bestfloridakeyshomefinder.com Search Results

Steps From Duval. Worlds Away. Morning coffee on the wraparound porch. An afternoon swim beneath the waterfall. Dinner under the stars. At 813 Thomas Street, every day feels like the best kind of Key West getaway. Set on a rare double lot in Flood Zone X and completely renovated in 2025, this island-contemporary residence pairs a 3-bedroom, 2-bath main home with a brand-new 1-bed, 1-bath guest cottage, giving family and friends a private retreat of their own. Inside, soaring ceilings, sun-drenched living spaces, and hardwood floors set an elegant tone. The chef's kitchen is the showpiece, with custom cabinetry, a sculptural quartz waterfall island, and a full suite of Thermador stainless steel appliances delivering professional-caliber performance with refined style. Whether it's a quiet breakfast or a dinner party for a crowd, this kitchen is ready for it. The entire second floor belongs to the primary suite, with a private balcony, walk-in closet, and spa-style bath featuring a deep soaking tub, double vanity, and separate shower. Impact French doors open to the outdoor living spaces. A motorized pergola covers the alfresco dining area and grill station or opens to the sky at the touch of a button. More than 500 square feet of decking wraps a 15' x 22' heated completely new saltwater pool with a Cosentino Dekton waterfall, surrounded by lush tropical landscaping and an outdoor shower. Gated driveway with off-street parking for two completes this move-in ready offering. The location is pure Old Town: stroll to Blue Heaven for brunch, tour the Hemingway Home and the Key West Lighthouse, catch the sunset at Fort Zachary Taylor, snap a photo at the Southernmost Point, or explore Duval Street and Bahama Village, all within walking distance. Homes like this in the heart of Old Town are rarely available. Schedule your private showing today!

4 Beds ⋅ 3 Baths ⋅ 621693 MLS

Steps From Duval. Worlds Away. Morning coffee on the wraparound porch. An afternoon swim beneath the waterfall. Dinner under the stars. At 813 Thomas Street, every day feels like the best kind of Key West getaway. Set on a rare double lot in Flood Zone X and completely renovated in 2025, this island-contemporary residence pairs a 3-bedroom, 2-bath main home with a brand-new 1-bed, 1-bath guest cottage, giving family and friends a private retreat of their own. Inside, soaring ceilings, sun-drenched living spaces, and hardwood floors set an elegant tone. The chef's kitchen is the showpiece, with custom cabinetry, a sculptural quartz waterfall island, and a full suite of Thermador stainless steel appliances delivering professional-caliber performance with refined style. Whether it's a quiet breakfast or a dinner party for a crowd, this kitchen is ready for it. The entire second floor belongs to the primary suite, with a private balcony, walk-in closet, and spa-style bath featuring a deep soaking tub, double vanity, and separate shower. Impact French doors open to the outdoor living spaces. A motorized pergola covers the alfresco dining area and grill station or opens to the sky at the touch of a button. More than 500 square feet of decking wraps a 15' x 22' heated completely new saltwater pool with a Cosentino Dekton waterfall, surrounded by lush tropical landscaping and an outdoor shower. Gated driveway with off-street parking for two completes this move-in ready offering. The location is pure Old Town: stroll to Blue Heaven for brunch, tour the Hemingway Home and the Key West Lighthouse, catch the sunset at Fort Zachary Taylor, snap a photo at the Southernmost Point, or explore Duval Street and Bahama Village, all within walking distance. Homes like this in the heart of Old Town are rarely available. Schedule your private showing today!

813 Thomas St, Key West

$975,000

A rare find! Three bedrooms and three full bathrooms make this lovely golf course residence a standout opportunity. This home offers a comfortable and versatile layout with an updated kitchen and a convenient main level bedroom that can easily serve as a home office or guest room. A full bathroom on the main floor adds even more flexibility. Enjoy the peaceful golf course setting in a great location away from the direct path of golf balls. With its combination of space and a desirable location this is an opportunity you don't see come along often.

3 Beds ⋅ 3 Baths ⋅ 621691 MLS

A rare find! Three bedrooms and three full bathrooms make this lovely golf course residence a standout opportunity. This home offers a comfortable and versatile layout with an updated kitchen and a convenient main level bedroom that can easily serve as a home office or guest room. A full bathroom on the main floor adds even more flexibility. Enjoy the peaceful golf course setting in a great location away from the direct path of golf balls. With its combination of space and a desirable location this is an opportunity you don't see come along often.

