Winding Cypress, East Naples Florida
A free, no-obligation valuation from McGreevy and Comisar. Inside one Winding Cypress gate, a villa, a Classic home and an Estate home sell in different price bands, so a community average tells you very little. The only number that matters is yours.
Updated September 2026 · Jesse McGreevy and Marc Comisar, Domain Realty
If you own one of the 766 DiVosta homes behind the gates of Winding Cypress in East Naples, the honest answer to what it is worth starts with your series, your plat and your lot, not with a community median. Winding Cypress sold 48 homes in the twelve months to September 23, 2026, and those sales ran from $455,000 for a Jacaranda Lane villa to $1,495,000 for an estate-sized home on Winding Cypress Drive. The full community picture, from the clubhouse and the fee stack to schools and hurricane posture, lives on our Winding Cypress community guide. This page does one job: it shows how a Winding Cypress home is actually valued, from the Southwest Florida MLS, Collier County’s recorded sales, the district and association budgets and FEMA’s flood file, and it gives you two ways to get your own number. Use the Home Valuation form at the top of this page, or call Jesse McGreevy direct at (239) 898-6072.
A Winding Cypress home in East Naples is worth what its series, plat, lot, flood record and condition support. Across the 48 MLS closings in the twelve months to September 23, 2026, single-family homes sold at a median of $875,000 and attached villas at $575,000, but the individual sales ran from $455,000 to $1,495,000.
Data updated: September 2026 (Southwest Florida MLS, Development: Winding Cypress, pulled 23 Sep 2026)
Winding Cypress resolves into three products and two practical price bands. The 152 attached villas on Jacaranda Lane and the 7093 to 7202 block of Live Oak Drive form the entry band: 13 villa closings in the trailing twelve months, a median of $575,000, a range of $455,000 to $635,000 and a median of 1,554 square feet of living area. The 614 detached homes, 406 Classic Series homes on 50-foot homesites and 208 Estate Series homes on 65-foot homesites, form the second band: 35 closings, a median of $875,000, a range of $575,000 to $1,495,000 and a median of 2,158 square feet of living area. Inside that detached band, the plan, the homesite width, the plat and the view decide where a specific home lands, and the spread from the bottom of the band to the top is $920,000.
The all-home median of $807,500, the midpoint of the two middle sales at $800,000 and $815,000, is a real number, and it describes almost no individual Winding Cypress home. It blends a 1,554-square-foot paired villa with a 3,656-square-foot Estate plan on a preserve lot. A community median is useful for tracking direction. It is close to useless for pricing one address, and the gap between those two uses is where most Winding Cypress pricing mistakes are made.
We value a Winding Cypress home from four public records laid over one another. The Southwest Florida MLS gives us the brokered closings, their list prices, their days on market and the building label each listing agent entered. Collier County’s recorded, state-qualified sales give us an independent count of every arm’s-length transfer. The district’s fiscal 2026/27 budget and the association’s 2026 approved budget give us the exact carrying cost your buyer will underwrite. FEMA’s flood hazard layer and the county’s Elevation Certificate layer give us the flood record your buyer’s insurer will price. Then we walk the house, because condition, upgrades, the pool and the view are the variables no record captures.
The fastest start is the Home Valuation form at the top of this page, or our free home valuation request if you are reading this somewhere else. It takes about a minute: the address, a line about condition and upgrades, and how to reach you. It is free and there is no obligation to list. What comes back is not an instant number on a screen. It is a written opinion of value built from the recorded sales of your own series and plat, with the sources named, plus the carrying cost picture your buyer will underwrite. If you would rather talk first, call Jesse McGreevy direct at (239) 898-6072 or Marc Comisar at (239) 287-5873. McGreevy and Comisar are Top 1% Real Estate Agents Nationally Since 2008.
McGreevy and Comisar should value your Winding Cypress home because we build every number from the Southwest Florida MLS, Collier County’s recorded sales and the community’s own budgets rather than a portal feed, and we have been Top 1% Real Estate Agents Nationally Since 2008. In a market defined by series and plat, method decides the outcome.
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. If you are comparing agents across the whole city before you choose who values your home, our guide to the best real estate agents in Naples sets the teams side by side on the public record: reviews, licence history and published production.
McGreevy and Comisar lead Domain Realty Group, a full-service Southwest Florida real estate team. Learn more about our team at DomainRealtyGroup.com.
You get Jesse and Marc, not an assistant with a template. Jesse McGreevy builds the pricing analysis, reads the recorded Declaration, the district budget and the FEMA file for your address, and assembles the paperwork your buyer will ask for. Marc Comisar walks the house, judges condition and upgrades against what is actually selling along Collier Boulevard, and handles the field work, which is what lets a seasonal Winding Cypress owner get a real opinion of value without flying down. Read more about how the team is built on the about McGreevy and Comisar page.
DiVosta recorded its last builder-to-buyer deed in Winding Cypress on December 21, 2023, per the Collier County Clerk’s official records, so every home now changes hands as a resale and there is no builder price sheet left to anchor a buyer. Collier County’s recorded, state-qualified sales confirm it: 39 qualified sales between September 2025 and the file’s newest recorded sale on June 19, 2026, every one a resale and none builder-direct. Your buyer’s reference points are now the last few resales of your own product, which is why an unsupported list price stands out quickly and a well-evidenced one holds.
This page answers what your home is worth. If you have decided to sell and want the full listing plan, pricing, marketing, negotiation and the association’s sale steps, read our guide to selling your home in Winding Cypress. If you are buying your next home inside the same gates, start with buying a home in Winding Cypress, and for buyers anywhere in Southwest Florida, read how we represent buyers in Southwest Florida. For the wider city around your home, our Naples real estate guide covers every major community.
Winding Cypress home values rest on a handful of recorded facts: 766 DiVosta homes in three series, a $875,000 single-family and $575,000 villa median over twelve months, 2.2 months of supply, published association and district charges, and a Zone AE flood map. These eight points frame every valuation we write here.
Data updated: September 2026 (Southwest Florida MLS, pulled 23 Sep 2026; HOA and CDD budgets as linked)
A Winding Cypress home is valued by narrowing the product and widening the window: same series, similar plan and living area, matched plat and district debt level, matched lot and view, matched flood record and condition, then recorded sales across enough months to be meaningful, tested against the nine active listings and the 95.67 percent median sale-to-list ratio.
Data updated: September 2026 (Southwest Florida MLS, pulled 23 Sep 2026; CDD FY2026/27 budget; FEMA NFHL)
The Southwest Florida MLS labels every Winding Cypress listing either “Single Family” or “Villa Attached”, and it has no field that separates a Classic Series home on a 50-foot homesite from an Estate Series home on a 65-foot homesite. Portals that read the MLS therefore show one undifferentiated detached market. We read the series from the homesite width on the recorded plat, the floor plan and the district’s assessment line for the lot, because a Classic buyer and an Estate buyer are comparing different homes. DiVosta’s Winding Cypress brochure lists the Estate plans, Pinnacle at 2,488 to 3,676 square feet, Tangerly Oak at 2,589 to 2,938 and Stonewater at 2,852 to 3,894 under air, against Classic plans such as the Palmary, Prestige, Prosperity and Mystique at roughly 1,670 to 3,037.
Winding Cypress was recorded in five plats: Phase One (January 27, 2015, 153 homes), Phase 2C (January 11, 2016, 23 homes), Phase 2 (March 14, 2016, 245 homes), the Phase 2 Replat (March 28, 2017, 143 homes) and Phase 3 (November 15, 2018, 202 homes), per the Collier County Clerk’s plat index and the county’s parcel layer. Homes on the Phase 3 plat carry Series 2019 district debt of $1,429 a year on a 50-foot homesite or $1,544 on a 65-foot homesite, against $954 or $1,060 for the same widths in Phases 1 and 2, per the district budget. About 10 lots recorded on Phase 2 family plats also carry Phase 3 debt, so the level for a specific address is read from its own tax bill, never from its street alone.
Median living area on the 35 single-family closings was 2,158 square feet and on the 13 villa closings 1,554 square feet, per the Southwest Florida MLS. Price per square foot only means something inside a product of similar homes, which is why we compute it for villas and detached homes separately and then narrow it by plan. The detached homes sold for a median of $405.92 per square foot of living area and the villas for $370.01, and the largest detached home to close in the year, 3,656 square feet at 7412 Winding Cypress Drive, set the top of the market at $1,495,000.
Winding Cypress sits inside about 1,176 acres across its five plats, of which about 818 acres are recorded preserve tracts, and about 70 home lots, 46 detached and 24 villa lots, touch a recorded preserve tract, 40 of them in Phase One, per the county’s parcel layer. The district’s 29 stormwater lakes add water views to many other lots. No public dataset measures a preserve or lake premium in Winding Cypress, so we do not apply a rule of thumb. We price the view from the specific resales that had one, and we say so in writing when the evidence is thin.
On FEMA’s map effective February 8, 2024, every Winding Cypress address sampled across the five plats returned Zone AE with a base flood elevation of 8.0 feet NAVD88, per the National Flood Hazard Layer and its BFE lines. Since 2024, 16 single-lot FEMA determinations covering 15 homes have moved individual lots or structures to shaded Zone X, per FEMA’s LOMR-F layer. Two homes on the same street can therefore present very differently to a buyer’s insurer, and that difference reaches the monthly cost and therefore the price.
