Old Town - Unlisted (1.0) Real Estate

Step into this bright and airy two-story single-family move in ready home nestled in the heart of Historic Old Town Key West. Boasting 3 inviting bedrooms, 2 baths, and an open floor plan with a spacious kitchen and dining or bonus room, this residence offers the perfect blend of comfort and entertainment space. With the added convenience of off-street parking and its prime location within walking distance to an array of restaurants, clubs, and the waterfront, this home presents a wealth of flexibility for your ideal living experience.

840 Olivia Street, Key West

Listing Courtesy Of Keller Williams Key West Compass Realty, Contact: (305) 292-0020

$949,000

2 Beds ⋅ 2 Baths ⋅ 611617 MLS

Welcome to your dream getaway! This enchanting conch cottage is just two blocks from Duval Street, featuring a delightful pool house that enhances its charm. A Slice of Paradise featuring High ceilings with exposed beams and trapezoid transom windows create an airy, open atmosphere. Modern Upgrades include a beautifully updated kitchen and baths, complete with stainless steel appliances, including a gas stove, composite counters, and stylish cabinetry.A cozy loft area serves as extra sleeping space for kids or guests and offers incredible climate-controlled storage.Outdoor Oasis**: The fabulous outdoor space under canvas extends your living area and is prepped for an outdoor TV, perfect for entertaining. Gorgeous Shared Pool with a stunning pool adorned with distinctive mosaic tiles that reflect the colors of the sand and sea. The pool house includes a full-size futon, half bath, and a private outdoor shower ideal for guests who appreciate their own space. A rear shed and brick pavers provide extra storage options alongside the house.Low monthly HOA fees, an X-zone flood designation, and insurance mitigations like hurricane-rated storm shutters make this a smart choice for Old Town living. Located just steps from the iconic Hemingway House, Blue Heaven, and Truman Annex, this cottage offers the perfect blend of comfort and convenience. Don't miss out on this exceptional opportunity!

306 Olivia Street, Key West

Listing Courtesy Of Key West Properties (KW), Contact:

$2,799,000

10 Beds ⋅ 6 Baths ⋅ 611609 MLS

Unlock the potential of this exceptional multifamily complex nestled in the heart of Old Town Key West. With a total of six units offering a diverse mix of layouts, including three 1-bedroom/1-bathroom units, two 2-bedroom/1-bathroom units, and one 3-bedroom/1-bathroom unit, this property presents an unparalleled investment opportunity in one of the most coveted destinations in the Florida Keys. Don't miss your chance to seize this investment gem in the heart of Old Town Key West. Schedule a viewing today and make your mark on the vibrant landscape of Key West real estate!

912 Pohalski Street, Key West

Listing Courtesy Of Buy The Keys, Contact: (305) 916-9020

$2,799,000

10 Beds ⋅ 6 Baths ⋅ 611608 MLS

Unlock the potential of this exceptional multifamily complex nestled in the heart of Old Town Key West. With a total of six units offering a diverse mix of layouts, including three 1-bedroom/1-bathroom units, two 2-bedroom/1-bathroom units, and one 3-bedroom/1-bathroom unit, this property presents an unparalleled investment opportunity in one of the most coveted destinations in the Florida Keys. Don't miss your chance to seize this investment gem in the heart of Old Town Key West. Schedule a viewing today and make your mark on the vibrant landscape of Key West real estate!

912 Pohalski Street, Key West

Listing Courtesy Of Buy The Keys, Contact: (305) 916-9020

$499,000

1 Beds ⋅ 1 Baths ⋅ 611606 MLS

Transiently licensed vacation rental unit ideally located in the heart of Old Town Key West! The complex comprises 13 units with amenities including a shared pool, deck, and onsite laundry facilities. Situated on the first floor, this unit offers convenience and privacy. Just steps away are Key West's top attractions such as the Ernest Hemingway Home and Museum, vibrant Duval Street, iconic Mallory Square, and the picturesque Fort Zachary Taylor Beach and Park. Perfect for those looking to invest in a prime income producing vacation rental.

