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Excellent opportunity whether looking for a private residence or an investment. This home will not disappoint. Artfully renovated very spacious three story . Plenty of outside area including private courtyard with a heated pool. Walk out the front door and just steps away from Duval st. and everything Key West has to offer. This is maintenance free living while it gives the feeling of a private residence. Assigned off street parking right in front of the unit. This property is being offered turnkey. Vacation Rental history available .This home has all hurricane impact windows and doors. making the unit noiseless. This condo is a freestanding building just like a single family home without the maintenance.

3 Beds ⋅ 3 Baths ⋅ 610882 MLS

Excellent opportunity whether looking for a private residence or an investment. This home will not disappoint. Artfully renovated very spacious three story . Plenty of outside area including private courtyard with a heated pool. Walk out the front door and just steps away from Duval st. and everything Key West has to offer. This is maintenance free living while it gives the feeling of a private residence. Assigned off street parking right in front of the unit. This property is being offered turnkey. Vacation Rental history available .This home has all hurricane impact windows and doors. making the unit noiseless. This condo is a freestanding building just like a single family home without the maintenance.

1011 Simonton St Unit R1, Key West

$1,475,000

Timeless Old Town Charm! Discover the timeless appeal of this beautifully remodeled historic home located in the heart of Old Town, Key West. Offered fully furnished, this stunning 3-bedroom, 2.5-bath residence showcases lovingly restored Dade County Pine and blends classic craftsmanship with today's most desirable upgrades. 1211 Knowles Lane features a versatile 300 sq. ft. loft currently utilized as a third bedroom, office, and additional storage, perfect for flexible island living. Inviting front and side porches set the tone for relaxed Key West living, offering peaceful spaces to unwind and enjoy the tranquil neighborhood. Inside, you're welcomed by bright, spacious living areas highlighted by soaring ceilings and gorgeous flooring throughout the living and dining rooms. The thoughtfully updated kitchen boasts stainless steel appliances, custom cabinetry, and a generous pantry designed for both everyday living and entertaining.The bedrooms are comfortably sized, offering charm and privacy. Bathrooms have been tastefully renovated with contemporary fixtures while preserving the home's historic character. Step outside onto beautiful teak decking into your own private tropical oasis. The backyard retreat features an outdoor shower, hot tub, rooftop deck, and brick-paved driveways creating the ultimate indoor-outdoor island lifestyle. Located in a prime Old Town setting, you're just a leisurely walk or bike ride to Key West's beautiful beaches, renowned restaurants, and vibrant nightlife. *Bonus features: off street parking and located in the x-flood zone.

3 Beds ⋅ 3 Baths ⋅ 618863 MLS

Timeless Old Town Charm! Discover the timeless appeal of this beautifully remodeled historic home located in the heart of Old Town, Key West. Offered fully furnished, this stunning 3-bedroom, 2.5-bath residence showcases lovingly restored Dade County Pine and blends classic craftsmanship with today's most desirable upgrades. 1211 Knowles Lane features a versatile 300 sq. ft. loft currently utilized as a third bedroom, office, and additional storage, perfect for flexible island living. Inviting front and side porches set the tone for relaxed Key West living, offering peaceful spaces to unwind and enjoy the tranquil neighborhood. Inside, you're welcomed by bright, spacious living areas highlighted by soaring ceilings and gorgeous flooring throughout the living and dining rooms. The thoughtfully updated kitchen boasts stainless steel appliances, custom cabinetry, and a generous pantry designed for both everyday living and entertaining.The bedrooms are comfortably sized, offering charm and privacy. Bathrooms have been tastefully renovated with contemporary fixtures while preserving the home's historic character. Step outside onto beautiful teak decking into your own private tropical oasis. The backyard retreat features an outdoor shower, hot tub, rooftop deck, and brick-paved driveways creating the ultimate indoor-outdoor island lifestyle. Located in a prime Old Town setting, you're just a leisurely walk or bike ride to Key West's beautiful beaches, renowned restaurants, and vibrant nightlife. *Bonus features: off street parking and located in the x-flood zone.

1211 Knowles Ln, Key West

3841 N Roosevelt Blvd Unit 332, Key West

$1,949,000

Experience ultimate elegance at Key West's Beachside Resort & Residences! This third-floor Condominium offers the perfect blend of luxury, flexibility, and investment potential. Featuring two transient licenses and a lockout configuration, this property includes both a Signature King Room and a Resort View Suite, which can be used together or separately for optimal rental income. The Signature King Room (283 sq. ft.) is an intimate, elegantly furnished retreat ideal for up to two guests. The Resort View Suite (1,074 sq. ft.) features an open floor plan with a designer kitchen equipped with Sub-Zero, KitchenAid, GE, and Bosch appliances, dual stainless-steel sinks, and custom cabinetry. The primary suite offers a spa-inspired bath with a sunken jetted tub, tiled shower, and dual vanities. Positioned on open Gulf waters, the Suites private rooftop sundeck provides a front-row seat to Key West's spectacular sunsets. Throughout both units, you'll find 16-inch marble tile flooring, crown molding, and high-end finishes that elevate every detail. Fully furnished and beautifully decorated, this residence is designed for year-round living or part-time ownership—with the convenience of optional on-site rental management when you're away. All doors and windows are engineered to exceed building codes, rated for up to 175 mph winds, ensuring both safety and peace of mind. Resort-style amenities include a private beach, heated waterfront pool and spa, poolside bar & grill, gourmet restaurant, fitness center, valet parking, concierge services, on-site management, and the island's largest conference center. This property presents an extraordinary opportunity to enjoy the best of Key West luxury living—a perfect combination of personal enjoyment and investment performance.

2 Beds ⋅ 3 Baths ⋅ 616791 MLS

Experience ultimate elegance at Key West's Beachside Resort & Residences! This third-floor Condominium offers the perfect blend of luxury, flexibility, and investment potential. Featuring two transient licenses and a lockout configuration, this property includes both a Signature King Room and a Resort View Suite, which can be used together or separately for optimal rental income. The Signature King Room (283 sq. ft.) is an intimate, elegantly furnished retreat ideal for up to two guests. The Resort View Suite (1,074 sq. ft.) features an open floor plan with a designer kitchen equipped with Sub-Zero, KitchenAid, GE, and Bosch appliances, dual stainless-steel sinks, and custom cabinetry. The primary suite offers a spa-inspired bath with a sunken jetted tub, tiled shower, and dual vanities. Positioned on open Gulf waters, the Suites private rooftop sundeck provides a front-row seat to Key West's spectacular sunsets. Throughout both units, you'll find 16-inch marble tile flooring, crown molding, and high-end finishes that elevate every detail. Fully furnished and beautifully decorated, this residence is designed for year-round living or part-time ownership—with the convenience of optional on-site rental management when you're away. All doors and windows are engineered to exceed building codes, rated for up to 175 mph winds, ensuring both safety and peace of mind. Resort-style amenities include a private beach, heated waterfront pool and spa, poolside bar & grill, gourmet restaurant, fitness center, valet parking, concierge services, on-site management, and the island's largest conference center. This property presents an extraordinary opportunity to enjoy the best of Key West luxury living—a perfect combination of personal enjoyment and investment performance.

3841 N Roosevelt Blvd Unit 332, Key West

1445 S 1445 Roosevelt Blvd Unit 411, Key West

$1,070,000

Two fully furnished condos are available at Coconut Mallory Marina & Resort, each with a rare transient rental license allowing rentals of one day or longer. Units #411 and #412 are listed separately and may be purchased individually or together, offering buyers the flexibility to acquire one turnkey vacation rental or both as an investment package. Known together as The Poolside Cottages, these charming 1BR/1BA units are conveniently located near the pool and feature private patios, vaulted ceilings, updated interiors, and sleeping accommodations for up to six guests per condo. Each unit is fully furnished, turnkey, and ready for immediate rental income, with dedicated laundry access and assigned parking included. Coconut Mallory Marina & Resort offers two swimming pools, a jacuzzi, lush tropical grounds, a private marina with boat access, and the relaxed Key West atmosphere guests love. The resort is conveniently located near Smathers Beach, Duval Street, Old Town, Key West International Airport, and many of the island's most popular attractions. HOA dues include electric, water, sewer, garbage, Wi-Fi, cable, exterior insurance, and common area maintenance. A rare opportunity to purchase one or two transient-licensed vacation rentals in one of Key West's hidden gems. Purchase either condo individually, or acquire both Poolside Cottages for a distinctive dual-unit investment opportunity.