64 Golf Club Dr, Key West

$1,500,000

Quiet Old Town lane living in this historic cottage with guest house and off street parking. The main home consists of a 1bd/1ba with an additional sleeping loft and a storage loft. The guest house sits at the rear of the property and features 1bd/1ba, kitchen, living room and loft. There is a spacious open area between the 2 structures finished in composite decking currently set up for outdoor dining and living or the ideal space for the addition of a pool. Bright and airy with vaulted ceilings throughout and multiple sets of French doors. Enjoy a newly renovated bathroom in the main house. Truly a great opportunity to dress up and expand upon a charming historic property. Or, enjoy the rustic charm of two cottages complete with kitchens on a peaceful one way Old Town driving lane. Offered fully furnished with professional management in place and future bookings to convey. Neighboring property at 832 Johnson Lane is also available for sale.

2 Beds ⋅ 1 Baths ⋅ 621685 MLS

Quiet Old Town lane living in this historic cottage with guest house and off street parking. The main home consists of a 1bd/1ba with an additional sleeping loft and a storage loft. The guest house sits at the rear of the property and features 1bd/1ba, kitchen, living room and loft. There is a spacious open area between the 2 structures finished in composite decking currently set up for outdoor dining and living or the ideal space for the addition of a pool. Bright and airy with vaulted ceilings throughout and multiple sets of French doors. Enjoy a newly renovated bathroom in the main house. Truly a great opportunity to dress up and expand upon a charming historic property. Or, enjoy the rustic charm of two cottages complete with kitchens on a peaceful one way Old Town driving lane. Offered fully furnished with professional management in place and future bookings to convey. Neighboring property at 832 Johnson Lane is also available for sale.

830 Johnson Ln, Key West

$1,500,000

Quiet Old Town lane living in this historic cottage with guest house and off street parking. The main home consists of a 1bd/1ba with an additional sleeping loft and a storage loft. The guest house sits at the rear of the property and features 1bd/1ba, kitchen, living room and loft. There is a spacious open area between the 2 structures finished in composite decking currently set up for outdoor dining and living or the ideal space for the addition of a pool. Bright and airy with vaulted ceilings throughout and multiple sets of French doors. Enjoy a newly renovated bathroom in the main house. Truly a great opportunity to dress up and expand upon a charming historic property. Or, enjoy the rustic charm of two cottages complete with kitchens on a peaceful one way Old Town driving lane. Offered fully furnished with professional management in place and future bookings to convey. Property is considered a legal duplex. Neighboring property at 832 Johnson Lane is also available for sale.

2 Beds ⋅ 2 Baths ⋅ 621684 MLS

Quiet Old Town lane living in this historic cottage with guest house and off street parking. The main home consists of a 1bd/1ba with an additional sleeping loft and a storage loft. The guest house sits at the rear of the property and features 1bd/1ba, kitchen, living room and loft. There is a spacious open area between the 2 structures finished in composite decking currently set up for outdoor dining and living or the ideal space for the addition of a pool. Bright and airy with vaulted ceilings throughout and multiple sets of French doors. Enjoy a newly renovated bathroom in the main house. Truly a great opportunity to dress up and expand upon a charming historic property. Or, enjoy the rustic charm of two cottages complete with kitchens on a peaceful one way Old Town driving lane. Offered fully furnished with professional management in place and future bookings to convey. Property is considered a legal duplex. Neighboring property at 832 Johnson Lane is also available for sale.

