Windward Cay
Homes for Sale in Naples, FL
True comps, carrying-cost math, and listings before the portals.
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.
The 60-Second Overview
Windward Cay market snapshot (as of July 29, 2026): the median sale price is about $725K ($456 per sq ft over the trailing 12 months of closed sales), and a median 67 days on market for closed sales.
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 July 29 of each year, from record-level fgc closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($725K) IS the median in the snapshot above.
Windows contain 0 to 8 sales each (5 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.
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
- Mandatory HOA — confirm current dues
- 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 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 homes for sale in Windward Cay on the map →
Frequently Asked Questions
What is the median home price in Windward Cay?
How long do homes in Windward Cay take to sell?
Do cash buyers compete in Windward Cay?
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?
Should you buy in Windward Cay?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Community market stats | fgc closed sales, 12-month windows ending July 29, 2026 |
| Under-contract shares | fgc records, as of 2026-07-18 |
| 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 fgc 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 fgc member average and 8 days faster, and we’ll price yours against live your area comps.
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