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List price (High to Low) List price (Low to High) # Bedrooms # Bathrooms Year Built Square Footage Recently Updated
$1,890,000
Property Type: Residential
# of Bedrooms: 5
# of Bathrooms: 3
Square Footage: 2845
Year Built: 1989
Area: 22 - Lower Matecumbe
Subdivision: Sandglass (74.5)
Description: Experience the ultimate Florida Keys lifestyle in this stunning split-level...
Listing Office: Ocean Sotheby's International Realty
Last Updated: June - 14 - 2026
IDX
$469,000
Open House (06/14/2026 - 2:00 pm)
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 Best-Kep...
Listing Office: Venture Realty Group
Last Updated: June - 14 - 2026
IDX
$895,000
Property Type: Residential
# of Bedrooms: 2
# of Bathrooms: 2
Square Footage: 1224
Year Built: 1979
Area: 25 - Plantation Key
Subdivision: Coral Harbour (88.0)
Description: Islamorada luxury condo and boat slip for boats to 44' - the perfect combin...
Listing Office: Coldwell Banker Schmitt Islamorada
Last Updated: June - 14 - 2026
IDX
$7,495,000
Open House (06/14/2026 - 2:00 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. Sel...
Listing Office: Venture Realty Group
Last Updated: June - 14 - 2026
IDX
$3,000,000
Open House (06/14/2026 - 10:30 am)
Property Type: Residential
# of Bedrooms: 2
# of Bathrooms: 2
Square Footage: 1110
Year Built: 1978
Area: 25 - Plantation Key
Subdivision: Venetian Shores (86.0)
Description: What does everyone want? The smallest house in a great neighborhood! THIS...
Listing Office: Coldwell Banker Schmitt Islamorada
Last Updated: June - 14 - 2026
IDX
$6,999,000
Property Type: Residential
# of Bedrooms: 4
# of Bathrooms: 5
Square Footage: 4226
Year Built: 1957
Area: 25 - Plantation Key
Subdivision: Plant Beach (87.5)
Description: Private Bayfront Estate in desirable Islamorada offering a serene ambiance ...
Listing Office: Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
Last Updated: June - 14 - 2026
IDX
$14,900,000
Property Type: Residential
# of Bedrooms: 6
# of Bathrooms: 9
Square Footage: 6573
Year Built: 2014
Area: 25 - Plantation Key
Subdivision: Misc Plantation Key (85.0)
Description: Yes, you can have it all! Tucked away behind mature tropical landscaping an...
Listing Office: Coldwell Banker Schmitt Islamorada
Last Updated: June - 13 - 2026
IDX
$1,100,000
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 2
Square Footage: 1262
Year Built: 1985
Area: 25 - Plantation Key
Subdivision: Futura Yacht Club (88.5)
Description: Futura Yacht Club Rare 3 Bed/2 Bath Condo with 39 ft. Deeded Boat Slip AND ...
Listing Office: Coldwell Banker Schmitt Islamorada
Last Updated: June - 13 - 2026
IDX
$2,195,000
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 4
Square Footage: 4537
Year Built: 1987
Area: 23 - Upper Matecumbe
Subdivision: Penn Key Club (83.0)
Description: Welcome to your legacy retreat in Islamorada's premier gated waterfront com...
Listing Office: Ocean Sotheby's International Realty
Last Updated: June - 13 - 2026
IDX
$24,995,000
Property Type: Residential
# of Bedrooms: 5
# of Bathrooms: 8
Square Footage: 9011
Year Built: 2025
Area: 25 - Plantation Key
Subdivision: Misc Plantation Key (85.0)
Description: Newly completed private oceanfront estate on 2+ acres in Plantation Key, of...
Listing Office: Coldwell Banker Schmitt Real Estate Co.
Last Updated: June - 12 - 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.