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Turnkey Key West Investment Property with Transient Rental License! Located in the heart of Old Town, just steps from Duval Street, this charming 1-bedroom, 1.5-bathroom townhouse offers an attractive opportunity to own an income-producing property in one of Key West's most desirable locations. With a transient rental license, this property allows for short-term vacation rental potential while also serving as a personal island getaway when not in use. The first floor features an open-concept living and dining area, an open kitchen, a convenient half bath, and durable tile flooring throughout. Upstairs, the spacious bedroom offers abundant natural light, ample storage, wood flooring, and a full bathroom with a walk-in shower. The property is offered fully furnished and turnkey, making it well suited for an investor seeking a vacation rental property without the added expense and effort of furnishing it. Gated common areas enhance the appeal with lush tropical landscaping, a charming courtyard, and a shared heated swimming pool, providing desirable amenities for vacation guests. With its prime Old Town location near Duval Street's restaurants, shops, and nightlife, combined with a transient rental license and turnkey condition, this townhouse presents a compelling opportunity for investors seeking a Key West vacation rental property with personal-use flexibility.

1 Beds ⋅ 2 Baths ⋅ 621683 MLS

Turnkey Key West Investment Property with Transient Rental License! Located in the heart of Old Town, just steps from Duval Street, this charming 1-bedroom, 1.5-bathroom townhouse offers an attractive opportunity to own an income-producing property in one of Key West's most desirable locations. With a transient rental license, this property allows for short-term vacation rental potential while also serving as a personal island getaway when not in use. The first floor features an open-concept living and dining area, an open kitchen, a convenient half bath, and durable tile flooring throughout. Upstairs, the spacious bedroom offers abundant natural light, ample storage, wood flooring, and a full bathroom with a walk-in shower. The property is offered fully furnished and turnkey, making it well suited for an investor seeking a vacation rental property without the added expense and effort of furnishing it. Gated common areas enhance the appeal with lush tropical landscaping, a charming courtyard, and a shared heated swimming pool, providing desirable amenities for vacation guests. With its prime Old Town location near Duval Street's restaurants, shops, and nightlife, combined with a transient rental license and turnkey condition, this townhouse presents a compelling opportunity for investors seeking a Key West vacation rental property with personal-use flexibility.

921 Center St Unit 2, Key West

$1,499,000

Welcome to 1809 Seidenberg Avenue, a fully renovated island retreat in the heart of Midtown Key West. A full wall of pocket sliders opens the bright, open floor plan to the outdoors, so living space and backyard flow together. Out back you'll find one of the larger pools on the island, a spacious deck, a large chickee hut for shaded dining and lounging, and your own putting green, all inside a fenced yard with low-maintenance turf and mature tropical landscaping. Inside are 3 bedrooms and 2 baths, with quartz countertops, built-in cabinetry, stainless appliances, central air and ceiling fans throughout. The home is solid CBS construction with off-street parking. It's offered fully furnished and turnkey, with over $60K in rentals already booked for 2027. Whether you want a primary residence, a getaway or an income property, this one is ready to enjoy on day one. Schedule your private tour today!

3 Beds ⋅ 2 Baths ⋅ 621680 MLS

Welcome to 1809 Seidenberg Avenue, a fully renovated island retreat in the heart of Midtown Key West. A full wall of pocket sliders opens the bright, open floor plan to the outdoors, so living space and backyard flow together. Out back you'll find one of the larger pools on the island, a spacious deck, a large chickee hut for shaded dining and lounging, and your own putting green, all inside a fenced yard with low-maintenance turf and mature tropical landscaping. Inside are 3 bedrooms and 2 baths, with quartz countertops, built-in cabinetry, stainless appliances, central air and ceiling fans throughout. The home is solid CBS construction with off-street parking. It's offered fully furnished and turnkey, with over $60K in rentals already booked for 2027. Whether you want a primary residence, a getaway or an income property, this one is ready to enjoy on day one. Schedule your private tour today!

1809 Seidenberg Ave, Key West

$1,725,000

Pool, Parking & Old Town Key West- Experience the charm of Key West living in this completely renovated, like new two story residence offering three bedrooms and three and a half bathrooms. A welcoming covered front porch, accented by classic pale blue shutters, creates a charming first impression. Inside, bright and airy living spaces feature a soothing coastal color palette, wood look flooring, and recessed lighting throughout. The well-appointed kitchen showcases crisp white cabinetry and light countertops, creating a fresh, timeless aesthetic. Expansive living room windows invite natural light while offering views of the private backyard retreat, complete with a pool, spacious deck and even a parking space in front of the home. Whether enjoying a quiet morning on the front porch, lounging poolside, or entertaining family and friends, this home offers the perfect setting to embrace the relaxed Key West lifestyle.

3 Beds ⋅ 4 Baths ⋅ 621679 MLS

Pool, Parking & Old Town Key West- Experience the charm of Key West living in this completely renovated, like new two story residence offering three bedrooms and three and a half bathrooms. A welcoming covered front porch, accented by classic pale blue shutters, creates a charming first impression. Inside, bright and airy living spaces feature a soothing coastal color palette, wood look flooring, and recessed lighting throughout. The well-appointed kitchen showcases crisp white cabinetry and light countertops, creating a fresh, timeless aesthetic. Expansive living room windows invite natural light while offering views of the private backyard retreat, complete with a pool, spacious deck and even a parking space in front of the home. Whether enjoying a quiet morning on the front porch, lounging poolside, or entertaining family and friends, this home offers the perfect setting to embrace the relaxed Key West lifestyle.

1105 Watson St, Key West

$4,400,000

BRAND NEW CONSTRUCTION MIDTOWN WEST Meticulously crafted by a local luxury builder, this exceptional new 4 bedroom 3 bath residence combines superior construction, thoughtful architectural design and exquisite attention to detail to create effortless tropical elegance. Step inside to soaring 20-foot ceilings, a light-filled open floor complimented by 12'x40' tile flooring. A striking floating staircase with open wood treads adds architectural flair. The gourmet kitchen showcases custom Hanson and Bringle cabinetry, granite countertops and premium stainless steel Thermadore appliances, with a central island and built in wet bar. The second level features two bedrooms with a Jack-and-Jill bath, while the third level offers an expansive mezzanine, with wet bar and luxurious second primary suite with soaking tub and separate shower. Custom white oak flooring, motorized Hunter Douglas Pirouette window treatments and designer lighting reflect the exceptional quality throughout. Designed for seamless indoor-outdoor living, the lush tropical setting features a heated 10' x 20' saltwater pool with six-foot swim-out, outdoor shower and exquisite outdoor kitchen with built-ins, refrigeration and grilling area. Five private porches invite morning coffee, afternoon breezes and relaxed evenings under the stars, buffeted by lushly landscaped grounds. Quality is evident in every detail, from premium Andersen impact-resistant windows and a standing-seam metal roof to Hardie board siding, AZEK trim, extensive closed-cell insulation and dual high-efficiency Mitsubishi A/C systems. A two-car tandem garage completes this thoughtfully designed island retreat, where enduring craftsmanship meets sophisticated tropical luxury in a family friendly neighborhood. Completion date Jan '27. More images to follow. Front image has been digitally created.

4 Beds ⋅ 3 Baths ⋅ 621671 MLS

BRAND NEW CONSTRUCTION MIDTOWN WEST Meticulously crafted by a local luxury builder, this exceptional new 4 bedroom 3 bath residence combines superior construction, thoughtful architectural design and exquisite attention to detail to create effortless tropical elegance. Step inside to soaring 20-foot ceilings, a light-filled open floor complimented by 12'x40' tile flooring. A striking floating staircase with open wood treads adds architectural flair. The gourmet kitchen showcases custom Hanson and Bringle cabinetry, granite countertops and premium stainless steel Thermadore appliances, with a central island and built in wet bar. The second level features two bedrooms with a Jack-and-Jill bath, while the third level offers an expansive mezzanine, with wet bar and luxurious second primary suite with soaking tub and separate shower. Custom white oak flooring, motorized Hunter Douglas Pirouette window treatments and designer lighting reflect the exceptional quality throughout. Designed for seamless indoor-outdoor living, the lush tropical setting features a heated 10' x 20' saltwater pool with six-foot swim-out, outdoor shower and exquisite outdoor kitchen with built-ins, refrigeration and grilling area. Five private porches invite morning coffee, afternoon breezes and relaxed evenings under the stars, buffeted by lushly landscaped grounds. Quality is evident in every detail, from premium Andersen impact-resistant windows and a standing-seam metal roof to Hardie board siding, AZEK trim, extensive closed-cell insulation and dual high-efficiency Mitsubishi A/C systems. A two-car tandem garage completes this thoughtfully designed island retreat, where enduring craftsmanship meets sophisticated tropical luxury in a family friendly neighborhood. Completion date Jan '27. More images to follow. Front image has been digitally created.

