Windward Isle
Homes for Sale in Naples, FL
All 1,839 homes for sale in Naples, FL · median $425,000 · 203 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 September 2026, Windward Isle in Naples, FL has 1 home for sale. As of September 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 2,769 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.
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.
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 2026-09-30, 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.
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 1, 2026 · listed by William Raveis Real Estate
- 6892 Leeward Way · $3,995,000 · 4 bd / 4 ba · pending · listed Jul 1, 2026 · listed by Naples Homes
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.
HOA, CDD & Fees
- HOA dues reported around $833/month (about $9,996/yr) · median of 38 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 38 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, 2026-09.
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: September 30, 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 →
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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.
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