Winding Cypress
Homes for Sale in Naples, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
Photo via Florida Gulf Coast MLS
As of September 2026, Winding Cypress in Naples, FL has 8 homes for sale and 3 pending, asking from $575,000 to $1,400,000 (median $1,099,950). Over the 12 months ending 2026-09-12, 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 2015–2021; 5 of the 10 geocoded homes sit in a FEMA special flood hazard zone (median elevation 7 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).
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 2026-09-12, 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.
Winding Cypress right now
🟡 Off the recent peak. The trailing-12-month median ($825K) is down 1.8% from the prior 12 months ($840K).Momentum Research, record-level Florida Gulf Coast MLS closed sales, 12-month windows ending September 12. Confidence: Very High (46 and 40 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated September 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 September 12, 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 down 2% from the prior 12 months, computed from record-level Florida Gulf Coast MLS closed sales (46 closings in the current window).
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
Winding Cypress
Winding Cypress
Winding Cypress
Winding Cypress
Winding Cypress
Winding Cypress
Winding Cypress
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 12 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 ($840K) IS the -1.8% one-year change.
Windows contain 3 to 70 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.
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Collier County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Collier County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
Winding Cypress Market Scorecard
Winding Cypress is currently a thin data market. Limited supply, a median asking price of $1,099,950, and homes go under contract in about 55 days.
Typical home value in the 34114 ZIP is $516,336, about 27.3% above the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
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.
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, tiles © CARTO.
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 (5.4). Basis: Recent Direction -1.8% 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.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
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.
See homes for sale in Winding Cypress on the map →
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?
Should you buy in Winding Cypress?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near Winding Cypress with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Florida Gulf Coast MLS, refreshed twice daily (last: September 12, 2026) |
| Community market stats | Florida Gulf Coast MLS closed sales, 12-month windows ending September 12, 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 2026-09-08 |
| 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?
You just read the data. Now see what your home is worth.
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.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Winding Cypress fits the bigger picture — live prices, inventory, and Momentum Scores: