Windward Bay
Condos for Sale in Naples, FL
All 2,163 homes for sale in Naples, FL · median $429,000 · 1,932 condos for sale in Naples · 316 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 November 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. Homes listed or recently sold were built 2001–2001; 3 of 3 report an HOA (median $461/mo). 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).
Last 30 days in Windward Bay: 1 new listing (median asking $349,000). As of November 10, 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 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 · 32 daysTop listing
Active · 3 days
Active · 236 daysActive and pending Windward Bay listings as of 2026-11-10, 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.
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.
Figures in this note are as of July 29, 2026. The live market numbers elsewhere on this page update nightly and are newer.
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).
What's unique here: the median sale price is about 49% below the typical Collier County sale ($308K vs $600K, trailing 12 months, Florida Gulf Coast MLS records).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated November 11, 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), 1,269 homes closed in the last 12 months at a median of $810K ($337/sq ft), up 2.9% year over year, with a median 62 days on market. Right now 367 active and 139 pending listings put supply at about 3.5 months — a balanced 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.
The setting & the homes.
Aerial and on-site photos of Windward Bay. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Windward BayWindward BayWindward BayPhotos from Florida Gulf Coast MLS listings in Windward Bay; content deemed reliable but not guaranteed.
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.
20% 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 (2026-11-11).
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 32 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.
Windward Bay 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 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.
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 all homes for sale in Naples →
| 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.
Housing distress & ownership in Windward Bay, 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.
Just listed in Windward Bay
The newest homes for sale in Windward Bay right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 1882 Tarpon Bay Dr S 204 $349,000 · 2 bd · 2 ba · 1,332 sq ft · listed Nov 8, 2026 Courtesy of Premier Sotheby's Int'l Realty
- 1886 Tarpon Bay Dr S 204 $349,000 · 2 bd · 2 ba · 1,332 sq ft · listed Oct 10, 2026 Courtesy of Premier Sotheby's Int'l Realty
- 1882 Tarpon Bay Dr S 101 $346,500 · 3 bd · 2 ba · 1,504 sq ft · listed Mar 20, 2026 Courtesy of Premier Sotheby's Int'l Realty
Checked against the MLS nightly. All new listings in this market.
Every Home for Sale in Windward Bay Right Now (3)
All 3 active and pending Windward Bay listings with a detail page, newest first, refreshed twice a day from the MLS.
- 1882 Tarpon Bay Dr S 204 · $349,000 · 2 bd / 2 ba · listed Nov 8, 2026 · listed by Premier Sotheby's Int'l Realty
- 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 · $346,500 · 3 bd / 2 ba · listed Aug 12, 2026 · listed by Premier Sotheby's Int'l Realty
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Recent Developments in Windward Bay
Development, infrastructure, retail, and school activity affecting Windward Bay, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated November 2026.
- October 2026Infrastructure
American Airlines to resume Naples flights with twice-daily Charlotte service
The Naples Airport Authority approved an operating agreement on Oct. 15 for nonstop CRJ-700 flights to Charlotte starting Dec. 2. Flights will use the North Road Terminal now being renovated, and the airport expects about $650,000 in annual revenue. The airport's last commercial flight was in 2017.
What it may mean for the marketScheduled commercial service returns to Naples, shortening travel for residents and visitors connecting through Charlotte. The site is about 7 miles southwest of Windward Bay.
Source: Gulfshore Business - October 2026Infrastructure
Naples begins $8M beach renourishment with 208,000 tons of sand
Sand placement started the week of Oct. 26 along about 3.5 miles of shoreline from Doctors Pass to south of 21st Avenue. Roughly 9,450 truck trips will deliver the sand, with work expected to finish by Christmas. The beach stays open, with sections temporarily closed as crews work.
What it may mean for the marketExpect truck traffic at beach access points and short-term section closures through December, followed by a wider beach and added storm buffering for nearby streets. The project is about 9 miles southwest of Windward Bay, elsewhere in Collier County.
Source: WINK News - October 2026Retail & Dining
Paragon Theaters to open 11-screen cinema at Mercato in North Naples
Mercato's leasing agent announced on Oct. 21 that Paragon Theaters signed a lease for about 33,700 square feet on the second floor, formerly home to Alamo Drafthouse and Silverspot. The cinema is expected to open in early 2027 with premium large-format screens and in-seat dining. Paragon will keep its Pavilion location on U.S. 41 North.
What it may mean for the marketRefills a vacant entertainment space at Mercato and restores a movie option within the North Naples retail district. The project is about 8 miles northwest of Windward Bay, elsewhere in Collier County.
Source: Gulfshore Business - September 2026Retail & Dining
Whole Foods confirmed as anchor of 82-acre Vitano mixed-use project in East Naples
Vitano, an 82-acre master planned development at Davis and Santa Barbara boulevards, plans 86,904 sq ft of retail including a 31,995 sq ft Whole Foods, plus 200 townhomes and 422 apartments. The PUD amendment is under county review. The developer hopes to break ground in 2027.
What it may mean for the marketWould add grocery and dining options and several hundred rental and townhome units in East Naples, with retail opening roughly 20 months after construction starts. The project is about 8 miles southwest of Windward Bay, elsewhere in Collier County.
Source: Gulfshore Business - August 2026Schools
Diocese of Venice shows plans for church and K-12 school in Golden Gate Estates
The Diocese of Venice presented plans on 41 acres at Immokalee Road and Wilson Boulevard for a 1,250-seat church and a 200,000 sq ft K-12 school for up to 1,000 students. A land use amendment is required and construction follows a three-year capital campaign, with the school built first.
What it may mean for the marketWould add private school capacity and a community facility in the Immokalee Road growth area, several years out. The project is about 10 miles northeast of Windward Bay, elsewhere in Collier County.
Source: Gulfshore Business - May 2026Civic
Collier County weighs buying East Naples grove site planned for 423 homes
Collier County commissioners voted on May 13, 2026 to pursue appraisals and negotiations to potentially buy the 166.63-acre former South Naples Citrus Grove at 341 Sabal Palm Road using Conservation Collier funds, rather than advance a proposed 423-home development. The board authorized preliminary assessments estimated at a few thousand dollars for appraisal and environmental review. The grove had become unproductive due to citrus greening disease.
What it may mean for the marketA potential public conservation purchase would remove a large parcel from the housing pipeline and steer its future toward preserved open land. The project is about 10 miles south of Windward Bay, elsewhere in Collier County.
Source: Gulfshore Business
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.
What it really costs to own in Windward Bay
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| Property tax | Current owners' bills run a median of $2,693/yr across 6 listings here (MLS tax records, 2026-11-11). |
|---|---|
| HOA dues | Median $461/month across 3 MLS listings (most billed quarterly; 2026-11-11). Dues cover what the documents say they cover; ask for the budget and reserve study. |
| Home and flood insurance | The average Citizens Property Insurance premium in Collier County is $2,147/yr (2,002 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. |
| Roof and age | Median build year 2001 across 6 listings. An original roof here would be about 25 years old; under Florida's 2022 reform (SB 2-D) carriers may require an inspection past 15 years, so budget for a roof report, and for replacement where it fails. |
Estimated carrying cost at the median asking price, before the mortgage: about $864/month (tax $224, HOA $461, insurance $179). An estimate from the sources above, not a quote.
Email me new listings in Windward Bay
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Ask an agent about Windward Bay Condos for Sale
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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?
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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: November 10, 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.
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See how Windward Bay fits the bigger picture — live prices, inventory, and Momentum Scores: