the governance, club, flood and school detail this page summarizes.

Frequently Asked Questions, Seller Edition: Selling a Home in Winding Cypress

These are the questions Winding Cypress owners in East Naples actually ask before they sell, answered for a Collier County seller, each in a single paragraph. They cover price, timing, the association and district steps, costs, disclosure, flood and taxes. Nothing here is tax or legal advice; confirm anything that affects your sale with your closing agent, attorney or CPA.

Data updated: September 2026 (Southwest Florida MLS pulled 23 Sep 2026; association and district documents as linked above)

How do I sell my home in Winding Cypress in Naples?

Start with a written valuation built from the recorded sales of your own series and plat, not a portal estimate, then prepare the file before you list: your Elevation Certificate and any FEMA letter, a wind mitigation report, the district budget line for your plat and the association’s 2026 assessment for your series. Market the home to the buyer who is also touring Verona Walk and Hacienda Lakes, price it where it wins against the nine or so live listings, and send the association its 20-day notice the week you sign a contract. Call Jesse McGreevy at (239) 898-6072 to begin.

Who is the best listing agent for Winding Cypress?

Look for an agent who prices from recorded evidence, reads the series and plat the MLS cannot show, and personally negotiates the offer. McGreevy and Comisar are Top 1% Real Estate Agents Nationally Since 2008 and the #1 Team in Southwest Florida since 2012, and Jesse and Marc handle every listing themselves. Test any agent you interview on three things: their comparable set for your series, their read of your district line and flood file, and their plan for a market where asking prices sit far above closed sales.

What is my Winding Cypress home worth?

It depends first on the product. Over the twelve 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 the Southwest Florida MLS. Within single-family, the Estate or Classic Series, the plan, the lot, the plat’s district line, the roof and the flood file all move the number. Request a written valuation for your specific home.

What is the price per square foot in Winding Cypress?

Over the twelve months to September 23, 2026, single-family homes sold at a median of $405.92 per square foot of living area and villas at $370.01, per the Southwest Florida MLS; 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, so compare your home only with figures on the same living-area basis.

How many Winding Cypress homes sell in a year?

Forty-eight Winding Cypress homes closed in the twelve months to September 23, 2026, for a total of $38,718,900, per the Southwest Florida MLS: 35 single-family homes and 13 villas. That is about 6 percent of the community’s 766 homes in a year, up from 40 closings in the prior twelve months. A steady flow of comparables exists, but not so many that a mispriced listing is rescued quickly.

How long do Winding Cypress homes take to sell?

The median Winding Cypress closing in the twelve months to September 23, 2026 spent 73 days on market, across the 46 sales with a recorded figure; single-family homes took a median of 76 days and villas 50. Add a contract period that includes the association’s 20-day notice, the estoppel and the buyer’s financing. Pricing to the closed comparables from the first day is what shortens the clock.

What is the sale to list ratio in Winding Cypress?

The median Winding Cypress closing in the twelve months to September 23, 2026 sold at 95.67 percent of its final list price across all 48 sales: 96.26 percent for single-family homes and 94.76 percent for villas. Seven of the 48 sold at or above list. Among five East Naples communities measured the same way, Winding Cypress single-family sellers kept the highest share of their list price.

Is it a seller’s market or a buyer’s market in Winding Cypress?

Both signals are present. With nine active listings against 48 closings a year, Winding Cypress carried about 2.2 months of supply on September 23, 2026, which favours sellers. With a 95.67 percent median sale to list ratio, individual negotiations still give buyers room. A well-priced home sells into scarce supply; an overpriced one meets a buyer who waits it out.

Are prices dropping in Winding Cypress?

Not on the latest twelve months. The single-family median rose 1.7 percent year over year, from $860,000 to $875,000, and the villa median rose 2.7 percent, from $560,000 to $575,000, per the Southwest Florida MLS. Single-family price per square foot slipped 2.8 percent because larger homes sold. On calendar years, single-family prices peaked at $1,000,000 in 2024 and reset to $860,000 in 2025 before recovering in 2026.

