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1119 Simonton St Unit A1 & A2 & C1, Key West

Charming Old Town Duplex located in the heart of old town. Ideally located on Simonton Street this charming duplex places you just steps from Duval Street, along with world-class dining, boutique shopping, beaches, and neighborhood parks. This versatile property is the perfect Key West residence, second home, or income-producing investment. Live in one side and rent the other, or maximize its potential as a full rental property. The home welcomes you with a classic front porch and a private, fenced courtyard surrounded by tropical landscaping--complete with a relaxing hot tub, ideal for enjoying the Key West lifestyle. Inside, the property features updated kitchens, ductless A/C units, and an in-unit washer and dryer. Additional highlights include off-street parking and X Flood Zone. An additional lot (C-1) is included in the sale, featuring a converted storage for added flexibility. Whether you're looking for an island retreat or an investment opportunity in one of Key West's most desirable locations, this Simonton Street property captures the essence of Old Town living. Also available to be purchased separately as two half duplexes. See MLS #619050 and #619052

2 Beds ⋅ 2 Baths ⋅ 619049 MLS

Charming Old Town Duplex located in the heart of old town. Ideally located on Simonton Street this charming duplex places you just steps from Duval Street, along with world-class dining, boutique shopping, beaches, and neighborhood parks. This versatile property is the perfect Key West residence, second home, or income-producing investment. Live in one side and rent the other, or maximize its potential as a full rental property. The home welcomes you with a classic front porch and a private, fenced courtyard surrounded by tropical landscaping--complete with a relaxing hot tub, ideal for enjoying the Key West lifestyle. Inside, the property features updated kitchens, ductless A/C units, and an in-unit washer and dryer. Additional highlights include off-street parking and X Flood Zone. An additional lot (C-1) is included in the sale, featuring a converted storage for added flexibility. Whether you're looking for an island retreat or an investment opportunity in one of Key West's most desirable locations, this Simonton Street property captures the essence of Old Town living. Also available to be purchased separately as two half duplexes. See MLS #619050 and #619052

1119 Simonton St Unit A1 & A2 & C1, Key West

$1,385,000

Centrally located to everything Key West has to offer, and tucked behind a concrete privacy wall on a lush, tropical corner lot, this Midtown Key West property makes a statement the moment you step through the gate. A private courtyard filled with vibrant flowers and mature landscaping immediately sets the tone, leading you to a spacious home full of character and personality! Built with a metal roof, hurricane impact windows and doors, and thoughtfully updated throughout. The functional layout prides itself on easy indoor-outdoor living, effortlessly flowing from the living areas and out to the pool, patios, and guest cottage. The kitchen and dining area are truly made for entertaining, mimicking a chef's kitchen offering generous counter space, ample storage, a bar setup, and abundant natural light pouring in. Step outside to a sunny patio and resort-style pool, perfect for lounging or hosting. Alongside, you'll find a separate guest cottage offering a perfect multi-purpose space. Each bedroom features its own en suite bath, including a spacious primary suite with a walk-in closet, custom built-ins, and your very own private treetop balcony. Additional guest suites are thoughtfully positioned on both levels, including one with its own private entrance. Rich details set this home apart, including Dade County Pine accent walls, stone flooring and bathrooms, multiple balconies, patios, and an outdoor shower. Can be offered turnkey and fully furnished. Additional upgrades include new central AC, high-quality custom awnings, shade sails, a heavy duty storage shed, irrigation system, gutters, and new kitchen appliances.

3 Beds ⋅ 4 Baths ⋅ 619730 MLS

Centrally located to everything Key West has to offer, and tucked behind a concrete privacy wall on a lush, tropical corner lot, this Midtown Key West property makes a statement the moment you step through the gate. A private courtyard filled with vibrant flowers and mature landscaping immediately sets the tone, leading you to a spacious home full of character and personality! Built with a metal roof, hurricane impact windows and doors, and thoughtfully updated throughout. The functional layout prides itself on easy indoor-outdoor living, effortlessly flowing from the living areas and out to the pool, patios, and guest cottage. The kitchen and dining area are truly made for entertaining, mimicking a chef's kitchen offering generous counter space, ample storage, a bar setup, and abundant natural light pouring in. Step outside to a sunny patio and resort-style pool, perfect for lounging or hosting. Alongside, you'll find a separate guest cottage offering a perfect multi-purpose space. Each bedroom features its own en suite bath, including a spacious primary suite with a walk-in closet, custom built-ins, and your very own private treetop balcony. Additional guest suites are thoughtfully positioned on both levels, including one with its own private entrance. Rich details set this home apart, including Dade County Pine accent walls, stone flooring and bathrooms, multiple balconies, patios, and an outdoor shower. Can be offered turnkey and fully furnished. Additional upgrades include new central AC, high-quality custom awnings, shade sails, a heavy duty storage shed, irrigation system, gutters, and new kitchen appliances.

