Winding Cypress
Homes for Sale in Naples, FL
All 2,052 homes for sale in Naples, FL · median $429,000 · 442 homes for sale in 34114 · Collier County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
Photo via Florida Gulf Coast MLS
As of October 2026, Winding Cypress in Naples, FL has 12 homes for sale and 4 pending, asking from $564,900 to $1,549,000 (median $1,032,500). Over the 12 months ending 2026-09-20, 46 recorded sales closed at a median of $825,000, $397 per square foot, a median 73 days on market, sellers accepting 92% of original asking (+2% versus the prior year). Homes listed or recently sold were built 2015–2022; 5 of 16 report an HOA (median $515/mo); 7 of the 16 geocoded homes sit in a FEMA special flood hazard zone (median elevation 10 ft). At the median price and Collier County's FY2025-26 rate of 11.05 mills, annual property tax runs about $9,120 ($8,680 with the full homestead exemption).
Last 30 days in Winding Cypress: 8 new listings (median asking $1,032,500), 4 under contract right now. As of October 20, 2026, 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.
Homes For Sale Right Now in Winding Cypress
Live MLS inventory for Winding Cypress. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Winding Cypress listings as of 2026-10-20, priced high to low. 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. Tap any home to ask about it.
Winding Cypress is a newer-build community — homes here run 2015 to 2023, with a median year built of 2018 — so pricing is driven by construction age and floor plan more than by lot or location variance within the neighborhood. At a $835,000 median and $398.09 per square foot, the per-foot number tells you this is a community where finish level and living area (median 2,563 sqft) carry the price, not scarcity or bidding pressure.
A median of 76 days on market and a market heat score of 23 point to a slower, more negotiated market right now, and the year-over-year figure is down 2.1%, so this is not a moment for aggressive list-and-wait pricing. For sellers, that means condition and staging do the work; for buyers, it means there's room to negotiate on terms, and 76 days is enough runway to make a considered offer rather than rush one.
Figures in this note are as of July 29, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Winding Cypress right now
🟡 Still climbing. The trailing-12-month median ($825K) is up 2.2% from the prior 12 months ($808K).Momentum Research, record-level Florida Gulf Coast MLS closed sales, 12-month windows ending September 20. Confidence: Very High (46 and 38 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 20, 2026 · Live data: Florida Gulf Coast MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Winding Cypress market snapshot (as of September 20, 2026): the median sale price is about $825K ($397 per sq ft over the trailing 12 months of closed sales), and a median 73 days on market for closed sales. The trailing-12-month median is up 2% from the prior 12 months, computed from record-level Florida Gulf Coast MLS closed sales (46 closings in the current window).
In ZIP 34114 (Naples), 1,440 homes closed in the last 12 months at a median of $660K ($314/sq ft), up 4.8% year over year, with a median 67 days on market. Right now 561 active and 136 pending listings put supply at about 12.0 months — a buyer's market. See the live ZIP 34114 housing market and the Collier County market.
County records show 27 qualified sales in Winding Cypress across 2024–2025 (20 in 2024, 7 in 2025), median $775,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Winding Cypress is a community of 360 homes in Naples, Collier County, built between 2015 and 2022 (median 2019.0), with a median living area of about 2,520 square feet. 59% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Winding Cypress is a Naples community of newer construction, with roughly 61% of homes recorded as homesteaded, suggesting most owners here use the home as a primary residence rather than a seasonal or investment property.
The setting & the homes.
Aerial and on-site photos of Winding Cypress. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Winding CypressPhotos from Florida Gulf Coast MLS listings in Winding Cypress; content deemed reliable but not guaranteed.
Who Winding Cypress is best for.
Best for
- Buyers prioritizing newer construction (2015-2023) over an older Naples-area home
- Buyers planning to homestead the property, consistent with the roughly 61% homestead share already in the community
- Buyers comfortable with a longer, more negotiated purchase timeline given the 76-day median days-on-market
Probably not for
- Buyers who require a confirmed, established amenity package before writing an offer
- Buyers expecting a fast-moving, competitive-bid market given the current market heat score of 23
- Investors expecting rapid price appreciation, given the current year-over-year decline of 2.1%
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 20 of each year, from record-level Florida Gulf Coast MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($825K) IS the median in the snapshot above, and the move from 2025 ($808K) IS the +2.2% one-year change.
Windows contain 3 to 69 sales each (46 in the current window); every figure carries its sample size. 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. Deemed reliable but not guaranteed.
25% of homes for sale in Winding Cypress are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-10-20).
Winding Cypress Market Scorecard
Winding Cypress is currently a balanced market., a median asking price of $1,250,000, and homes go under contract in about 22 days.
