Islamorada Homes for Sale

Islamorada calls itself the Village of Islands, spread across Plantation Key, Windley Key, and Upper and Lower Matecumbe. It is known for sportfishing, waterfront dining, and some of the finest bayfront and oceanfront homes in the Keys. Browse the latest Islamorada listings below, straight from the Florida Keys MLS.

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$549,500

81801 Overseas Highway 715, Upper Matecumbe Key Islamorada, FL

Active

1BD 1BA 358SF

Last Modified: 7:24pm, July 15, 2026

IDX

Listing Office: Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

$550,000

80450 Overseas Highway APT 106, Upper Matecumbe Key Islamorada, FL

Active

2BD 3BA 1,303SF

Last Modified: 12:51am, July 1, 2026

IDX

Listing Office: Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

$1,199,000

143 N Hammock Road, Upper Matecumbe Key Islamorada, FL

Active

3BD 3BA 2,022SF

Last Modified: 1:10pm, June 11, 2026

IDX

Listing Office: Flat Fee MLS Realty

$15,950,000

20 Avacado Street, Upper Matecumbe Key Islamorada, FL

Active

6BD 8BA 6,680SF

Last Modified: 4:21pm, April 25, 2026

IDX

Listing Office: Beycome of Florida, LLC

$22,500,000

81486 Overseas Highway, Upper Matecumbe Key Islamorada, FL

Active

7BD 9BA 8,878SF

Last Modified: 3:14pm, April 23, 2026

IDX

Listing Office: American Caribbean Real Estate, Christie's International Real Estate

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The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.

Islamorada Homes for Sale

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