Updated September 2026
Buying in Winding Cypress means HOA and CDD fees that change by series and phase, a Zone AE flood check on every address, and resale records worth reading before you write an offer. McGreevy and Comisar walk you through all of it from the record. Start your buyer consultation or call Jesse direct at (239) 898-6072.
Updated September 2026 · Jesse McGreevy and Marc Comisar, Domain Realty
Buying a home in Winding Cypress, the gated DiVosta community of 766 homes on Collier Boulevard in East Naples, Collier County, Florida 34114, is a resale purchase with its own paperwork. Every home now sells second-hand, a Community Development District line rides on the tax bill, FEMA’s current map places the community in Zone AE, and the association fee depends on which of three product lines you buy. This page is the step by step purchase path. For the full portrait of the community itself, its history, clubhouse, governance and storm record, read our Winding Cypress community guide, and for the wider city, our Naples guide.
If you are choosing an agent before you choose a house, our guide to the best real estate agents in Naples sets the city’s teams side by side on the public record. If you already own inside the gates and are selling to buy, start with how we sell homes in Winding Cypress and a data-backed valuation of your Winding Cypress home. Weighing a different kind of Naples purchase as well? Our Audubon Country Club buyer guide applies the same record-first method to a mandatory-membership golf club in North Naples, and our guide to Verona Walk, the larger DiVosta community next door covers the community most Winding Cypress buyers tour on the same day.
Call Marc Comisar at (239) 287-5873 or Jesse McGreevy at (239) 898-6072. We have been Top 1% Real Estate Agents Nationally Since 2008, and before you spend a Saturday touring, we will tell you which series, which phase and which street your budget actually lives on.
Buying a home in Winding Cypress takes four things most Naples resales do not: a fee stack read by product line and phase, an estoppel certificate from the association, a flood check on the address under FEMA’s February 8, 2024 map, and a notice to the association at least twenty days before closing. Plan the calendar around all four.
Data updated: September 2026 (Southwest Florida MLS, pulled 23 Sep 2026; Winding Cypress HOA 2026 Approved Budget; Winding Cypress CDD FY2026/27 Final Budget; FEMA National Flood Hazard Layer)
Everything below comes from the community’s Amended and Restated Declaration, recorded February 16, 2024 at Official Records Book 6330, Page 3383 in the Collier County Clerk’s official records, from the association’s 2026 Approved Budget, from the district’s FY2026/27 Final Budget, from FEMA’s own flood layers, from Collier County Property Appraiser records and from the Southwest Florida MLS, pulled September 23, 2026. Where the public record is silent, this page says so plainly rather than guessing.
Winding Cypress sits north-east of US 41 (Tamiami Trail East) and east of Collier Boulevard (County Road 951), with US 41 as its south-west border and Verona Walk directly to the north, in unincorporated Collier County with a Naples mailing address. The main entrance is on Collier Boulevard at Winding Cypress Boulevard, where a gatehouse with attendants, license-plate readers and a virtual callbox handle arrivals. A second, automated rear gate with a barcode reader and cameras serves the south end, per the association’s 2025 reserve study.
That location matters on day one. The entry drive from Collier Boulevard is shared with Verona Walk 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 is told the community is “at 41 and 951” and drives to the corner will find an intersection, not a gate. Set the appointment at the Collier Boulevard entrance.
Winding Cypress is 766 homes built by DiVosta Homes, a PulteGroup brand, and every one of them falls into one of three builder product lines, per the unit census in the district’s fiscal 2026/27 budget:
All three lines sit under one homeowners association, the Winding Cypress Homeowners Association, Inc., with no villa or neighborhood sub-associations, and one Community Development District. What differs by line is the association assessment, the district’s debt charge and the comparable sales that set your price. That is why this page is organized around the purchase path rather than around amenities, and why the first question we ask a buyer is which line, not which price.
Three absences decide purchases here as often as any amenity does. There is no golf course; the nearest public golf is Lely Resort’s Mustang and Flamingo Island courses, about seven minutes from the clubhouse. There is no marina and no lake boating; the 29 lakes are district stormwater lakes, and the association’s 2026 Rules (final draft) bar fishing, boats and water toys. And there is no equity club and no separate membership to buy; the clubhouse and courts are bundled into the association assessment for every home.
Add one more line a buyer should hear early: DiVosta closed its last Winding Cypress home in December 2023, per the last builder-to-buyer deed in the Clerk’s records. There is no builder inventory to compare against, no model park and no incentive program. Every purchase is a negotiation with an owner.
McGreevy and Comisar represent Winding Cypress buyers from the recorded record outward: the 2024 Declaration, the association’s 2026 budget, the district’s budgets and bond notices, FEMA’s 2024 flood map and the Southwest Florida MLS. We have been Top 1% Real Estate Agents Nationally Since 2008 and the #1 Team in Southwest Florida since 2012.
That combination of market volume and primary-source discipline is what this community rewards, because the facts that decide a Winding Cypress purchase, the series fee, the phase debt, the flood letter on the lot, the leasing cap, live in recorded instruments and public budgets rather than in listing remarks.
As the leaders of Domain Realty Group, our team has closed over $2.5 billion in real estate. Those are career numbers across Lee and Collier County. McGreevy and Comisar lead Domain Realty Group, a full-service Southwest Florida real estate team. Learn more about our team at DomainRealtyGroup.com.
We are a top-reviewed Southwest Florida real estate team, and the quotes below are genuine verified Google reviews from real clients, rendered in each client’s own words. We publish no aggregate score and no star average. You can read every review yourself on our Google Business Profile.
★★★★★ “Marc is one of the most down to earth realtors that really listens to your needs and is exceptional at finding the right house.” Verified Google review
★★★★★ “He knew the area and therefore knew exactly where to take us to find the exact kind of neighborhood we were looking for and he was right on the money.” Verified Google review
★★★★★ “Working with Jesse and his team was truly an amazing experience. From the very beginning, they were professional, attentive, and incredibly knowledgeable. They guided us through every step of the process with patience and clarity, always making sure we felt comfortable and informed with every decision.” Verified Google review
★★★★★ “No one knows real estate, especially Florida real estate like Marc and Jesse. Smart and savvy. They also have a great team that is knowledgeable and professional.” Verified Google review
★★★★★ “We love working with Marc and Jesse at Domain. The entire team is professional and top notch. They go above and beyond for their clients. Highly recommend” Verified Google review
Winding Cypress is governed by one homeowners association and one Chapter 190 special district, the Winding Cypress Community Development District, created by Collier County Ordinance 2015-48. The association bills three different annual totals by series; the district bills five different totals by product and phase; and the flood answer can change from the community’s zone to the lot’s own FEMA letter. An agent who has not read those documents cannot tell you what you will pay or what you will be allowed to do with the house.
What we owe you is specific: the estoppel certificate ordered the day the contract is signed, the district’s budget tier for the exact lot, the elevation certificate and any FEMA letter pulled for the exact address, a wind mitigation report read against the builder’s specification, and a carrying-cost model built on the tax bill you will pay rather than the one the seller pays today.
This page runs long on purpose, in the order a purchase actually happens. Use the list below to jump to the section you need, or read it end to end before your first tour.
We track Winding Cypress through two independent records rather than a portal: the Southwest Florida MLS, which counted 48 closings in the twelve months to September 23, 2026, and Collier County’s recorded deeds, which show 39 DOR-qualified sales from September 2025 through June 19, 2026, every one a resale and none builder-direct.
Data updated: September 2026 (Southwest Florida MLS, pulled 23 Sep 2026; Collier County Property Appraiser records, qualified sales file with newest recorded sale 19 Jun 2026)
In the last 12 months we tracked every Winding Cypress closing in both systems. The MLS count is 48 closed listings from September 24, 2025 to September 23, 2026 at a median sale price of $807,500, the midpoint of the two middle sales, $800,000 and $815,000, because 48 is an even count. The county count comes from Collier County Property Appraiser records of qualified, arms-length sales (Florida Department of Revenue sale qualification codes 01 and 02 only, which excludes $100 transfers, quitclaims and corrective deeds): 39 qualified sales of improved homes from September 2025 through the newest sale in the file, recorded June 19, 2026, at a median of $835,000 across a range of $455,000 to $1,495,000. The county file ends three months before the MLS window does, which is why the counts differ, and we treat the MLS as the lead record.
We tracked the association and district fees for all three product lines and both debt phases, the flood zone and base flood elevation at thirteen sampled addresses across every plat, the 230 Elevation Certificates Collier County holds on Winding Cypress streets, three actual 2025 tax bills and the recorded Declaration section by section. That is the evidence base behind every figure on this page.
The county split matters for a buyer in one plain way. In communities where a builder is still selling, most new homes close direct and never reach the MLS, so an MLS-only view undercounts the market and a resale buyer competes with incentives. Winding Cypress is past that stage. Of the 39 qualified sales on the county record for the last twelve months, zero were builder-direct and 39 were resales, and the MLS count of 48 is higher than the county count, not lower. Your competition is other owners’ listings, and your negotiation is with an owner, not a sales office.
That also tells you where the comparable sales come from. Every comparable for a Winding Cypress home is now a resale of a DiVosta home of known plan, series and year, which makes the comparable set cleaner than in most Naples communities.
Every figure on this page describes the Winding Cypress market, not McGreevy and Comisar. Our credentials are stated in the section above as career numbers across Lee and Collier County. A buyer deciding what to offer on a Classic Series home on Pennyroyal Drive needs the Pennyroyal Drive record and the Phase 3 debt tier, not an agent’s scoreboard.
When you sit down with us, we will walk the specific series, the specific lot exposure, whether preserve, lake or street, and the specific comparable set for the home you want, and we will show you the source line for every figure we use.
We bring three things to a Winding Cypress offer that a general Naples search does not. First, the sale-to-list and days-on-market record by product line, which tells you how much room there usually is. Second, the association and district fee for the exact lot, which tells you what the house costs to carry before the estoppel arrives. Third, the flood position of the exact address, including whether it holds its own FEMA letter, which tells you whether flood insurance is a line item, a lender’s option or a negotiating point.
The Winding Cypress market is tight but negotiable. The Southwest Florida MLS recorded 48 closings in the twelve months to September 23, 2026, at a median of $807,500, a median 73 days on market and a median sale-to-list ratio of 95.67 percent, against 9 active listings, about 2.2 months of supply.
Data updated: September 2026 (Southwest Florida MLS, pulled 23 Sep 2026)
Measure, trailing twelve months | All homes | Single-family | Attached villas |
|---|---|---|---|
Closed sales | 48 | 35 | 13 |
Median sale price | $807,500 | $875,000 | $575,000 |
Median list price | $829,999.50 | $925,000 | $599,900 |
Price range | $455,000 to $1,495,000 | $575,000 to $1,495,000 | $455,000 to $635,000 |
Median living area | 2,081 sq ft | 2,158 sq ft | 1,554 sq ft |
Median sale price per sq ft of living area | $394.83 | $405.92 | $370.01 |
Median sale-to-list ratio | 95.67% | 96.26% | 94.76% |
Median days on market | 73 | 76 | 50 |
Closed at or above list | 7 of 48 | 5 of 35 | 2 of 13 |
Total volume | $38,718,900 | $31,433,900 | $7,285,000 |
Single-family and villa splits follow the MLS building-design label on each listing. Two of the 48 closings carry no days-on-market figure, so the all-home days figure uses 46 sales and the single-family figure uses 33. Every price per square foot is per square foot of MLS living area, which is a different denominator from the county roll’s area figures, so never set one beside the other.