Why are asking prices so much higher than recent sales?

On September 23, 2026 the seven active single-family listings asked a median of $1,250,000 against a twelve-month single-family median sale of $875,000. Part of the gap is mix, because larger Estate homes are over-represented among today’s listings, and part is sellers pricing against each other’s asks rather than against closed sales. Homes that close are priced against the closed comparables.

Why is the online estimate for my Winding Cypress home wrong?

Automated models read the MLS, and the MLS cannot tell a Classic Series home from an Estate Series home, cannot see which plat’s district line a home carries and cannot see whether a lot has its own FEMA letter. They also blend villas and single-family homes where the product label is miscoded. Buyers see those estimates too, which is why your list price needs a sourced rationale.

When is the best time of year to list a Winding Cypress home?

Naples buyer traffic peaks from January through April, so being fully prepared and on the market before that window is usually best. With 43.7 percent of households part-time in the association’s own survey, the seasonal buyer is a large share of the market, and the full-time majority supports a smaller, serious summer market with less competing inventory. We check what else is likely to list in your price band before recommending a date.

Does the Winding Cypress association have to approve my buyer?

The association must be told, but it cannot say no. Under the recorded Declaration, the owner notifies the association at least 20 days before closing, the association cannot disapprove a sale, and it records a Certificate of Approval in the county’s official records. The buyer completes the association’s application through Tenant Evaluation. Leases are different: every lease needs Board approval.

Who pays the resale capital contribution when I sell?

The buyer. The recorded Declaration assigns the resale capital contribution to the purchaser and lets the Board set the amount each year. The association’s 2025 audit records $1,050 per resale in 2025, collected on 45 resales that year. Confirm the current amount on the estoppel so it lands on the buyer’s side of the closing statement.

Is there a transfer fee in Winding Cypress?

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

How many estoppel certificates does a Winding Cypress sale need?

One. Winding Cypress has a single homeowners association and no villa or neighbourhood sub-associations, so every sale needs one estoppel certificate from the Winding Cypress Homeowners Association. The Declaration requires it within 10 business days of a request, matching Florida Statutes 720.30851. The district assessment is not an estoppel item; it appears on the county tax bill.

What does an estoppel certificate cost in Florida?

The current DBPR schedule caps a homeowners association estoppel at $299 for a current account, with an additional $119 for expedited delivery and up to $179 more if the account is delinquent. The certificate states what the home owes the association through the closing date. In Collier County practice the seller customarily pays the estoppel fee.

What does it cost to sell a house in Winding Cypress?

Expect the negotiated commission, documentary stamp tax on the deed at $0.70 per $100, the estoppel fee, a municipal lien search, prorated taxes, and any negotiated repairs or credits. At the $875,000 single-family median the deed stamps alone are $6,125; at the $575,000 villa median they are $4,025. In Collier County the buyer customarily pays the owner’s title policy, and the buyer pays the resale capital contribution.

Who pays for title insurance in Collier County?

By Collier County custom the buyer usually chooses the closing agent and pays the owner’s title policy, which is the reverse of the Lee County custom. Nothing in the statutes fixes the allocation, so the contract controls. Florida sets the title premium itself, so the rate is the same whichever title company is used.

Is real estate commission negotiable in Naples?

Yes. Commission is not set by law and is fully negotiable. Since August 17, 2024, offers of buyer broker compensation cannot be advertised in the MLS, and buyers sign written agreements with their own agents. What matters in Winding Cypress is less the rate than whether the team can find the buyer, answer the flood and district questions and defend the price.

Does my buyer take over the Winding Cypress CDD assessment?

Yes. The district 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 for a villa to $2,338.98 for a 65-foot homesite on the Phase 3 plat, before the 4 percent November discount. Nothing is paid off at closing unless a party chooses to prepay the bond portion.

Does the district increase hurt my Winding Cypress sale?

