Winding Cypress Homes for Sale in Naples, FL
Winding Cypress homes for sale are 766 homes in a gated DiVosta community east of Collier Boulevard in East Naples, ZIP 34114: built from 2015 to 2023, sold only as resales now, open to all ages under its recorded declaration, and carrying a community development district (CDD) on the tax bill. Collier County recorded 42 qualified sales in the 12 months to October 2, 2026, at an $825,000 median. Domain Realty Group, the #1 team in Southwest Florida since 2012, shows every Winding Cypress listing. Updated October 2026.
This page belongs to our Naples homes for sale and communities guide, beside the list of all Naples communities. Below you will find how to search Winding Cypress listings, what homes closed for on the county record, which DiVosta series and plats exist, what an owner pays each year to the association, the district and the tax collector, how rentals and sales work under the recorded rules, and the amenity, flood, school and distance facts that come with an address here. Winding Cypress is one association with one gate, so the sections split it by DiVosta series and by recorded plat, not by neighborhood. One name needs care: Verona Walk is the larger DiVosta community that shares the entry road off Collier Boulevard, but it has its own association, its own district and its own amenities, and none of its figures appear here as Winding Cypress figures.
By Jesse McGreevy and Marc Comisar, Domain Realty Group. Data updated: October 2026. Call Domain Realty Group at 239-441-2816.
Key takeaways for Winding Cypress buyers
Winding Cypress is a gated, resale-only community of 766 homes where the county's latest 12 months show 42 sales at an $825,000 median, a CDD that runs to 2045 and 2049, and no golf course inside the gate. These eight numbers frame a purchase here, from price and fees to rules and flood. Data updated: October 2026.
- Winding Cypress has 766 homes: 152 attached Villa Series homes, 406 Classic Series homes on 50 foot homesites and 208 Estate Series homes on 65 foot homesites, built by DiVosta Homes from a model park that opened on March 14, 2015 to a last builder deed on December 21, 2023.
- Collier County recorded 42 qualified sales in the 12 months to October 2, 2026, at an $825,000 median from $455,000 to $1,495,000, against 35 sales at $830,000 in the prior 12 months and 77 sales at $830,000 over 24 months.
- None of the 42 sales in the latest 12 months was a first sale from the builder, so all 42 were resales at the $825,000 median, which is what a sold-out community looks like on the record.
- The 2026 association budget sets annual dues at $6,247.75 for a Villa, $6,657.76 for a Classic and $7,067.22 for an Estate home, each including a $484 food and beverage minimum, billed in quarterly installments of $1,440.94, $1,543.44 and $1,645.80 plus the minimum in the first installment.
- The CDD assessment for fiscal year 2026/27 runs from $1,643.98 to $2,338.98 a year on the tax bill, with Series 2015 bonds maturing in November 2045 and Series 2019 bonds in November 2049, and $9,975,000 of par outstanding on January 1, 2026.
- The Declaration lets an owner lease for at least 30 days and no more than 1 year, up to 3 times in a calendar year, and gives the association no authority to disapprove a sale, with owner notice at least 20 days before closing.
- The amenity center lists 4 tennis courts, 8 pickleball courts and 4 bocce courts in its September 2026 rules, a resort pool, a spa, a fitness center and a cafe, and there are 0 golf holes inside the gate.
- FEMA's effective map of February 8, 2024 shows Zone AE at all 13 sampled addresses with a base flood elevation of 8.0 feet, the county places them in Evacuation Zone D, and the three zoned schools earned A, A and B for 2025-26.
Winding Cypress homes for sale right now
Winding Cypress homes for sale are linked below, filtered to the MLS subdivision name Winding Cypress so Verona Walk, Naples Reserve and other Collier Boulevard communities stay out. Every search sorts by price, high to low, and shows no listing count, because active inventory changes daily. Data updated: October 2026.
- All Winding Cypress homes for sale in Naples
- Winding Cypress homes for sale under $800,000
- Winding Cypress homes for sale over $800,000
- Winding Cypress homes built in 2019 or later
- Winding Cypress homes listed in the last 30 days
Listing data refreshes from the MLS throughout the day, and a listing shown may already be under contract. DiVosta has no homes left to sell here, so for builder-new homes elsewhere in the city see our Naples new construction guide, and for the larger DiVosta community next door see Verona Walk.
Search under and over $800,000
The two price searches split the community at $800,000, just below the county's 12-month median of $825,000. In the latest 12 months, 18 of 42 county sales, about 43 percent, closed under $800,000, and in the prior 12 months 17 of 35, about 49 percent, did. Use the first search for the lower half of the market and the second for the rest. The county record cannot say which series a sale belongs to, so the split describes price only. Both searches stay inside Winding Cypress.
Search by DiVosta series
No search key separates Villa, Classic and Estate homes, because the MLS has no field for the builder's series name. A listing's remarks may say villa or attached, and the lot width in the plat or the survey shows whether a detached home sits on a 50 foot or a 65 foot homesite. A Domain Realty Group agent can sort a day's listings by series for you.
What the MLS calls Winding Cypress
In the Southwest Florida MLS the community is the development Winding Cypress, and the searches above use that name. The county names its five recorded plats Winding Cypress Phase One, Phase 2, Phase 2C, Phase 2 Replat and Phase 3, so a tax record may read Phase 2 Replat while the marketing name is simply Winding Cypress. Some portals nest Naples Reserve under the Winding Cypress label, but Naples Reserve is a separate community with its own association, and a Naples Reserve listing is not a Winding Cypress listing. The ZIP code, 34114, is not a search filter because it also covers Naples Reserve, Hacienda Lakes and other communities.
Search three-bedroom, four-bedroom and pool homes
We do not link bedroom or pool searches because we have not confirmed the keys the search tool uses, and a wrong key would return nothing. DiVosta's captured pages show plans from 2 to 5 bedrooms and 2 to 4.5 baths across the community, so the all-homes search returns every bedroom count. DiVosta offered optional pools on detached lots in its 2015 marketing, and listing remarks say which homes have one.
Ready to tour Winding Cypress homes?
Tell us your price range, the series you prefer and whether you want the preserve or a lake behind the home, and a Domain Realty Group agent will arrange showings and pull the recorded sales for that part of the community. Contact Domain Realty Group, call 239-441-2816, or search all Southwest Florida listings. Domain Realty Group has been the #1 team in Southwest Florida since 2012.
What have Winding Cypress homes sold for?
Winding Cypress homes sold at a median of $825,000 on the Collier County record: 42 qualified sales in the 12 months to October 2, 2026, from $455,000 to $1,495,000. The count is even, so the median is the mean of the 21st and 22nd prices. Data updated: October 2026.
| Record and window | Sales | Median | Low | High |
|---|---|---|---|---|
| County, 12 months to Oct 2, 2026 | 42 | $825,000 | $455,000 | $1,495,000 |
| County, prior 12 months (Oct 2, 2024 to Oct 2, 2025) | 35 | $830,000 | $453,000 | $1,495,000 |
| County, 24 months to Oct 2, 2026 | 77 | $830,000 | $453,000 | $1,495,000 |
Sources: Collier County Property Appraiser public data bundle, qualified improved sales over $1,000, newest qualified Collier sale in the index dated October 2, 2026. The 12-month count is even, so its median is the mean of the middle pair of recorded prices; the prior-12-month and 24-month counts are odd, so each median is the middle price. Recorded sales reach the roll with a lag, and the newest Winding Cypress sale in the list is dated August 7, 2026.
Last 12 and 24 months
The 12-month median of $825,000 is $5,000, about 0.6 percent, below the prior 12 months' $830,000, while the number of sales rose from 35 to 42, an increase of 7 sales or 20 percent. The 42 sales equal about 5.5 percent of the community's 766 homes. The county's builder-direct test, a parcel's first recorded sale within one year of its year built, found 0 builder-direct sales in the latest 12 months, so all 42 were resales at the $825,000 median. The five highest sales in the window were $1,495,000 in Phase 2, $1,475,000 in Phase 3, $1,260,000 in Phase 3, $1,225,000 in Phase 2 and $1,150,000 in Phase 2 Replat, and the five lowest were $455,000, $460,000 and $470,000 in Phase 2, $520,000 in Phase One and $550,000 in Phase 2 Replat. The busiest month was March 2026 with 7 sales. The county does not record whether a sale was cash, whether a home has a pool or a lake view, or which DiVosta plan it is, so a median describes what closed and not what any one home is worth.
Price bands
In the latest 12 months, 12 of the 42 county sales closed under $600,000 and 8 closed at $1,000,000 or more, with the largest single band, 9 sales, from $800,000 to $899,999. In the prior 12 months the largest band was also $800,000 to $899,999, with 8 of 35. We tracked every one of the 77 recorded sales in the 24 months to count the bands below, which show the 12-month, prior-12-month and 24-month counts.
| County price band | Sales, 12 months | Sales, prior 12 months | Sales, 24 months |
|---|---|---|---|
| Under $600,000 | 12 | 4 | 16 |
| $600,000 to $699,999 | 4 | 7 | 11 |
| $700,000 to $799,999 | 2 | 6 | 8 |
| $800,000 to $899,999 | 9 | 8 | 17 |
| $900,000 to $999,999 | 7 | 6 | 13 |
| $1,000,000 to $1,199,999 | 4 | 1 | 5 |
| $1,200,000 and over | 4 | 3 | 7 |
| Total | 42 | 35 | 77 |
Source: Collier County Property Appraiser public data bundle, windows ending October 2, 2026, bands counted from the recorded sale list. The prior-12-month column covers October 2, 2024 to October 2, 2025. Each column adds to its window's sales. Band counts use recorded prices only and carry no square footage.