At the median, Winding Cypress buyers closed about 4.3 percent below the final asking price over the last twelve months, and only 7 of 48 sales closed at or above list. That sits beside only 9 active listings, which against 48 closings a year is about 2.2 months of supply, a tight number. Both facts are true at once: inventory is thin, and individual buyers are still negotiating on the individual house.
For a buyer that means two things. Do not assume a thin market means paying full price, and do not assume a 4 percent median discount applies to every listing. Villas negotiated a little harder, at a median 94.76 percent of list, while single-family homes closed at a median 96.26 percent. The spread comes from homes priced ahead of their series and street, and our job is to tell you which kind of listing you are looking at before you write.
Nine Winding Cypress homes were active on September 23, 2026: seven single-family homes at a median list price of $1,250,000, ranging from $920,000 to $1,349,500, and two villas listed at $575,000 and $599,900. Two more were under contract, one pending with a contingency at $1,200,000 and one pending at $799,900. That is the whole community, every product line, at one moment.
Read the single-family asking prices against the closed record: a median ask of $1,250,000 sits well above the twelve-month closed median of $875,000 and near the top of the closed range. Some of that gap is the larger Estate homes that happen to be listed today; some of it is asking price the market has not yet tested. Listings change weekly, so this page publishes the shape of the inventory rather than a list of addresses. For the live list, and for homes about to come to market, call Marc Comisar at (239) 287-5873 or start with how we represent buyers in Naples.
Against the prior twelve months, September 24, 2024 to September 23, 2025, closings rose from 40 to 48, about 20 percent. The all-home median held at $807,500 in both years, built from different pairs of middle sales. The single-family median rose 1.7 percent, from $860,000 to $875,000, while single-family price per square foot of living area slipped 2.8 percent, from $417.66 to $405.92, which means somewhat larger homes sold this year. The villa median rose 2.7 percent, from $560,000 to $575,000, and villa days on market fell from a median of 107 to 50.
These are small samples. Thirteen villa sales can move a median with one or two closings, so read the villa trend as direction, not precision.
Calendar-year medians from the same MLS pull show where prices have been:
Calendar year | Single-family sales | Single-family median | Villa sales | Villa median |
|---|---|---|---|---|
2023 | 27 | $965,000 | 11 | $710,000 |
2024 | 34 | $1,000,000 | 11 | $610,000 |
2025 | 33 | $860,000 | 9 | $537,000 |
2026, to September 23 | 26 | $895,000 | 11 | $575,000 |
The single-family median peaked in 2024 at $1,000,000, reset about 14 percent in 2025 and is up about 4.1 percent so far in 2026. Villas peaked earlier, at $710,000 in 2023, fell about 24 percent to $537,000 in 2025 and are up about 7.1 percent in 2026. The highest sale in the four-year pull was $1,895,000, in January 2024, on Winding Cypress Drive. A buyer today is buying below the peak on both product lines, which is useful context and not a forecast.
The 48 MLS closings were concentrated on a few streets: Winding Cypress Drive 12, Jacaranda Lane 12, Live Oak Drive 10, Pennyroyal Drive 6, Mockingbird Court 3, Blackberry Drive 2, and one each on Cocoplum Street, Clamshell Lane and Geranium Way. Jacaranda Lane is almost entirely villas, so the villa market is effectively a Jacaranda Lane market with a smaller Live Oak Drive block beside it.
The three highest sales of the year were $1,495,000 on Winding Cypress Drive in March 2026, a 3,656 square foot home; $1,475,000 on Cocoplum Street in May 2026; and $1,260,000 on Winding Cypress Drive in November 2025. The three lowest were villas on Jacaranda Lane at $455,000, $460,000 and $470,000.
The single-family and villa columns above follow the building-design field the listing agent entered. Three sales on the villa block of Live Oak Drive, where the county roll records attached villa parcels, carry a single-family label in the MLS, two of them inside the last twelve months. We publish the MLS figures exactly as recorded rather than re-cutting them, and we flag the point so you know that a strictly detached median would likely sit a little above $875,000. When we price a home for you, we check the county roll’s parcel record for every comparable, not only the MLS label.
Winding Cypress produced 48 MLS closings in twelve months against only 9 active listings, and the right home in the right series may list and go under contract inside a few weeks. The buyer who wins it is the one already financed, already holding the fee tier for the lot and already clear on its flood letter.
Buying? Read how we represent buyers in Naples, then call Marc Comisar at (239) 287-5873 or Jesse McGreevy at (239) 898-6072. Selling a home inside the gates to buy another? Start with a valuation of your current Winding Cypress home and Call Jesse direct at (239) 898-6072. We have been Top 1% Real Estate Agents Nationally Since 2008.
A Winding Cypress home costs what its product line and phase say it costs. Over the last twelve months, attached villas closed at a median of $575,000 and single-family homes at $875,000, with the largest Estate homes reaching $1,495,000, and the phase decides whether the district’s debt charge is the lower or the higher tier.
Data updated: September 2026 (Southwest Florida MLS, pulled 23 Sep 2026; Winding Cypress CDD FY2026/27 Final Budget; Collier County parcel layer)
The 152 villas are the entry point to Winding Cypress. They are fee-simple attached villas, paired under shared roofs, on Jacaranda Lane, across the Phase 2 and Phase 2 Replat plats, and on the 7093 to 7202 block of Live Oak Drive, on the Phase One plat. Over the last twelve months, 13 villas closed at a median of $575,000, from $455,000 to $635,000, with a median of 1,554 square feet of living area and $370.01 per square foot.
Villas carry the lowest fees in the community: $6,247.75 in 2026 association charges and $1,643.98 in fiscal 2026/27 district charges. They also carry obligations detached homes do not. Under the Declaration, villa owners maintain their own villa and must insure it at replacement value, and party-wall, shared-roof and party-fence rules govern what one owner can do without the neighbor. A villa buyer should read those sections before writing, not after.
The 406 Classic Series homes are detached, on 50-foot homesites, and make up the middle of the market. DiVosta’s plans for these lots included the Palmary at 1,943 to 2,063 square feet under air, the Prestige at 2,080 to 2,257, the Prosperity at 1,670 to 1,790 and the Mystique at 1,889 to 3,037, per the builder’s Winding Cypress digital brochure, with earlier designs such as the Abbeyville, Martin Ray, Summerwood, Cressida and Infinity. The association’s 2026 total for a Classic home is $6,657.76, and the district charge is $1,748.98 in Phases 1 and 2 or $2,223.98 in Phase 3.
The 208 Estate Series homes sit on 65-foot homesites and hold the top of the market. DiVosta’s Estate plans include the Pinnacle at 2,488 to 3,676 square feet under air, the Tangerly Oak at 2,589 to 2,938 and the Stonewater at 2,852 to 3,894, and the Estate specification added whole-house gutters and a built-in pest-control tube system. The association’s 2026 total for an Estate home is $7,067.22, and the district charge is $1,854.98 in Phases 1 and 2 or $2,338.98 in Phase 3.
The MLS does not split Classic from Estate, and no public record we hold classifies every lot by width, so we match an Estate buyer’s comparables by plan and square footage rather than by a series label.
The county roll counts homes per street; the MLS counts where the last twelve months of sales happened; and the district’s budget sets which debt tier applies. Put together, they give a buyer a working map.
Street | Recorded plat | Homes on the roll | Product | District debt tier | MLS closings, last 12 months |
|---|---|---|---|---|---|
Live Oak Drive | Phase One | 103 | 40 villas plus 63 detached | Phases 1 and 2 | 10 |
Lily Way | Phase One | 16 | Detached | Phases 1 and 2 | 0 |
Clamshell Lane | Phase One | 15 | Detached | Phases 1 and 2 | 1 |
Wiregrass Court | Phase One | 10 | Detached | Phases 1 and 2 | 0 |
Winding Cypress Drive | Phase One, 2, 2 Replat and 3 | 250 | Detached | Phases 1 and 2, or Phase 3 on the Phase 3 plat | 12 |
Blackberry Drive | Phase 2 | 68 | Detached | Phases 1 and 2 | 2 |
Jacaranda Lane | Phase 2 and 2 Replat | 111 | 110 villas plus 1 detached | Phases 1 and 2, villa | 12 |
Arrowhead Way | Phase 2 | 17 | Detached | Phases 1 and 2 | 0 |
Geranium Way | Phase 2 | 15 | Detached | Phases 1 and 2 | 1 |
Chenille Court | Phase 2 | 10 | Detached | Phases 1 and 2 | 0 |
Mockingbird Court | Phase 2C | 23 | Detached | Phases 1 and 2 | 3 |
Pennyroyal Drive | Phase 3 | 53 | Detached | Phase 3 | 6 |
Cocoplum Street | Phase 3 | 33 | Detached | Phase 3 | 1 |
Greenbriar Court | Phase 3 | 29 | Detached | Phase 3 | 0 |
Bromeliad Drive | Phase 3 | 13 | Detached | Phase 3 | 0 |
Total | 766 | 48 |
Two cautions travel with that table. About ten lots recorded on Phase 2-family plats carry the Phase 3 (Series 2019) debt charge, so the plat alone does not settle the tier; the estoppel and the tax bill do. And a street with no sales this year is not a street without buyers; it is a street where no owner listed.
Winding Cypress opened for pre-sales in December 2014 from a temporary sales center, with DiVosta’s archived pages showing a Serenity villa from $263,990 and a community range of $263,990 to $419,990 (DiVosta, December 2014). The model park held its grand opening on Saturday, March 14, 2015. By July 2019 the Serenity started at $312,990 and the Martin Ray at $412,990 (DiVosta, July 2019), and a December 2020 release priced single-family homes from the $400s to the $700s (Florida Weekly, December 2020).
Builder base prices exclude lot premiums and options, so they are a floor rather than a closing figure. Even so, set against a twelve-month villa median of $575,000 and a single-family median of $875,000, they show how much of today’s price is the resale market rather than the original contract.
The five recorded plats hold about 818 acres of preserve tracts, and 70 homesites touch a recorded preserve tract, 46 detached lots and 24 villa lots, 40 of them on the Phase One plat, by our reading of the county parcel geometry. Many other lots back to one of the 29 district lakes. No public dataset measures a preserve or lake premium here, and we will not invent one. What we do is compare a preserve-lot home against the preserve-lot sales in the same series, and a lake-lot home against lake-lot sales, when we build your offer.
Buying in Winding Cypress runs in eight steps: choose the product line and phase, check the address’s flood position, read the fee stack for that lot, write the offer with the right calendar, order the estoppel and budgets, submit the association’s sale application, clear inspections and insurance, and close once the association issues its Certificate of Approval.
Data updated: September 2026 (Winding Cypress Amended and Restated Declaration, recorded 16 Feb 2024; Collier County elevation certificate layer; Florida Statutes, current text)
The order matters because two of those steps run on outside clocks: the association’s notice period, at least 20 days before closing under the Declaration, and a ten business day statutory clock on the association’s estoppel certificate under Florida Statutes Section 720.30851. Put them in the contract at the start and neither will push your closing date.
Decide whether you are buying a villa, a Classic home or an Estate home, then which phase. Villas sit on Jacaranda Lane and the Live Oak Drive villa block. Phase One streets, Live Oak Drive, Lily Way, Clamshell Lane and Wiregrass Court, hold the oldest homes and the most preserve-edge lots. Phase 3 streets, Pennyroyal Drive, Cocoplum Street, Greenbriar Court, Bromeliad Drive and the Phase 3 stretch of Winding Cypress Drive, hold the newest homes, built 2019 to 2023, and the higher district debt tier. The series and phase decide your fee stack and your comparable set before the house decides anything.
