Windward Cay
Condos for Sale in Naples, FL
All 2,295 homes for sale in Naples, FL · median $439,000 · 2,057 condos for sale in Naples · 454 homes for sale in 34112 · Collier County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Florida Gulf Coast MLS
As of November 2026, Windward Cay in Naples, FL has 4 homes for sale and 1 pending, asking from $425,000 to $1,375,000 (median $874,000). Homes listed or recently sold were built 1985–2003; 4 of 5 report an HOA (median $364/mo); 5 of the 5 geocoded homes sit in a FEMA special flood hazard zone (median elevation 7 ft).
Last 30 days in Windward Cay: 3 new listings (median asking $1,099,000), 1 under contract right now. As of November 11, 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.
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 · 3 daysTop listing
Active · 0 days
Active · 5 days
Active · 101 daysActive and pending Windward Cay listings as of 2026-11-11, 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.
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.
Figures in this note are as of July 29, 2026. The live market numbers elsewhere on this page update nightly and are newer.
The 60-Second Overview
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.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
The setting & the homes.
Aerial and on-site photos of Windward Cay. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Windward CayPhotos from Florida Gulf Coast MLS listings in Windward Cay; content deemed reliable but not guaranteed.
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
The market around Windward Cay
Windward Cay is too small for its own price trend, so here is the market around it.
Across Collier County, 5,183 homes are active and 932 pending (15% under contract).
ZIP and county figures describe the wider market, not Windward Cay specifically. Momentum Research analysis of MLS records.
Windward Cay 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 contributors.
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.
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?
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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: November 11, 2026) |
| Under-contract shares | Florida Gulf Coast MLS records, as of 2026-11-11 |
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.
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