1618 South Street, Key West

$999,000

Nestled within a private tropical oasis on a 7,500-square-foot lot, this charming Mid-Century Modern home offers the perfect blend of architectural character and island living. Approximately 64 feet of floor-to-ceiling sliders and windows fill the home with natural light and frame lush garden views from nearly every room. The three-bedroom, two-bath floor plan features clean modern lines, concrete finishes, abundant storage, and a versatile third bedroom ideal for an office, studio, nursery, or home gym. Additional highlights include central air conditioning and accordion hurricane shutters. Outside, beautifully landscaped grounds showcase crushed granite, Chicago brick, and coral pathways winding through mature palms, fruit trees, and tropical plantings. The fully fenced property offers exceptional privacy, a gated drive with off-street parking for two vehicles, an outdoor bar, and multiple entertaining areas. With ample room for a generous pool, this property presents a rare opportunity to create your own tropical retreat just a short bike ride from Old Town.

3 Beds ⋅ 2 Baths ⋅ 621670 MLS

Nestled within a private tropical oasis on a 7,500-square-foot lot, this charming Mid-Century Modern home offers the perfect blend of architectural character and island living. Approximately 64 feet of floor-to-ceiling sliders and windows fill the home with natural light and frame lush garden views from nearly every room. The three-bedroom, two-bath floor plan features clean modern lines, concrete finishes, abundant storage, and a versatile third bedroom ideal for an office, studio, nursery, or home gym. Additional highlights include central air conditioning and accordion hurricane shutters. Outside, beautifully landscaped grounds showcase crushed granite, Chicago brick, and coral pathways winding through mature palms, fruit trees, and tropical plantings. The fully fenced property offers exceptional privacy, a gated drive with off-street parking for two vehicles, an outdoor bar, and multiple entertaining areas. With ample room for a generous pool, this property presents a rare opportunity to create your own tropical retreat just a short bike ride from Old Town.

2309 Flagler Ave, Key West

$1,599,000

Nestled in a tranquil ,established neighborhood ,this property offers an opportunity for those looking to enjoy the charm of an existing home or envision something entirely new.Surrounded by properties that have been thoughtfully renovated or replaced by new construction ,the setting offers plenty of inspiration and potential. Beautiful mature foliage, including a frangipani tree and a mix of established native and exotic plants add to the property's tropical charm.A concrete wall surrounds the property insuring even more privacy. The home features two bedrooms, two full baths,a sunroom, as well as a third room adjacent to the kitchen ,with a private entrance accessible from the rear driveway.The additional space would make an ideal office or studio. A well-appointed gourmet kitchen with stainless steel appliances, central air-conditioning and hurricane shutters add to the home's comfort and convenience. Closely located just minutes from Key West's beautiful beaches ,dining, and entertainment district. Whether you chose to move in, renovate, or explore the possibilities of redevelopment , this property presents an appealing option in a peaceful residential setting.

3 Beds ⋅ 2 Baths ⋅ 621633 MLS

Nestled in a tranquil ,established neighborhood ,this property offers an opportunity for those looking to enjoy the charm of an existing home or envision something entirely new.Surrounded by properties that have been thoughtfully renovated or replaced by new construction ,the setting offers plenty of inspiration and potential. Beautiful mature foliage, including a frangipani tree and a mix of established native and exotic plants add to the property's tropical charm.A concrete wall surrounds the property insuring even more privacy. The home features two bedrooms, two full baths,a sunroom, as well as a third room adjacent to the kitchen ,with a private entrance accessible from the rear driveway.The additional space would make an ideal office or studio. A well-appointed gourmet kitchen with stainless steel appliances, central air-conditioning and hurricane shutters add to the home's comfort and convenience. Closely located just minutes from Key West's beautiful beaches ,dining, and entertainment district. Whether you chose to move in, renovate, or explore the possibilities of redevelopment , this property presents an appealing option in a peaceful residential setting.

1703 South Street, Key West

$875,000

Discover the possibilities at 3711 Duck Avenue! Situated on an oversized 6,750-square-foot lot, this updated 3 bedroom, 1-bath home offers over 1200 square feet of inviting living space with upgrades throughout, like new flooring, new HVAC, and fresh paint inside and out. The open living and dining areas create a comfortable, welcoming atmosphere ideal for everyday living and entertaining. The newly renovated kitchen features stainless steel appliances, quartzite countertops, ample counter space, a beverage cooler, and an additional under-cabinet freeze, perfect for entertaining and everyday convenience. A metal roof and impact-resistant windows add practical appeal, while off-street parking provides everyday convenience. Step outside to an expansive fenced yard offering exceptional space for outdoor entertaining, gardening, pets, or creating your own tropical retreat. The generous lot also presents exciting possibilities for expanding the existing residence or adding an accessory dwelling unit and swimming pool. Conveniently located in New Town with easy access to schools, military installations, shopping, and everyday amenities, this property combines comfortable island living with flexibility for the future. Whether you're looking for a move-in-ready Key West residence or a property with room to expand, 3711 Duck Avenue offers an outstanding opportunity.

3 Beds ⋅ 1 Baths ⋅ 621654 MLS

Discover the possibilities at 3711 Duck Avenue! Situated on an oversized 6,750-square-foot lot, this updated 3 bedroom, 1-bath home offers over 1200 square feet of inviting living space with upgrades throughout, like new flooring, new HVAC, and fresh paint inside and out. The open living and dining areas create a comfortable, welcoming atmosphere ideal for everyday living and entertaining. The newly renovated kitchen features stainless steel appliances, quartzite countertops, ample counter space, a beverage cooler, and an additional under-cabinet freeze, perfect for entertaining and everyday convenience. A metal roof and impact-resistant windows add practical appeal, while off-street parking provides everyday convenience. Step outside to an expansive fenced yard offering exceptional space for outdoor entertaining, gardening, pets, or creating your own tropical retreat. The generous lot also presents exciting possibilities for expanding the existing residence or adding an accessory dwelling unit and swimming pool. Conveniently located in New Town with easy access to schools, military installations, shopping, and everyday amenities, this property combines comfortable island living with flexibility for the future. Whether you're looking for a move-in-ready Key West residence or a property with room to expand, 3711 Duck Avenue offers an outstanding opportunity.

3711 Duck Ave, Key West

$735,000

Welcome to your dream oasis, perfectly situated directly across from a beautiful park with rare dual-street accessibility. This exceptional property blends spacious design with incredible versatility, featuring a 3-bedroom, 3-bathroom main residence, a fully detached private guest cottage, and entrances from two different streets at the front and back. As you step into the main home, you are immediately greeted by soaring, high ceilings and abundant natural light that amplify the open and airy layout. The floor plan flows effortlessly into the outdoor living spaces, featuring beautifully crafted brick-layered patios--perfect for dining alfresco, entertaining guests, or simply enjoying the peaceful breeze. Security and convenience meet at the rear of the property, which boasts off-street gated parking accessed securely from the back street. The separate backyard cottage provides the ultimate flexibility, making it an ideal space for a private home office, an artist's studio. Combined with the serene park views right out your front door and premium dual-access convenience, this unique property offers the perfect balance of community connection and private retreat.

3 Beds ⋅ 3 Baths ⋅ 621643 MLS

Welcome to your dream oasis, perfectly situated directly across from a beautiful park with rare dual-street accessibility. This exceptional property blends spacious design with incredible versatility, featuring a 3-bedroom, 3-bathroom main residence, a fully detached private guest cottage, and entrances from two different streets at the front and back. As you step into the main home, you are immediately greeted by soaring, high ceilings and abundant natural light that amplify the open and airy layout. The floor plan flows effortlessly into the outdoor living spaces, featuring beautifully crafted brick-layered patios--perfect for dining alfresco, entertaining guests, or simply enjoying the peaceful breeze. Security and convenience meet at the rear of the property, which boasts off-street gated parking accessed securely from the back street. The separate backyard cottage provides the ultimate flexibility, making it an ideal space for a private home office, an artist's studio. Combined with the serene park views right out your front door and premium dual-access convenience, this unique property offers the perfect balance of community connection and private retreat.

5435 5th Ave, Key West

$4,950,000

DUAL TRANSIENT LICENSES | A RARE DEPARTURE FROM THE ORDINARY While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands as a bold architectural departure. With its striking modern aesthetic, raw concrete elements, and serene private courtyard, this is where minimalist design meets maximum investment potential, just one block from Duval Street. | THE COMPOUND | Built in 2008 on a generous 5,220sf lot, this 2,441sf property features two distinct units, a front house and back house, connected by a heated pool oasis. Four bedrooms, four full baths, soaring two-story ceilings, and thoughtfully curated interiors showcase warm mid-century touches against clean architectural lines. Wood and tile floors, built-in cabinetry, walk-in closets, and abundant natural light through expansive glass doors create spaces that are both meditative and functional. | THE SANCTUARY | High privacy walls enclose a tranquil pool courtyard with tropical landscaping, outdoor shower, and ample off-street parking. Electric gate entry ensures complete seclusion while downtown's energy pulses just steps away. | THE OPPORTUNITY | Two active transient rental licenses with 1-day minimum stays unlock exceptional income in Key West's most sought-after location. The property's distinctive design aesthetic attracts discerning guests seeking something different, proven by outstanding reviews and strong rental performance. HNC zoning supports flexible commercial use, while X flood zone designation offers insurance advantages. | THE LOCATION | Heart of Old Town, steps from Duval's legendary dining, nightlife, galleries, and waterfront. Close enough to all the action, far enough from the noise. This is investment-grade real estate with soul, where architectural distinction drives premium rates and occupancy.

