Winding Cypress
Homes for Sale in Naples, FL
All 2,295 homes for sale in Naples, FL · median $439,000 · 473 homes for sale in 34114 · Collier County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Florida Gulf Coast MLS
As of November 2026, Winding Cypress in Naples, FL has 16 homes for sale and 4 pending, asking from $520,000 to $1,575,000 (median $1,045,000). Over the 12 months ending 2026-11-11, 9 recorded sales closed at a median of $815,000, $393 per square foot, a median 32 days on market, sellers accepting 96% of original asking. Homes listed or recently sold were built 2015–2022; 8 of 20 report an HOA (median $515/mo); 12 of the 20 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 $9,010 ($8,570 with the full homestead exemption).
Last 30 days in Winding Cypress: 9 new listings (median asking $969,000), 4 under contract right now. As of November 11, 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 · 8 daysTop listing
Active · 2 days
Active · 25 days
Active · 40 days
Active · 153 days
Active · 75 days
Active · 57 days
Active · 43 days
Active · 15 days
Active · 1 days
Active · 42 days
Active · 19 days
Active · 126 days
Active · 26 daysActive and pending Winding Cypress listings as of 2026-11-12, 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
🟢 Buyer-leaning market. 21.3 months of supply and 20% of the inventory already under contract give buyers above-average negotiating leverage.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Florida Gulf Coast MLS records, as of November 11, 2026. Confidence: High (20 active and pending listings, 9 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated November 12, 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 November 11, 2026): the median sale price is about $815K ($393 per sq ft over the trailing 12 months of closed sales), a median 32 days on market for closed sales, and 21.3 months of supply, a buyer-leaning market.
In ZIP 34114 (Naples), 178 homes closed in the last 12 months at a median of $545K ($311/sq ft), with a median 80 days on market. Right now 251 active and 45 pending listings put supply at about 16.9 months — a soft market. See the live ZIP 34114 housing market and the Collier County market.
County records show 42 qualified sales in Winding Cypress across 2024–2025 (28 in 2024, 14 in 2025), median $775,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Flood zones in Winding Cypress: of 12 listing addresses checked against the FEMA National Flood Hazard Layer, 100% are in an A-series high-risk zone where flood insurance is required with a federally backed mortgage. Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Naples.
Winding Cypress is a community of 496 homes in Naples, Collier County, built between 2015 and 2023 (median 2018.0), with a median living area of about 2,525 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
Winding CypressWinding CypressWinding CypressWinding CypressWinding CypressWinding CypressWinding CypressWinding 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%
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.
Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.
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 (4.5). Basis: Liquidity & Demand 21.3 months of supply; Owner Commitment 59% owner-occupied; Pricing Power 96.3% 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. 8 on record.
- 6787 Pennyroyal Dr · off market
- 6820 Winding Cypress Dr · off market
- 6844 Winding Cypress Dr · off market
- 6851 Winding Cypress Dr · off market
- 7022 Live Oak Dr · off market
- 7460 Blackberry Dr · off market
- 7666 Jacaranda Ln · off market
- 7674 Jacaranda Ln · off market
| Location | Naples, Collier County, FL · ZIP 34114 |
|---|---|
| Homes in the community | 496 (FL DOR 2025 assessment roll) |
| Years built | 2015–2023 (median 2018.0) |
| Typical living area | 2,525 sq ft (median) |
| Home types (current listings and sales) | singlefamilyresidence 75%, attached 25% |
| Sale prices, last 12 months | $815,000 median across 9 closed sales · $393 per sq ft |
| Days on market (closed sales) | 32 median |
| For sale right now | 16 active, 4 pending · median asking $1,045,000 · 21.3 months of supply |
| Owner-occupied (homestead) share | 59% |
Data as of November 11, 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 November 11, 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.
Every Home for Sale in Winding Cypress Right Now (20)
All 20 active and pending Winding Cypress listings with a detail page, newest first, refreshed twice a day from the MLS.