830 Johnson Ln, 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

$1,249,000

A RARE OLD TOWN FIND -- LOCATION, LIFESTYLE & INVESTMENT POTENTIAL! A MUST-SEE for the savvy investor, seasonal resident, or anyone dreaming of owning a piece of the Key West lifestyle! Tucked inside Windward Park, an intimate gated enclave of just 13 townhomes, this 2BD/2BA residence delivers the kind of winning combination that makes Old Town Key West so irresistible: a coveted downtown address, tropical surroundings, and a sense of privacy just one and a half blocks from the energy of Duval Street. World-class dining, lively bars, charming boutiques, and the unmistakable spirit of Key West are all just moments away. Think location, location, LOCATION -- with a tropical twist! Built in the late 1980s, Windward Park is one of the few small gated communities in the heart of Old Town. Beyond the gated entrance, a sparkling community pool and lush tropical gardens create a private oasis that feels worlds away from the bustle outside. Here, you can enjoy the best of both worlds: the excitement of downtown living and a peaceful retreat to call your own. Positioned as the first townhome on the left as you enter the community, this residence welcomes you with a charming front porch overlooking the pool and gardens. Inside, 1,120 square feet of versatile living space offer two bedrooms and two baths, with a layout that accommodates a variety of lifestyles. The ground-floor bedroom opens to its own sunny private patio -- an inviting setting for al fresco dining, entertaining, or enjoying the laid-back island atmosphere. Its convenient downstairs location also offers flexibility for guests or those who prefer a no-stairs bedroom option. THE OPPORTUNITY? 606 Truman deserves a closer look. Its central location, gated setting, community pool, off street parking spot and turnkey offering make it an appealing candidate for buyers looking to combine personal enjoyment and income potential.

2 Beds ⋅ 2 Baths ⋅ 621668 MLS

A RARE OLD TOWN FIND -- LOCATION, LIFESTYLE & INVESTMENT POTENTIAL! A MUST-SEE for the savvy investor, seasonal resident, or anyone dreaming of owning a piece of the Key West lifestyle! Tucked inside Windward Park, an intimate gated enclave of just 13 townhomes, this 2BD/2BA residence delivers the kind of winning combination that makes Old Town Key West so irresistible: a coveted downtown address, tropical surroundings, and a sense of privacy just one and a half blocks from the energy of Duval Street. World-class dining, lively bars, charming boutiques, and the unmistakable spirit of Key West are all just moments away. Think location, location, LOCATION -- with a tropical twist! Built in the late 1980s, Windward Park is one of the few small gated communities in the heart of Old Town. Beyond the gated entrance, a sparkling community pool and lush tropical gardens create a private oasis that feels worlds away from the bustle outside. Here, you can enjoy the best of both worlds: the excitement of downtown living and a peaceful retreat to call your own. Positioned as the first townhome on the left as you enter the community, this residence welcomes you with a charming front porch overlooking the pool and gardens. Inside, 1,120 square feet of versatile living space offer two bedrooms and two baths, with a layout that accommodates a variety of lifestyles. The ground-floor bedroom opens to its own sunny private patio -- an inviting setting for al fresco dining, entertaining, or enjoying the laid-back island atmosphere. Its convenient downstairs location also offers flexibility for guests or those who prefer a no-stairs bedroom option. THE OPPORTUNITY? 606 Truman deserves a closer look. Its central location, gated setting, community pool, off street parking spot and turnkey offering make it an appealing candidate for buyers looking to combine personal enjoyment and income potential.

606 Truman Ave Unit APT 1, 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

$2,250,000

Historic Old Town Charm Meets Modern Luxury. Situated next to the iconic Key West Cemetery, this legal duplex sits proudly on the island's highest point, offering an unbeatable location with unmatched peace of mind. With the original Conch House built in the late 1800s, this historic estate captures the classic romance of classic island architecture while providing a passive income opportunity. It is the ultimate configuration for a buyer looking to live the island dream in a beautiful residence while utilizing the separate unit as a legal rental to offset living costs. The main house is a spacious sanctuary featuring 4 bedrooms and 3 bathrooms. Every room blends historic character with modern comfort, offering an airy layout perfect for relaxation or entertainment. Steps away, the independent unit is a beautifully efficient studio apartment. This legal secondary unit serves as a desirable rental asset, an independent guest suite, or a private home office, adding incredible flexibility and value in a market where legal duplexes are highly coveted. While the property retains its rich late-19th-century soul, it also functions with the reliability of new construction. The entire property underwent a meticulous top-to-bottom renovation from 2022 to 2025, modernizing every major component. Upgrades include a new roof (2022), all new plumbing (2024), fully updated electrical systems (2024), attic insulation (2025), and a brand-new HVAC system (2024). Calling this property home means enjoying a quiet backdrop and unique neighborhood charm. You are just a short walk or bike ride away from world-class dining, vibrant nightlife, and pristine beaches. The driveway provides off-street parking for 1 vehicle.

