Winston Park
Homes for Sale in Key Largo, FL
All 268 homes for sale in Key Largo, FL · median $829,950 · 213 homes for sale in 33037 · 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 $650,000, a median 187 days on market, sellers accepting 92% of original asking. At the median price and Monroe County's FY2025-26 rate of 8.816 mills, annual property tax runs about $5,730 ($5,380 with the full homestead exemption).
| Location | Key Largo, Monroe County, FL · ZIP 33037 |
|---|---|
| Homes in the community | 181 (FL DOR 2025 assessment roll) |
| Years built | 1954–2023 (median 1987.0) |
| Typical living area | 1,343 sq ft (median) |
| Sale prices, last 12 months | $650,000 median across 3 closed sales |
| Days on market (closed sales) | 187 median |
| Owner-occupied (homestead) share | 40% |
Data as of September 20, 2026. Listing data provided by Florida Keys MLS, Inc. Information is deemed reliable but is not guaranteed by the MLS to be accurate; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “WINSTON PARK key facts,” movewithmomentum.com/neighborhoods/winston-park--monroe, data as of September 20, 2026.
Nearby homes for sale
No active listings inside WINSTON 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
Winston Park market snapshot (as of September 20, 2026): the median sale price is about $650K, and a median 187 days on market for closed sales.
In ZIP 33037 (Key Largo), 276 homes closed in the last 12 months at a median of $972K, up 15.7% year over year, with a median 75 days on market. See the live ZIP 33037 housing market and the Monroe County market.
County records show 6 qualified sales in WINSTON PARK across 2024–2025 (4 in 2024, 2 in 2025), median $1.38M — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Winston Park is a community of 181 homes in Key Largo, Monroe County, built between 1954 and 2023 (median 1987.0), with a median living area of about 1,343 square feet. 40% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
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 ($650K) 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.
17% of homes for sale in ZIP 33037 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 WINSTON PARK, Key Largo
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 Winston Park buying strategy.
If we were buying in Winston 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 Winston Park.
A closer look at the Winston Park market
Homes in Winston Park trade around a median of $650K, where condition and lot do more to set the final number than the asking price does.
The housing stock is 181 homes built between 1954 and 2023, and 40% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in Winston Park. 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 Winston Park 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 (6.1). Basis: Long-Term Appreciation +202% since 2012; Owner Commitment 40% owner-occupied; Pricing Power 91.5% sale-to-list. Refreshed with each data update.
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 Winston 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 Winston Park sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winston 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 Winston Park home worth?
Get a no-obligation home value based on real comparable sales in Winston 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.
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Frequently Asked Questions
What is the median home price in Winston Park?
How long do homes in Winston Park take to sell?
How many homes are in Winston Park?
What share of Winston Park is owner-occupied?
When were the homes in Winston Park built?
Have Winston Park home prices gone up?
Who is the best real estate agent for Winston Park?
How do I find a top Key Largo real estate agent who knows Winston Park?
Can Momentum Realty connect me with an agent for Winston Park?
Where is Winston 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 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (4 streets, ZIP 33037)) |
| Under-contract shares | Florida Keys MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2007 (34 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.
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See how WINSTON PARK fits the bigger picture — live prices, inventory, and Momentum Scores:
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