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Florida Gulf Coast MLS, refreshed twice daily. Market metrics only; these describe homes for sale and recent sales, not residents.
Winding Cypress on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Florida Gulf Coast MLS. Map data © OpenStreetMap contributors.
The Winding Cypress buying strategy.
If we were buying in Winding Cypress today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Winding Cypress.
A newer-build market finding its footing
With 755 homes and construction spanning 2015 to 2023, Winding Cypress is still a relatively young community by Naples standards, which means most inventory shares a similar construction era and building code vintage — a meaningful factor for insurance and maintenance planning even if it's not something we quote a number on. The $835,000 median price and $398.09 median price per square foot together suggest a market where larger, better-finished homes pull the average up, while the spread underneath is shaped by lot type and upgrade level.
The current pace — a 76-day median days-on-market and a market heat score of 23 — puts this on the calmer end of the spectrum, not a fast-turnover market. Combined with the 49 closings in the most recent window and a slight year-over-year pullback of 2.1%, the picture is one of a market that has cooled from its earlier build-out pace and is now trading at a more measured rhythm. No community amenities are currently identified from active MLS listings, so buyers should confirm any clubhouse, gate, or recreational features directly rather than assume them from general Naples-area marketing.
The location and the amenities are priced into every listing in Winding Cypress. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Winding Cypress buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (5.7). Basis: Recent Direction +2.2% year-over-year; Owner Commitment 59% owner-occupied; Pricing Power 92.1% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a newer-build community like Winding Cypress, the real work is in comparing construction vintage, floor plan, and finish level home to home, since the neighborhood doesn't have decades of resale history to lean on. We track the day-to-day MLS data — pricing, days-on-market, and what's actually closing versus listing — so you're negotiating from the current market posture, not a stale comp or a listing agent's asking price.
Winding Cypress in 15 seconds.
Tools for a Winding Cypress buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Winding Cypress sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winding Cypress, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Winding Cypress home worth?
Get a no-obligation home value based on real comparable sales in Winding Cypress, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Recently off market in Winding Cypress
Homes in Winding Cypress that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 6 on record.
- 6787 Pennyroyal Dr · off market
- 6820 Winding Cypress Dr · off market
- 6844 Winding Cypress Dr · off market
- 7022 Live Oak Dr · off market
- 7460 Blackberry Dr · off market
- 7674 Jacaranda Ln · off market
| Location | Naples, Collier County, FL · ZIP 34114 |
|---|---|
| Homes in the community | 360 (FL DOR 2025 assessment roll) |
| Years built | 2015–2022 (median 2019.0) |
| Typical living area | 2,520 sq ft (median) |
| Home types (current listings and sales) | singlefamilyresidence 75%, attached 25% |
| Sale prices, last 12 months | $825,000 median across 46 closed sales · $397 per sq ft · +2.2% vs the prior 12 months |
| Days on market (closed sales) | 73 median |
| For sale right now | 7 active, 3 pending · median asking $1,250,000 |
| Owner-occupied (homestead) share | 59% |
Data as of September 20, 2026. 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; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Winding Cypress key facts,” movewithmomentum.com/neighborhoods/winding-cypress, data as of September 20, 2026.
Housing distress & ownership in Winding Cypress, Naples
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. 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. Deemed reliable but not guaranteed.
Just listed in Winding Cypress
The newest homes for sale in Winding Cypress right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 7700 Winding Cypress Dr $1,250,000 · 5 bd · 3 ba · 2,950 sq ft · 1 day on market Courtesy of Anchor Real Estate
- 7247 Clamshell Ln $1,549,000 · 4 bd · 4 ba · 3,656 sq ft · 2 days on market Courtesy of Real Broker, LLC
- 7072 Live Oak Dr $1,450,000 · 4 bd · 4 ba · 3,350 sq ft · 3 days on market Courtesy of Harborview Realty Inc
- 7235 Live Oak Dr $925,000 · 3 bd · 3 ba · 2,300 sq ft · 3 days on market Courtesy of Royal Shell Real Estate, Inc.
- 7670 Jacaranda Ln $615,000 · 3 bd · 2 ba · 1,594 sq ft · 11 days on market Courtesy of DomainRealty.com LLC
- 7602 Jacaranda Ln $564,900 · 2 bd · 2 ba · 1,554 sq ft · 13 days on market Courtesy of Florida Listing Experts LLC
Checked against the MLS Oct 20, 2026. All new listings in this market.
Every Home for Sale in Winding Cypress Right Now (16)
All 16 active and pending Winding Cypress listings with a detail page, newest first, refreshed twice a day from the MLS.