5 Beds ⋅ 4 Baths ⋅ 621640 MLS

Historic Old Town Charm Meets Modern Luxury. Situated next to the iconic Key West Cemetery, this legal duplex sits proudly on the island's highest point, offering an unbeatable location with unmatched peace of mind. With the original Conch House built in the late 1800s, this historic estate captures the classic romance of classic island architecture while providing a passive income opportunity. It is the ultimate configuration for a buyer looking to live the island dream in a beautiful residence while utilizing the separate unit as a legal rental to offset living costs. The main house is a spacious sanctuary featuring 4 bedrooms and 3 bathrooms. Every room blends historic character with modern comfort, offering an airy layout perfect for relaxation or entertainment. Steps away, the independent unit is a beautifully efficient studio apartment. This legal secondary unit serves as a desirable rental asset, an independent guest suite, or a private home office, adding incredible flexibility and value in a market where legal duplexes are highly coveted. While the property retains its rich late-19th-century soul, it also functions with the reliability of new construction. The entire property underwent a meticulous top-to-bottom renovation from 2022 to 2025, modernizing every major component. Upgrades include a new roof (2022), all new plumbing (2024), fully updated electrical systems (2024), attic insulation (2025), and a brand-new HVAC system (2024). Calling this property home means enjoying a quiet backdrop and unique neighborhood charm. You are just a short walk or bike ride away from world-class dining, vibrant nightlife, and pristine beaches. The driveway provides off-street parking for 1 vehicle.

811 Olivia St, Key West

$35,000

Turnkey Restaurant Opportunity - Prime Old Town Key West Location! Excellent opportunity to take over a fully equipped restaurant in the heart of Old Town Key West! Ideally located on the corner of Eaton and Grinnell Streets, this restaurant offers excellent visibility, indoor dining space, and inviting outdoor seating. The $35,000 asking price includes all seller owned restaurant FF&E. The seller is looking for a new operator to take over the lease and acquire the existing restaurant set up. An excellent opportunity for an experienced restaurateur or entrepreneur to establish a presence in Key West without the significant upfront investment required to build out a restaurant from scratch. Continue the existing concept or introduce your own vision in this established restaurant location. Business assets and good will only; real estate is not included. Lease assignment subject to landlord approval. Bring your vision and make this Key West restaurant location your own!

2 Baths ⋅ 621634 MLS

Turnkey Restaurant Opportunity - Prime Old Town Key West Location! Excellent opportunity to take over a fully equipped restaurant in the heart of Old Town Key West! Ideally located on the corner of Eaton and Grinnell Streets, this restaurant offers excellent visibility, indoor dining space, and inviting outdoor seating. The $35,000 asking price includes all seller owned restaurant FF&E. The seller is looking for a new operator to take over the lease and acquire the existing restaurant set up. An excellent opportunity for an experienced restaurateur or entrepreneur to establish a presence in Key West without the significant upfront investment required to build out a restaurant from scratch. Continue the existing concept or introduce your own vision in this established restaurant location. Business assets and good will only; real estate is not included. Lease assignment subject to landlord approval. Bring your vision and make this Key West restaurant location your own!

1000 Eaton St, 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

$1,350,000

Discover a rare resort-style waterfront lifestyle in Key West--an offering seldom found elsewhere on the island. At Sunset Marina, tranquil marina views, spectacular sunset views, tropical surroundings and exceptional deep water boating access come together just minutes from Key West's dining, entertainment and nearby 18-hole golf course. This move-in-ready, two-bedroom, two-bath condominium features an open-concept layout with volume ceilings, updated flooring, a water filtration system and an updated chef's kitchen with premium appliances. Overlooking the picturesque marina, the private balcony takes center stage of the living area and features electric screens for comfortable outdoor living, with access from both the main living area and the spacious primary suite. Enjoy morning coffee, waterfront breezes and relaxed evenings taking in the everchanging sunsets in your own coastal sanctuary. Set within manicured tropical grounds, Sunset Marina offers a private entrance, scenic waterfront boardwalk, heated pool, hot tub and clubhouse with a kitchen. This distinctive combination of waterfront amenities, boating convenience and resort-style surroundings presents a rare opportunity to experience Key West at a more relaxed pace. Ideal for low maintenance fly in and boat out. Lock and leave! Convenient access to the elevator and stairs, assigned covered parking and enclosed storage add everyday ease, while shared areas accommodate kayaks, bicycles and scooters. The full-service marina features a modern concrete floating dock system and direct open-water access, providing an exceptional gateway to the waters of the Florida Keys. Boat slips may be purchased separately, subject to availability. Ready for immediate occupancy, this waterfront residence invites you to settle in and begin enjoying the Key West lifestyle.

