Momentum Housing Data · Home Values · Collier County
Winding Cypress (Naples, FL): 49 recorded closings in the 12 months ending 2026-07-29, an 11-year price record, and sales split by price band and home size — every number from recorded MLS closings, none from an estimate model.
In the current window, sellers accepted a median 92.0% of original asking; the median sale took 76 days (window ending 2026-07-29).
| Year | Median sold | Median $/sqft | Median DOM | Sold ÷ original ask | Sales |
|---|---|---|---|---|---|
| 2026 | $835,000 | $398 | 76 | 92.0% | 49 |
| 2025 | $852,500 | $409 | 68 | 90.7% | 38 |
| 2024 | $847,500 | $412 | 41 | 96.0% | 42 |
| 2023 | $900,000 | $446 | 31 | 97.2% | 31 |
| 2022 | $669,950 | $393 | 13 | 100.0% | 38 |
| 2021 | $527,500 | $267 | 21 | 97.7% | 72 |
| 2020 | $500,000 | $252 | 58 | 96.4% | 33 |
| 2019 | $413,000 | $239 | 73 | 96.3% | 33 |
| 2018 | $378,040 | $221 | 84 | 95.1% | 20 |
| 2017 | $437,500 | $231 | 89 | 96.9% | 22 |
| 2016 | $317,390 | $205 | 58 | 97.6% | 17 |
Over the recorded series, Winding Cypress’s median sold price moved from $317,390 (2016) to $835,000 (12 months ending 2026-07-29) — +163% over that span, with every year’s figure from recorded closings, not a model.
The recorded series starts in 2016 at $317,390. The 2020–22 run-up did what it did everywhere — Winding Cypress’s median moved +62% from 2019 to 2022. Against the 2023 peak of $900,000, the current median stands at -7%. Annual sales volume here has ranged from 0 to 72 closings a year (10-yr average 37.8).
What actually trades here: 64% single-family residence, 35% attached, 1% duplex, with a median of 2,084 sq ft and a median price per square foot of $398 in the current window.
Of the 116 recorded Winding Cypress closings since 2024, half landed between $638,750 and $993,125 (the middle two quartiles); the lowest recorded sale was $453,000 and the highest $1,895,000. If your home sits outside the middle band, the reason usually shows up in the size table below before it shows up in condition.
| Sold price band | Share of closings | Sales |
|---|---|---|
| Under $550,000 | 10 (9%) | |
| $550,000 – $783,333 | 40 (34%) | |
| $783,333 – $1,016,667 | 42 (36%) | |
| $1,016,667 – $1,250,000 | 12 (10%) | |
| None and up | 12 (10%) |
The same recorded closings, split into thirds by living area. Find the row your home falls in: the $/sqft figure times your square footage is the recorded-sales bracket for homes like yours here — a starting range from real closings, not a valuation of your specific property. Larger homes here have been selling at a higher price per square foot than smaller ones ($397 vs $388) — less common, and usually a sign of newer or upgraded product at the top of the range.
| Size group | Median $/sqft | Median sold | Sold range | Sales |
|---|---|---|---|---|
| Smaller homes 1,542–1,685 sq ft | $388 | $600,000 | $453,000 – $749,900 | 38 |
| Mid-size homes 1,685–2,186 sq ft | $433 | $885,000 | $645,000 – $1,200,000 | 38 |
| Larger homes 2,188–3,656 sq ft | $397 | $1,000,000 | $625,000 – $1,895,000 | 40 |
From the live MLS feed as of 2026-09-02: 9 active listings (plus 2 pending) asking from $575,000 to $1,400,000, median $949,900; 3 of 9 have been on the market over 60 days (median 43 days so far); the homes listed or recently sold were built between 2015 and 2022 (median 2020); 5 of 11 geocoded listed or recently sold homes sit inside a FEMA special flood hazard zone (A/V), which buyers’ lenders will price into insurance; median elevation 5 ft. For a seller this is the competition a buyer will tour alongside your home; for a buyer, the stale share is where negotiating room usually is. See the current Winding Cypress listings →
At Winding Cypress’s $835,000 median and Collier County’s adopted 11.05 mills (FY2025-26), a home assessed at that price carries roughly $9,230 a year in property tax before exemptions, or about $8,790 with the full Florida homestead exemption — a buyer’s first-year figure; a long-time owner’s Save Our Homes cap can be far lower, which is one reason resale taxes jump at closing. Municipal and special-district millage varies inside the county; see the Collier County tax page.
Momentum’s market-heat index for Winding Cypress reads 23/100 (computed from DOM, sale-to-list, and absorption; 2020–21 peaked in the 70s here).
Cash bought 69% of recorded Winding Cypress sales in the window ending 2026-07 (34 of 49) — a fact worth knowing before assuming every buyer needs an appraisal to close. The table above is the closed-sale record to price a Winding Cypress home against; asking prices are an opening position, recorded closings are the value.
We don’t publish algorithm guesses for specific homes — they can’t see condition, upgrades, or your lot. A local agent will prepare a records-based valuation from the same closed-sale data on this page, adjusted for your home. Free, no obligation.
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Communities buyers shopping Winding Cypress are also weighing (nearest by map distance), each on its own recorded 12-month closings. A median well above the neighbors is a ceiling to price against; well below is where the value argument lives.
| Community | Median sold | Median $/sqft | Median DOM | Sales |
|---|---|---|---|---|
| Falling Waters Beach Resort | $360,000 | $266 | 28 | 17 |
| Henderson Creek Park | $280,000 | $232 | 112 | 5 |
| Holiday Manor | $112,500 | $153 | 89 | 7 |
| Enchanting Shores | $140,500 | $118 | 38 | 14 |
More Winding Cypress: full community guide & homes for sale · choosing an agent here · should you sell now (statewide data) · what selling costs · cash offer vs. listing
Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate. Compiled from recorded MLS closings; deemed reliable but not guaranteed. Figures are medians for the stated windows and change as new sales record; individual homes vary widely. No automated valuation for any specific property appears on this page. Equal Housing Opportunity. © 2026 Move With Momentum LLC — brokerage licensed in FL and GA. Disclosures
Content on this page is compiled from public records, MLS data, and automated data sources, and may contain errors or be out of date. It is provided for general information only and is not a representation about any specific property, community, builder, or association. Verify all information independently before relying on it.