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Welcome to 1422 Catherine Street in The Heart of Key West. Two structures with a total of two (2) bedrooms and two (2) bathrooms. The front structure is a one (1) bedroom and one (1) bathroom and the back structure is also a one (1) bedroom and one (1) bathroom. The front structure has just recently gone through a major improvement, totally redone foundation with concrete, new floors and totally updated. Outdoors is a perfect courtyard for dining under the stars or just hanging out and solving all the world's problems. There are also washer and dryer hook ups and an outdoor shower. This home is perfect for full time residents, second home or a great rental property. Call today for your private showing!

2 Beds ⋅ 2 Baths ⋅ 621112 MLS

Welcome to 1422 Catherine Street in The Heart of Key West. Two structures with a total of two (2) bedrooms and two (2) bathrooms. The front structure is a one (1) bedroom and one (1) bathroom and the back structure is also a one (1) bedroom and one (1) bathroom. The front structure has just recently gone through a major improvement, totally redone foundation with concrete, new floors and totally updated. Outdoors is a perfect courtyard for dining under the stars or just hanging out and solving all the world's problems. There are also washer and dryer hook ups and an outdoor shower. This home is perfect for full time residents, second home or a great rental property. Call today for your private showing!

1422 Catherine St, Key West

$836,000

WELCOME TO THE SANCTUARY-where privacy, tropical beauty, classic Key West style come together! Beyond the 2nd set of gates @ Key West Golf Club, this pristine courtyard spa home enjoys an enviable END LOCATION along a picturesque palm-lined lane. A RARE distinction: the ONLY one of 21 Sanctuary spa homes offering covered-carport access directly into the private courtyard/side yard! Classic KW charm begins at the wide front veranda, framed by vibrant tropical landscaping, polished stone & freshly painted exterior. Inside, natural light fills the inviting open floor plan w/taller ceilings & easy indoor/outdoor flow. The spacious island kitchen features granite countertops, abundant cabinetry/storage, all stainless-steel appliances, new dishwasher, mosaic tile backsplash & new 5-light Tiffany-style fixture delicately adorns the island. Extended granite surfaces offer generous prep space while the island opens beautifully to the great room. Cozy recessed lighting sets the ambiance, spacious enough to allow for beautiful dining setting. Double French doors off the living room reveal a private tropical courtyard--brick pavers, lush established gardens & covered outdoor living surround your own inground jacuzzi spa. Morning coffee, alfresco dining or an evening soak beneath the palms...this is quintessential Keys living! Upstairs are 2 generously sized bedrooms, each w/soaring vaulted ceilings & private en-suite bath. Primary bath offers expanded granite countertop, vessel-style sink, porcelain tub/shower glass doors & clever built-in towel storage. Guest bedroom is spacious w/a bath featuring upgraded lighting & tiled corner shower. Extras include on-demand hot water heater, storm shutters for most doors/windows, stack W/D, under-stair storage, termite protection plan. Enjoy KWGC's 24-hr Resident Services, 2 stunning pools (one w/tropical waterfalls), clubhouse/fitness center, lush Rees Jones-designed 18-hole golf course. A private Sanctuary retreat distinctly its own

2 Beds ⋅ 3 Baths ⋅ 621063 MLS

WELCOME TO THE SANCTUARY-where privacy, tropical beauty, classic Key West style come together! Beyond the 2nd set of gates @ Key West Golf Club, this pristine courtyard spa home enjoys an enviable END LOCATION along a picturesque palm-lined lane. A RARE distinction: the ONLY one of 21 Sanctuary spa homes offering covered-carport access directly into the private courtyard/side yard! Classic KW charm begins at the wide front veranda, framed by vibrant tropical landscaping, polished stone & freshly painted exterior. Inside, natural light fills the inviting open floor plan w/taller ceilings & easy indoor/outdoor flow. The spacious island kitchen features granite countertops, abundant cabinetry/storage, all stainless-steel appliances, new dishwasher, mosaic tile backsplash & new 5-light Tiffany-style fixture delicately adorns the island. Extended granite surfaces offer generous prep space while the island opens beautifully to the great room. Cozy recessed lighting sets the ambiance, spacious enough to allow for beautiful dining setting. Double French doors off the living room reveal a private tropical courtyard--brick pavers, lush established gardens & covered outdoor living surround your own inground jacuzzi spa. Morning coffee, alfresco dining or an evening soak beneath the palms...this is quintessential Keys living! Upstairs are 2 generously sized bedrooms, each w/soaring vaulted ceilings & private en-suite bath. Primary bath offers expanded granite countertop, vessel-style sink, porcelain tub/shower glass doors & clever built-in towel storage. Guest bedroom is spacious w/a bath featuring upgraded lighting & tiled corner shower. Extras include on-demand hot water heater, storm shutters for most doors/windows, stack W/D, under-stair storage, termite protection plan. Enjoy KWGC's 24-hr Resident Services, 2 stunning pools (one w/tropical waterfalls), clubhouse/fitness center, lush Rees Jones-designed 18-hole golf course. A private Sanctuary retreat distinctly its own

210 Golf Club Dr, Key West

$2,599,000

Welcome to a stunning transformation of a perfectly located Old Town home. Restored from the ground up to create a single level dream home totaling 3bd/2ba overlooking a beautiful pool and patio. Enjoy an open floor plan where the kitchen is truly the heart of the home complete with top of the line stainless Thermador appliances, quartz countertops and timeless cabinetry with a central island perfect for entertaining! Matching custom cabinetry extends into the quaint living room space offering thoughtful built in storage and a beautiful entertainment backdrop. Reclaimed Dade County pine has been lovingly restored into an accent wall rich with history and elegance. Vaulted ceilings finished in grasscloth and wood beams are found in every room of this home. Enjoy 2 spacious ensuite luxury bathrooms and a gorgeous poolside outdoor shower. Low maintenance composite decking surrounds the home and pool area that accommodates dining and lounging in or out of the pool with a sun shelf and waterfall. Lets not forget the darling covered front porch that welcomes you to this quiet lane cottage also offering off street parking. Carsten Lane is a one way driving lane stretching only one block located in the heart of Old Town known for its peaceful and private setting!

3 Beds ⋅ 2 Baths ⋅ 621061 MLS

Welcome to a stunning transformation of a perfectly located Old Town home. Restored from the ground up to create a single level dream home totaling 3bd/2ba overlooking a beautiful pool and patio. Enjoy an open floor plan where the kitchen is truly the heart of the home complete with top of the line stainless Thermador appliances, quartz countertops and timeless cabinetry with a central island perfect for entertaining! Matching custom cabinetry extends into the quaint living room space offering thoughtful built in storage and a beautiful entertainment backdrop. Reclaimed Dade County pine has been lovingly restored into an accent wall rich with history and elegance. Vaulted ceilings finished in grasscloth and wood beams are found in every room of this home. Enjoy 2 spacious ensuite luxury bathrooms and a gorgeous poolside outdoor shower. Low maintenance composite decking surrounds the home and pool area that accommodates dining and lounging in or out of the pool with a sun shelf and waterfall. Lets not forget the darling covered front porch that welcomes you to this quiet lane cottage also offering off street parking. Carsten Lane is a one way driving lane stretching only one block located in the heart of Old Town known for its peaceful and private setting!

812 Carsten Ln, Key West

$799,000

This elegant historic Old Town cottage is a rare offering paired with a highly competitive price. Completely turnkey and perfectly suited as a winter home or seasonal Key West escape, it offers the opportunity to simply arrive, settle in, and enjoy island life from day one. Sparkling, gallery-like, and filled with natural light, this beautifully renovated Old Town Key West cottage offers the perfect blend of charm, privacy, and modern comfort. Ideally situated on a quiet one-way street, this tropical retreat is just a short stroll from some of Key West's best boutiques, bakeries, art galleries, restaurants, and gourmet food markets. Renovated down to the studs, the home features vaulted ceilings and an open-concept layout where the gourmet kitchen, entertainment bar, and living area come together to create a bright, welcoming gathering space. True to the Key West lifestyle, an expansive sliding glass door opens to a serene tropical oasis framed by lush fig vines, Spanish lime trees, swaying palms, and a majestic Royal Poinciana tree, where morning coffee, afternoon cocktails, and evenings under the stars become part of everyday life. The property also offers dedicated off-street golf cart parking, potential for a small pool, and no HOA fees, further enhancing its appeal as a private sanctuary. Thoughtfully selected upscale finishes include solid teak flooring, granite countertops, and a beautifully appointed Calacatta marble shower tub. The renovation includes all-new electrical and plumbing systems, an efficient tankless hot water heater, a metal roof, impact-rated windows and opening protections, and stylish finishes throughout. Situated in the desirable X Flood Zone, the property offers an added layer of peace of mind with reduced flood risk concerns. Steeped in Key West history, this charming cottage was once home to a local cigar maker, offering a connection to the island's rich cultural heritage while embracing the pleasures of contemporary living.