1 Beds ⋅ 1 Baths ⋅ 615746 MLS

Two fully furnished condos are available at Coconut Mallory Marina & Resort, each with a rare transient rental license allowing rentals of one day or longer. Units #411 and #412 are listed separately and may be purchased individually or together, offering buyers the flexibility to acquire one turnkey vacation rental or both as an investment package. Known together as The Poolside Cottages, these charming 1BR/1BA units are conveniently located near the pool and feature private patios, vaulted ceilings, updated interiors, and sleeping accommodations for up to six guests per condo. Each unit is fully furnished, turnkey, and ready for immediate rental income, with dedicated laundry access and assigned parking included. Coconut Mallory Marina & Resort offers two swimming pools, a jacuzzi, lush tropical grounds, a private marina with boat access, and the relaxed Key West atmosphere guests love. The resort is conveniently located near Smathers Beach, Duval Street, Old Town, Key West International Airport, and many of the island's most popular attractions. HOA dues include electric, water, sewer, garbage, Wi-Fi, cable, exterior insurance, and common area maintenance. A rare opportunity to purchase one or two transient-licensed vacation rentals in one of Key West's hidden gems. Purchase either condo individually, or acquire both Poolside Cottages for a distinctive dual-unit investment opportunity.

1445 S 1445 Roosevelt Blvd Unit 411, Key West

$799,000

Seller financing available. New impact rated windows, doors, and sliders. Ready for immediate occupancy! This Spa home located in the Sanctuary at the Key West Golf Club features a private dip pool and carport. The first floor is an open floor plan with kitchen, living area and half bath. French doors open to the walled, private rear yard with your own dip pool. Upstairs feature the primary and guest bedroom ensuites. The Key West Golf Club also features a fitness center and large community pool. Listing Broker/Owner is Florida REALTOR and therefore has ownership interest in the property. Very easy to show!

2 Beds ⋅ 3 Baths ⋅ 618354 MLS

Seller financing available. New impact rated windows, doors, and sliders. Ready for immediate occupancy! This Spa home located in the Sanctuary at the Key West Golf Club features a private dip pool and carport. The first floor is an open floor plan with kitchen, living area and half bath. French doors open to the walled, private rear yard with your own dip pool. Upstairs feature the primary and guest bedroom ensuites. The Key West Golf Club also features a fitness center and large community pool. Listing Broker/Owner is Florida REALTOR and therefore has ownership interest in the property. Very easy to show!

202 Golf Club Dr, Key West

2601 S Roosevelt Blvd Unit 204A, Key West

$599,000

Wake up to breathtaking direct ocean views from this second-floor, 1-bedroom, 1-bath residence located in the desirable 'A' building at Key West by the Sea. This bright and airy condo designed to capture natural light and showcase the stunning beach and ocean scenery. The unit was upgraded through the 2018 Airport Noise Improvement Project and includes hurricane-impact, sound-insulated windows and doors, providing exceptional tranquility throughout the home. Energy-efficient ductless mini-split A/C systems in both the living area and bedroom offer customized comfort year-round. Situated directly across the street from iconic Smathers Beach, this location is ideal for beach lovers and outdoor enthusiasts alike. Enjoy swimming, sunbathing, and watersports, or take advantage of the wide, paved beachfront promenadeâ€'perfect for biking, jogging, skating, or leisurely sunset strolls. The gated Key West by the Sea community offers resort-style amenities including two swimming pools, two tennis courts, a clubhouse, four conveniently located laundry rooms, bike racks, a car-wash station, and a pet walking area. The community is pet-friendly and well maintained, with condo fees covering building insurance, cable TV, security, pest control, and full grounds and building maintenance. After the first year of ownership, the unit may be rented with a minimum two-month term, adding flexibility and investment potential. Whether you're searching for a serene island retreat, a full-time residence, or a smart coastal investment, this oceanview condo delivers the best of Key West livingâ€'location, views, and lifestyleâ€'all in one exceptional package.

1 Beds ⋅ 1 Baths ⋅ 618286 MLS

Wake up to breathtaking direct ocean views from this second-floor, 1-bedroom, 1-bath residence located in the desirable 'A' building at Key West by the Sea. This bright and airy condo designed to capture natural light and showcase the stunning beach and ocean scenery. The unit was upgraded through the 2018 Airport Noise Improvement Project and includes hurricane-impact, sound-insulated windows and doors, providing exceptional tranquility throughout the home. Energy-efficient ductless mini-split A/C systems in both the living area and bedroom offer customized comfort year-round. Situated directly across the street from iconic Smathers Beach, this location is ideal for beach lovers and outdoor enthusiasts alike. Enjoy swimming, sunbathing, and watersports, or take advantage of the wide, paved beachfront promenadeâ€'perfect for biking, jogging, skating, or leisurely sunset strolls. The gated Key West by the Sea community offers resort-style amenities including two swimming pools, two tennis courts, a clubhouse, four conveniently located laundry rooms, bike racks, a car-wash station, and a pet walking area. The community is pet-friendly and well maintained, with condo fees covering building insurance, cable TV, security, pest control, and full grounds and building maintenance. After the first year of ownership, the unit may be rented with a minimum two-month term, adding flexibility and investment potential. Whether you're searching for a serene island retreat, a full-time residence, or a smart coastal investment, this oceanview condo delivers the best of Key West livingâ€'location, views, and lifestyleâ€'all in one exceptional package.

2601 S Roosevelt Blvd Unit 204A, Key West

$5,500,000

Experience the grandeur of this exceptional six bedroom, five and a half bath estate located on one of the most exclusive streets in Key West. A stunning wall of bougainvillea and the stately front porch welcome you to this 3,751 square foot property on an expansive 10,750 square foot lot that embodies historic Key West architecture. The main residence features four bedrooms, three and half baths of elegant living spaces, including a first-floor mother-in-law suite. Timeless design is found throughout with abundance of natural light and views of the lush, exotic landscape out every window. The great room features 12' ceilings, a curved wall of windows and French doors that lead to the serene, covered porch and outdoor dining space. The kitchen is a chef's dream equipped with new Viking appliances, ample counter space, and a view that overlooks the gorgeous, azure pool. The second level includes a spacious primary suite and two additional guest rooms, one of which has a balcony with treetop views and the island's best spot to view the spectacular 4th of July firework show. Two charming detached guest cottages tucked amongst the gardens offer secluded retreats each with full baths and one offering a living room and kitchenette. The outdoor oasis is defined by the oversized L-shaped pool and outdoor kitchen with built-in Viking grill; the perfect space for entertaining. This property is an exceptional, private sanctuary at an unbeatable location just one block from the crystal-clear Atlantic, tennis and pickleball courts, the esteemed Casa Marina Hotel and iconic White Street Pier. Don't miss the opportunity to call this remarkable estate your home! Seller is a licensed real estate broker and related to the listing agent. Seller is a licensed real estate broker and related to the listing agent.

6 Beds ⋅ 6 Baths ⋅ 618573 MLS

Experience the grandeur of this exceptional six bedroom, five and a half bath estate located on one of the most exclusive streets in Key West. A stunning wall of bougainvillea and the stately front porch welcome you to this 3,751 square foot property on an expansive 10,750 square foot lot that embodies historic Key West architecture. The main residence features four bedrooms, three and half baths of elegant living spaces, including a first-floor mother-in-law suite. Timeless design is found throughout with abundance of natural light and views of the lush, exotic landscape out every window. The great room features 12' ceilings, a curved wall of windows and French doors that lead to the serene, covered porch and outdoor dining space. The kitchen is a chef's dream equipped with new Viking appliances, ample counter space, and a view that overlooks the gorgeous, azure pool. The second level includes a spacious primary suite and two additional guest rooms, one of which has a balcony with treetop views and the island's best spot to view the spectacular 4th of July firework show. Two charming detached guest cottages tucked amongst the gardens offer secluded retreats each with full baths and one offering a living room and kitchenette. The outdoor oasis is defined by the oversized L-shaped pool and outdoor kitchen with built-in Viking grill; the perfect space for entertaining. This property is an exceptional, private sanctuary at an unbeatable location just one block from the crystal-clear Atlantic, tennis and pickleball courts, the esteemed Casa Marina Hotel and iconic White Street Pier. Don't miss the opportunity to call this remarkable estate your home! Seller is a licensed real estate broker and related to the listing agent. Seller is a licensed real estate broker and related to the listing agent.

906 Johnson St, Key West

$1,474,000

POOL & POOL HOUSE COMPLETED! Opportunity awaits to create your perfect midtown home. This property consists of a partially updated main home totaling 1233 sq ft with 2bd/2ba and a bonus room. A newly constructed elevated 256 sq ft guesthouse with a kitchenette and bathroom. Professional landscaping, pavers and low maintenance artificial grass lead to the brand new heated pool. Irrigation and landscape lighting installed. Main house needs some renovations throughout but has been partially updated and is perfectly livable. Must see!!

