Homes for Sale in Upper Matecumbe Key Islamorada, FL
24 homes are for sale in Upper Matecumbe Key Islamorada, FL as of 2026-09-25, with 3 more under contract. The median list price is $1,400,000, most homes list between $550K to $13.75M, and the median listing has been on the market 176 days. That is 16 houses, 8 condos and 0 townhouses. 0 homes came on the market this week.
| Location | Monroe County, FL |
|---|---|
| ZIP codes with their own page | 1 |
| For sale right now | 24 active, 3 under contract |
| Asking prices | $1,400,000, median · most homes $550K–$13.75M |
| Median days on market (active listings) | 176 |
| Property types for sale | 16 houses, 8 condos, 0 townhouses |
| New listings this week | 0 |
Listing counts and prices as of 2026-09-25; MLS data, refreshed nightly. Market figures describe homes, not residents. Cite as: Momentum Realty, “Upper Matecumbe Key Islamorada, FL key facts,” movewithmomentum.com/homes-for-sale/upper-matecumbe-key-islamorada-fl/, data as of 2026-09-25.
Newest homes for sale in Upper Matecumbe Key Islamorada
The most recently listed homes in Upper Matecumbe Key Islamorada, newest first, with photos. Each card opens the full listing with every photo, the community’s sales history and a tour request. Homes marked New listed in the last seven days.
Upper Matecumbe Key Islamorada homes for sale by price
Every active listing in Upper Matecumbe Key Islamorada grouped by price, with the newest listings in each band. The median is $1,400,000; the busiest band is $1M and up.
$500K – $750K: 8 homes
- $549,500 · 1 bd / 1 ba · 81801 Overseas Highway #716
- $549,500 · 1 bd / 1 ba · 81801 Overseas Highway #715
- $649,000 · 1 bd / 1 ba · 81801 Old Highway #754
- $715,000 · 1 bd / 1 ba · 81801 Overseas Highway #637
$750K – $1M: 1 home
$1M and up: 15 homes
- $2.29M · 4 bd / 3 ba · 81250 Overseas Highway # 5
- $4.75M · 4 bd / 4.5 ba · 82779 Old Highway #1
- $2.48M · 3 bd / 3 ba · 81250 Overseas Highway #2
- $13.75M · 5 bd / 6 ba · 19 Avacado Street
Every home for sale in Upper Matecumbe Key Islamorada right now (24)
All 24 active Upper Matecumbe Key Islamorada listings with a detail page, newest first, refreshed twice a day from the MLS.
- $2.29M · 4 bd / 3 ba · 81250 Overseas Highway # 5
- $4.75M · 4 bd / 4.5 ba · 82779 Old Highway #1
- $2.48M · 3 bd / 3 ba · 81250 Overseas Highway #2
- $549,500 · 1 bd / 1 ba · 81801 Overseas Highway #716
- $549,500 · 1 bd / 1 ba · 81801 Overseas Highway #715
- $649,000 · 1 bd / 1 ba · 81801 Old Highway #754
- $13.75M · 5 bd / 6 ba · 19 Avacado Street
- $1.20M · 3 bd / 3 ba · 143 N Hammock Road
- $715,000 · 1 bd / 1 ba · 81801 Overseas Highway #637
- $550,000 · 2 bd / 2 ba · 80450 Overseas Highway #204
- $699,000 · 1 bd / 1 ba · 81801 Overseas Highway ## 729
- $585,000 · 1 bd / 1 ba · 81801 Overseas Highway #727
- $789,000 · 3 bd / 2 ba · 124 S Hammock Road
- $4.00M · 4 bd / 4.5 ba · 82779 Old Highway #7
- $4.00M · 4 bd / 4.5 ba · 82779 Old Highway #8
- $3.80M · 4 bd / 4.5 ba · 82779 Old Highway #15
- $15.95M · 6 bd / 7.5 ba · 20 Avacado Street
- $550,000 · 2 bd / 2.5 ba · 80450 Overseas Highway #APT 106
- $22.50M · 7 bd / 8 ba · 81486 Overseas Highway
- $3.95M · 4 bd / 4.5 ba · 82779 Old Highway #14
- $2.50M · 3 bd / 3.5 ba · 81906 Overseas Highway #2
- $1.25M · 3 bd / 3 ba · 189 Carroll Street
- $1.25M · 3 bd / 3 ba · 191 Carroll Street
- $1.55M · 4 bd / 3 ba · 36 Park Road
Homes for sale in Upper Matecumbe Key Islamorada by ZIP code
Where the inventory is: active listings and the median asking price by ZIP. ZIPs link to their housing scorecard.
| ZIP | Homes for sale | Median list price |
|---|---|---|
| 33036 | 24 | $1.40M |
What is for sale in Upper Matecumbe Key Islamorada: property types
- Single-family houses: 16
- Condos: 8
Browse by type: Condos for sale in Upper Matecumbe Key Islamorada (8).
What a home in Upper Matecumbe Key Islamorada costs to own
Take the median $1,400,000 listing with 20% down at today’s 6.95% 30-year rate: principal and interest run about $7,414/month. Monroe County’s typical millage of 8.82 puts property tax near $11,902/year after the $50,000 homestead exemption — and that is the reset bill a buyer pays, not the seller’s capped one. Citizens’ average premium in Monroe County is about $4,380/year; newer roofs and inland addresses usually quote below it. All in, plan on roughly $8,771/month plus any HOA or CDD assessment.
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Recently off market in Upper Matecumbe Key Islamorada
Homes in Upper Matecumbe Key Islamorada that left the market most recently, with their last list price and a public-record page for each address. Off-market pages keep the community, tax and sales-history context after a listing closes or expires.
- 33 Pen Key · last listed $2,195,000 · off market Sep 24, 2026
- 79775 Overseas Highway · last listed $29,500,000 · off market Sep 19, 2026
- 82749 Old Highway · off market Sep 10, 2026
- 82719 Old Highway · off market Sep 10, 2026
- 81200 Overseas Highway #2122 · off market Sep 10, 2026
- 81160 Old Highway · off market Sep 10, 2026
- 80639 Old Highway #309 · last listed $2,730,000 · off market Sep 10, 2026
- 80201 Overseas Highway · last listed $7,400,000 · off market Sep 10, 2026
- 154 Biscayne Boulevard · off market Sep 10, 2026
Common questions
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Listings, counts and prices are from Momentum Realty’s MLS record of active residential listings in Upper Matecumbe Key Islamorada as of 2026-09-25 and refresh as homes list and sell. Listing data provided by Florida Keys MLS, Inc. Information is deemed reliable but is not guaranteed by the MLS to be accurate. The data relating to real estate for sale on this page comes in part from the Internet Data Exchange (IDX) program of the MLS(s) named above; listings held by brokerages other than Momentum Realty are marked with the listing brokerage’s name. Information is deemed reliable but not guaranteed. Estimates are not guarantees. Equal Housing Opportunity.