Before touring, look up the address on FEMA’s Map Service Center and ask the county’s floodplain staff, at (239) 252-2942, whether an Elevation Certificate is already on file; Collier County holds 230 of them for Winding Cypress streets, free on request, per its Elevation Certificates layer. Then check whether the lot holds its own FEMA letter moving it to shaded Zone X on FEMA’s Letter of Map Change points layer. Get a flood quote on that basis before you write.
Put three documents side by side: the association’s 2026 Approved Budget for the series total, the district’s FY2026/27 Final Budget for the product and phase tier, and the seller’s most recent tax bill for the non-ad valorem lines. Together they give you the carrying cost before insurance and before your own property tax reset.
Write the inspection period long enough to receive the estoppel certificate, the elevation certificate, the wind mitigation report and any FEMA letter. Write the closing date at least 20 days after the seller’s notice to the association can be delivered. And price the offer against the series and street record, the home’s own listing history and the 95.67 percent median sale-to-list rather than against the asking price alone.
Your title agent requests the association’s estoppel certificate in writing, and under Section 720.30851 it must be delivered within ten business days. Florida caps the fee, currently $299 plus $119 for expedited service under the Department of Business and Professional Regulation’s estoppel fee schedule, and the association’s actual charge prints on the certificate. Read it next to the current budget and the current Rules, and confirm the resale capital contribution figure it states.
The seller notifies the association of the sale at least 20 days before closing, and the association’s lease and sale application runs through its screening provider, per the association’s application flyer. The Declaration allows a processing fee; its amount is not published. The Declaration does not allow the association to disapprove a sale, so the application is a notice and records step rather than an approval vote.
Order a general inspection and a wind mitigation inspection on Florida form OIR-B1-1802, and read the wind report against the builder’s specification: steel-reinforced concrete block, engineered roof trusses with hurricane tie-downs, a tile roof, galvanized steel shutters as standard and impact glass as an option. Bind flood coverage early if the lender requires it, because a 30-day waiting period applies to a National Flood Insurance Program policy unless it is bought in connection with a loan.
With the notice given and the application complete, the association records a Certificate of Approval for the purchaser in the public records; a sample recorded certificate sits in the Clerk’s index. At closing, the resale capital contribution appears as a buyer charge, the association and district assessments are prorated, and the deed records. Confirm with your title agent that the certificate and the estoppel figures are in the closing file before the day.
A Winding Cypress owner pays about $8,150 to $9,670 a year before property tax and insurance: the association’s 2026 total of $6,247.75 to $7,067.22 by series, the district’s fiscal 2026/27 charge of $1,643.98 to $2,338.98 by product and phase, and Collier County’s $261.91 solid waste charge.
Data updated: September 2026 (Winding Cypress HOA 2026 Approved Budget, adopted 29 Oct 2025; Winding Cypress CDD FY2026/27 Final Budget; Collier County Tax Collector, 2025 bills)
Winding Cypress publishes its fee stack in the open. The association posts its approved budget on its own site, the district posts its final budget, and three actual 2025 tax bills show the district and county lines as owners pay them. That means a buyer can know the recurring cost of a specific lot before writing, which is not true in a community whose association keeps its budget behind an owner login.
The association’s 2026 Approved Budget bills each series a different total, because lawn and irrigation maintenance is charged by lot front footage:
2026 association charge | Estate Series (65-ft) | Classic Series (50-ft) | Villa Series |
|---|---|---|---|
Maintenance (lawn and irrigation) | $1,775.33 | $1,365.87 | $955.86 |
Common area | $873.89 | $873.89 | $873.89 |
Association operating | $3,103.79 | $3,103.79 | $3,103.79 |
Shady Palm Café fund | $223.89 | $223.89 | $223.89 |
Reserves | $606.32 | $606.32 | $606.32 |
Food and beverage minimum | $484.00 | $484.00 | $484.00 |
Annual total | $7,067.22 | $6,657.76 | $6,247.75 |
Quarterly bill, excluding the food and beverage minimum | $1,645.80 | $1,543.44 | $1,440.94 |
The 2026 assessment is about 1.0 percent lower than 2025: the Estate quarterly bill fell from $1,662.31 to $1,645.80. That direction is worth knowing when you compare Winding Cypress with a community whose fee is rising.
Every home carries a $484 food-and-beverage minimum in 2026, included in the totals above, which funds the Shady Palm Café alongside the $223.89 Shady Palm assessment. The café’s 2026 fund budgets $790,000 of revenue and a planned net loss of $171,500, which those two charges cover. A buyer who never eats at the café still pays both, so count them as part of the fee rather than as an optional spend.
The Winding Cypress Community Development District bills two parts on the property tax bill. The operations and maintenance part is $794.98 for every home. The debt part repays the district’s infrastructure bonds and depends on product and phase, per the FY2026/27 Final Budget:
District assessment area and product | Debt service | Total with O and M, before the 4% November discount |
|---|---|---|
Phases 1 and 2, villa | $849 | $1,643.98 |
Phases 1 and 2, 50-foot homesite | $954 | $1,748.98 |
Phases 1 and 2, 65-foot homesite | $1,060 | $1,854.98 |
Phase 3, 50-foot homesite | $1,429 | $2,223.98 |
Phase 3, 65-foot homesite | $1,544 | $2,338.98 |
Three of those five totals appear exactly on real 2025 tax bills, which pay less if settled in November under Collier County’s early-payment discount. The Phase 3 debt tier runs about $475 to $485 a year higher than the matching Phases 1 and 2 tier, because the Series 2019 bonds financed later infrastructure at later costs.
The operations and maintenance charge rose from $232.06 in fiscal 2022/23 to about $795 in fiscal 2023/24 and has held at $794.98 since, per the district’s FY2022/23 and later budgets. The driver was lake-bank repair: an LJA Engineering lake assessment dated March 21, 2024 logged conditions across all 29 lakes, and the fiscal 2026/27 budget carries a $300,000 lake-bank remediation line with a lake-bank reserve of $366,062 as of July 1, 2026.
In 2023 the district authorized an investigation of lake-bank claims against the developer, per its June 2023 board book. No lawsuit or settlement appears in the public record we reviewed. For a buyer, the practical point is that the lake-bank cost is already in the charge you will pay, not a surprise waiting behind it.
The debt part ends when the bonds retire: the Series 2015 bonds mature in November 2045 and the Series 2019 bonds in November 2049, per the district’s budget and the recorded notices of Series 2015 and Series 2019 special assessments. Bond balances on January 1, 2026 were $6,035,000 for Series 2015 and $3,940,000 for Series 2019. The operations and maintenance part continues for as long as the district maintains the lakes and preserves.
The district’s budget tracks owners who have prepaid their bond assessment, so the debt part can be prepaid; a prepaid lot shows a smaller district line on its tax bill. Ask for the tax bill on the specific lot, because a prepayment by a prior owner benefits you.
Add the association total, the district total and the county’s $261.91 solid waste charge, and the recurring cost of each product line in 2026 is:
Product and phase | Association 2026 | District FY2026/27 | Solid waste | Annual total |
|---|---|---|---|---|
Villa, Phases 1 and 2 | $6,247.75 | $1,643.98 | $261.91 | $8,153.64 |
Classic, Phases 1 and 2 | $6,657.76 | $1,748.98 | $261.91 | $8,668.65 |
Estate, Phases 1 and 2 | $7,067.22 | $1,854.98 | $261.91 | $9,184.11 |
Classic, Phase 3 | $6,657.76 | $2,223.98 | $261.91 | $9,143.65 |
Estate, Phase 3 | $7,067.22 | $2,338.98 | $261.91 | $9,668.11 |
Those totals are our arithmetic on the published figures, before the 4 percent November discount on the district line, and before ad valorem property tax and insurance, which are covered in their own sections below.
Three things are not in a Winding Cypress fee. There is no bulk cable or internet package; the association’s 2026 budget carries only a $4,000 cable line for the whole association, and owners contract service individually. There is no golf. And there is no security service: the Declaration expressly disclaims any obligation to provide security, so the gatehouse is a common expense, not a promise.
One-time and occasional charges sit outside the recurring stack: the $1,050 resale capital contribution a buyer pays at closing (the amount the association’s 2025 audit records across 45 resales in 2025, set each year by the Board), the estoppel fee, a sale application fee whose amount is not published, $25 for each key fob beyond the two issued, and a refundable architectural review deposit of up to $5,000 for a project.
No association special assessment appears in the recorded documents or in the association’s public pages through September 2026. That is a statement about the record, not a guarantee; the estoppel certificate is where a pending or approved special assessment has to be disclosed, which is one more reason it arrives before your deposit goes hard.
A Winding Cypress buyer should hold nine documents before going firm: the association estoppel certificate, the 2026 association budget, the district’s fiscal 2026/27 budget, the seller’s latest tax bill, the elevation certificate, any FEMA letter for the lot, a wind mitigation report, the seller’s flood disclosure and the recorded Declaration with the current Rules.
Data updated: September 2026 (Winding Cypress HOA public documents; Winding Cypress CDD documents page; FEMA National Flood Hazard Layer; Florida Senate staff analysis, HB 1049)
Most of those documents are public. The association posts its budget, Declaration, Rules, audit and reserve study on its own site, the district posts its budgets and engineering reports, Collier County holds the elevation certificates, and FEMA holds the letters. The two that come only through the transaction are the estoppel certificate and the seller’s disclosures.
Document | Why it matters in Winding Cypress | Where it comes from |
|---|---|---|
Association estoppel certificate | States the assessments owed, the resale capital contribution and any special assessment; delivered within ten business days | Requested in writing by your title agent under Section 720.30851 |
2026 association budget | The series total and what it covers | |
District FY2026/27 budget | The product and phase tier, the bond maturities and the lake-bank line | |
Seller’s latest tax bill | The district and solid waste lines as billed, and whether the bond part was prepaid | |
Elevation Certificate | Sets the flood insurance rate | The seller, or the county’s certificate layer |
Any post-2024 FEMA letter | Moves the lot or structure to shaded Zone X, leaving flood insurance to the lender’s option | |
Wind mitigation report | Documents the roof, attachments and opening protection for premium credits | A licensed inspector, on form OIR-B1-1802 |
Seller’s flood disclosure | States known flooding, flood claims and federal flood assistance | The seller, under section 689.302 of the Florida Statutes |
Declaration and current Rules | Leasing, pets, vehicles, fences, shutters, signs and villa party-wall rules |
Two public documents speak to how the association is run. The 2025 audit records 766 units and 45 resales in 2025, and the Rimkus 2025 reserve study update inventories the components the association must replace over time, from the gates to the courts, which the 2026 budget funds at $606.32 per home. Read both before you buy; they tell you whether the reserves line is doing its job.
The Winding Cypress Homeowners Association, Inc., Sunbiz number N14000000923 in the Florida Division of Corporations records, was incorporated January 30, 2014. The original Declaration was recorded November 25, 2014. Members adopted the Amended and Restated Declaration, Articles and Bylaws on February 5, 2024, recorded February 16, 2024 at Official Records Book 6330, Page 3383; an owner amendment recorded in 2023 lowered vote thresholds to a majority, and a 2025 amendment recorded at Official Records Book 6507, Page 955 set the hurricane shutter rule. Owners have controlled the association’s board since February 2022, and residents have controlled the district’s board since mid-2023, with three district seats going to resident voters on November 3, 2026, per the Clerk’s published qualifying-period notice.
Check a Winding Cypress address in three steps: confirm it sits in Zone AE on FEMA’s map effective February 8, 2024, with a base flood elevation of 8.0 feet NAVD88; look for a post-2024 FEMA letter moving the lot to shaded Zone X; and pull its Elevation Certificate, one of 230 the county holds.