1016 Howe Street Unit #4, Key West

Listing Courtesy Of Buy The Keys, Contact: (305) 916-9020

$5,999,999

6 Beds ⋅ 7 Baths ⋅ 611566 MLS

Introducing 522 Elizabeth Street, a fully reimagined Key West masterpiece offering 6 bedrooms, 6.5 bathrooms, and over 3,000 sq ft of luxurious living space. Just 2 blocks from vibrant Duval Street, this rare gem combines historic charm with modern sophistication. The home has been meticulously rebuilt with all-new concrete footings, structural lumber, impact windows, copper gutters, a brand-new roof, two 5-ton A/C units, dual washers/dryers, and much more. Inside, the layout has been entirely redesigned with award-winning David L. Smith Interiors curating a stunning decor.Upon entering the home, you're greeted by elegant three-piece base and crown molding- setting the tone for the home's attention to detail. The first floor features a spacious primary ensuite bedroom with a custom walk-in closet, Italian glass tile accents, a floating double vanity, a walk-in shower, and a fully automated Kohler toilet. A beautifully appointed living room leads to an additional ensuite bedroom and the show-stopping gourmet kitchen. This culinary space boasts Viking appliances, quartz counters, and a massive waterfall island perfect for entertaining.Step outside to your private oasis, featuring a new Gunite pool with a large sun ledge and 4 custom waterfalls cascading from a glass mosaic wall. The professionally landscaped yard is complete with mature trees and a 6-zone irrigation system. The expansive IPE deck with a covered outdoor dining area is the ideal backdrop for island living and entertaining. Upstairs, the home offers another primary ensuite bedroom with spiral stairs that lead to loft storage. The 3 additional ensuite bedrooms each offer their own unique charm- some with treetop views, Italian porcelain, or private balcony.This residence epitomizes luxurious island living with two off-street parking spaces and a carport for added convenience.Don't miss the opportunity to make it yours- schedule a private showing today!

522 Elizabeth Street, Key West

Listing Courtesy Of Brenda Donnelly Real Estate LLC, Contact: (305) 304-1116

$3,000

1 Baths ⋅ 611561 MLS

Great Visibility for your business in this 528 soft commercial space. Off street parking for customers and employees. Monthly Rent is Base only. In addition are net charges and sales tax. Vacant and Easy to see.

929 Truman Avenue Unit #B, Key West

Listing Courtesy Of Preferred Properties (KW), Contact: (305) 294-3040

$1,580,000

3 Beds ⋅ 4 Baths ⋅ 611554 MLS

If you are looking for a home or multi-family opportunity that is like no other, you've found it in this charming and eclectic, restored, Conch home. The restoration brought out the best blend of history, island flavor, comfort and useful design. Move right in. Everything is up to current code with new impact-rated windows and doors, new metal roof, and re-built foundations. The 2 bedroom, 2 bath main house with extra rooms has new, wood flooring, closets in every bedroom, lofts for extra sleeping or storage and a large, eat-in kitchen with lots of cabinetry. The main house has a welcoming and covered front porch plus 2 more porches off either end of the kitchen. The detached 1 bedroom, 1 bath cottage in the rear of the property is also beautifully renovated and furnished and has 2 porches. It is a legal rental allowing minimum 28-day rental periods. The third building is an historic structure that was once a beloved neighborhood variety store. It has also been restored and includes a half bath and studio/creative space with a beautiful cedar ceiling. There's an outdoor shower attached to this building.Drive right in to your off-street parking spot that will double as a patio for a party. You'll find rain barrels at the downspouts of the new gutter system. There's a mature mango tree, an egg fruit tree, a papaya plant, a hog plum tree and several banana palms. An herb garden is located outside of the kitchen next to the barbecue patio. The landscaping evokes a beach feeling with rock and seashells, a hammock and of course tropical plants making it ideal for beautiful, garden gatherings.

205 Julia Street, Key West

Listing Courtesy Of Bascom Grooms Real Estate (KW), Contact: (305) 295-7511

$1,580,000

3 Beds ⋅ 4 Baths ⋅ 611552 MLS

If you are looking for a home or multi-family opportunity that is like no other, you've found it in this charming and eclectic, restored, Conch home. The restoration brought out the best blend of history, island flavor, comfort and useful design. Move right in. Everything is up to current code with new impact-rated windows and doors, new metal roof, and re-built foundations. The 2 bedroom, 2 bath main house with extra rooms has new, wood flooring, closets in every bedroom, lofts for extra sleeping or storage and a large, eat-in kitchen with lots of cabinetry. The main house has a welcoming and covered front porch plus 2 more porches off either end of the kitchen. The detached 1 bedroom, 1 bath cottage in the rear of the property is also beautifully renovated and furnished and has 2 porches. It is a legal rental allowing minimum 28-day rental periods. The third building is an historic structure that was once a beloved neighborhood variety store. It has also been restored and includes a half bath and studio/creative space with a beautiful cedar ceiling. There's an outdoor shower attached to this building.Drive right in to your off-street parking spot that will double as a patio for a party. You'll find rain barrels at the downspouts of the new gutter system. There's a mature mango tree, an egg fruit tree, a papaya plant, a hog plum tree and several banana palms. An herb garden is located outside of the kitchen next to the barbecue patio. The landscaping evokes a beach feeling with rock and seashells, a hammock and of course tropical plants making it ideal for beautiful, garden gatherings.