3 Beds ⋅ 3 Baths ⋅ 617589 MLS

POOL & POOL HOUSE COMPLETED! Opportunity awaits to create your perfect midtown home. This property consists of a partially updated main home totaling 1233 sq ft with 2bd/2ba and a bonus room. A newly constructed elevated 256 sq ft guesthouse with a kitchenette and bathroom. Professional landscaping, pavers and low maintenance artificial grass lead to the brand new heated pool. Irrigation and landscape lighting installed. Main house needs some renovations throughout but has been partially updated and is perfectly livable. Must see!!

1505 Johnson St, Key West

$1,060,000

At the end of wide, quiet cul-de-sac, life naturally slows, sunsets linger, 20 Kingfisher reveals itself as a private island retreat @ KW Golf Club. Inviting brick walkway, lush tropical landscaping, river rock, lead to freshly painted front steps, welcoming front veranda that set the tone, refined, thoughtfully cared for. This home feels loved the moment you arrive. Inside, warmth & craftsmanship take center stage. Rich heart pine flooring grounds the main level, continuing up the staircase. Elegant, functional fully remodeled kitchen features custom cottage-style wooden cabinetry, soft-close drawers, luxurious granite countertops, beautiful built-in storage beneath the breakfast bar. All upgraded stainless appliances complete the space: new dishwasher, radiant cooktop range w/double ovens/convection, microwave, French-door refrigerator/freezer, every detail chosen for beauty & performance. From the living area, the home opens to a captivating, expanded screened rear veranda overlooking the lake, the #2 tee box & S.W. sky that delivers breathtaking sunsets. When the Royal Poinciana bursts into bloom, its fiery canopy becomes a work of art, reflected in the water, glowing at dusk, unforgettable! Upstairs, the home transforms into a tranquil private retreat. High-end luxury vinyl plank flooring w/padded underlayment provides a cushioned ''walking on air'' feel, waterproof, elegant, designed for long-term comfort. 2 spacious en-suite bedrooms anchor the 2nd level, defined by cozy architectural charm w/gentle eaved rooflines, adding character & intimate cottage feel. The primary suite is inviting w/a generous double closet & large built-in storage. En-suite bath is a true showpiece, featuring new pendant lighting, fully tiled walk-in shower w/built-in bench, wrapped in vibrant royal blue/burgundy ceramic tile. Guest bdrm. is mirrored image w/lg. extended closet. 3rd bdrm. is office/study. Private heated resurfaced pool upgraded w/steps/railing is divine. So much more!

3 Beds ⋅ 3 Baths ⋅ 618186 MLS

At the end of wide, quiet cul-de-sac, life naturally slows, sunsets linger, 20 Kingfisher reveals itself as a private island retreat @ KW Golf Club. Inviting brick walkway, lush tropical landscaping, river rock, lead to freshly painted front steps, welcoming front veranda that set the tone, refined, thoughtfully cared for. This home feels loved the moment you arrive. Inside, warmth & craftsmanship take center stage. Rich heart pine flooring grounds the main level, continuing up the staircase. Elegant, functional fully remodeled kitchen features custom cottage-style wooden cabinetry, soft-close drawers, luxurious granite countertops, beautiful built-in storage beneath the breakfast bar. All upgraded stainless appliances complete the space: new dishwasher, radiant cooktop range w/double ovens/convection, microwave, French-door refrigerator/freezer, every detail chosen for beauty & performance. From the living area, the home opens to a captivating, expanded screened rear veranda overlooking the lake, the #2 tee box & S.W. sky that delivers breathtaking sunsets. When the Royal Poinciana bursts into bloom, its fiery canopy becomes a work of art, reflected in the water, glowing at dusk, unforgettable! Upstairs, the home transforms into a tranquil private retreat. High-end luxury vinyl plank flooring w/padded underlayment provides a cushioned ''walking on air'' feel, waterproof, elegant, designed for long-term comfort. 2 spacious en-suite bedrooms anchor the 2nd level, defined by cozy architectural charm w/gentle eaved rooflines, adding character & intimate cottage feel. The primary suite is inviting w/a generous double closet & large built-in storage. En-suite bath is a true showpiece, featuring new pendant lighting, fully tiled walk-in shower w/built-in bench, wrapped in vibrant royal blue/burgundy ceramic tile. Guest bdrm. is mirrored image w/lg. extended closet. 3rd bdrm. is office/study. Private heated resurfaced pool upgraded w/steps/railing is divine. So much more!

20 Kingfisher Ln, Key West

1445 S Roosevelt Blvd Unit 412, Key West

$1,070,000

Two fully furnished condos are available at Coconut Mallory Marina & Resort, each with a rare transient rental license allowing rentals of one day or longer. Units #411 and #412 are listed separately and may be purchased individually or together, offering buyers the flexibility to acquire one turnkey vacation rental or both as an investment package. Known together as The Poolside Cottages, these charming 1BR/1BA units are conveniently located near the pool and feature private patios, vaulted ceilings, updated interiors, and sleeping accommodations for up to six guests per condo. Each unit is fully furnished, turnkey, and ready for immediate rental income, with dedicated laundry access and assigned parking included. Coconut Mallory Marina & Resort offers two swimming pools, a jacuzzi, lush tropical grounds, a private marina with boat access, and the relaxed Key West atmosphere guests love. The resort is conveniently located near Smathers Beach, Duval Street, Old Town, Key West International Airport, and many of the island's most popular attractions. HOA dues include electric, water, sewer, garbage, Wi-Fi, cable, exterior insurance, and common area maintenance. A rare opportunity to purchase one or two transient-licensed vacation rentals in one of Key West's hidden gems. Purchase either condo individually, or acquire both Poolside Cottages for a distinctive dual-unit investment opportunity.

1 Beds ⋅ 1 Baths ⋅ 615748 MLS

Two fully furnished condos are available at Coconut Mallory Marina & Resort, each with a rare transient rental license allowing rentals of one day or longer. Units #411 and #412 are listed separately and may be purchased individually or together, offering buyers the flexibility to acquire one turnkey vacation rental or both as an investment package. Known together as The Poolside Cottages, these charming 1BR/1BA units are conveniently located near the pool and feature private patios, vaulted ceilings, updated interiors, and sleeping accommodations for up to six guests per condo. Each unit is fully furnished, turnkey, and ready for immediate rental income, with dedicated laundry access and assigned parking included. Coconut Mallory Marina & Resort offers two swimming pools, a jacuzzi, lush tropical grounds, a private marina with boat access, and the relaxed Key West atmosphere guests love. The resort is conveniently located near Smathers Beach, Duval Street, Old Town, Key West International Airport, and many of the island's most popular attractions. HOA dues include electric, water, sewer, garbage, Wi-Fi, cable, exterior insurance, and common area maintenance. A rare opportunity to purchase one or two transient-licensed vacation rentals in one of Key West's hidden gems. Purchase either condo individually, or acquire both Poolside Cottages for a distinctive dual-unit investment opportunity.

1445 S Roosevelt Blvd Unit 412, Key West

$2,199,000

This versatile 3-family property offers a rare blend of privacy & income potential. Designed as 3 distinct residences, each with a private entrance and it's own kitchen and w/d, the property is ideal for an owner-occupant seeking rental income or an investment for long term, vacation rentals or family compound. Main Level - Primary Residence: The spacious downstairs layout features a 2 bed, 2 bath, open-concept living area & updated kitchen w/ quartz countertops, wine cooler, & pantry overlooking the pool. The master suite has a built-in office, a custom walk-in closet system, & updated bath w/walk in shower. Main Level - Guest Suite is freshly painted w/private entrance, full kitchen, dedicated laundry, & full bathroom. Upper Level -3 beds & 2 baths, w/d, private entrance, French doors & balconies overlook the backyard foliage & pool. The 2nd remodeled bathroom services the 2 bedrooms, 1 of which is used as a media room. The open Living room/Kitchen has built-in wall shelves, The secluded backyard features a heated/chilled saltwater pool w/custom water feature by renowned master potter Jay Gogin. The grounds are secured by unique bamboo fencing and include a refreshing outdoor shower. Whole-house Generac generator and a large Rheem on-demand gas tankless water heater. Front of the house features an elevated patio overlooking the street. metal roof, accordion/panel storm shutters, & 2 driveways as well as 3 off-street parking . Need 24 hour notice to show!

6 Beds ⋅ 5 Baths ⋅ 617882 MLS

This versatile 3-family property offers a rare blend of privacy & income potential. Designed as 3 distinct residences, each with a private entrance and it's own kitchen and w/d, the property is ideal for an owner-occupant seeking rental income or an investment for long term, vacation rentals or family compound. Main Level - Primary Residence: The spacious downstairs layout features a 2 bed, 2 bath, open-concept living area & updated kitchen w/ quartz countertops, wine cooler, & pantry overlooking the pool. The master suite has a built-in office, a custom walk-in closet system, & updated bath w/walk in shower. Main Level - Guest Suite is freshly painted w/private entrance, full kitchen, dedicated laundry, & full bathroom. Upper Level -3 beds & 2 baths, w/d, private entrance, French doors & balconies overlook the backyard foliage & pool. The 2nd remodeled bathroom services the 2 bedrooms, 1 of which is used as a media room. The open Living room/Kitchen has built-in wall shelves, The secluded backyard features a heated/chilled saltwater pool w/custom water feature by renowned master potter Jay Gogin. The grounds are secured by unique bamboo fencing and include a refreshing outdoor shower. Whole-house Generac generator and a large Rheem on-demand gas tankless water heater. Front of the house features an elevated patio overlooking the street. metal roof, accordion/panel storm shutters, & 2 driveways as well as 3 off-street parking . Need 24 hour notice to show!

1609 United St, Key West

$1,875,000

This rare Key West treasure hasn't changed hands in over a century, and it sits on the most coveted block in Old Town. A true time capsule waiting to be revived, it's the last of its kind not yet renovated--so you won't be buying someone else's overpriced remodel. Bring your imagination and restore this home to its original, sun-soaked beauty. There's not another lot like it in Old Town. The nearly 5,000-square-foot lot stretches from Fleming Street to Stickeny Lane, offering ample off-street parking and a golden opportunity to expand your tropical living dreams. Nestled in the heart of Old Town, 1115 is just blocks from the historic Seaport and a stone's throw from the city's famous restaurants and nightlife. Early 1900s Sanborn maps even hint at an additional house on the property that may be rebuilt with city permissions (buyers to verify). The home still contains generous pockets of its original Dade County pine, along with historic windows and double balconies that invite sea breezes and sunset cocktails. Currently a legal duplex, each side offers 2 bedrooms and 1 bath. You can keep the duplex as-is, or transform it into a stunning single-family residence in the most sought-after neighborhood in all of Key West.

4 Beds ⋅ 2 Baths ⋅ 618211 MLS

This rare Key West treasure hasn't changed hands in over a century, and it sits on the most coveted block in Old Town. A true time capsule waiting to be revived, it's the last of its kind not yet renovated--so you won't be buying someone else's overpriced remodel. Bring your imagination and restore this home to its original, sun-soaked beauty. There's not another lot like it in Old Town. The nearly 5,000-square-foot lot stretches from Fleming Street to Stickeny Lane, offering ample off-street parking and a golden opportunity to expand your tropical living dreams. Nestled in the heart of Old Town, 1115 is just blocks from the historic Seaport and a stone's throw from the city's famous restaurants and nightlife. Early 1900s Sanborn maps even hint at an additional house on the property that may be rebuilt with city permissions (buyers to verify). The home still contains generous pockets of its original Dade County pine, along with historic windows and double balconies that invite sea breezes and sunset cocktails. Currently a legal duplex, each side offers 2 bedrooms and 1 bath. You can keep the duplex as-is, or transform it into a stunning single-family residence in the most sought-after neighborhood in all of Key West.

1115 Fleming St, Key West

$935,000

One Bedroom / One bathroom PLUS super cool Sleeping Loft! THIS is it! Step into a piece of Old Town Key West history. Built in 1928, this storybook Old Town cottage captures everything to love about Key West including its timeless character and that easy island rhythm you can feel the moment you arrive. Light, bright, and beautifully furnished, it's move-in ready, the perfect turn-key retreat for anyone dreaming of a second home or an easy vacation rental in the heart of Key West. Inside, you'll find soaring wood-vaulted ceilings and warm floors features that hint to island's past. The updated Kitchen is ready for entertaining, while the additional and spaciously airy sleeping loft adds extra space and great character, while the private back deck invites unforgettable evenings dining under the stars. Out front, the iconic porch is made for slow evenings, and people-watching ... the classic Key West pastime. Just two blocks from Duval Street, this location is unbeatable, it's close enough to walk to the best restaurants, galleries, and shops, yet tucked away for peace and privacy. Even better, it's in the coveted X-Zone, so no flood insurance is required, and yes, it has its own, coveted off-street parking spot Phenomenal Vacation Rental and 1031 Exchange potential. This isn't just a home; it's a private oasis. It's YOUR Key West story waiting to be written.

1 Beds ⋅ 1 Baths ⋅ 618122 MLS

One Bedroom / One bathroom PLUS super cool Sleeping Loft! THIS is it! Step into a piece of Old Town Key West history. Built in 1928, this storybook Old Town cottage captures everything to love about Key West including its timeless character and that easy island rhythm you can feel the moment you arrive. Light, bright, and beautifully furnished, it's move-in ready, the perfect turn-key retreat for anyone dreaming of a second home or an easy vacation rental in the heart of Key West. Inside, you'll find soaring wood-vaulted ceilings and warm floors features that hint to island's past. The updated Kitchen is ready for entertaining, while the additional and spaciously airy sleeping loft adds extra space and great character, while the private back deck invites unforgettable evenings dining under the stars. Out front, the iconic porch is made for slow evenings, and people-watching ... the classic Key West pastime. Just two blocks from Duval Street, this location is unbeatable, it's close enough to walk to the best restaurants, galleries, and shops, yet tucked away for peace and privacy. Even better, it's in the coveted X-Zone, so no flood insurance is required, and yes, it has its own, coveted off-street parking spot Phenomenal Vacation Rental and 1031 Exchange potential. This isn't just a home; it's a private oasis. It's YOUR Key West story waiting to be written.

817 Terry Ln, Key West

$4,300,000

**31 photos have been virtually staged and enhanced to assist buyers in visualizing design and decor options for this home.** Casa Sapodilla introduces itself with the kind of presence that feels both storied and serene. Built in 1996 and set at 13' elevation on Solares Hill, the residence pays homage to the architectural romance of Old Town's most celebrated homes.. broad verandas, intricate trim work, and Brazilian Cherry hardwood floors that recall a bygone era of island craftsmanship. Inside, the home unfolds in layers of refinement. Sunlit rooms connect gracefully to the outdoors through French doors and deep porches. The main house's split-level design elevates the primary suite with its own private staircase, while two additional bedrooms ascend another, creating a sense of calm seclusion. A separate pool suite, complete with private entrance, extends the home's versatility. The kitchen is anchored by a suite of premier appliances.. including a new SubZero refrigerator and a refurbished Viking gas range, and framed by custom cabinetry and built-ins. Recent upgrades such as the 2025 metal roof, updated HVAC systems, and a 24 kW Generac whole-house generator reflect meticulous stewardship. Outside, the grounds rise to the level of a private resort. Tropical gardens wind around stone pathways, illuminated at night by soft landscape lighting. A heated saltwater lagoon-style pool, resurfaced in 2025, curves around natural rock formations, a spa, and three cascading waterfalls. Every vista offers a moment of stillness.. from the shaded verandas to the courtyard designed for open-air dining. A one-car air-conditioned garage, currently serving as an art studio, and a two-car driveway complete the thoughtful layout. Just blocks from Duval Street and the Key West Historic Seaport, Casa Sapodilla is both connected and deeply private.. a luxury retreat rooted in island elegance.. Inquire within for details on the low insurance costs available for this home

4 Beds ⋅ 6 Baths ⋅ 617513 MLS

**31 photos have been virtually staged and enhanced to assist buyers in visualizing design and decor options for this home.** Casa Sapodilla introduces itself with the kind of presence that feels both storied and serene. Built in 1996 and set at 13' elevation on Solares Hill, the residence pays homage to the architectural romance of Old Town's most celebrated homes.. broad verandas, intricate trim work, and Brazilian Cherry hardwood floors that recall a bygone era of island craftsmanship. Inside, the home unfolds in layers of refinement. Sunlit rooms connect gracefully to the outdoors through French doors and deep porches. The main house's split-level design elevates the primary suite with its own private staircase, while two additional bedrooms ascend another, creating a sense of calm seclusion. A separate pool suite, complete with private entrance, extends the home's versatility. The kitchen is anchored by a suite of premier appliances.. including a new SubZero refrigerator and a refurbished Viking gas range, and framed by custom cabinetry and built-ins. Recent upgrades such as the 2025 metal roof, updated HVAC systems, and a 24 kW Generac whole-house generator reflect meticulous stewardship. Outside, the grounds rise to the level of a private resort. Tropical gardens wind around stone pathways, illuminated at night by soft landscape lighting. A heated saltwater lagoon-style pool, resurfaced in 2025, curves around natural rock formations, a spa, and three cascading waterfalls. Every vista offers a moment of stillness.. from the shaded verandas to the courtyard designed for open-air dining. A one-car air-conditioned garage, currently serving as an art studio, and a two-car driveway complete the thoughtful layout. Just blocks from Duval Street and the Key West Historic Seaport, Casa Sapodilla is both connected and deeply private.. a luxury retreat rooted in island elegance.. Inquire within for details on the low insurance costs available for this home

600 Elizabeth St, Key West

$1,175,000

This show-stopping luxury condo delivers a rare blend of historic charm with a fully renovated interior that was just completed a few years ago. The first level features an open living and dining plan with 10' ceilings, an abundance of natural light, restored Dade County Pine accent walls, plantation shutters, modern lighting, and tile flooring throughout. The kitchen was built to impress and features a large quartz island, Cafe Collection appliances, a gas range, designer tile backsplash, and a separate coffee and cocktail bar. Practical touches include an entry way storage closet, built-in closet systems, and a full-size GE washer and dryer tucked neatly under the stairs. The upstairs primary suite feels like a private retreat.. it features a sitting area with double French doors that open to the balcony perch where you'll enjoy views of beautiful sunsets through the treetops. The en suite bath is finished with gorgeous Onyx Style slab tile, a double vanity, designer fixtures and a glass shower with statement detailing. This luxury condo is offered fully furnished and turnkey, with local Key West history woven throughout. 30-day rentals are allowed with restrictions, it's in the X Flood Zone, and from here it's always an easy stroll to Fort Zach Beach, Truman Waterfront Park, and the Duval Street corridor for fine dining, shopping, and live entertainment, capturing the ease and energy of Key West living..

2 Beds ⋅ 2 Baths ⋅ 618511 MLS

This show-stopping luxury condo delivers a rare blend of historic charm with a fully renovated interior that was just completed a few years ago. The first level features an open living and dining plan with 10' ceilings, an abundance of natural light, restored Dade County Pine accent walls, plantation shutters, modern lighting, and tile flooring throughout. The kitchen was built to impress and features a large quartz island, Cafe Collection appliances, a gas range, designer tile backsplash, and a separate coffee and cocktail bar. Practical touches include an entry way storage closet, built-in closet systems, and a full-size GE washer and dryer tucked neatly under the stairs. The upstairs primary suite feels like a private retreat.. it features a sitting area with double French doors that open to the balcony perch where you'll enjoy views of beautiful sunsets through the treetops. The en suite bath is finished with gorgeous Onyx Style slab tile, a double vanity, designer fixtures and a glass shower with statement detailing. This luxury condo is offered fully furnished and turnkey, with local Key West history woven throughout. 30-day rentals are allowed with restrictions, it's in the X Flood Zone, and from here it's always an easy stroll to Fort Zach Beach, Truman Waterfront Park, and the Duval Street corridor for fine dining, shopping, and live entertainment, capturing the ease and energy of Key West living..

927 Thomas St Unit #2, Key West

1901 S Roosevelt Blvd Unit 401E, Key West

$1,425,000

Discover the rare opportunity to own a premier developer's unit in one of Key West's most desirable waterfront communities. Perfectly positioned just across the street from world-famous Smathers Beach, this spacious 3-bedroom, 2-bath condo blends coastal luxury with unbeatable island convenience. Inside, expansive living spaces open to large windows and glass doors showcasing ocean views and endless natural light. The open-concept kitchen flows seamlessly into the dining and living areas—ideal for entertaining or relaxing after a day on the sand. Retreat to the ocean-view primary suite, complete with generous closet space and private bath. Two additional bedrooms offer the flexibility for guests, family, a home office, or rental income. Step outside and enjoy resort-style amenities—lush tropical grounds, shoreline paths, sparkling pool, and easy access to water sports, biking, and Key West's sunset scene. Whether you're seeking a primary residence, island getaway, or investment opportunity, this condo delivers everything that makes Key West living unforgettable. Highlights: *Rare developer's unit with expanded layout/premium features *Just steps to Smathers Beach, bike paths & sunrise walks *3 Bedrooms / 2 Bathrooms *Assigned covered parking bay and storage unit *Resort amenities & gated community *Minutes to Old Town, dining, airport & nightlife Your Key West waterfront life starts here—schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ 618248 MLS

Discover the rare opportunity to own a premier developer's unit in one of Key West's most desirable waterfront communities. Perfectly positioned just across the street from world-famous Smathers Beach, this spacious 3-bedroom, 2-bath condo blends coastal luxury with unbeatable island convenience. Inside, expansive living spaces open to large windows and glass doors showcasing ocean views and endless natural light. The open-concept kitchen flows seamlessly into the dining and living areas—ideal for entertaining or relaxing after a day on the sand. Retreat to the ocean-view primary suite, complete with generous closet space and private bath. Two additional bedrooms offer the flexibility for guests, family, a home office, or rental income. Step outside and enjoy resort-style amenities—lush tropical grounds, shoreline paths, sparkling pool, and easy access to water sports, biking, and Key West's sunset scene. Whether you're seeking a primary residence, island getaway, or investment opportunity, this condo delivers everything that makes Key West living unforgettable. Highlights: *Rare developer's unit with expanded layout/premium features *Just steps to Smathers Beach, bike paths & sunrise walks *3 Bedrooms / 2 Bathrooms *Assigned covered parking bay and storage unit *Resort amenities & gated community *Minutes to Old Town, dining, airport & nightlife Your Key West waterfront life starts here—schedule your private showing today!

1901 S Roosevelt Blvd Unit 401E, Key West

$1,175,000

Elegant, peaceful and turn-key, this light-filled, Old Town condo is just one block to Duval Street! This home shines with 23 windows on two levels and relaxes with its easy, breezy, tropical vibe, landscaped grounds and pool. Turn-key, renovated and furnished, this condo resides in the historic Campbell Building on Fleming Street, one of Old Town's most coveted. Enjoy a gorgeous interior with pine floors throughout, new ac mini splits in every room, plentiful storage and a spacious, modern kitchen. The hefty project of converting all 23 windows to impact glass has been done for you, ensuring superior wind protection, an extremely quiet inside space and low energy costs. This unit exudes charm and easy living and feels like a true home all with immediate access to the best of Key West. In a moment you can be dining at your favorite restaurant, watching the sunset at Mallory, listening to live music or hitting Fausto's market for those last minute grocery items. And you will love the balcony where you can take in the hustle and bustle of passer-byers from above, laze away the morning while sipping on your Cuban Coffee, enjoy cocktails under the stars or watch the Fantasy Fest Local's Parade from the best seat in the house! Unit 4 has been fully renovated and needs nothing but you! A custom designed kitchen with ample storage, stainless steel appliances, quartz counters and a white Kohler, porcelain farmer's sink overlooking Fleming below make cooking and entertaining a breeze and a joy. Only 9 units reside in the Campbell Building, all nestled on a beautifully landscaped compound with a large pool. This is a great place to live and will also make for a lucrative vacation rental. Enjoy living on Millionaire's Row with access to all that makes Key West the best place to live the island lifestyle.

2 Beds ⋅ 2 Baths ⋅ 618827 MLS

Elegant, peaceful and turn-key, this light-filled, Old Town condo is just one block to Duval Street! This home shines with 23 windows on two levels and relaxes with its easy, breezy, tropical vibe, landscaped grounds and pool. Turn-key, renovated and furnished, this condo resides in the historic Campbell Building on Fleming Street, one of Old Town's most coveted. Enjoy a gorgeous interior with pine floors throughout, new ac mini splits in every room, plentiful storage and a spacious, modern kitchen. The hefty project of converting all 23 windows to impact glass has been done for you, ensuring superior wind protection, an extremely quiet inside space and low energy costs. This unit exudes charm and easy living and feels like a true home all with immediate access to the best of Key West. In a moment you can be dining at your favorite restaurant, watching the sunset at Mallory, listening to live music or hitting Fausto's market for those last minute grocery items. And you will love the balcony where you can take in the hustle and bustle of passer-byers from above, laze away the morning while sipping on your Cuban Coffee, enjoy cocktails under the stars or watch the Fantasy Fest Local's Parade from the best seat in the house! Unit 4 has been fully renovated and needs nothing but you! A custom designed kitchen with ample storage, stainless steel appliances, quartz counters and a white Kohler, porcelain farmer's sink overlooking Fleming below make cooking and entertaining a breeze and a joy. Only 9 units reside in the Campbell Building, all nestled on a beautifully landscaped compound with a large pool. This is a great place to live and will also make for a lucrative vacation rental. Enjoy living on Millionaire's Row with access to all that makes Key West the best place to live the island lifestyle.

617 Fleming St Unit APT 4, Key West

$4,450,000

Experience the ideal blend of historic charm and modern luxury in this fully renovated and expanded Key West residence, where no detail has been overlooked. Set on a quiet, one-way street in Old Town, this 4-bedroom, 4.5-bath home offers 2,985 square feet of thoughtfully designed living space. Inside, soaring cathedral ceilings and rich Dade County pine walls create a warm, timeless aesthetic. Gorgeous hickory wood floors run throughout, complemented by two custom staircases and striking architectural features. The flexible layout includes a first-floor primary suite with a spa-style bath finished in marble and travertine, plus a second primary suite upstairs that also includes a private office—providing options for comfort, work, and privacy. All of the bathrooms are designed with a serene, spa-like feel, and every upstairs bath includes its own soaking tub for ultimate relaxation. The gourmet kitchen features Miele appliances along with a custom bar complete with a duel zone wine cooler and beverage center—ideal for effortless entertaining. Outdoors, an Ipe deck surrounds the heated and chilled saltwater pool with cascading waterfall features, all controlled by a smart automation system. At the top of the water wall, a decorative propane fire feature adds a dramatic focal point, while an outdoor shower completes your private tropical retreat. Additional features include two off-street parking spaces, impact-rated windows and doors throughout, metal shingle roof and dual-zone central A/C. With designer furnishings included and sold exactly as presented, this residence is ready to enjoy in the heart of Key West's most desirable locations.

4 Beds ⋅ 5 Baths ⋅ 616715 MLS

Experience the ideal blend of historic charm and modern luxury in this fully renovated and expanded Key West residence, where no detail has been overlooked. Set on a quiet, one-way street in Old Town, this 4-bedroom, 4.5-bath home offers 2,985 square feet of thoughtfully designed living space. Inside, soaring cathedral ceilings and rich Dade County pine walls create a warm, timeless aesthetic. Gorgeous hickory wood floors run throughout, complemented by two custom staircases and striking architectural features. The flexible layout includes a first-floor primary suite with a spa-style bath finished in marble and travertine, plus a second primary suite upstairs that also includes a private office—providing options for comfort, work, and privacy. All of the bathrooms are designed with a serene, spa-like feel, and every upstairs bath includes its own soaking tub for ultimate relaxation. The gourmet kitchen features Miele appliances along with a custom bar complete with a duel zone wine cooler and beverage center—ideal for effortless entertaining. Outdoors, an Ipe deck surrounds the heated and chilled saltwater pool with cascading waterfall features, all controlled by a smart automation system. At the top of the water wall, a decorative propane fire feature adds a dramatic focal point, while an outdoor shower completes your private tropical retreat. Additional features include two off-street parking spaces, impact-rated windows and doors throughout, metal shingle roof and dual-zone central A/C. With designer furnishings included and sold exactly as presented, this residence is ready to enjoy in the heart of Key West's most desirable locations.

1113 Stump Ln, Key West

$1,549,000

Rare WATERFRONT home on the island of Key West, an incredible value priced well below the last comparable sale. Tucked behind the gates of the exclusive Gulf View Pointe community, a rare opportunity awaits to own a waterfront townhome in Key West. This three-bedroom, three-full-bath residence offers the luxury of a private pool and includes a dedicated carport. As you step through the front door, you are welcomed into a bright, open home filled with natural light. The spacious kitchen flows seamlessly into the dining and living areas, all offering beautiful water views overlooking the backyard. The first floor also features a bedroom--currently used as a workshop--and a full bathroom. Upstairs, you'll find two bedrooms, each with its own ensuite bath and private deck. The primary suite's deck offers stunning water views. Outdoor living is a highlight of this property. The backyard features a large covered deck leading to the pool, all positioned westward to capture afternoon sun and spectacular sunset views. Plans and permits for your own private dock are already underway. Ideally located, this home offers convenient proximity to local stores and restaurants and is just a bike ride away from everything downtown Key West has to offer. Whether relaxing poolside, enjoying sunset views, or heading out to explore the island lifestyle, every day is framed by comfort, convenience, and the natural beauty of the Gulf.

3 Beds ⋅ 3 Baths ⋅ 618065 MLS

Rare WATERFRONT home on the island of Key West, an incredible value priced well below the last comparable sale. Tucked behind the gates of the exclusive Gulf View Pointe community, a rare opportunity awaits to own a waterfront townhome in Key West. This three-bedroom, three-full-bath residence offers the luxury of a private pool and includes a dedicated carport. As you step through the front door, you are welcomed into a bright, open home filled with natural light. The spacious kitchen flows seamlessly into the dining and living areas, all offering beautiful water views overlooking the backyard. The first floor also features a bedroom--currently used as a workshop--and a full bathroom. Upstairs, you'll find two bedrooms, each with its own ensuite bath and private deck. The primary suite's deck offers stunning water views. Outdoor living is a highlight of this property. The backyard features a large covered deck leading to the pool, all positioned westward to capture afternoon sun and spectacular sunset views. Plans and permits for your own private dock are already underway. Ideally located, this home offers convenient proximity to local stores and restaurants and is just a bike ride away from everything downtown Key West has to offer. Whether relaxing poolside, enjoying sunset views, or heading out to explore the island lifestyle, every day is framed by comfort, convenience, and the natural beauty of the Gulf.

2613 Gulfview Dr, Key West

$4,700,000

A Key West original. 1014 Flagler Avenue is a storied Casa Marina residence shaped by legendary Key West developer David Wolkowsky and set behind privacy walls on an exceptional 11,730-square-foot corner double lot. Some homes are built. Others are authored. At its center: 40 feet of pool, surrounded by mature tropical landscaping and hardscape by Craig Reynolds Landscape Architecture, creating the feel of a private compound hidden in plain sight. Inside, the scale shifts again with 22-foot ceilings, walls of glass, 10-foot doors and sliders, custom teak, and a dramatic floor-to-ceiling library. The main residence offers two bedrooms and two-and-a-half baths, anchored by a chef's kitchen and expansive indoor-outdoor living. Extensive updates include new systems and impact-rated windows and doors. A completely separate one-bedroom guest house adds its own kitchen, laundry and private garden. 3 bedrooms. 3.5 baths. 3,104 square feet. 11,730 square feet of land. 40 feet of pool. In a market full of beautiful houses, 1014 Flagler offers something harder to replicate: a point of view.

3 Beds ⋅ 4 Baths ⋅ 618577 MLS

A Key West original. 1014 Flagler Avenue is a storied Casa Marina residence shaped by legendary Key West developer David Wolkowsky and set behind privacy walls on an exceptional 11,730-square-foot corner double lot. Some homes are built. Others are authored. At its center: 40 feet of pool, surrounded by mature tropical landscaping and hardscape by Craig Reynolds Landscape Architecture, creating the feel of a private compound hidden in plain sight. Inside, the scale shifts again with 22-foot ceilings, walls of glass, 10-foot doors and sliders, custom teak, and a dramatic floor-to-ceiling library. The main residence offers two bedrooms and two-and-a-half baths, anchored by a chef's kitchen and expansive indoor-outdoor living. Extensive updates include new systems and impact-rated windows and doors. A completely separate one-bedroom guest house adds its own kitchen, laundry and private garden. 3 bedrooms. 3.5 baths. 3,104 square feet. 11,730 square feet of land. 40 feet of pool. In a market full of beautiful houses, 1014 Flagler offers something harder to replicate: a point of view.

1014 Flagler Ave, Key West

$1,200,000

Transient receiver site - Truly a diamond in the rough. Great location, behind the Hemingway House between Duval and Whitehead Street. Lot backs up to Whalton Lane (off Duval) with room for parking and a pool. Bring your contractor and a transient license to the property and she will truly shine like the Hope Diamond with happiness and prosperity. Buyers should do their own due diligence to determine transient license receivership requirements prior to making an offer. Probate is required.

3 Beds ⋅ 1 Baths ⋅ 617022 MLS

Transient receiver site - Truly a diamond in the rough. Great location, behind the Hemingway House between Duval and Whitehead Street. Lot backs up to Whalton Lane (off Duval) with room for parking and a pool. Bring your contractor and a transient license to the property and she will truly shine like the Hope Diamond with happiness and prosperity. Buyers should do their own due diligence to determine transient license receivership requirements prior to making an offer. Probate is required.

418 Olivia St, Key West

$1,089,000

Location, Location, Location! Old Town in X-Flood Zone on Solaris Hill with Off Street Parking! Quintessential conch cottage has a cozy front porch & has been in the same family for decades. All wood structure shows a glimpse of wood boards behind the existing interior paneling. This is believed to be the much-desired Dade County Pine. Roof & main electrical panel replaced (w/ permits) in 2014. House is currently configured as seven rooms in total (3 bed, 1 bath, den, dining & kitchen). Front yard provides the highly coveted Off-Street-Parking & the back yard is 31 Ft X 26 Ft (total 806 sq ft). House is a renovation project. This is an estate sale & there will be NO repair and NO clean up by the sellers. However, there will be NO waiting on Probate & NO court approvals needed. Make 719 Elizabeth St your Old Town Island Oasis!