1 Beds ⋅ 1 Baths ⋅ 621059 MLS

This elegant historic Old Town cottage is a rare offering paired with a highly competitive price. Completely turnkey and perfectly suited as a winter home or seasonal Key West escape, it offers the opportunity to simply arrive, settle in, and enjoy island life from day one. Sparkling, gallery-like, and filled with natural light, this beautifully renovated Old Town Key West cottage offers the perfect blend of charm, privacy, and modern comfort. Ideally situated on a quiet one-way street, this tropical retreat is just a short stroll from some of Key West's best boutiques, bakeries, art galleries, restaurants, and gourmet food markets. Renovated down to the studs, the home features vaulted ceilings and an open-concept layout where the gourmet kitchen, entertainment bar, and living area come together to create a bright, welcoming gathering space. True to the Key West lifestyle, an expansive sliding glass door opens to a serene tropical oasis framed by lush fig vines, Spanish lime trees, swaying palms, and a majestic Royal Poinciana tree, where morning coffee, afternoon cocktails, and evenings under the stars become part of everyday life. The property also offers dedicated off-street golf cart parking, potential for a small pool, and no HOA fees, further enhancing its appeal as a private sanctuary. Thoughtfully selected upscale finishes include solid teak flooring, granite countertops, and a beautifully appointed Calacatta marble shower tub. The renovation includes all-new electrical and plumbing systems, an efficient tankless hot water heater, a metal roof, impact-rated windows and opening protections, and stylish finishes throughout. Situated in the desirable X Flood Zone, the property offers an added layer of peace of mind with reduced flood risk concerns. Steeped in Key West history, this charming cottage was once home to a local cigar maker, offering a connection to the island's rich cultural heritage while embracing the pleasures of contemporary living.

1105 Olivia St, Key West

$999,000

2809 Flagler Ave -2,274 Square Feet of Space, Priced to Move Rarely does a home this size come up in Key West at this price point. At 2,274 square feet, this 4-bedroom, 2-bathroom residence offers significantly more room than the typical Old Town or Mid Town property -- and it's priced well below what comparable square footage commands elsewhere in the 33040 zip code. Originally built in 1953, the home received a two-story addition in 2002 that expanded both living space and functionality, giving it a layout that feels far more generous than its neighbors. Inside, 3/4-inch red oak flooring runs throughout, and every bedroom includes its own closet for real storage -- not an afterthought. A spacious office/flex room adds even more usable square footage, ideal as a home office, guest space, or additional living area. A dedicated laundry room and a large pantry/storage area off the carport round out the practical extras that are hard to find in homes half this size.

4 Beds ⋅ 2 Baths ⋅ 621054 MLS

2809 Flagler Ave -2,274 Square Feet of Space, Priced to Move Rarely does a home this size come up in Key West at this price point. At 2,274 square feet, this 4-bedroom, 2-bathroom residence offers significantly more room than the typical Old Town or Mid Town property -- and it's priced well below what comparable square footage commands elsewhere in the 33040 zip code. Originally built in 1953, the home received a two-story addition in 2002 that expanded both living space and functionality, giving it a layout that feels far more generous than its neighbors. Inside, 3/4-inch red oak flooring runs throughout, and every bedroom includes its own closet for real storage -- not an afterthought. A spacious office/flex room adds even more usable square footage, ideal as a home office, guest space, or additional living area. A dedicated laundry room and a large pantry/storage area off the carport round out the practical extras that are hard to find in homes half this size.

2809 Flagler Ave, Key West

$1,490,000

Welcome to 1724 Rose Street, a spacious single-family home on a generous corner lot in a quiet Midtown neighborhood, close to Key West's beautiful beaches. The main level features an inviting open-concept kitchen, dining, and living area, along with three bedrooms and two baths. Freshly painted inside and out, the home is move-in ready while offering an opportunity to add your own personal touches and updates. The upstairs addition was done in 2016 offering two additional studio spaces. Both studios provide exceptional flexibility and could potentially be configured with a separate entrance, making them ideal for guests, extended family, a home office, or additional living accommodations. The large corner lot offers off-street parking for 2-3 vehicles, plus abundant on street parking. Out back, the spacious yard has plenty of room to create your own private oasis, with space for a large pool, outdoor lounging and entertaining areas, plus ample storage. With its flexible layout, generous lot, parking, and desirable Midtown location, this property offers numerous possibilities--from a comfortable home for a large family to monthly vacation rental use or employee housing. A rare opportunity to create a spacious Key West retreat with room to grow, customize, and enjoy the island lifestyle.

5 Beds ⋅ 4 Baths ⋅ 621031 MLS

Welcome to 1724 Rose Street, a spacious single-family home on a generous corner lot in a quiet Midtown neighborhood, close to Key West's beautiful beaches. The main level features an inviting open-concept kitchen, dining, and living area, along with three bedrooms and two baths. Freshly painted inside and out, the home is move-in ready while offering an opportunity to add your own personal touches and updates. The upstairs addition was done in 2016 offering two additional studio spaces. Both studios provide exceptional flexibility and could potentially be configured with a separate entrance, making them ideal for guests, extended family, a home office, or additional living accommodations. The large corner lot offers off-street parking for 2-3 vehicles, plus abundant on street parking. Out back, the spacious yard has plenty of room to create your own private oasis, with space for a large pool, outdoor lounging and entertaining areas, plus ample storage. With its flexible layout, generous lot, parking, and desirable Midtown location, this property offers numerous possibilities--from a comfortable home for a large family to monthly vacation rental use or employee housing. A rare opportunity to create a spacious Key West retreat with room to grow, customize, and enjoy the island lifestyle.

1724 Rose St, Key West

$2,550,000

Welcome to 1202 Royal Street, a beautifully reimagined and rebuilt Key West residence where thoughtful design, modern construction, and exceptional Old Town location come together. Featuring four (4) bedrooms and three-and-a-half (3.5) bathrooms, this property has been rebuilt from the ground up with meticulous attention to detail. Located in coveted Historic Old Town and the highly desirable X Flood Zone, 1202 Royal Street places you in the heart of everything that makes Key West special. Step through the stunning mahogany hurricane-impact front door into a bright interior with soaring ceilings, natural light, and a striking floating staircase leading to the second floor. The home flows effortlessly into an expansive open-concept kitchen and living area designed for both everyday living and entertaining. Open the home to your private backyard, where IPE decking, a heated and chilled pool, and separate hot tub create the perfect indoor/outdoor lifestyle and an ideal setting for entertaining family and friends. The ground-floor primary suite offers privacy from the rest of the home and features a beautiful ensuite bath. Upstairs, two additional bedrooms share a thoughtfully designed Jack-and-Jill bathroom, providing comfortable accommodations for family and guests. The detached guest house, configured as a legal duplex with separate water and electric meters, adds tremendous versatility. Use it as a luxurious pool house, private guest quarters, additional primary suite, or completely separate living space. Additional features include impact windows and doors, spray-foam insulation, IPE decking, two A/C zones in the main residence, ductless climate control in the guest house, fire sprinkler systems in both residences, and numerous additional upgrades throughout. Come experience 1202 Royal Street and discover what it means to live like royalty in Key West!

4 Beds ⋅ 4 Baths ⋅ 620994 MLS

Welcome to 1202 Royal Street, a beautifully reimagined and rebuilt Key West residence where thoughtful design, modern construction, and exceptional Old Town location come together. Featuring four (4) bedrooms and three-and-a-half (3.5) bathrooms, this property has been rebuilt from the ground up with meticulous attention to detail. Located in coveted Historic Old Town and the highly desirable X Flood Zone, 1202 Royal Street places you in the heart of everything that makes Key West special. Step through the stunning mahogany hurricane-impact front door into a bright interior with soaring ceilings, natural light, and a striking floating staircase leading to the second floor. The home flows effortlessly into an expansive open-concept kitchen and living area designed for both everyday living and entertaining. Open the home to your private backyard, where IPE decking, a heated and chilled pool, and separate hot tub create the perfect indoor/outdoor lifestyle and an ideal setting for entertaining family and friends. The ground-floor primary suite offers privacy from the rest of the home and features a beautiful ensuite bath. Upstairs, two additional bedrooms share a thoughtfully designed Jack-and-Jill bathroom, providing comfortable accommodations for family and guests. The detached guest house, configured as a legal duplex with separate water and electric meters, adds tremendous versatility. Use it as a luxurious pool house, private guest quarters, additional primary suite, or completely separate living space. Additional features include impact windows and doors, spray-foam insulation, IPE decking, two A/C zones in the main residence, ductless climate control in the guest house, fire sprinkler systems in both residences, and numerous additional upgrades throughout. Come experience 1202 Royal Street and discover what it means to live like royalty in Key West!

1202 Royal St, Key West

$1,500,000

Located within the private Sanctuary enclave of the Key West Golf Club, this 4-bedroom, 3-bath residence offers rare privacy, coveted west-facing sunset exposure, and direct frontage along the 18th hole of the Rees Jones-designed course, all within the City of Key West. With approximately only 10 homes in the entire Key West Golf Club community offering 1,800 square feet or more of living space, opportunities at this size are exceptionally limited and rarely come to market. Inside, new tile flooring runs throughout, complementing a bright, open floor plan designed for effortless everyday living and relaxed entertaining. Expansive living and dining areas are filled with natural light and transition seamlessly to the outdoor space, where a private pool overlooks manicured fairways and wide-open skies. The setting is tailor-made for sunset gatherings, evening swims, or simply unwinding as the sun drops over the course. The well-appointed kitchen remains connected to the main living areas, creating a functional and social heart of the home. Generously sized bedrooms provide flexibility for guests, family, or a dedicated home office. Upstairs, a private balcony captures elevated golf course views and dramatic western skies, offering a peaceful retreat that feels distinctly removed from the everyday. The double-gated Sanctuary adds an extra layer of privacy and security, while residents enjoy access to two community pools and a fitness center. The golf clubhouse is just a short walk away. Nearby dining and daily conveniences allow you to enjoy the island lifestyle without always heading downtown, while Old Town Key West remains just minutes away. Approximately 15 minutes from the historic district, this property delivers a rare balance of tranquil gated living and easy access to beaches, boating, dining, and the vibrant energy that defines Key West. A sunset-facing golf course residence of this size, in this setting doesn't come around often!