205 Julia Street, Key West

Listing Courtesy Of Bascom Grooms Real Estate (KW), Contact: (305) 295-7511

$2,650

1 Baths ⋅ 611531 MLS

Excellent Opportunity to join the thriving & friendly business environment that Kino Plaza has to offer, catering to a diversity of local cafes, shopping & specialty services, steps away from Mallory Square. Outstanding foot traffic from tourists and locals between Front and Greene Streets. 105-A Fitzpatrick is a corner space with approximately ~553sf downstairs and a ~400sf upstairs loft. Admin fee and sales tax are in addition to the base rent quoted.

105-A Fitzpatrick Street, Key West

Listing Courtesy Of Berkshire Hathaway Knight & Gardner, Contact: (305) 294-5155

$3,750,000

4 Beds ⋅ 5 Baths ⋅ 611512 MLS

Welcome to this newly reimagined architectural gem in Old Town Key West. This historic home has been meticulously renovated to blend timeless charm with modern sophistication. The main house offers three bedrooms, 3.5 luxurious baths, all illuminated by natural light pouring through impact-resistant doors and windows. Throughout, the warmth of oak floors complements the clean, contemporary lines of the space. The gourmet kitchen, fitted with Bosch stainless steel appliances, is a dream for culinary enthusiasts, while the open-concept design makes it perfect for entertaining. Step outside to your private oasis, where a stunning waterfall pool is the centerpiece of a lushly landscaped garden. The outdoor kitchen and spacious dining area are perfect for hosting al fresco dinners, making the most of the tropical Key West climate. For guests, a separate one-bedroom, one-bath guest house ensures privacy and comfort. Additional features include off-street parking and an electric vehicle charging station. Just two blocks away, the iconic Duval Street invites you to explore world-class dining, art galleries, and nightlife, with historic stops like Sloppy Joe's. A two-block stroll west brings you to the literary haven of the Ernest Hemingway Home and Museum, while the Key West Lighthouse, just one block farther, offers panoramic island views.For beachgoers, the tranquil shores of Fort Zachary Taylor Historic State Park await, only five blocks away. History lovers will appreciate being just*five blocks from the Truman Little White House, a symbol of presidential retreat. Each evening, Mallory Square, also five block away, offers a festive sunset celebration, a must-see experience. For waterfront dining and sailing excursions, the Key West Historic Seaport is within the same easy reach. 907 Whitehead Street isn't just a home--it's a luxurious retreat in the heart of Key West's most coveted neighborhood, offering a blend of history, elegance, and walkable island living.

709 Whitehead Street, Key West

Listing Courtesy Of Royal Palms Realty (KW), Contact: (305) 923-9884

$2,399,000

4 Beds ⋅ 2 Baths ⋅ 611458 MLS

Step into a piece of Key West history with this fully renovated, light-filled historic home in the heart of Old Town. Blending old-world charm with modern updates, this legal duplex offers endless possibilities. Whether you're looking for a smart investment, a vacation getaway, or a new primary residence, this property is ready for you. Live in one unit and rent the other, or enjoy the entire home for yourself! There is an interior staircase to enter the upstairs unit.Each spacious level features 2 bedrooms, 1 bathroom, a full kitchen with stainless steel appliances, laundry, and an open-concept living/kitchen/dining area. The lower unit opens to a deck and pool--perfect for relaxing and entertaining. The upper unit boasts abundant natural light and a large wraparound porch, ideal for enjoying the tropical surroundings. Both units come fully furnished, and the upstairs unit has a long-term tenant in place, ensuring immediate rental income.Located in a prime spot close to the Old Seaport, top restaurants, and bars, but in a quieter neighborhood, this home is your ticket to island living in paradise!

1022 Fleming Street, Key West

Listing Courtesy Of Ocean Sotheby's International Realty, Contact: (305) 294-1117

Old Town - Unlisted (1.0) Real Estate

Newest Listings in Old Town - Unlisted (1.0)