1230 5th St, Key West

$1,380,000

Enjoy the perfect Key West location - Old Town bordering the Casa Marina neighborhood - in this 3 bedroom, 2.5 bath pool home. You'll have peace of mind knowing that the home was completely renovated from the ground up in 2019 while keeping with the historic style of the home's origins - tongue in groove ceilings, wood floors, pecky Cypress wall accent - but adding modern amenities such as impact windows, stainless steel appliances, granite countertops, tankless water heater, in-home laundry. The Main Home has an en suite Primary Bedroom; Guest Bath accessible from the hallway and Guest Bedroom; open concept Kitchen and Family Room with vaulted ceiling and a wall of sliding glass panels overlooking the pool courtyard. Opposite the pool is the Guest Cabana with Half Bath and Outdoor Shower. The property has been offered as a vacation rental and also kept part time for the owner's use. Close to everything you could want in Key West - around the corner from world famous El Siboney Cuban Restaurant, 2 blocks from Truman, 4 blocks from Duval St., a quick walk to Higgs Beach and the White Street Pier. Home is being offered turnkey furnished. Located in Flood Zone X so no flood insurance required.

3 Beds ⋅ 3 Baths ⋅ 619721 MLS

Enjoy the perfect Key West location - Old Town bordering the Casa Marina neighborhood - in this 3 bedroom, 2.5 bath pool home. You'll have peace of mind knowing that the home was completely renovated from the ground up in 2019 while keeping with the historic style of the home's origins - tongue in groove ceilings, wood floors, pecky Cypress wall accent - but adding modern amenities such as impact windows, stainless steel appliances, granite countertops, tankless water heater, in-home laundry. The Main Home has an en suite Primary Bedroom; Guest Bath accessible from the hallway and Guest Bedroom; open concept Kitchen and Family Room with vaulted ceiling and a wall of sliding glass panels overlooking the pool courtyard. Opposite the pool is the Guest Cabana with Half Bath and Outdoor Shower. The property has been offered as a vacation rental and also kept part time for the owner's use. Close to everything you could want in Key West - around the corner from world famous El Siboney Cuban Restaurant, 2 blocks from Truman, 4 blocks from Duval St., a quick walk to Higgs Beach and the White Street Pier. Home is being offered turnkey furnished. Located in Flood Zone X so no flood insurance required.

1215 Margaret St, Key West

$1,350,000

Discover an exceptional opportunity at the Key West Urgent Care location, situated at 1501 Government Rd, Key West. This strategically positioned building is not just a healthcare facility; it represents a cornerstone of community health services in a vibrant, bustling area. **Property Highlights:** - **Prime Location**: Nestled in a high-traffic area, this property benefits from excellent visibility and accessibility, attracting both local residents and tourists alike. - **Versatile Building**: The structure is designed to accommodate urgent care services, featuring multiple examination rooms, administrative offices, and patient waiting areas. Its layout allows for easy modification to suit various medical or commercial uses. - **Expansive Land**: The property sits on a generous plot which may provide space for expansion or additional facilities. This flexibility opens the door for a range of future developments, whether for healthcare or other commercial ventures. - **Community Focus**: As a well-established urgent care center, it has built a strong reputation within the Key West community, offering essential healthcare services and fostering loyalty among patients. - **Growth Potential**: The increasing demand for healthcare services in the area presents significant growth opportunities. Investing in this property means tapping into a vital market with a promising outlook. - **Scenic Surroundings**: Key West is renowned for its stunning landscapes and rich culture, making this location not only functional but also appealing to those who appreciate the unique charm of island life. This is more than just real estate; it's an investment in the health and well-being of the community. Whether you're looking to continue the legacy of urgent care or explore new ventures, 1501 Government Rd is a prime choice of a building for your next project.