DiVosta built Winding Cypress in steel-reinforced concrete block with engineered roof trusses, hurricane tie-downs and tile roofs, with galvanized steel hurricane shutters as standard and impact glass as an option, per its brochure. A home with impact glass, a current wind mitigation report on the state form and a clean roof record hands the buyer’s insurer documented credits. A home with only the original shutters and no report hands the insurer nothing, and the buyer prices that gap.
Every home in Winding Cypress was built between 2015 and 2023, so the differences between two homes of the same plan are rarely age and almost always choices: an added pool and screen enclosure, an extended lanai, impact glass, flooring, kitchen finishes, a converted den, the quality of the landscaping. Those are the variables no record captures, and they separate two otherwise identical homes on the same street by more than any statistical adjustment. So we see the house.
With 48 closings a year across three products, a ninety-day comparable search in one series returns very little. We widen the window to one, two or three years inside your product and adjust older sales for time using the community’s own calendar-year medians, which show a single-family peak of $1,000,000 in 2024, a reset to $860,000 in 2025 and $895,000 in 2026 to September 23, per the Southwest Florida MLS. That series is set out in full further down this page.
Finally we test the opinion of value against the nine homes actively for sale on September 23, 2026 and against the 95.67 percent median sale-to-list ratio. The seven active single-family homes carried a median list price of $1,250,000 against a trailing median single-family sale of $875,000, so a price set against neighbours’ asking prices rather than against closed sales is a price that sits.
Winding Cypress is a market of 766 homes in three products where the MLS cannot tell a Classic home from an Estate home, so a valuation that starts from the right series and plat is worth an hour of your time now. Use the Home Valuation form at the top of this page or our free home valuation request, and if you have already decided to list, read our plan for selling your home in Winding Cypress. Call Jesse direct at (239) 898-6072. Buying as well as selling? Call Marc at (239) 287-5873, or read how we represent buyers in Southwest Florida.
Winding Cypress homes are worth different amounts by product: attached villas sold at a median of $575,000 and detached homes at $875,000 over the twelve months to September 23, 2026. Inside the detached market, the Classic or Estate series, the plat and its district debt level, and the lot decide where a home prices.
Data updated: September 2026 (Southwest Florida MLS, pulled 23 Sep 2026; CDD FY2026/27 budget; HOA 2026 budget; Collier County Property Appraiser records)
Product | Homes | Where | Trailing 12-month MLS closings | MLS median sale | Median living area | 2026 HOA total | CDD total, Phases 1 and 2 / Phase 3 |
|---|---|---|---|---|---|---|---|
Villa Series (attached) | 152 | Jacaranda Lane; 7093 to 7202 Live Oak Drive | 13 | $575,000 | 1,554 sq ft | $6,247.75 | $1,643.98 / none |
Classic Series (50-foot homesite) | 406 | Detached streets | 35 detached closings, Classic and Estate together | $875,000 | 2,158 sq ft | $6,657.76 | $1,748.98 / $2,223.98 |
Estate Series (65-foot homesite) | 208 | Detached streets | (included above) | (included above) | (included above) | $7,067.22 | $1,854.98 / $2,338.98 |
Community | 766 | 15 residential streets | 48 | $807,500 | 2,081 sq ft |
Sources: Southwest Florida MLS, pulled September 23, 2026; the district’s fiscal 2026/27 budget; the association’s 2026 approved budget. The MLS files Classic and Estate homes under one “Single Family” label, so their closings are reported together.
The 152 villas are fee-simple paired homes, each on its own small lot, on Jacaranda Lane (110 villas across the Phase 2 and Phase 2 Replat plats) and the 7093 to 7202 block of Live Oak Drive (40 villas on the Phase One plat), per the county’s parcel layer. The trailing twelve months recorded 13 villa closings at a median of $575,000, $370.01 per square foot of living area, a 94.76 percent median sale-to-list ratio and a median of 50 days on market, the fastest product in the community. The three lowest-priced closings of the year were all villas on Jacaranda Lane, at $455,000, $460,000 and $470,000. Every villa pays the lowest association total and the lowest district debt charge in Winding Cypress, and 24 villa lots touch a recorded preserve tract, which is a pricing variable inside a product that otherwise varies little in size.
The Classic Series is the largest product line, 406 detached homes on 50-foot homesites, per the district’s unit census. Earlier releases sold under the Abbeyville, Martin Ray, Summerwood, Cressida and Infinity names, per DiVosta’s archived 2015 and 2019 community pages, and the four later plans, Palmary, Prestige, Prosperity and Mystique, were introduced in late 2020, per Florida Weekly. A Classic home pays $6,657.76 to the association for 2026 and $1,748.98 or $2,223.98 to the district, depending on plat. Because the MLS cannot separate Classic from Estate closings, the plan and its air-conditioned area are the best public guide to where a Classic home sits inside the detached range, and they move the number more than any other single variable.
The Estate Series is 208 detached homes on 65-foot homesites, built to a specification that added whole-house gutters and DiVosta’s “Tubes in the Wall” feature, per the brochure. Estate plans run from 2,488 to 3,894 square feet under air, which puts them in the upper part of the detached range; the year’s top closing, $1,495,000 for a 3,656-square-foot home at 7412 Winding Cypress Drive on March 11, 2026, sits in the size band of the largest Estate plans, and the 48-month record is $1,895,000, for 7513 Winding Cypress Drive on January 4, 2024. An Estate home pays $7,067.22 to the association and $1,854.98 or $2,338.98 to the district.
Phase One carries 153 homes, 113 detached and 40 villas, on Live Oak Drive, Lily Way, Clamshell Lane, Wiregrass Court and part of Winding Cypress Drive, and it holds the clubhouse tract. It also holds 40 of the roughly 70 lots that touch a recorded preserve tract, the highest share of any plat, and its homes were the first built, from 2015. Phase One is also where several post-2024 single-lot FEMA letters cluster, on Live Oak Drive, per FEMA’s LOMR-F layer, so a Phase One valuation starts by checking the lot’s own flood letter.
The Phase 2 plat carries 245 homes, 193 detached and 52 villas, on Winding Cypress Drive, Blackberry Drive, Jacaranda Lane, Arrowhead Way, Geranium Way and Chenille Court. The Phase 2 Replat carries 143 homes, 85 detached and 58 villas, on Winding Cypress Drive and Jacaranda Lane. Phase 2C is a single cul-de-sac, Mockingbird Court, with 23 detached homes. All three sit in the Phases 1 and 2 district assessment area repaid by the Series 2015 bonds, so their debt charge is the lower of the two, which is a quiet advantage in a buyer’s carrying-cost comparison.
The Phase 3 plat carries 202 detached homes on the south end of Winding Cypress Drive, Pennyroyal Drive, Cocoplum Street, Greenbriar Court and Bromeliad Drive, built from 2019 to 2023. They are the newest homes in the community, and they carry Series 2019 district debt of $1,429 or $1,544 a year, about $475 to $485 more than a like-width home in Phases 1 and 2. That difference is real money to a buyer comparing two similar homes, and it is also offset in part by age: a 2021 home will not meet the 20-year four-point inspection threshold until the 2040s. Phase 3 also recorded one of the year’s top sales, $1,475,000 for 6912 Cocoplum Street on May 13, 2026.
On Collier County’s 2026 preliminary roll, the median county just value is $495,624 for an attached villa and $743,973 for a detached home, per Collier County Property Appraiser records served through the county’s parcel layer. County just value is an assessment for the tax roll, set once a year by one method for every parcel. It is not an asking price, not a sale price and not an estimate of what your home would sell for, and it runs well below the MLS medians. We publish it only because it is the one same-day, same-method measurement across every Winding Cypress home, which makes it useful for ranking products against each other and useless for pricing any one of them.
Price per square foot tells you where a Winding Cypress home sits inside its own product, not what it is worth. Over the twelve months to September 23, 2026, the Southwest Florida MLS shows a median of $405.92 per square foot of living area for detached homes, $370.01 for villas and $394.83 across all 48 closings.
Data updated: September 2026 (Southwest Florida MLS, pulled 23 Sep 2026)
Every price-per-square-foot figure on this page is each closing’s sale price divided by that home’s MLS living area, and then the median of those ratios. It is a living-area figure, and the MLS living area on most Winding Cypress rows comes from county records of the heated and cooled space. It is never comparable with a county-roll figure measured on total area under roof, which runs about 23 percent larger than MLS living area on the villas. When you see a single price-per-foot figure quoted for Winding Cypress anywhere else, ask which area it divides by.
The villa median of $370.01 per square foot of living area and the detached median of $405.92 are close enough to tempt a seller into treating them as one scale. They are not. A villa carries a shared wall, a smaller lot and the lowest charges in the community; a detached home carries its own lot, room for a pool and, on the Estate Series, a 65-foot homesite. The price per foot of a villa is set against other villas, and a detached home against other detached homes.
In the prior twelve months, September 24, 2024 to September 23, 2025, detached homes sold at a median of $417.66 per square foot of living area. In the latest twelve months that fell 2.8 percent to $405.92 while the detached median sale price rose 1.7 percent, from $860,000 to $875,000, per the Southwest Florida MLS. The only way both can be true is that larger homes made up more of this year’s sales. That is ordinary behaviour in every market: price per foot tends to fall as size rises, even when total value rises.