Buyers will notice it, so answer it up front. The district’s operations and maintenance line rose from $232.06 in FY2022/23 to about $795 in FY2023/24 and has held at $794.98 since, driven by lake-bank remediation across the community’s 29 lakes. Showing buyers the budget and the flat three-year trend early turns the question into a known number.

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 association’s public pages and posted Board minutes found no association special assessment through September 2026, and the 2026 assessment is about 1 percent lower than 2025. 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 association reserves?

The association’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. Recent reserve projects include resurfacing three clay tennis courts and replacing the pool heaters in 2025. All of these documents are posted publicly on the association’s website, and a buyer’s agent will read them.

Is my Winding Cypress home in a flood zone?

Yes, on the current map. FEMA’s map effective February 8, 2024 places Winding Cypress in Zone AE with a base flood elevation of 8.0 feet NAVD88, unless your lot has its own FEMA letter moving it to shaded Zone X. Since 2024, 16 single-lot cases covering about 15 homes have done that, mostly on Live Oak Drive and Cocoplum Street. Check your own address on the FEMA Map Service Center.

Does my old builder flood letter still count?

No. The developer’s phase-wide FEMA letters from 2015 to 2019 are superseded or not incorporated on the 2024 map, per FEMA’s LOMR-F layer, so an older letter in your closing file no longer answers the flood question. Only a letter issued for your specific lot since the 2024 map took effect does. We check the layer by address before your listing goes live.

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 and releases them free; the county’s floodplain line is (239) 252-2942. Surveyed floors on the two certificates read in full sit about 2.1 and 1.4 feet above the base flood elevation. Put the certificate in the listing file.

Can a Letter of Map Revision help me sell?

It can. About 15 Winding Cypress homes have obtained single-lot FEMA letters since 2024 placing them in shaded Zone X, and a lender, while keeping the option to require flood insurance, usually quotes such a home differently. Whether your lot qualifies depends on the surveyed elevations, so the Elevation Certificate is the first document to pull.

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

Florida’s flood disclosure law, section 689.302, Florida Statutes, created in 2024, requires a seller to disclose known flooding, any flood insurance claims filed on the home and any federal flood assistance received. The form is given to the buyer at or before contract. FEMA’s claims data show three claims in the wider Census block group, all from Irma in 2017, none paid, and none since, but you answer the form from your own records.

Did Hurricane Ian hurt home values in Winding Cypress?

The record points the other way. The district’s November 2022 minutes 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, after Ian, before resetting to $860,000 in 2025.

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, and Winding Cypress homes were built from 2015 to 2023, so they reach that line from about 2034. Tile roofs need a remaining-life proof only after 50 years. A pre-listing inspection that flags small items still 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 form documents roof shape, roof-to-wall connections, roof deck attachment and opening protection, can lower the buyer’s wind premium and stays valid for up to five years, with a new form in effect since April 1, 2026. DiVosta built with engineered trusses, hurricane tie-downs and galvanized steel shutters as standard, and those features score; impact glass, where installed, scores too.

Will my buyer’s property taxes be higher than mine?

Very likely, if you are homesteaded. Save Our Homes caps follow the owner, not the house, so the home is reassessed after the sale. Applied at the 2025 rate of 10.5058 mills to the $875,000 single-family median, the ad valorem illustration is about $9,193 a year before exemptions, plus the district line and the $261.91 solid-waste charge. That illustrates the mechanism and is not a quote for any home.

What does it cost to own a Winding Cypress home each year?

Before property tax and insurance, the association, district and solid-waste lines total about $8,153.64 a year for a villa, $8,668.65 for a Classic home on Phases 1 and 2, $9,184.11 for an Estate home on Phases 1 and 2, $9,143.65 for a Classic home on Phase 3 and $9,668.11 for an Estate home on Phase 3, by our sums of the published 2026 lines. Your buyer will ask for the row that fits your home.

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 Declaration also restricts using the Winding Cypress name or logo in promotional material except to identify where a property is, so your listing can name the community as its location but cannot use the association’s logo or imply its endorsement.