3 Beds ⋅ 1 Baths ⋅ 614442 MLS

Location, Location, Location! Old Town in X-Flood Zone on Solaris Hill with Off Street Parking! Quintessential conch cottage has a cozy front porch & has been in the same family for decades. All wood structure shows a glimpse of wood boards behind the existing interior paneling. This is believed to be the much-desired Dade County Pine. Roof & main electrical panel replaced (w/ permits) in 2014. House is currently configured as seven rooms in total (3 bed, 1 bath, den, dining & kitchen). Front yard provides the highly coveted Off-Street-Parking & the back yard is 31 Ft X 26 Ft (total 806 sq ft). House is a renovation project. This is an estate sale & there will be NO repair and NO clean up by the sellers. However, there will be NO waiting on Probate & NO court approvals needed. Make 719 Elizabeth St your Old Town Island Oasis!

719 Elizabeth St, Key West

$2,033,000

Rare opportunity on desirable Aronovitz Lane in the heart of Key West! This unique offering includes two properties being sold together, creating exceptional flexibility for investors, builders, or lifestyle buyers. The package includes a vacant lot with the ability to rebuild its original two-unit footprint, a true rarity in Key West, presenting an exceptional chance to develop new construction in a prime setting. Paired with this is an existing 2-bedroom, 1-bath home, ideal for island living, income production, or incorporation into a larger architectural vision. Whether you're a builder seeking scarce development rights, an investor looking to maximize returns, or a buyer with a long-term Key West strategy, this is a once-in-a-market opportunity with limitless potential. Quietly tucked away yet steps from Key West's most celebrated dining, galleries, and waterfront experiences. This is Old Town Key West at its absolute best.

2 Beds ⋅ 1 Baths ⋅ 618183 MLS

Rare opportunity on desirable Aronovitz Lane in the heart of Key West! This unique offering includes two properties being sold together, creating exceptional flexibility for investors, builders, or lifestyle buyers. The package includes a vacant lot with the ability to rebuild its original two-unit footprint, a true rarity in Key West, presenting an exceptional chance to develop new construction in a prime setting. Paired with this is an existing 2-bedroom, 1-bath home, ideal for island living, income production, or incorporation into a larger architectural vision. Whether you're a builder seeking scarce development rights, an investor looking to maximize returns, or a buyer with a long-term Key West strategy, this is a once-in-a-market opportunity with limitless potential. Quietly tucked away yet steps from Key West's most celebrated dining, galleries, and waterfront experiences. This is Old Town Key West at its absolute best.

1 & 2 Aronovitz Ln, Key West

$619,000

An easier way to own in Key West. This 2-bedroom, 1.5-bath townhome in the Key West Golf Club gated community offers the simplicity, flexibility, and lifestyle many island buyers are looking for. Whether you want a lock-and-leave second home, a seasonal retreat, a rental-supported investment, or a manageable year-round residence, 48 Merganser Lane gives you a practical path to Key West ownership. The efficient two-story layout separates living and sleeping spaces, while the private outdoor area extends the home's usable living space and creates an easy indoor-outdoor flow. Impact windows add peace of mind, storm protection, and everyday convenience for owners who want a more secure, low-maintenance island home base. Instead of taking on the upkeep demands of a traditional single-family home, you can enjoy a low-maintenance setting with access to resort-style community amenities, including two pools, a fitness center, lush tropical grounds, walking paths, and maintained common areas. The location adds to the appeal. From the Key West Golf Club, you are within easy reach of Old Town, marinas, dining, shopping, entertainment, and the airport, making it convenient for both owners and guests. The community setting offers a quieter residential feel while still keeping the full Key West lifestyle close by. With its manageable size, established community, outdoor living space, rental flexibility, impact windows, and strong lifestyle appeal, 48 Merganser Lane is not just a place to stay in Key West. It is a smart, easy-to-enjoy island home base designed for the way many buyers want to own today.

2 Beds ⋅ 2 Baths ⋅ 617995 MLS

An easier way to own in Key West. This 2-bedroom, 1.5-bath townhome in the Key West Golf Club gated community offers the simplicity, flexibility, and lifestyle many island buyers are looking for. Whether you want a lock-and-leave second home, a seasonal retreat, a rental-supported investment, or a manageable year-round residence, 48 Merganser Lane gives you a practical path to Key West ownership. The efficient two-story layout separates living and sleeping spaces, while the private outdoor area extends the home's usable living space and creates an easy indoor-outdoor flow. Impact windows add peace of mind, storm protection, and everyday convenience for owners who want a more secure, low-maintenance island home base. Instead of taking on the upkeep demands of a traditional single-family home, you can enjoy a low-maintenance setting with access to resort-style community amenities, including two pools, a fitness center, lush tropical grounds, walking paths, and maintained common areas. The location adds to the appeal. From the Key West Golf Club, you are within easy reach of Old Town, marinas, dining, shopping, entertainment, and the airport, making it convenient for both owners and guests. The community setting offers a quieter residential feel while still keeping the full Key West lifestyle close by. With its manageable size, established community, outdoor living space, rental flexibility, impact windows, and strong lifestyle appeal, 48 Merganser Lane is not just a place to stay in Key West. It is a smart, easy-to-enjoy island home base designed for the way many buyers want to own today.

48 Merganser Ln, Key West

$3,599,000

1501 Georgia Street is a masterclass in design. Conceived by local architect Rob Delaune and set within lush, museum worthy grounds by renowned landscape architect Raymond Jungles, this striking 2,810sf residence sits on an expansive 8,800sf lot and captures the essence of tropical modernism. Clean lines. Soaring ceilings. Walls of glass. A seamless and intentional dialogue between indoors and out. This is true Mid Century Modern, authentically executed. A single story design with 4 bedrooms and 4.5 baths, wrapped in glass and stone, where skylights, pocket doors, and oversized windows flood the interiors with natural light. Every room frames the landscape, transforming the gardens into living artwork. Designed for both refined entertaining & comfortable family living, the home features stone floors throughout and a modern floor plan with garden views in every direction. Natural light fills the interiors, blurring the boundary between architecture and nature and creating a seamless indoor outdoor lifestyle that defines island living. At the heart of the home, a newly renovated showpiece kitchen elevates everyday life and gatherings alike, featuring dramatic Cambria quartz countertops with a waterfall island, warm wood cabinetry, pendant lighting, and stainless steel appliances. A full wall opens directly to the 55 foot heated and chilled saltwater pool and stone terrace, creating effortless flow for events large or intimate. The primary suite offers privacy and tranquil garden views, while all four bedrooms provide generous proportions and high ceilings. Oversized glass highlights the extraordinary tropical landscaping surrounding the home. The grounds showcase native and exotic flora from around the world, tropical atriums, a water garden with koi, multiple water features, an outdoor shower, and exceptional privacy inside & out. Properties of this caliber and architectural significance rarely become available, so don't wait, schedule your private showing today!

4 Beds ⋅ 5 Baths ⋅ 618829 MLS

1501 Georgia Street is a masterclass in design. Conceived by local architect Rob Delaune and set within lush, museum worthy grounds by renowned landscape architect Raymond Jungles, this striking 2,810sf residence sits on an expansive 8,800sf lot and captures the essence of tropical modernism. Clean lines. Soaring ceilings. Walls of glass. A seamless and intentional dialogue between indoors and out. This is true Mid Century Modern, authentically executed. A single story design with 4 bedrooms and 4.5 baths, wrapped in glass and stone, where skylights, pocket doors, and oversized windows flood the interiors with natural light. Every room frames the landscape, transforming the gardens into living artwork. Designed for both refined entertaining & comfortable family living, the home features stone floors throughout and a modern floor plan with garden views in every direction. Natural light fills the interiors, blurring the boundary between architecture and nature and creating a seamless indoor outdoor lifestyle that defines island living. At the heart of the home, a newly renovated showpiece kitchen elevates everyday life and gatherings alike, featuring dramatic Cambria quartz countertops with a waterfall island, warm wood cabinetry, pendant lighting, and stainless steel appliances. A full wall opens directly to the 55 foot heated and chilled saltwater pool and stone terrace, creating effortless flow for events large or intimate. The primary suite offers privacy and tranquil garden views, while all four bedrooms provide generous proportions and high ceilings. Oversized glass highlights the extraordinary tropical landscaping surrounding the home. The grounds showcase native and exotic flora from around the world, tropical atriums, a water garden with koi, multiple water features, an outdoor shower, and exceptional privacy inside & out. Properties of this caliber and architectural significance rarely become available, so don't wait, schedule your private showing today!