- 7259 Live Oak Dr · $969,000 · 3 bd / 3 ba · listed Nov 9, 2026 · listed by Royal Shell Real Estate, Inc.
- 7383 Mockingbird Ct · $1,550,000 · 4 bd / 4 ba · listed Nov 5, 2026 · listed by Compass Florida LLC
- 6932 Cocoplum St · $1,575,000 · 3 bd / 3 ba · listed Nov 1, 2026 · listed by WeichertRealtors-ParadiseHomes
- 7591 Jacaranda Ln · $539,000 · 2 bd / 2 ba · listed Oct 28, 2026 · listed by Keller Williams Marco Realty
- 7775 Winding Cypress Dr · $990,000 · 4 bd / 3 ba · listed Oct 27, 2026 · listed by William Raveis Real Estate
- 7098 Live Oak Dr · $520,000 · 3 bd / 2 ba · listed Oct 24, 2026 · listed by John R Wood Properties
- 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 · $548,000 · 2 bd / 2 ba · listed Oct 6, 2026 · listed by Florida Listing Experts LLC
- 7072 Live Oak Dr · $1,350,000 · 4 bd / 4 ba · listed Oct 1, 2026 · listed by Harborview Realty Inc
- 7670 Jacaranda Ln · $615,000 · 3 bd / 2 ba · pending · 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 · $945,000 · 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 · $1,125,000 · 5 bd / 3 ba · listed Sep 10, 2026 · listed by Anchor Real Estate
- 6907 Cocoplum St · $1,295,000 · 3 bd / 3 ba · listed Aug 28, 2026 · listed by Compass Florida LLC
- 7759 Winding Cypress Dr · $1,300,000 · 4 bd / 5 ba · pending · listed Aug 15, 2026 · listed by William Raveis Real Estate
- 7478 Winding Cypress Dr · $1,349,500 · 3 bd / 3 ba · listed Aug 13, 2026 · listed by Coldwell Banker Realty
- 7156 Live Oak Dr · $590,000 · 3 bd / 2 ba · listed Aug 13, 2026 · listed by William Raveis Real Estate
- 6727 Pennyroyal Dr · $920,000 · 3 bd / 2 ba · pending · listed Aug 13, 2026 · listed by Realty One Group MVP
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Naples guides & data
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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.
- Winding Cypress Drive (11 homes on record)
- Live Oak Drive (8 homes on record)
- Winding Cypress Drive (1 homes on record)
20% 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 (2026-11-12).
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 $10,148/yr across 40 listings here (MLS tax records, 2026-11-12). |
|---|---|
| HOA dues | Median $515/month across 9 MLS listings (most billed quarterly; 2026-11-12). 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. Flood: of 12 listing addresses checked against the FEMA flood map, 0% sit outside the high-risk zone and 100% inside one, where flood insurance is required with a federally backed mortgage. Statewide, a Zone X flood policy runs about $500-$700/yr and a high-risk zone $1,200-$2,500/yr (FEMA Risk Rating 2.0 averages, not quotes). |
| Roof and age | Median build year 2016 across 40 listings. An original roof here is about 10 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 $1,540/month (tax $846, HOA $515, insurance $179). An estimate from the sources above, not a quote.
Email me new listings in Winding Cypress
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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.
Recent Developments in Winding Cypress
Development, infrastructure, retail, and school activity affecting Winding Cypress, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated November 2026.
- October 2026Infrastructure
American Airlines to resume Naples flights with twice-daily Charlotte service
The Naples Airport Authority approved an operating agreement on Oct. 15 for nonstop CRJ-700 flights to Charlotte starting Dec. 2. Flights will use the North Road Terminal now being renovated, and the airport expects about $650,000 in annual revenue. The airport's last commercial flight was in 2017.
