Windward Bay
Homes for Sale in Naples, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
Windward Bay is pricing at a median of $315,000, with price per square foot at $235.99 — both numbers reflecting a market that has cooled over the past year, with the year-over-year read down 10.0%. That kind of pullback, paired with a median days-on-market of 105, tells you sellers here are not commanding quick action. Buyers have room to negotiate on price and terms.
The closings sample behind this snapshot is thin — five recorded closings — so treat the median and per-square-foot figures as directional rather than exact. A market heat score of 14 puts this firmly on the slow side: listings are sitting, and sellers who price against last year's numbers instead of this year's will keep sitting too.
Windward Bay right now
🔴 Off the recent peak. The trailing-12-month median ($315K) is down 10.0% from the prior 12 months ($350K). 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 fgc closed sales, 12-month windows ending July 29. Confidence: Low (5 and 3 sales in the two windows).
What's unique here: the median sale price is about 49% below the typical Collier County sale ($315K vs $619K, trailing 12 months, fgc records).
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Updated July 29, 2026 · Live data: fgc, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Windward Bay market snapshot (as of July 29, 2026): the median sale price is about $315K ($236 per sq ft over the trailing 12 months of closed sales), and a median 105 days on market for closed sales. The trailing-12-month median is down 10% from the prior 12 months, computed from record-level fgc closed sales (5 closings in the current window).
Windward Bay sits in Naples, Collier County, in a market segment currently defined more by patience than urgency — the kind of environment where a well-priced home stands out simply by not overreaching.
Who Windward Bay is best for.
Best for
- Buyers comfortable negotiating in a market that currently favors them on price and timeline
- Buyers working with a longer purchase timeline who can wait through a slower-moving process
- Buyers focused on the property itself, since no shared community amenities are currently identified
Probably not for
- Sellers expecting a quick sale near or above last year's pricing levels
- Buyers who want confirmed on-site amenities as part of the purchase decision
- Anyone relying on a single data point rather than a current, property-specific market analysis given the limited closings sample
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 ($315K) IS the median in the snapshot above, and the move from 2025 ($350K) IS the -10.0% one-year change.
Windows contain 1 to 6 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.
0% of homes for sale in ZIP 34119 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 (2026-07-18).
The Windward Bay buying strategy.
If we were buying in Windward Bay 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 Bay.
A market correcting in real time
The 10.0% year-over-year decline at Windward Bay is not a blip — combined with a 105-day median time on market, it signals a community where buyer leverage has grown over the past several closing cycles. Homes that would have moved quickly a year or two ago are now sitting through multiple price conversations before closing.
No community amenities are currently identified from active MLS listings, so any comparison between homes here should rest on the property itself — condition, layout, lot — rather than assumed shared features. With only five closings behind the current snapshot, buyers and sellers alike should treat any single data point as a starting reference, not a verdict, and lean on a current comparative market analysis before setting expectations.
The location and the amenities are priced into every listing in Windward Bay. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a thin-data, slow-moving market like this one, pricing strategy matters more than usual — a listing priced off last year's comps will sit past the 105-day median with no guarantee of catching up. We pull current, hyperlocal figures rather than relying on stale averages, and we tell sellers plainly when a price needs to move to compete, and tell buyers plainly when a listing has room to negotiate.
Windward Bay 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 Bay 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 Bay sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windward Bay, 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 Bay home worth?
Get a no-obligation home value based on real comparable sales in Windward Bay, 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 Bay on the map →
Frequently Asked Questions
What is the median home price in Windward Bay?
How long do homes in Windward Bay take to sell?
Do cash buyers compete in Windward Bay?
Who is the best real estate agent for Windward Bay?
How do I find a top Naples real estate agent who knows Windward Bay?
Can Momentum Realty connect me with an agent for Windward Bay?
Should you buy in Windward Bay?
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 2014 (44 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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