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

Through the association’s visitor and agent process at the Collier Boulevard gatehouse, where attendants work alongside license-plate readers and a virtual callbox. Residents issue mobile guest passes through the SAGE app. When you list, we register scheduled showings in advance so agents and their buyers are not held at the gatehouse.

Can I rent my Winding Cypress home instead of selling?

Yes, with Board approval and within the recorded 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, with tenants screened through Tenant Evaluation. Seasonal leasing works within those rules; nightly rentals do not. Holding also keeps the association and district obligations, and giving up homestead can raise your own tax bill.

Do Winding Cypress villa sellers face different rules?

Yes, in three ways. Villa owners maintain their own villa and carry replacement-value insurance on it under party-wall, shared-roof and party-fence provisions, so a buyer will ask for your policy and any shared-roof history. Villas pay the lowest association amount, $6,247.75 in 2026, and the lowest district amount, $1,643.98. And villas sold faster this year, at a 50-day median.

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. Public data do not isolate a preserve or lake premium, because 48 sales in a year cannot separate view from size, plan and condition. We price it from the specific sales that had one, and the view itself is the strongest photograph in the listing.

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, 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 and preserve views. Price against the resale comparables and show the fee stack clearly.

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 at Collier Boulevard and Rattlesnake Hammock Road, targeting fall 2026, though the opening date is not yet confirmed. It joins Publix at Freedom Square, 1.7 miles from the gate, and is worth a line in your listing once it opens.

Should I sell furnished or turnkey?

With 43.7 percent of Winding Cypress households part-time, a share of buyers is buying a seasonal home and would rather not furnish it, so a turnkey offer can widen the audience. It rarely adds its replacement cost to the price. Price the home first, then treat the furnishings as a negotiating asset that removes friction for the right buyer.

Should I sell my Winding Cypress home without an agent?

You can sell without an agent in Florida. In Winding Cypress the buyer is usually represented, the buyer’s agent will ask about the district line, the flood file and the association timeline, and the contract has to carry the statutory disclosures. The risk is rarely the paperwork itself; it is a contract that fails late because nobody sequenced the notice, the estoppel and the flood questions.

Should I take a cash offer instead of listing?

Compare the net, not the word cash. Instant offers price in a discount for speed, and in a market with 2.2 months of supply that discount is usually larger than the cost of a well-run listing. If speed matters most, a quiet, targeted sale through direct agent outreach can often be both fast and competitive. We will lay the two options side by side for you.

Will I owe capital gains tax when I sell?

Possibly. Florida has no state personal income tax, so the exposure is federal, and a qualifying primary residence exclusion can shelter a substantial part of the gain, per IRS Publication 523. A second home or rental does not qualify for that exclusion. Talk to your CPA before you sign a contract, not after.

I inherited a Winding Cypress home. What changes?

Inherited property generally takes a basis adjusted to fair market value at the date of death, which can sharply reduce taxable gain on a sale, so a documented date-of-death valuation matters. Title may need probate unless the home was held in a trust, jointly with survivorship, or under a transfer on death mechanism. The association’s 20-day notice and estoppel apply to the eventual sale exactly as they do to any other.

What documents will my Winding Cypress buyer ask for?

Expect requests for the association estoppel certificate, the district’s FY2026/27 budget and your tax bill showing your district amount, your Elevation Certificate, any FEMA letter for your lot, a wind mitigation report, the state flood disclosure, and the recorded Declaration and 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.

What should I do first if I am thinking about selling?

Three things, in order. Get a written valuation built from the sales of your own series and plat. Pull your Elevation Certificate, any FEMA letter and your latest tax bill so the flood and district questions are answered. Then decide how public or private the marketing should be. Request a valuation through our Winding Cypress home valuation request or call Jesse McGreevy at (239) 898-6072.

Sources and Authoritative References

Every figure on this page traces to a primary source below, listed as of September 24, 2026: the Southwest Florida MLS, Collier County’s recorded instruments and public layers, the Winding Cypress association and district’s own published documents, Florida Statutes and state agencies, and FEMA and other federal agencies. No listing portal or competing brokerage is cited.

