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Florida Keys Multi-Family Homes for Sale in the Florida Keys

Total Listings 87
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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: 120
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: 120
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: 168
-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: 23
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.

$7,900,000
Key Largo
Sunrise Point   - MM: 95.00
10 Bed, 10 Baths, 5,392 SqFt Days Listed: 26
Multi-Units - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Other Dock

This unique property combines privacy, comfort, and the beauty of coastal living. With ample space for gatherings and adventures on the bay, youll fall in love with the charm and tranquility of this magnificent bayfront estate. Enjoy year round sunsets from this 2 acre estate on Florida Bay! This is perfect for an extended family or group of friends to enjoy. 3 dwellings on 2 separate parcels plus deeded baybottom make this a truly unique property. Gated for privacy, the driveway passes the Coral House, which is used as a licensed vacation rental. Continue towards the bay where the Cottage and Florida Bay House are nestled into the mature tropical landscaping. Florida Bay is straight ahead with a jetty into the Bay which is the perfect spot for sunning or stargazing. The boatramp next to the jetty is handy for launching kayaks and paddleboards to explore Florida Bay. Originally built in 1961, the Florida Bay House was expanded in the early 70s and has 3 bedrooms and 3 baths with the master suite upstairs. The Cottage was built in 1956 and is a quaint guest house. The Coral House has 4 bedrooms and 3 baths, was built in 1992 and is in the X flood zone. Dont miss the opportunity to own this slice of paradise! Contact us today to schedule your private tour and experience the magic of this beautiful bayfront property.

$12,888,000
Key West
Key West Investment Co Subdiv   - MM: 1.00
3 Bed, 3 Baths, 2,071 SqFt Days Listed: 4
Duplex - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

A Fabulous find on the ATLANTIC SIDE of the Island of Key West!Welcome to a truly unique opportunity in the heart of Key West. Two story home with ocean views galore faces the Atlantic! This exceptional property stands alone, with no other identical or closely similar properties that exist anywhere in Key West. As the right set of circumstances are here and now, shows an unparalleled combination of an oversized ocean view lot with location only three blocks from Duval St, the gateway to downtown. As the last, one and only available undeveloped property in the HISTORIC COMMERCIAL TOURIST DISTRICT (HCT zone), does present a very rare and last chance to create something extraordinary.Imagine waking up to breathtaking unobstructed ocean and beach views every day, seabirds always passing, breezes gently arriving to your lanai as you enjoy the vibrant atmosphere of Key West, like nowhere else- this can be had, this is island living to the max! This 8700 sq ft property area and two story home provides ample space for your creative vision, whether its a luxurious residence, a boutique hotel, restaurant, or an optional commercial venture, as HCT zoning offers varied uses.This property is all about the wonderful adventure of developing a vision for a new life. Let your imagination run wild and transform this blank canvas into your dream project.Dont miss out on this once-in-a-lifetime opportunity.Call today for your private tour and start envisioning your future in Key West!

$13,995,000
Cudjoe Key
Sacarma   - MM: 21.00
31 Bed, 31 Baths, SqFt Days Listed: 316
-3.45% ($500,000) 1 Price Change : Last Change 82 Days Ago
Multi-Units - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp,Basin

Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions), over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Shared coin laundry, 2 swimming pools, 3 private driveways. 2 parcels on US 1 are zoned Sub Urban Commercial, excellent rental history. Property spans from US 1 to the Atlantic Ocean. Owner is licensed Realtor. Please do not walk on the property without an appointment

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 04-30-2025.
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