Data updated: September 2026 (FEMA National Flood Hazard Layer, flood zones, BFE lines and letter points; Collier County Elevation Certificates layer; NHC National Storm Surge Risk Maps)
Flood is where Winding Cypress listing remarks most often run behind the record. Developer-era letters from 2015 to 2019 moved whole phases out of the high-risk zone, but those letters are marked superseded or not incorporated on the map that took effect February 8, 2024. On that map, every one of thirteen addresses sampled across all five plats sits in Zone AE. Treat any “Zone X” claim about the community as a claim about a specific lot, and verify it.
FEMA’s flood hazard zones layer, panel index and base flood elevation lines return the same answer on every sampled street:
Street | Recorded plat | FEMA zone, map effective Feb 8, 2024 | FIRM panel | Surge on NHC worst-case maps, Category 1 / Category 3 |
|---|---|---|---|---|
Winding Cypress Drive | Phase One, 2, 2 Replat, 3 | AE | 0608J | none / over 3 ft |
Live Oak Drive | Phase One | AE | 0608J | none / over 6 ft |
Lily Way | Phase One | AE | 0608J | none / over 3 ft |
Clamshell Lane | Phase One | AE | 0608J | none / over 3 ft |
Blackberry Drive | Phase 2 | AE | 0608J | none / over 3 ft |
Geranium Way | Phase 2 | AE | 0608J | none / over 3 ft |
Arrowhead Way | Phase 2 | AE | 0616J | none / over 3 ft |
Jacaranda Lane | Phase 2 and 2 Replat | AE | 0616J | none / over 3 ft |
Mockingbird Court | Phase 2C | AE | 0608J | none / over 3 ft |
Cocoplum Street | Phase 3 | AE | 0616J | under 3 ft / over 9 ft |
Pennyroyal Drive | Phase 3 | AE | 0616J | under 3 ft / over 9 ft |
Greenbriar Court | Phase 3 | AE | 0612J | under 3 ft / over 9 ft |
Bromeliad Drive | Phase 3 | AE | 0616J | under 3 ft / over 9 ft |
The base flood elevation line nearest every sampled address is 8.0 feet NAVD88. Two sampled polygons, on Arrowhead Way and Jacaranda Lane, carry a static elevation attribute of 7.0 feet; the panel’s line governs the rating. Chenille Court and Wiregrass Court were not sampled, so we assign them no zone here; check those addresses individually. Panel numbers are Collier County panels 12021C0608J, 0612J and 0616J.
No community-wide map revision exists. Since the 2024 map took effect, FEMA has issued 16 single-lot letters of map revision based on fill, covering 15 homes, moving individual lots or structures to shaded Zone X, mostly on Live Oak Drive in Phase One and Cocoplum Street in Phase 3. One example, LOMR-F 26-04-3737A, is a 2026 letter on Live Oak Drive. For a home with such a letter, the federal mandatory purchase requirement no longer applies, but FEMA’s letter itself states that the lender has the option to continue requiring flood insurance.
If the home you want does not hold a letter, a future owner can apply for one with a surveyor’s elevation data through FEMA’s online Letter of Map Change portal. That is a project, not a closing condition, and it belongs in your plans rather than your contract.
Surveyed Elevation Certificates put Winding Cypress finished floors comfortably above the 8.0 foot base flood elevation. The certificate for a Phase One villa on Live Oak Drive, certified June 8, 2015, records a top of bottom floor of 10.10 feet NAVD88 (Collier County certificate file), 2.1 feet above; one for a Phase 3 home on Cocoplum Street, certified July 9, 2019, records 9.40 feet, 1.4 feet above. Across the certificates reviewed, floors run about 1.4 to 2.7 feet above the base flood elevation. Under FEMA’s current rating method, floor height weighs heavily in the premium, which is why the certificate for the exact home matters more than the zone letter.
Every sampled Winding Cypress address sits in Hurricane Evacuation Zone D on Collier County’s evacuation zone layer; Zone C begins about a kilometer west near Collier Boulevard. Hurricane Ian’s mandatory order in 2022 covered Zone A, and Milton’s in 2024 covered Zones A and B. Zone D was not ordered out in either storm.
The National Hurricane Center’s storm surge risk maps are worst-case planning maps, and they are candid: some surge at Category 1 on the south-west Phase 3 streets, Cocoplum, Pennyroyal, Greenbriar and Bromeliad; most streets reached at Category 2; every sampled street from Category 3; and more than 9 feet everywhere at Categories 4 and 5. After Ian, the district’s minutes recorded that “No significant damage was noted by the community” (district board book, February 2023), and FEMA’s flood claims data for the surrounding area show three claims, all from Irma in 2017, none paid, and none from Ian, Helene or Milton. That area is larger than Winding Cypress, so read it as context, not a guarantee.
Unincorporated Collier County holds Community Rating System Class 5, which gives National Flood Insurance Program policies a 25 percent discount inside the Special Flood Hazard Area and 10 percent outside it, per FEMA’s Community Status Book and the county’s 2026 floodplain protection newsletter. A Winding Cypress home rated in Zone AE receives the larger discount automatically.
Insuring a Winding Cypress home turns on the Zone AE map and any FEMA letter for the lot, the home’s Elevation Certificate and its wind mitigation report. Newer single-family homes in the surrounding Census block group paid a median of about $1,270 for flood coverage on 2026 terms; no record prices a homeowners policy for a specific address.
Data updated: September 2026 (OpenFEMA NFIP policies, 2026 term; Citizens Property Insurance 2026 Rate Kit; Florida Office of Insurance Regulation)
Because the community is Zone AE on the 2024 map, a lender making a federally backed mortgage will require flood insurance on most Winding Cypress homes. A home with a single-lot FEMA letter moving it to shaded Zone X falls outside the federal requirement, and the lender decides. Citizens Property Insurance Corporation also now requires flood coverage on its wind policies for homes in a Special Flood Hazard Area, per its flood coverage rules, so that requirement applies to a Citizens policyholder here unless the lot holds its own letter.
FEMA publishes anonymized policy data by Census block group. In the block group that contains Winding Cypress, 2026-term National Flood Insurance Program policies on single-family homes built 2014 to 2021 had a median cost of about $1,267 for homes rated Zone AE (37 policies) and $1,266 for homes rated Zone X (76 policies), and the middle half of the AE policies ran from about $1,235 to $3,053, per FEMA’s policy dataset. That block group is larger than Winding Cypress and includes other subdivisions, so these are neighborhood figures, not quotes.
Citizens’ 2026 Rate Kit shows Collier County averages moving in different directions by product:
Citizens line, Collier County | Current average | Recommended change | Recommended average |
|---|---|---|---|
All personal lines | $3,470 | down 0.8% | $3,441 |
Homeowners multiperil (HO3) | $4,531 | down 3.1% | $4,391 |
Wind-only | $5,508 | up 4.2% | $5,737 |
Those are county averages across every home age and value, not Winding Cypress quotes. A 2015 to 2023 concrete block home with shutters or impact glass and a documented wind mitigation report generally shops differently from the county average.
A wind mitigation inspection on form OIR-B1-1802 records the roof covering, roof-deck attachment, roof-to-wall connection, roof shape and opening protection that Florida insurers must consider for credits. The Florida Office of Insurance Regulation’s wind mitigation resources note a report stays valid up to five years, and a new version of the form took effect April 1, 2026. DiVosta’s specification for Winding Cypress, steel-reinforced concrete block, engineered trusses with hurricane tie-downs, a tile roof and galvanized steel shutters as standard, is exactly what the form documents. Whether a specific home has impact glass instead of shutters is a question only its own report answers.
Citizens’ inspection rules require a four-point inspection for homes more than 20 years old; the oldest Winding Cypress homes, finished in 2015, reach that age from about 2034 by our arithmetic. Tile roofs need proof of remaining life only after 50 years under the same rules. Private carriers set their own rules, so ask before you bind. The state’s My Safe Florida Home grants require a home built before 2008, so they do not reach these homes.
Winding Cypress permits span three editions of the Florida Building Code: the 2010 code, the 5th Edition (2014), effective June 30, 2015, and the 6th Edition (2017), effective December 31, 2017, per the Florida Building Commission’s effective dates list. A Phase 3 home finished after 2018 was built under a later code than a 2015 Phase One home, which your wind mitigation report and insurer will both notice.
Property taxes on a Winding Cypress home run at 10.5058 mills of taxable value on 2025 bills, plus the district’s $1,643.98 to $2,338.98 and the county’s $261.91 solid waste charge. Three real 2025 bills totalled $6,671.25 to $9,330.52, but your bill resets to market value in the year after you buy.
Data updated: September 2026 (Collier County Tax Collector, 2025 bills; Florida Statutes 193.155; Florida Department of Revenue)
Winding Cypress homes sit in Collier County millage code 21, and a second code, 76, covers part of the footprint at identical rates. The 2025 ad valorem rate was 10.5058 mills, or $10.5058 per $1,000 of taxable value, covering the county, the school board, the Greater Naples Fire Rescue District at 2.0000 mills, the water management district, mosquito control and Conservation Collier, as shown on the 2025 bill for a homesteaded Phase 2 home on Winding Cypress Drive. The district’s charge and the solid waste charge appear on the same bill as non-ad valorem lines.
The three bills below are actual 2025 Collier County tax bills for Winding Cypress homes, and the differences between them are the lesson:
Home | Homestead exemption | 2025 bill, all lines | Source |
|---|---|---|---|
Phase 2 single-family home, Winding Cypress Drive | Yes | $7,724.86 | |
Villa, Jacaranda Lane | No | $6,671.25 | |
Phase 3 single-family home, Bromeliad Drive | No | $9,330.52 |
The villa figure is our sum of the bill’s lines. The Phase 3 home without a homestead exemption paid more than the homesteaded Phase 2 home, partly because of the higher Phase 3 district tier and partly because a non-homestead home carries neither the exemption nor the homestead assessment cap.
Florida’s Save Our Homes rule, Section 193.155 of the Florida Statutes, caps the annual rise in a homesteaded home’s assessed value at 3 percent or the change in the Consumer Price Index, whichever is lower. An owner who has held a Winding Cypress home since 2016 may be taxed on an assessed value well below today’s market value. When you buy, that cap resets: the home is reassessed at just value as of the next January 1, and your first full bill reflects it.
So never budget from the seller’s bill. Budget from the price you are paying, less any exemption you will qualify for, times the millage, plus the district and solid waste lines. We build that number with you before you write.
If the Winding Cypress home will be your permanent Florida residence, file for the homestead exemption with the Collier County Property Appraiser by March 1 of the year after you take title. The exemption removes up to $50,000 of assessed value from taxation (the second $25,000 does not apply to school levies), and it starts the Save Our Homes cap on your own assessment, per the Florida Department of Revenue’s exemption guide. If you are moving from another Florida homestead, portability can carry some or all of that home’s accumulated benefit to the new one, subject to statutory limits and deadlines; the Property Appraiser administers it.
For a seasonal owner, the homestead exemption does not apply, and the full just value is taxed from the first year. The association’s certified October 2025 survey found 43.7 percent of responding households part-time, so a large share of your neighbors pay on that basis.
The district charge is the only special-district assessment on a Winding Cypress bill beyond the county-wide districts in the millage. It is disclosed, budgeted and recorded, and its debt part ends in 2045 or 2049 depending on phase. A buyer comparing Winding Cypress with a community that has no district should add the district line to the comparison rather than treat it as a hidden cost.
The Winding Cypress rules that most often decide a purchase are leasing (30-day minimum, one-year maximum, three leases a year, Board approval), vehicles (boats, trailers, RVs and golf carts garaged), pets (up to three), fences (tightly restricted) and hurricane shutters (up no more than 72 hours around a storm).