4 Beds ⋅ 3 Baths ⋅ 620988 MLS

Located within the private Sanctuary enclave of the Key West Golf Club, this 4-bedroom, 3-bath residence offers rare privacy, coveted west-facing sunset exposure, and direct frontage along the 18th hole of the Rees Jones-designed course, all within the City of Key West. With approximately only 10 homes in the entire Key West Golf Club community offering 1,800 square feet or more of living space, opportunities at this size are exceptionally limited and rarely come to market. Inside, new tile flooring runs throughout, complementing a bright, open floor plan designed for effortless everyday living and relaxed entertaining. Expansive living and dining areas are filled with natural light and transition seamlessly to the outdoor space, where a private pool overlooks manicured fairways and wide-open skies. The setting is tailor-made for sunset gatherings, evening swims, or simply unwinding as the sun drops over the course. The well-appointed kitchen remains connected to the main living areas, creating a functional and social heart of the home. Generously sized bedrooms provide flexibility for guests, family, or a dedicated home office. Upstairs, a private balcony captures elevated golf course views and dramatic western skies, offering a peaceful retreat that feels distinctly removed from the everyday. The double-gated Sanctuary adds an extra layer of privacy and security, while residents enjoy access to two community pools and a fitness center. The golf clubhouse is just a short walk away. Nearby dining and daily conveniences allow you to enjoy the island lifestyle without always heading downtown, while Old Town Key West remains just minutes away. Approximately 15 minutes from the historic district, this property delivers a rare balance of tranquil gated living and easy access to beaches, boating, dining, and the vibrant energy that defines Key West. A sunset-facing golf course residence of this size, in this setting doesn't come around often!

193 Golf Club Dr, Key West

$759,000

Opportunity in the desirable Lime Grove neighborhood of New Town Key West! Situated on an oversized corner lot, this CBS home offers 1,242 sq. ft. of living area, an expansive yard and plenty of possibilities for its next owner. Owned by the same family for decades, the property has been lovingly maintained and is ready for its next chapter. Originally designed as a three-bedroom home, two of the bedrooms were opened into one another by removing the dividing wall, creating one oversized bedroom. The third bedroom remains separate, and the original three-bedroom configuration could potentially be restored by a new owner by adding the dividing wall. The generous corner lot provides abundant outdoor space with plenty of room to create a tropical outdoor living area and potential for a pool. The property also includes a detached 483 sq. ft. CBS garage/workshop in need of significant repair and rehabilitation, offering the potential to restore and repurpose the structure. Attached to the rear of the garage is a 228 sq. ft. utility/laundry/storage space. Inside, the home retains much of its original character with ample potential for updating and personalization. Whether envisioned as a primary residence, long-term rental investment or renovation project, the spacious lot, CBS construction, flexible layout and New Town location provide a great foundation for its next chapter. Just steps from Lake McKillip, take an evening stroll along the public wooden walkway over the water and enjoy beautiful Key West sunsets. Conveniently located in New Town near shopping centers, schools, the senior center, beaches and everything the island has to offer. Bring your vision and discover the possibilities at 2804 Harris Avenue.

2 Beds ⋅ 1 Baths ⋅ 620989 MLS

Opportunity in the desirable Lime Grove neighborhood of New Town Key West! Situated on an oversized corner lot, this CBS home offers 1,242 sq. ft. of living area, an expansive yard and plenty of possibilities for its next owner. Owned by the same family for decades, the property has been lovingly maintained and is ready for its next chapter. Originally designed as a three-bedroom home, two of the bedrooms were opened into one another by removing the dividing wall, creating one oversized bedroom. The third bedroom remains separate, and the original three-bedroom configuration could potentially be restored by a new owner by adding the dividing wall. The generous corner lot provides abundant outdoor space with plenty of room to create a tropical outdoor living area and potential for a pool. The property also includes a detached 483 sq. ft. CBS garage/workshop in need of significant repair and rehabilitation, offering the potential to restore and repurpose the structure. Attached to the rear of the garage is a 228 sq. ft. utility/laundry/storage space. Inside, the home retains much of its original character with ample potential for updating and personalization. Whether envisioned as a primary residence, long-term rental investment or renovation project, the spacious lot, CBS construction, flexible layout and New Town location provide a great foundation for its next chapter. Just steps from Lake McKillip, take an evening stroll along the public wooden walkway over the water and enjoy beautiful Key West sunsets. Conveniently located in New Town near shopping centers, schools, the senior center, beaches and everything the island has to offer. Bring your vision and discover the possibilities at 2804 Harris Avenue.

2804 Harris Ave, Key West

$999,000

Charming Historic Old Town Key West Home, Ready for Its Next Chapter! Here's an opportunity for the buyer who sees possibility where others see a project. This 3-bedroom, 1.5-bath historic Key West home is tucked into the heart of Old Town, just minutes from the Historic Seaport, downtown, restaurants, shopping, and everything that makes island living so special. With classic Key West architecture, a welcoming front porch, hardwood floors, vintage windows, and plenty of original character, the home offers a wonderful starting point for a thoughtful renovation. The interior has been freshly painted, but this is a property that will require renovation and is best suited for a buyer ready to take on a true restoration project. Currently tenant occupied, the property also offers the advantage of existing rental income while a new owner makes plans, lines up contractors, or prepares for a future renovation or move-in. The existing floor plan includes generous living space, three bedrooms, a full bath downstairs, a half bath upstairs, and a private backyard with the potential to become a lush tropical retreat. For the right buyer, the appeal is undeniable: an authentic Old Town home, a highly desirable location, existing income, and the opportunity to restore, reimagine, and create something truly special. Bring your contractor, your creativity, and your vision. This one isn't pretending to be turnkey, but it just might be worth the work. *some photos digitally enhanced only to remove personal belongings

3 Beds ⋅ 2 Baths ⋅ 620987 MLS

Charming Historic Old Town Key West Home, Ready for Its Next Chapter! Here's an opportunity for the buyer who sees possibility where others see a project. This 3-bedroom, 1.5-bath historic Key West home is tucked into the heart of Old Town, just minutes from the Historic Seaport, downtown, restaurants, shopping, and everything that makes island living so special. With classic Key West architecture, a welcoming front porch, hardwood floors, vintage windows, and plenty of original character, the home offers a wonderful starting point for a thoughtful renovation. The interior has been freshly painted, but this is a property that will require renovation and is best suited for a buyer ready to take on a true restoration project. Currently tenant occupied, the property also offers the advantage of existing rental income while a new owner makes plans, lines up contractors, or prepares for a future renovation or move-in. The existing floor plan includes generous living space, three bedrooms, a full bath downstairs, a half bath upstairs, and a private backyard with the potential to become a lush tropical retreat. For the right buyer, the appeal is undeniable: an authentic Old Town home, a highly desirable location, existing income, and the opportunity to restore, reimagine, and create something truly special. Bring your contractor, your creativity, and your vision. This one isn't pretending to be turnkey, but it just might be worth the work. *some photos digitally enhanced only to remove personal belongings

506 Grinnell St, Key West

$3,700,000

Awarded the Florida Keys Preservation Star, this meticulously restored single-family home offers an enchanting blend of historic Key West charm, modern luxury, and high-yield investment potential. Holding a coveted TRANSIENT LICENSE allowing profitable nightly rentals, this turnkey Old Town sanctuary sits just a half-block from world-famous Duval Street while enjoying a prime position near boutique shops, fine dining, and the Southernmost Point. Step inside through iconic yellow doors into a bright, sunny retreat defined by historic Dade County pine walls, gingerbread balustrade details, high soaring ceilings, and rich natural light. The main level flows into an open-concept living area and a sleek white kitchen equipped with stainless steel appliances, ample prep space, and an oversized island with seating for six--perfect for gathering family and friends. Designed for indoor-outdoor living, double sliders spill out to a well-appointed, covered lanai featuring a large outdoor TV and a rare air-conditioned half bath. Beyond the lanai lies a private tropical oasis enveloped by lush palm trees and fencing. Take a refreshing dip in the 8' x 14' heated pool with its soothing water feature, lounge in the sunshine on the deck, or host alfresco dinners using the gas grill. The interior layout offers total comfort and privacy for guests. The main floor houses two king-bedroom suites complete with walk-in showers, including one with direct access to the poolside sanctuary. Tucked upstairs for added seclusion, the third ensuite bedroom features a queen bed, vaulted ceilings, and sunny exposure. Completely renovated with impact windows, and dedicated off-street parking, this property is designed for effortless ownership. Whether retained as a high-performing vacation rental with proven revenue projections or enjoyed as a private island getaway, this home offers a rare chance to own a piece of Key West paradise.

