Windward Park
Homes for Sale in Key West, FL
All 228 homes for sale in Key West, FL · median $1,100,000 · 227 homes for sale in 33040 · Monroe County homes for sale
True comps, carrying-cost math, and listings before the portals.
Over the 12 months ending 2026-09-20, 3 recorded sales closed at a median of $1,050,000, a median 118 days on market, sellers accepting 81% of original asking. At the median price and Monroe County's FY2025-26 rate of 8.816 mills, annual property tax runs about $9,260 ($8,910 with the full homestead exemption).
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.
The 60-Second Overview
Windward Park market snapshot (as of September 20, 2026): the median sale price is about $1.05M, and a median 118 days on market for closed sales.
In ZIP 33040 (Key West), 309 homes closed in the last 12 months at a median of $908K, down 4.3% year over year, with a median 82 days on market. See the live ZIP 33040 housing market and the Monroe County market.
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 Keys MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($1.05M) IS the median in the snapshot above.
Windows contain 0 to 5 sales each (3 in the current window); every figure carries its sample size, and thin markets swing on single closings. Listing data provided by Florida Keys MLS, Inc. Information is deemed reliable but is not guaranteed by the MLS to be accurate. Deemed reliable but not guaranteed.
15% of homes for sale in ZIP 33040 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 (2026-09-20).
Housing distress & ownership in WINDWARD PARK, Key West
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 data provided by Florida Keys MLS, Inc. Information is deemed reliable but is not guaranteed by the MLS to be accurate. Deemed reliable but not guaranteed.
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.
A closer look at the Windward Park market
Homes in Windward Park trade around a median of $1.05M, where condition and lot do more to set the final number than the asking price does.
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.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- 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 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 →
Frequently Asked Questions
What is the median home price in Windward Park?
How long do homes in Windward Park take to sell?
Who is the best real estate agent for Windward Park?
How do I find a top Key West real estate agent who knows Windward Park?
Can Momentum Realty connect me with an agent for Windward Park?
Where is Windward Park, and what county is it in?
Data sources & freshness
| Community market stats | Florida Keys MLS closed sales, 12-month windows ending September 20, 2026 |
| Under-contract shares | Florida Keys MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2000 (33 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. Momentum sells for 1.25% above the Florida Keys MLS member average and 8 days faster, and we’ll 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.
See how WINDWARD PARK fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Windward Park with Momentum Realty’s local guides.