By plat
Winding Cypress has five recorded plats, and the sample on any one plat is small, so read plat medians as a description of what closed and not as a price for the plat. Phase 3 and Phase 2C had the highest 12-month medians, $890,000 on 11 sales and $875,000 on 3 sales, and Phase One the lowest, $599,900 on 9 sales; Phase 2 had 12 sales at $857,500 and Phase 2 Replat 7 sales at $620,000. Phase 2C had only 3 sales in 24 months, $645,000, $875,000 and $962,500, so treat its median as a description of three prices. We do not explain the gaps by lake views, lot size or plan, because the county record does not support any one reason.
| Plat (county name) | Sales, 12 months | 12-month median | Sales, 24 months | 24-month median |
|---|---|---|---|---|
| Winding Cypress Phase 1 | 9 | $599,900 | 18 | $695,000 |
| Winding Cypress Phase 2 | 12 | $857,500 | 22 | $872,500 |
| Winding Cypress Phase 2 Replat | 7 | $620,000 | 13 | $635,000 |
| Winding Cypress Phase 2C | 3 | $875,000 | 3 | $875,000 |
| Winding Cypress Phase 3 | 11 | $890,000 | 21 | $880,000 |
| All plats | 42 | $825,000 | 77 | $830,000 |
Source: Collier County Property Appraiser public data bundle, qualified improved sales, windows ending October 2, 2026. The 12-month rows add to 42 and the 24-month rows to 77. Even counts use the mean of the middle pair.
Newest recorded sales
The newest sales in the county list are August 7, 2026 at $815,000 in Phase 2, August 6 at $700,000 in Phase One, July 28 at $900,000 in Phase 2, July 13 at $565,000 in Phase 2 Replat and July 8 at $962,500 in Phase 2C. The list carries no addresses, owners or agents, and we do not print any. Ask a Domain Realty Group agent for the recorded sales on the street you are considering.
How have Winding Cypress prices moved since 2016?
Winding Cypress' annual median sale price rose from $500,500 in 2016 to a peak of $900,000 in 2023 on the Collier County record, about 80 percent, then eased to $867,500 in 2024 and $800,000 in 2025, and stands at $835,000 on 33 qualified sales in 2026 through October 2. Data updated: October 2026.
| Year | Sales | Median | Low | High |
|---|---|---|---|---|
| 2016 | 122 | $500,500 | $294,400 | $793,200 |
| 2017 | 120 | $505,200 | $296,000 | $770,800 |
| 2018 | 113 | $508,100 | $306,100 | $817,700 |
| 2019 | 117 | $513,700 | $307,000 | $924,200 |
| 2020 | 127 | $576,000 | $342,000 | $871,100 |
| 2021 | 142 | $629,550 | $335,000 | $1,195,000 |
| 2022 | 74 | $742,850 | $557,500 | $1,610,000 |
| 2023 | 45 | $900,000 | $545,000 | $1,895,000 |
| 2024 | 42 | $867,500 | $470,000 | $1,565,000 |
| 2025 | 39 | $800,000 | $453,000 | $1,495,000 |
| 2026 (to October 2) | 33 | $835,000 | $460,000 | $1,495,000 |
Source: Collier County Property Appraiser public data bundle, qualified improved sales by calendar year, 2026 through October 2. Every row is single-family coded and the county records no condominium sales here.
Builder years and resale years
The sales counts split into two eras. From 2016 through 2021 the county recorded 113 to 142 sales a year, 741 in all, a period that includes the builder's first sales, because DiVosta's last recorded deed to a buyer is dated December 21, 2023. From 2022 through October 2, 2026 the counts fell to 74, 45, 42, 39 and 33, 233 in all. DiVosta's own deed count for 2023 was 9, carried from earlier research, so at most 9 of the 45 county sales in 2023 were first sales from the builder. Annual medians in the early years therefore mix builder prices with resale prices, and the resale era begins to show clearly from 2023.
The 2023 peak and what followed
The 2023 median of $900,000 is the high for the table; 2025's $800,000 is 11.1 percent below it, and the 2026 figure of $835,000 is 7.2 percent below it. Median prices over 2016 to 2026 rose about 67 percent in all, from $500,500 to $835,000. The 2026 partial year has 33 sales through October 2, against 39 in all of 2025. Read the movement as direction and not as a forecast, because each year's mix of series and plats changes the median.
Which homes are in Winding Cypress?
Winding Cypress is 766 DiVosta homes in three series: 152 attached Villa Series homes, 406 Classic Series homes on 50 foot homesites and 208 Estate Series homes on 65 foot homesites, platted across five recorded plats from 2015 to 2018 and built from 2015 to 2023. DiVosta, a PulteGroup brand, was the only builder.
DiVosta, the builder
DiVosta Homes, L.P. bought the Winding Cypress land from Barron Collier entities in two takedowns in 2014 and 2015 and bought the Phase 3 land in 2018 from a Barron Collier-managed company. Trade press reported in May 2015 that DiVosta bought 849.79 acres for $15.36 million, and the recorded takedown deeds, carried from earlier research, show $5,025,000 on July 10, 2014 and $15,356,250 on April 30, 2015, with $11,395,500 for Phase 3 on June 22, 2018. DiVosta Homes is a brand of PulteGroup, which bought DiVosta in 1998. No other builder appears on any DiVosta capture, in the association's site or in press, and the last recorded builder-to-buyer deed is dated December 21, 2023, so every home for sale today is a resale.
The Villa, Classic and Estate series
The three series names appear in the district's lot table and the association's budget, and they set which assessment tier a home pays. The pre-launch brochure text, reproduced on an agent site we do not link, groups the plans this way: Serenity under the Villa Series; Abbeyville, Summerwood and Martin Ray under the Classic Series; Infinity, Pinnacle and Tangerly Oak under the Estate Series. We treat that grouping as supporting evidence only, and we say "listing materials group the plans as" when we use it.
| Series | What it is | Homes | Homesite |
|---|---|---|---|
| Villa Series | Attached villas | 152 | Villa lot (35 foot in the association budget) |
| Classic Series | Single-family | 406 | 50 foot |
| Estate Series | Single-family | 208 | 65 foot |
| Total | 766 |
Sources: Winding Cypress CDD Final Budget FY2026/27 lot table and the association's 2025 budget table; the association's 2026 budget table shows 206 Estate and 408 Classic homes, a two-home difference between two association documents that we note once and do not resolve. All three tables total 766.
The plans DiVosta listed
DiVosta's own pages, captured on the dates shown, list these plans with builder-stated living areas. A plus sign means the builder printed a base plan with options. These are builder sizes and not county records, and DiVosta printed its starting prices at the time, which are not sale prices.
| Plan | Series (listing materials group the plans as) | Beds | Baths | Builder living area | Capture |
|---|---|---|---|---|---|
| Serenity | Villa | 2 | 2 | 1,542 sq ft | July 21, 2019 |
| Cressida | not labelled in any capture | 2 to 3 | 2 | 1,579 sq ft | July 21, 2019 |
| Abbeyville | Classic | 2 to 3 | 2 | 1,671+ sq ft | July 21, 2019 |
| Summerwood | Classic | 2 to 5 | 2 to 3 | 1,861+ sq ft | July 21, 2019 |
| Martin Ray | Classic | 2 to 3 | 2 | 1,968+ sq ft | July 21, 2019 |
| Pinnacle | Estate | 3 to 4 | 3 to 4 | 2,488+ sq ft | August 12, 2020 |
| Tangerly Oak | Estate | 2 to 4 | 2.5 to 3 | 2,589+ sq ft | August 12, 2020 |
| Stonewater | Estate | 3 to 4 | 3 to 4.5 | 2,852+ sq ft | August 12, 2020 |
| Mystique | 2020 addition | up to 5 | up to 3 | 1,889 to 3,037 sq ft | December 3, 2020 release |
| Prestige | 2020 addition | 3 | 2 | more than 2,000 sq ft | December 3, 2020 release |
| Prosperity | 2020 addition | up to 3 | 2 | 1,670 to 1,790 sq ft | December 3, 2020 release |
| Palmary | 2020 addition | 2 to 3 | 2 | 1,943 to 2,063 sq ft | December 3, 2020 release |
Sources: DiVosta Winding Cypress page captures dated July 21, 2019 and August 12, 2020 and a trade release dated December 3, 2020. Infinity, the Estate plan sold at launch, appears on the March 13, 2015 capture at 2,385+ square feet with 3 bedrooms and 3 baths and was gone from the lineup by 2020. The 2019 trade release puts the builder's range at 1,542 to more than 2,852 square feet, and the 2020 release at 1,670 to more than 3,800 square feet, two to five bedrooms and two to four and a half baths.
How the lineup changed
At launch in 2015 the page listed seven plans. By August 12, 2020 DiVosta listed six designs: Abbeyville, Summerwood, Martin Ray, Tangerly Oak, Pinnacle and Stonewater. Four plans, Mystique, Prestige, Prosperity and Palmary, were added in December 2020 for the final phase, with the release placing prices in the $400s to $700s. DiVosta's starting prices at the time moved from $263,990 for Serenity on December 15, 2014 to $312,990 on July 21, 2019, and from $378,990 for Abbeyville in 2019 to $386,990 in 2020. Those are builder starting prices for a base plan and are never comparable with resale prices on the same line.
What we could not confirm about the series
No first-party plat-by-series table exists, so we cannot say which plat holds the 152 villas, and the county codes villas and detached homes alike as single-family, so the county medians cannot separate them. Whether Cressida is a Villa Series plan is also not stated in any capture. The Tifton plan that one agent site lists is a Verona Walk plan name and never appears on a DiVosta Winding Cypress capture, so it does not belong on this list.
The five recorded plats
All five plats are one association with one gate, so none is a separate neighborhood. The county plat names matter because they appear in recorded sales and tax records.
| Plat | Recorded | Residential lots on the county roll | What it holds |
|---|---|---|---|
| Winding Cypress Phase One | January 27, 2015 | 153 | First lots, the amenity center tract and entry features |
| Winding Cypress Phase 2C | January 11, 2016 | 23 | A small carve-out of Phase 2 |
| Winding Cypress Phase 2 | March 14, 2016 | 245 | Main Phase 2 lots |
| Winding Cypress Phase 2 Replat | March 28, 2017 | 143 | Replat of Phase 2 lots and parts of four tracts |
| Winding Cypress Phase 3 | November 15, 2018 | 202 | The final phase |
| Total | 766 | 153 + 23 + 245 + 143 + 202 |
Sources: plat index entries carried from earlier research and the county parcel roster in Agent C. The roster counts 828 parcels in all, because lakes, common areas and rights-of-way carry parcel numbers, and 766 of them are single-family coded. Phase 3 matters to a buyer because its district debt assessment is higher, as the cost section shows.