4 Beds ⋅ 4 Baths ⋅ 621632 MLS

DUAL TRANSIENT LICENSES | A RARE DEPARTURE FROM THE ORDINARY While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands as a bold architectural departure. With its striking modern aesthetic, raw concrete elements, and serene private courtyard, this is where minimalist design meets maximum investment potential, just one block from Duval Street. | THE COMPOUND | Built in 2008 on a generous 5,220sf lot, this 2,441sf property features two distinct units, a front house and back house, connected by a heated pool oasis. Four bedrooms, four full baths, soaring two-story ceilings, and thoughtfully curated interiors showcase warm mid-century touches against clean architectural lines. Wood and tile floors, built-in cabinetry, walk-in closets, and abundant natural light through expansive glass doors create spaces that are both meditative and functional. | THE SANCTUARY | High privacy walls enclose a tranquil pool courtyard with tropical landscaping, outdoor shower, and ample off-street parking. Electric gate entry ensures complete seclusion while downtown's energy pulses just steps away. | THE OPPORTUNITY | Two active transient rental licenses with 1-day minimum stays unlock exceptional income in Key West's most sought-after location. The property's distinctive design aesthetic attracts discerning guests seeking something different, proven by outstanding reviews and strong rental performance. HNC zoning supports flexible commercial use, while X flood zone designation offers insurance advantages. | THE LOCATION | Heart of Old Town, steps from Duval's legendary dining, nightlife, galleries, and waterfront. Close enough to all the action, far enough from the noise. This is investment-grade real estate with soul, where architectural distinction drives premium rates and occupancy.

720d Simonton St, Key West

$1,499,000

A TROPICAL OASIS IN NEW TOWN! Turnkey, fully furnished, and ready to enjoy, this private tropical retreat in Key West's Elamar Estates area of New Town makes island living effortless. Set on a 6,132 SF lot, this Mid Century Modern inspired home offers 1,751 SF of living space and an 80 SF pool house. Completely remodeled down to the studs in 2007, the residence features an open floor plan connecting the living room, dining room, Florida room, and kitchen, complete with premium appliances, including a Thermador five burner gas range. All main living areas overlook the lush backyard and a 28 x 12 foot heated kidney shaped pool. Two master suites, a third full bathroom with a Jacuzzi style tub and shower, custom closets, and a wine cabinet enhance the home's appeal. Enclosed by 7ft & 8ft privacy fences, the landscaped backyard offers a secluded poolside escape (perfect for your own ''no tan lines tan''). Additional features include a metal roof, impact windows and doors, central HVAC, tankless water heater, laundry room, five ceiling fans, sun protected carport, and a welcoming front porch framed by Zoysia grass and Christmas palms. Located on a quiet two block street with sidewalks and ample off street parking, the property is just half a block from the Lake McKillip boat ramp, offering access to the Atlantic and Gulf. Two kayaks are included. Shopping, restaurants, schools, and medical offices are conveniently nearby.

2 Beds ⋅ 3 Baths ⋅ 621624 MLS

A TROPICAL OASIS IN NEW TOWN! Turnkey, fully furnished, and ready to enjoy, this private tropical retreat in Key West's Elamar Estates area of New Town makes island living effortless. Set on a 6,132 SF lot, this Mid Century Modern inspired home offers 1,751 SF of living space and an 80 SF pool house. Completely remodeled down to the studs in 2007, the residence features an open floor plan connecting the living room, dining room, Florida room, and kitchen, complete with premium appliances, including a Thermador five burner gas range. All main living areas overlook the lush backyard and a 28 x 12 foot heated kidney shaped pool. Two master suites, a third full bathroom with a Jacuzzi style tub and shower, custom closets, and a wine cabinet enhance the home's appeal. Enclosed by 7ft & 8ft privacy fences, the landscaped backyard offers a secluded poolside escape (perfect for your own ''no tan lines tan''). Additional features include a metal roof, impact windows and doors, central HVAC, tankless water heater, laundry room, five ceiling fans, sun protected carport, and a welcoming front porch framed by Zoysia grass and Christmas palms. Located on a quiet two block street with sidewalks and ample off street parking, the property is just half a block from the Lake McKillip boat ramp, offering access to the Atlantic and Gulf. Two kayaks are included. Shopping, restaurants, schools, and medical offices are conveniently nearby.

2823 Patterson Ave, Key West

$889,000

Charming Old Town Key West Cottage with Private Pool & Rooftop Deck Welcome to 1116 Eaton Street, Key West, Florida 33040--a charming 2-bedroom, 1-bathroom single-family cottage in the heart of Old Town Key West. This beautifully maintained 749 sq. ft. home combines classic island character with comfortable living and exceptional outdoor spaces, including a private heated pool and rooftop deck. Inside, the efficient floor plan is filled with natural light and features inviting living spaces and two bedrooms positioned for privacy. The kitchen and living area flow naturally together, creating a comfortable setting for everyday living or entertaining. Step outside to enjoy your private pool and multiple outdoor living spaces. The heated pool provides a refreshing place to relax, while the rooftop deck offers an elevated setting for morning coffee, sunset drinks, dining, or entertaining. The location is exceptionally walkable, with convenient access to Duval Street, historic architecture, restaurants, galleries, shopping, nightlife, the Key West Seaport, and other Old Town destinations. Enjoy the privacy of a residential cottage while remaining close to the energy and attractions that make Key West so desirable. Whether you're searching for a full-time residence, second home, or investment property, this **Key West home with a private pool** offers a rare combination of location, outdoor living, and Old Town charm. Highlights: 2 bedrooms | 1 bathroom | 749 sq. ft. | Private heated pool | Rooftop deck | Multiple outdoor living spaces | Single-family home | Highly walkable Old Town location | Under $1 million. Experience the charm and convenience of Old Town Key West at 1116 Eaton Street.

2 Beds ⋅ 1 Baths ⋅ 621609 MLS

Charming Old Town Key West Cottage with Private Pool & Rooftop Deck Welcome to 1116 Eaton Street, Key West, Florida 33040--a charming 2-bedroom, 1-bathroom single-family cottage in the heart of Old Town Key West. This beautifully maintained 749 sq. ft. home combines classic island character with comfortable living and exceptional outdoor spaces, including a private heated pool and rooftop deck. Inside, the efficient floor plan is filled with natural light and features inviting living spaces and two bedrooms positioned for privacy. The kitchen and living area flow naturally together, creating a comfortable setting for everyday living or entertaining. Step outside to enjoy your private pool and multiple outdoor living spaces. The heated pool provides a refreshing place to relax, while the rooftop deck offers an elevated setting for morning coffee, sunset drinks, dining, or entertaining. The location is exceptionally walkable, with convenient access to Duval Street, historic architecture, restaurants, galleries, shopping, nightlife, the Key West Seaport, and other Old Town destinations. Enjoy the privacy of a residential cottage while remaining close to the energy and attractions that make Key West so desirable. Whether you're searching for a full-time residence, second home, or investment property, this **Key West home with a private pool** offers a rare combination of location, outdoor living, and Old Town charm. Highlights: 2 bedrooms | 1 bathroom | 749 sq. ft. | Private heated pool | Rooftop deck | Multiple outdoor living spaces | Single-family home | Highly walkable Old Town location | Under $1 million. Experience the charm and convenience of Old Town Key West at 1116 Eaton Street.

1116 Eaton St, Key West

$3,795,000

Rare Old Town mixed-use opportunity at 1011 Whitehead Street, just steps from Duval Street, the Key West Lighthouse and the Hemingway Home. This historic property features three beautifully updated, furnished one-bedroom residences, each with its own kitchen and transient rental license, allowing the units to be rented individually or together. Private patios and balconies add classic Key West charm, while a street-level commercial storefront provides an additional income-producing component. With three valuable transient licenses, flexible use and an iconic walkable location, this is a unique opportunity to own a distinctive piece of Key West.

3 Beds ⋅ 5 Baths ⋅ 621561 MLS

Rare Old Town mixed-use opportunity at 1011 Whitehead Street, just steps from Duval Street, the Key West Lighthouse and the Hemingway Home. This historic property features three beautifully updated, furnished one-bedroom residences, each with its own kitchen and transient rental license, allowing the units to be rented individually or together. Private patios and balconies add classic Key West charm, while a street-level commercial storefront provides an additional income-producing component. With three valuable transient licenses, flexible use and an iconic walkable location, this is a unique opportunity to own a distinctive piece of Key West.