What it may mean for the marketScheduled commercial service returns to Naples, shortening travel for residents and visitors connecting through Charlotte. The site is about 3 miles southeast of Winding Cypress.
Source: Gulfshore Business - October 2026Infrastructure
Naples begins $8M beach renourishment with 208,000 tons of sand
Sand placement started the week of Oct. 26 along about 3.5 miles of shoreline from Doctors Pass to south of 21st Avenue. Roughly 9,450 truck trips will deliver the sand, with work expected to finish by Christmas. The beach stays open, with sections temporarily closed as crews work.
What it may mean for the marketExpect truck traffic at beach access points and short-term section closures through December, followed by a wider beach and added storm buffering for nearby streets. The site is about 4 miles south of Winding Cypress.
Source: WINK News - October 2026Retail & Dining
Paragon Theaters to open 11-screen cinema at Mercato in North Naples
Mercato's leasing agent announced on Oct. 21 that Paragon Theaters signed a lease for about 33,700 square feet on the second floor, formerly home to Alamo Drafthouse and Silverspot. The cinema is expected to open in early 2027 with premium large-format screens and in-seat dining. Paragon will keep its Pavilion location on U.S. 41 North.
What it may mean for the marketRefills a vacant entertainment space at Mercato and restores a movie option within the North Naples retail district. The project is about 5 miles north of Winding Cypress, elsewhere in Collier County.
Source: Gulfshore Business - September 2026Retail & Dining
Whole Foods confirmed as anchor of 82-acre Vitano mixed-use project in East Naples
Vitano, an 82-acre master planned development at Davis and Santa Barbara boulevards, plans 86,904 sq ft of retail including a 31,995 sq ft Whole Foods, plus 200 townhomes and 422 apartments. The PUD amendment is under county review. The developer hopes to break ground in 2027.
What it may mean for the marketWould add grocery and dining options and several hundred rental and townhome units in East Naples, with retail opening roughly 20 months after construction starts. The project is about 7 miles southeast of Winding Cypress, elsewhere in Collier County.
Source: Gulfshore Business - August 2026Schools
Diocese of Venice shows plans for church and K-12 school in Golden Gate Estates
The Diocese of Venice presented plans on 41 acres at Immokalee Road and Wilson Boulevard for a 1,250-seat church and a 200,000 sq ft K-12 school for up to 1,000 students. A land use amendment is required and construction follows a three-year capital campaign, with the school built first.
What it may mean for the marketWould add private school capacity and a community facility in the Immokalee Road growth area, several years out. The project is about 15 miles northeast of Winding Cypress, elsewhere in Collier County.
Source: Gulfshore Business - May 2026Civic
Collier County weighs buying East Naples grove site planned for 423 homes
Collier County commissioners voted on May 13, 2026 to pursue appraisals and negotiations to potentially buy the 166.63-acre former South Naples Citrus Grove at 341 Sabal Palm Road using Conservation Collier funds, rather than advance a proposed 423-home development. The board authorized preliminary assessments estimated at a few thousand dollars for appraisal and environmental review. The grove had become unproductive due to citrus greening disease.
What it may mean for the marketA potential public conservation purchase would remove a large parcel from the housing pipeline and steer its future toward preserved open land. The project is about 11 miles southeast of Winding Cypress, elsewhere in Collier County.
Source: Gulfshore Business
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.
Frequently Asked Questions
What is the median home price in Winding Cypress?
How long do homes in Winding Cypress take to sell?
Is Winding Cypress a buyer's or seller's market right now?
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What share of Winding Cypress is owner-occupied?
When were the homes in Winding Cypress built?
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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: November 12, 2026) |
| Community market stats | Florida Gulf Coast MLS closed sales, 12-month windows ending November 11, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (4 streets, ZIP 34114)) |
| Under-contract shares | Florida Gulf Coast MLS records, as of 2026-11-11 |
| Historical depth | Closed-sale records back to 2026 (9 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.
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