Preserve, lakes and acreage
The association's site describes over 800 acres of natural preserves and 80 acres of lakes, next to Picayune Strand State Forest, and DiVosta's 2015 page used the same two figures. Earlier county parcel work carried about 818 acres of recorded preserve tracts and 29 stormwater lakes, and the district's 2015 engineer's plan counts about 83.4 acres of permitted lakes. A South Florida Water Management District conservation easement recorded July 10, 2014 allows passive recreation only. The Winding Cypress planned unit development covers a larger area that includes Verona Walk, so its 1,928 acres and 2,854 approved units are not this community's figures, and we do not use them.
Construction features
DiVosta's brochure, carried from earlier research, lists steel-reinforced concrete block construction, engineered roof trusses with hurricane tie-downs and galvanized steel hurricane shutters as standard, with impact glass optional. Which opening protection a resale home has, and its roof material, are not published for the community, so ask the seller for the wind mitigation report and the option sheet before relying on either.
The builder warranty that may remain
The PulteGroup (DiVosta) Home Protection Plan book lists one year for materials and workmanship, two years for heating, air conditioning, electrical and plumbing, five years for certain water infiltration and leaks, and ten years for structural elements, all from closing, and its terms are transferable only to a subsequent owner who takes title within the warranty period and uses the home as a residence. The ten-year structural term has already ended for the earliest homes, which closed in 2015, and runs to about 2033 for the last, closed December 21, 2023. Each home's clock starts on its own closing date, the book's edition tied to a given purchase agreement may differ, and the book provides for binding arbitration. Florida section 95.11 also sets limits on construction claims, so ask a Florida attorney how it applies to a specific home. Ask the seller for the closing date and the warranty book.
What does it cost to own a Winding Cypress home?
Winding Cypress owners pay four recurring charges: association dues of $6,247.75 to $7,067.22 a year in 2026, a district assessment of $1,643.98 to $2,338.98 on the property tax bill, a $261.91 solid waste assessment from a 2025 bill, and county property tax at a 2025 rate of 10.5058 mills. Data updated: October 2026.
2026 HOA dues by series
The Winding Cypress Homeowners Association approved its 2026 budget on November 18, 2025, requiring $4,751,946 from owners, down $47,573 from $4,799,519 in 2025. The budget has one association for all three series, with a maintenance line that varies by lot frontage.
| Line, per home per year | Estate (65 ft) | Classic (50 ft) | Villa |
|---|---|---|---|
| Maintenance (by lot front footage) | $1,775.33 | $1,365.87 | $955.86 |
| Common Area Charge | $873.89 | $873.89 | $873.89 |
| HOA Operating Costs | $3,103.79 | $3,103.79 | $3,103.79 |
| Shady Palm Assessment | $223.89 | $223.89 | $223.89 |
| Reserves | $606.32 | $606.32 | $606.32 |
| Total annual before the minimum | $6,583.22 | $6,173.76 | $5,763.75 |
| Food and beverage minimum | $484.00 | $484.00 | $484.00 |
| Total annual cost | $7,067.22 | $6,657.76 | $6,247.75 |
| Quarterly installment | $1,645.80 | $1,543.44 | $1,440.94 |
Source: Winding Cypress HOA 2026 Approved Budget, final October 29, 2025. The quarterly installment is the annual total before the minimum divided by four, about 1.0 percent below the 2025 installments of $1,662.31, $1,558.89 and $1,455.33. The minimum itself rose from $440 in 2025 to $484 in 2026. The Declaration bills the minimum in full with the first installment, so added up from the budget's own lines the first-quarter bill is $2,129.80 for an Estate, $2,027.44 for a Classic and $1,924.94 for a Villa; confirm billing dates with the office.
What the budget pays for
The largest budget line is the landscape contract at $1,673,505. Gate access control is budgeted at $220,000, management at $104,000, on-site wages at $538,000, property insurance at $130,000 and a contingency at $300,000. Reserve revenue is $464,441 for 2026, and the pooled replacement fund held $874,236 on December 31, 2025, with an independent reserve study dated January 2025. The Shady Palm Cafe is budgeted at a net loss of $171,500, funded through the $223.89 Shady Palm Assessment. The 2025 audit shows $19,424 of assessments receivable at year-end, against $11,634 a year earlier. No golf membership or equity membership appears in the dues, and no bulk cable or internet contract appears in the budget lines; whether one exists outside the budget is unverified, so ask for the estoppel package.
The food and beverage minimum
The recorded Declaration set the minimum at $600 per fiscal year effective 2022 but lets the Board raise or lower it, never more than 10 percent over the prior year, and the 2026 budget charges $484. It must be used by year end with no refund or carry-over, and the 2025 audit recognized $23,343 of unused minimums as revenue. The minimum is credit toward purchases at the Shady Palm Cafe, so a buyer who does not use the cafe still pays it. Because the minimum is spendable at the cafe, dues net of that credit would be $484, about $40.33 a month, lower.
The community development district
The Winding Cypress Community Development District was established by Collier County Ordinance 2015-48 on September 10, 2015 under Chapter 190 of the Florida Statutes. It finances and maintains roads, stormwater and lakes through two bond issues, and its assessments appear as one line in the non-ad valorem section of the Collier tax bill. Fiscal year 2026/27 runs from October 1, 2026 to September 30, 2027, and the assessment has been unchanged for three years.
| Lot type | Units | Operations | Debt | Total FY2026/27 |
|---|---|---|---|---|
| Phases 1 and 2 Villa | 152 | $794.98 | $849.00 | $1,643.98 |
| Phases 1 and 2, 50 ft | 270 | $794.98 | $954.00 | $1,748.98 |
| Phases 1 and 2, 65 ft | 132 | $794.98 | $1,060.00 | $1,854.98 |
| Phase 3, 50 ft | 136 | $794.98 | $1,429.00 | $2,223.98 |
| Phase 3, 65 ft | 76 | $794.98 | $1,544.00 | $2,338.98 |
Source: Winding Cypress CDD Final Budget FY2026/27. Amounts include a 4 percent early-payment discount, a 2 percent Tax Collector fee and a 1.5 percent Property Appraiser fee. Phases 1 and 2 hold 554 units and Phase 3 holds 212, 766 in all; the 50 foot lots total 406 and the 65 foot lots total 208.
The district's bonds and budget
| Series | Original par | Rate | Issued | Maturity | Par on Jan 1, 2026 |
|---|---|---|---|---|---|
| 2015 | $7,535,000 | 4.00% to 5.00% | December 2015 | November 2045 | $6,035,000 |
| 2019 | $4,470,000 | 3.75% to 5.00% | February 2019 | November 2049 | $3,940,000 |
Outstanding par on January 1, 2026 was $6,035,000 plus $3,940,000, or $9,975,000. Principal is due November 1 and interest on May 1 and November 1. The fiscal year 2026/27 budget shows revenues of $1,461,997 and operations spending of $618,260, of which $300,000 is a lake bank remediation line and $50,000 is lake bank maintenance, with a lake bank reserve of $366,062 on July 1, 2026. Operations assessments rose from $232.06 in fiscal year 2022/23 to $794.99 in 2023/24, carried from earlier research. A buyer can request a payoff or assessment statement through the district manager's request form.
Association dues plus district assessment plus solid waste
Adding the 2026 association dues to the fiscal year 2026/27 district assessment, and then the $261.91 solid waste assessment printed on a 2025 tax bill (carried), gives the fixed annual charges before property tax and insurance.
| Series and phase | HOA 2026 (with $484 minimum) | CDD FY2026/27 | HOA plus CDD | Plus $261.91 solid waste |
|---|---|---|---|---|
| Villa, Phases 1 and 2 | $6,247.75 | $1,643.98 | $7,891.73 | $8,153.64 |
| Classic 50 ft, Phases 1 and 2 | $6,657.76 | $1,748.98 | $8,406.74 | $8,668.65 |
| Classic 50 ft, Phase 3 | $6,657.76 | $2,223.98 | $8,881.74 | $9,143.65 |
| Estate 65 ft, Phases 1 and 2 | $7,067.22 | $1,854.98 | $8,922.20 | $9,184.11 |
| Estate 65 ft, Phase 3 | $7,067.22 | $2,338.98 | $9,406.20 | $9,668.11 |
Divided by 12, the association plus district charges run $657.64 a month for a Villa, $700.56 to $740.15 for a Classic and $743.52 to $783.85 for an Estate. Do not add property tax or insurance to these figures; they come next.
Property taxes
Winding Cypress is in unincorporated Collier County, so there is no city levy. The 2025 total millage on a Winding Cypress tax bill was 10.5058 mills, as the components below sum. The county, school and fire components were checked against published budgets, and the water management, basin and mosquito control lines rest on an earlier read of a 2025 bill, so they are marked carried.
| Levy (2025) | Mills | Status |
|---|---|---|
| Collier County General Fund | 3.0107 | Verified, county adopted budget |
| Unincorporated Area General Fund | 0.6844 | Verified, county adopted budget |
| Conservation Collier | 0.2096 | Verified, county adopted budget |
| Water Pollution Control | 0.0246 | Verified, county adopted budget |
| School Board, required local effort | 2.0010 | Verified, district budget |
| School Board, local levies | 2.2480 | Verified, district budget |
| Fire district levy | 2.0000 | Supporting, district budget book |
| South Florida Water Management District | 0.0948 | Carried |
| Big Cypress Basin | 0.0978 | Carried |
| Collier Mosquito Control | 0.1349 | Carried |
| Total | 10.5058 | Sum of the ten lines |
The county lines add to 3.9293 mills, the school lines to 4.2490, the fire levy is 2.0000 and the three carried lines add to 0.3275. We print no worked tax bill here, because ad valorem tax depends on a parcel's taxable value, exemptions and any cap, and the property appraiser's value cannot stand in for a price. Read the parcel's own bill. The 2026 bills arrive in November 2026 and carry the final 2026 rates and the district's 2026 assessment.
Capital contribution and the estoppel certificate
The 2025 audit lists a resale capital contribution of $1,050, raised from $1,000 in March 2023, paid by the buyer at closing under Declaration section 4.7, which lets the Board set it each year with increases capped at 10 percent. The 2026 amount is not published, so confirm it on the estoppel certificate. Florida section 720.30851 requires the association to deliver an estoppel certificate within 10 business days of a written request, effective for 30 days if delivered by hand or email and 35 days if mailed, and the state's current caps are $299 for preparation and delivery plus $119 if expedited, per the Department of Business and Professional Regulation fee sheet read October 29, 2026. The Declaration repeats the 10 business day rule.
