Windward Cay
Homes for Sale in Naples, FL
All 1,839 homes for sale in Naples, FL · median $425,000 · 1,649 condos for sale in Naples · 338 homes for sale in 34102 · 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 September 2026, Windward Cay in Naples, FL has 2 homes for sale. Over the 12 months ending 2026-09-20, 4 recorded sales closed at a median of $695,000, $393 per square foot, a median 91 days on market, sellers accepting 91% of original asking (-5% versus the prior year). At the median price and Collier County's FY2025-26 rate of 11.05 mills, annual property tax runs about $7,680 ($7,250 with the full homestead exemption).
| Location | Naples, Collier County, FL · ZIP 34102, 34112 |
|---|---|
| Sale prices, last 12 months | $695,000 median across 4 closed sales · $393 per sq ft · -4.8% vs the prior 12 months |
| Days on market (closed sales) | 91 median |
| For sale right now | 2 active, 0 pending · median asking $900,000 |
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. Market figures describe homes, not residents. Cite as: Momentum Realty, “Windward Cay key facts,” movewithmomentum.com/neighborhoods/windward-cay, data as of September 20, 2026.
Last 30 days in Windward Cay: 2 new listings (median asking $900,000). As of September 29, 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.
With only five closings feeding this snapshot, Windward Cay's numbers should be read as a directional signal rather than a statistically deep trend. The median sale price of $725,000 and a median price per square foot of $456.26 point to a market where individual home condition and finish level are doing most of the work in setting price, not a uniform product line.
A median of 67 days on market is on the longer side, which tells buyers there is room to negotiate and tells sellers that pricing needs to be tight from day one rather than aspirational. In a low-volume market like this, an overpriced listing sits, and a well-priced one still may take time simply because there are fewer comparable buyers moving through at once.
Windward Cay right now
🟡 Off the recent peak. The trailing-12-month median ($695K) is down 4.8% from the prior 12 months ($730K). With about 4 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Florida Gulf Coast MLS closed sales, 12-month windows ending September 20. Confidence: Low (4 and 3 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 30, 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
Windward Cay market snapshot (as of September 20, 2026): the median sale price is about $695K ($393 per sq ft over the trailing 12 months of closed sales), and a median 91 days on market for closed sales. The trailing-12-month median is down 5% from the prior 12 months, computed from record-level Florida Gulf Coast MLS closed sales (4 closings in the current window).
Florida Gulf Coast MLS sales records identify 5 homes in Windward Cay that have changed hands since 2013, built between 1989 and 2003 (median 2003), with a median living area of about 2,178 sq ft and a typical 3-bedroom, 3-bath layout; 80% are condominiums. Source: Florida Gulf Coast MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
In ZIP 34102 (Naples), 1,157 homes closed in the last 12 months at a median of $570K ($327/sq ft), up 3.3% year over year, with a median 69 days on market. Right now 606 active and 131 pending listings — a buyer's market. See the live ZIP 34102 housing market and the Collier County market.
Windward Cay is a Naples community where recent activity has been light, so pricing here reflects a handful of transactions rather than a broad, continuously refreshed market.
Who Windward Cay is best for.
Best for
- Buyers targeting a purchase near the $725,000 median who are comfortable with a slower, 67-day-plus negotiation timeline
- Buyers who want an agent to build out comparable data manually given the thin recent-sales record
- Sellers with a well-maintained, competitively priced home willing to allow adequate market time to find the right buyer
Probably not for
- Buyers who want a large pool of recent comparable sales to validate pricing before writing an offer
- Sellers expecting a fast, high-competition sale timeline based on broader Naples market pace
- Buyers relying on listed community amenities as a primary decision factor, since none are currently identified in MLS data
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 ($695K) IS the median in the snapshot above, and the move from 2025 ($730K) IS the -4.8% one-year change.
Windows contain 0 to 9 sales each (4 in the current window); every figure carries its sample size, and thin markets swing on single closings. 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.
18% of homes for sale in ZIP 34112 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 (2026-09-28).
Windward Cay Market Scorecard
Windward Cay is currently a balanced market., a median asking price of $900,000, and homes go under contract in about 27 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.
Housing distress & ownership in Windward Cay, 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 Cay
Live MLS inventory for Windward Cay. 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 Cay 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 Cay Right Now (2)
All 2 active and pending Windward Cay listings with a detail page, newest first, refreshed twice a day from the MLS.
- 4700 Yacht Harbor Dr 622 · $1,375,000 · 3 bd / 3 ba · listed Sep 7, 2026 · listed by Homeinc Realty LLC
- 4700 Yacht Harbor Dr 612 · $425,000 · 3 bd / 2 ba · listed Aug 14, 2026 · listed by KW Elevate Luxury
The Windward Cay buying strategy.
If we were buying in Windward Cay 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 Cay.
A market defined by low volume
The closings window of five sales means every transaction carries outsized weight in the median figures. A single higher-end or heavily updated home closing can shift the median price or price per square foot noticeably, which is worth remembering when comparing Windward Cay to communities with dozens of recent sales.
Current MLS listings do not identify specific community amenities for Windward Cay. That is a note about available listing data at this snapshot, not a statement that the community lacks features — buyers should confirm any amenities, association details, or common facilities directly with listing agents or HOA documentation rather than assuming based on this absence.
The location and the amenities are priced into every listing in Windward Cay. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a low-inventory, low-closing-count market like Windward Cay, pricing a home or evaluating an offer requires pulling context beyond the community itself — nearby comparable sales, condition adjustments, and a realistic read on how 67 days of market time affects negotiating leverage. That is the kind of analysis we build into every conversation here, rather than leaning on a thin set of internal comps alone.
Windward Cay in 15 seconds.
HOA, CDD & Fees
- HOA dues reported around $837/month (about $10,044/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 $837 per month ($10,044 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 Cay 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 Cay sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windward Cay, 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 Cay home worth?
Get a no-obligation home value based on real comparable sales in Windward Cay, 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 →
Frequently Asked Questions
What is the median home price in Windward Cay?
How long do homes in Windward Cay take to sell?
Who is the best real estate agent for Windward Cay?
How do I find a top Naples real estate agent who knows Windward Cay?
Can Momentum Realty connect me with an agent for Windward Cay?
Where is Windward Cay, and what county is it in?
Should you buy in Windward Cay?
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: September 30, 2026) |
| Community market stats | Florida Gulf Coast MLS closed sales, 12-month windows ending September 20, 2026 |
| Under-contract shares | Florida Gulf Coast MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2013 (54 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 Cay fits the bigger picture — live prices, inventory, and Momentum Scores:
More on Windward Cay
- Home values · What homes in Windward Cay actually sell for
Nearby Communities
Explore more neighborhoods near Windward Cay with Momentum Realty’s local guides.