Windward Park
Homes for Sale in Key West, FL
All 257 homes for sale in Key West, FL · median $1,249,000 · 268 homes for sale in 33040 · Monroe County homes for sale
True comps, carrying-cost math, and listings before the portals.
Nearby homes for sale
No active listings inside WINDWARD PARK right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
As of November 2026, the MLS records 1 closed sale in Windward Park in Key West, FL, the most recent in July 2026. Across Key West as a whole, 414 homes closed in the last 12 months at a median of $1,132,500, 85 median days on market, with 268 homes for sale today. At that median and Monroe County's FY2025-26 rate of 8.816 mills, annual property tax runs about $9,980 ($9,640 with the full homestead exemption).
The market around Windward Park
Windward Park is too small for its own price trend, so here is the market around it.
In ZIP 33040, 384 homes are on the market and 12% are under contract — a slower corner of Key West.
Across Monroe County, 1,367 homes are active and 187 pending (12% under contract).
ZIP and county figures describe the wider market, not Windward Park specifically. Momentum Research analysis of MLS records.
The Windward Park buying strategy.
If we were buying in Windward Park 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 Park.
The location and the amenities are priced into every listing in Windward Park. The deal is won or lost on condition, the comps, and the renovation math.
Tools for a Windward Park 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 Park sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windward Park, 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 Park home worth?
Get a no-obligation home value based on real comparable sales in Windward Park, 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 Key West →
Data sources & freshness
| Under-contract shares | Florida Keys MLS records, as of 2026-11-10 |
| Historical depth | Closed-sale records back to 2026 (1 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 Keys 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. A Momentum agent can price yours against live local comps.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
Email me new listings in Windward Park
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Windward Park
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Windward Park will answer, and the answer is published on this page for the next buyer.