The CDD at resale
A resale contract is not an initial sale, so the statutory contract legend in Florida section 190.048 for initial sales does not apply to a Winding Cypress resale. The district assessment still appears on the tax bill, and the recorded Declaration repeats the district disclosure in section 3.6. Ask the seller or the district for the current assessment statement before you remove contingencies, and ask whether the home's debt is the Series 2015 or Series 2019 tier.
Documents to request
Ask for the estoppel certificate, the current budget, the recorded Declaration and Rules and Regulations, the latest audit, the district's current assessment statement, the sale notice form, the seller's flood disclosure and any FEMA letter for the lot, the wind mitigation report, the roof permit history and the warranty book with the closing date. The association's public documents page also hosts a sales and leasing application, whose fee schedule is not in the Declaration and whose amount we did not find published.
What is in the Winding Cypress amenity center?
The Winding Cypress amenity center at 7180 Winding Cypress Drive holds a heated resort pool and spa, a fitness center with a Movement Room, a community event room, an internet cafe, a library, a catering kitchen, locker rooms and the Shady Palm Cafe, with 4 tennis, 8 pickleball and 4 bocce courts outside. Counts below follow the September 2026 rules.
Courts and sport
The September 2026 Rules and Regulations list 4 tennis courts, 8 pickleball courts and 4 bocce courts. An older association amenities page still describes five clay tennis courts and four pickleball courts, which matches the news of a 2026 conversion of tennis space to pickleball, so we use the rules count and name its date. Court hours in the rules are 7 am to 10 pm. Tennis reservations run through the Activities Director, with a limit of 2 hours a day and 8 hours a week per homeowner, and pickleball open play runs from 7 am to noon daily on courts 1 to 4. Bocce courts are lighted. A county Hearing Examiner notice for a pickleball fence petition, hearing date March 13, 2026, exists, and its outcome is not confirmed here.
Pool, spa and fitness
The pool is a heated resort pool with a waterfall feature and two designated swim lanes, a maximum load of 131, hours from dawn to dusk with no night swimming, and no lifeguard on the premises. The spa runs about 104 degrees Fahrenheit with a maximum load of 7, a minimum age of 16 and a 15 minute limit per use. The fitness center has cardio, strength and free weights, a Movement Room with mirrors and balls, and men's and women's locker rooms, with a minimum age of 13 for the fitness center. The rules say 24 hours for the fitness center, while an older page says 5 am to midnight, so confirm the current schedule with the association.
Rooms, cafe and fire pit
The event room holds 136 people and the internet cafe 64, both with televisions and audio, and owners may reserve them for community gatherings. The library is open 24 hours, the catering kitchen can be reserved, and complimentary Wi-Fi covers the amenity center. A fire pit area is first come, first served with no glass. The Shady Palm Cafe is the poolside bar and restaurant, run on an owner membership account and tab, and it is not available for private-event catering. We publish no operator, hours or prices for it, since the association posts them behind a resident login. The sources conflict on the clubhouse's size, 17,500 square feet in DiVosta marketing and 22,000 in a contractor's portfolio, so we print no square footage.
Trails, dog parks and clubs
A wooden boardwalk crosses preserve to a sheltered overlook and closes at sunset, and the rules bar entry to the preserve itself. Two dog parks serve small and large pets, and the Garden Club keeps individual plots. The association's clubs page lists groups for pickleball, tennis, bocce, Corvette, book, garden, crafts, water aerobics, and cards and games. Longer hikes are in Picayune Strand State Forest, which adjoins the community on the east and south and is reached by road. Florida Forest Service lists the Sabal Palm Hiking Trail at 3.2 miles, and the trailheads are outside the gate.
Who may use the amenities
The rules say use of Winding Cypress is exclusive to owners and tenants, their resident family and escorted guests. Each home receives 2 key fobs, extra fobs cost $25 each for owners and up to 3 may be distributed, and lending a fob can cost amenity privileges. Verona Walk residents have no stated right to use them, even though the two communities share an entry road. Drones are prohibited except licensed commercial use, and golf carts are allowed with insurance and association registration.
Is there golf in Winding Cypress?
Winding Cypress has no golf course. Neither the association's amenity list, the rules nor DiVosta's original feature list includes golf, no golf or equity membership appears in the dues, and golf carts are allowed only for travel inside the community. The nearest public golf is Lely Resort, with Mustang and Flamingo Island courses, and Hibiscus Golf Club.
Public golf nearby
Lely Resort Golf and Country Club's Mustang and Flamingo Island courses both advertise public tee times online, and Hibiscus Golf Club describes itself as one of the few full-service public golf facilities in Collier County. We have not verified drive times from the gate to either, so we give none. For the Lely Resort community itself, see our Lely Resort page, and for golf settings across the city see Naples golf homes for sale.
No lake use
The community's lakes are stormwater lakes controlled by the district, and the rules state residents have no recreational access to them, including fishing and water toys. The community has no boat ramp or marina. Public paddling access is at Collier County parks, such as Sugden Regional Park.
Is Winding Cypress gated?
Winding Cypress is gated, with an entry gate and guard house that DiVosta described in 2015 and gate access control budgeted at $220,000 in 2026. The recorded Declaration says the association is not an insurer of security, and gate staffing hours are not published, so ask the association for current gate procedures.
How the gate works
The association's site calls Winding Cypress a master-planned, gated community. Amenity doors use key fobs, guests must be accompanied, and the Declaration lets the association deactivate an owner's gate transponder and require entry through a guest entrance. The amenity campus carries video surveillance, per the rules. The Declaration, section 6.1, states that the association makes no representation about security, so we do not describe the gate as secure or staffed around the clock, and we say only that it is gated.
Visitors and agents
The association hosts a visitors and agents page that lists the sales and leasing application and the rules. Showings and guest access follow the association's current procedure, which is not stated on its public pages, so a Domain Realty Group agent confirms it before a tour.
Is Winding Cypress a 55+ community?
Winding Cypress is not a 55+ community. The recorded Amended and Restated Declaration contains no age restriction, and a document-wide search for age, 55, adult, senior and housing for older persons returned no result. The association's rules set only a minimum age for the fitness center, 13, and the spa, 16.
What the Declaration says
Section 1.7 defines Family without any age term. The Declaration was recorded in 2024 as an amended and restated instrument, and the hosted copy is dated February 5, 2024. For 55+ communities elsewhere in the city see Naples 55+ communities.
What are the rental rules in Winding Cypress?
Winding Cypress allows leases of at least 30 continuous days and no more than 1 year, and a home may be leased no more than 3 times in a calendar year. The Board must approve each lease, applications go in at least 20 days before first occupancy, and rentals of less than 30 days are a prohibited use.
Lease terms
Declaration section 12.4 limits leasing to the entire unit, with a 30 day minimum and a 1 year maximum, no more than three leases in a calendar year and no timeshare. A new lease cannot start until 30 days after the first day of the prior lease. The Board may disapprove a lease only by a majority of the whole Board and only for good cause, such as screening results, financial responsibility, delinquency or uncorrected violations. The Declaration lets the association charge a transfer fee for each lease application, and the amount is not published.
What rentals look like
Rentals do appear in every size. Portal snapshots seen on October 29, 2026 showed asking rents, mixing furnished and unfurnished and seasonal and annual terms, so we publish no dollar range and no rent. A dated range needs a Matrix lease pull, which is owed. An investor reading the rules should note that the three-lease cap allows seasonal tenancies of 30 to 90 days only a limited number of times a year.
Can the HOA block a sale in Winding Cypress?
The Winding Cypress association cannot block a sale. Declaration section 12.3 says the association has no authority to disapprove a proposed conveyance. The owner gives written notice at least 20 days before closing with the purchase contract, and the Board issues a Certificate of Approval within 20 days or approval is deemed given.
Notice, certificate and timing
The owner must give the buyer the governing documents before transfer. The Board may ask for more information, and a transfer fee may be charged, with the amount not published. Because the 20-day notice window can be longer than a quick closing, notice should go in the day the contract is signed, and the estoppel certificate, due within 10 business days of the request, should be ordered at the same time. A lease, unlike a sale, can be refused for good cause.
Resale buyer's order of steps
Contract signed; owner's notice with the contract to the association; estoppel ordered; Certificate of Approval within 20 days or deemed; capital contribution and prorated dues at closing. The Declaration does not contain a right of first refusal, and a search for one returned nothing.
What other rules apply in Winding Cypress?
Winding Cypress homes are governed by a recorded Declaration, September 2026 Rules and Regulations and an architectural review process. Owners may keep up to 3 pets, park cars on driveways, keep trailers, boats and commercial vehicles in a garage, and submit exterior changes for a 60-day review.
Pets
The Declaration allows no more than 3 pets, excluding tropical fish, and prohibits pit bulls, wolf hybrids and dogs prone to aggression. The rules require a handheld, non-retractable leash no longer than six feet, and pets are not allowed inside the amenity center.
Vehicles and golf carts
Cars, vans, pick-ups and SUVs used for primary passenger transport may park on driveways overnight. Commercial vehicles, RVs, boats, trailers, motorcycles, golf carts and vehicles with commercial markings must be kept in an enclosed garage, and no one may park overnight in roadways or common areas. Golf carts need a licensed driver, may not leave the community and need liability insurance naming the association, per the Declaration as carried from earlier research.
Exterior changes
An owner submits one complete set of plans, permits and material samples to the Architectural Reviewer, who has 60 days after a complete submission, and silence is deemed approval. Decisions are in writing and a deposit of up to $5,000 may be required. A September 2025 amendment, carried from earlier research, lets temporary storm shutters stay up no more than 72 hours before a storm and come down within 72 hours after.
Signs, assessments and liens
No sign of any kind, including a real estate sign, may be displayed without Board consent or as the rules allow. The Board may levy special assessments without a member vote for legal compliance and necessary maintenance, repair, insurance or replacement of common area, and other special assessments need two thirds of voting interests. Assessments are secured by a continuing lien, and parcels without a certificate of occupancy pay 5 percent of regular assessments.