- 7235 Live Oak Dr · $925,000 · 3 bd / 3 ba · listed Oct 16, 2026 · listed by Royal Shell Real Estate, Inc.
- 7247 Clamshell Ln · $1,549,000 · 4 bd / 4 ba · listed Oct 9, 2026 · listed by Real Broker, LLC
- 7602 Jacaranda Ln · $564,900 · 2 bd / 2 ba · listed Oct 6, 2026 · listed by Florida Listing Experts LLC
- 7072 Live Oak Dr · $1,450,000 · 4 bd / 4 ba · listed Oct 1, 2026 · listed by Harborview Realty Inc
- 7670 Jacaranda Ln · $615,000 · 3 bd / 2 ba · listed Sep 28, 2026 · listed by DomainRealty.com LLC
- 7230 Live Oak Dr · $1,100,000 · 3 bd / 3 ba · listed Sep 25, 2026 · listed by Royal Shell Real Estate, Inc.
- 6825 Greenbriar Ct · $965,000 · 4 bd / 3 ba · listed Sep 24, 2026 · listed by Premier Sotheby's Int'l Realty
- 7564 Winding Cypress Dr · $1,030,000 · 4 bd / 2 ba · pending · listed Sep 21, 2026 · listed by Gordon Pass Realty LLC
- 7700 Winding Cypress Dr · $1,250,000 · 5 bd / 3 ba · listed Sep 10, 2026 · listed by Anchor Real Estate
- 6851 Winding Cypress Dr · $1,200,000 · 3 bd / 3 ba · pending · listed Aug 30, 2026 · listed by William Raveis Real Estate
- 6907 Cocoplum St · $1,295,000 · 3 bd / 3 ba · listed Aug 28, 2026 · listed by Compass Florida LLC
- 7156 Live Oak Dr · $590,000 · 3 bd / 2 ba · listed Aug 13, 2026 · listed by William Raveis Real Estate
- 7478 Winding Cypress Dr · $1,349,500 · 3 bd / 3 ba · listed Jul 22, 2026 · listed by Coldwell Banker Realty
- 7666 Jacaranda Ln · $575,000 · 2 bd / 2 ba · listed Jul 22, 2026 · listed by EXP Realty LLC
- 7759 Winding Cypress Dr · $1,300,000 · 4 bd / 5 ba · pending · listed Jul 22, 2026 · listed by William Raveis Real Estate
- 6727 Pennyroyal Dr · $920,000 · 3 bd / 2 ba · pending · listed Jul 22, 2026 · listed by Realty One Group MVP
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Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Live Oak Drive (6 homes on record)
- Jacaranda Lane (5 homes on record)
What it really costs to own in Winding Cypress
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| Property tax | Current owners' bills run a median of $10,143/yr across 32 listings here (MLS tax records, 2026-10-20). |
|---|---|
| HOA dues | Median $515/month across 5 MLS listings (most billed quarterly; 2026-10-20). Dues cover what the documents say they cover; ask for the budget and reserve study. |
| Home and flood insurance | The average Citizens Property Insurance premium in Collier County is $2,147/yr (2,002 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. |
| Roof and age | Median build year 2018 across 32 listings. An original roof here is about 8 years old: still inside the 15-year window Florida carriers use, but ask for the roof's permit date before you bind coverage. |
Estimated carrying cost at the median asking price, before the mortgage: about $1,539/month (tax $845, HOA $515, insurance $179). An estimate from the sources above, not a quote.
Email me new listings in Winding Cypress
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Winding Cypress
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Winding Cypress will answer, and the answer is published on this page for the next buyer.
Frequently Asked Questions
What is the median home price in Winding Cypress?
How long do homes in Winding Cypress take to sell?
How many homes are in Winding Cypress?
What share of Winding Cypress is owner-occupied?
When were the homes in Winding Cypress built?
Who is the best real estate agent for Winding Cypress?
How do I find a top Naples real estate agent who knows Winding Cypress?
Can Momentum Realty connect me with an agent for Winding Cypress?
Where is Winding Cypress, and what county is it in?
Is Winding Cypress a good place to live?
Should you buy in Winding Cypress?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Florida Gulf Coast MLS, refreshed twice daily (last: October 20, 2026) |
| Community market stats | Florida Gulf Coast MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 34114)) |
| Under-contract shares | Florida Gulf Coast MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2015 (399 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Florida Gulf Coast MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
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The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Florida Gulf Coast MLS member average and 8 days faster, and we’ll price yours against live local comps.
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More on Winding Cypress
- Home values · What homes in Winding Cypress actually sell for