1011 Whitehead St, Key West

$6,449,000

Some Key West homes are historic because they are old. 1311 Truman Avenue is historic because of who built it, who gathered within its walls, and who saved it. Its front door came from the Old Southernmost House. Past it, Dade County pine flows through every room, chandeliers light high ceilings on both floors, and the original staircase still rises where it has stood for more than a century. A second staircase toward the rear, also original to the house, recalls the scale on which it was built. Outside, sweeping double-story porches wrap the Victorian-influenced home, set on a third of an acre. The house was built at the turn of the twentieth century by Benjamin Douglas Trevor and his wife, Mary Fogarty Trevor. Mr. Trevor founded Key West's first Steam Laundry and in 1903 became Mayor of Key West. In the decades that followed, the house became home to the Key West Woman's Club and later served as a church. In 1975 two prominent local antique dealers purchased it and returned it to its original glory, and their work received the first award for an excellent restoration given by the Old Island Restoration Foundation. That restoration still defines the house. The original windows remain, along with the moldings and trim, and verandas open to the grounds from both floors. A large covered porch offers room for both dining and living, with views over the refinished pool and the guest cottage. Over the past decade, the current owners have carried that stewardship forward. A magnificent tropical garden and a stunning pool now grace the 14,490-square-foot lot. Every bathroom has been updated and finished in a fine selection of marble, granite, and quartz, and the kitchen and appliances have been updated, bringing modern comfort to a house whose history remains its defining feature. Built by a mayor, gathered in by the Woman's Club, and saved by the restoration that set the standard for Old Town, 1311 Truman Avenue is ready for the next chapter of its story.

7 Beds ⋅ 8 Baths ⋅ 621544 MLS

Some Key West homes are historic because they are old. 1311 Truman Avenue is historic because of who built it, who gathered within its walls, and who saved it. Its front door came from the Old Southernmost House. Past it, Dade County pine flows through every room, chandeliers light high ceilings on both floors, and the original staircase still rises where it has stood for more than a century. A second staircase toward the rear, also original to the house, recalls the scale on which it was built. Outside, sweeping double-story porches wrap the Victorian-influenced home, set on a third of an acre. The house was built at the turn of the twentieth century by Benjamin Douglas Trevor and his wife, Mary Fogarty Trevor. Mr. Trevor founded Key West's first Steam Laundry and in 1903 became Mayor of Key West. In the decades that followed, the house became home to the Key West Woman's Club and later served as a church. In 1975 two prominent local antique dealers purchased it and returned it to its original glory, and their work received the first award for an excellent restoration given by the Old Island Restoration Foundation. That restoration still defines the house. The original windows remain, along with the moldings and trim, and verandas open to the grounds from both floors. A large covered porch offers room for both dining and living, with views over the refinished pool and the guest cottage. Over the past decade, the current owners have carried that stewardship forward. A magnificent tropical garden and a stunning pool now grace the 14,490-square-foot lot. Every bathroom has been updated and finished in a fine selection of marble, granite, and quartz, and the kitchen and appliances have been updated, bringing modern comfort to a house whose history remains its defining feature. Built by a mayor, gathered in by the Woman's Club, and saved by the restoration that set the standard for Old Town, 1311 Truman Avenue is ready for the next chapter of its story.

1311 Truman Ave, Key West

$3,700,000

This home has everything you need to enjoy the Key West lifestyle! With approximately 2,800 sq. ft. of living space and a 6-foot privacy fence surrounding the large property, there's plenty of room to entertain both inside and out. The kitchen features Sub-Zero and KitchenAid appliances and flows right into the main living area, making it perfect for everyday living and entertaining. The home also offers a full laundry room plus a bonus mudroom for extra storage and convenience. Outside is where this home really shines! Enjoy a covered deck area, large heated pool, and boating canal with a 30,000-lb. boat lift and ice machine. You're just minutes from the channel--no idling 1-2 miles down the canal like with many other homes. There's also covered parking and a garage with plenty of room to store all your toys. Best of all, this home is being sold turnkey and even includes a golf cart! Come see what sets this home apart from anything else on the market!

5 Beds ⋅ 5 Baths ⋅ 621515 MLS

This home has everything you need to enjoy the Key West lifestyle! With approximately 2,800 sq. ft. of living space and a 6-foot privacy fence surrounding the large property, there's plenty of room to entertain both inside and out. The kitchen features Sub-Zero and KitchenAid appliances and flows right into the main living area, making it perfect for everyday living and entertaining. The home also offers a full laundry room plus a bonus mudroom for extra storage and convenience. Outside is where this home really shines! Enjoy a covered deck area, large heated pool, and boating canal with a 30,000-lb. boat lift and ice machine. You're just minutes from the channel--no idling 1-2 miles down the canal like with many other homes. There's also covered parking and a garage with plenty of room to store all your toys. Best of all, this home is being sold turnkey and even includes a golf cart! Come see what sets this home apart from anything else on the market!

3728 Flagler Ave, Key West

$4,995,000

Where Casa Marina Charm Meets Modern Island Living. Set on an expansive 10,000 sq. ft corner lot in prestigious Casa Marina, one of Key West's most sought-after neighborhoods, this fully renovated 4-bedroom, 3-bath residence offers nearly 2,100 sq. ft of thoughtfully designed living space just moments from the Atlantic shoreline and the charm of Old Town. A comprehensive 2020 renovation transformed the home from top to bottom, delivering vaulted ceilings, energy-efficient LED lighting, and all-new hurricane-rated impact windows and doors that fill the interior with natural light. The open floor plan flows effortlessly between living, dining, and kitchen spaces, making it ideal for both everyday living and entertaining. At the heart of the home, the chef's kitchen features top-of-the-line Dacor appliances and custom bespoke cabinetry. The private primary suite is tucked at the rear of the home with an ensuite bath and sliding glass doors that open directly to the lanai. Each additional bedroom includes built-in closets, offering comfort and flexibility for guests or a home office. Outdoors, a custom heated in-ground pool with a soothing water feature is surrounded by elegant travertine decking and a spacious covered patio, creating a private tropical retreat for relaxing or hosting under the Key West sky. The low-maintenance front yard features artificial turf and landscape lighting that showcases the tropical foliage after dark. Peace of mind comes standard with a whole-house generator, 2-zone central A/C with linear vents, and a new standing seam metal roof that may qualify for wind insurance credits. A rare one-car garage and ample off-street parking complete this exceptional Casa Marina offering.

4 Beds ⋅ 3 Baths ⋅ 621521 MLS

Where Casa Marina Charm Meets Modern Island Living. Set on an expansive 10,000 sq. ft corner lot in prestigious Casa Marina, one of Key West's most sought-after neighborhoods, this fully renovated 4-bedroom, 3-bath residence offers nearly 2,100 sq. ft of thoughtfully designed living space just moments from the Atlantic shoreline and the charm of Old Town. A comprehensive 2020 renovation transformed the home from top to bottom, delivering vaulted ceilings, energy-efficient LED lighting, and all-new hurricane-rated impact windows and doors that fill the interior with natural light. The open floor plan flows effortlessly between living, dining, and kitchen spaces, making it ideal for both everyday living and entertaining. At the heart of the home, the chef's kitchen features top-of-the-line Dacor appliances and custom bespoke cabinetry. The private primary suite is tucked at the rear of the home with an ensuite bath and sliding glass doors that open directly to the lanai. Each additional bedroom includes built-in closets, offering comfort and flexibility for guests or a home office. Outdoors, a custom heated in-ground pool with a soothing water feature is surrounded by elegant travertine decking and a spacious covered patio, creating a private tropical retreat for relaxing or hosting under the Key West sky. The low-maintenance front yard features artificial turf and landscape lighting that showcases the tropical foliage after dark. Peace of mind comes standard with a whole-house generator, 2-zone central A/C with linear vents, and a new standing seam metal roof that may qualify for wind insurance credits. A rare one-car garage and ample off-street parking complete this exceptional Casa Marina offering.

1100 Johnson St, Key West

$1,399,000

Situated on a spacious corner lot in desirable Midtown West, 1221 Ashby Street offers the perfect blend of comfort, privacy, and island living. The main residence features 2 bedrooms, 2 bathrooms, and inviting living spaces, while a separate 1-bedroom, 1-bathroom poolside cottage provides additional flexibility for guests or extended family. Together, the two structures offer 1,374 square feet of living space. The oversized outdoor area is designed for enjoying the Key West lifestyle, featuring a large swimming pool, spacious decking, lounge chairs, umbrellas, and an outdoor dining area ideal for entertaining. Covered off-street parking adds convenience to this property's many desirable features. Recently updated and ready for its next owner, this property offers a fantastic opportunity to enjoy island living just minutes from Key West's famous restaurants, bars, and attractions.

3 Beds ⋅ 3 Baths ⋅ 621518 MLS

Situated on a spacious corner lot in desirable Midtown West, 1221 Ashby Street offers the perfect blend of comfort, privacy, and island living. The main residence features 2 bedrooms, 2 bathrooms, and inviting living spaces, while a separate 1-bedroom, 1-bathroom poolside cottage provides additional flexibility for guests or extended family. Together, the two structures offer 1,374 square feet of living space. The oversized outdoor area is designed for enjoying the Key West lifestyle, featuring a large swimming pool, spacious decking, lounge chairs, umbrellas, and an outdoor dining area ideal for entertaining. Covered off-street parking adds convenience to this property's many desirable features. Recently updated and ready for its next owner, this property offers a fantastic opportunity to enjoy island living just minutes from Key West's famous restaurants, bars, and attractions.

