Strattons
Homes for Sale in Upper Matecumbe Key Islamorada, FL
All 25 homes for sale in Upper Matecumbe Key Islamorada, FL · median $1,495,000 · 25 homes for sale in 33036 · 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, 6 recorded sales closed at a median of $1,890,000, a median 207 days on market, sellers accepting 86% of original asking (+152% versus the prior year). At the median price and Monroe County's FY2025-26 rate of 8.816 mills, annual property tax runs about $16,660 ($16,310 with the full homestead exemption).
| Location | Upper Matecumbe Key Islamorada, Monroe County, FL · ZIP 33036 |
|---|---|
| Homes in the community | 294 (FL DOR 2025 assessment roll) |
| Years built | 1935–2024 (median 1978) |
| Typical living area | 1,888 sq ft (median) |
| Sale prices, last 12 months | $1,890,000 median across 6 closed sales · +151.8% vs the prior 12 months |
| Days on market (closed sales) | 207 median |
| Owner-occupied (homestead) share | 18% |
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, “STRATTONS key facts,” movewithmomentum.com/neighborhoods/strattons, data as of September 20, 2026.
Strattons right now
🟢 Still climbing. The trailing-12-month median ($1.89M) is up 151.8% from the prior 12 months ($751K) and up 482% 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 Florida Keys MLS closed sales, 12-month windows ending September 20. Confidence: Low (6 and 5 sales in the two windows).
What's unique here: the median sale price is about 5x the typical Monroe County sale ($1.89M vs $378K, trailing 12 months, Florida Keys MLS records).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 2, 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 STRATTONS 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
Strattons market snapshot (as of September 20, 2026): the median sale price is about $1.89M, and a median 207 days on market for closed sales. The trailing-12-month median is up 152% from the prior 12 months and up 482% since 2012, computed from record-level Florida Keys MLS closed sales (6 closings in the current window).
In ZIP 33036 (Upper Matecumbe Key Islamorada), 241 homes closed in the last 12 months at a median of $1.24M, up 20.2% year over year, with a median 97 days on market. See the live ZIP 33036 housing market and the Monroe County market.
County records show 7 qualified sales in STRATTONS across 2024–2025 (4 in 2024, 3 in 2025), median $2.85M — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Strattons is a community of 294 homes in Upper Matecumbe Key Islamorada, Monroe County, built between 1935 and 2024 (median 1978), with a median living area of about 1,888 square feet. 18% 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 ($1.89M) IS the median in the snapshot above, and the move from 2025 ($751K) IS the +151.8% one-year change.
Windows contain 3 to 16 sales each (6 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.
17% of homes for sale in ZIP 33036 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 STRATTONS, Upper Matecumbe Key Islamorada
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 Strattons buying strategy.
If we were buying in Strattons 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 Strattons.
A closer look at the Strattons market
Homes in Strattons trade around a median of $1.89M, where condition and lot do more to set the final number than the asking price does.
The trailing-12-month median up 152% year over year. Homes that do trade take a median 207 days on market, useful leverage on any listing that has lingered.
The housing stock is 294 homes built between 1935 and 2024, and 18% 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 Strattons. 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 Strattons 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 (5.6). Basis: Long-Term Appreciation +482% since 2012; Recent Direction +151.8% year-over-year; Owner Commitment 18% owner-occupied; Pricing Power 86.0% 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 Strattons 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 Strattons sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Strattons, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Strattons home worth?
Get a no-obligation home value based on real comparable sales in Strattons, 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 Upper Matecumbe Key Islamorada →
Frequently Asked Questions
What is the median home price in Strattons?
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What share of Strattons is owner-occupied?
When were the homes in Strattons built?
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Where is Strattons, and what county is it in?
Is Strattons a good place to live?
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 (5 streets, ZIP 33036)) |
| Under-contract shares | Florida Keys MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2006 (123 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 STRATTONS fits the bigger picture — live prices, inventory, and Momentum Scores:
More on Strattons
- Home values · What homes in Strattons actually sell for
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