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List price (High to Low) List price (Low to High) # Bedrooms # Bathrooms Year Built Square Footage Recently Updated
$999,988
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 2
Square Footage: 2137
Year Built: 1975
Area: 25 - Plantation Key
Subdivision: Sea Gulls (90.0)
Description: Islamorada Oceanfront Penthouse - Over 2,100 square feet of Elevated Coasta...
Listing Office: LoKation Real Estate - Key Largo
Last Updated: February - 01 - 2026
IDX
$3,800,000
Property Type: Residential
# of Bedrooms: 4
# of Bathrooms: 5
Square Footage: 2574
Year Built: 2020
Area: 23 - Upper Matecumbe
Subdivision: Russell Estates (83.2)
Description: The Villas at the Islands of Islamorada is a meticulously designed, private...
Listing Office: Ocean Sotheby's International Realty
Last Updated: January - 31 - 2026
IDX
$4,975,000
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 2
Square Footage: 1264
Year Built: 1963
Area: 22 - Lower Matecumbe
Subdivision: Mat Ocean Bay (75.0)
Description: Come home to outstanding views with 109 feet of bay frontage in Lower Matec...
Listing Office: Ocean Sotheby's International Realty
Last Updated: January - 31 - 2026
IDX
$21,500,000
Property Type: Residential
# of Bedrooms: 6
# of Bathrooms: 8
Square Footage: 6692
Year Built: 2022
Area: 25 - Plantation Key
Subdivision: Plant Beach (87.5)
Description: A private sanctuary of coastal sophistication, The Oasis offers two residen...
Listing Office: Ocean Sotheby's International Realty
Last Updated: January - 31 - 2026
IDX
$590,000
Property Type: Residential
# of Bedrooms: 2
# of Bathrooms: 2
Square Footage: 981
Year Built: 1976
Area: 23 - Upper Matecumbe
Subdivision: Palms of Isla (80.0)
Description: 🌊 Spectacular Direct Ocean Views!
✨ Islamorada's BestR...
Listing Office: Venture Realty Group
Last Updated: January - 31 - 2026
IDX
$1,295,000
Open House (01/31/2026 - 12:00 pm)
Property Type: Residential
# of Bedrooms: 2
# of Bathrooms: 2
Square Footage: 946
Year Built: 2019
Area: 23 - Upper Matecumbe
Subdivision: Windy Cove (84.0)
Description: Stunning Ocean Views in Islamorada - the Fishing Capital of the World!
Enj...
Listing Office: Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
Last Updated: January - 31 - 2026
IDX
$2,650,000
Property Type: Residential
# of Bedrooms: 4
# of Bathrooms: 3
Square Footage: 2098
Year Built: 1988
Area: 22 - Lower Matecumbe
Subdivision: Port Antigua (74.5)
Description: Stunning canal-front home at the rare T-junction of two crystal-clear water...
Listing Office: Phantom Real Estate
Last Updated: January - 30 - 2026
IDX
$965,000
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 2
Square Footage: 1842
Year Built: 2001
Area: 25 - Plantation Key
Subdivision: Treasure Harbor (86.5)
Description: 3-bedroom, 2-bath pool home brings vacation vibes! Custom built with though...
Listing Office: Better Homes and Gardens Real Estate Destinations
Last Updated: January - 30 - 2026
IDX
$15,750,000
Property Type: Residential
# of Bedrooms: 7
# of Bathrooms: 7
Square Footage: 5900
Year Built: 2025
Area: 22 - Lower Matecumbe
Subdivision: Mat Ocean Bay (75.0)
Description: Experience the ultimate in coastal luxury and sophistication in this brand-...
Listing Office: The Agency Florida Keys
Last Updated: January - 30 - 2026
IDX
$5,800,000
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 3
Square Footage: 3019
Year Built: 2014
Area: 23 - Upper Matecumbe
Subdivision: Strattons (82.5)
Description: Islamorada Bayfront Estate with Dockage & Open Bay Views... all in downtown...
Listing Office: Coldwell Banker Schmitt Islamorada
Last Updated: January - 30 - 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.