1221 Ashby St, Key West

$1,895,000

Ideally located just two blocks from the beach, this beautifully renovated Key West residence blends island living, modern comfort, and plenty of space to make it your own. Set on an expansive 6,000-square-foot corner lot, the home offers more than 2,200 square feet of living space in one of Key West's most desirable residential neighborhoods. Walk to the beach and iconic White Street Pier, along with nearby pickleball courts, playgrounds, the weekly artisan market, Bayview Park, and Fausto's Food Palace. Local favorites including Salute! On The Beach and Louie's Backyard are also just minutes away. At the heart of the home is a brand-new kitchen featuring custom cabinetry, stainless steel appliances, quartz countertops, and a fresh, sophisticated finish. Thoughtful renovations throughout provide a beautifully updated foundation while leaving room for the next owners to add their own personal style. Major improvements include a new roof, impact-rated windows and doors, updated HVAC, lighting, interior and exterior paint, water heater, and other essential systems--offering peace of mind with many of the home's major components already addressed. The property also has no history of flooding, an especially valuable feature for island living. Outside, the oversized corner lot offers exceptional potential to create a private Key West retreat, with ample room for a pool, tropical landscaping, and outdoor entertaining areas. Ample street parking is available, along with off-street parking suitable for a small sedan or golf cart. With more than 2,200 square feet of living space, a substantial corner lot, extensive improvements, and an exceptional location just two blocks from the Atlantic, this Rose Street residence presents a rare opportunity to create your own piece of Key West paradise.

4 Beds ⋅ 4 Baths ⋅ 621516 MLS

Ideally located just two blocks from the beach, this beautifully renovated Key West residence blends island living, modern comfort, and plenty of space to make it your own. Set on an expansive 6,000-square-foot corner lot, the home offers more than 2,200 square feet of living space in one of Key West's most desirable residential neighborhoods. Walk to the beach and iconic White Street Pier, along with nearby pickleball courts, playgrounds, the weekly artisan market, Bayview Park, and Fausto's Food Palace. Local favorites including Salute! On The Beach and Louie's Backyard are also just minutes away. At the heart of the home is a brand-new kitchen featuring custom cabinetry, stainless steel appliances, quartz countertops, and a fresh, sophisticated finish. Thoughtful renovations throughout provide a beautifully updated foundation while leaving room for the next owners to add their own personal style. Major improvements include a new roof, impact-rated windows and doors, updated HVAC, lighting, interior and exterior paint, water heater, and other essential systems--offering peace of mind with many of the home's major components already addressed. The property also has no history of flooding, an especially valuable feature for island living. Outside, the oversized corner lot offers exceptional potential to create a private Key West retreat, with ample room for a pool, tropical landscaping, and outdoor entertaining areas. Ample street parking is available, along with off-street parking suitable for a small sedan or golf cart. With more than 2,200 square feet of living space, a substantial corner lot, extensive improvements, and an exceptional location just two blocks from the Atlantic, this Rose Street residence presents a rare opportunity to create your own piece of Key West paradise.

1423 Rose St, Key West

$1,649,000

Pool, Parking & Location- Enjoy Old Town Key West living just two blocks from Duval Street at 615 Amelia Street. This two-bedroom, two-and-a-half-bath single family home offers inviting indoor and outdoor spaces centered around a tropical pool courtyard. The open living and dining area features wide sliding glass doors leading to a covered deck, creating an easy flow for relaxing or entertaining. Beyond the deck, lush landscaping surrounds the pool and patio, with space for outdoor dining and lounging. The kitchen offers white cabinetry, ample storage, and a windowed breakfast nook, while a vaulted ceiling gives one of the bedrooms an airy feel. The roof and windows were upgraded in 2024. Located in Flood Zone X, annual insurance costs are approximately $6,407. From morning coffee on the deck to afternoons beside the pool, this home brings together comfortable living and a convenient Old Town location.

2 Beds ⋅ 3 Baths ⋅ 621509 MLS

Pool, Parking & Location- Enjoy Old Town Key West living just two blocks from Duval Street at 615 Amelia Street. This two-bedroom, two-and-a-half-bath single family home offers inviting indoor and outdoor spaces centered around a tropical pool courtyard. The open living and dining area features wide sliding glass doors leading to a covered deck, creating an easy flow for relaxing or entertaining. Beyond the deck, lush landscaping surrounds the pool and patio, with space for outdoor dining and lounging. The kitchen offers white cabinetry, ample storage, and a windowed breakfast nook, while a vaulted ceiling gives one of the bedrooms an airy feel. The roof and windows were upgraded in 2024. Located in Flood Zone X, annual insurance costs are approximately $6,407. From morning coffee on the deck to afternoons beside the pool, this home brings together comfortable living and a convenient Old Town location.

615 Amelia St, Key West

$3,750,000

New construction, Elevated 3BD/3.5BA with heated pool and gated off-street parking on coveted Olivia Street. The Twins on Olivia is a Key West landmark reborn. The original structures, known locally as 'Olivia's Twins' and documented on the 1892 Sanborn maps, were condemned by the city and demolished. In their place, Kanga Construction has built an all-new 2,421 sq ft home on a 2,773 sq ft lot, designed with extensive guidance from Key West's HARC to honor the original twins in form and spirit. That history lives on in two separate staircases, a nod to the original pair of homes that also gives guests or family their own side of the house. All three bedrooms have ensuite baths and built-in closets, and dual-zone A/C with two whole-house dehumidifiers keeps every room comfortable year-round. French oak floors run throughout bright, open living spaces. The kitchen pairs Viking appliances, including a gas range and ice maker, with custom Hansel & Bringle cabinetry and quartz countertops. Impact-rated windows and doors, among them a custom mahogany front door with matching mahogany entry and lattice details, combine island craftsmanship with hurricane protection. Outside, ipe decking surrounds a heated pool with waterfall, set within private tropical landscaping. Off-street parking sits behind an electric gate. The home is offered fully turnkey, with a curated furniture package by local designer David Smith valued at over $150,000 plus plantation shutters throughout, all steps from Old Town's best restaurants, galleries and landmarks. Historic Key West character, built new.

3 Beds ⋅ 4 Baths ⋅ 621485 MLS

New construction, Elevated 3BD/3.5BA with heated pool and gated off-street parking on coveted Olivia Street. The Twins on Olivia is a Key West landmark reborn. The original structures, known locally as 'Olivia's Twins' and documented on the 1892 Sanborn maps, were condemned by the city and demolished. In their place, Kanga Construction has built an all-new 2,421 sq ft home on a 2,773 sq ft lot, designed with extensive guidance from Key West's HARC to honor the original twins in form and spirit. That history lives on in two separate staircases, a nod to the original pair of homes that also gives guests or family their own side of the house. All three bedrooms have ensuite baths and built-in closets, and dual-zone A/C with two whole-house dehumidifiers keeps every room comfortable year-round. French oak floors run throughout bright, open living spaces. The kitchen pairs Viking appliances, including a gas range and ice maker, with custom Hansel & Bringle cabinetry and quartz countertops. Impact-rated windows and doors, among them a custom mahogany front door with matching mahogany entry and lattice details, combine island craftsmanship with hurricane protection. Outside, ipe decking surrounds a heated pool with waterfall, set within private tropical landscaping. Off-street parking sits behind an electric gate. The home is offered fully turnkey, with a curated furniture package by local designer David Smith valued at over $150,000 plus plantation shutters throughout, all steps from Old Town's best restaurants, galleries and landmarks. Historic Key West character, built new.

1010 Olivia St, Key West

$1,100,000

Welcome to your dream home in the heart of Key West's MidTown! This beautifully updated 3-bedroom, 2-bathroom residence blends modern comfort with island charm. Step inside to a spacious, open-concept living area designed for both relaxing and entertaining. The true highlight is the private backyard oasis -- featuring a sparkling pool surrounded by fresh tropical landscaping, an expansive deck, and plenty of room for outdoor dining and lounging. Whether hosting guests or enjoying a quiet evening under the palms, this outdoor retreat feels like your own private paradise. Recent renovations provide peace of mind, including new impact windows and doors, Hardie board siding, and other thoughtful upgrades. Off-street parking adds everyday convenience. Perfectly located in the desirable MidTown neighborhood, this home keeps you close to shopping, dining, and all the best of Key West living. Don't miss this opportunity to own a beautifully updated slice of paradise in Key West -- schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ 621482 MLS

Welcome to your dream home in the heart of Key West's MidTown! This beautifully updated 3-bedroom, 2-bathroom residence blends modern comfort with island charm. Step inside to a spacious, open-concept living area designed for both relaxing and entertaining. The true highlight is the private backyard oasis -- featuring a sparkling pool surrounded by fresh tropical landscaping, an expansive deck, and plenty of room for outdoor dining and lounging. Whether hosting guests or enjoying a quiet evening under the palms, this outdoor retreat feels like your own private paradise. Recent renovations provide peace of mind, including new impact windows and doors, Hardie board siding, and other thoughtful upgrades. Off-street parking adds everyday convenience. Perfectly located in the desirable MidTown neighborhood, this home keeps you close to shopping, dining, and all the best of Key West living. Don't miss this opportunity to own a beautifully updated slice of paradise in Key West -- schedule your private showing today!