618614 MLS

Discover an exceptional opportunity at the Key West Urgent Care location, situated at 1501 Government Rd, Key West. This strategically positioned building is not just a healthcare facility; it represents a cornerstone of community health services in a vibrant, bustling area. **Property Highlights:** - **Prime Location**: Nestled in a high-traffic area, this property benefits from excellent visibility and accessibility, attracting both local residents and tourists alike. - **Versatile Building**: The structure is designed to accommodate urgent care services, featuring multiple examination rooms, administrative offices, and patient waiting areas. Its layout allows for easy modification to suit various medical or commercial uses. - **Expansive Land**: The property sits on a generous plot which may provide space for expansion or additional facilities. This flexibility opens the door for a range of future developments, whether for healthcare or other commercial ventures. - **Community Focus**: As a well-established urgent care center, it has built a strong reputation within the Key West community, offering essential healthcare services and fostering loyalty among patients. - **Growth Potential**: The increasing demand for healthcare services in the area presents significant growth opportunities. Investing in this property means tapping into a vital market with a promising outlook. - **Scenic Surroundings**: Key West is renowned for its stunning landscapes and rich culture, making this location not only functional but also appealing to those who appreciate the unique charm of island life. This is more than just real estate; it's an investment in the health and well-being of the community. Whether you're looking to continue the legacy of urgent care or explore new ventures, 1501 Government Rd is a prime choice of a building for your next project.

1501 Government Road, Key West

$1,345,000

This beautifully updated Foundry townhome in the exclusive gated Truman Annex community is a dream come true! The floor to ceiling windows and doors at the entry allow sunshine to filter into the main floor living space creating a bright and airy space. The main floor has 11 foot ceilings and double French doors that open to the private front courtyard and porch. The open floor plan allows for an easy flow from living space to dining room to kitchen. The stainless steel appliances include a microwave and dishwasher that were installed new in 2024 and barely used. The half bath is located on the first floor for convenience. Make your way up the stairs to the primary suite, located on the second floor, with an en suite bath and walk in shower. Enjoy morning coffee on your private balcony. The washer and dryer are located on this floor and were installed new in 2024. The floor to ceiling French doors and windows allows light to encompass the space. The guest suite is located on the third floor with an en suite bath and shower tub combo. The wall to wall windows allow natural light to flood the room. This home has a designated off street parking spot for 1 vehicle located just out front of the private courtyard. The Foundry swimming pool is a short walk away. This townhome is just down the block from Truman's Little White House, and is an easy walk or bicycle ride to Ft. Zachary Taylor Park, The Coffee Butler Amphitheater and the Truman Waterfront, as well as the world famous Mallory Square and Duval St. Home has been mostly owner occupied but is turnkey for a luxury vacation rental.

2 Beds ⋅ 3 Baths ⋅ 615636 MLS

This beautifully updated Foundry townhome in the exclusive gated Truman Annex community is a dream come true! The floor to ceiling windows and doors at the entry allow sunshine to filter into the main floor living space creating a bright and airy space. The main floor has 11 foot ceilings and double French doors that open to the private front courtyard and porch. The open floor plan allows for an easy flow from living space to dining room to kitchen. The stainless steel appliances include a microwave and dishwasher that were installed new in 2024 and barely used. The half bath is located on the first floor for convenience. Make your way up the stairs to the primary suite, located on the second floor, with an en suite bath and walk in shower. Enjoy morning coffee on your private balcony. The washer and dryer are located on this floor and were installed new in 2024. The floor to ceiling French doors and windows allows light to encompass the space. The guest suite is located on the third floor with an en suite bath and shower tub combo. The wall to wall windows allow natural light to flood the room. This home has a designated off street parking spot for 1 vehicle located just out front of the private courtyard. The Foundry swimming pool is a short walk away. This townhome is just down the block from Truman's Little White House, and is an easy walk or bicycle ride to Ft. Zachary Taylor Park, The Coffee Butler Amphitheater and the Truman Waterfront, as well as the world famous Mallory Square and Duval St. Home has been mostly owner occupied but is turnkey for a luxury vacation rental.