Take your living area from the county record or your builder closing package, not from a marketing flyer, and compare it only with closings in your own product, your own plat and, where possible, your own plan. If your home is one of the larger plans in its series, expect the per-foot figure to soften. If it is one of the smaller, expect it to rise. Then adjust for the pool, the lanai, the openings and the view, which a per-foot figure cannot see at all.
Winding Cypress homes sold at a median of $807,500 across 48 Southwest Florida MLS closings in the twelve months to September 23, 2026, for $38,718,900 in total volume. Detached homes sold at a median of $875,000 on 35 closings and attached villas at $575,000 on 13, with sales from $455,000 to $1,495,000.
Data updated: September 2026 (Southwest Florida MLS, pulled 23 Sep 2026; Collier County Property Appraiser records, newest recorded sale 19 Jun 2026)
Closed Sept. 24, 2025 to Sept. 23, 2026 | All homes | Single-family | Attached villas |
|---|---|---|---|
Closed sales | 48 | 35 | 13 |
Median sale price | $807,500 (midpoint of $800,000 and $815,000) | $875,000 | $575,000 |
Median list price | $829,999.50 (midpoint of $825,000 and $834,999) | $925,000 | $599,900 |
Median living area | 2,081 sq ft (midpoint of 2,078 and 2,084) | 2,158 sq ft | 1,554 sq ft |
Median 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 (46 sales with a figure) | 76 (33 sales with a figure) | 50 |
Sold at or above list price | 7 of 48 | 5 of 35 | 2 of 13 |
Total volume | $38,718,900 | $31,433,900 | $7,285,000 |
Sale price range | $455,000 to $1,495,000 | $575,000 to $1,495,000 | $455,000 to $635,000 |
Source: Southwest Florida MLS, Development: Winding Cypress, pulled September 23, 2026. The development name returned exactly one dictionary entry, so no neighbouring community leaks into these rows. Two sales were entered after closing and carry no days-on-market figure, which is why those medians use 46 and 33 sales.
Collier County’s recorded sales file, the Collier County Property Appraiser records of state-qualified, arm’s-length improved sales, independently confirms the shape of the market. We tracked the county file alongside the MLS: from September 2025 to its newest recorded sale on June 19, 2026, it holds 39 qualified Winding Cypress sales, every one of them a resale and none a builder-direct first sale. The county window ends three months before the MLS window, so the two counts are not meant to match. What the county record adds is a check the MLS cannot give itself: builder-direct sales that never reach the MLS are the reason a county count can outrun an MLS count in newer communities, and in Winding Cypress there are none left, so the MLS figures on this page are not missing a hidden builder market.
The three highest closings of the year were $1,495,000 for 7412 Winding Cypress Drive (March 11, 2026, 3,656 square feet of living area), $1,475,000 for 6912 Cocoplum Street (May 13, 2026) and $1,260,000 for 6839 Winding Cypress Drive (November 21, 2025). The three lowest were all villas on Jacaranda Lane: $455,000 for 7642 Jacaranda Lane (November 17, 2025), $460,000 for 7658 Jacaranda Lane (March 12, 2026) and $470,000 for 7638 Jacaranda Lane (June 24, 2026). Over the four years of MLS history pulled for this page, the record is $1,895,000 for 7513 Winding Cypress Drive, closed January 4, 2024.
Street | Closings, Sept. 24, 2025 to Sept. 23, 2026 | Homes on the street | Product |
|---|---|---|---|
Winding Cypress Drive | 12 | 250 | Detached |
Jacaranda Lane | 12 | 111 | 110 villas, 1 detached |
Live Oak Drive | 10 | 103 | 40 villas, 63 detached |
Pennyroyal Drive | 6 | 53 | Detached, Phase 3 |
Mockingbird Court | 3 | 23 | Detached, Phase 2C |
Blackberry Drive | 2 | 68 | Detached |
Cocoplum Street | 1 | 33 | Detached, Phase 3 |
Clamshell Lane | 1 | 15 | Detached |
Geranium Way | 1 | 15 | Detached |
Lily Way, Wiregrass Court, Arrowhead Way, Chenille Court, Greenbriar Court, Bromeliad Drive | 0 | 95 together | Detached |
Total | 48 | 766 |
Sources: closings, Southwest Florida MLS, pulled September 23, 2026; homes per street, Collier County Property Appraiser records served through the county’s parcel layer. With 766 homes on 15 residential streets, a street with no sale in one year is common and says nothing about demand for it. It does mean that a seller on one of those six streets is pricing from sales on neighbouring streets of the same plat and product.
The MLS building label is entered by the listing agent. County records place at least two Live Oak Drive homes that closed in this window under the “Single Family” label on the block of attached villas between 7093 and 7202 Live Oak Drive, and one of them was labelled a villa in its own 2023 sale. We publish the MLS medians exactly as the MLS reports them, and we read the single-family and villa lines as close approximations rather than exact counts. When we value a Live Oak Drive home, we check the county record for the lot before we choose its comparable sales.
Two readings matter most. First, the gap between the products: at the median, a detached home sold for $300,000 more than a villa. Second, the negotiating room: the median home sold at 95.67 percent of its final list price and only 7 of 48 sold at or above list, so buyers negotiated about 4 percent at the median. A list price with no room in it tends to sit; a list price with deliberate, evidenced room tends to close.
Winding Cypress homes took a median of 73 days on market and sold at a median of 95.67 percent of their final list price across the 48 MLS closings in the twelve months to September 23, 2026. With nine active listings, supply is 2.2 months, so inventory is tight while buyers still negotiate about 4 percent off list.
Data updated: September 2026 (Southwest Florida MLS, pulled 23 Sep 2026)
The ratio is computed against the list price carried on each closed listing, which is the price after any reductions, so it measures how far the median buyer negotiated from the final asking price, not from the first one. Detached homes closed at a median of 96.26 percent and villas at 94.76 percent. Among five East Naples communities searched the same way for single-family homes, Winding Cypress posted the highest median sale-to-list ratio, narrowly ahead of Naples Reserve, which says well-priced homes here hold their price.
Villas sold in a median of 50 days against 76 for detached homes, and villa days on market halved from 107 in the prior twelve months, per the Southwest Florida MLS. The villa is the entry point to Winding Cypress: a buyer gets the same gate, clubhouse, clay courts, pool and café as an Estate owner at about $300,000 less than the detached median. A villa priced at the market meets a deep pool of buyers; a villa priced like a detached home meets none of them.
Nine active listings against 48 closings in twelve months is 2.2 months of supply, a tight, seller-leaning level on its face; by product it was 2.4 months for detached homes and 1.8 for villas. The seven active detached homes ranged from $920,000 to $1,349,500 at a median list price of $1,250,000, and the two active villas were priced at $575,000 and $599,900. Two further homes were under contract. Your listing does not compete with a crowd. It competes with two or three homes in your product and with the buyer’s memory of what the last one on your plat closed for.
The median active detached list price, $1,250,000, sits about 43 percent above the $875,000 median detached sale of the trailing twelve months. That is a labelled market-condition signal, not a price claim: asking prices describe hope, closings describe value. Either the next few closings move the median sharply upward, which the 2025 reset and the 2026 recovery do not yet show, or several of those listings will close well below their asking prices or not at all. A seller who prices against closings rather than against that active group is the seller whose home sells next.
In Winding Cypress the list price is the negotiation’s opening line, and the market has shown it will take about 4 percent off at the median. That does not argue for listing 4 percent high. It argues for listing where the recorded evidence supports, presenting that evidence to the buyer’s agent with the listing, and leaving room that is deliberate rather than accidental.
About four homes a month close in Winding Cypress. A home that sits past its first month tells a small, attentive buyer pool that the price was wrong, and the first reduction is read as the first of several. The time to get the number right is before the listing goes live, which is exactly why a written valuation built from your own product’s recorded sales is worth an hour of your time now.
Winding Cypress home values peaked in 2024, when the single-family median reached $1,000,000, reset about 14 percent to $860,000 in 2025 and recovered to $895,000 in 2026 to September 23. Villas peaked earlier, at $710,000 in 2023, fell to $537,000 in 2025 and stand at $575,000 in 2026.
Data updated: September 2026 (Southwest Florida MLS, closed sales by calendar year, pulled 23 Sep 2026)
Calendar year | Single-family sales | Single-family median | Single-family median per sq ft of living area | Villa sales | Villa median | Villa median per sq ft of living area |
|---|---|---|---|---|---|---|
2023 | 27 | $965,000 | $446.13 | 11 | $710,000 | $456.89 |
2024 | 34 | $1,000,000 | $426.55 | 11 | $610,000 | $392.54 |
2025 | 33 | $860,000 | $408.62 | 9 | $537,000 | $345.56 |
2026, January 1 to September 23 | 26 | $895,000 | $407.42 | 11 | $575,000 | $370.01 |
Source: Southwest Florida MLS, Development: Winding Cypress, pulled September 23, 2026. The 2024 single-family median is the midpoint of two middle sales that were both $1,000,000, and the 2026 figure is the midpoint of $890,000 and $900,000. The search began on September 24, 2022, so 2022 is not shown as a full year.