3 Beds ⋅ 4 Baths ⋅ 620985 MLS

Awarded the Florida Keys Preservation Star, this meticulously restored single-family home offers an enchanting blend of historic Key West charm, modern luxury, and high-yield investment potential. Holding a coveted TRANSIENT LICENSE allowing profitable nightly rentals, this turnkey Old Town sanctuary sits just a half-block from world-famous Duval Street while enjoying a prime position near boutique shops, fine dining, and the Southernmost Point. Step inside through iconic yellow doors into a bright, sunny retreat defined by historic Dade County pine walls, gingerbread balustrade details, high soaring ceilings, and rich natural light. The main level flows into an open-concept living area and a sleek white kitchen equipped with stainless steel appliances, ample prep space, and an oversized island with seating for six--perfect for gathering family and friends. Designed for indoor-outdoor living, double sliders spill out to a well-appointed, covered lanai featuring a large outdoor TV and a rare air-conditioned half bath. Beyond the lanai lies a private tropical oasis enveloped by lush palm trees and fencing. Take a refreshing dip in the 8' x 14' heated pool with its soothing water feature, lounge in the sunshine on the deck, or host alfresco dinners using the gas grill. The interior layout offers total comfort and privacy for guests. The main floor houses two king-bedroom suites complete with walk-in showers, including one with direct access to the poolside sanctuary. Tucked upstairs for added seclusion, the third ensuite bedroom features a queen bed, vaulted ceilings, and sunny exposure. Completely renovated with impact windows, and dedicated off-street parking, this property is designed for effortless ownership. Whether retained as a high-performing vacation rental with proven revenue projections or enjoyed as a private island getaway, this home offers a rare chance to own a piece of Key West paradise.

530 Catherine St, Key West

$995,000

Get excited about this mid-town oasis. Behind the fence is a charming three-bedroom three bath residence with beautiful grounds, off-street parking, newer roof, impact glass windows and doors, central and ductless air conditioning, storage shed, and much more. The huge kitchen, dining and living rooms are unique. The third bedroom has a separate entrance with private outdoor space, perfect for roommates or mothter-in-law suite. Come see today and make this beautiful property your new home or entry-level investment in Key West.

3 Beds ⋅ 3 Baths ⋅ 620923 MLS

Get excited about this mid-town oasis. Behind the fence is a charming three-bedroom three bath residence with beautiful grounds, off-street parking, newer roof, impact glass windows and doors, central and ductless air conditioning, storage shed, and much more. The huge kitchen, dining and living rooms are unique. The third bedroom has a separate entrance with private outdoor space, perfect for roommates or mothter-in-law suite. Come see today and make this beautiful property your new home or entry-level investment in Key West.

2309 Patterson Ave, Key West

$1,800,000

Steeped in Key West history and unlike anything else available in Old Town, 511 Tabby Lane presents an opportunity to own one of the island's most extraordinary properties. Hidden away at the end of a charming pedestrian lane with direct access to iconic Duval Street, this remarkably private home offers a level of seclusion and potential that is virtually impossible to replicate. Rich in character and history, the property sits on an exceptionally deep 4,200-square-foot lot, a rarity in Old Town. There is simply no other property currently available that offers this combination of privacy, location, and land. The expansive lot provides endless possibilities, with ample space for a pool, pool house, guest quarters, lush gardens, outdoor entertaining areas, and more while still preserving the home's unique Old Town charm. Completely hidden from view behind a gated entrance, the property feels like a private tropical sanctuary in the heart of Key West. Whether you envision thoughtfully restoring the existing residence or creating a one-of-a-kind island compound, the possibilities are exceptional. The structure is believed to be a non-contributing building with HARC (buyer to verify), offering additional flexibility for future improvements. Adding to its rarity, the property is zoned for Transient License Receivership (buyer to verify), making it an incredibly attractive opportunity for investors, developers, or anyone seeking a truly unique Old Town residence. Properties of this caliber and significance rarely become available. 511 Tabby Lane represents a chance to own a piece of Key West history while creating something that future generations will treasure. This is Old Town at its most authentic--and an opportunity that simply cannot be duplicated.

3 Beds ⋅ 1 Baths ⋅ 620880 MLS

Steeped in Key West history and unlike anything else available in Old Town, 511 Tabby Lane presents an opportunity to own one of the island's most extraordinary properties. Hidden away at the end of a charming pedestrian lane with direct access to iconic Duval Street, this remarkably private home offers a level of seclusion and potential that is virtually impossible to replicate. Rich in character and history, the property sits on an exceptionally deep 4,200-square-foot lot, a rarity in Old Town. There is simply no other property currently available that offers this combination of privacy, location, and land. The expansive lot provides endless possibilities, with ample space for a pool, pool house, guest quarters, lush gardens, outdoor entertaining areas, and more while still preserving the home's unique Old Town charm. Completely hidden from view behind a gated entrance, the property feels like a private tropical sanctuary in the heart of Key West. Whether you envision thoughtfully restoring the existing residence or creating a one-of-a-kind island compound, the possibilities are exceptional. The structure is believed to be a non-contributing building with HARC (buyer to verify), offering additional flexibility for future improvements. Adding to its rarity, the property is zoned for Transient License Receivership (buyer to verify), making it an incredibly attractive opportunity for investors, developers, or anyone seeking a truly unique Old Town residence. Properties of this caliber and significance rarely become available. 511 Tabby Lane represents a chance to own a piece of Key West history while creating something that future generations will treasure. This is Old Town at its most authentic--and an opportunity that simply cannot be duplicated.

511 Tabby Ln, Key West

$2,399,000

Experience the best of waterfront living at 3206 Riviera Drive, a beautifully updated canal-front home offering 60 feet of waterfront, exceptional privacy, and direct access to the Key West boating lifestyle. With no homes across the canal, the property enjoys peaceful water views and a uniquely private setting. Designed for both everyday living and entertaining, the open-concept interior is filled with natural light and seamlessly connects to the outdoors through a wall of impact-rated sliding glass doors. The chef's kitchen features premium cabinetry, a large center island, and a waterfront dining area overlooking the pool and canal. The home offers three spacious bedrooms, including two en-suite bedrooms, three full bathrooms, a dedicated laundry room, two-zone air conditioning, and a whole-home generator. Outside, the tropical backyard is built for enjoying the Keys. Relax by the newly renovated heated pool, entertain from the outdoor kitchen, unwind on the screened patio, or enjoy the convenience of an outdoor bathroom. Shell stone limestone walkways, lush landscaping, covered parking, and a fully gated lot complete this private waterfront retreat. Offering the perfect combination of luxury, comfort, and functionality, 3206 Riviera Drive is move-in ready and seller financing may be available.

3 Beds ⋅ 4 Baths ⋅ 620879 MLS

Experience the best of waterfront living at 3206 Riviera Drive, a beautifully updated canal-front home offering 60 feet of waterfront, exceptional privacy, and direct access to the Key West boating lifestyle. With no homes across the canal, the property enjoys peaceful water views and a uniquely private setting. Designed for both everyday living and entertaining, the open-concept interior is filled with natural light and seamlessly connects to the outdoors through a wall of impact-rated sliding glass doors. The chef's kitchen features premium cabinetry, a large center island, and a waterfront dining area overlooking the pool and canal. The home offers three spacious bedrooms, including two en-suite bedrooms, three full bathrooms, a dedicated laundry room, two-zone air conditioning, and a whole-home generator. Outside, the tropical backyard is built for enjoying the Keys. Relax by the newly renovated heated pool, entertain from the outdoor kitchen, unwind on the screened patio, or enjoy the convenience of an outdoor bathroom. Shell stone limestone walkways, lush landscaping, covered parking, and a fully gated lot complete this private waterfront retreat. Offering the perfect combination of luxury, comfort, and functionality, 3206 Riviera Drive is move-in ready and seller financing may be available.

3206 Riviera Dr, Key West

$849,500

Nestled in the serene Bay Manor neighborhood, this beautiful single-family home seamlessly blends comfort with tropical charm. The home boasts a master suite, complemented by 2 additional well-sized bedrooms and 2 full baths. Enjoy a kitchen featuring sleek granite counter tops. A large pantry/laundry room enhances functionality, while the expansive backyard offers ample space for entertaining and a pool. The rear yard is highlighted by a carport and a large cabana-style building, perfect for gatherings or relaxation. Mature trees, lush greenery, a fruit bearing mango tree and a privacy fence surround the property, providing a private and tranquil setting. Conveniently located in New Town near schools and shopping with off street parking. Just a short drive to Key West's vibrant downtown, offering dining, shopping, and cultural attractions. Nearby parks and waterfront areas provide opportunities for boating, fishing, and enjoying the island's natural beauty. Whether you're seeking a vacation retreat, investment property, or full-time residence, this property presents an ideal opportunity to experience the laid-back Key West. One of the listing realtors is related to the sellers.

3 Beds ⋅ 2 Baths ⋅ 620866 MLS

Nestled in the serene Bay Manor neighborhood, this beautiful single-family home seamlessly blends comfort with tropical charm. The home boasts a master suite, complemented by 2 additional well-sized bedrooms and 2 full baths. Enjoy a kitchen featuring sleek granite counter tops. A large pantry/laundry room enhances functionality, while the expansive backyard offers ample space for entertaining and a pool. The rear yard is highlighted by a carport and a large cabana-style building, perfect for gatherings or relaxation. Mature trees, lush greenery, a fruit bearing mango tree and a privacy fence surround the property, providing a private and tranquil setting. Conveniently located in New Town near schools and shopping with off street parking. Just a short drive to Key West's vibrant downtown, offering dining, shopping, and cultural attractions. Nearby parks and waterfront areas provide opportunities for boating, fishing, and enjoying the island's natural beauty. Whether you're seeking a vacation retreat, investment property, or full-time residence, this property presents an ideal opportunity to experience the laid-back Key West. One of the listing realtors is related to the sellers.