Data updated: September 2026 (Amended and Restated Declaration, recorded 16 Feb 2024; Rules and Regulations, May 2024 and 2026 final draft; Certificate of Amendment, recorded 12 Sep 2025)
Everything in this section comes from the Amended and Restated Declaration, the May 2024 Rules and Regulations and the 2026 Rules (final draft). Read the documents yourself before you write; the summary below is the short list of rules that most often make or break a particular buyer.
A Winding Cypress home may be leased for a minimum of 30 continuous days and a maximum of one year, with no more than three leases per calendar year, at least 30 days between lease starts, the whole home only, and Board approval required, with tenant screening through the association’s provider. Rentals under 30 days are treated as a prohibited business use, so short-term vacation rental is not available. A buyer who plans to rent the home in season should model three winter leases at most, not a nightly calendar.
Boats, trailers, recreational vehicles, commercial vehicles, motorcycles and golf carts must be kept inside the garage, and there is no overnight street parking. Golf carts must be registered, insured and driven by a licensed driver, and they may not leave the community. A buyer with a boat on a trailer needs a garage deep enough to hold it or a storage plan outside the gates.
Up to three household pets are allowed. Pit bulls, wolf hybrids and aggressive dogs are excluded, pets are leashed or carried outside the home, invisible fences are not allowed, and pets stay out of the amenity center and the café. Two dog parks, one for small dogs and one for large, sit inside the community.
Fences are tightly restricted and require architectural review approval; the current Rules allow only screening around pool heaters and equipment, so do not buy expecting to fence a yard. In-ground pools go through architectural review, and above-ground pools are prohibited. The architectural reviewer has 60 days to respond, and a refundable deposit of up to $5,000 can be required for a project. Irrigation must connect to the community’s non-potable line.
Under the 2025 amendment, temporary shutters may go up no more than 72 hours before a storm and must come down within 72 hours after it. An absent owner with permanently affixed shutters may keep them closed from June 1 to November 30. For a seasonal owner, that rule is the difference between a home that can be closed for the summer and one that needs someone to put shutters up and take them down.
Signs, including real estate signs, require Board consent or permission in the Rules. When you eventually sell, the association must be notified at least 20 days before closing, it cannot disapprove the sale, and it records a Certificate of Approval for your buyer, the same path you will follow when you buy.
Winding Cypress is not age-restricted. The recorded Declaration contains no housing-for-older-persons provision, and its definition of a family includes children. The fitness center bars children under 13 and requires those aged 13 to 18 to be accompanied, which is a facility rule, not an age restriction on ownership or residence.
The 29 lakes are district-owned stormwater lakes, and the Rules allow no recreational access, including fishing and water toys; expect water levels to move with the seasons on a lake lot. The boardwalk to the preserve overlook closes at sunset, and entry into the preserve itself is not allowed. And the Declaration expressly disclaims any obligation to provide security. The gatehouse attendants and plate readers manage access; they are not a promise, and a buyer should insure and lock up accordingly.
Every Winding Cypress purchase includes The Club at Winding Cypress, a 17,500-square-foot clubhouse by DiVosta’s description, bundled into the association assessment with no separate membership, plus a heated resort pool with lap lanes, the Shady Palm Café, 4 clay tennis courts, 8 pickleball courts, 4 bocce courts and two dog parks.
Data updated: September 2026 (Winding Cypress HOA amenities page and 2026 Rules, final draft; DiVosta archived community page, 2016; Collier County Hearing Examiner notice, 13 Mar 2026)
The clubhouse sits at 7180 Winding Cypress Drive on the association-owned Tract G, built in 2016 per the state roll. DiVosta marketed it as a 17,500-square-foot clubhouse, and its builder, DeAngelis Diamond, describes a 22,000-square-foot amenity center; the two figures measure different things. Membership is mandatory and bundled in the association assessment, with no equity, no initiation fee, no separate membership and no non-resident members; access is by key fob, and owners must be in good standing. Inside are an event room and internet café, a library, a catering kitchen, locker rooms, a fitness center with a Movement Room for classes, and the association office.
For a buyer, “bundled” is the point. There is no club decision to make at closing and no club fee schedule to chase; the cost is already in the $6,247.75 to $7,067.22 association total.
Winding Cypress has 4 Har-Tru clay tennis courts, 8 pickleball courts and 4 Har-Tru bocce courts under the 2026 Rules. In 2026 the association converted one clay tennis court into four asphalt pickleball courts after a Collier County Hearing Examiner appeal of the site plan was denied, per the Clerk’s hearing notice; the completion date has not been published. Pickleball, tennis and bocce each have an owner club, and the Pickleball Club’s 2026 dues are $20 a person. Beyond the gates, East Naples Community Park, home of the US Open Pickleball Championships, is about 14 minutes from the clubhouse.
The heated resort-style pool has lap lanes rather than a separate lap pool, with a spa and cabanas and no lifeguard; the pool heaters were replaced in 2025. The fitness center runs commercial equipment, and the Movement Room holds classes. Outside, a wooden boardwalk leads to a sheltered overlook on the preserve, with a bird-wading overlook, a community garden and a walking path, per the association’s amenities page.
The Shady Palm Café is the association’s poolside bar and restaurant, with its own manager and chef, for residents and their guests; it is not available for private catering. Summer hours are reduced, with the café closed Mondays and Tuesdays. Its costs are carried by the $223.89 Shady Palm assessment and the $484 food-and-beverage minimum on every home.
The association’s clubs page lists Pickleball, Tennis, Bocce, Corvette, Book, Garden, Chatty Crafters, Water Aerobics and Cards and Games clubs, and an Activities Director runs the calendar: dance parties on the pool deck, DJ afternoons at the café, karaoke and a ticketed season-end party in the April 2026 newsletter, plus a holiday craft fair, Oktoberfest and food trucks. With 43.7 percent of responding households part-time in the association’s October 2025 survey, the busiest stretch of the calendar is the winter season.
We find the right Winding Cypress home by matching your budget and priorities to a product line and phase first, then watching a market of about four dozen sales a year to hear about the right house early. The search covers series, lot exposure, flood letter, shutters or impact glass and fee tier before a single showing is booked.
Data updated: September 2026 (Southwest Florida MLS, pulled 23 Sep 2026; Collier County parcel layer)
A price filter on a portal returns a mix of villas on Jacaranda Lane, Classic homes on Blackberry Drive and Estate homes on Winding Cypress Drive that have little in common except the gate. We start the other way round. Tell us whether you want a shared wall or a detached home, how much yard you will keep, whether you plan to lease in season, how you feel about a higher Phase 3 district charge in exchange for a newer home, and whether a preserve view matters, and we will name the two or three streets that fit before we name a house.
With 48 MLS closings in the last twelve months out of 766 homes, roughly one home in sixteen changes hands in a year. The Winding Cypress search is a watch, not a sprint. We track new listings, price changes and relists daily, and we tell you when a home that fits your street list reaches the market, including the history of any home that has been listed before and what it closed for last time.
In a community this size, some homes change hands with little public marketing time. We work the East Naples corridor on Collier Boulevard and US 41 every week, and part of positioning a buyer is being known to listing agents and owners as a financed, prepared buyer with the fee tier and flood file already understood. That preparation is what gets a call before a listing goes live.
On every tour we check four things a listing does not tell you: the series and phase, and so the fee and district tier; what the lot backs to, whether preserve, lake or another home, and what that means for privacy and water levels; the roof, the shutters or impact glass, and the age of the air conditioning and water heater in a home now up to eleven years old; and whether the address holds its own FEMA letter and Elevation Certificate. Agents and visitors enter under the association’s visitors and agents procedure, and residents can issue guest passes through the gate system’s app.
The right way to watch a community producing about four dozen sales a year is a saved search with alerts, tuned to the product line, street and features that matter to you. Set one up through our site and it will notify you when a matching Winding Cypress home is listed. If you would rather we tune it, call Marc Comisar at (239) 287-5873 and describe what you want, or start from our buyer resources for Naples.
We negotiate a Winding Cypress purchase on the record: a 95.67 percent median sale-to-list with only 7 of 48 sales at or above list, a single-family asking median of $1,250,000 against a closed median of $875,000, homes now three to eleven years old, and a fee and flood file the seller should have ready.
Data updated: September 2026 (Southwest Florida MLS, pulled 23 Sep 2026)
We price your offer against the closed sales in the same series and phase, the home’s own listing history including any terminated and relisted runs, and its upgrade record. A home priced ahead of its series is where the 4 percent median discount comes from; a home priced at its series record is one you may need to move on quickly, especially a villa, where the median days on market fell to 50.
Today’s single-family asking prices sit well above the closed record: a median ask of $1,250,000 against a twelve-month closed median of $875,000 and a closed range topping out at $1,495,000. Some of that gap is the mix of larger Estate homes that happen to be listed, and some of it is optimism. We show you where the closed Estate comparables actually landed before you respond to an asking price.
A Winding Cypress home built in 2015 or 2016 is now old enough for its original air conditioning, water heater and exterior paint to be real negotiation items, and old enough that its wind mitigation report may need renewing. A wind report, an Elevation Certificate and a flood quote obtained during the inspection period turn condition into numbers, and numbers are what move a seller.
A Winding Cypress contract has two outside clocks: the ten business day estoppel clock under Section 720.30851 and the association’s 20-day notice before closing. Flood coverage adds a 30-day waiting period outside a loan. We write the inspection period and closing date around those clocks so none of them becomes the seller’s leverage.
Your deposit is protected by the contract’s contingencies and deadlines, and only if you act inside them. We diary every deadline, deliver every notice in writing and on time, and make sure that anything you need to know before you are committed, the estoppel figures, the district tier, the flood letter and the wind report, arrives before the date on which your deposit goes hard.
An appraisal and the county’s assessed value are different numbers built for different purposes. If an appraisal comes in below contract, we go back to the closed sales in the same series and phase, not to the tax roll, to decide whether to renegotiate, bridge the gap or walk.
A Winding Cypress buyer pays ordinary Florida closing costs plus three community items: the $1,050 resale capital contribution set by the Board for 2025, the association’s estoppel fee, capped at $299 plus $119 for expedited service, and the association’s sale application fee, whose amount is not published.
Data updated: September 2026 (Winding Cypress HOA 2025 audit; DBPR estoppel fee schedule; Florida Statutes, current text)
Florida is a promulgated-rate state for title insurance: the premium for a given policy amount is set under Section 627.782 of the Florida Statutes rather than by the individual title agent. What varies is the closing and settlement services around it. Who pays the owner’s title policy is a matter of local custom rather than law, and it is negotiable in every contract, so we raise it at the offer stage.
Two Florida taxes attach to a financed purchase. Documentary stamp tax on the promissory note runs at $0.35 per $100 of the note amount under Section 201.08, and the non-recurring intangible tax on a new mortgage runs at 2 mills under Section 199.133. Neither applies to a cash purchase. Deed recording is charged separately by the Collier County Clerk.
Property taxes are prorated against the seller’s current bill, which is not a forecast of your future bill after the reset. The association assessment is prorated on its quarterly billing. The district charge rides on the tax bill, so it is prorated with the taxes. The resale capital contribution and the application fee appear as separate buyer charges on the settlement statement.
Budget for a general inspection, a wind mitigation inspection on form OIR-B1-1802 if the seller’s report is missing or older than five years, and a survey on a lot backing the preserve or a lake, where knowing exactly where your line sits before you plan a pool is cheaper than finding out at architectural review. A four-point inspection is not required by Citizens for homes under 20 years old, and every Winding Cypress home is under 20.