The detached median rose from $965,000 in 2023 to its $1,000,000 peak in 2024, reset about 14 percent to $860,000 in 2025, and is up about 4.1 percent in 2026 to date at $895,000. Price per square foot of living area fell each year, from $446.13 in 2023 to $407.42 in 2026, which says part of the price movement is mix: larger homes have made up more of the recent sales. A second public record agrees on the 2024 peak. The Florida Department of Revenue’s qualified-sale file for 2025 roll purposes, served on the state’s statewide cadastral layer, also shows a 2024 single-family median of $1,000,000, screened under the Department’s sale qualification codes.
Villas peaked earlier and fell further. The villa median was $710,000 in 2023, $610,000 in 2024 and $537,000 in 2025, about 24 percent below the peak, and it is up about 7.1 percent in 2026 to date at $575,000. On about a dozen sales a year, one unusual closing moves a villa median, so we read the direction across price, days on market and volume together. All three point the same way in 2026: a higher median, faster sales and more closings than in 2025.
Measure | Sept. 24, 2024 to Sept. 23, 2025 | Sept. 24, 2025 to Sept. 23, 2026 |
|---|---|---|
Closed sales, all homes | 40 | 48 |
All-home median sale | $807,500 (midpoint of $785,000 and $830,000) | $807,500 (midpoint of $800,000 and $815,000) |
Single-family closings and median | 31 at $860,000 | 35 at $875,000 |
Single-family median per sq ft of living area | $417.66 | $405.92 |
Villa closings and median | 9 at $560,000 | 13 at $575,000 |
Villa median per sq ft of living area | $360.36 | $370.01 |
Median sale-to-list, all homes | 96.01% | 95.67% |
Median days on market, all homes | 77 | 73 |
Villa median days on market | 107 (midpoint of 100 and 114) | 50 |
Source: Southwest Florida MLS, pulled September 23, 2026. Closings rose 20 percent, from 40 to 48, while the all-home median held at $807,500 from different middle pairs. These are small samples, 31 and 35 single-family sales and 9 and 13 villa sales, and a handful of closings can move any of these medians.
DiVosta opened pre-sales in December 2014 from a temporary sales center at Verona Walk, with base prices from $263,990 to $419,990, per its archived December 2014 page, and opened its model park on March 14, 2015, per the archived March 2015 page. By July 2019 the Serenity design started at $312,990 and the Martin Ray at $412,990, per the archived 2019 page, and by December 2020 DiVosta was marketing its single-family homes “from the $400s to $700s,” per Florida Weekly. Those were base prices before lot premiums and options. They explain why an original owner’s gain can be large, and they tell a buyer nothing about today’s value, which comes only from resales.
The calendar series is how we adjust an older comparable sale for time. A 2024 detached sale, closed at the peak, needs adjusting down to read against 2026; a 2025 sale, closed at the reset, may need adjusting up. It does not price your home by itself. For your address, the right instrument is still a comparable analysis on your product, your plat, your plan, your lot and your condition.
The record says no measurable dent. After Hurricane Ian in 2022, the district’s own minutes recorded that “No significant damage was noted by the community,” per the district’s February 2023 board meeting book, and the detached median went on to its $1,000,000 peak in 2024. FEMA’s claims data for the Census block group that contains Winding Cypress show three flood claims, all from Irma in 2017 and none paid, and none for Ian, Helene or Milton, per OpenFEMA; that block group is larger than the community.
Winding Cypress sits between Hacienda Lakes and Naples Reserve on price, with no golf and no equity club. Among five East Naples communities searched the same way in the Southwest Florida MLS for single-family homes, Winding Cypress posted the highest median sale-to-list ratio, 96.26 percent, and the longest median days on market, 76.
Data updated: September 2026 (Southwest Florida MLS, single-family closings Sept. 24, 2025 to Sept. 23, 2026, pulled 23 Sep 2026)
Each community was searched in the Southwest Florida MLS on September 23, 2026 by its own development name, one dictionary entry each, single-family homes only, sales closed in the prior 365 days, with medians computed the same way for every row. The benchmark compares seller decision variables, days on market and sale-to-list, alongside price, because those are the numbers that shape a listing strategy.
Community | Sales | Median sale | Median $ per sq ft of living area | Median living sq ft | Median days on market | Median sale-to-list | Range | Golf |
|---|---|---|---|---|---|---|---|---|
Winding Cypress | 35 | $875,000 | $405.92 | 2,158 | 76 | 96.26% | $575,000 to $1,495,000 | No |
Hacienda Lakes | 38 | $867,500 | $364.61 | 2,475 | 62 | 95.71% | $512,500 to $2,840,000 | No |
Naples Reserve | 50 | $1,372,500 | $470.78 | 2,602 | 47 | 96.21% | $580,000 to $2,400,000 | Not stated in the MLS search |
Fiddler’s Creek | 98 | $1,299,500 | $505.53 | 2,685.5 | 65 | 94.81% | $385,000 to $3,900,000 | Includes golf-membership product |
Treviso Bay | 20 | $2,062,500 | $736.68 | 2,497.5 | 25 | 94.59% | $1,050,000 to $3,100,000 | Includes golf-membership product |
Source: Southwest Florida MLS, pulled September 23, 2026. Medians from an even count are the midpoint of the two middle sales. Winding Cypress villas are left out because the comparison is detached to detached.
The two detached medians, $875,000 in Winding Cypress and $867,500 in Hacienda Lakes, sit $7,500 apart, and neither community has golf. The difference is what the money buys: the median Hacienda Lakes home that sold was larger, 2,475 square feet of living area against 2,158, at a lower $364.61 per foot against $405.92, about 10 percent less. When a Winding Cypress buyer cross-shops, this is often the pair on the table, and a seller should price knowing the buyer can get more square feet for the same money a few minutes away and is choosing Winding Cypress for newer DiVosta construction, the preserve setting and the bundled amenity program.
Naples Reserve, off US 41 east of Collier Boulevard, closed its detached homes at a median of $1,372,500, about 57 percent above Winding Cypress, at $470.78 per square foot of living area, about 16 percent more per foot, and in a median of 47 days. Its median home is larger, at 2,602 square feet. For a Winding Cypress seller, Naples Reserve matters as the ceiling a buyer can step up to: a Winding Cypress Estate plan on a preserve lot priced near the Naples Reserve median asks the buyer to give up a larger home and lake system for the same money.
Fiddler’s Creek and Treviso Bay both include golf-membership product, which Winding Cypress does not have, and they price accordingly: $505.53 and $736.68 per square foot of living area. Treviso Bay closed its detached homes in a median of just 25 days. For most Winding Cypress sellers these are the upper anchors of the East Naples market rather than direct competitors, and the buyer who decides golf inside the gates is worth the premium is a buyer who was never going to choose Winding Cypress.
Winding Cypress detached homes sell closer to their list price than any of the four peers, and they take longer to do it. The pattern in the last twelve months was patient pricing rather than fast sales: homes that sat longer but closed nearer their asking price. Its detached range, $575,000 to $1,495,000, is also the tightest of the five, because one builder in three series from 2015 to 2023 produces a more predictable market than a community of several builders or several decades. That predictability is a seller’s asset: a well-evidenced list price is easy to defend to a buyer’s agent and to an appraiser.
Winding Cypress and Verona Walk are next-door DiVosta communities on Collier Boulevard, and most Winding Cypress buyers tour both. Winding Cypress is smaller and newer, 766 homes built 2015 to 2023, and its twelve-month median sale was $807,500; Verona Walk has 1,920 homes and closed 97 sales at a median of $494,000.
Data updated: September 2026 (Southwest Florida MLS: Winding Cypress pulled 23 Sep 2026, Verona Walk trailing twelve months to 24 Sep 2026; Verona Walk CDD FY2026/27 adopted budget)
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 list of PUD ordinances and its PUD layer. DiVosta built both, taking the Verona Walk land from 2003, per the Clerk’s official records, and the two associations share part of the entry road under a Cost Sharing Agreement recorded in 2014, under which the Verona Walk association pays 31 percent of the shared road, bridge, fountain, drainage and landscaping costs. A buyer who drives in for one sees the other. Our guide to Verona Walk, the larger DiVosta community next door, covers it in full.
Yardstick | Winding Cypress | Verona Walk |
|---|---|---|
Homes | 766: 152 attached villas, 614 detached | 1,920: 944 attached, 976 detached |
Built | 2015 to 2023 (DiVosta) | DiVosta, selling from 2003 |
Age restriction | None; all-ages covenants | None; open to all ages |
Club | Clubhouse owned by the association, bundled in the assessment; no initiation | Association-owned Town Center; no club initiation |
Association assessment | $6,247.75 to $7,067.22 a year by series (2026, published) | Not published |
District assessment (FY2026/27) | $1,643.98 to $2,338.98 a year | $744.85 to $992.85 a year |
Twelve-month closings | 48 | 97 |
Median sale, all homes | $807,500 | $494,000 |
Median sale, attached | $575,000 (13 villas) | $440,000 |
Median sale, detached | $875,000 (35 homes) | $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% |
Sources: Winding Cypress, Southwest Florida MLS pulled September 23, 2026, the association’s 2026 approved budget and the district’s fiscal 2026/27 budget; Verona Walk, Southwest Florida MLS trailing twelve months to September 24, 2026 and the Verona Walk CDD’s fiscal 2026/27 adopted budget. The two MLS windows end a day apart.
