WINDWARD PARK
Homes for Sale in Key West, FL
True comps, carrying-cost math, and listings before the portals.
WINDWARD PARK sits in Key West, one of the most supply-constrained real estate markets in the country, and the median price of just over $1 million reflects that reality directly. With only three closings in the current tracking window, this is a thin market — price discovery here is driven by individual property condition, lot position, and the scarcity of available inventory far more than any broad comparable set.
A median days-on-market of 118 days is the sharpest signal this market sends right now: buyers are deliberate, financing timelines in a high-value island market can be extended, and sellers who price ahead of condition will sit. For buyers, that pace creates negotiating room that a hotter market would not allow. For sellers, it demands honest pricing from day one.
The 60-Second Overview
WINDWARD PARK market snapshot (as of July 27, 2026): the median sale price is about $1.05M, and a median 118 days on market for closed sales.
WINDWARD PARK is a small, low-turnover community in Key West — the limited transaction volume means each sale carries outsized weight in establishing value, and buyers should expect wide price variation driven by property-specific factors rather than a predictable price ladder.
Who WINDWARD PARK is best for.
Best for
- A buyer targeting Key West real estate at the $1 million threshold who can absorb an extended due-diligence and closing timeline without pressure.
- A buyer who has done Monroe County homework — flood zone, wind mitigation, insurance costs — and is buying on property merit rather than community amenities.
- A seller with a well-maintained property who can price accurately from day one and hold through a longer market time without capitulating on value.
Probably not for
- A buyer who needs confirmed community amenities or shared infrastructure as part of the purchase rationale — none are established here from current data.
- A buyer on a hard timeline who cannot accommodate a process that has historically run nearly four months to contract.
- A buyer expecting the median price to function as a reliable floor or ceiling — in a three-closing market, individual property condition will move values significantly in either direction.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending July 27 of each year, from record-level floridakeys 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 4 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.
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.
Reading a thin market in Key West
Three closings in the tracking window is a meaningful data constraint, not just a footnote. In practical terms, no two sales here are truly apples-to-apples — a renovated waterfront-oriented property and an unrenovated interior lot can both carry the WINDWARD PARK address while sitting at very different values. The median of $1,050,000 is a reference point, not a floor or ceiling, and any buyer or seller treating it as a precise market anchor is working with incomplete information.
The 118-day median time to contract also reflects the Monroe County market broadly: lender requirements on island properties, insurance underwriting complexity, and buyer due-diligence timelines around flood zone and wind mitigation all extend the path from offer to close. No community-level amenities are confirmed from current MLS data, so buyers should evaluate each listing on its own site characteristics and proximity to Key West's broader infrastructure rather than assuming shared community features.
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.
Why work with Momentum here
When a market produces three closings in a window, a brokerage that can pull comparable context from adjacent Key West neighborhoods and model condition-adjusted value is worth more than one reciting the median. Momentum brings pricing discipline to thin markets — we will tell you when a list price is supported and when it is not, and we will not let a 118-day average timeline catch a client by surprise.
WINDWARD PARK 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 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 homes for sale in WINDWARD PARK on the map →
Frequently Asked Questions
What is the median home price in WINDWARD PARK?
How long do homes in WINDWARD PARK take to sell?
Do cash buyers compete in WINDWARD PARK?
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?
Should you buy in WINDWARD PARK?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Community market stats | floridakeys closed sales, 12-month windows ending July 27, 2026 |
| 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 floridakeys 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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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 floridakeys member average and 8 days faster, and we’ll price yours against live your area comps.
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