Florida documentary stamp tax on the deed is $0.70 per $100 of consideration under Section 201.02 and is paid by the seller by custom. Beyond that, seller costs in Collier County are customary rather than statutory and negotiable in every contract. If you are also selling, our page on selling a home in Winding Cypress runs the seller side in full.
The National Association of REALTORS practice changes took effect on August 17, 2024. An agent who participates in a multiple listing service must have a written buyer agreement with you before touring a Winding Cypress home, that agreement must state the agent’s compensation objectively, and offers of compensation are no longer permitted on the MLS.
The agreement must be signed before the tour, in person or by live virtual tour. It must state the amount or rate of compensation so that it is objectively ascertainable, it must prohibit the agent from receiving more than that from any source, and it must carry a conspicuous statement that broker fees and commissions are not set by law and are fully negotiable, per NAR’s written buyer agreements guide and consumer guide.
You do not need a written agreement to talk to an agent about their services, to interview several agents, to ask about a community or to visit an open house and speak to the host. You also do not need one to ask us which district tier a Winding Cypress street carries or whether an address holds its own FEMA letter. The line is the tour.
Compensation to a buyer’s broker can still be negotiated, and a seller can still cover it or offer concessions, but that now happens in the transaction rather than in an MLS field, and the amount your agent may receive is capped by your agreement, per NAR’s settlement questions and answers. You agree what your agent is paid first; then we negotiate separately whether and how much a seller will cover.
In Winding Cypress, representation earns its keep in the diligence: an association fee that changes by series, a district charge that changes by product and phase, a flood answer that changes from the community to the lot, a leasing cap that shapes a seasonal owner’s plans and a tax reset. Read any buyer agreement against that list, and read more about our team and our credentials before you decide.
A Winding Cypress address is zoned for the 2026-27 school year to Lely Elementary, Manatee Middle and Lely High, graded A, A and B by the Florida Department of Education for 2026. Physicians Regional Medical Center on Collier Boulevard is about 3 minutes from the gate, and Naples Pier about 21 minutes.
Data updated: September 2026 (Collier County Public Schools address lookup for 2026-27; Florida Department of Education 2026 school grades; OpenStreetMap routing from the Collier Boulevard gate, run Sep 2026)
The district’s own address lookup returned the same three schools for thirteen sample addresses and every one of the 774 address points on the thirteen lookup streets, with no rezoning flag and the same schools in 2025-26:
School | Address | 2026 / 2025 / 2024 state grade | Enrollment, 2024-25 | Drive from the gate |
|---|---|---|---|---|
Lely Elementary | 8125 Lely Cultural Parkway | A / A / A | 499 | 2.2 miles, about 4 minutes |
Manatee Middle | 1920 Manatee Road | A / A / B | 781 | 3.5 miles, about 6 minutes |
Lely High | 1 Lely High School Boulevard | B / A / B | 1,475 | 3.0 miles, about 7 minutes |
Grades come from the Florida Department of Education’s 2026 school grades file, and enrollment from the National Center for Education Statistics, including Lely High’s record. Lely High offers Cambridge AICE, AP with AP Capstone, dual enrollment with Florida SouthWestern State College, a collegiate high school program with Florida Gulf Coast University, an Embry-Riddle aviation and drone program and career academies, per its curriculum page; it does not offer the International Baccalaureate.
Seats outside the zoned schools come only through the district’s Parental Choice process, and the 2026-27 priority windows have closed; the district accepts a fully executed purchase contract as proof of address for a family moving in. Florida SouthWestern State College’s Collier Campus is about 5 minutes from the gate.
Facility | What it is | Drive from the gate |
|---|---|---|
NCH Immediate Care Southeast, 7717 Collier Blvd | Walk-in care, open daily | 1.7 miles, about 3 minutes |
Physicians Regional Medical Center, Collier Boulevard | 130 licensed beds, 24-hour emergency room, AHCA Level 1 Adult Cardiovascular Services and Primary Stroke Center | 2.2 miles, about 3 minutes |
NCH Baker Hospital, downtown Naples | 391 licensed beds, AHCA Comprehensive Stroke Center, Level 2 Adult Cardiovascular | 10.7 miles, about 20 minutes |
Physicians Regional, Pine Ridge | Comprehensive Stroke Center, Level 2 Adult Cardiovascular | 12.2 miles, about 18 minutes |
NCH North Naples Hospital | 311 licensed beds | 19.2 miles, about 27 minutes |
Gulf Coast Medical Center, Fort Myers | Level II trauma center | 39.4 miles, about 50 minutes |
Licensing and program details come from the Agency for Health Care Administration’s facility profiles for Physicians Regional Collier Boulevard, NCH Baker, NCH North Naples, Physicians Regional Pine Ridge and Gulf Coast Medical Center. A hospital three minutes from the gate is one of the strongest practical facts about this address.
Drive times below run from the Collier Boulevard gate on OpenStreetMap routing without traffic; January to April adds time on Collier Boulevard and US 41.
Destination | Miles | Minutes |
|---|---|---|
Publix, Freedom Square | 1.7 | 4 |
Rookery Bay Environmental Learning Center | 2.3 | 4 |
I-75 Exit 101 | 6.1 | 11 |
Paradise Coast Sports Complex | 6.8 | 12 |
Jolley Bridge to Marco Island | 8.6 | 14 |
Isles of Capri | 9.2 | 16 |
Naples Airport | 9.5 | 17 |
Fifth Avenue South | 9.8 | 18 |
Naples Pier | 11.1 | 21 |
Tigertail Beach, Marco Island | 11.4 | 23 |
Waterside Shops | 16.3 | 26 |
Mercato | 18.5 | 29 |
Southwest Florida International Airport | 38.8 | 49 |
Collier County property taxpayers and full-time residents qualify for a free annual beach parking permit valid at county and City of Naples beach lots, per Collier County Parks’ beach parking page; Tigertail Beach charges $10 to park without it. The nearest public boat launch is the Collier Boulevard Park Boat Ramp just north of the Marco Island bridge, reopened August 13, 2025, with a $10 launch fee and free parking for resident permit holders. From the clubhouse, Lely Resort’s public golf is about 7 minutes and Collier-Seminole State Park about 16.
The Picayune Strand State Forest boundary is about 140 meters, under a tenth of a mile, from 7478 Winding Cypress Drive, on the state’s conservation lands layer, and the forest covers 74,138 acres under the Florida Forest Service. That is the view, and it comes with two things a buyer should know: the state runs prescribed burns there, including an 818-acre burn that began December 10, 2025 (WINK News), and Collier County carries a very high wildfire-risk rating on the USDA Forest Service’s Wildfire Risk to Communities map. Wildlife is part of life here too; a family of four black bears was filmed inside the community in January 2025 (WINK News).
Near Winding Cypress, Collier Boulevard is funded for widening from four to six lanes south of Manatee Road in the 2050 long range plan, a second Collier Costco is under construction about 3 miles north, and Mattamy’s Summerlit adds 249 homesites nearby. None changes the community’s own inventory of 766 homes.
Data updated: September 2026 (Collier MPO 2050 Long Range Transportation Plan, adopted 11 Dec 2025; Collier MPO FY2027-2031 TIP; news reports as dated)
The Collier Metropolitan Planning Organization’s 2050 Long Range Transportation Plan, adopted December 11, 2025, lists the Collier Boulevard widening from four to six lanes, south of Manatee Road to north of Tower Road, as cost feasible in its second plan period, at a present-day cost of $14.80 million. An overpass carrying US 41 over Collier Boulevard and a Benfield Road extension to US 41 appear as unfunded needs. The current transportation improvement program for fiscal 2027 to 2031 carries no construction project at the US 41 and Collier Boulevard intersection, only resurfacing nearby.
A second Collier County Costco, about 162,700 square feet, was approved in October 2025 at Collier Boulevard and Rattlesnake Hammock Road, about 3 miles north, and was reported targeting a fall 2026 opening (Marco Eagle, March 2026; WGCU, October 2025). The opening date is not confirmed.
Within about a mile, Mattamy Homes’ Summerlit community adds 249 homesites on about 65 acres (Mattamy Homes, July 2024), and Ekos Creekside is building 160 affordable rental homes on Collier Boulevard (Gulfshore Business). About 1.1 miles from the planned development’s edge, Collier County approved the 1,299-home Greenway Fritchey project on December 9, 2025 (Gulfshore Business). For a Winding Cypress buyer, new construction nearby competes for some of the same East Naples buyers, though without a finished clubhouse and courts; it also means more traffic on Collier Boulevard in season.
The Picayune Strand Restoration Project was declared complete at a ribbon cutting on January 28, 2026, per the South Florida Water Management District and the Everglades Foundation. Its levee north of US 41 protects existing developed land. No public document models its effect on Winding Cypress water levels, and we will not claim one.
Winding Cypress and Verona Walk are next-door DiVosta communities on Collier Boulevard, and buyers who tour one usually tour the other. Choose Winding Cypress for newer homes, one bundled clubhouse and a smaller community of 766 homes; choose Verona Walk for a lower entry price, 1,920 homes and a deeper resale market.
Data updated: September 2026 (Southwest Florida MLS, Winding Cypress pulled 23 Sep 2026 and Verona Walk pulled 24 Sep 2026, trailing twelve months; Winding Cypress HOA 2026 budget; Winding Cypress CDD and Verona Walk CDD FY2026/27 budgets)
Winding Cypress and Verona Walk are two halves of one approval. The Winding Cypress PUD, about 1,928 acres approved for 2,854 units, covers both Verona Walk and Winding Cypress, per Collier County’s PUD layer. DiVosta built both, and the two share the entry facilities off Collier Boulevard under the 2014 cost-sharing agreement. Our full guide to Verona Walk and its Town Center covers that community in depth; this section sets the two side by side for a buyer.
Question | Winding Cypress | Verona Walk |
|---|---|---|
Homes | 766: 152 attached villas, 406 Classic and 208 Estate detached homes | 1,920: about 944 attached and 976 detached |
Age restriction | None; all-ages covenants | None; open to all ages |
Builder and era | DiVosta; first home closed June 30, 2015, last December 21, 2023 | DiVosta |
Clubhouse | The Club at Winding Cypress, association-owned, bundled in the assessment, no initiation | Association-owned Town Center, no club initiation |
Annual association fee, 2026 | $6,247.75 to $7,067.22 by series, published in the approved budget | Not published by the association |
District charge, FY2026/27 | $1,643.98 to $2,338.98 by product and phase, before the 4% November discount | $744.85 to $992.85 by home type |
Closed sales, last 12 months (MLS) | 48 | 97 |
Median sale price (MLS) | $807,500 | $494,000 |
Attached median | $575,000 | $440,000 |
Detached median | $875,000 | $705,000 |
Median price per sq ft of living area | $394.83 | $306.19 |
Median days on market | 73 | 53 |
Median sale-to-list ratio | 95.67% | 96.31% |
The Verona Walk district figures come from its fiscal 2026/27 adopted budget. The two MLS columns cover trailing twelve-month windows ending a day apart, September 23 and September 24, 2026, and Winding Cypress’s attached and detached split follows the MLS building label while Verona Walk’s follows the county’s building footprint, so read the split rows as close cousins rather than identical cuts.
Three things stand out. First, the median Winding Cypress sale ran $313,500 above the median Verona Walk sale, a gap that reflects more heavily detached housing: 614 of Winding Cypress’s 766 homes are detached, against about half of Verona Walk’s. Second, the gap per square foot of living area is narrower, $394.83 against $306.19, so much of the price difference is home size rather than price per foot. Third, Verona Walk closes about twice as many homes from a base of 1,920 against 766, 97 closings against 48, and a little faster, a median 53 days on market against 73.
