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List price (High to Low) List price (Low to High) # Bedrooms # Bathrooms Year Built Square Footage Recently Updated
$2,699,000
Property Type: Residential
# of Bedrooms: 4
# of Bathrooms: 4
Square Footage: 3315
Year Built: 2017
Area: 23 - Upper Matecumbe
Subdivision: Strattons (82.5)
Description: Location! Location! Location! This incredible custom designed home is loca...
Listing Office: Ocean Sotheby's International Realty
Last Updated: October - 30 - 2026
IDX
$10,950,000
Property Type: Residential
# of Bedrooms: 6
# of Bathrooms: 8
Square Footage: 6577
Year Built: 2025
Area: 22 - Lower Matecumbe
Subdivision: Davis Shores (77.0)
Description: Sunset Sanctuary. Natural beauty and captivating sunsets of the Florida Key...
Listing Office: American Caribbean Real Estate, Christie's International Real Estate
Last Updated: October - 30 - 2026
IDX
$649,000
Property Type: Residential
# of Bedrooms: 1
# of Bathrooms: 1
Square Footage: 550
Year Built: 1988
Area: 23 - Upper Matecumbe
Subdivision: Strattons (82.5)
Description: Crystal-clear turquoise waters, swaying palms, and gentle ocean breezes cre...
Listing Office: American Caribbean Real Estate, Christie's International Real Estate
Last Updated: October - 30 - 2026
IDX
$22,500,000
Property Type: Residential
# of Bedrooms: 7
# of Bathrooms: 9
Square Footage: 8878
Year Built: 2026
Area: 23 - Upper Matecumbe
Subdivision: Misc Upper Matacumbe (82.0)
Description: Introducing Isla House. A truly exceptional waterfront estate in the heart ...
Listing Office: American Caribbean Real Estate, Christie's International Real Estate
Last Updated: October - 30 - 2026
IDX
$849,900
Property Type: Residential
# of Bedrooms: 2
# of Bathrooms: 2
Square Footage: 793
Year Built: 2019
Area: 24 - Windley Key
Subdivision: Galen Beach (85.0)
Description: Beautiful Atlantic Ocean views surround this newer concrete home featuring ...
Listing Office: Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
Last Updated: October - 30 - 2026
IDX
$450,000
Property Type: Residential
# of Bedrooms: 1
# of Bathrooms: 1
Area: 24 - Windley Key
Subdivision: Galen Beach (85.0)
Description: ISLAMORADA RETREAT! Whether you're looking for a full-time residence, vacat...
Listing Office: Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
Last Updated: October - 30 - 2026
IDX
$375,000
Property Type: Residential
# of Bedrooms: 1
# of Bathrooms: 1
Area: 24 - Windley Key
Subdivision: Galen Beach (85.0)
Description: ISLAMORADA RETREAT! Whether you're looking for a full-time residence, vacat...
Listing Office: Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
Last Updated: October - 30 - 2026
IDX
$5,999,000
Open House (10/30/2026 - 4:00 pm)
Property Type: Residential
# of Bedrooms: 8
# of Bathrooms: 6
Square Footage: 3649
Year Built: 1984
Area: 23 - Upper Matecumbe
Subdivision: Strattons (82.5)
Description: Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. & 7...
Listing Office: LoKation Real Estate
Last Updated: October - 30 - 2026
IDX
$2,800,000
Property Type: Residential
# of Bedrooms: 5
# of Bathrooms: 3
Square Footage: 1950
Year Built: 2023
Area: 25 - Plantation Key
Subdivision: Plant Key Colony (90.0)
Description: Welcome to Islamorada, one of the most desirable islands in the Florida Key...
Listing Office: Still Water Properties
Last Updated: October - 30 - 2026
IDX
$399,000
Property Type: Residential
# of Bedrooms: 2
# of Bathrooms: 2
Square Footage: 989
Year Built: 1977
Area: 25 - Plantation Key
Subdivision: Plant By The Sea (87.5)
Description: Enjoy a tropical retreat at Plantation By The Sea, an oceanfront community ...
Listing Office: LoKation Real Estate
Last Updated: October - 29 - 2026
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.