The median Winding Cypress sale ran $313,500 above the median Verona Walk sale, but the gap per square foot of living area is much narrower, $394.83 against $306.19, about 29 percent. Much of the headline difference is home size and product mix: 614 of Winding Cypress’s 766 homes are detached, against about half of Verona Walk’s. Product for product, a Winding Cypress detached home sold at a median $170,000 above a Verona Walk detached home, and a Winding Cypress villa at $135,000 above a Verona Walk attached home. That product-for-product premium is what a Winding Cypress seller is defending: newer construction, a bundled clubhouse, clay courts and the preserve.
Your buyer will see that every Winding Cypress fee layer is published before an offer, while Verona Walk’s association assessment is not. Your buyer will see homes built from 2015 onward, which sit years further from the 20-year four-point inspection threshold Citizens Property Insurance applies. And your buyer will see a smaller community, 766 homes against 1,920, where a detached home or a preserve lot comes up less often. Each of those belongs in a Winding Cypress listing presentation.
Your buyer will also see a lower price of entry next door, a district assessment roughly $900 to $1,350 a year lower at each end of the two ranges, and a faster, deeper market: 97 closings, a median of 53 days on market and a 96.31 percent sale-to-list ratio. A Winding Cypress home priced above what its product premium supports sends a buyer next door. Price so the comparison does not end the conversation.
A buyer who chooses Winding Cypress wants newer DiVosta construction, a published fee stack, clay tennis and eight pickleball courts inside the gates, and a lot that may back onto recorded preserve beside the Picayune Strand State Forest, and accepts a higher district line until the 2040s. A buyer who chooses Verona Walk wants a lower entry price, a larger community with more homes to choose from, an association-owned Town Center and a smaller district line. When we price a Winding Cypress home we make the case to the first buyer directly, and we price so the second buyer’s comparison does not end the conversation. Jesse McGreevy at (239) 898-6072 will tell you which of those two buyer pools your home will actually meet.
If your buyer values most | They lean to |
|---|---|
Homes built 2015 to 2023 | Winding Cypress |
Every fee layer published before an offer | Winding Cypress |
Recorded preserve beside a state forest | Winding Cypress |
The lowest price of entry on this stretch of Collier Boulevard | Verona Walk |
A smaller district assessment | Verona Walk |
The most homes and the most sales to choose from | Verona Walk |
Winding Cypress buyers pay for a bundled amenity program, recorded preserve and an everyday map: a clubhouse with clay tennis, eight pickleball courts, a heated pool and a poolside café inside the gates, A-rated elementary and middle schools, a hospital about 3 minutes from the gate and Naples Pier about 21 minutes away without traffic.
Data updated: September 2026 (HOA 2026 Rules; FLDOE 2026 school grades; OpenStreetMap routing from the Collier Boulevard gate, no traffic)
The Club at Winding Cypress is owned by the association and paid for inside the assessment, so there is no initiation fee, no equity membership and no separate club bill, per the 2026 approved budget. DiVosta marketed a 17,500-square-foot clubhouse, per its archived 2016 page, and its contractor, DeAngelis Diamond, describes a 22,000-square-foot amenity center. The association’s 2026 Rules (final draft) list 4 Har-Tru clay tennis courts, 8 pickleball courts and 4 bocce courts, and the amenities page describes a heated resort-style pool with lap lanes, a spa, a fitness center, two dog parks, a boardwalk to a preserve overlook and the Shady Palm Café, a poolside bar and restaurant run by the association. For a seller, the point is simple: a buyer comparing Winding Cypress with a golf community sees no club bill here, and that belongs in the price conversation.
About 818 acres of the roughly 1,176 acres on the five plats are recorded preserve tracts, per the county’s parcel layer, and the 74,138-acre Picayune Strand State Forest begins about 140 meters from 7478 Winding Cypress Drive on the state’s conservation lands layer. The same forest brings prescribed-burn smoke in season and wildlife at the edges, which a buyer will ask about. A seller on a preserve lot is selling the view and should be ready to answer both questions plainly.
The school district’s own address lookup assigns every Winding Cypress address to Lely Elementary, Manatee Middle and Lely High for 2026-27, and the Florida Department of Education’s 2026 grades are A, A and B. Winding Cypress is not age-restricted, so families who shop by school zone do look here, and an A-rated elementary and middle school pair is a pricing asset for a detached home.
Destination | Miles | Minutes without traffic |
|---|---|---|
Publix, Freedom Square | 1.7 | 4 |
NCH Immediate Care Southeast | 1.7 | 3 |
Physicians Regional Medical Center, Collier Boulevard | 2.2 | 3 |
Rookery Bay Environmental Learning Center | 2.3 | 4 |
Florida SouthWestern State College, Collier Campus | 2.5 | 5 |
I-75 Exit 101 | 6.1 | 11 |
Fifth Avenue South | 9.8 | 18 |
Naples Pier | 11.1 | 21 |
Tigertail Beach, Marco Island | 11.4 | 23 |
Southwest Florida International Airport | 38.8 | 49 |
Source: OpenStreetMap routing from the Collier Boulevard gate, without traffic; January to April adds time on Collier Boulevard and US 41. The nearest public golf, Lely Resort’s Mustang and Flamingo Island courses, is about 2.6 road miles and 7 minutes from the clubhouse, per Lely Resort Golf.
Mattamy’s Summerlit, 249 home sites on 65 acres, is under way within about a mile of the district edge, per Mattamy’s newsroom, and new construction nearby is competition for a buyer who wants a brand-new home. A second Collier Costco, about 162,700 square feet at Collier Boulevard and Rattlesnake Hammock Road about 3 miles north, was targeting a fall 2026 opening, per the Marco Eagle; the opening is not confirmed. The Collier MPO’s 2050 Long Range Transportation Plan carries Collier Boulevard widening to six lanes south of Manatee Road as a cost-feasible project. A Winding Cypress resale competes with new construction on price and on finished, settled landscaping.
Online estimates miss on Winding Cypress homes because automated models read the MLS, and the MLS cannot tell a Classic Series home from an Estate Series home, cannot see the plat’s district debt level or a lot’s FEMA letter, and occasionally labels a paired villa as a single-family home. A model blending those sales describes none of them.
Data updated: September 2026 (Southwest Florida MLS, pulled 23 Sep 2026; FEMA NFHL; CDD FY2026/27 budget)
An automated valuation model estimates a home from recent nearby sales of similar size. In Winding Cypress the detached market is two products, 406 Classic homes on 50-foot homesites and 208 Estate homes on 65-foot homesites, and the MLS files both as “Single Family”. A model therefore compares a Classic home with Estate sales and an Estate home with Classic sales, and whatever sold most recently drags every estimate toward it.
The MLS building label is entered by the listing agent, and at least two Live Oak Drive homes that closed in the latest twelve months carry the “Single Family” label on the block of attached villas. A model that trusts the label puts two villa sales into the detached comparable pool, which pulls detached estimates down and villa estimates out of reach. We check the county record for each comparable before we use it.
A model reads square footage, bedrooms, lot size and year built. It cannot see whether your home has impact glass or only the original shutters, whether a pool and screen enclosure were added, whether your lanai faces preserve or a neighbour, whether your lot has its own post-2024 FEMA letter moving it to shaded Zone X, or whether your plat carries the Phase 3 district debt. In Winding Cypress each of those moves the price by more than a model’s stated margin of error.
Some estimates lean on the county’s just value. On the 2026 preliminary roll the median is $495,624 for a villa and $743,973 for a detached home, well below the MLS medians of $575,000 and $875,000. The just value is a tax figure set once a year by one method across every parcel, and it is the right tool for ranking products and the wrong tool for pricing a sale.
Treat it as a rough range, not a list price. Then ask for a written opinion of value built from recorded sales of your own product and plat, with the sources named so you can check every one. That is what the Home Valuation form at the top of this page starts, and there is no charge and no obligation.
A Winding Cypress buyer prices five carrying costs into an offer: the association assessment, the district assessment on the tax bill, the county’s solid-waste charge, property tax reset to the purchase price, and insurance driven by the flood file. At closing the buyer also pays a $1,050 resale capital contribution to the association.
Data updated: September 2026 (HOA 2026 approved budget; CDD FY2026/27 budget; 2025 Collier County tax bills; HOA 2025 audit)
Layer | Amount | Period | Source |
|---|---|---|---|
Association assessment, Estate Series | $7,067.22 for 2026, including a $484 food-and-beverage minimum | Quarterly, plus the minimum | |
Association assessment, Classic Series | $6,657.76 for 2026 | Quarterly, plus the minimum | |
Association assessment, Villa Series | $6,247.75 for 2026 | Quarterly, plus the minimum | |
District operations and maintenance | $794.98, every home | Annual, on the tax bill | |
District debt, Phases 1 and 2 | Villa $849; 50-foot $954; 65-foot $1,060 | Annual, to November 2045 | |
District debt, Phase 3 | 50-foot $1,429; 65-foot $1,544 | Annual, to November 2049 | |
Solid waste | $261.91 | Annual, on the tax bill | |
Property tax | 10.5058 mills on 2025 bills | Annual | |
Resale capital contribution | $1,050 per resale in 2025, paid by the buyer | Once, at closing |
District figures are the gross budget amounts, before the 4 percent discount for paying the tax bill in November. The 2026 association assessment went down, not up: the Estate quarterly bill fell from $1,662.31 in 2025 to $1,645.80, about 1.0 percent, which is a rare line in a Southwest Florida budget season and worth putting in front of every buyer.