The district line runs the other way. Winding Cypress’s district charge is more than double Verona Walk’s at the low end, and its bond debt runs to 2045 and 2049. Verona Walk’s association fee is not published, so a full carrying-cost comparison needs its estoppel; ours is on the association’s own site.
Choose Winding Cypress if you want a home built from 2015 to 2023, a published association fee that went down for 2026, one bundled clubhouse with clay tennis, eight pickleball courts and its own café, preserve-edge lots beside the Picayune Strand, and a smaller community of 766 homes. It suits a buyer whose budget reaches the $575,000 villa median or the $875,000 single-family median.
Choose Verona Walk if a lower entry price matters most, with an attached median of $440,000 and a detached median of $705,000, if you want the larger community and deeper resale market of 1,920 homes, and if a lower district charge weighs heavily in your budget. Read our guide to Verona Walk, the DiVosta community next door before you tour.
The table decides the structure. The address decides the rest, because fees, flood letters and resale depth change street by street in both communities. Marc Comisar at (239) 287-5873 will run the same comparison on the two specific homes you are weighing.
Winding Cypress sits between Hacienda Lakes and Naples Reserve on price, with no golf and no equity club. Its twelve-month single-family median of $875,000 is within 1 percent of Hacienda Lakes’ $867,500, about 11 percent higher per square foot of living area, and about 36 percent below Naples Reserve’s $1,372,500.
Data updated: September 2026 (Southwest Florida MLS, closed 0 to 365 days, single-family only, one development name each, pulled 23 Sep 2026)
Community | Sales | Median sale | Median per sq ft of living area | Median living area | Median days on market | Median sale-to-list |
|---|---|---|---|---|---|---|
Winding Cypress | 35 | $875,000 | $405.92 | 2,158 | 76 | 96.26% |
Hacienda Lakes | 38 | $867,500 | $364.61 | 2,475 | 62 | 95.71% |
Naples Reserve | 50 | $1,372,500 | $470.78 | 2,602 | 47 | 96.21% |
Fiddler’s Creek | 98 | $1,299,500 | $505.53 | 2,685.5 | 65 | 94.81% |
Treviso Bay | 20 | $2,062,500 | $736.68 | 2,497.5 | 25 | 94.59% |
Every row uses the same MLS search: closed in the last 365 days, single-family building design only, one development name each. Fiddler’s Creek and Treviso Bay include golf-membership product; Winding Cypress and Hacienda Lakes have no golf, and the MLS search does not state golf status for Naples Reserve. Our guides to Naples Reserve and Treviso Bay cover two of those neighbors in depth.
For a buyer, the table says Winding Cypress is priced as a no-golf, amenity-rich resale community. Against Hacienda Lakes you pay a little more per foot for a gated DiVosta community with its clubhouse built out; against Naples Reserve you give up size and price in exchange for a lower entry. Where you land depends on whether golf, lot size or entry price leads your list.
Winding Cypress is the right purchase for a buyer who wants a 2015 to 2023 home in a gated, bundled-amenity community with a published fee, preserve views and a hospital three minutes away. It is the wrong purchase for a buyer who wants golf, a boat at the house, short-term rental income or a home outside the Zone AE map.
Data updated: September 2026 (Southwest Florida MLS, pulled 23 Sep 2026; Winding Cypress HOA 2026 budget; Winding Cypress CDD FY2026/27 budget; FEMA National Flood Hazard Layer)
A personalized Winding Cypress buyer consultation with McGreevy and Comisar is a conversation, not a sales pitch. We will match your budget to a product line and two or three streets, walk the association and district fees for those lots, check the flood position of any address you have in mind, and tell you honestly whether Winding Cypress fits how you live.
The consultation form sits near the top of this page. You can also call Jesse McGreevy direct at (239) 898-6072 or Marc Comisar at (239) 287-5873, or read how we represent buyers in Naples first. We have been Top 1% Real Estate Agents Nationally Since 2008.
Jesse McGreevy started in Southwest Florida real estate in October 2004 and launched his own team in October 2008. He runs the technology, marketing, data and systems side of the partnership, which is why this page is built on the recorded Declaration, the association’s and district’s own budgets, Collier County’s records, FEMA’s flood layers and the Southwest Florida MLS rather than a portal feed. Reach him at (239) 898-6072 or [email protected].
Marc Comisar runs the field side of the partnership: in the homes, at the inspections and at the closing table. For a Winding Cypress buyer that means the roof, shutters and air conditioning questions on a home up to eleven years old, the preserve or lake exposure of a lot, and the calendar that gets the estoppel, the flood file and the association’s notice lined up with your closing. Reach him at (239) 287-5873.
A Winding Cypress specialist matters because the facts that decide a purchase here, the series fee, the phase debt tier, the lot’s own FEMA letter, the leasing cap and the association’s twenty-day notice, live in budgets and recorded documents that a general Naples search never surfaces. Missing one changes what you pay each year.
Data updated: September 2026 (Southwest Florida MLS, pulled 23 Sep 2026; Winding Cypress HOA and CDD budgets; FEMA National Flood Hazard Layer)
This page is the purchase path. For the community itself, its origins on Barron Collier land, the master plan and preserve, governance, the club, the storm and flood record in full, schools, drive times and the history back to the 1999 development order, read our complete Winding Cypress community guide.
If you are selling a home to buy in Winding Cypress, including a move from a villa to a detached home inside the gates, see how we sell Winding Cypress homes and request a valuation of your Winding Cypress home, or Call Jesse direct at (239) 898-6072.
Jesse McGreevy and Marc Comisar are the local real estate experts behind this Winding Cypress buyer page. They co-founded Domain Realty, lead roughly thirty agent partners across Lee and Collier County, and have spent two decades selling Southwest Florida property, including the East Naples corridor along Collier Boulevard and US 41. Reach Jesse direct at (239) 898-6072.
More about how we work and the team behind us is on our about McGreevy and Comisar page. Together they operate as McGreevy and Comisar under Domain Realty, a brokerage they co-own rather than simply hang a license with.
Jesse McGreevy (Sales Associate) and Marc Comisar (Broker Associate) are licensed Florida REALTORS® with Domain Realty; Florida real estate licensure is regulated by the Florida Real Estate Commission (FREC).
McGreevy and Comisar lead Domain Realty Group, a full-service Southwest Florida real estate team. Learn more about our team at DomainRealtyGroup.com.
These are the questions buyers ask most about purchasing in Winding Cypress, East Naples, Collier County, Florida 34114, answered from the recorded Declaration, the association’s and district’s budgets, Collier County’s records, FEMA and the Southwest Florida MLS. Where the public record is silent, the answer says so.
Winding Cypress sits north-east of the US 41 (Tamiami Trail East) and Collier Boulevard intersection in East Naples, with its main gate on Collier Boulevard at Winding Cypress Boulevard. US 41 forms its south-west border and Verona Walk its north border, per the district engineer’s master report.
No. Winding Cypress is in unincorporated Collier County with a Naples mailing address and ZIP code 34114, and the Census Bureau treats it as its own Census Designated Place on its 2020 places layer. County government, the Sheriff’s Office and the Greater Naples Fire Rescue District serve it.
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, per the district’s fiscal 2026/27 budget. There are no condominiums or apartments.
DiVosta Homes, a PulteGroup brand, built every home, and it closed its last Winding Cypress sale on December 21, 2023, per the Clerk’s deed record. Every purchase since is a resale from an owner.
Over the twelve months to September 23, 2026, the Southwest Florida MLS recorded 48 closings at a median of $807,500: single-family homes at $875,000 and attached villas at $575,000. Sales ranged from $455,000 for a villa to $1,495,000 for a large Estate home.
The median sale closed at 95.67 percent of the final list price over the last twelve months, and only 7 of 48 sales closed at or above list. Villas closed at a median 94.76 percent and single-family homes at 96.26 percent, so a typical negotiation lands a few percent below asking.
Nine were active on September 23, 2026: seven single-family homes at a median list of $1,250,000 and two villas at $575,000 and $599,900, with two more under contract. That is about 2.2 months of supply, a tight market.
The median was 73 days on market over the last twelve months: 76 days for single-family homes and 50 days for villas. Villa time on market fell sharply from a median of 107 days the year before.
The single-family median rose 1.7 percent year over year, to $875,000, while price per square foot of living area slipped 2.8 percent; villas rose 2.7 percent, to $575,000. Both remain below their peaks, $1,000,000 for single-family homes in 2024 and $710,000 for villas in 2023.
No. Collier County’s recorded, DOR-qualified sales for the last twelve months show 39 sales through June 19, 2026, every one a resale and none builder-direct, and the MLS count of 48 is higher than the county count, so the MLS captures this market fully.
The association’s 2026 Approved Budget sets annual totals of $7,067.22 for an Estate home, $6,657.76 for a Classic home and $6,247.75 for a villa, each including a $484 food-and-beverage minimum, billed quarterly.
The assessment covers lawn and irrigation maintenance, common areas, association operations and staff, the clubhouse and amenities, the Shady Palm Café fund of $223.89 and reserves of $606.32. It does not include cable or internet, golf or any security service.
Yes. The Winding Cypress Community Development District bills $1,643.98 to $2,338.98 a year on the property tax bill for fiscal 2026/27, before the 4 percent November discount, depending on whether the home is a villa, a 50-foot or a 65-foot homesite and whether it sits in Phases 1 and 2 or Phase 3.
Lake-bank repair. The operations and maintenance part rose from $232.06 in fiscal 2022/23 to about $795 in fiscal 2023/24 after an engineering lake assessment logged erosion across the 29 lakes, and it has held at $794.98 since.
The Series 2015 bonds mature in November 2045 and the Series 2019 bonds, which Phase 3 homes carry, in November 2049. The operations and maintenance part, $794.98 a year, continues after the bonds retire.
The district’s budget tracks owners who have prepaid their bond assessment, so the debt part can be prepaid, and a prepaid lot shows a smaller district line on its tax bill. The operations and maintenance part cannot be prepaid.
Before property tax and insurance, the association total, the district charge and the county’s $261.91 solid waste charge add up to $8,153.64 for a villa and up to $9,668.11 for a Phase 3 Estate home in 2026, by our arithmetic on the published budgets.
The 2025 ad valorem rate was 10.5058 mills, plus the district and solid waste lines. A homesteaded Phase 2 single-family home paid $7,724.86 in total for 2025, and a non-homesteaded Phase 3 home paid $9,330.52, per Collier County Tax Collector bills.
Usually not. The Save Our Homes cap under Section 193.155 limits a homesteaded owner’s annual assessment increase, and it resets when the home sells, so budget from your purchase price and the millage rather than the seller’s bill.
Yes. The buyer pays a resale capital contribution at closing, $1,050 per resale in 2025 according to the association’s 2025 audit, which recorded 45 resales that year. The Board sets the amount each year.
Florida caps the association’s estoppel fee, currently at $299 plus $119 for expedited delivery under the state’s published schedule, with a higher cap if the account is delinquent. The association’s actual charge prints on the certificate.
No. The seller must notify the association at least 20 days before closing, and the association records a Certificate of Approval, but the Declaration does not let it disapprove a sale. A sale application runs through the association’s screening provider.
None appears in the recorded documents or the association’s public pages through September 2026. The estoppel certificate is where a pending or approved special assessment must be disclosed, so read it before your deposit goes hard.
Yes. The Collier Boulevard entrance has a gatehouse with attendants, license-plate readers and a virtual callbox, and a second automated rear gate serves the south end. The Declaration expressly disclaims any obligation to provide security.
No. The recorded Declaration contains no housing-for-older-persons provision, its definition of a family includes children, and the community is open to buyers of all ages.