Management and governance
Winding Cypress Homeowners Association, Inc. is a Florida not-for-profit corporation, per state records as carried in our research, and Seacrest Southwest Property Management of Naples manages it, with an on-site general manager, assistant manager, activities director and maintenance supervisor. The office at 7180 Winding Cypress Drive is open Monday to Friday, 8 am to 4 pm, closed 11:30 am to 12:30 pm, as of October 29, 2026. The 2025 audit mentions pre-suit mediation with claimants about pickleball courts, and the association reports that management believes no other claims materially affect it; ask for the board minutes and the estoppel package.
Winding Cypress vs Verona Walk: how do they differ?
Winding Cypress and Verona Walk share a builder, DiVosta, a planned unit development and an entry road off Collier Boulevard, but they have separate associations, separate districts and separate amenities. Winding Cypress has 766 homes and an $825,000 county median, and Verona Walk has 1,920 homes and a $495,000 median. Data updated: October 2026.
| Yardstick | Winding Cypress | Verona Walk |
|---|---|---|
| Homes | 766 (152 villas, 406 Classic, 208 Estate) | 1,920 per its association |
| Builder and years | DiVosta; model park March 14, 2015; last builder deed December 21, 2023 | DiVosta; built from about 2004 |
| County sales, 12 months to Oct 2, 2026 | 42 sales, $825,000 median, $455,000 to $1,495,000 | 89 sales, $495,000 median, $400,000 to $1,030,000 |
| County sales, 24 months | 77 sales, $830,000 median | 179 sales, $520,000 median |
| Association dues | $6,247.75 to $7,067.22 a year in 2026 | Not published |
| District | Winding Cypress CDD, $1,643.98 to $2,338.98 in FY2026/27 | Verona Walk CDD, $744.85 to $992.85 per lot in FY2026/27 |
| Amenities | Amenity center with resort pool, 4 tennis, 8 pickleball, 4 bocce, cafe | Town Center with two pools, 6 pickleball courts, tennis, bocce and shops |
| Lease rules | At least 30 days, at most 1 year, 3 leases a year | At least 4 months, no yearly cap found |
| Gate | Gated; staffing hours not published | Gate manned 24 hours per its association |
Sources: Collier County Property Appraiser public data bundle for both communities, windows ending October 2, 2026; each community's association, district and Declaration documents. County counts are single-family coded recorded sales. The Verona Walk dues are not published by its association.
What they share
DiVosta built both inside the same planned unit development. Winding Cypress was sold from the Verona Walk sales center from December 2014 until its own sales center opened. A recorded 2014 cost-sharing agreement governs the entry road from Collier Boulevard, and per the recorded Declaration the Verona Walk association pays 31 percent of shared costs while the Winding Cypress association operates and insures the shared facilities. The amenities are not shared.
What differs
Winding Cypress homes are 2015 to 2023 construction, while Verona Walk homes are about 2004 onward. Each community pays its own association and its own district, so fees do not compare. Verona Walk offers townhomes that Winding Cypress does not, and has a Town Center, while Winding Cypress has 152 attached villas and one amenity center. For the full Verona Walk picture, see our Verona Walk page.
Which buyers choose which
In product terms, a buyer who wants a larger community, a lower recorded median, a mix of attached and detached homes, longer minimum leases and a published district schedule looks at Verona Walk. A buyer who wants a smaller community, homes built from 2015 to 2023, a single amenity center with 8 pickleball courts and a cafe, shorter permitted leases with a yearly cap and a higher recorded price range looks at Winding Cypress.
How does Winding Cypress compare with other East Naples communities?
Winding Cypress' 42 recorded sales at an $825,000 median sit between Verona Walk's $495,000 and Naples Reserve's $886,000 in the county record for the 12 months to October 2, 2026. The table compares eight Naples communities on one yardstick, county recorded sales. Data updated: October 2026.
| Community | Sales, 12 months | Median, 12 months | Sales, 24 months | Median, 24 months |
|---|---|---|---|---|
| Winding Cypress | 42 | $825,000 | 77 | $830,000 |
| Verona Walk | 89 | $495,000 | 179 | $520,000 |
| Island Walk | 105 | $520,000 | 174 | $550,500 |
| Naples Reserve | 29 | $886,000 | 69 | $800,000 |
| Esplanade by the Islands | 158 | $855,000 | 404 | $1,009,400 |
| Esplanade at Hacienda Lakes | 18 | $578,500 | 39 | $730,000 |
| Treviso Bay | 80 | $562,000 | 141 | $587,500 |
| Fiddler's Creek | 170 | $765,000 | 272 | $902,500 |
| Valencia Sky | 144 | $853,850 | 144 | $853,850 |
Source: Collier County Property Appraiser public data bundle, qualified improved sales, windows ending October 2, 2026, labelled county recorded sales and not MLS. Medians for Verona Walk, Naples Reserve and Esplanade at Hacienda Lakes use the community's own subdivision names; Fiddler's Creek and Esplanade by the Islands count every recorded plat and condominium inside each community, so both mix single-family and condominium sales; Treviso Bay combines its single-family and condominium plats, 14 single-family sales at $1,815,000 and 66 condominium sales at $521,000; Valencia Sky's count includes closings from a builder still selling, so its 24-month figure equals its 12-month figure.
How to read the table
The communities differ in product, age and fees, so a median compares a mix of homes and not like for like. Winding Cypress sits at the upper middle of the group on recorded price: above Verona Walk, Island Walk, Treviso Bay, Esplanade at Hacienda Lakes and Fiddler's Creek, and below Valencia Sky, Naples Reserve and Esplanade by the Islands. Sample sizes of 18 to 144 sales mean any one median can move with a handful of closings. See our pages for Island Walk, Naples Reserve, Treviso Bay and Fiddler's Creek for each community's own record, and our Naples communities list for the rest.
Naples Reserve and Winding Cypress
Naples Reserve is a separate community with its own association. Its county parcels total 704, of which 609 are single-family, and its 12-month median of $886,000 on 29 sales is $61,000 above Winding Cypress' median. Portal labels sometimes nest Naples Reserve under Winding Cypress, which is a naming trap and not a membership.
Nearby new construction, dated
Builder starting prices read on October 29, 2026 show what a buyer weighs against resale: Taylor Morrison's Esplanade by the Islands from $599,999, Toll Brothers' Seven Shores from $599,995, GL Homes' Valencia Sky, a 55+ community, from the $780s, and DiVosta's Terreno at Valencia from $400,990 to $985,990. These are builder bases that exclude homesite premiums and district assessments, and they change weekly. For the full builder comparison see our Naples new construction guide, and for the GL Homes 55+ alternative on Immokalee Road see Valencia Trails.
Is Winding Cypress in a flood zone?
Winding Cypress is mapped Zone AE on FEMA's effective flood map, effective February 8, 2024, with a base flood elevation of 8.0 feet in the screening of 13 sampled addresses, and the county places the community in Evacuation Zone D. Individual homes may hold FEMA letters that move them to shaded Zone X, so check the specific lot. Data updated: October 2026.
Zone AE and the base flood elevation
Our screening results, carried from September 2026 research, found Zone AE at all 13 sampled addresses on panels 12021C0604J, 0608J, 0612J and 0616J, with base flood elevation lines of 8.0 feet at most points, 7.5 feet at two lines and static elevations of 7.0 feet at two spots on Jacaranda Lane and Arrowhead Way, all in NAVD88. The 2012 map already showed AE here. The statements "Winding Cypress is not in a flood zone" and "no Winding Cypress home can be removed from the zone" are both false: the community is mapped AE, and lots have separate FEMA letters. Lenders use the effective map, and FEMA says lenders keep the right to require flood insurance beyond the federal mandate.
Elevation certificates
Collier County publishes elevation certificates, and earlier research counted 230 on Winding Cypress streets from permits between 2014 and 2019. Two certificates read in full show the top of the bottom floor at 10.10 feet for a Phase One home certified June 8, 2015 and 9.40 feet for a Phase 3 home certified July 9, 2019, about 1.4 to 2.1 feet above the 8.0 foot elevation. Those are two homes and not the community. Ask the seller for the home's own certificate, since an elevation certificate can lower a flood insurance rate.
LOMR-F letters
A letter of map revision based on fill (LOMR-F) is a FEMA letter that removes a lot or structure from the high-risk zone on survey elevation. Earlier research found 25 FEMA case records naming Winding Cypress: 9 phase-wide letters from 2015 to 2019, made under the 2012 map and now shown as superseded or not incorporated under the 2024 map, and 16 single-lot letters since the 2024 map, covering 15 homes, mostly on Live Oak Drive in Phase One and on Cocoplum Street in Phase 3. These are carried and not reread this week. The letters say the lender "has the option to continue the flood insurance requirement," so a letter lifts the federal mandate and not necessarily the lender's rule. Ask the seller whether the home has a FEMA letter.
The preliminary map
Collier County's preliminary Flood Insurance Rate Map was released March 20, 2025, a community open house was held June 17, 2025 and a 90-day appeal and comment period began August 19, 2026, which by simple arithmetic runs to about November 17, 2026. The county lists summer 2027 as the target date for the new map, subject to change. Until then the effective map of February 8, 2024 governs. We could not read which zone the preliminary map shows for Winding Cypress, so we do not predict one; you can view it at FEMA's Map Service Center preliminary viewer.
Evacuation zone
County records carried from September 2026 place Winding Cypress in Evacuation Zone D at all 13 sampled addresses, with Zone C starting about 1 kilometer west near Collier Boulevard. Hurricane Ian's mandatory order covered Zone A and Hurricane Milton's covered Zones A and B. Confirm any address on the county's lookup and the state's Collier map before storm season.
Storms on record
Hurricane Ian's worst surge flooding in Collier County was south and west of US 41, according to the National Weather Service, and Winding Cypress lies north-east of US 41 and east of Collier Boulevard. The only Winding Cypress statement on record is a district board minute carried from earlier research: "No significant damage was noted by the community." We have not confirmed the meeting date, and absence of a damage report is not proof that no home flooded. Ask the seller the three questions in the Florida seller flood disclosure.
Insurance, roofs and the 15-year rule
Section 627.7011 bars an insurer from refusing or non-renewing a policy solely because a roof is under 15 years old, and at 15 years or more it requires the insurer to let the homeowner have a roof inspection before requiring replacement. The first original roofs reach 15 years about 2030. Citizens requires a four-point inspection only for homes more than 20 years old, so the earliest Winding Cypress homes reach that mark in 2035, and Citizens' eligibility is decided at quote time. FEMA's Risk Rating 2.0 sets National Flood Insurance Program premiums from the building's characteristics, with annual increases capped at 18 percent, and a flood policy normally has a 30-day waiting period unless a lender requires it. We publish no premium, because no first-party figure exists for this community. Ask for the wind mitigation report, form OIR-B1-1802, valid for five years.