Product and district area | Association 2026 | District FY2026/27 | Solid waste | Annual total (about) |
|---|---|---|---|---|
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 |
These are our sums of the published lines, before property tax, insurance and utilities: about $680 to $805 a month. A buyer sets that monthly figure beside the mortgage payment, which is why two homes at the same price but on different plats do not cost the buyer the same.
The district’s operations charge rose from $232.06 in fiscal 2022/23, per the FY2022/23 budget, to about $795 in fiscal 2023/24, and has held at $794.98 since. The driver is lake-bank repair: LJA Engineering assessed all 29 lakes in March 2024 in its lake assessment, and the fiscal 2026/27 budget carries a $300,000 lake-bank remediation line and a lake-bank reserve of $366,062 as of July 1, 2026. Show the buyer that the jump already happened and has been flat for three budget years, with the remediation carried in the regular operations charge and a lake-bank reserve rather than a special assessment.
Florida’s Save Our Homes cap follows the owner, not the house, per the Florida Department of Revenue and section 193.155 of the Florida Statutes, so a buyer’s ad valorem tax resets toward market value after the sale. As an illustration only, 10.5058 mills applied to the $875,000 median detached sale with no exemption gives about $9,192.58 a year of ad valorem tax, and applied to the county’s $743,973 median detached just value about $7,816.03. Three real 2025 bills show the full stack on paper: a homesteaded Phase 2 home at 7478 Winding Cypress Drive paid $7,724.86 in total, a non-homesteaded villa at 7666 Jacaranda Lane $6,671.25 and a non-homesteaded Phase 3 home at 6792 Bromeliad Drive $9,330.52. Those are arithmetic and history, not quotes for any home.
A valuation is a gross number, and a seller decides on the net. Florida’s documentary stamp tax on the deed is 70 cents per $100 of consideration under section 201.02 of the Florida Statutes, about $6,125 on an $875,000 sale and about $4,025 on a $575,000 villa sale (our arithmetic). Add the estoppel certificate, capped by the state at $299 plus $119 for expedited delivery under the DBPR fee schedule, the prorated association and tax lines, title and settlement charges and the brokerage fee you negotiate. We put a written net sheet beside every valuation so the decision is made on the right number.
A Winding Cypress seller owes the buyer the Florida homeowners association disclosure summary before the contract is signed, because section 720.401 of the Florida Statutes places that duty on the parcel owner in a resale, and a buyer who does not receive it may cancel. The recorded Declaration adds a 20-day notice to the association before closing.
Data updated: September 2026 (Florida Statutes as linked; Winding Cypress Amended and Restated Declaration, OR 6330 PG 3383)
The statute requires that a prospective parcel owner be presented a disclosure summary before executing the contract for sale, and on a resale the parcel owner supplies it, per section 720.401. The contract must carry the statutory voidability warning in conspicuous type. If the summary is not provided first, the buyer may void the contract within three days after receiving it or before closing, whichever comes first, and that right cannot be waived. It is a pre-contract duty, not a closing item, and getting it wrong hands the buyer an exit that survives to the closing table.
In some Naples communities a seller has to work out whether the homeowners association statute or the condominium statute governs the sale. Winding Cypress has no condominiums: every one of its 766 homes, the attached villas included, is a fee-simple home on its own platted lot inside one homeowners association, per the county’s parcel layer and the association’s Sunbiz record. Confirm the package for your own sale with your closing agent or attorney. This is general information, not legal advice.
The community’s Amended and Restated Declaration, recorded February 16, 2024 at Official Records Book 6330, Page 3383, splits the sale obligations cleanly. The selling owner notifies the association at least 20 days before closing; the association cannot disapprove a sale and records a Certificate of Approval, a sample of which sits in the Clerk’s official records. The buyer pays the resale capital contribution at closing, $1,050 per resale in 2025 according to the association’s 2025 audit, an amount the Board sets each year. The durable part is who owes what and when; the amount is the volatile part, and it prints on the estoppel certificate.
An estoppel certificate is the association’s written statement of what is owed on your parcel at closing. Under section 720.30851 of the Florida Statutes an association must deliver one within ten business days of a written request, and the current DBPR schedule caps the fee at $299, plus $119 for expedited delivery and more if the account is delinquent. Order it the week the contract is signed, not the week of closing.
Winding Cypress sits inside the Winding Cypress Community Development District, created by Collier County Ordinance 2015-48 on about 358 acres. Florida’s section 190.048 requires a disclosure to buyers of property in a community development district. We attach the district’s budget line for your product and plat so the buyer sees the exact figure rather than a range.
Since October 1, 2025, Florida requires a residential seller to disclose known flooding, flood insurance claims and federal flood assistance received on the home, under section 689.302 as explained in the Florida Senate staff analysis of HB 1049 (2024). A Winding Cypress seller with a clean claims history, an elevation certificate and, where one exists, a post-2024 FEMA letter should lead with all three.
The flood map and insurance records change a Winding Cypress price through the buyer’s monthly cost. FEMA’s map effective February 8, 2024 places every sampled address in Zone AE, base flood elevation 8.0 feet NAVD88, so most mortgaged buyers need flood cover, unless the home is one of about 15 with its own letter to shaded Zone X.
Data updated: September 2026 (FEMA National Flood Hazard Layer; Collier County Elevation Certificates layer; OpenFEMA; Citizens 2026 Rate Kit)
Between 2015 and 2019 DiVosta obtained phase-wide Letters of Map Revision based on Fill that took whole phases out of the flood zone on the older map, such as Case 15-04-9413A for Phase One and Case 19-04-5181A for Phase 3. FEMA’s own LOMR-F layer marks those letters superseded or not incorporated on the 2024 map. A listing remark written from the old letters is out of date, and a buyer’s lender will read the current map.
Since the 2024 map took effect, FEMA has issued 16 single-lot determinations covering 15 Winding Cypress homes, each moving a lot or structure to shaded Zone X, clustered on Live Oak Drive and Cocoplum Street. The most recent read for this page, Case 26-04-3737A, dated June 24, 2026, covers a Live Oak Drive lot. Every such letter says the lender “has the option to continue the flood insurance requirement”, so the letter does not guarantee a waiver; it does change the conversation and usually the quote.
Collier County’s Elevation Certificate layer holds 230 certificates on Winding Cypress streets, filed with permits from 2014 to 2019. Two certificates read in full bracket the community: 7093 Live Oak Drive at 10.10 feet NAVD88, certified in 2015, and 6920 Cocoplum Street at 9.40 feet, certified in 2019. Across the certificates reviewed, finished floors run from about 9.4 to 10.7 feet, roughly 1.4 to 2.7 feet above the 8.0-foot base flood elevation (our arithmetic). The later Phase 3 streets and Arrowhead Way do not appear in that layer, so for those homes the certificate usually sits in the builder closing package or can be requested from the county’s floodplain staff at (239) 252-2942, per the county’s 2026 Floodplain Protection Newsletter.
In the Census 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 and $1,266 for homes rated Zone X, per OpenFEMA. That block group is larger than Winding Cypress and includes other subdivisions, so these are not quotes. Unincorporated Collier County is a Class 5 community in FEMA’s Community Rating System, worth a 25 percent discount on eligible policies inside the Special Flood Hazard Area, per FEMA’s Community Status Book.
Citizens Property Insurance’s 2026 Rate Kit shows Collier County’s average homeowners multiperil premium moving from $4,531 to $4,391, down 3.1 percent, a county average rather than a quote. Citizens requires a four-point inspection only on homes more than 20 years old, a line the oldest Winding Cypress homes reach from about 2034, and its flood coverage rules require flood cover on wind policies in a Special Flood Hazard Area. A wind mitigation report on the state form, valid for up to five years under Florida OIR guidance, documents the tie-downs, tile roof and shutters or impact glass that earn premium credits.
Two Winding Cypress homes of the same plan on the same street can carry different flood and wind insurance costs for the buyer, and a buyer prices the monthly difference. A home that arrives with its elevation certificate, any FEMA letter and a current wind mitigation report in the listing file removes the most common reason a buyer pauses, and that protects the price.
What moves a Winding Cypress home’s number before listing is the evidence a buyer, a lender and an insurer will ask for: the elevation certificate and any FEMA letter, a current wind mitigation report, the district and association lines for your product and plat, and presentation that shows the upgrades a record cannot.
Data updated: September 2026 (HOA Declaration and 2026 Rules; FEMA; Florida OIR)
The file we assemble before a Winding Cypress home goes on the market holds the section 720.401 disclosure summary, the estoppel request, the district’s budget line for the home’s product and plat, the elevation certificate, any post-2024 FEMA letter, a current wind mitigation report, the seller’s flood disclosure, the roof and permit history, and the association’s sale steps. A buyer who sees all of it on day one negotiates on price and condition rather than on uncertainty.
A pool and screen enclosure, an extended lanai, impact glass, new flooring, a renovated kitchen and upgraded landscaping are the differences between two otherwise identical DiVosta plans, and none of them appears in the MLS building label or the county roll. List them, date them and attach the permits, because a buyer’s appraiser can only credit what is documented.
Buyers comparing Winding Cypress with Verona Walk or with newer communities will ask about the district line. Show the exact figure for your product and plat, the bond maturity date, and the fact that the operations charge has been flat at $794.98 for three budget years. The district’s budget also tracks owners who have prepaid their bond debt, so a payoff figure for the debt part can be obtained through the closing agent if a seller or buyer wants to compare.