2928 Fogarty Ave, Key West

$2,350,000

Set within the exclusive enclave of The Sanctuary at Key West Golf Club, this rare offering presents two distinct residences united as one extraordinary parcel -- a configuration unlike anything currently available on the Key West market. Verandas and porches wrap the property, framing sweeping views of the lake and the emerald fairways of the 17th hole, while tiled floors flow throughout both residences, blurring the line between the two homes and the tropical air outside. At the heart of it all, a resort-caliber pool measuring an impressive 12 x 30 feet anchors a 1,500 square foot outdoor terrace, where long tables are set for twelve or more, indoors and out, beneath the Key West sky. With 6 bedrooms and 5.5 bathrooms spread across 2,840 square feet, this dual-residence estate is purpose-built for the multigenerational family, offering the rare gift of togetherness paired with independence -- separate structures for separate households, united by a single spectacular pool deck built for gathering. For the discerning second-home buyer or investor, the dual-dwelling design opens the door to flexible living arrangements or income-generating potential, a configuration increasingly coveted in today's Key West market. This is more than a home -- it is a once-in-a-lifetime opportunity to establish a family legacy on one of Key West's most coveted golf course settings. Here, generations will gather beneath the verandas, celebrate over long tables set for twelve, and watch the sun set over the 17th green. This is Key West living, reimagined for the modern family -- and passed down for generations to come.

6 Beds ⋅ 6 Baths ⋅ 620852 MLS

Set within the exclusive enclave of The Sanctuary at Key West Golf Club, this rare offering presents two distinct residences united as one extraordinary parcel -- a configuration unlike anything currently available on the Key West market. Verandas and porches wrap the property, framing sweeping views of the lake and the emerald fairways of the 17th hole, while tiled floors flow throughout both residences, blurring the line between the two homes and the tropical air outside. At the heart of it all, a resort-caliber pool measuring an impressive 12 x 30 feet anchors a 1,500 square foot outdoor terrace, where long tables are set for twelve or more, indoors and out, beneath the Key West sky. With 6 bedrooms and 5.5 bathrooms spread across 2,840 square feet, this dual-residence estate is purpose-built for the multigenerational family, offering the rare gift of togetherness paired with independence -- separate structures for separate households, united by a single spectacular pool deck built for gathering. For the discerning second-home buyer or investor, the dual-dwelling design opens the door to flexible living arrangements or income-generating potential, a configuration increasingly coveted in today's Key West market. This is more than a home -- it is a once-in-a-lifetime opportunity to establish a family legacy on one of Key West's most coveted golf course settings. Here, generations will gather beneath the verandas, celebrate over long tables set for twelve, and watch the sun set over the 17th green. This is Key West living, reimagined for the modern family -- and passed down for generations to come.

287 & 289 Golf Club Dr, Key West

$1,400,000

This one is a must see! Spacious FOUR bedroom, single family home in the 'Pearlman Heights' neighborhood of New Town KW that has undergone recent renovations-upgrades. New roof, kitchen (appliances, cabinets, counter tops), windows / doors (impact rated), bathrooms (fixtures, flooring, showers, faucets, vanities), on demand water heater, pool pump, Central AC condenser / air handler, light fixtures, ceiling fans, crown molding, paint & more. Nice set up for enjoying the KW weather or entertaining because the den, kitchen & dining areas flow out thru 16 ft of impact rated, glass sliding doors to the back yard with 32 fl long in ground pool. No interior step downs or tripping hazards. Located on a one-way street with green dividing median on 17th St. Carport covers the off-street parking space plus additional on & off-street parking. Has an exterior 15 X 6 storage / laundry room. Convenient location close to schools, medical offices, grocery stores & shopping, dining, etc..

4 Beds ⋅ 2 Baths ⋅ 620808 MLS

This one is a must see! Spacious FOUR bedroom, single family home in the 'Pearlman Heights' neighborhood of New Town KW that has undergone recent renovations-upgrades. New roof, kitchen (appliances, cabinets, counter tops), windows / doors (impact rated), bathrooms (fixtures, flooring, showers, faucets, vanities), on demand water heater, pool pump, Central AC condenser / air handler, light fixtures, ceiling fans, crown molding, paint & more. Nice set up for enjoying the KW weather or entertaining because the den, kitchen & dining areas flow out thru 16 ft of impact rated, glass sliding doors to the back yard with 32 fl long in ground pool. No interior step downs or tripping hazards. Located on a one-way street with green dividing median on 17th St. Carport covers the off-street parking space plus additional on & off-street parking. Has an exterior 15 X 6 storage / laundry room. Convenient location close to schools, medical offices, grocery stores & shopping, dining, etc..

1105 17th St, Key West

$12,500,000

A distinguished offering on one of Key West's most coveted private island enclaves, 32 Sunset Key Drive embodies the ease, elegance, and exclusivity of waterfront living. One of the largest custom residences on Sunset Key, this 3,635-square-foot oceanfront estate was conceived by its original owners with an unwavering commitment to craftsmanship, comfort, and detail. Set beside its own private beach, the home features six ensuite bedrooms and seven full baths, creating a refined retreat designed for gracious hosting and effortless relaxation. Inside, coffered wood-paneled ceilings, tumbled marble, and solid oak floors lend depth, texture, and timeless coastal sophistication. Expansive living, dining, and kitchen spaces open naturally to the outdoors, blurring the line between interior comfort and the island's spectacular waterfront setting. Beyond, a custom rock pool with a hot tub and two-story slide evokes the atmosphere of a private resort, while a fully equipped outdoor kitchen, full bath, shower, and laundry facility elevate every gathering with ease and intention. Hop on the five minute ferry ride to your island paradise, enjoy the fabulous spa and dine at the acclaimed restaurant Latitudes. Truly, this is a one of a kind opportunity for the discerning buyer.

6 Beds ⋅ 7 Baths ⋅ 620770 MLS

A distinguished offering on one of Key West's most coveted private island enclaves, 32 Sunset Key Drive embodies the ease, elegance, and exclusivity of waterfront living. One of the largest custom residences on Sunset Key, this 3,635-square-foot oceanfront estate was conceived by its original owners with an unwavering commitment to craftsmanship, comfort, and detail. Set beside its own private beach, the home features six ensuite bedrooms and seven full baths, creating a refined retreat designed for gracious hosting and effortless relaxation. Inside, coffered wood-paneled ceilings, tumbled marble, and solid oak floors lend depth, texture, and timeless coastal sophistication. Expansive living, dining, and kitchen spaces open naturally to the outdoors, blurring the line between interior comfort and the island's spectacular waterfront setting. Beyond, a custom rock pool with a hot tub and two-story slide evokes the atmosphere of a private resort, while a fully equipped outdoor kitchen, full bath, shower, and laundry facility elevate every gathering with ease and intention. Hop on the five minute ferry ride to your island paradise, enjoy the fabulous spa and dine at the acclaimed restaurant Latitudes. Truly, this is a one of a kind opportunity for the discerning buyer.

32 Sunset, Key West

$2,980,000

PRICE IMPROVEMENT- Classic Key West charm and sophistication abound, with traditional grace yet modern conveniences, this wasn't just a simple remodel. This was a carefully thought out, complete and careful renovation of this Old Town treasure. This home is carefree, furnished, and turnkey-bring your personal bag and you are home immediately. A worry free and easily maintained 3 bedroom, 2 and & ½ bath home, master bath ensuite, on one of the most prestigious streets in Key West, this home is constantly photographed, whether it's the location, the style, or the carefully chosen color pallet by the current owners, we're not sure, but regardless, many are drawn to this home and its beautifully tailored look. Whether you want to people watch on the front porch and sip your coffee or cocktail, or withdraw to the secluded private back yard and lounge around the pool reading a Hemingway novel, who's legendary home is a mere stroll moments away out the gate one direction, or go the opposite direction to the Atlantic Ocean and the Southernmost Point Buoy, everything Key West is only minutes away from this front door, your front door. Your new home. And by new, that's what we mean-this home was carefully and completely renovated in the last couple years, essentially creating a classic Key West house, with all the comfort and benefits of a new home. A completely custom Bosch appliance filled kitchen, with virtually every modern convenience a new home would hold. Modern upscale interior, zoned central A/C system with whole-house ventilating dehumidifier, advanced internet modem and router system, maintenance free composite decking, complete security and camera system, are just a few of the extra steps the owners took when creating a time-honored but luxurious, self contained and above the norm renovation of this truly one of a kind Key West home. Lets set up your private showing today.

3 Beds ⋅ 3 Baths ⋅ 620747 MLS

PRICE IMPROVEMENT- Classic Key West charm and sophistication abound, with traditional grace yet modern conveniences, this wasn't just a simple remodel. This was a carefully thought out, complete and careful renovation of this Old Town treasure. This home is carefree, furnished, and turnkey-bring your personal bag and you are home immediately. A worry free and easily maintained 3 bedroom, 2 and & ½ bath home, master bath ensuite, on one of the most prestigious streets in Key West, this home is constantly photographed, whether it's the location, the style, or the carefully chosen color pallet by the current owners, we're not sure, but regardless, many are drawn to this home and its beautifully tailored look. Whether you want to people watch on the front porch and sip your coffee or cocktail, or withdraw to the secluded private back yard and lounge around the pool reading a Hemingway novel, who's legendary home is a mere stroll moments away out the gate one direction, or go the opposite direction to the Atlantic Ocean and the Southernmost Point Buoy, everything Key West is only minutes away from this front door, your front door. Your new home. And by new, that's what we mean-this home was carefully and completely renovated in the last couple years, essentially creating a classic Key West house, with all the comfort and benefits of a new home. A completely custom Bosch appliance filled kitchen, with virtually every modern convenience a new home would hold. Modern upscale interior, zoned central A/C system with whole-house ventilating dehumidifier, advanced internet modem and router system, maintenance free composite decking, complete security and camera system, are just a few of the extra steps the owners took when creating a time-honored but luxurious, self contained and above the norm renovation of this truly one of a kind Key West home. Lets set up your private showing today.

