Condos for Sale in Upper Matecumbe Key Islamorada, FL
8 condos are for sale in Upper Matecumbe Key Islamorada, FL as of 2026-09-25. The median list price is $567,500, most condos list between $550K to $715K, and the median listing has been on the market 145 days. 0 condos came on the market this week.
Newest condos 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 condos 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 $567,500; the busiest band is $500K – $750K.
$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
Every home for sale in Upper Matecumbe Key Islamorada right now (8)
All 8 active Upper Matecumbe Key Islamorada listings with a detail page, newest first, refreshed twice a day from the MLS.
- $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
- $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
- $550,000 · 2 bd / 2.5 ba · 80450 Overseas Highway #APT 106
Condos 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 | Condos for sale | Median list price |
|---|---|---|
| 33036 | 8 | $567,500 |
What a home in Upper Matecumbe Key Islamorada costs to own
Take the median $567,500 listing with 20% down at today’s 6.95% 30-year rate: principal and interest run about $3,005/month. Monroe County’s typical millage of 8.82 puts property tax near $4,562/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 $3,750/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.