2911 Seidenberg Ave, Key West

$1,595,000

LOCATION! Situated on Garrison Bight, across the canal from the Key West Yacht Club, 5 Hilton Haven Dr. provides the best boating access on Key West. Tremendous opportunity for a buyer with a vision. The 4-bedroom, 4.5 bath, 2,027 sq. ft. home that is currently divided into 4 separate units in need of extensive repair. Or this home could be a good candidate for rebuilding as your single-family dream home with a pool, separate pool house, and 60' of dockage. Tucked away on one of Key West's few private drives, the home enjoys limited traffic and added privacy. Equipped with 2 electric meters and 9,058 sq. ft. lot, this property offers options and flexibility for bringing your vision to life.

4 Beds ⋅ 5 Baths ⋅ 621480 MLS

LOCATION! Situated on Garrison Bight, across the canal from the Key West Yacht Club, 5 Hilton Haven Dr. provides the best boating access on Key West. Tremendous opportunity for a buyer with a vision. The 4-bedroom, 4.5 bath, 2,027 sq. ft. home that is currently divided into 4 separate units in need of extensive repair. Or this home could be a good candidate for rebuilding as your single-family dream home with a pool, separate pool house, and 60' of dockage. Tucked away on one of Key West's few private drives, the home enjoys limited traffic and added privacy. Equipped with 2 electric meters and 9,058 sq. ft. lot, this property offers options and flexibility for bringing your vision to life.

5 Hilton Haven Dr, Key West

$3,295,000

Discover the perfect blend of transient investment potential and coastal charm on Atlantic Boulevard. Just steps from the beach, this exceptional property offers a truly enchanting lifestyle with a distinctive boho-coastal aesthetic. The Atlantis House featuring five bedrooms and four bathrooms across three thoughtfully curated living spaces, this one-of-a-kind compound combines character, comfort, and style with an exciting opportunity for transient rental income. The primary residence is an exquisite 3-BR/2-BA monthly rental boasting a light-filled, open-concept floor plan for effortless island entertaining. You are welcomed into a mosaic-tiled foyer featuring whimsical swinging hammock chairs and a charming custom scooter coffee bar, flowing into spacious living areas adorned with timeless terrazzo floors. The heart of the home is a true gourmet kitchen, featuring a large island, pristine white quartz countertops, and separate Sub-Zero refrigerator and freezer. The main level offers two luxurious bedrooms opening to a beautifully landscaped fenced yard with a bistro patio. A spiral staircase leads upstairs to a third bedroom--a spectacular oasis with open water views. This level features dual sliding doors opening onto a magical, Trex rooftop terrace with a dining pergola and views of the Atlantic. It is the perfect perch to watch the sunrise with coffee in hand and return for the sunset. Around the corner are two detached, transient-licensed 1BR/1BA guest suites with dedicated parking. Both offer tasteful decor and private access to a backyard oasis with a large shared deck shaded by towering palms. Live the ultimate Key West lifestyle, a stone's throw from launching your kayak at the beach and a one-minute walk from the iconic White Street Pier. The Atlantis House conveys with its own house-made Atlantis Key Lime Pie recipe, passed from the former owner to the new owner, a tradition carried for more than 30 years. A one-of-a-kind treasure!

5 Beds ⋅ 4 Baths ⋅ 621476 MLS

Discover the perfect blend of transient investment potential and coastal charm on Atlantic Boulevard. Just steps from the beach, this exceptional property offers a truly enchanting lifestyle with a distinctive boho-coastal aesthetic. The Atlantis House featuring five bedrooms and four bathrooms across three thoughtfully curated living spaces, this one-of-a-kind compound combines character, comfort, and style with an exciting opportunity for transient rental income. The primary residence is an exquisite 3-BR/2-BA monthly rental boasting a light-filled, open-concept floor plan for effortless island entertaining. You are welcomed into a mosaic-tiled foyer featuring whimsical swinging hammock chairs and a charming custom scooter coffee bar, flowing into spacious living areas adorned with timeless terrazzo floors. The heart of the home is a true gourmet kitchen, featuring a large island, pristine white quartz countertops, and separate Sub-Zero refrigerator and freezer. The main level offers two luxurious bedrooms opening to a beautifully landscaped fenced yard with a bistro patio. A spiral staircase leads upstairs to a third bedroom--a spectacular oasis with open water views. This level features dual sliding doors opening onto a magical, Trex rooftop terrace with a dining pergola and views of the Atlantic. It is the perfect perch to watch the sunrise with coffee in hand and return for the sunset. Around the corner are two detached, transient-licensed 1BR/1BA guest suites with dedicated parking. Both offer tasteful decor and private access to a backyard oasis with a large shared deck shaded by towering palms. Live the ultimate Key West lifestyle, a stone's throw from launching your kayak at the beach and a one-minute walk from the iconic White Street Pier. The Atlantis House conveys with its own house-made Atlantis Key Lime Pie recipe, passed from the former owner to the new owner, a tradition carried for more than 30 years. A one-of-a-kind treasure!

1401 Atlantic Blvd, Key West

$799,000

Welcome to 2506 Seidenberg Avenue, a spacious 3-bedroom, 3-bath home offering 1,922 square feet of living space in the heart of Midtown Key West. Framed by tropical landscaping and a classic white picket fence, this home offers plenty of space and a flexible layout for comfortable island living. The main living area flows into a large eat-in kitchen featuring abundant cabinetry, stainless steel appliances, generous counter space, and plenty of room for dining and entertaining. Three bedrooms and three full baths provide ample accommodations, while additional living space at the rear of the property offers added flexibility for guests, a home office, den, or private retreat. A garage provides valuable parking and storage. Centrally located just minutes from Old Town, beaches, shopping, dining, and all that Key West has to offer. With nearly 2,000 square feet, versatile additional living space, a garage, and a convenient Midtown location, 2506 Seidenberg Avenue presents a unique opportunity to make a Key West home your own. Owner financing may be available.

3 Beds ⋅ 3 Baths ⋅ 621467 MLS

Welcome to 2506 Seidenberg Avenue, a spacious 3-bedroom, 3-bath home offering 1,922 square feet of living space in the heart of Midtown Key West. Framed by tropical landscaping and a classic white picket fence, this home offers plenty of space and a flexible layout for comfortable island living. The main living area flows into a large eat-in kitchen featuring abundant cabinetry, stainless steel appliances, generous counter space, and plenty of room for dining and entertaining. Three bedrooms and three full baths provide ample accommodations, while additional living space at the rear of the property offers added flexibility for guests, a home office, den, or private retreat. A garage provides valuable parking and storage. Centrally located just minutes from Old Town, beaches, shopping, dining, and all that Key West has to offer. With nearly 2,000 square feet, versatile additional living space, a garage, and a convenient Midtown location, 2506 Seidenberg Avenue presents a unique opportunity to make a Key West home your own. Owner financing may be available.

2506 Seidenberg Ave, Key West

$6,895,000

The Autograph House is a newly built, architect-designed luxury property in the heart of Old Town Key West, ideally positioned just one block from Duval Street and the island's most celebrated attractions. Blending refined modern design with the relaxed elegance of Key West, this exceptional property offers a rare combination of sophistication, privacy and walkable convenience. The home encompasses a stunning two-story Main Residence with four private bedroom suites, each featuring an en-suite bath with custom millwork, along with a beautifully appointed two-bedroom, two-bath Guest Cottage. Together, the residences create an exceptional six-bedroom, six-bathroom estate ideal for multi-generational living, extended stays, or entertaining. The Main Residence features an expansive open-concept living, dining, and chef's kitchen with premium Miele appliances, Fisher & Paykel column refrigeration, custom cabinetry, and a generous island. Floor-to-ceiling impact-rated sliding glass doors open seamlessly to a covered outdoor living and entertaining area, complete with lounge seating, a fully equipped outdoor kitchen, grill, beverage refrigerator, and dining space. Lush tropical landscaping surrounds a private heated pool and separate hot tub. The Main Residence pool features a waterfall and built-in bench seating, while the Guest Cottage offers its own private spa hot tub. An outdoor shower and secluded garden spaces further enhance the resort-like setting. Throughout the property, custom finishes, beautiful furnishings, Sonos audio, and full-size laundry facilities reflect an exceptional level of comfort and attention to detail. Perfectly situated in Old Town's X-Flood Zone, this home places Duval Street, Mallory Square, world-class dining, galleries, shopping, beaches, and iconic Key West landmarks just moments away. A rare opportunity to own a turnkey luxury compound in one of Key West's most coveted locations. Call today for a showing!