The association’s certified October 2025 survey found 56.3 percent of responding households full-time and 43.7 percent part-time, per its survey results. A meaningful share of buyers is therefore buying a second home, often from out of state, and a clean, well-documented, lock-and-leave presentation widens the audience. A furniture package rarely adds its replacement cost to the price; price the home, then treat the furnishings as a negotiating asset.
Signs, including real estate signs, need Board consent or permission under the Rules, per the Declaration. Buyers and their agents enter through the association’s visitors and agents process at the Collier Boulevard gatehouse, where attendants work alongside license-plate readers and a virtual callbox, and residents can issue mobile guest passes. Registering every showing ahead of time means no buyer is turned away at the gate.
About four homes a month close in Winding Cypress, and the buyer pool swells from January to April when seasonal residents are in town. Listing with the file complete in late fall or early winter puts a home in front of that pool at its largest. Listing in summer can still work for a well-priced villa, which sold in a median of 50 days over the latest twelve months, but it asks more of the price.
A free in-person Winding Cypress valuation from McGreevy and Comisar starts with the Home Valuation form at the top of this page or a call to Jesse McGreevy at (239) 898-6072. Marc Comisar walks the home, Jesse builds the analysis from your product’s and plat’s recorded sales, and you receive a written opinion of value with sources.
A written opinion of value for your specific address, built from the recorded sales of your own product and plat, matched for plan, lot and view, adjusted for time using Winding Cypress’s own price history, with every source named. Beside it, the carrying cost picture your buyer will underwrite: the association total for your series, the district line for your plat, the solid-waste charge and the tax reset. Beside that, a net sheet. And a plain recommendation on list price and timing, including the case for waiting if the evidence says wait.
Use the Home Valuation form at the top of this page, or our free home valuation request, or call Jesse McGreevy direct at (239) 898-6072. Marc Comisar is at (239) 287-5873. There is no charge and no obligation to list. McGreevy and Comisar are Top 1% Real Estate Agents Nationally Since 2008 and the #1 Team in Southwest Florida since 2012. If you have already decided to sell, our plan for selling your home in Winding Cypress covers pricing, marketing, negotiation and the association’s sale steps in full.
Every community we value gets the same method, and the result looks different each time because the communities are different. Our Audubon Country Club home valuation prices a North Naples golf community street by street from thirty-six years of recorded deeds, where Winding Cypress is priced by series and plat from homes DiVosta first sold between 2015 and 2023. Reading one beside this page is a quick way to see why a community median is never the answer.
McGreevy and Comisar are a top-reviewed real estate team on Google, and Winding Cypress sellers can read what past clients say before they choose who values their home. The four quotes below are genuine five-star reviews in each reviewer’s own words, with no aggregate score and no star-rating widget. Read the whole set on the McGreevy and Comisar Google reviews profile.
★★★★★ “We had been on the market for several months with no offers. When we signed with Marc our house was sold in 2 weeks. He has a unique system for selling homes.” Verified Google review
A home that sits is almost always a pricing problem before it is a marketing problem, and in a Winding Cypress market where active asking prices run well above recent closings, that is the review to read twice.
★★★★★ “Their recommendation on pricing my unit was sound and proved prescient. I never questioned their integrity and found it easy to rely on their recommendations. I would work with them again in a heartbeat.” Verified Google review
★★★★★ “Marc and Jesse were amazing to work with AGAIN! We just sold our 3rd home with them and couldn’t have been happier! If we ever move again we’ll always call Jesse and Marc!” Verified Google review
★★★★★ “Jesse and his team at Domain have taken care of me, my family and my friends for many years. They have listed and sold our properties, facilitated the purchase of our properties and arranged for rentals.” Verified Google review
Jesse McGreevy and Marc Comisar are the local real estate experts behind this Winding Cypress valuation page. They co-founded Domain Realty, lead a team of agent partners across Lee and Collier County, and build every valuation from the Southwest Florida MLS, Collier County’s recorded sales and the community’s own budgets. Reach Jesse direct at (239) 898-6072.
Jesse McGreevy is a licensed Florida REALTOR and Sales Associate with Domain Realty, a co-founder of the brokerage, and one half of McGreevy and Comisar, Top 1% Real Estate Agents Nationally Since 2008. He started in Southwest Florida real estate in October 2004 and runs the pricing analysis, the recorded-document work and the association paperwork on every valuation the team writes. Reach him at (239) 898-6072 or [email protected], and read his full profile on the Jesse McGreevy agent page.
Marc Comisar is a licensed Florida REALTOR and Broker Associate with Domain Realty and the other half of McGreevy and Comisar. He runs the field side of the partnership, in the homes, at the inspections and at the closing table, and he is the one who walks your Winding Cypress home before any number is written down. Reach him at (239) 287-5873, and read his full profile on the Marc Comisar agent page.
If you are buying your next home as well as selling this one, a Florida homesteader who sells and establishes a new Florida homestead may be able to transfer accumulated Save Our Homes benefit using the Department of Revenue’s Form DR-501T, and we run both sides of that math in one conversation. Call Marc at (239) 287-5873, or start with how we represent buyers in Southwest Florida.
These are the valuation questions Winding Cypress owners in East Naples actually ask, answered from the Southwest Florida MLS, Collier County’s recorded sales, the association and district budgets, the recorded Declaration and FEMA’s flood file. Nothing here is tax or legal advice, and none of it replaces a written valuation of your specific home.
It depends first on your product, then on your series, plat, plan, lot, flood record and condition. Over the twelve months to September 23, 2026, detached homes sold at a median of $875,000 and villas at $575,000, per the Southwest Florida MLS, with individual sales from $455,000 to $1,495,000. Use the Home Valuation form at the top of this page, or call Jesse McGreevy at (239) 898-6072, for a written number on your address.
Ask for a written opinion of value built from recorded sales of your own product and plat, matched for plan, lot and view, adjusted for time with the community’s own price history and tested against the current active listings. Ask for the sources to be named. McGreevy and Comisar provide exactly that at no charge and with no obligation to list.
Because the MLS files Classic and Estate homes under one single-family label, occasionally labels a villa as a single-family home, and cannot see a lot’s FEMA letter, its district debt level or its upgrades. Whatever sold most recently pulls every automated estimate toward it.
The median over the twelve months to September 23, 2026 was $405.92 per square foot of living area for detached homes, $370.01 for villas and $394.83 across all 48 closings, per the Southwest Florida MLS. Those are living-area figures and should never be set beside a county-roll figure measured on total area under roof.
48 homes closed for $38,718,900 in the twelve months to September 23, 2026, at a median of $807,500 for all homes, $875,000 for 35 detached homes and $575,000 for 13 villas, per the Southwest Florida MLS.
Not on the latest twelve months. The detached median rose 1.7 percent, from $860,000 to $875,000, and the villa median rose 2.7 percent, from $560,000 to $575,000, although detached price per square foot slipped 2.8 percent because larger homes made up more of the sales. Both products sit below their peaks.
The detached median peaked at $1,000,000 in 2024 and the villa median at $710,000 in 2023, per the Southwest Florida MLS. In 2026 to September 23 the detached median stands at $895,000 and the villa median at $575,000.
The median was 73 days on market across the twelve months to September 23, 2026: 76 days for detached homes and 50 for villas. Days on market resets when a listing is withdrawn and relisted, so a home that took that route spent longer on the market than its final figure shows.
The median sale-to-list ratio was 95.67 percent, 96.26 percent for detached homes and 94.76 percent for villas, and 7 of 48 homes sold at or above list. The ratio is measured against the final list price, after any reductions.
Nine were active on the Southwest Florida MLS on September 23, 2026, seven detached homes at a median list price of $1,250,000 and two villas at $575,000 and $599,900, with two more under contract. Against 48 closings in twelve months that is 2.2 months of supply.
Supply is tight at 2.2 months, which favours sellers, and the detached median is recovering from the 2025 reset. Buyers still negotiate about 4 percent at the median, and active asking prices sit well above recent closings, so a correctly priced home faces little real competition and an overpriced one waits.
The median active detached list price on September 23, 2026 was $1,250,000 against a trailing median detached sale of $875,000. Asking prices describe hope and closings describe value; the next few closings will settle the gap, and a seller who prices against closings is the one whose home sells next.
Villas, at a median of 50 days on market against 76 for detached homes over the latest twelve months. Villa days on market fell from 107 in the prior twelve months.
At the median, a detached home sold for $300,000 more than a villa over the twelve months to September 23, 2026, $875,000 against $575,000, with a median of 2,158 square feet of living area against 1,554.
By the homesite width on the recorded plat, 50 feet for Classic and 65 feet for Estate, by the floor plan name in your builder documents, and by the district assessment line on your tax bill, which differs by homesite width. The MLS does not record the series.
The Estate plans are larger, 2,488 to 3,894 square feet under air, and sit on wider homesites, so they occupy the upper part of the detached range. The MLS does not separate the two, so the premium is measured case by case from matched resales rather than from a published median.
It changes what your buyer pays each year. Homes on the Phase 3 plat carry district debt of $1,429 or $1,544 a year, about $475 to $485 more than a like-width home in Phases 1 and 2, until the Series 2019 bonds retire in November 2049. Phase 3 homes are also the newest, built 2019 to 2023.