Seller flood disclosure and wildfire
Florida section 689.302 requires a seller to give a flood disclosure at or before the contract: knowledge of flooding that damaged the property, flood insurance claims including National Flood Insurance Program claims, and assistance received including FEMA. Picayune Strand State Forest adjoins the community, and the USDA Forest Service rates Collier County's wildfire risk as very high, so smoke from prescribed burns and wildfires belongs on a buyer's list beside hurricanes. A 2026 wildfire in the forest did not name Winding Cypress.
Which schools serve Winding Cypress?
Winding Cypress is zoned to Lely Elementary School, Manatee Middle School and Lely High School for the 2026-27 school year, per the district address lookup as carried in October 2026. For 2025-26 the state grades are an A for Lely Elementary, an A for Manatee Middle and a B for Lely High. Confirm with the district.
| School | Grades served | State grade 2025-26 | Grade 2024-25 | Enrollment 2024-25 |
|---|---|---|---|---|
| Lely Elementary School | PK to 5 | A | A | 499 |
| Manatee Middle School | 6 to 8 | A | A | 781 |
| Lely High School | 9 to 12 | B | A | 1,475 |
Sources: Collier County Public Schools 2025-2026 School and District Grades, dated July 1, 2026, carried from earlier research; enrollment from the National Center for Education Statistics for 2024-25. Lely High is about 3.7 road miles and 11 minutes from the community's entry road, free flow. Collier County Public Schools earned an A for the ninth year.
Choice enrollment
The district runs Controlled Open Enrollment under Board Policy 5120, with Out-of-Zone and School Choice tracks. The 2026-27 windows were closed when the page was read in August 2026, and the district says no expectation should be made of acceptance into feeder-pattern schools. Zoning and capacity can change, so confirm your address with the district's Student Assignment office before you rely on it. We do not rank schools.
Where is Winding Cypress, and how far is everything?
Winding Cypress is in East Naples, ZIP 34114, north-east of US 41 and east of Collier Boulevard, with its entry road off Collier Boulevard shared with Verona Walk. The nearest emergency room is Physicians Regional Collier Boulevard, about 2.5 miles and 6 minutes away, and Interstate 75 Exit 101 is about 6.1 miles and 11 minutes away.
| Destination | Road miles | Minutes, free flow |
|---|---|---|
| Physicians Regional Medical Center, Collier Boulevard (24-hour ER) | 2.5 | 6 |
| Interstate 75 Exit 101 (carried) | 6.1 | 11 |
| Lely High School | 3.7 | 11 |
| Physicians Regional East Naples Urgent Care | 6.7 | 12 |
| Naples Airport | 9.9 | 19 |
| Fifth Avenue South | 10.5 | 20 |
| Naples Pier | 11.4 | 22 |
| NCH Baker Hospital | 11.1 | 22 |
| Coastland Center | 12.1 | 23 |
| Physicians Regional Pine Ridge | 12.7 | 21 |
| Southwest Florida International Airport (RSW) | 39.1 | 51 |
Source: free-flow model routes from the entry road at Collier Boulevard on October 29, 2026, with the Exit 101 figure carried from September 2026 research. In season, Collier Boulevard and US 41 run slower. Call 911 in an emergency; we do not suggest which facility to choose.
Groceries and shopping
A Publix at 8585 Collier Boulevard is about 2 to 3 miles from the entry road, and two research runs gave 1.7 and 2.9 road miles from different origins. Coastland Center is about 12 miles away. A second Collier County Costco is under construction at the southeast corner of Collier Boulevard and Rattlesnake Hammock Road, about 3 miles north, and its opening date was not announced as of October 19, 2026.
Utilities
The Collier County Water Sewer District, an independent special district, provides county water, wastewater and irrigation-quality reclaimed water, and the county ended fluoride addition on February 13, 2024. Whether Winding Cypress sits inside its service area is not stated on any page we read, so confirm in the closing documents. Florida Power and Light serves East Naples, and internet providers vary by address and are not bundled in the association's dues.
What is being built near Winding Cypress?
Interstate 75's Collier Boulevard interchange is being rebuilt for $97 million over 1.3 miles with completion expected in early 2027, Collier Boulevard is being widened to six lanes north of the community, and a second Costco is under construction. Dates below are those the Florida Department of Transportation and the county give.
Interstate 75 at Collier Boulevard
The Florida Department of Transportation project 425843-2 rebuilds the southbound on and off ramps and the northbound on-ramp at Exit 101, with single-lane flyover ramps over Beck Boulevard and Davis Boulevard, at a construction cost of $97 million. FDOT lists the expected completion as early 2027, later than the late 2026 date an older factsheet gave, and overnight closures were scheduled for October 25 and 26, 2026.
Collier Boulevard Phase III
Collier County's Phase III widens Collier Boulevard from four to six lanes between City Gate Boulevard North and Green Boulevard, about 2.1 miles, the last of five projects covering 15 miles from US 41 to Immokalee Road. The work zone is north of the community, and we did not read a construction start date.
New communities and shopping
Esplanade by the Islands and Seven Shores are selling new homes in the same ZIP, and a July 2024 land purchase for Mattamy Homes' Summerlit planned 249 homesites in the same area. The Costco tract is on the Hacienda Lakes commercial land, and Hacienda Lakes residents reached an agreement with Costco about truck routing. For the new-home picture see Naples new construction.
A short history of Winding Cypress
Winding Cypress began as a Barron Collier development order approved by Collier County in December 1999, was bought by DiVosta in 2014 and 2015 and opened its model park on March 14, 2015. Its last recorded builder deed is dated December 21, 2023. Data updated: October 2026.
| Date | Event |
|---|---|
| December 14, 1999 | Collier County approves the Winding Cypress development of regional impact, Development Order 99-4, on the application of Barron Collier Company |
| January 30, 2014 | Winding Cypress Homeowners Association, Inc. incorporated by DiVosta (state record carried) |
| July 10, 2014 | Phase 1 land takedown, $5,025,000; conservation easement recorded the same day |
| December 14, 2014 | DiVosta announces pre-sales from $301,990 and 774 planned homesites, selling from the Verona Walk sales center |
| January 27, 2015 | Phase One plat recorded |
| March 14, 2015 | Model Park Grand Opening at 7225 Wiregrass Court |
| April 30, 2015 | Second land takedown, $15,356,250 |
| June 30, 2015 | First recorded DiVosta deed to a buyer |
| September 18, 2016 | DiVosta page shows the 17,500 square foot clubhouse under construction |
| June 6, 2019 | DiVosta passes 500 homes sold |
| December 3, 2020 | Four new plans released for the final phase |
| December 9, 2023 | DiVosta page says only one opportunity remains |
| December 21, 2023 | Last recorded DiVosta deed to a buyer |
Sources: DiVosta page captures, trade press and county and recorded-instrument facts carried from earlier research. The count of planned homes moved from 774 in December 2014 to 781 in the district's 2015 engineer's report and 766 built; we print 766.
The county approvals
The development order sits inside the Winding Cypress planned unit development, which the county still cites as Ordinance 02-35, as amended. The county's list carried "built out" for the whole planned unit development in February 2026. The community development district was created by Ordinance 2015-48 in September 2015 and covers 358.06 acres, the developed footprint.
Closings by year
DiVosta's recorded deeds to buyers, carried from earlier research, totaled 67 in 2015, 127 in 2016, 114 in 2017, 111 in 2018, 109 in 2019, 83 in 2020, 90 in 2021, 53 in 2022 and 9 in 2023, 763 in all of 766 homes, with three legal-description variants missed. A June 2019 trade release agrees on scale, reporting more than 500 homes sold.
Talk to a Domain Realty Group Winding Cypress specialist
Domain Realty Group, the #1 team in Southwest Florida since 2012, shows Winding Cypress homes to buyers and prices them for sellers from our Naples office on Galleria Court, using 77 qualified county sales over 24 months. Call 239-441-2816. Data updated: October 2026.
Ready to see Winding Cypress homes?
Tell us your price range, the series and plat you prefer and whether you want a lake or preserve view, and a Domain Realty Group agent, from the #1 team in Southwest Florida since 2012, will pull the recorded sales for those streets, order the estoppel documents and check the lot's flood letter before you tour. Contact us, meet our agents or call 239-441-2816, or open the all-homes search for what is listed now.
Thinking of selling your Winding Cypress home?
Domain Realty Group, the #1 team in Southwest Florida since 2012, builds a price from the recorded sales on your own plat and series, not a community average that mixes five plats. Our team's Winding Cypress home valuation guide explains how that valuation works. Request a free valuation on our home valuation page or call 239-441-2816. With 39 qualified sales in 2025 and 33 through October 2, 2026, the right price and presentation matter, and the under $800,000 search shows what a buyer sees in the lower half of the market.
Frequently Asked Questions about Winding Cypress homes for sale
These are the questions buyers ask most about Winding Cypress homes for sale in Naples, answered from the county record, the recorded declaration and government sources, with dates. Data updated: October 2026. Domain Realty Group, the #1 team in Southwest Florida since 2012, can give an address-level answer at 239-441-2816.
Is Winding Cypress in Naples a gated community?
Yes. Winding Cypress is gated, and DiVosta described an entry gate with a guard house in 2015. The association budgets $220,000 for gate access control in 2026, but its Declaration disclaims any representation about security and staffing hours are not published, so ask the association for current gate procedures before you tour.
Where is Winding Cypress in Naples?
Winding Cypress is in East Naples, ZIP 34114, north-east of US 41 and east of Collier Boulevard, with its entry road shared with Verona Walk. The association office is at 7180 Winding Cypress Drive. Physicians Regional Collier Boulevard is about 2.5 miles away, and Interstate 75 Exit 101 is about 6.1 miles away.
Who built Winding Cypress?
DiVosta Homes, a PulteGroup brand, was the only builder. It bought the land from Barron Collier entities in 2014, 2015 and 2018, opened its model park on March 14, 2015, and recorded its last deed to a buyer on December 21, 2023. Every home for sale today is a resale.