1501 Georgia St, Key West

$3,750,000

Charming Single family home with multiple guest cottages in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional compound, perfectly situated in a vibrant neighborhood. This property offers a unique blend of charm and modern comfort, making it an ideal investment or family retreat. The compound consists of 4 units, each exuding the distinctive character of Key West architecture, featuring high ceilings, large windows that invite natural light. The main house has its own private heated pool, hot tub and outdoor shower perfect for relaxation and entertainment. The main house also has 2 guest cottages off the pool. The next building has an upstairs unit with 2 bedrooms and a bath with it's own private deck. Below is a one bedroom one bath unit and up front is the 3rd unit with one bedroom and one bath. Benefit from plenty of parking spaces, accommodating residents and guests with ease a rare find in this bustling area. Nestled in one of Key West's most historic districts, this property is just minutes away from famous landmarks, restaurants, and local shops. Take advantage of nearby beaches, water sports, and lush parks, offering a vibrant lifestyle for outdoor enthusiasts. This multifamily compound not only serves as a wonderful family home but also presents a lucrative rental opportunity in one of the most sought-after destinations in Florida. Don't miss your chance to own a piece of Key West history. Schedule a viewing today. Owner financing is available.

7 Beds ⋅ 8 Baths ⋅ 618468 MLS

Charming Single family home with multiple guest cottages in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional compound, perfectly situated in a vibrant neighborhood. This property offers a unique blend of charm and modern comfort, making it an ideal investment or family retreat. The compound consists of 4 units, each exuding the distinctive character of Key West architecture, featuring high ceilings, large windows that invite natural light. The main house has its own private heated pool, hot tub and outdoor shower perfect for relaxation and entertainment. The main house also has 2 guest cottages off the pool. The next building has an upstairs unit with 2 bedrooms and a bath with it's own private deck. Below is a one bedroom one bath unit and up front is the 3rd unit with one bedroom and one bath. Benefit from plenty of parking spaces, accommodating residents and guests with ease a rare find in this bustling area. Nestled in one of Key West's most historic districts, this property is just minutes away from famous landmarks, restaurants, and local shops. Take advantage of nearby beaches, water sports, and lush parks, offering a vibrant lifestyle for outdoor enthusiasts. This multifamily compound not only serves as a wonderful family home but also presents a lucrative rental opportunity in one of the most sought-after destinations in Florida. Don't miss your chance to own a piece of Key West history. Schedule a viewing today. Owner financing is available.

919-921 Thomas St, Key West

$1,899,000

Located on a corner lot in the highly sought-after Meadows neighborhood, this beautifully crafted Key West home offers exceptional design, privacy, and outdoor living. Built new in 2008 with top-of-the-line materials and superior craftsmanship, the residence features 2 bedrooms, 2.5 baths, and dramatic architectural details throughout. Upon entry, you are welcomed by soaring 11-foot ceilings and an expansive open living space highlighted by travertine tile flooring and abundant natural light. Eight-foot hurricane-rated sliding glass doors seamlessly connect the interior to a private, beautifully landscaped patio with a heated pool and spa--perfect for entertaining or relaxing in your own tropical retreat. The gourmet kitchen overlooks the living area and is appointed with custom solid wood cabinetry, granite countertops, and premium stainless steel appliances, including a six-burner gas range. Rich hardwood floors continue throughout the home, complemented by crown molding, high baseboards, and custom trim. Upstairs, both guest and primary suites are designed for comfort and privacy. The guest suite features its own private staircase, vaulted tray ceiling, and ensuite bath. The spacious primary suite is a true sanctuary, offering vaulted ceilings, multiple closets, abundant natural light, and access to a wide private balcony. The luxurious primary bath adds to the home's refined appeal. Additional features include Hardiboard siding, impact windows and doors, a metal roof, and a private carport with storage accessed through electronic gates. The fully fenced property is surrounded by lush tropical landscaping and is adjacent to a protected basin with native tropical flora, enhancing privacy and tranquility. Enjoy easy, low-maintenance living just a short stroll to Old Town and the Seaport--this is island living at its finest.

2 Beds ⋅ 3 Baths ⋅ 618826 MLS

Located on a corner lot in the highly sought-after Meadows neighborhood, this beautifully crafted Key West home offers exceptional design, privacy, and outdoor living. Built new in 2008 with top-of-the-line materials and superior craftsmanship, the residence features 2 bedrooms, 2.5 baths, and dramatic architectural details throughout. Upon entry, you are welcomed by soaring 11-foot ceilings and an expansive open living space highlighted by travertine tile flooring and abundant natural light. Eight-foot hurricane-rated sliding glass doors seamlessly connect the interior to a private, beautifully landscaped patio with a heated pool and spa--perfect for entertaining or relaxing in your own tropical retreat. The gourmet kitchen overlooks the living area and is appointed with custom solid wood cabinetry, granite countertops, and premium stainless steel appliances, including a six-burner gas range. Rich hardwood floors continue throughout the home, complemented by crown molding, high baseboards, and custom trim. Upstairs, both guest and primary suites are designed for comfort and privacy. The guest suite features its own private staircase, vaulted tray ceiling, and ensuite bath. The spacious primary suite is a true sanctuary, offering vaulted ceilings, multiple closets, abundant natural light, and access to a wide private balcony. The luxurious primary bath adds to the home's refined appeal. Additional features include Hardiboard siding, impact windows and doors, a metal roof, and a private carport with storage accessed through electronic gates. The fully fenced property is surrounded by lush tropical landscaping and is adjacent to a protected basin with native tropical flora, enhancing privacy and tranquility. Enjoy easy, low-maintenance living just a short stroll to Old Town and the Seaport--this is island living at its finest.

1513 Pine St, Key West

$3,750,000

Charming Multifamily Compound in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional multifamily compound, perfectly situated in a vibrant neighborhood. This property offers a unique blend of charm and modern comfort, making it an ideal investment or family retreat. The compound consists of 4 units, each exuding the distinctive character of Key West architecture, featuring high ceilings, large windows that invite natural light. The main house has its own private heated pool, hot tub and outdoor shower perfect for relaxation and entertainment. The main house also has 2 guest cottages off the pool. The next building has an upstairs unit with 2 bedrooms and a bath with it's own private deck. Below is a one bedroom one bath unit and up front is the 3rd unit with one bedroom and one bath. Benefit from plenty of parking spaces, accommodating residents and guests with ease a rare find in this bustling area. Nestled in one of Key West's most historic districts, this property is just minutes away from famous landmarks, restaurants, and local shops. Take advantage of nearby beaches, water sports, and lush parks, offering a vibrant lifestyle for outdoor enthusiasts. This multifamily compound not only serves as a wonderful family home but also presents a lucrative rental opportunity in one of the most sought-after destinations in Florida. Don't miss your chance to own a piece of Key West history. Schedule a viewing today. Owner financing is available.

7 Beds ⋅ 8 Baths ⋅ 617140 MLS

Charming Multifamily Compound in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional multifamily compound, perfectly situated in a vibrant neighborhood. This property offers a unique blend of charm and modern comfort, making it an ideal investment or family retreat. The compound consists of 4 units, each exuding the distinctive character of Key West architecture, featuring high ceilings, large windows that invite natural light. The main house has its own private heated pool, hot tub and outdoor shower perfect for relaxation and entertainment. The main house also has 2 guest cottages off the pool. The next building has an upstairs unit with 2 bedrooms and a bath with it's own private deck. Below is a one bedroom one bath unit and up front is the 3rd unit with one bedroom and one bath. Benefit from plenty of parking spaces, accommodating residents and guests with ease a rare find in this bustling area. Nestled in one of Key West's most historic districts, this property is just minutes away from famous landmarks, restaurants, and local shops. Take advantage of nearby beaches, water sports, and lush parks, offering a vibrant lifestyle for outdoor enthusiasts. This multifamily compound not only serves as a wonderful family home but also presents a lucrative rental opportunity in one of the most sought-after destinations in Florida. Don't miss your chance to own a piece of Key West history. Schedule a viewing today. Owner financing is available.

919-921 Thomas St, Key West

2601 S Roosevelt Blvd Unit 304C, Key West

$799,000

Enjoy relaxed island living in this spacious 3-bedroom, 2-bath condo located in the gated community of Key West by the Sea, directly across from Smathers Beach. This bright and comfortable residence offers an open living and dining area, a private balcony with tropical surroundings, and a thoughtful layout ideal for everyday living or hosting guests. Residents enjoy resort-style amenities including two swimming pools, tennis courts, a clubhouse, and beautifully landscaped grounds. Conveniently located near beaches, shopping, dining, and all the attractions of Old Town Key West, this condo is perfect as a primary residence, second home, or island getaway.

3 Beds ⋅ 2 Baths ⋅ 618386 MLS

Enjoy relaxed island living in this spacious 3-bedroom, 2-bath condo located in the gated community of Key West by the Sea, directly across from Smathers Beach. This bright and comfortable residence offers an open living and dining area, a private balcony with tropical surroundings, and a thoughtful layout ideal for everyday living or hosting guests. Residents enjoy resort-style amenities including two swimming pools, tennis courts, a clubhouse, and beautifully landscaped grounds. Conveniently located near beaches, shopping, dining, and all the attractions of Old Town Key West, this condo is perfect as a primary residence, second home, or island getaway.

2601 S Roosevelt Blvd Unit 304C, Key West