1019 Whitehead St, Key West

$1,695,000

Fully furnished, 2b/2b designer-complete home is close to the heart of Old Town Key West, yet far enough from the maddening crowd. Late-1800s Conch house with detached guest cottage were gutted, reconfigured and restored in 2021. New roof, infrastructure and new state-of-the-art chef's kitchen. Casement windows open to the back garden that has 8 varieties of bananas. And what a fine garden it is: Orchids & herbs & fruit, oh my. Salvaged Dade County pine walls light up with windows galore. A side yard connects the 1b/1b primary residence to the en-suite detached cottage. On-demand hot water heater. Outdoor shower. Hot tub. Off-street parking. Rear garden entrance to property from Havana Lane offers front and back access. Meticulous detail throughout makes this A MUST SEE. Low fee insurance costs available upon request.

2 Beds ⋅ 2 Baths ⋅ 620684 MLS

Fully furnished, 2b/2b designer-complete home is close to the heart of Old Town Key West, yet far enough from the maddening crowd. Late-1800s Conch house with detached guest cottage were gutted, reconfigured and restored in 2021. New roof, infrastructure and new state-of-the-art chef's kitchen. Casement windows open to the back garden that has 8 varieties of bananas. And what a fine garden it is: Orchids & herbs & fruit, oh my. Salvaged Dade County pine walls light up with windows galore. A side yard connects the 1b/1b primary residence to the en-suite detached cottage. On-demand hot water heater. Outdoor shower. Hot tub. Off-street parking. Rear garden entrance to property from Havana Lane offers front and back access. Meticulous detail throughout makes this A MUST SEE. Low fee insurance costs available upon request.

907 Frances St, Key West

$4,750,000

TRANSIENT LICENSE TRANSFER RECEIVER ZONE!!!! A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the historic Trumbo Point waterfront, this remarkable estate has remained in the same family for generations and reflects a rich connection to one of the island's most significant maritime neighborhoods. Thought to have origins dating back to the early 20th century, the property showcases timeless Old Key West charm while offering the space and flexibility rarely found today. The main residence is complemented by a separate guest cottage on an oversized waterfront parcel, creating endless possibilities for multigenerational living, a private family compound, or an exceptional investment opportunity. Located in an area once shaped by the island's cigar industry, railroad expansion, and later the development of the Naval Air Station and Coast Guard facilities, this home sits within a neighborhood that tells the story of Key West's evolution through more than a century of history. From the moment you arrive, you'll appreciate the mature tropical landscape, water access, and the feeling of stepping into a piece of Old Key West. Whether you choose to preserve its historic character, thoughtfully enhance the existing structures, or create your own legacy estate, opportunities like this are exceptionally rare. Waterfront properties with this combination of history, location, size, and family ownership seldom become available. 901 Eisenhower Drive is more than a home--it's an opportunity to own a meaningful piece of Key West's past while creating its next chapter.

7 Beds ⋅ 5 Baths ⋅ 620661 MLS

TRANSIENT LICENSE TRANSFER RECEIVER ZONE!!!! A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the historic Trumbo Point waterfront, this remarkable estate has remained in the same family for generations and reflects a rich connection to one of the island's most significant maritime neighborhoods. Thought to have origins dating back to the early 20th century, the property showcases timeless Old Key West charm while offering the space and flexibility rarely found today. The main residence is complemented by a separate guest cottage on an oversized waterfront parcel, creating endless possibilities for multigenerational living, a private family compound, or an exceptional investment opportunity. Located in an area once shaped by the island's cigar industry, railroad expansion, and later the development of the Naval Air Station and Coast Guard facilities, this home sits within a neighborhood that tells the story of Key West's evolution through more than a century of history. From the moment you arrive, you'll appreciate the mature tropical landscape, water access, and the feeling of stepping into a piece of Old Key West. Whether you choose to preserve its historic character, thoughtfully enhance the existing structures, or create your own legacy estate, opportunities like this are exceptionally rare. Waterfront properties with this combination of history, location, size, and family ownership seldom become available. 901 Eisenhower Drive is more than a home--it's an opportunity to own a meaningful piece of Key West's past while creating its next chapter.

901 Eisenhower Dr, Key West

$1,139,000

Tucked into the leafy heart of Midtown, just a quick bike ride from Smathers Beach, Higgs Beach and the energy of downtown, 1708 South St. offers something increasingly rare in Key West: a property with nothing to do but move in and enjoy. With its classic stone facade, this 1952 residence captures the distinctive architectural style that defined post-war Key West, delivering 1,445 sq. ft. of low-maintenance living, ideal for the second-home buyer who wants the Key West lifestyle without the upkeep of a larger historic home. Tile floors run throughout, complementing a solid wood kitchen that retains its excellent-condition granite countertops. A versatile Florida room to the rear opens through French doors to the back garden, equally suited as a formal dining room, a home office, or a playroom. Beyond, the backyard is a blank canvas, ready to become a stunning tropical Key West oasis complete with an outdoor entertaining area. The detached guest cottage, with its own private entrance, adds a third bedroom to the property and is currently leased to a long-term tenant (Lease expires Sept 30th 2026) at a meaningful monthly rent, offering established income with true separation of space, a compelling proposition for the second-homeowner who wants their property earning for them even when they're not there to enjoy it. A covered carport for two vehicles and abundant storage round out the property's everyday practicality. Offered at a clear value against comparable Midtown properties, this is an entry point into island living that is as flexible as it is rare. Welcome to Key West Living at its finest.

3 Beds ⋅ 2 Baths ⋅ 620641 MLS

Tucked into the leafy heart of Midtown, just a quick bike ride from Smathers Beach, Higgs Beach and the energy of downtown, 1708 South St. offers something increasingly rare in Key West: a property with nothing to do but move in and enjoy. With its classic stone facade, this 1952 residence captures the distinctive architectural style that defined post-war Key West, delivering 1,445 sq. ft. of low-maintenance living, ideal for the second-home buyer who wants the Key West lifestyle without the upkeep of a larger historic home. Tile floors run throughout, complementing a solid wood kitchen that retains its excellent-condition granite countertops. A versatile Florida room to the rear opens through French doors to the back garden, equally suited as a formal dining room, a home office, or a playroom. Beyond, the backyard is a blank canvas, ready to become a stunning tropical Key West oasis complete with an outdoor entertaining area. The detached guest cottage, with its own private entrance, adds a third bedroom to the property and is currently leased to a long-term tenant (Lease expires Sept 30th 2026) at a meaningful monthly rent, offering established income with true separation of space, a compelling proposition for the second-homeowner who wants their property earning for them even when they're not there to enjoy it. A covered carport for two vehicles and abundant storage round out the property's everyday practicality. Offered at a clear value against comparable Midtown properties, this is an entry point into island living that is as flexible as it is rare. Welcome to Key West Living at its finest.

1708 South Street, Key West

$1,095,000

THIS IS THE PLAY. Big lot. Big upside. Atlantic Boulevard address. 1503 Atlantic Boulevard brings together the pieces that matter most in Key West: land, location, pool, and multi-unit flexibility. Atlantic Boulevard has only a handful of true residential opportunities, and this one brings the rare combination of land, pool, and multi-unit upside. Set on an approximately 8,050 square foot lot, this Atlantic-side property offers roughly 2,750 square feet of living area with a flexible multi-unit configuration and a concrete pool anchoring the outdoor space. The existing home would benefit from a major renovation and thoughtful updating for today's standards, creating a compelling opportunity for an investor, owner-user, or buyer with vision. In a market where land is the luxury, the lot itself is a major part of the story. The scale, pool, and layout create the foundation for a refreshed tropical compound, income-producing retreat, or reimagined Key West residence. Located along Atlantic Boulevard, the property is close to beaches, Old Town, Casa Marina, schools, dining, and the everyday ease that makes island living so desirable. Whether held as a long-term income property or transformed into something more polished, 1503 Atlantic Boulevard offers the kind of upside that is increasingly hard to find in Key West.

4 Beds ⋅ 5 Baths ⋅ 620612 MLS

THIS IS THE PLAY. Big lot. Big upside. Atlantic Boulevard address. 1503 Atlantic Boulevard brings together the pieces that matter most in Key West: land, location, pool, and multi-unit flexibility. Atlantic Boulevard has only a handful of true residential opportunities, and this one brings the rare combination of land, pool, and multi-unit upside. Set on an approximately 8,050 square foot lot, this Atlantic-side property offers roughly 2,750 square feet of living area with a flexible multi-unit configuration and a concrete pool anchoring the outdoor space. The existing home would benefit from a major renovation and thoughtful updating for today's standards, creating a compelling opportunity for an investor, owner-user, or buyer with vision. In a market where land is the luxury, the lot itself is a major part of the story. The scale, pool, and layout create the foundation for a refreshed tropical compound, income-producing retreat, or reimagined Key West residence. Located along Atlantic Boulevard, the property is close to beaches, Old Town, Casa Marina, schools, dining, and the everyday ease that makes island living so desirable. Whether held as a long-term income property or transformed into something more polished, 1503 Atlantic Boulevard offers the kind of upside that is increasingly hard to find in Key West.

