Winston Waterway
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.
Market Heat
Over the 12 months ending 2026-09-20, 3 recorded sales closed at a median of $1,200,000, a median 29 days on market, sellers accepting 97% of original asking (-7% versus the prior year). At the median price and Monroe County's FY2025-26 rate of 8.816 mills, annual property tax runs about $10,580 ($10,230 with the full homestead exemption).
| Location | Key Largo, Monroe County, FL · ZIP 33037 |
|---|---|
| Homes in the community | 432 (FL DOR 2025 assessment roll) |
| Years built | 1955–2024 (median 1986.0) |
| Typical living area | 1,288 sq ft (median) |
| Sale prices, last 12 months | $1,200,000 median across 3 closed sales · -7.2% vs the prior 12 months |
| Days on market (closed sales) | 29 median |
| Owner-occupied (homestead) share | 42% |
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 WATERWAY key facts,” movewithmomentum.com/neighborhoods/winston-waterway, data as of September 20, 2026.
Winston Waterway right now
🟡 Off the recent peak. The trailing-12-month median ($1.20M) is down 7.2% from the prior 12 months ($1.29M) and up 238% since 2012. With about 6 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 Florida Keys MLS closed sales, 12-month windows ending September 20. Confidence: Low (3 and 4 sales in the two windows).
What's unique here: the median sale price is about 3x the typical Monroe County sale ($1.20M vs $378K, trailing 12 months, Florida Keys MLS records).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 21, 2026 · Live data: Florida Keys MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
Nearby homes for sale
No active listings inside WINSTON WATERWAY 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 Waterway market snapshot (as of September 20, 2026): the median sale price is about $1.20M, and a median 29 days on market for closed sales. The trailing-12-month median is down 7% from the prior 12 months and up 238% since 2012, computed from record-level Florida Keys MLS closed sales (3 closings in the current window).
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 24 qualified sales in WINSTON WATERWAY across 2024–2025 (16 in 2024, 8 in 2025), median $885,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Winston Waterway is a community of 432 homes in Key Largo, Monroe County, built between 1955 and 2024 (median 1986.0), with a median living area of about 1,288 square feet. 42% 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 ($1.20M) IS the median in the snapshot above, and the move from 2025 ($1.29M) IS the -7.2% one-year change.
Windows contain 3 to 12 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 WATERWAY, 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 Waterway buying strategy.
If we were buying in Winston Waterway 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 Waterway.
A closer look at the Winston Waterway market
Homes in Winston Waterway trade around a median of $1.20M, where condition and lot do more to set the final number than the asking price does.
The trailing-12-month median down 7% year over year. Homes that do trade take a median 29 days on market, useful leverage on any listing that has lingered.
The housing stock is 432 homes built between 1955 and 2024, and 42% 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 Waterway. 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 Waterway 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 4 factors (6.7). Basis: Long-Term Appreciation +238% since 2012; Recent Direction -7.2% year-over-year; Owner Commitment 42% owner-occupied; Pricing Power 97.4% 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 Waterway 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 Waterway sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winston Waterway, 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 Waterway home worth?
Get a no-obligation home value based on real comparable sales in Winston Waterway, 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 Waterway?
How long do homes in Winston Waterway take to sell?
How many homes are in Winston Waterway?
What share of Winston Waterway is owner-occupied?
When were the homes in Winston Waterway built?
Have Winston Waterway home prices gone up?
Who is the best real estate agent for Winston Waterway?
How do I find a top Key Largo real estate agent who knows Winston Waterway?
Can Momentum Realty connect me with an agent for Winston Waterway?
Where is Winston Waterway, 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 (11 streets, ZIP 33037)) |
| Under-contract shares | Florida Keys MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2006 (111 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 WATERWAY fits the bigger picture — live prices, inventory, and Momentum Scores:
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