About 70 lots touch a recorded preserve tract, 40 of them in Phase One, and many others face one of the 29 district lakes. No public dataset measures the premium, so we price it from the specific resales that had one rather than from a rule of thumb.
No. The 2026 preliminary roll’s median just value is $495,624 for a villa and $743,973 for a detached home, well below the MLS medians. Just value is a tax assessment, useful for ranking homes and never a list price.
The highest closing in the four years of MLS history pulled for this page was $1,895,000, for 7513 Winding Cypress Drive on January 4, 2024. The highest in the latest twelve months was $1,495,000, for a 3,656-square-foot home at 7412 Winding Cypress Drive.
Winding Cypress Drive and Jacaranda Lane recorded 12 closings each in the latest twelve months and Live Oak Drive 10. Six streets recorded none, which says nothing about demand on streets of 10 to 29 homes.
On detached homes over the latest twelve months, Winding Cypress’s $875,000 median sits $7,500 above Hacienda Lakes and well below Naples Reserve’s $1,372,500. Its $405.92 per square foot of living area runs about 11 percent above Hacienda Lakes and about 14 percent below Naples Reserve.
Winding Cypress’s twelve-month median was $807,500 on 48 closings against Verona Walk’s $494,000 on 97, and $394.83 per square foot of living area against $306.19. Product for product, detached homes sold at $875,000 against $705,000 and attached homes at $575,000 against $440,000.
The record shows no measurable dent. The district’s minutes recorded no significant damage after Ian, and the detached median went on to its $1,000,000 peak in 2024.
Every sampled address is Zone AE on FEMA’s map effective February 8, 2024, so most mortgaged buyers need flood cover. A home with a post-2024 FEMA letter to shaded Zone X, or an elevation certificate showing a floor well above the 8.0-foot base flood elevation, presents better to the buyer’s insurer.
Often yes. Collier County holds 230 certificates on Winding Cypress streets, filed with permits from 2014 to 2019. Later Phase 3 homes and Arrowhead Way are not in that layer, so their certificate usually sits in the builder closing package.
Yes. A report on the state form documents the tie-downs, tile roof and shutters or impact glass that earn insurance credits, stays valid for up to five years, and lowers the buyer’s quote in many cases, which supports your price.
Not for Citizens, which requires one only on homes more than 20 years old; the oldest Winding Cypress homes reach that from about 2034. Some private carriers set their own rules, so a buyer’s insurer may still ask.
Before property tax and insurance, the association, district and solid-waste charges together run about $8,153.64 a year for a villa to about $9,668.11 for an Estate home on the Phase 3 plat, our sums of the published 2026 and fiscal 2026/27 lines.
Not for 2026. The Estate quarterly bill fell from $1,662.31 in 2025 to $1,645.80, about 1.0 percent lower, per the approved budget. The 2027 budget is adopted each fall.
Lake-bank repair. The district’s operations charge rose from $232.06 in fiscal 2022/23 to about $795 in fiscal 2023/24 after an engineering assessment of all 29 lakes, and it has held at $794.98 since.
Yes. The district assessment stays with the lot and appears on the buyer’s tax bill each November until the bonds retire, in November 2045 for Phases 1 and 2 and November 2049 for Phase 3; the operations part continues after that.
The buyer, at closing. It was $1,050 per resale in 2025, according to the association’s audit, and the Board sets it each year; the current amount prints on the estoppel certificate.
Not in the sense of a veto. You notify the association at least 20 days before closing, the association cannot disapprove the sale, and it records a Certificate of Approval. Leases are different and need Board approval.
Often higher, because the Save Our Homes cap follows the owner, not the house. As an illustration, 10.5058 mills on the $875,000 median detached sale with no exemption is about $9,192.58 of ad valorem tax a year; that is arithmetic, not a quote for any home.
None appears in recorded documents or the association’s public pages through September 2026. The estoppel certificate for a specific home confirms, on the day of closing, that nothing further is owed.
Known facts that materially affect value and are not readily observable, the section 720.401 association disclosure summary before the contract is signed, the community development district disclosure, and, under Florida’s flood disclosure law, known flooding, flood insurance claims and federal flood assistance.
Only with Board consent or where the Rules permit it; the Declaration covers real estate signs. Clear any sign or open-house plan with the Rules first.
Understand the rules first. Leases must run 30 days to one year, no more than three a year, with Board approval and tenant screening. That rules out short-stay income, and holding keeps the full carrying cost and the district line in play.
Some. Mattamy’s Summerlit, 249 home sites, is under way within about a mile, and a buyer who wants a brand-new home will look there. A Winding Cypress resale competes on price, finished landscaping and a working amenity program.
Rarely in full. Every home here dates from 2015 to 2023, so the work that returns is usually documentation and presentation: a wind mitigation report, clean mechanical and roof records, paint, lighting and landscaping. Impact glass and a pool are value, but they are rarely worth adding just to sell.
For a listing decision, a comparable-based valuation from an agent who knows the series and plats is the usual starting point and costs nothing. A licensed appraisal makes sense for an estate, a divorce or a date-of-death basis question. The buyer’s lender orders its own appraisal regardless.
Usually, when the list price was built from recorded sales of your own product and plat. Appraisers face the same MLS labelling limits we do, so a listing file that hands them the matched sales, with sources, helps the appraisal as much as the negotiation.
Florida’s documentary stamp tax on the deed is 70 cents per $100 of price, about $6,125 on an $875,000 sale, plus the estoppel fee, prorated charges, title and settlement costs and the brokerage fee you negotiate. We put a written net sheet beside every valuation.
Get a written valuation built from your product’s and plat’s recorded sales, gather your elevation certificate, any FEMA letter and a wind mitigation report, and decide on timing with the season and the active competition in view. Start with the Home Valuation form at the top of this page, or call Jesse McGreevy at (239) 898-6072.
Sources retrieved September 2026. Every figure on this page traces to a primary source below: the Southwest Florida MLS, Collier County’s recorded instruments, tax bills and parcel records, the Winding Cypress association and district documents, Florida Statutes, federal and state agencies, or the builder’s own published material. Nothing is drawn from a listing aggregator or from another brokerage. Southwest Florida MLS figures were pulled from Matrix on September 23, 2026 (Verona Walk on September 24, 2026) and are cited as that system rather than linked, because the MLS is a members-only database. County recorded-sale counts come from Collier County Property Appraiser records, state-qualified improved sales, newest recorded sale June 19, 2026.
Winding Cypress Homeowners Association documents
Winding Cypress Community Development District
Collier County Clerk, official records
Collier County government, tax and parcel records
Florida Statutes and state agencies
Federal flood records
Builder, news and routing
Our own assets
Every row below links the official custodian of the document, so you always see the authoritative version rather than a copy we made. We host none of these files ourselves.
Document | What it proves for a Winding Cypress valuation | Official authority |
|---|---|---|
Association 2026 Approved Budget | The published annual total for each series your buyer will pay | |
Amended and Restated Declaration | The 20-day sale notice, the Certificate of Approval, leasing, signs and the buyer’s capital contribution | |
Rules and Regulations, 2026 final draft | The amenity inventory, lake use and guest rules | |
CDD fiscal 2026/27 Final Budget | The district charge by product and plat, and the bond balances | |
CDD lake assessment, 2024 | Why the district operations charge rose in fiscal 2023/24 | |
Association 2025 audit | The $1,050 resale capital contribution and the 2025 resale count | |
2025 Reserve Study Update | How the association funds replacements without special assessments | |
Florida Statutes section 720.401 | The disclosure summary a seller owes before contract | |
Florida Statutes section 720.30851 | The ten business day estoppel deadline | |
DBPR estoppel fee schedule | The $299 cap and expedited fee | |
Florida Statutes section 193.155 | Why the seller’s tax bill is not the buyer’s | |
FEMA Map Service Center | The flood zone and any FEMA letter for one address | |
FEMA LOMR-F 26-04-3737A | What a post-2024 single-lot letter to shaded Zone X looks like | |
Elevation Certificate, 7093 Live Oak Drive | What a Winding Cypress elevation certificate records | |
Collier County 2026 Floodplain Protection Newsletter | The county’s Community Rating System class and certificate availability | |
Citizens 2026 Rate Kit | Collier County average homeowners premiums |
You reach the Winding Cypress valuation team by using the Home Valuation form at the top of this page, calling Jesse McGreevy direct at (239) 898-6072, or calling Marc Comisar at (239) 287-5873. The first conversation costs nothing, and in a market where about four homes close a month it is usually the most valuable hour a seller spends.
Jesse McGreevy: (239) 898-6072, [email protected]. Marc Comisar: (239) 287-5873. Office: 24031 S Tamiami Trl #101, Bonita Springs, FL 34134.
Jesse McGreevy (Sales Associate, SL3101296) and Marc Comisar (Broker Associate, BK3060671) are licensed Florida REALTORS® with Domain Realty; Florida real estate licensure is regulated by the Florida Real Estate Commission (FREC).
McGreevy and Comisar lead Domain Realty Group, a full-service Southwest Florida real estate team; learn more at DomainRealtyGroup.com. Read more about the team on the about McGreevy and Comisar page, and about the community on our Winding Cypress community guide. Nothing on this page is legal, tax or insurance advice. Confirm anything that affects your transaction with your closing agent, attorney, accountant or insurance professional.