1503 Atlantic Blvd, Key West

$849,000

Adorable 2 bed ,1.5 bath single family home in Pearlman neighborhood with separate 1-1 cottage anchored by a picturesque Royal Poinciana tree out front! Features a large (16 X 15) screen room between the main house & the cottage. You can pass from the main house thru the screened room into the cottage & still be under roof. Cottage does have its own separate entrance. Use the cottage as an extension of the main house or as separate living space, she-shed, man-cave, studio, work out room or home office. Roof replaced in 2016. Exposed beam ceilings in kitchen and dining areas. For those familiar with the 'Sunshine Homes' in KW, you know they were built with crawl spaces between the ground & the floor, taller attics w/ pull-down stairs, beautiful hard wood floors & asbestos siding. Most of main house still has original hard wood floors & the cottage has bamboo flooring. Sellers say interior of house did not flood during Wilma. 3712 Duck affords you yard space, room for pool, carport with additional off-street parking & one of KW's most desirable New Town neighborhoods. Convenient location is close to schools, shopping, theaters, medical offices, ball fields, beach, airport, golf course & hospital. Just a short ride into Old Town & world-famous Duval St.. Make your next home at 3712 Duck Ave!

3 Beds ⋅ 3 Baths ⋅ 620501 MLS

Adorable 2 bed ,1.5 bath single family home in Pearlman neighborhood with separate 1-1 cottage anchored by a picturesque Royal Poinciana tree out front! Features a large (16 X 15) screen room between the main house & the cottage. You can pass from the main house thru the screened room into the cottage & still be under roof. Cottage does have its own separate entrance. Use the cottage as an extension of the main house or as separate living space, she-shed, man-cave, studio, work out room or home office. Roof replaced in 2016. Exposed beam ceilings in kitchen and dining areas. For those familiar with the 'Sunshine Homes' in KW, you know they were built with crawl spaces between the ground & the floor, taller attics w/ pull-down stairs, beautiful hard wood floors & asbestos siding. Most of main house still has original hard wood floors & the cottage has bamboo flooring. Sellers say interior of house did not flood during Wilma. 3712 Duck affords you yard space, room for pool, carport with additional off-street parking & one of KW's most desirable New Town neighborhoods. Convenient location is close to schools, shopping, theaters, medical offices, ball fields, beach, airport, golf course & hospital. Just a short ride into Old Town & world-famous Duval St.. Make your next home at 3712 Duck Ave!

3712 Duck Ave, Key West

$1,825,000

RARE OPPORTUNITY TO PURCHASE IN CASA MARINA FOR ONLY $835 PRICE PER SQUARE FOOT. (34% BELOW market value) Life feels a little different in Casa Marina. The streets are quieter, the homes are beautifully maintained, and everything from the beach to Old Town is just a short walk or bike ride away. Tucked within one of Key West's most desirable neighborhoods, 1115 South Street captures everything people love about living here. Step inside and the home immediately feels open and inviting. Ten foot ceilings, warm Brazilian cherry floors, and an abundance of natural light create spaces that feel both elegant and comfortable. The entire first floor is designed for gathering, anchored by an impressive kitchen with abundant cabinetry, expansive countertops, and high end appliances that make cooking and entertaining equally enjoyable. As beautiful as the interior is, your attention naturally shifts outdoors. French doors open to a private tropical backyard where a large swimming pool, separate hot tub, and coral stone patios with IPE decking create a peaceful setting for relaxing or entertaining. Surrounded by mature landscaping, the backyard feels like your own private retreat. With both bedrooms located upstairs, the home offers a thoughtful separation between everyday living and personal space. The primary suite even enjoys its own balcony overlooking the backyard, providing a quiet place to begin or end the day. Beautifully maintained and thoughtfully designed, this is a home where every detail encourages you to slow down, entertain often, and enjoy the best of Key West living.

2 Beds ⋅ 2 Baths ⋅ 620470 MLS

RARE OPPORTUNITY TO PURCHASE IN CASA MARINA FOR ONLY $835 PRICE PER SQUARE FOOT. (34% BELOW market value) Life feels a little different in Casa Marina. The streets are quieter, the homes are beautifully maintained, and everything from the beach to Old Town is just a short walk or bike ride away. Tucked within one of Key West's most desirable neighborhoods, 1115 South Street captures everything people love about living here. Step inside and the home immediately feels open and inviting. Ten foot ceilings, warm Brazilian cherry floors, and an abundance of natural light create spaces that feel both elegant and comfortable. The entire first floor is designed for gathering, anchored by an impressive kitchen with abundant cabinetry, expansive countertops, and high end appliances that make cooking and entertaining equally enjoyable. As beautiful as the interior is, your attention naturally shifts outdoors. French doors open to a private tropical backyard where a large swimming pool, separate hot tub, and coral stone patios with IPE decking create a peaceful setting for relaxing or entertaining. Surrounded by mature landscaping, the backyard feels like your own private retreat. With both bedrooms located upstairs, the home offers a thoughtful separation between everyday living and personal space. The primary suite even enjoys its own balcony overlooking the backyard, providing a quiet place to begin or end the day. Beautifully maintained and thoughtfully designed, this is a home where every detail encourages you to slow down, entertain often, and enjoy the best of Key West living.

1115 South Street, Key West

$979,000

When value matters, this solid concrete New Town home stands apart with one of the most compelling price-per-square-foot opportunities on the market. Substantial 4-bedroom, 2-bath home featuring a dedicated office, offering an exceptional combination of comfort and functionality. Situated on an expansive 8,448-square-foot corner lot, the property provides 2,111 square feet of living space, two driveways, off-street parking with an attached carport, a Tesla charging station, and ample room to add a pool. Designed for easy living and entertaining, the open-concept kitchen and living area is enhanced by soaring cathedral ceilings with exposed beams and an abundance of large, light-filtering windows that create a bright and inviting atmosphere throughout. A welcoming front porch, set back amongst mature trees, provides the perfect place to relax and unwind. The elevated home features double-pane windows, noise-dampening door improvements, a V-crimp metal roof, and beautiful terrazzo floors that add timeless Key West character. The solid concrete construction offers lasting durability and an excellent foundation to fine-tune and personalize the home to suit your vision. The fully walled property provides privacy and generous outdoor space. With its larger-than-average footprint, oversized corner lot, two driveways, and endless potential for a backyard pool oasis, this home presents an outstanding opportunity to enjoy the very best of Key West living. Whether you're searching for a comfortably sized family home just or a property with the perfect canvas to create your dream home, this opportunity offers exceptional value.

4 Beds ⋅ 2 Baths ⋅ 620453 MLS

When value matters, this solid concrete New Town home stands apart with one of the most compelling price-per-square-foot opportunities on the market. Substantial 4-bedroom, 2-bath home featuring a dedicated office, offering an exceptional combination of comfort and functionality. Situated on an expansive 8,448-square-foot corner lot, the property provides 2,111 square feet of living space, two driveways, off-street parking with an attached carport, a Tesla charging station, and ample room to add a pool. Designed for easy living and entertaining, the open-concept kitchen and living area is enhanced by soaring cathedral ceilings with exposed beams and an abundance of large, light-filtering windows that create a bright and inviting atmosphere throughout. A welcoming front porch, set back amongst mature trees, provides the perfect place to relax and unwind. The elevated home features double-pane windows, noise-dampening door improvements, a V-crimp metal roof, and beautiful terrazzo floors that add timeless Key West character. The solid concrete construction offers lasting durability and an excellent foundation to fine-tune and personalize the home to suit your vision. The fully walled property provides privacy and generous outdoor space. With its larger-than-average footprint, oversized corner lot, two driveways, and endless potential for a backyard pool oasis, this home presents an outstanding opportunity to enjoy the very best of Key West living. Whether you're searching for a comfortably sized family home just or a property with the perfect canvas to create your dream home, this opportunity offers exceptional value.

1500 5th St, Key West

$1,385,000

There is almost nothing like this in Key West: a 2007-built home, raised from the ground up to modern standards. Rare, move-in ready, and free of the surprises that come with much older homes in town. Elevated above the floodplain, with impact windows and doors rated for 175 mph winds and a 16kW standby generator, this is a home built for real peace of mind, whether you are here year-round or away for the summer. Inside, vaulted ceilings soar over travertine floors, granite counters, and stainless steel appliances, including a gas range, set off by warm custom cabinetry. The primary bedroom has a roomy walk-in closet and a spa-style stone shower. Then there is the outside, private, and tropical. Picture morning coffee by the saltwater pool and easy evenings under the covered gazebo, eight around the table with plenty of room for the grilling enthusiast. A wide composite deck and an outdoor shower to rinse off after a swim round out the space. Three bedrooms, two baths, and storage you will actually use: a floored, air-conditioned attic plus generous space under the house. A covered double driveway adds to the everyday convenience. This is the Key West home you have been waiting for.