The association’s certified October 2025 survey, answered by 360 of 766 households, found 56.3 percent full-time and 43.7 percent part-time, so a large share of owners are seasonal.
Yes, with Board approval: a 30-day minimum, a one-year maximum, no more than three leases a calendar year, 30 days between lease starts, the whole home only and tenant screening. Rentals under 30 days are prohibited.
Only inside the garage. Boats, trailers, recreational vehicles, commercial vehicles, motorcycles and golf carts must be garaged, there is no overnight street parking, and golf carts must be registered, insured, driven by a licensed driver and kept inside the community.
Up to three household pets are allowed. Pit bulls, wolf hybrids and aggressive dogs are excluded, pets are leashed or carried, invisible fences are not allowed, and there are two dog parks inside the gates.
In-ground pools go through architectural review, and above-ground pools are prohibited. Fences are tightly restricted; the current Rules allow only screening around pool equipment, and any fence needs architectural review approval.
Temporary shutters may go up no more than 72 hours before a storm and must come down within 72 hours after it; an absent owner with permanently affixed shutters may keep them closed from June 1 to November 30, under the 2025 amendment.
The attached villas sit on Jacaranda Lane and the 7093 to 7202 block of Live Oak Drive. Both streets also carry detached homes, so check the product line of each listing rather than the street.
Villas are fee-simple attached homes with a median of 1,554 square feet of living area and a twelve-month median sale of $575,000. They pay the lowest association and district tiers, and villa owners maintain and insure their own unit under party-wall and shared-roof rules.
Estate plans include the Pinnacle, Tangerly Oak and Stonewater, from 2,488 to 3,894 square feet under air; Classic plans include the Palmary, Prestige, Prosperity and Mystique, plus earlier designs such as the Martin Ray and Abbeyville, per DiVosta’s brochure.
DiVosta’s specification calls for steel-reinforced concrete block construction, engineered roof trusses with hurricane tie-downs and a tile roof, with galvanized steel hurricane shutters standard and impact glass optional. A home’s own wind mitigation report confirms what it actually has.
A clubhouse with a fitness center and Movement Room, a heated resort pool with lap lanes and a spa, the Shady Palm Café, four clay tennis courts, eight pickleball courts, four bocce courts, two dog parks, a boardwalk to a preserve overlook and a community garden, all bundled in the association assessment.
No separate membership exists. The Club at Winding Cypress is owned by the association and bundled into every home’s assessment, with no equity, no initiation fee and no non-resident members.
No. The nearest public golf is Lely Resort’s Mustang and Flamingo Island courses, about seven minutes from the clubhouse, with no membership required, per Lely Resort Golf.
No. The 29 lakes are district stormwater lakes, and the association’s Rules allow no recreational access, including fishing, boats and water toys.
About 21 minutes to Naples Pier (11.1 miles) and 23 minutes to Tigertail Beach on Marco Island (11.4 miles) from the gate, without traffic. Collier County property taxpayers qualify for a free beach parking permit.
Lely Elementary, Manatee Middle and Lely High for 2026-27, per the district’s address lookup, graded A, A and B respectively by the Florida Department of Education for 2026.
Physicians Regional Medical Center on Collier Boulevard is 2.2 miles and about 3 minutes from the gate, with a 24-hour emergency room, and NCH Immediate Care Southeast is 1.7 miles away. The nearest Level II trauma center is Gulf Coast Medical Center in Fort Myers, about 50 minutes away.
Without traffic, I-75 Exit 101 is 6.1 miles (11 minutes), Naples Airport 9.5 miles (17 minutes) and Southwest Florida International Airport 38.8 miles (49 minutes) from the gate.
Zone AE on FEMA’s map effective February 8, 2024, with a base flood elevation of 8.0 feet NAVD88 at every sampled address, per FEMA’s flood hazard layer. About 15 homes hold their own FEMA letters moving the lot to shaded Zone X.
With a federally backed mortgage, usually yes, because the community is Zone AE. For a home with its own FEMA letter to shaded Zone X, the federal requirement falls away and the lender decides. Nearby newer homes paid a median of about $1,270 for flood coverage on 2026 terms.
Often yes. Collier County holds 230 Elevation Certificates for Winding Cypress streets, free on request, and certificates reviewed show finished floors about 1.4 to 2.7 feet above the 8.0 foot base flood elevation.
Zone D on Collier County’s evacuation map. Hurricane Ian’s mandatory order covered Zone A, and Milton’s covered Zones A and B; Zone D was not ordered out in either storm.
The district’s minutes after Ian recorded that “No significant damage was noted by the community,” and FEMA’s claims data for the surrounding Census area show no Ian flood claims. That area is larger than Winding Cypress, so treat it as context.
Not with Citizens yet. Citizens requires a four-point inspection only for homes more than 20 years old, and the oldest Winding Cypress homes reach that from about 2034. Private carriers set their own rules, so ask before you bind.
The Picayune Strand State Forest boundary is about 140 meters from the community, the state runs prescribed burns there, and Collier County carries a very high wildfire-risk rating on the USDA Forest Service’s map. Expect seasonal smoke.
No community-level crime figure is published. The Collier County Sheriff’s Office serves the area, and its 2024 county-wide rates were 153.5 violent and 714.0 property offenses per 100,000 residents, per FDLE’s offense data.
Publix at Freedom Square is 1.7 miles from the gate, and a second Collier County Costco is under construction about 3 miles north at Collier Boulevard and Rattlesnake Hammock Road, reported targeting fall 2026.
Water and sewer come from the Collier County Water-Sewer District and electricity from Florida Power and Light. DiVosta marketed Winding Cypress as a natural-gas community and listed TECO Peoples Gas as the provider in 2015; confirm current service for the address.
No. The association’s 2026 budget carries no bulk cable or internet package, and owners contract service individually.
Choose Winding Cypress for newer homes, a published association fee and one bundled clubhouse in a community of 766 homes. Choose Verona Walk for a lower median sale of $494,000, a deeper market of 97 sales a year and a lower district charge; see the comparison section above.
Its twelve-month single-family median of $875,000 is within 1 percent of Hacienda Lakes’ $867,500 and about 36 percent below Naples Reserve’s $1,372,500, on the same MLS search of single-family sales.
The contract sets the timeline. The two community clocks, the association’s 20-day notice before closing and the ten business day estoppel delivery, fit inside an ordinary financed closing when they start the day the contract is signed, and they set the practical floor for a cash closing.
Yes, if you tour with an agent who participates in an MLS. Since August 17, 2024, that agent needs a signed written agreement before the tour, stating compensation in an objectively ascertainable way, per NAR’s settlement guidance.
Yes. Broker fees and commissions are not set by law and are fully negotiable, and the written buyer agreement must say so conspicuously. A seller may still agree to cover some or all of your agent’s compensation in the transaction.
Start with how we represent buyers in Naples, then call Marc Comisar at (239) 287-5873 or Jesse McGreevy at (239) 898-6072. In a market with about 2.2 months of supply, being financed and holding the fee and flood file before the right home lists is worth more than any tactic applied afterward.
These questions come from buyers who also have a home to sell, whether elsewhere in Florida, out of state or on another Winding Cypress street. Each answer is a single paragraph, and our Winding Cypress seller page covers the selling side in full.
It depends on your financing and your tolerance for carrying two homes. With about 2.2 months of supply, the right Winding Cypress home may appear before your sale closes, so many buyers arrange financing that lets them buy first. We model both sequences with you before you list.
You can, but with only 9 active listings a sale contingency weakens an offer against a buyer without one. If you need one, pair it with a firm timeline, strong proof of funds and a clean inspection approach, and expect a seller to ask for a kick-out clause.
Yes, and it is a natural move up the product lines, from the $575,000 villa median toward the $875,000 single-family median. You sell under the same association notice and Certificate of Approval process you buy under, and your fee and district tiers change with the new lot.
Florida portability can move some or all of an existing Florida homestead’s Save Our Homes benefit to a new homestead, subject to statutory limits and deadlines. It is administered by the Collier County Property Appraiser, so confirm your specific numbers with that office before you rely on them.
Start with a valuation of your Winding Cypress home built from the recorded sales in your series and phase, then call Jesse McGreevy at (239) 898-6072. A community-wide median says little about a specific Estate or villa home.
Prepare your Elevation Certificate, any FEMA letter for your lot, a current wind mitigation report, your latest tax bill showing the district line and any prepayment, and your permit and upgrade history. Assembled before listing, that file removes the most common source of renegotiation during a buyer’s inspection period.
No. The Declaration assigns the resale capital contribution to the buyer at closing; the 2025 figure was $1,050. As a seller you notify the association of the sale at least 20 days before closing so it can record the Certificate of Approval.
If your out-of-state sale funds the purchase, align the two closings so your Winding Cypress closing follows your sale by a comfortable margin, and build the association notice and estoppel clocks into both calendars. We coordinate with your listing agent in the other state and can refer one if you need one.
That depends entirely on how your Winding Cypress contract was written. A sale contingency with clear deadlines protects the deposit if you act inside them; without one, your deposit is at risk once your other contingencies expire. Decide this before you write the offer, not after.
Yes. District assessments stay with the lot and appear on each year’s tax bill until the bond debt retires, so your buyer inherits the district line for your product and phase. If you prepaid the bond part, show the buyer the smaller bill; it is a selling point.
Sources below were retrieved and checked in September 2026, with the Southwest Florida MLS pulled 23 September 2026 (Verona Walk 24 September 2026), FEMA’s flood layers queried in September 2026 and Collier County’s qualified sales file carrying sales recorded through 19 June 2026. Every figure on this page traces to one of them.
The association and the district
Recorded documents and county records
Flood, storm and insurance
Florida Statutes and buyer representation
Schools, healthcare and local life
Land, preserve and the civic pipeline
Builder, news and history
Our own pages
These are the primary documents behind this buyer page, each linked to the authority that publishes it. The two documents that matter most and are not public are the association’s estoppel certificate and the seller’s disclosures; both arrive through the transaction, as set out in the documents section above.
Document | Authority | Link |
|---|---|---|
2026 Approved Budget, per-series assessments | Winding Cypress Homeowners Association | |
Amended and Restated Declaration, Articles and Bylaws | Winding Cypress Homeowners Association | |
Declaration as recorded, Official Records Book 6330, Page 3383 | Collier County Clerk of the Circuit Court and Comptroller | |
Rules and Regulations, 2026 final draft | Winding Cypress Homeowners Association | |
FY2026/27 Final Budget, assessments by product and phase | Winding Cypress Community Development District | |
Ordinance 2015-48, creating the district | Collier County, via the district | |
Lake assessment, March 21, 2024 | Winding Cypress Community Development District | |
2025 audit, owners copy | Winding Cypress Homeowners Association | |
2025 reserve study update | Winding Cypress Homeowners Association | |
Estoppel certificate fee schedule | Florida Department of Business and Professional Regulation | |
FEMA LOMR-F 26-04-3737A, a 2026 single-lot letter | Federal Emergency Management Agency | |
Elevation Certificate, Live Oak Drive, 2015 | Collier County | |
2026 floodplain protection newsletter | Collier County | |
2026 Rate Kit, Collier County averages | Citizens Property Insurance Corporation | |
2050 Long Range Transportation Plan | Collier Metropolitan Planning Organization | |
2026 school grades data file | Florida Department of Education | |
Florida Statutes, including Chapter 720 | Florida Senate |
Market data from the Southwest Florida MLS, pulled 23 September 2026, and Collier County Property Appraiser records of qualified sales recorded through 19 June 2026. McGreevy and Comisar, 24031 S Tamiami Trl #101, Bonita Springs, FL 34134, (239) 898-6072. Brokered by Domain Realty.