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List price (High to Low) List price (Low to High) # Bedrooms # Bathrooms Year Built Square Footage Recently Updated
$5,475,000
Status: Closed
Property Type: Residential
# of Bedrooms: 5
# of Bathrooms: 7
Living Apx SqFt: 3978
Year Built: 1992
Area: 22 - Lower Matecumbe
Subdivision: Mat Ocean Bay (75.0)
Description: Welcome to your private tropical retreat in the heart of Islamorada, Florid...
Pets Allowed: Pets Allowed
Pool: 1
Waterfront: 1
Property Type: Residential
Community Features: Bike Paths
Listing Office: Ocean Sotheby's International Realty
Last Updated: May - 05 - 2026
IDX
$5,500,000
Status: Closed
Property Type: Residential
# of Bedrooms: 4
# of Bathrooms: 3.1
Living Apx SqFt: 3173
Year Built: 1994
Area: 01 - Key West
Subdivision: Old Town - Unrecord (1.0)
Description: Stunning Truman Annex home totally renovated & recently expanded. Incredibl...
Pets Allowed: Pets w/Restrictions, Pets Allowed
Pool: 1
Property Type: Residential
Listing Office: Truman & Co. (KW)
Last Updated: August - 25 - 2024
IDX
$5,750,000
Status: Closed
Property Type: Residential
# of Bedrooms: 6
# of Bathrooms: 5
Living Apx SqFt: 2635
Year Built: 1952
Area: 23 - Upper Matecumbe
Subdivision: Caribee Beach (80.0)
Description: CARIBEE BEACH HOUSE is the perfect mix of old school Islamorada charm combi...
Pets Allowed: Pets Allowed
Pool: 1
Waterfront: 1
Property Type: Residential
Listing Office: Coastal Realty of the Florida Keys
Last Updated: March - 05 - 2025
IDX
$5,350,000
Status: Closed
Property Type: Residential
# of Bedrooms: 5
# of Bathrooms: 5
Living Apx SqFt: 6007
Year Built: 2006
Area: 17 - Vaca Cut - Both Sides Holiday Inn/Key Colony
Subdivision: Vista Del Sol (53.5)
Description: Stunningly beautiful Mediterranean Oceanfront master piece on 3/4 acre of g...
Pets Allowed: Pets Allowed
Pool: 1
Waterfront: 1
Property Type: Residential
Community Features: Fire Hydrant, Bike Paths, Beach
Listing Office: Berkshire Hathaway HomeServices Keys Real Estate
Last Updated: September - 01 - 2024
IDX
$5,250,000
Status: Closed
Property Type: Commercial
# of Bedrooms: 16
# of Bathrooms: 16
Living Apx SqFt: 9082
Year Built: 1950
Area: 23 - Upper Matecumbe
Subdivision: Strattons (82.5)
Description: A boutique hotel situated on the aqua blue waters of Florida Bay will trans...
Waterfront: 1
Property Type: Commercial Sale
Listing Office: Ocean Sotheby's International Realty
Last Updated: September - 10 - 2024
IDX
$5,900,000
Property Type: Commercial
# of Bedrooms: 13
# of Bathrooms: 13
Living Apx SqFt: 4557
Year Built: 1954
Area: 15 - Sombrero Bch Rd to Vaca Cut Gulfside
Subdivision: Marathon Heights (50.5)
Description: A rare and unique income producing Hotel in Marathon. Tropical Cottages is...
Property Type: Commercial Sale
Listing Office: RE/MAX Keys Connection (KW)
Last Updated: September - 16 - 2026
IDX
$5,100,000
Status: Closed
Property Type: Vacant Land
Area: 25 - Plantation Key
Subdivision: Indian Waterways (89.0)
Description: Rare Bayfront Opportunity in Islamorada! Build your custom dream home on th...
Waterfront: 1
Property Type: Vacant Land
Listing Office: Coastal Realty of the Florida Keys
Last Updated: August - 14 - 2025
IDX
$5,000,000
Status: Closed
Property Type: Residential
# of Bedrooms: 4
# of Bathrooms: 4.2
Living Apx SqFt: 2560
Year Built: 1990
Area: 01 - Key West
Subdivision: Old Town - Unrecord (1.0)
Description: *FOR STATISTICAL PURPOSES ONLY*
This Extraordinary Estate is a work of a...
Pets Allowed: Pets Allowed
Pool: 1
Property Type: Residential
Waterfront Features: None
Listing Office: Truman & Co. (KW)
Last Updated: August - 26 - 2024
IDX
$5,900,000
Status: Closed
Property Type: Residential
# of Bedrooms: 4
# of Bathrooms: 4
Living Apx SqFt: 2993
Year Built: 1988
Area: 26 - Key Largo S of MM 96.9
Description: For Statistical purposes only....
Pets Allowed: Pets Allowed
Pool: 1
Property Type: Residential
Listing Office: Coldwell Banker Schmitt Islamorada
Last Updated: March - 31 - 2025
IDX
$5,200,000
Status: Closed
Property Type: Commercial
Year Built: 1977
Area: 01 - Key West
Subdivision: Old Town - Unrecord (1.0)
Description: 11% Cap Rate! One of the most beautiful multi-use guesthouse compounds in K...
Property Type: Commercial Sale
Listing Office: At Home in Key West, Inc.
Last Updated: September - 09 - 2024
IDX
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.