Market data and county records

• Southwest Florida MLS, Matrix (Winding Cypress closed, active and pending listings, pulled September 23, 2026; Verona Walk and East Naples benchmark searches, pulled September 23 and 24, 2026)
• Collier County Growth Management parcel layer (plats, lots, preserve tracts)
• Florida Department of Revenue statewide cadastral layer (qualified sales, year built)
• Florida Department of Revenue, sale qualification codes
• Florida Department of Revenue, property tax exemptions and portability
• Collier County Tax Collector, 2025 bill for a homesteaded Phase 2 home
• Collier County Tax Collector, 2025 bill for a Jacaranda Lane villa
• Collier County Tax Collector, 2025 bill for a Phase 3 home
• Collier County Clerk, official records search
• Collier County Clerk, Amended and Restated Declaration, OR 6330 PG 3383
• Collier County Clerk, sample association Certificate of Approval
• Collier County Clerk, hurricane shutter amendment, OR 6507 PG 955
• Collier County Clerk, Cost Sharing Agreement with the Verona Walk association, OR 5011 PG 1411
• Collier County Clerk, notice of Series 2015 special assessments
• Collier County Clerk, notice of Series 2019 special assessments
• Collier County Clerk, first DiVosta sale to a buyer, June 30, 2015
• Collier County Clerk, last DiVosta sale to a buyer, December 21, 2023
• Collier County Clerk, Phase One plat index entry
• Collier County Clerk, conservation easement to the South Florida Water Management District
• Collier County Clerk legal notice, Hearing Examiner court conversion appeal, March 13, 2026
• Collier County Community Development District boundaries layer
• Collier County CityView projects layer

The Winding Cypress association and district

• Winding Cypress Homeowners Association, official site
• Winding Cypress association, 2026 Approved Budget
• Winding Cypress association, Amended and Restated Declaration, Articles and Bylaws
• Winding Cypress association, Rules and Regulations, 2026 final draft
• Winding Cypress association, Rules and Regulations, May 2024
• Winding Cypress association, 2025 audit, owners copy
• Winding Cypress association, 2025 Rimkus Reserve Study Update
• Winding Cypress association, certified 2025 survey results
• Winding Cypress association, 2025 Year in Review
• Winding Cypress association, Board minutes, September 16, 2025
• Winding Cypress association, Visitors and Agents
• Winding Cypress association, Community Amenities
• Winding Cypress association, sale and lease application through Tenant Evaluation
• Winding Cypress Community Development District, official site
• Winding Cypress CDD, frequently asked questions
• Winding Cypress CDD, FY2026/27 Final Budget
• Winding Cypress CDD, FY2022/23 Final Budget
• Winding Cypress CDD, Collier County Ordinance 2015-48
• Winding Cypress CDD, LJA Engineering lake assessment, March 21, 2024
• Winding Cypress CDD, February 7, 2023 board book with the November 2022 minutes
• Verona Walk CDD, FY2026/27 adopted budget

Florida statutes and state agencies on selling

• Florida Statutes 201.02, documentary stamp tax on deeds
• Florida Department of Revenue, documentary stamp tax
• Florida Statutes 720.401, homeowners association disclosure summary
• Florida Statutes 720.30851, homeowners association estoppel certificates
• Florida DBPR, estoppel certificate fee schedule
• Florida Statutes 190.048, community development district disclosure
• Florida Statutes 689.261, property tax disclosure summary
• Florida Senate, CS/CS/HB 1049 (2024) staff analysis, residential flood disclosure
• Florida Administrative Code Rule 69O-186.003, title insurance rates
• Florida Department of Financial Services, title insurance overview
• Johnson v. Davis, 480 So. 2d 625 (Fla. 1985)
• National Association of REALTORS, settlement frequently asked questions
• National Association of REALTORS, written buyer agreements
• Florida Division of Corporations entity search
• Internal Revenue Service, FIRPTA withholding
• Internal Revenue Service, Publication 523, selling your home