2 Beds ⋅ 2 Baths ⋅ 621605 MLS

Discover a rare resort-style waterfront lifestyle in Key West--an offering seldom found elsewhere on the island. At Sunset Marina, tranquil marina views, spectacular sunset views, tropical surroundings and exceptional deep water boating access come together just minutes from Key West's dining, entertainment and nearby 18-hole golf course. This move-in-ready, two-bedroom, two-bath condominium features an open-concept layout with volume ceilings, updated flooring, a water filtration system and an updated chef's kitchen with premium appliances. Overlooking the picturesque marina, the private balcony takes center stage of the living area and features electric screens for comfortable outdoor living, with access from both the main living area and the spacious primary suite. Enjoy morning coffee, waterfront breezes and relaxed evenings taking in the everchanging sunsets in your own coastal sanctuary. Set within manicured tropical grounds, Sunset Marina offers a private entrance, scenic waterfront boardwalk, heated pool, hot tub and clubhouse with a kitchen. This distinctive combination of waterfront amenities, boating convenience and resort-style surroundings presents a rare opportunity to experience Key West at a more relaxed pace. Ideal for low maintenance fly in and boat out. Lock and leave! Convenient access to the elevator and stairs, assigned covered parking and enclosed storage add everyday ease, while shared areas accommodate kayaks, bicycles and scooters. The full-service marina features a modern concrete floating dock system and direct open-water access, providing an exceptional gateway to the waters of the Florida Keys. Boat slips may be purchased separately, subject to availability. Ready for immediate occupancy, this waterfront residence invites you to settle in and begin enjoying the Key West lifestyle.

5607 College Rd Unit C103, Key West

$580,000

VALUE now is even SWEETER! Adjusted Price! Welcome to 138 GC Dr. in the highly sought-after Key West Golf Club residential community. Surrounded by acres of open space, Rees-Jones designed 18-hole Championship Golf Course. INVITING, Ready for Immediate Occupancy, ''Fresh as a Daisy,'' Townhome. Waiting for you! Beautifully maintained home offers the perfect blend of island living, resort-style amenities. Featuring low maintenance ceramic tile downstairs, new Berber carpet upstairs, freshly painted interior/exterior, charming picket fence, abundant natural light, 4 VERANDAS! Ideal for full-time residents, those seeking a relaxing vacation retreat, or utilize your new home intermittently while enjoying 30-day vacation rentals to supplement expenses. Ideal for long-term income producing rental home, as housing demand is great for the hardworking ''locals,'' all while you await retirement. So many options. This home is a short stroll to Golf Pro Shop, Community Center Building w/Fitness Room is just down the lane, a hop-skip-and jump to the beautiful, large lagoon-shaped pool w/tropical waterfalls. There is a real ''spirit of community!'' Peaceful ambiance in end-unit location, providing that extra breathing room. Easy to navigate kitchen has white appliances and Formica countertops. Private outdoor veranda directly off the living room is perfect for entertaining/relaxing. Primary Bedroom has 2 closets and large adjacent private veranda, which overlooks scenic Spoonbill Way. Guest Bedroom has adjacent cozy veranda overlooking the mature tree-lined streetscape w/old fashioned street lanterns. KWGC has gated entry, 24-hr. Resident Serv, 2 fabulous pools, Fitness Rm., Butterfly Garden, so much more. Just minutes from Old Town KW, beaches, marinas, shopping, and vibrant dining options, this home offers the tranquility of a private community, easy access to the excitement KW has to offer. Enjoy picturesque views, gentle tropical breezes w/the unique charm of island living.