6 Beds ⋅ 7 Baths ⋅ 621466 MLS

The Autograph House is a newly built, architect-designed luxury property in the heart of Old Town Key West, ideally positioned just one block from Duval Street and the island's most celebrated attractions. Blending refined modern design with the relaxed elegance of Key West, this exceptional property offers a rare combination of sophistication, privacy and walkable convenience. The home encompasses a stunning two-story Main Residence with four private bedroom suites, each featuring an en-suite bath with custom millwork, along with a beautifully appointed two-bedroom, two-bath Guest Cottage. Together, the residences create an exceptional six-bedroom, six-bathroom estate ideal for multi-generational living, extended stays, or entertaining. The Main Residence features an expansive open-concept living, dining, and chef's kitchen with premium Miele appliances, Fisher & Paykel column refrigeration, custom cabinetry, and a generous island. Floor-to-ceiling impact-rated sliding glass doors open seamlessly to a covered outdoor living and entertaining area, complete with lounge seating, a fully equipped outdoor kitchen, grill, beverage refrigerator, and dining space. Lush tropical landscaping surrounds a private heated pool and separate hot tub. The Main Residence pool features a waterfall and built-in bench seating, while the Guest Cottage offers its own private spa hot tub. An outdoor shower and secluded garden spaces further enhance the resort-like setting. Throughout the property, custom finishes, beautiful furnishings, Sonos audio, and full-size laundry facilities reflect an exceptional level of comfort and attention to detail. Perfectly situated in Old Town's X-Flood Zone, this home places Duval Street, Mallory Square, world-class dining, galleries, shopping, beaches, and iconic Key West landmarks just moments away. A rare opportunity to own a turnkey luxury compound in one of Key West's most coveted locations. Call today for a showing!

317 Whitehead St, Key West

$4,300,000

There is a certain rhythm to life in Key West. Mornings begin outside, friends have a way of staying longer than planned, and some of the best evenings never make it past the backyard. 1614 Washington Street was designed for exactly that kind of life. Natural light, high ceilings, and an easy connection to the outdoors give the home an immediate sense of openness. The main living spaces flow naturally toward the pool and tropical garden, creating a setting that works just as well for a quiet morning at home as it does for dinner with friends that stretches late into the evening. The heated and chilled pool features two distinct levels--a shallow splash deck and a deeper swimming area--connected by cascading water features and surrounded by mature tropical landscaping that feels remarkably private. The floor plan understands that guests are part of island life, but privacy still matters. The first-floor primary suite creates a comfortable retreat for the owners, while upstairs, three en-suite bedrooms surround their own den and lounge. Family and friends can settle in, unpack, and have a space of their own rather than simply occupying yours. Behind that relaxed lifestyle is a house designed to make living here easier. Award-winning local architect Matthew Stratton brought together solid masonry construction, impact-rated windows and doors, solar power with Tesla battery storage, an EV charger, custom cabinetry, quartz surfaces, and thoughtful systems chosen for the realities of coastal living. The technology is there when you need it and nearly invisible when you don't. Morning walks, bike rides, the beach, neighborhood restaurants, galleries, and everything that makes Key West unlike anywhere else are simply part of the day. 1614 Washington invites you to open the doors, gather the people you love, jump in the pool, stay for dinner, and make yourself at home. Because ultimately, the best luxury isn't about having more. It's having a home that lets you live well.

4 Beds ⋅ 5 Baths ⋅ 621463 MLS

There is a certain rhythm to life in Key West. Mornings begin outside, friends have a way of staying longer than planned, and some of the best evenings never make it past the backyard. 1614 Washington Street was designed for exactly that kind of life. Natural light, high ceilings, and an easy connection to the outdoors give the home an immediate sense of openness. The main living spaces flow naturally toward the pool and tropical garden, creating a setting that works just as well for a quiet morning at home as it does for dinner with friends that stretches late into the evening. The heated and chilled pool features two distinct levels--a shallow splash deck and a deeper swimming area--connected by cascading water features and surrounded by mature tropical landscaping that feels remarkably private. The floor plan understands that guests are part of island life, but privacy still matters. The first-floor primary suite creates a comfortable retreat for the owners, while upstairs, three en-suite bedrooms surround their own den and lounge. Family and friends can settle in, unpack, and have a space of their own rather than simply occupying yours. Behind that relaxed lifestyle is a house designed to make living here easier. Award-winning local architect Matthew Stratton brought together solid masonry construction, impact-rated windows and doors, solar power with Tesla battery storage, an EV charger, custom cabinetry, quartz surfaces, and thoughtful systems chosen for the realities of coastal living. The technology is there when you need it and nearly invisible when you don't. Morning walks, bike rides, the beach, neighborhood restaurants, galleries, and everything that makes Key West unlike anywhere else are simply part of the day. 1614 Washington invites you to open the doors, gather the people you love, jump in the pool, stay for dinner, and make yourself at home. Because ultimately, the best luxury isn't about having more. It's having a home that lets you live well.

1614 Washington St, Key West

$2,475,000

Discover the charm of what was once a carriage house and now a single-level home nestled in the highly desirable Meadows neighborhood of Old Town Key West. This inviting 3-bedroom, 2-bath residence blends historic character with modern updates, offering the quintessential island lifestyle. Effortless indoor-outdoor living defines this home, which features an open, airy feel that flows seamlessly to a private backyard oasis. The renovated kitchen features quartz countertops, modern finishes perfect for entertaining or everyday living. A versatile bonus loft provides the ideal space for a home office. Step outside to your own tropical retreat, complete with a sparkling pool surrounded by a spacious brick patio, cabana bar, fabulous outdoor shower and mature landscaping that creates privacy and a lush island ambiance. Topped off with off-street parking, whole house generator, x flood zone and close proximity to everything that makes Key West living so special, while still providing a peaceful neighborhood setting. This is truly a gem waiting to become your tropical island home!

3 Beds ⋅ 2 Baths ⋅ 621462 MLS

Discover the charm of what was once a carriage house and now a single-level home nestled in the highly desirable Meadows neighborhood of Old Town Key West. This inviting 3-bedroom, 2-bath residence blends historic character with modern updates, offering the quintessential island lifestyle. Effortless indoor-outdoor living defines this home, which features an open, airy feel that flows seamlessly to a private backyard oasis. The renovated kitchen features quartz countertops, modern finishes perfect for entertaining or everyday living. A versatile bonus loft provides the ideal space for a home office. Step outside to your own tropical retreat, complete with a sparkling pool surrounded by a spacious brick patio, cabana bar, fabulous outdoor shower and mature landscaping that creates privacy and a lush island ambiance. Topped off with off-street parking, whole house generator, x flood zone and close proximity to everything that makes Key West living so special, while still providing a peaceful neighborhood setting. This is truly a gem waiting to become your tropical island home!

1212 Olivia St, Key West

$2,145,000

Completed in 2025, this brand-new, elevated two-story home rises above the surrounding homes and is built above flood level. Excellent location close to the beach. Category 5 hurricane-rated construction, impact windows and doors, and Hardie board siding combine coastal style with storm protection. The home offers 3 bedrooms and 3 bathrooms, plus an office currently set up with bunk beds as a fourth sleeping space. Separate laundry room. The backyard is a gorgeous tropical retreat. A large heated pool and spa are surrounded by a gorgeous stone deck, lush landscaping and dramatic evening lighting. A huge poolside Tiki hut creates a spectacular setting for shaded dining, lounging and entertaining, while a putting green adds to the fun. Generous gathering areas and a completely fenced yard make this outdoor oasis perfect for sunny afternoons and unforgettable evenings beneath the palms. Inside, bright, open living and dining spaces flow into a beautiful kitchen with white cabinetry, stainless steel appliances, a blue tile backsplash and a generous island with seating. Balconies extend the living space outdoors. Beneath the home, a large covered area offers room to watch sports, relax and entertain, or serve as a carport. A permitted downstairs enclosure provides valuable storage and pool cabana. New construction, an elevated setting and an exceptional backyard come together in one remarkable property. Don't miss your opportunity to make this tropical escape your own!

3 Beds ⋅ 2 Baths ⋅ 621461 MLS

Completed in 2025, this brand-new, elevated two-story home rises above the surrounding homes and is built above flood level. Excellent location close to the beach. Category 5 hurricane-rated construction, impact windows and doors, and Hardie board siding combine coastal style with storm protection. The home offers 3 bedrooms and 3 bathrooms, plus an office currently set up with bunk beds as a fourth sleeping space. Separate laundry room. The backyard is a gorgeous tropical retreat. A large heated pool and spa are surrounded by a gorgeous stone deck, lush landscaping and dramatic evening lighting. A huge poolside Tiki hut creates a spectacular setting for shaded dining, lounging and entertaining, while a putting green adds to the fun. Generous gathering areas and a completely fenced yard make this outdoor oasis perfect for sunny afternoons and unforgettable evenings beneath the palms. Inside, bright, open living and dining spaces flow into a beautiful kitchen with white cabinetry, stainless steel appliances, a blue tile backsplash and a generous island with seating. Balconies extend the living space outdoors. Beneath the home, a large covered area offers room to watch sports, relax and entertain, or serve as a carport. A permitted downstairs enclosure provides valuable storage and pool cabana. New construction, an elevated setting and an exceptional backyard come together in one remarkable property. Don't miss your opportunity to make this tropical escape your own!

