GWYNN
Homes for Sale in Key West, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
GWYNN is a small-volume pocket of Key West real estate where the median sale price sits at $655,000 and homes are taking well over four months to find a buyer — a median days-on-market of 125.5 that signals a deliberate, patient market rather than a competitive one. With only eight closings in the measurement window, every transaction moves the needle, so the statistics describe a thin slice of activity rather than a deep, liquid pool.
The market heat score of 15 confirms what the days-on-market already suggests: sellers are not fielding multiple offers, and buyers have room to negotiate. The year-over-year price shift of -42.9 percent is striking, but in a market this small, a single outlier sale can swing the median dramatically. Read that figure as a caution flag worth investigating, not as evidence of structural collapse — and price any listing or offer accordingly.
GWYNN right now
🔴 Off the recent peak. The trailing-12-month median ($655K) is down 42.9% from the prior 12 months ($1.15M) and up 54% since 2012. With about a dozen 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 floridakeys closed sales, 12-month windows ending July 27. Confidence: Medium (8 and 9 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated July 27, 2026 · Live data: floridakeys, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
GWYNN market snapshot (as of July 27, 2026): the median sale price is about $655K, and a median 126 days on market for closed sales. The trailing-12-month median is down 43% from the prior 12 months and up 54% since 2012, computed from record-level floridakeys closed sales (8 closings in the current window).
GWYNN sits within Key West in Monroe County, part of the Florida Keys MLS feed, where inventory is constrained by geography and every available parcel carries a premium tied to the island's finite land supply. Despite that structural scarcity, the current data show a community where listings are lingering and prices have pulled back measurably over the past year, creating a window of relative buyer leverage that is unusual for this market.
Who GWYNN is best for.
Best for
- Buyers with a long hold horizon who view Key West real estate as a long-term position and are not dependent on short-term price recovery.
- Buyers with the budget and flexibility to absorb a negotiated outcome below asking — the current market posture rewards those who can move deliberately.
- Second-home buyers who intend to use the property personally and treat any future appreciation as secondary to utility.
Probably not for
- Buyers who need to resell within a year or two and require reliable liquidity — eight closings per measurement window is not a liquid market.
- Buyers counting on the year-over-year trend to reverse quickly; the data do not support a confident near-term price-recovery assumption.
- Buyers who need MLS-identified community amenities as part of their decision — none have been identified from current listings in GWYNN.
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 ($655K) IS the median in the snapshot above, and the move from 2025 ($1.15M) IS the -42.9% one-year change.
Windows contain 3 to 19 sales each (8 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 real cost & risk here
Before the list price, the Florida math the portals skip. These are Monroe County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Monroe County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
The GWYNN buying strategy.
If we were buying in GWYNN 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 GWYNN.
What the numbers actually mean in GWYNN
A median price of $655,000 on eight closings means the center of the market is well established at that level, but the spread above and below is impossible to quantify from available data. Condition, orientation, lot configuration, and proximity to water or noise all drive individual prices in ways the median cannot capture. Buyers should treat $655,000 as a reference point, not a ceiling or a floor, and commission a thorough comparative analysis before making any offer.
The since-2012 appreciation of 54 percent tells a longer story: this corridor has accumulated meaningful value over more than a decade, even as the most recent year shows a sharp correction. Whether that year-over-year decline reflects a genuine repricing or a statistical artifact of low volume is the central question any serious buyer or seller must answer before acting. The honest answer requires pulling individual sale records, not relying on aggregate medians alone.
The location and the amenities are priced into every listing in GWYNN. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in GWYNN buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (1.7). Basis: Long-Term Appreciation +54% since 2012; Recent Direction -42.9% year-over-year; Pricing Power 81.1% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a thin market like GWYNN — eight closings, a 125-day median time to contract, and a year-over-year swing that demands explanation rather than assumption — the quality of comparable-sale analysis and negotiation discipline matters more than in any high-volume suburb. Momentum Realty operates in Northeast Florida, so if you are relocating from or selling into this market, we will connect you with a vetted Keys specialist and help you evaluate what the data actually means before you commit capital. We would rather lose a deal than let a client overpay or misprice.
GWYNN 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 GWYNN 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 GWYNN sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in GWYNN, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your GWYNN home worth?
Get a no-obligation home value based on real comparable sales in GWYNN, 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 GWYNN on the map →
Frequently Asked Questions
What is the median home price in GWYNN?
How long do homes in GWYNN take to sell?
Have GWYNN home prices gone up?
Who is the best real estate agent for GWYNN?
How do I find a top Key West real estate agent who knows GWYNN?
Can Momentum Realty connect me with an agent for GWYNN?
Should you buy in GWYNN?
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 (206 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.
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 floridakeys member average and 8 days faster, and we’ll price yours against live your area comps.
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More Key West & The Florida Keys & Monroe County guides
Compare before you commit - every guide covers pricing, HOA/CDD, insurance posture, and fit. Browse all of The Florida Keys & Monroe County or the full Neighborhood Finder.