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$5,197,000
Key West
Webb Realty Co Subdivision   - MM: 1.00
10 Bed, 10 Baths, 7,193 SqFt Days Listed: 112
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

INVESTORS, DEVELOPERS, CONDO CONVERSION--1005 FLAGLER AVE AND 1009 FLAGLER AVE--Two fourplexes in the highly desirable Casa Marina neighborhood on 18,371 sq ft of land, with 7,193 sq ft of Floor Living Area, for a total of 10 bedrooms and 9 baths. 1005 Flagler is 4 units, 3 of which are 1/1, ground floor unit #1 is a 3/2 with a courtyard. Theres an on site coin laundry, as well as a garage and storage.1009 Flagler is 4 units, each a 1/1.Property Data Cards are found in Documents for each property.

$5,319,000
Key West
Key West Realty Cos Subdivisi   - MM: 3.00
24 Bed, 24 Baths, 9,000 SqFt Days Listed: 112
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

PRIME OPPORTUNITY! 1819 Atlantic Blvd, 1719/21 Josephine St, 1723/25 Josephine St, 1821 Atlantic Blvd & 1823 Atlantic Blvd. EMPLOYEE HOUSING, DEVELOPERS, CONDO CONVERSION! 3 FOURPLEXES 12 units offering 9,000 sq ft of Floor Living Area, and 2 vacant lots for a total of 23,340 sq ft of land. All 12 units are each a 2/1, for a total of 24 bedrooms and 12 baths. Buyer to verify with the governing authorities building rights for the vacant lots. Property Data Cards for each parcel are found in documents.

$6,400,000
Key West
Old Town Unlisted   - MM: 1.00
8 Bed, 8 Baths, 8,472 SqFt Days Listed: 160
-7.25% ($500,000) 1 Price Change : Last Change 2 Days Ago
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

Step into Key West history with this remarkable property, available for the first time in generations! Located just a block from world-famous Duval Street and across from the Federal Courthouse, this property at 314 Simonton Street offers a unique blend of historic charm and modern potential. Originally a hotel with a Ford dealership on the ground floor, this three-level building is steeped in heritage. Even the legendary Ernest Hemingway chose it as his base, staying here for a month while awaiting delivery of his car in 1928. Currently set up and legally recognized as 8 units, an atrium, garage, and a pool, this property provides an unmatched opportunity for someone who loves trophy properties. Whether you envision a grand single-family estate or multi-unit living combined with commercial space on the lower level, the possibilities are endless.Dont miss the chance to own a piece of Key Wests past while shaping its future with this truly one-of-a-kind property.

$6,500,000
Key West
Old Town Unlisted   - MM: 1.00
6 Bed, 6 Baths, 3,010 SqFt Days Listed: 15
Duplex - Active - Waterfront No
Side of Island: Median - Dockage: None

Two Transient Homes Now Available For Sale. Just one block off world-famous Duval Street, this rare property offers two homes - each 3 bedrooms, 3.5 baths and private pools. These have strong rental histories. These well-appointed residences blend island charm with modern comfort, featuring open-concept living areas, updated kitchens and private ensuite bedrooms. Thoughtfully designed for guest privacy and relaxation, each home includes its own outdoor lounging space and pool--perfect for cooling off after a day in the sun or enjoying a quiet evening under the palms.Whether youre looking for a investment opportunity, a vacation retreat with rental flexibility, or a mix of both, this unique setup delivers unmatched versatility just steps from the vibrant restaurants, galleries, and nightlife of Duval Street.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 04-22-2025.
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