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$5,319,000
Key West
Key West Realty Cos Subdivisi   - MM: 3.00
24 Bed, 24 Baths, 9,000 SqFt Days Listed: 168
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.

$5,900,000
Key West
Old Town Unlisted   - MM: 1.00
8 Bed, 8 Baths, 8,472 SqFt Days Listed: 216
-14.49% ($1,000,000) 2 Price Changes : 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: 71
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.

$11,888,000
Key West
Key West Investment Co Subdiv   - MM: 1.00
3 Bed, 3 Baths, 2,071 SqFt Days Listed: 52
-7.76% ($1,000,000) 1 Price Change : Last Change 6 Days Ago
Duplex - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Fabulous Find on the Atlantic Side of Key West!Welcome to a truly unique opportunity in the heart of Key West. As the last and only remaining undeveloped property in the Historic Commercial Tourist District (HCT zone), this listing presents a rare and final chance to create something extraordinary. Imagine waking up to breathtaking, unobstructed ocean and beach views every day. Seabirds passing overhead, gentle breezes arriving at your lanai--its an experience like nowhere else. This is island living at its finest!Permitted HCT uses include:Single-family and two-family residential dwellingsMultiple-family residential dwellingsRestaurant Business and professional officesHotels, motels, transient lodging, and moreThis two-story home comes equipped with two separate electric meters.This exceptional property is truly one of a kind, with no identical or closely similar listings anywhere in Key West. The ideal circumstances are here and now--an unparalleled combination of an oversized ocean-view lot, located just three blocks from Duval Street, the gateway to downtown.Spanning 8,700 square feet, this property offers ample space for your creative vision, whether you dream of building a luxurious residence, alongside a commercial ventureboutique hotel, or restaurant, -- this and more are supported by HCT zoning.This property is all about the excitiment of shaping a new vision for a future in paradise. Let your imagination run wild and transform this blank canvas into something extraordinary.Dont miss out on this once-in-a-lifetime opportunity--call today for your private tour and start envisioning your future in Key West!

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 06-17-2025.
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