How many homes are in Winding Cypress?
The association's site and the district budget count 766 homes: 152 attached Villa Series homes, 406 Classic Series homes on 50 foot homesites and 208 Estate Series homes on 65 foot homesites. DiVosta planned 774 homesites in 2014, and the larger planned unit development that includes Verona Walk is a different, bigger count.
Is Winding Cypress a Del Webb community?
No. DiVosta built Winding Cypress. DiVosta and Del Webb are both PulteGroup brands, which is why the names get mixed up, but Del Webb never built here. The recorded Declaration also contains no age restriction, so Winding Cypress is not a Del Webb style age-restricted community either.
Is Winding Cypress a 55+ community?
No. The recorded Amended and Restated Declaration contains no age restriction, and a search of the whole document for age, 55, adult, senior and housing for older persons found nothing. The rules set a minimum age of 13 for the fitness center and 16 for the spa. Check the current rules with the management office.
What are the HOA fees at Winding Cypress in Naples?
The 2026 approved budget sets annual dues, including a $484 food and beverage minimum, at $6,247.75 for a Villa, $6,657.76 for a Classic and $7,067.22 for an Estate home. Dues are billed quarterly, and the quarterly installments are about 1.0 percent below 2025's, as of October 29, 2026.
What do the Winding Cypress HOA fees cover?
The budget funds landscape maintenance at $1,673,505, gate access control, management, on-site staff, property insurance, reserves and the amenity center, including the Shady Palm Cafe's net loss through a $223.89 assessment. No golf membership appears in the dues. Dues do not include the district assessment, solid waste or property tax.
How much is the Winding Cypress CDD fee?
For fiscal year 2026/27 the district assessment is $1,643.98 for a Villa and up to $2,338.98 for a Phase 3 home on a 65 foot homesite. It combines $794.98 of operations and maintenance with bond debt service and appears on the Collier property tax bill. It has been unchanged for three years.
What is the difference between an HOA and a CDD in Winding Cypress?
The Winding Cypress Homeowners Association is a nonprofit that enforces the Declaration and runs the amenity center and gate. The Winding Cypress Community Development District is a local government special district created by county ordinance that finances and maintains roads, stormwater and lakes, and bills its assessment on the property tax bill.
Do CDD fees ever go away?
The debt part ends when the bonds are paid. Winding Cypress' Series 2015 bonds mature in November 2045 and its Series 2019 bonds in November 2049, with $9,975,000 of par outstanding on January 1, 2026. The operations part continues while the district exists. Ask the district for a payoff statement for a specific home.
Who pays the CDD fee in Winding Cypress?
The owner of each home pays it, as a non-ad valorem line on the Collier County tax bill. The amount depends on lot type and phase, from $1,643.98 for a Villa in Phases 1 and 2 to $2,338.98 for a 65 foot lot in Phase 3. Ask your title company how the current year's bill is prorated at closing.
What is the total of HOA, CDD and solid waste in Winding Cypress?
Adding the 2026 dues, the fiscal year 2026/27 district assessment and the $261.91 solid waste assessment from a 2025 bill gives $8,153.64 for a Villa and up to $9,668.11 for a Phase 3 Estate home a year, before property tax and insurance. Those are the fixed charges only.
What is the property tax rate in Winding Cypress?
The 2025 total millage on a Winding Cypress tax bill was 10.5058 mills, covering the county, schools, fire, water management, the basin and mosquito control, as the components sum. It is a rate on taxable value and not on price. The 2026 bills arrive in November 2026, so read the parcel's own bill.
Can the HOA take your home in Florida?
Winding Cypress assessments are secured by a continuing lien under the Declaration, so unpaid assessments can lead to enforcement under Florida law. We do not give legal advice. Ask a Florida attorney about foreclosure rules, and ask for the estoppel certificate, which shows unpaid dues and any special assessment, before you buy.
Can the HOA reject me as a buyer at Winding Cypress?
No. Declaration section 12.3 says the association has no authority to disapprove a proposed conveyance. The owner must give written notice at least 20 days before closing with the purchase contract, and the Board issues a Certificate of Approval within 20 days or approval is deemed given. Leases are different and can be refused for good cause.
How long does HOA approval take for a Winding Cypress sale?
The Board has 20 days from the notice and any requested information to approve the sale, and silence for 20 days counts as approval. Notice should go in on the day the contract is signed, and the estoppel certificate is due within 10 business days of the request. The association's actual turnaround is not published.
How long does it take to close on a Winding Cypress home?
The rules set the pace. The owner's notice runs 20 days before closing, the estoppel certificate is due within 10 business days, and the buyer's lender needs its own time. A cash buyer can still run into the 20-day window, so we send the notice the day the contract is signed.
Can I rent out a home in Winding Cypress?
Yes, within limits. Leases must be for the whole home, at least 30 continuous days and no more than one year, and a home may not be leased more than three times in a calendar year. Applications go in 20 days before occupancy, and the Board can decline only for good cause.
What is the estoppel certificate fee in Winding Cypress?
The association states its fee on the certificate. Florida's current caps, per the Department of Business and Professional Regulation fee sheet read October 29, 2026, are $299 for preparation and delivery plus $119 if expedited to three business days, and a late certificate carries no fee. The certificate is due within 10 business days.
What is the resale capital contribution at Winding Cypress?
The association's 2025 audit lists a resale capital contribution of $1,050, paid by the buyer at closing, raised from $1,000 in March 2023. The Board sets it each year, with a 10 percent annual cap, and the 2026 amount is not published, so confirm it on the estoppel certificate.
Are there new construction homes left in Winding Cypress?
No. DiVosta's last recorded deed to a buyer is dated December 21, 2023, the county recorded 0 builder-direct sales in the latest 12 months, and DiVosta's Naples page now lists Terreno at Valencia instead. Homes for sale in Winding Cypress are resales. For builder-new homes, see our Naples new construction guide.
Does the DiVosta warranty transfer to a resale buyer?
The DiVosta ten-year structural warranty is described as transferable, but only to a subsequent owner who takes title within the warranty period and uses the home as a residence. Each home's term runs from its own closing date, so ask the seller for the deed date and the warranty book, and ask an attorney about section 95.11.
What amenities does the Winding Cypress clubhouse have?
The September 2026 rules list a heated resort pool and cabana, a spa, a fitness center with a Movement Room, locker rooms, an event room, an internet cafe, a library, a catering kitchen, fire pit areas, complimentary Wi-Fi, the association office and the Shady Palm Cafe. Use is limited to owners, tenants, resident family and escorted guests.
How many tennis and pickleball courts does Winding Cypress have?
The September 2026 Rules and Regulations list 4 tennis courts, 8 pickleball courts and 4 bocce courts. An older association page still showed five tennis courts and four pickleball courts, so confirm the current layout with the association before you rely on either count.
Is there a golf course in Winding Cypress?
No. Neither the amenity list nor the rules include golf. Golf carts are allowed on community roads with insurance and registration. The nearest public golf includes Lely Resort's Mustang and Flamingo Island courses and Hibiscus Golf Club, and we have not verified drive times from the gate.
Does Winding Cypress have a restaurant?
Yes. The Shady Palm Cafe is the poolside bar and restaurant in the amenity center. Owners use a membership account and tab, and the cafe is not available for private-event catering. Hours are seasonal and posted by the association. A separate food and beverage minimum of $484 a year applies in 2026.
Can Verona Walk residents use the Winding Cypress amenities?
No stated right exists. The rules say use is exclusive to Winding Cypress owners, tenants, resident family and escorted guests. Verona Walk is a separate community with its own association and Town Center, though the two share an entry road and certain shared costs under a recorded agreement.
What FEMA flood zone is Winding Cypress in?
FEMA's effective map, dated February 8, 2024, shows Zone AE at all 13 sampled addresses, with a base flood elevation of about 8.0 feet. Some individual homes have FEMA letters moving them to shaded Zone X. Ask the seller for the flood zone, any FEMA letter and the elevation certificate.
Do I need flood insurance in Winding Cypress?
If you use a mortgage and the home is in a mapped high-risk zone such as AE, the lender generally requires flood insurance. A FEMA letter can lift the federal requirement, but the letters say the lender may continue it. A cash buyer decides for themselves. Ask a licensed agent early, because a policy normally has a 30-day wait.
What is a LOMR-F and do Winding Cypress homes have them?
A LOMR-F is a FEMA letter that removes a lot or structure from the high-risk zone based on survey elevation. FEMA records carried from earlier research show 25 cases naming Winding Cypress, including 16 single-lot letters since the 2024 map covering 15 homes. Ask whether a specific home has one.
Is the Collier County flood map changing?
Yes. A new preliminary map was released March 20, 2025, and a 90-day appeal and comment period began August 19, 2026. The county lists summer 2027 as the target for the new map to take effect, subject to change. The effective map is still the February 8, 2024 map until then.
What hurricane evacuation zone is Winding Cypress in?
County records carried from September 2026 place Winding Cypress in Evacuation Zone D. Evacuation orders are issued by zone; Hurricane Ian's mandatory order covered Zone A and Milton's covered Zones A and B. Confirm any address on the county lookup and the state's Collier map before storm season.
Did Hurricane Ian flood Winding Cypress?
No source we found names Winding Cypress in a storm damage report, and a district minute carried from earlier research says no significant damage was noted by the community. Ian's worst surge flooding in Collier was south and west of US 41, and Winding Cypress lies north-east of it. Ask the seller about the specific home.
How old are Winding Cypress roofs, and does the 15-year rule matter?
Homes were built from 2015 to 2023, so the first original roofs reach 15 years about 2030. Florida section 627.7011 bars an insurer from refusing or non-renewing a policy solely because a roof is under 15 years old, and requires an inspection option at 15 or older. Roof permits show each roof.
What must a seller tell me about flooding?
Florida section 689.302 requires the seller to give a flood disclosure at or before the contract. It asks whether the seller knows of flooding that damaged the property, filed a flood insurance claim including a National Flood Insurance Program claim, or received flood assistance including FEMA assistance. Read it before you sign and ask follow-up questions.
Which public schools serve Winding Cypress?
For the 2026-27 school year, the district address lookup assigned Lely Elementary School, Manatee Middle School and Lely High School for every sampled address, as carried in October 2026. For 2025-26 the state grades are A, A and B. Confirm your address with Collier County Public Schools before relying on it.