2 Beds ⋅ 2 Baths ⋅ 621596 MLS

VALUE now is even SWEETER! Adjusted Price! Welcome to 138 GC Dr. in the highly sought-after Key West Golf Club residential community. Surrounded by acres of open space, Rees-Jones designed 18-hole Championship Golf Course. INVITING, Ready for Immediate Occupancy, ''Fresh as a Daisy,'' Townhome. Waiting for you! Beautifully maintained home offers the perfect blend of island living, resort-style amenities. Featuring low maintenance ceramic tile downstairs, new Berber carpet upstairs, freshly painted interior/exterior, charming picket fence, abundant natural light, 4 VERANDAS! Ideal for full-time residents, those seeking a relaxing vacation retreat, or utilize your new home intermittently while enjoying 30-day vacation rentals to supplement expenses. Ideal for long-term income producing rental home, as housing demand is great for the hardworking ''locals,'' all while you await retirement. So many options. This home is a short stroll to Golf Pro Shop, Community Center Building w/Fitness Room is just down the lane, a hop-skip-and jump to the beautiful, large lagoon-shaped pool w/tropical waterfalls. There is a real ''spirit of community!'' Peaceful ambiance in end-unit location, providing that extra breathing room. Easy to navigate kitchen has white appliances and Formica countertops. Private outdoor veranda directly off the living room is perfect for entertaining/relaxing. Primary Bedroom has 2 closets and large adjacent private veranda, which overlooks scenic Spoonbill Way. Guest Bedroom has adjacent cozy veranda overlooking the mature tree-lined streetscape w/old fashioned street lanterns. KWGC has gated entry, 24-hr. Resident Serv, 2 fabulous pools, Fitness Rm., Butterfly Garden, so much more. Just minutes from Old Town KW, beaches, marinas, shopping, and vibrant dining options, this home offers the tranquility of a private community, easy access to the excitement KW has to offer. Enjoy picturesque views, gentle tropical breezes w/the unique charm of island living.

138 Golf Club Dr, Key West

$515,000

Close to Duval Street but away from the hubbub, this immaculately presented one bedroom condo is just a few blocks from Smathers Beach and vibrant White Street with its restaurants, cafes, gourmet food store, galleries and fitness studios and just a walkable, rideable, half mile from the Atlantic and a mile from the Historic Seaport District and Gulf.......The condo is part of a very well run and maintained six-unit association in a highly desirable location that is peaceful and quiet. Adorable ''Sandbar Cottage'' is one of four condos located in the beautiful old 1928 yellow house part of the compound on the corner of Seminary St and Leon St.......The large windows, glass impact front door and high ceilings make this condo feel bright and spacious, giving it an abundance of natural light. The historical charm of the kitchen, main living area and bedroom are balanced by a beautifully remodeled bathroom featuring built-in cabinetry with Louisville tile in the walk-in shower and floor. All four rooms have ceiling fans.......Enjoy solitude inside or join the vibrant island life on your own 9'x 12' newly added deck built around a mature frangipani tree. The six units also share a garden area with a variety of native specimens.......The monthly condo dues cover the flood, windstorm and general liability insurances as well as yard maintenance, exterior painting and repairs.

1 Beds ⋅ 1 Baths ⋅ 621586 MLS

Close to Duval Street but away from the hubbub, this immaculately presented one bedroom condo is just a few blocks from Smathers Beach and vibrant White Street with its restaurants, cafes, gourmet food store, galleries and fitness studios and just a walkable, rideable, half mile from the Atlantic and a mile from the Historic Seaport District and Gulf.......The condo is part of a very well run and maintained six-unit association in a highly desirable location that is peaceful and quiet. Adorable ''Sandbar Cottage'' is one of four condos located in the beautiful old 1928 yellow house part of the compound on the corner of Seminary St and Leon St.......The large windows, glass impact front door and high ceilings make this condo feel bright and spacious, giving it an abundance of natural light. The historical charm of the kitchen, main living area and bedroom are balanced by a beautifully remodeled bathroom featuring built-in cabinetry with Louisville tile in the walk-in shower and floor. All four rooms have ceiling fans.......Enjoy solitude inside or join the vibrant island life on your own 9'x 12' newly added deck built around a mature frangipani tree. The six units also share a garden area with a variety of native specimens.......The monthly condo dues cover the flood, windstorm and general liability insurances as well as yard maintenance, exterior painting and repairs.