Flood, storm and insurance

• FEMA National Flood Hazard Layer, flood hazard zones
• FEMA National Flood Hazard Layer, base flood elevation lines
• FEMA National Flood Hazard Layer, LOMA and LOMR-F points
• FEMA LOMR-F 19-04-5181A, builder-era Phase 3 letter
• FEMA LOMR-F 26-04-3737A, a 2026 single-lot letter
• FEMA Map Service Center search
• FEMA online Letter of Map Change portal
• FEMA MT-1 application forms
• FEMA Community Rating System
• OpenFEMA NFIP Community Status Book, Collier County
• OpenFEMA NFIP claims, the Winding Cypress Census tract
• National Hurricane Center storm surge risk maps
• Collier County Elevation Certificates layer
• Collier County Elevation Certificate, Live Oak Drive, 2015
• Collier County 2026 flood protection newsletter
• Collier County hurricane evacuation zone layer
• Citizens Property Insurance, inspections
• Citizens Property Insurance, flood insurance coverage rules
• Florida Office of Insurance Regulation, wind mitigation resources

Builder, community and area

• DiVosta Homes, Winding Cypress digital brochure
• DiVosta Winding Cypress page, archived December 15, 2014
• DiVosta Winding Cypress page, archived September 18, 2016
• Florida Weekly, DiVosta introduces four new floor plans at Winding Cypress, December 3, 2020
• DeAngelis Diamond, Winding Cypress Amenity Center
• Florida Natural Areas Inventory, conservation lands layer
• Florida Forest Service, Picayune Strand State Forest
• Collier County Public Schools, address lookup for 2026-27
• Florida Department of Education, 2026 school grades
• AHCA Florida Health Finder, Physicians Regional Medical Center Collier Boulevard
• OpenStreetMap routing from the Collier Boulevard gate
• Collier County Parks, beach parking information
• Collier MPO 2050 Long Range Transportation Plan
• WGCU, a second Costco for Collier County, October 15, 2025
• Mattamy Homes, land purchase for Summerlit, July 15, 2024

Our own assets

• McGreevy and Comisar Winding Cypress community guide
• McGreevy and Comisar Naples real estate guide
• McGreevy and Comisar Verona Walk community guide
• McGreevy and Comisar free home valuation
• How we represent buyers in Naples
• Jesse McGreevy agent profile
• Marc Comisar agent profile
• Domain Realty Group
• McGreevy and Comisar Google Business Profile

Downloadable Documents

Every row below links the authority that publishes the document, so a Winding Cypress seller or buyer always sees the official, current version rather than a copy. We host nothing ourselves. Two items that matter to a sale are not published and cannot be linked: the association’s application fee, which is set by the Board, and its actual estoppel fee, which prints on the certificate itself.

Your Winding Cypress Listing Team, and How to Reach Us Today

McGreevy and Comisar list and sell homes across Southwest Florida from an office in Bonita Springs, and Winding Cypress sits inside the East Naples market they work every week. If you are weighing a sale in Winding Cypress, the first conversation costs nothing and usually saves a seller more than any decision made later.

The Accolades, Verbatim

• 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

Contact McGreevy and Comisar

Jesse McGreevy: (239) 898-6072, [email protected]. Marc Comisar: (239) 287-5873. Office: 24031 S Tamiami Trl #101, Bonita Springs, FL 34134. Call Jesse direct at (239) 898-6072 to start with a free Winding Cypress home valuation, or call Marc at (239) 287-5873 if you are buying.

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).

McGreevy and Comisar lead Domain Realty Group, a full-service Southwest Florida real estate team; learn more at DomainRealtyGroup.com, and read about the partnership on our about McGreevy and Comisar page. Nothing on this page is legal, tax or insurance advice.

Market data from Southwest Florida MLS, pulled September 23, 2026, and from Collier County’s recorded sales file and public layers. Brokered by Domain Realty.