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List price (High to Low) List price (Low to High) # Bedrooms # Bathrooms Year Built Square Footage Recently Updated
$5,870,000
Status: Closed
Property Type: Residential
# of Bedrooms: 5
# of Bathrooms: 4
Living Apx SqFt: 3173
Year Built: 1994
Area: 01 - Key West
Subdivision: Old Town - Unrecord (1.0)
Description: An Oasis in Downtown, Old Town Key West! A truly spectacular property on on...
Pool: 1
Property Type: Residential
Waterfront Features: None
Listing Office: Beach Club Brokers (KW)
Last Updated: August - 25 - 2024
IDX
$5,650,000
Status: Closed
Property Type: Commercial
# of Bedrooms: 19
# of Bathrooms: 19
Living Apx SqFt: 9228
Year Built: 1958
Area: 24 - Windley Key
Subdivision: Unplatted Windley Key (88.0)
Description: A unique Islamorada oceanfront ''boutique motel'' providing immediate ocean...
Waterfront: 1
Property Type: Commercial Sale
Listing Office: Cornell Commercial Real Estate, Inc.
Last Updated: September - 10 - 2024
IDX
$5,250,000
Status: Closed
Property Type: Residential
# of Bedrooms: 6
# of Bathrooms: 6.1
Living Apx SqFt: 6714
Year Built: 2004
Area: 17 - Vaca Cut - Both Sides Holiday Inn/Key Colony
Subdivision: Coury Sub (53.5)
Description: The Crown Jewel of the Florida Keys, Villa La Joya,a spectacular gated ocea...
Pool: 1
Waterfront: 1
Property Type: Residential
Community Features: Beach
Listing Office: American Caribbean Real Estate - Middle Keys
Last Updated: September - 01 - 2024
IDX
$5,950,000
Property Type: Residential
# of Bedrooms: 6
# of Bathrooms: 8
Living Apx SqFt: 4094
Year Built: 2020
Area: 01 - Key West
Subdivision: Old Town - Unrecord (1.0)
Description: Private Old Town property with built-in income and exceptional flexibility....
Pets Allowed: Pets Allowed
Pool: 1
Property Type: Residential
Community Features: Other Area Features
Waterfront Features: None
Listing Office: Preferred Properties (KW)
Last Updated: May - 20 - 2026
IDX
$5,950,000
Property Type: Residential
# of Bedrooms: 4
# of Bathrooms: 4
Living Apx SqFt: 3358
Year Built: 2026
Area: 25 - Plantation Key
Subdivision: Indian Waterways (89.0)
Description: Introducing an extraordinary, newly constructed waterfront estate that must...
Pets Allowed: Pets Allowed
Pool: 1
Waterfront: 1
Property Type: Residential
Community Features: Community Boat Ramp
Listing Office: American Caribbean Real Estate, Christie's International Real Estate
Last Updated: July - 21 - 2026
IDX
$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
$5,075,000
Status: Closed
Property Type: Residential
# of Bedrooms: 10
# of Bathrooms: 9
Living Apx SqFt: 6631
Year Built: 1999
Area: 19 - Crawl Key & Grassy Key
Subdivision: Grassy Key (58.9)
Description: Private Open Waterfront Estate. Luxurious Appointments Accent this Enormous...
Pets Allowed: Pets Allowed
Pool: 1
Waterfront: 1
Property Type: Residential
Listing Office: Coldwell Banker Schmitt R.E.
Last Updated: September - 02 - 2024
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
$5,087,250
Status: Closed
Property Type: Residential
# of Bedrooms: 4
# of Bathrooms: 5.1
Living Apx SqFt: 6422
Year Built: 2005
Area: 23 - Upper Matecumbe
Subdivision: Misc Upper Matacumbe (82.0)
Description: The finest of the bay front parcels in the heart of Islamorada! Peaceful, ...
Pets Allowed: Pets Allowed
Pool: 1
Waterfront: 1
Property Type: Residential
Listing Office: Ocean Sotheby's International Realty
Last Updated: September - 03 - 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.