3 Beds ⋅ 2 Baths ⋅ 620448 MLS

There is almost nothing like this in Key West: a 2007-built home, raised from the ground up to modern standards. Rare, move-in ready, and free of the surprises that come with much older homes in town. Elevated above the floodplain, with impact windows and doors rated for 175 mph winds and a 16kW standby generator, this is a home built for real peace of mind, whether you are here year-round or away for the summer. Inside, vaulted ceilings soar over travertine floors, granite counters, and stainless steel appliances, including a gas range, set off by warm custom cabinetry. The primary bedroom has a roomy walk-in closet and a spa-style stone shower. Then there is the outside, private, and tropical. Picture morning coffee by the saltwater pool and easy evenings under the covered gazebo, eight around the table with plenty of room for the grilling enthusiast. A wide composite deck and an outdoor shower to rinse off after a swim round out the space. Three bedrooms, two baths, and storage you will actually use: a floored, air-conditioned attic plus generous space under the house. A covered double driveway adds to the everyday convenience. This is the Key West home you have been waiting for.

2313 Fogarty Ave, Key West

$749,000

Charming Key West Cottage with large back yard and ROOM FOR A BIG POOL! Pack your flip flops and leave your worries at the door! This enchanting Key West gem is ready to make your island dreams a reality! Nestled in the heart of the Conch Republic, 2005 Fogarty Avenue is the kind of home that makes you exhale the moment you arrive. This beautifully updated 2 bedroom home has a bonus room for 3rd bedroom with own private full bath. The home is bursting with Key West charm and curb appeal! From the moment you step inside, you'll fall in love with the character and that unmistakable colorful warmth that only Key West living can deliver. Best of all? It's fully furnished and completely move-in ready. Just bring your toothbrush and your sunscreen, because everything else is already waiting for you.The versatile bonus space offers endless possibilities! Want a home office, guest overflow, art studio, workshop, or your very own private retreat? Step outside and discover the real showstopper: a spacious, lushly landscaped backyard that's practically begging for a sparkling pool 🏊. Whether you envision weekend soirées under the stars, a private tropical oasis, or the ultimate vacation rental income producer, this backyard delivers the canvas. Practical perks? You've got those too. Off-street parking is a rare and treasured luxury in Key West and this property has it. No more circling the block after a long day at the beach. Located just moments from world-famous Duval Street, celebrated dining, vibrant nightlife, the Historic Seaport, and those legendary Key West sunsets 🌅, this property places you at the very center of the island lifestyle while offering a peaceful, private retreat to come home to.✨ Furnished & Move-In Ready, updated, Expansive Backyard with Pool Potential, Off-Street Parking, central Key West Location. If you are searching for a full-time residence, a vacation escape, or a high-demand rental investment, 2005 Fogarty Ave checks

3 Beds ⋅ 2 Baths ⋅ 620436 MLS

Charming Key West Cottage with large back yard and ROOM FOR A BIG POOL! Pack your flip flops and leave your worries at the door! This enchanting Key West gem is ready to make your island dreams a reality! Nestled in the heart of the Conch Republic, 2005 Fogarty Avenue is the kind of home that makes you exhale the moment you arrive. This beautifully updated 2 bedroom home has a bonus room for 3rd bedroom with own private full bath. The home is bursting with Key West charm and curb appeal! From the moment you step inside, you'll fall in love with the character and that unmistakable colorful warmth that only Key West living can deliver. Best of all? It's fully furnished and completely move-in ready. Just bring your toothbrush and your sunscreen, because everything else is already waiting for you.The versatile bonus space offers endless possibilities! Want a home office, guest overflow, art studio, workshop, or your very own private retreat? Step outside and discover the real showstopper: a spacious, lushly landscaped backyard that's practically begging for a sparkling pool 🏊. Whether you envision weekend soirées under the stars, a private tropical oasis, or the ultimate vacation rental income producer, this backyard delivers the canvas. Practical perks? You've got those too. Off-street parking is a rare and treasured luxury in Key West and this property has it. No more circling the block after a long day at the beach. Located just moments from world-famous Duval Street, celebrated dining, vibrant nightlife, the Historic Seaport, and those legendary Key West sunsets 🌅, this property places you at the very center of the island lifestyle while offering a peaceful, private retreat to come home to.✨ Furnished & Move-In Ready, updated, Expansive Backyard with Pool Potential, Off-Street Parking, central Key West Location. If you are searching for a full-time residence, a vacation escape, or a high-demand rental investment, 2005 Fogarty Ave checks

2005 Fogarty Ave, Key West

$889,000

Welcome to 2317 Fogarty Avenue, a beautifully updated 3-bedroom, 2-bathroom home ideally located in the heart of Key West. Combining modern upgrades with island charm, this centrally located residence offers comfortable living just minutes from beaches, shopping, dining, schools, and all that Key West has to offer. The updated kitchen features elegant porcelain countertops, Café appliances, and a newly installed range hood. Recent improvements include a new metal roof (2025) and A/C coils replaced in 2026, providing added peace of mind. An added bonus is the spacious attic, offering valuable storage space--a rare and highly desirable feature in Key West. Step outside to a spacious backyard with mature banana trees, plenty of room to add a pool, and space to create your own private island oasis. A double driveway provides ample off-street parking. Whether you're searching for a full-time residence, a second home, or an investment opportunity, this move-in-ready property offers the perfect blend of comfort, convenience, and island living. Owner is a licensed Florida real estate agent.

3 Beds ⋅ 2 Baths ⋅ 620435 MLS

Welcome to 2317 Fogarty Avenue, a beautifully updated 3-bedroom, 2-bathroom home ideally located in the heart of Key West. Combining modern upgrades with island charm, this centrally located residence offers comfortable living just minutes from beaches, shopping, dining, schools, and all that Key West has to offer. The updated kitchen features elegant porcelain countertops, Café appliances, and a newly installed range hood. Recent improvements include a new metal roof (2025) and A/C coils replaced in 2026, providing added peace of mind. An added bonus is the spacious attic, offering valuable storage space--a rare and highly desirable feature in Key West. Step outside to a spacious backyard with mature banana trees, plenty of room to add a pool, and space to create your own private island oasis. A double driveway provides ample off-street parking. Whether you're searching for a full-time residence, a second home, or an investment opportunity, this move-in-ready property offers the perfect blend of comfort, convenience, and island living. Owner is a licensed Florida real estate agent.

2317 Fogarty Ave, Key West

$3,500,000

First Time on the Market in 26 Years! Just 79 steps from Duval Street, this extraordinary Historic Victorian estate presents a rare opportunity to own one of Key West's most iconic and meticulously maintained properties. Featuring 6+ Off-Street Parking Spaces, 5 bedrooms and 5 bathrooms, this stunning residence embodies the Key West lifestyle with expansive wraparound porches,timeless architectural details, and an unbeatable Old Town location.Originally renovated in 2001 and thoughtfully updated through 2025, the property blends historic character with modern functionality.. Situated on a generous 6,700-square-foot lot, the property offers parking for up to nine vehicles--an exceptional amenity in Old Town Key West--with ample space remaining for the addition of a private pool. Enjoy picturesque views of the surrounding historic district from the expansive porches while embracing the relaxed island atmosphere that defines Key West living. A unique and valuable feature of the property is its 15,000-gallon underground rainwater harvesting cistern, measuring approximately 11' x 13' x 19'. Designed and constructed by a retired Boeing piping engineer, the system incorporates a dual-chamber design, allowing one chamber to remain in service while the other is isolated for inspection, cleaning, and maintenance. The home's roof drainage system has been professionally plumbed to collect and direct rainwater into the cistern, with a diverter valve that allows water to be routed either into storage or discharged into the yard. With the addition of a pump, this impressive system can be reactivated for irrigation and other sustainable water-management uses.Offering historic significance, income potential, abundant parking, modern updates, and a truly rare engineering feature, this exceptional property is a one-of-a-kind opportunity in the heart of Old Town.Corner Lane Lot: dimensions 50' x 134 Bike Rack Stays!

5 Beds ⋅ 5 Baths ⋅ 620434 MLS

First Time on the Market in 26 Years! Just 79 steps from Duval Street, this extraordinary Historic Victorian estate presents a rare opportunity to own one of Key West's most iconic and meticulously maintained properties. Featuring 6+ Off-Street Parking Spaces, 5 bedrooms and 5 bathrooms, this stunning residence embodies the Key West lifestyle with expansive wraparound porches,timeless architectural details, and an unbeatable Old Town location.Originally renovated in 2001 and thoughtfully updated through 2025, the property blends historic character with modern functionality.. Situated on a generous 6,700-square-foot lot, the property offers parking for up to nine vehicles--an exceptional amenity in Old Town Key West--with ample space remaining for the addition of a private pool. Enjoy picturesque views of the surrounding historic district from the expansive porches while embracing the relaxed island atmosphere that defines Key West living. A unique and valuable feature of the property is its 15,000-gallon underground rainwater harvesting cistern, measuring approximately 11' x 13' x 19'. Designed and constructed by a retired Boeing piping engineer, the system incorporates a dual-chamber design, allowing one chamber to remain in service while the other is isolated for inspection, cleaning, and maintenance. The home's roof drainage system has been professionally plumbed to collect and direct rainwater into the cistern, with a diverter valve that allows water to be routed either into storage or discharged into the yard. With the addition of a pump, this impressive system can be reactivated for irrigation and other sustainable water-management uses.Offering historic significance, income potential, abundant parking, modern updates, and a truly rare engineering feature, this exceptional property is a one-of-a-kind opportunity in the heart of Old Town.Corner Lane Lot: dimensions 50' x 134 Bike Rack Stays!

416 Fleming St, Key West