1500 Seminary St Unit APT 2D, Key West

$539,900

Great opportunity to own your own home or have an excellent source of rental income. Currently the least expensive detached residence in Key West. Freshly painted interior and new AC. This renovated one bedroom condo cottage overlooking the large communal pool is just one block to vibrant White St with its cafes and restaurants, gourmet food stores, galleries and yoga studios. A short walk or bike ride to the beaches and the heart of Old Town, the Historic Seaport and Duval Street.....The compound has a large pool shared with only 3 other condos. There are lovely landscaped communal areas with fruit trees, sun decks, lounge chairs and outdoor dining areas.....Recent improvements to the home include a metal roof, impact windows plus additional storm shutters. The condo has one bedroom, a full bath with shower above, full kitchen and double doors leading to the pool and patio area.

1 Beds ⋅ 1 Baths ⋅ 621579 MLS

Great opportunity to own your own home or have an excellent source of rental income. Currently the least expensive detached residence in Key West. Freshly painted interior and new AC. This renovated one bedroom condo cottage overlooking the large communal pool is just one block to vibrant White St with its cafes and restaurants, gourmet food stores, galleries and yoga studios. A short walk or bike ride to the beaches and the heart of Old Town, the Historic Seaport and Duval Street.....The compound has a large pool shared with only 3 other condos. There are lovely landscaped communal areas with fruit trees, sun decks, lounge chairs and outdoor dining areas.....Recent improvements to the home include a metal roof, impact windows plus additional storm shutters. The condo has one bedroom, a full bath with shower above, full kitchen and double doors leading to the pool and patio area.

1318 Duncan St Unit APT 3, 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

$3,750,000

Exceptional Key West Investment Opportunity with 3 Transient Licenses. The property consists of four private one bedrooms, one bath units, each featuring its own kitchen, living area, bedroom, and full bathroom. Most importantly, three of the four units benefit from transient rental licenses allowing nightly rentals, an increasingly rare and valuable asset in the Key West market. The fourth unit is currently rented monthly. Guests enjoy a shared private courtyard with a swimming pool, creating an inviting tropical setting and a desirable amenity for vacation renters. The property also offers three parking spaces, an added convenience in Key West. Renovated in 2018, the units blend classic Key West character with modern updates. Features include Dade County pine, engineered wood flooring, granite countertops, updated kitchen cabinetry and appliances, along with updated plumbing and electrical systems. Each unit is designed to operate independently, making the property well suited for continued use as an income producing investment.

4 Beds ⋅ 4 Baths ⋅ 621522 MLS

Exceptional Key West Investment Opportunity with 3 Transient Licenses. The property consists of four private one bedrooms, one bath units, each featuring its own kitchen, living area, bedroom, and full bathroom. Most importantly, three of the four units benefit from transient rental licenses allowing nightly rentals, an increasingly rare and valuable asset in the Key West market. The fourth unit is currently rented monthly. Guests enjoy a shared private courtyard with a swimming pool, creating an inviting tropical setting and a desirable amenity for vacation renters. The property also offers three parking spaces, an added convenience in Key West. Renovated in 2018, the units blend classic Key West character with modern updates. Features include Dade County pine, engineered wood flooring, granite countertops, updated kitchen cabinetry and appliances, along with updated plumbing and electrical systems. Each unit is designed to operate independently, making the property well suited for continued use as an income producing investment.

1501 Truman 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

$699,000

Updated CBS Duplex on Oversized Stock Island Lot - Ready Now Opportunity is knocking on Stock Island! This well-maintained CBS duplex offers 4 bedrooms and 2 bathrooms on a generously sized lot, with abundant room to park and store vehicles, boats, trailers, and work equipment, a rare find this close to Key West. Both kitchens and both bathrooms have been tastefully updated, so you can move in or rent out without lifting a finger. Solid concrete block construction provides durability and peace of mind in the Keys climate. The yard is a true blank canvas, ready for your vision, whether that's a garden retreat, outdoor entertaining space, or added storage. Live in one side and rent the other, or add a strong income property to your portfolio. Available for immediate occupancy. Just minutes from Key West dining, marinas, and amenities.