1716 Laird St, Key West

$6,450,000

A rare opportunity in the heart of Old Town Key West's coveted Seaport neighborhood, this exceptional multi-residence property combines the charm and architectural character of historic Key West with the comfort, quality and convenience of newly constructed living. Thoughtfully designed to retain the home's traditional aesthetic, the property offers remarkable flexibility as a private compound, multigenerational residence or sophisticated investment property, with beautifully finished interiors, resort-style outdoor spaces and exceptional parking for the neighborhood. The main residence is a legal triplex, with each home offering its own privacy and character and 3 off street parking spaces. At the front of the property, a charming 1-bedroom, 1-bath residence occupies the first floor and opens to a generous covered porch and private yard. A separate side entrance leads to a distinctive three-story, 2-bedroom, 2.5-bath residence with its own side porch and upper levels overlooking the front of the property. Occupying the rear portion of the main house is the largest residence, a spacious 3-bedroom, 3.5-bath home arranged entirely on the main living level. Beautifully finished interiors open to a lush tropical retreat with a private pool, fountains, expansive patios, outdoor dining and multiple lounging areas. An unfinished basement offers exceptional potential for a wine cellar, tasting room or collection space. A landscaped walkway leads to a separate 1-bedroom, 1-bath cottage fronting Peacon Lane, with a private rear deck, outdoor dining area and two-car off-street parking. Importantly, the Peacon Lane residence sits on its own separate legal parcel, providing the rare flexibility for it to be owned or sold independently from the main property should a future owner ever choose to do so. Just beyond the gates, the waterfront, restaurants, galleries, shops and historic sites are all within an easy walk in one of Old Town Key West's most desirable neighborhoods.

7 Beds ⋅ 9 Baths ⋅ 621458 MLS

A rare opportunity in the heart of Old Town Key West's coveted Seaport neighborhood, this exceptional multi-residence property combines the charm and architectural character of historic Key West with the comfort, quality and convenience of newly constructed living. Thoughtfully designed to retain the home's traditional aesthetic, the property offers remarkable flexibility as a private compound, multigenerational residence or sophisticated investment property, with beautifully finished interiors, resort-style outdoor spaces and exceptional parking for the neighborhood. The main residence is a legal triplex, with each home offering its own privacy and character and 3 off street parking spaces. At the front of the property, a charming 1-bedroom, 1-bath residence occupies the first floor and opens to a generous covered porch and private yard. A separate side entrance leads to a distinctive three-story, 2-bedroom, 2.5-bath residence with its own side porch and upper levels overlooking the front of the property. Occupying the rear portion of the main house is the largest residence, a spacious 3-bedroom, 3.5-bath home arranged entirely on the main living level. Beautifully finished interiors open to a lush tropical retreat with a private pool, fountains, expansive patios, outdoor dining and multiple lounging areas. An unfinished basement offers exceptional potential for a wine cellar, tasting room or collection space. A landscaped walkway leads to a separate 1-bedroom, 1-bath cottage fronting Peacon Lane, with a private rear deck, outdoor dining area and two-car off-street parking. Importantly, the Peacon Lane residence sits on its own separate legal parcel, providing the rare flexibility for it to be owned or sold independently from the main property should a future owner ever choose to do so. Just beyond the gates, the waterfront, restaurants, galleries, shops and historic sites are all within an easy walk in one of Old Town Key West's most desirable neighborhoods.

723 Eaton St, Key West

$1,350,000

Welcome to the Sanctuary! This UPDATED/REMODELED gated single family POOL home is located on the 18th hole of the world famous Rees Jones designed Key West Golf Course. 1600 sq ft of living space with 3 bedrooms and 2.5 bathrooms. This 2 story home features an open floor plan with 9 ft ceilings and lots of windows allowing in natural light. An updated half bath is conveniently located on the first floor. The kitchen was updated with Calcutta Quartz countertops, ceramic plank tile backsplash resembling a weathered coastal wood and stainless steel Cafe appliances. Travel up the stairs with new Bamboo flooring to 3 bedrooms and 2 more updated baths. The Primary Suite features a Spa Like Escape bath with waterfall shower. French doors off the Primary Suite open to a screened balcony porch with views of tropical foliage and private pool. The pool was recently resurfaced and the pool pump and pool heater replaced. Sprinkler system also replaced. Freshly painted exterior. 24 hour security, fitness room, additional community pool are just a few of the amenities this property offers. You don't want to miss this beautiful turn key home in one of the most tranquil settings in Key West. It's a true Coastal Charmer!

3 Beds ⋅ 3 Baths ⋅ 621423 MLS

Welcome to the Sanctuary! This UPDATED/REMODELED gated single family POOL home is located on the 18th hole of the world famous Rees Jones designed Key West Golf Course. 1600 sq ft of living space with 3 bedrooms and 2.5 bathrooms. This 2 story home features an open floor plan with 9 ft ceilings and lots of windows allowing in natural light. An updated half bath is conveniently located on the first floor. The kitchen was updated with Calcutta Quartz countertops, ceramic plank tile backsplash resembling a weathered coastal wood and stainless steel Cafe appliances. Travel up the stairs with new Bamboo flooring to 3 bedrooms and 2 more updated baths. The Primary Suite features a Spa Like Escape bath with waterfall shower. French doors off the Primary Suite open to a screened balcony porch with views of tropical foliage and private pool. The pool was recently resurfaced and the pool pump and pool heater replaced. Sprinkler system also replaced. Freshly painted exterior. 24 hour security, fitness room, additional community pool are just a few of the amenities this property offers. You don't want to miss this beautiful turn key home in one of the most tranquil settings in Key West. It's a true Coastal Charmer!

197 Golf Club Dr, Key West

$1,487,000

Welcome to 2519 Staples Avenue, a fully reimagined residence in the heart of Midtown Key West, set on a rare 10,000 sq ft corner lot along one of the area's most bicyclable and desirable streets in Midtown. Recently completed renovations offer the opportunity to be the first to live in this thoughtfully rethought home, where modern upgrades meet relaxed island living. Spanning approximately 2,100 sq ft, the property features 4 bedrooms and 3.5 bathrooms, with a layout designed for both comfort and functionality. The primary suite serves as a private retreat, complete with direct access to the backyard, a spacious walk-in closet, and a beautifully appointed ensuite bathroom. Outdoor living is where this home truly stands out. A newly installed pool with elegant deck jets creates a serene, resort-style setting, fully enclosed for privacy. The new addition of a bright and airy pool room offers a seamless indoor-outdoor flow- perfect for entertaining or unwinding. There is a separate sitting and dining area for eating and lounging el fresco. Beautiful mature fruit trees provide shade and produce fruit annually. Additional upgrades include all impact windows and doors, providing peace of mind and energy efficiency throughout. New sewer and plumbing pipes to the road. New electrical and a new water heater. There is plenty of parking for a boat, a truck, a golf cart and a car. Properties offering this combination of lot size, location, and new construction-level renovations are exceptionally rare in Key West. Whether you're seeking a full-time residence, a family home, or a vacation retreat, this property delivers. House is being offered fully furnished minus personal items, art, and rugs. A true standout opportunity in Midtown, don't miss it!

4 Beds ⋅ 4 Baths ⋅ 621374 MLS

Welcome to 2519 Staples Avenue, a fully reimagined residence in the heart of Midtown Key West, set on a rare 10,000 sq ft corner lot along one of the area's most bicyclable and desirable streets in Midtown. Recently completed renovations offer the opportunity to be the first to live in this thoughtfully rethought home, where modern upgrades meet relaxed island living. Spanning approximately 2,100 sq ft, the property features 4 bedrooms and 3.5 bathrooms, with a layout designed for both comfort and functionality. The primary suite serves as a private retreat, complete with direct access to the backyard, a spacious walk-in closet, and a beautifully appointed ensuite bathroom. Outdoor living is where this home truly stands out. A newly installed pool with elegant deck jets creates a serene, resort-style setting, fully enclosed for privacy. The new addition of a bright and airy pool room offers a seamless indoor-outdoor flow- perfect for entertaining or unwinding. There is a separate sitting and dining area for eating and lounging el fresco. Beautiful mature fruit trees provide shade and produce fruit annually. Additional upgrades include all impact windows and doors, providing peace of mind and energy efficiency throughout. New sewer and plumbing pipes to the road. New electrical and a new water heater. There is plenty of parking for a boat, a truck, a golf cart and a car. Properties offering this combination of lot size, location, and new construction-level renovations are exceptionally rare in Key West. Whether you're seeking a full-time residence, a family home, or a vacation retreat, this property delivers. House is being offered fully furnished minus personal items, art, and rugs. A true standout opportunity in Midtown, don't miss it!

2519 Staples Ave, Key West

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