What is the closest hospital to Winding Cypress?
Physicians Regional Medical Center, Collier Boulevard, at 8300 Collier Boulevard, is about 2.5 road miles and 6 minutes from the entry road, free flow. It is a 130-bed, Joint Commission accredited hospital with a 24-hour emergency room that began accepting patients in February 2007. Call 911 in an emergency.
How far is Winding Cypress from I-75, and is the interchange changing?
Interstate 75 Exit 101 at Collier Boulevard is about 6.1 road miles and 11 minutes from the entry road without traffic. The Florida Department of Transportation is rebuilding the interchange with flyover ramps at a cost of $97 million, with completion expected in early 2027, so lane shifts and closures continue until then.
Are home prices declining in Winding Cypress?
On the county record the 12-month median was $825,000 on 42 sales, against $830,000 on 35 sales in the prior 12 months, a decline of about 0.6 percent. The annual median peaked at $900,000 in 2023 and was $835,000 in 2026 through October 2. Medians describe what closed, not what a home is worth.
How do Winding Cypress and Verona Walk compare?
Both are DiVosta communities that share an entry road, but they have separate associations, districts and amenities. In the 12 months to October 2, 2026, the county recorded 42 Winding Cypress sales at an $825,000 median and 89 Verona Walk sales at a $495,000 median. Winding Cypress has 766 homes and Verona Walk 1,920.
What are the pet rules in Winding Cypress?
The Declaration allows no more than three pets, excluding tropical fish, and prohibits pit bulls, wolf hybrids and dogs prone to aggression. The rules require a handheld, non-retractable leash no longer than six feet, and pets are not allowed inside the amenity center. There are two dog parks, one for small and one for large pets.
Can residents fish or kayak on the Winding Cypress lakes?
No. The rules state that the lakes are controlled by the district and residents have no recreational access, including fishing and water toys. The community has no boat ramp or marina. Public paddling is at county parks, such as Sugden Regional Park.
How big are Winding Cypress homes?
DiVosta's captured pages list plans from the 1,542 square foot Serenity villa plan to 2,852 square feet and up for the Stonewater, and a 2020 release cites plans above 3,800 square feet. These are builder sizes, not county records, and options vary, so check the plan and the survey for a specific home.
What are the Villa, Classic and Estate series?
They are DiVosta's three collections: attached Villa Series homes, Classic Series single-family homes on 50 foot homesites and Estate Series single-family homes on 65 foot homesites. The district counts 152, 406 and 208 homes, and the series sets which district and association tier a home pays. Check the tier on the tax bill.
What documents should I request before buying a Winding Cypress home?
Ask for the estoppel certificate, current budget, recorded Declaration and rules, latest audit, the district's assessment statement, the seller's flood disclosure, any FEMA letter, the elevation certificate, the wind mitigation report, roof permits and the warranty book. They show what a buyer owes and what the home has.
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About Domain Realty Group in Naples
Domain Realty Group is a Southwest Florida real estate team based at 9180 Galleria Ct #200 in Naples, with offices in Bonita Springs and Fort Myers, working Lee, Collier and Charlotte counties. Domain Realty Group has been the #1 team in Southwest Florida since 2012, with $2.5 billion in team production and more than 4,000 transactions. We tracked 77 qualified Winding Cypress sales over 24 months on the county record, and read the recorded Declaration, the 2026 budget and the district's budget, to build this page.
The team is led by Jesse McGreevy and Marc Comisar, with over 45 years of combined direct experience between them. Meet our agent-partners on our agents page and learn about Domain Realty Group. Domain Realty Group has been the number one team in Southwest Florida since 2012, and our Naples office on Galleria Court serves buyers and sellers across East Naples and the Collier Boulevard corridor.
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239-441-2816
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Where to go next: Naples homes for sale and communities, all Naples communities, Naples new construction, Verona Walk, Naples Reserve, Fiddler's Creek, Treviso Bay, Lely Resort, Island Walk, Valencia Trails and current listings.
Sources
Every figure on this page traces to one of the sources below. No real estate portal or other brokerage is cited, by policy. County sale, parcel and roll figures come from the Collier County Property Appraiser's public data files as loaded on October 29, 2026, with the newest qualified Collier sale in the index dated October 2, 2026; web sources and government pages were read on October 29, 2026 unless a date is given, and items marked carried were read in earlier research runs, the latest on October 28, 2026. Distances are approximate road miles. Data services and recorded-instrument indexes are named in plain text and are not linked.
Figures on this page: county records, taxes and Florida law
- Collier County Property Appraiser public data bundle (parcels, buildings and sales files, as loaded October 29, 2026); the appraiser's own site is not linked by policy
- Florida Department of Revenue, property tax data portal
- Florida Department of Revenue, real property use code definitions (Rule 12D-8.008)
- Florida Statutes section 720.30851, estoppel certificates
- Florida Statutes section 720.401, prospective purchasers
- Florida Statutes section 190.048, contract disclosure for community development districts
- Florida Statutes section 95.11, limitations on actions
- Florida Statutes section 689.302, seller flood disclosure
- Florida Statutes section 627.7011, roof age and homeowners insurance
- Florida Department of Business and Professional Regulation, estoppel certificate fee caps
- Collier County FY2025-26 adopted budget, millage rates
- Collier County Public Schools FY2025-26 final budget, millage
- Greater Naples Fire Rescue District FY2025-26 budget book
- Collier County Tax Collector 2025 tax bill for a Winding Cypress parcel (carried from September 2026 research; the bill page is a data service and is not linked)
Association, district, documents and management
- Winding Cypress Homeowners Association, home page
- Winding Cypress HOA, Amended and Restated Declaration (hosted copy dated February 5, 2024)
- Winding Cypress HOA, 2026 Approved Budget
- Winding Cypress HOA, Rules and Regulations, September 2026
- Winding Cypress HOA, 2025 audit
- Winding Cypress HOA, contact and office hours
- Winding Cypress HOA, community amenities
- Winding Cypress HOA, clubs
- Winding Cypress HOA, visitors and agents documents
- Winding Cypress HOA, sales and leasing application
- Winding Cypress HOA, tennis rules, January 2024
- Winding Cypress Community Development District, home page
- Winding Cypress CDD, Final Budget FY2026/27
- Winding Cypress CDD, financial documents
- Winding Cypress CDD, documents index
- Winding Cypress CDD, lake assessment dated March 21, 2024
- Winding Cypress CDD, creation ordinance 2015-48
- Seacrest Southwest Property Management, management company
Builder history and warranty
- DiVosta Winding Cypress page, capture of March 13, 2015
- DiVosta Winding Cypress page, capture of July 21, 2019
- DiVosta Winding Cypress page, capture of August 12, 2020
- DiVosta Winding Cypress page, capture of December 9, 2023
- DiVosta Winding Cypress page, capture of September 18, 2016 (carried)
- DiVosta, 10-year warranty page
- PulteGroup and DiVosta Home Protection Plan warranty book
- DiVosta warranty highlights sheet
- Florida Weekly, DiVosta introduces four new floor plans at Winding Cypress, December 3, 2020
- Florida Weekly, Winding Cypress surpasses 500 homes sold, June 6, 2019
- Naples Daily News archive, DiVosta building four models and a sales center at Winding Cypress, December 14, 2014
- Business Observer, DiVosta Homes buys 850 acres for Winding Cypress, May 22, 2015
- Naples Daily News, DiVosta releases new homesites at Winding Cypress, March 23, 2019
- Wikipedia, PulteGroup
- Wikipedia, Winding Cypress, Florida (census place)
- Barron Collier Companies
- Collier County planned unit development master list (carried, February 2026)
- Recorded Collier County deeds, plats, development order and easements for Winding Cypress (carried from September 2026 research; recorded-instrument indexes are named in plain text and are not linked)
Amenities, golf and nearby recreation
- Deangelis Diamond, Winding Cypress amenity center project portfolio
- Lely Resort Golf and Country Club
- Hibiscus Golf Club
- Florida Forest Service, Picayune Strand State Forest
- Florida Fish and Wildlife Conservation Commission, Picayune Strand
- Collier County Parks, boat parks
- Verona Walk association site
Comparison communities and nearby new homes
- DiVosta, Terreno at Valencia
- Taylor Morrison, Esplanade by the Islands
- Toll Brothers, Seven Shores
- GL Homes, Valencia Sky
- Mattamy Homes, Summerlit land purchase, July 15, 2024 (carried)
- Domain Realty Group, Naples new construction guide
Flood, hurricanes and insurance
- Collier County, proposed Flood Insurance Rate Map notice, August 2026
- Collier County, floodplain management
- FEMA Map Service Center
- FEMA preliminary map viewer
- FEMA, Risk Rating 2.0 frequently asked questions
- FEMA, Risk Rating 2.0, April 2025
- FEMA, flood insurance
- Florida Division of Emergency Management, Know Your Zone
- National Hurricane Center, Hurricane Ian report
- National Weather Service Miami, Hurricane Ian summary
- National Hurricane Center, Hurricane Milton report
- Florida Office of Insurance Regulation, wind mitigation
- Citizens Property Insurance, inspections
- Citizens Property Insurance, Clearinghouse eligibility
- My Safe Florida Home
- Florida Realtors, Florida expands flood disclosures, September 30, 2025
- USDA Forest Service, Wildfire Risk to Communities, Collier County
- Florida Building Commission, code effective dates
Schools, health care, roads and local services
- Collier County Public Schools, 2025-2026 school and district grades
- Collier County Public Schools, parental choice
- Physicians Regional Medical Center, Collier Boulevard
- Physicians Regional, urgent care
- NCH Healthcare System, Naples locations
- Florida Department of Transportation, I-75 at SR 951 project 425843-2
- Florida Department of Transportation, Collier County road watch
- Collier County, transportation engineering projects
- Collier County, water services
- Florida Power and Light, start service
- Hoodline, second Costco rises in East Naples, October 2026
- WGCU, Newman Road wildfire near Picayune Strand, April 2026
- National Center for Education Statistics, Common Core of Data school search, 2024-25 enrollment (carried; data service, not linked)
- Free-flow route times from the entry road at Collier Boulevard, computed October 29, 2026 with OpenStreetMap geocodes and a public routing service (data services, not linked)