4 Beds ⋅ 2 Baths ⋅ 621519 MLS

Updated CBS Duplex on Oversized Stock Island Lot - Ready Now Opportunity is knocking on Stock Island! This well-maintained CBS duplex offers 4 bedrooms and 2 bathrooms on a generously sized lot, with abundant room to park and store vehicles, boats, trailers, and work equipment, a rare find this close to Key West. Both kitchens and both bathrooms have been tastefully updated, so you can move in or rent out without lifting a finger. Solid concrete block construction provides durability and peace of mind in the Keys climate. The yard is a true blank canvas, ready for your vision, whether that's a garden retreat, outdoor entertaining space, or added storage. Live in one side and rent the other, or add a strong income property to your portfolio. Available for immediate occupancy. Just minutes from Key West dining, marinas, and amenities.

6415 2nd Ter, 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

$1,133,000

Your Old Town Key West dream can start now -- with income built in. This exceptional 2-bedroom, 2.5-bath, townhouse-style condo offers a rare combination of Old Town lifestyle, flexible living space, and income-producing potential. Currently configured with a lock-off 1-bedroom apartment, the property offers an ideal opportunity for the future Key West homeowner: enjoy the larger 1 Bedroom, 1.5 Bath unit with private garden/patio as your own Key West retreat while the lock-off apartment provides substantial annual rental income. When the time comes to make Key West your full-time home, the property can be easily converted back to its original spacious 2-bedroom townhouse-style layout. A private gated entry opens to your own generous outdoor oasis, complete with a waterfall pond, large patio, and charming ''she-shed'' -- perfect for storage, an art studio, or entertaining. Inside, you'll find high ceilings, abundant natural light, generous storage, in-unit washer/dryers, and newer stainless-steel appliances. Just two blocks from Duval Street in the heart of Old Town's vibrant Bahama Village, you're surrounded by restaurants, galleries, shops, nightlife, and countless Key West attractions -- all within easy walking distance. Whether you're ready for a Key West home now or envision making the island your full-time home in the future, this is a rare opportunity to own your piece of Old Town, enjoy income along the way, and ultimately create the spacious Key West home you've been dreaming of. Some seller financing considered. Seller is a Florida Licensed Realtor. Photos 10-17 show Original Layout, 18=FloorPlan, 19-37 show Back Unit, 38-49 show Front Lock-Off Apt.

2 Beds ⋅ 3 Baths ⋅ 621479 MLS

Your Old Town Key West dream can start now -- with income built in. This exceptional 2-bedroom, 2.5-bath, townhouse-style condo offers a rare combination of Old Town lifestyle, flexible living space, and income-producing potential. Currently configured with a lock-off 1-bedroom apartment, the property offers an ideal opportunity for the future Key West homeowner: enjoy the larger 1 Bedroom, 1.5 Bath unit with private garden/patio as your own Key West retreat while the lock-off apartment provides substantial annual rental income. When the time comes to make Key West your full-time home, the property can be easily converted back to its original spacious 2-bedroom townhouse-style layout. A private gated entry opens to your own generous outdoor oasis, complete with a waterfall pond, large patio, and charming ''she-shed'' -- perfect for storage, an art studio, or entertaining. Inside, you'll find high ceilings, abundant natural light, generous storage, in-unit washer/dryers, and newer stainless-steel appliances. Just two blocks from Duval Street in the heart of Old Town's vibrant Bahama Village, you're surrounded by restaurants, galleries, shops, nightlife, and countless Key West attractions -- all within easy walking distance. Whether you're ready for a Key West home now or envision making the island your full-time home in the future, this is a rare opportunity to own your piece of Old Town, enjoy income along the way, and ultimately create the spacious Key West home you've been dreaming of. Some seller financing considered. Seller is a Florida Licensed Realtor. Photos 10-17 show Original Layout, 18=FloorPlan, 19-37 show Back Unit, 38-49 show Front Lock-Off Apt.

927 Thomas St Unit 1, 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 ⋅ 621477 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

How much is your home worth?

How much is your home worth?