Condos for Sale in Upper Matecumbe Key Islamorada, FL

10 condos are for sale in Upper Matecumbe Key Islamorada, FL as of 2026-09-06. The median list price is $622,000, most condos list between $550K to $3.50M, and the median listing has been on the market 132 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.

$549,500

1 bd · 1 ba

81801 Overseas Highway #716

Upper Matecumbe Key Islamorada

Listing courtesy of Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

$549,500

1 bd · 1 ba

81801 Overseas Highway #715

Upper Matecumbe Key Islamorada

Listing courtesy of Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

$649,000

1 bd · 1 ba

81801 Old Highway #754

Upper Matecumbe Key Islamorada

Listing courtesy of American Caribbean Real Estate, Christie's International Real Estate

$715,000

1 bd · 1 ba

81801 Overseas Highway #637

Upper Matecumbe Key Islamorada

Listing courtesy of Ocean Sotheby's International Realty

$595,000

2 bd · 2 ba

80450 Overseas Highway #204

Upper Matecumbe Key Islamorada

Listing courtesy of Palm House Real Estate

$699,000

1 bd · 1 ba

81801 Overseas Highway ## 729

Upper Matecumbe Key Islamorada

Listing courtesy of Coldwell Banker Schmitt Key Largo

$585,000

1 bd · 1 ba

81801 Overseas Highway #727

Upper Matecumbe Key Islamorada

Listing courtesy of Coldwell Banker Schmitt Islamorada

$2.73M

3 bd · 3 ba

80639 Old Highway #309

Upper Matecumbe Key Islamorada

Listing courtesy of Ocean Sotheby's International Realty

$550,000

2 bd · 2.5 ba

80450 Overseas Highway #APT 106

Upper Matecumbe Key Islamorada

Listing courtesy of Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

$3.50M

4 bd · 4.5 ba

80639 Old Highway #201

Upper Matecumbe Key Islamorada

Listing courtesy of LPT Realty, LLC

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 $622,000; 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

$1M and up: 2 homes

• $2.73M · 3 bd / 3 ba · 80639 Old Highway #309
• $3.50M · 4 bd / 4.5 ba · 80639 Old Highway #201

What a home in Upper Matecumbe Key Islamorada costs to own

Take the median $622,000 listing with 20% down at today’s 6.71% 30-year rate: principal and interest run about $3,214/month. All in, plan on roughly $3,214/month plus any HOA or CDD assessment.

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Common questions

Listings, counts and prices are from Momentum Realty’s MLS record of active residential listings in Upper Matecumbe Key Islamorada as of 2026-09-06 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.