Windward Isle
Homes for Sale in Naples, FL
All 2,052 homes for sale in Naples, FL · median $429,000 · 216 homes for sale in 34109 · Collier County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Florida Gulf Coast MLS
As of October 2026, Windward Isle in Naples, FL has 1 home for sale. As of October 2026, the MLS records 33 closed sales in Windward Isle in Naples, FL since 2015, the most recent in September 2025. Recorded prices since 2024 ran from $3,050,000 to $3,395,000 (median $3,375,000), on homes of 3,131 to 4,200 sq ft. Across Naples as a whole, 14 homes closed in the last 12 months at a median of $600,000, 74 median days on market, with 32 homes for sale today. At that median and Collier County's FY2025-26 rate of 11.05 mills, annual property tax runs about $37,300 ($36,870 with the full homestead exemption).
The market around Windward Isle
Windward Isle is too small for its own price trend, so here is the market around it.
In ZIP 34109, 244 homes are on the market and 19% are under contract — a steady corner of Naples.
Across Collier County, 4,449 homes are active and 1,017 pending (19% under contract).
ZIP and county figures describe the wider market, not Windward Isle specifically. Momentum Research analysis of MLS records.
Homes For Sale Right Now in Windward Isle
Live MLS inventory for Windward Isle. 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 Windward Isle listings as of 2026-10-19, 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.
The Windward Isle buying strategy.
If we were buying in Windward Isle 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 Windward Isle.
The location and the amenities are priced into every listing in Windward Isle. The deal is won or lost on condition, the comps, and the renovation math.
What it really costs to own in Windward IsleHomes for Sale
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 $22,394/yr across 4 listings here (MLS tax records, 2026-10-20). |
|---|---|
| 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 2020 across 4 listings. Newer roofs and current wind-mitigation features usually mean the lower end of insurance quotes. |
Email me new listings in Windward IsleHomes for Sale
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 Windward IsleHomes for Sale
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Windward IsleHomes for Sale will answer, and the answer is published on this page for the next buyer.
HOA, CDD & Fees
- HOA dues reported around $833/month (about $9,996/yr) · median of 90 MLS listings, most billed quarterly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $833 per month ($9,996 a year) — the median AssociationFee across 90 MLS records, normalised to a monthly figure; most are billed quarterly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-10.
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 Windward Isle 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 Windward Isle sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windward Isle, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Windward Isle home worth?
Get a no-obligation home value based on real comparable sales in Windward Isle, 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 all homes for sale in Naples →
Data sources & freshness
| Live listings | Florida Gulf Coast MLS, refreshed twice daily (last: October 19, 2026) |
| Under-contract shares | Florida Gulf Coast MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2015 (33 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 Windward Isle fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Windward Isle
Where is Windward Isle?
Windward Isle is a community in Naples, Collier County, Florida, ZIP 34109.
Are there homes for sale in Windward Isle right now?
Yes — 1 active and 1 pending listings as of the last feed refresh (twice daily). They are listed on this page.
Does Windward Isle have an HOA or CDD?
No HOA is on record for Windward Isle in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
Housing distress & ownership in Windward Isle, 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 Windward Isle Right Now (2)
All 2 active and pending Windward Isle listings with a detail page, newest first, refreshed twice a day from the MLS.
- 6830 Mangrove Ave · $3,995,000 · 4 bd / 6 ba · listed Jul 22, 2026 · listed by William Raveis Real Estate
- 6892 Leeward Way · $3,995,000 · 4 bd / 4 ba · pending · listed Jul 22, 2026 · listed by Naples Homes
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Nearby Communities
Explore more neighborhoods near Windward Isle with Momentum Realty’s local guides.
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.