Windward Bay
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 · 279 homes for sale in 34119 · 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 Bay in Naples, FL has 2 homes for sale. Over the 12 months ending 2026-09-20, 4 recorded sales closed at a median of $307,500, $229 per square foot, a median 94 days on market, sellers accepting 95% of original asking (-12% versus the prior year). At the median price and Collier County's FY2025-26 rate of 11.05 mills, annual property tax runs about $3,400 ($2,960 with the full homestead exemption).
| Location | Naples, Collier County, FL · ZIP 34119 |
|---|---|
| Sale prices, last 12 months | $307,500 median across 4 closed sales · $229 per sq ft · -11.5% vs the prior 12 months |
| Days on market (closed sales) | 94 median |
| For sale right now | 2 active, 0 pending · median asking $356,500 |
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 Bay key facts,” movewithmomentum.com/neighborhoods/windward-bay, data as of September 20, 2026.
Last 30 days in Windward Bay: 1 new listing (median asking $349,000). 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.
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 ($308K) is down 11.5% from the prior 12 months ($348K). 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 4 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 Bay market snapshot (as of September 20, 2026): the median sale price is about $308K ($229 per sq ft over the trailing 12 months of closed sales), and a median 95 days on market for closed sales. The trailing-12-month median is down 12% from the prior 12 months, computed from record-level Florida Gulf Coast MLS closed sales (4 closings in the current window).
In ZIP 34119 (Naples), 1,303 homes closed in the last 12 months at a median of $808K ($325/sq ft), up 2.6% year over year, with a median 62 days on market. Right now 376 active and 143 pending listings — a buyer's market. See the live ZIP 34119 housing market and the Collier County market.
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 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 ($308K) IS the median in the snapshot above, and the move from 2025 ($348K) IS the -11.5% one-year change.
Windows contain 1 to 5 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.
27% 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 (2026-09-30).
Windward Bay Market Scorecard
Windward Bay is currently a balanced market., a median asking price of $356,500, and homes go under contract in about 173 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.
Homes For Sale Right Now in Windward Bay
Live MLS inventory for Windward Bay. 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 Bay 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 Bay Right Now (2)
All 2 active and pending Windward Bay listings with a detail page, newest first, refreshed twice a day from the MLS.
- 1886 Tarpon Bay Dr S 204 · $349,000 · 2 bd / 2 ba · listed Sep 16, 2026 · listed by Premier Sotheby's Int'l Realty
- 1882 Tarpon Bay Dr S 101 · $364,000 · 3 bd / 2 ba · listed Jul 1, 2026 · listed by Premier Sotheby's Int'l Realty
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
- HOA dues reported around $461/month (about $5,532/yr) · median of 34 MLS listings, most billed quarterly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $461 per month ($5,532 a year) — the median AssociationFee across 34 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 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.
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Frequently Asked Questions
What is the median home price in Windward Bay?
How long do homes in Windward Bay take to sell?
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?
Where is Windward Bay, and what county is it in?
Should you buy in Windward Bay?
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 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 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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See how Windward Bay fits the bigger picture — live prices, inventory, and Momentum Scores:
More on Windward Bay
- Home values · What homes in Windward Bay actually sell for
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