101 Front St Unit 8, Key West

$1,340,000

For Statistical Purposes: Life is GRAND in The Sanctuary @ Key West Golf Club! Beyond the 2nd set of gates, this exclusive private enclave is home to all-single-family residences. Beautifully maintained, surrounded by lush tropical foliage, this pristine home enjoys an enviable setting along #18 fairway, complete w/private pool, 4 verandas, off-street parking, carport & adjacent storage shed. Inside, a stunning fully renovated kitchen is truly a Chef's Dream, featuring all upgraded stainless appliances, expansive quartz countertops, floor-to-ceiling Kraft Maid custom cabinetry, Subway tile backsplash, upgraded lighting. The open living spaces flow beautifully to the outdoors. A versatile 10' x 12' den off the living room offers an ideal home office/potential 4th sleeping space w/addition of a closet/armoire. A convenient powder room completes the main level. The outdoor setting is equally impressive. Gorgeous Azek/Trex decking enhances the front veranda/steps, while the poolside retreat features the same beautiful low-maintenance, beautiful composite decking/steps/expansive pool deck. Lush gardens accented by river rock surround the front/side/rear yards, creating exceptional tropical privacy. Western exposure from the rear veranda and poolside setting provides the perfect backdrop for catching Key West's spectacular sunset colors. Upstairs, the spacious primary suite features vaulted ceilings, a beautifully renovated bath and French doors opening to a large private veranda nestled among the treetops. Two lovely guest bedrooms each enjoy French doors leading to the open veranda overlooking the peaceful promenade, and the guest bath has also been tastefully renovated. Additional attributes include a freshly painted exterior/fencing with so much more. Sanctuary owners enjoy all the amenities of Key West Golf Club, including 24-hour Resident Services, onsite Community Management, Clubhouse/Fitness Room, two gorgeous community pools. Welcome home to your own Sanctuary!

3 Beds ⋅ 3 Baths ⋅ 620936 MLS

For Statistical Purposes: Life is GRAND in The Sanctuary @ Key West Golf Club! Beyond the 2nd set of gates, this exclusive private enclave is home to all-single-family residences. Beautifully maintained, surrounded by lush tropical foliage, this pristine home enjoys an enviable setting along #18 fairway, complete w/private pool, 4 verandas, off-street parking, carport & adjacent storage shed. Inside, a stunning fully renovated kitchen is truly a Chef's Dream, featuring all upgraded stainless appliances, expansive quartz countertops, floor-to-ceiling Kraft Maid custom cabinetry, Subway tile backsplash, upgraded lighting. The open living spaces flow beautifully to the outdoors. A versatile 10' x 12' den off the living room offers an ideal home office/potential 4th sleeping space w/addition of a closet/armoire. A convenient powder room completes the main level. The outdoor setting is equally impressive. Gorgeous Azek/Trex decking enhances the front veranda/steps, while the poolside retreat features the same beautiful low-maintenance, beautiful composite decking/steps/expansive pool deck. Lush gardens accented by river rock surround the front/side/rear yards, creating exceptional tropical privacy. Western exposure from the rear veranda and poolside setting provides the perfect backdrop for catching Key West's spectacular sunset colors. Upstairs, the spacious primary suite features vaulted ceilings, a beautifully renovated bath and French doors opening to a large private veranda nestled among the treetops. Two lovely guest bedrooms each enjoy French doors leading to the open veranda overlooking the peaceful promenade, and the guest bath has also been tastefully renovated. Additional attributes include a freshly painted exterior/fencing with so much more. Sanctuary owners enjoy all the amenities of Key West Golf Club, including 24-hour Resident Services, onsite Community Management, Clubhouse/Fitness Room, two gorgeous community pools. Welcome home to your own Sanctuary!

213 Golf Club Dr, Key West

$1,325,000

Wake up to the rhythm of the Atlantic Ocean and sweeping sunrise views in the gated oceanfront community of Casa Caselles. This renovated Key West townhome offers four covered balconies facing the ocean and effortless lock-and-leave coastal living in one of Mid-Town Key West's most desirable waterfront locations. 1616 Atlantic Blvd. #13 spans 2,016 sq. ft. across three levels, featuring high ceilings, abundant natural light, and open-concept living designed to capture ocean views and island breezes. The main living level showcases Atlantic Ocean views, a spacious living and dining area, and an updated kitchen with stone countertops, stainless steel appliances, and custom Hansen & Bringle cabinetry. An architectural staircase anchors the home while large sliding doors open to covered balconies ideal for outdoor dining, morning coffee, or evening cocktails overlooking the water. The top floor features two spacious en-suite bedrooms, each designed for comfort and privacy, along with laundry on the bedroom level, dual-zone A/C, and generous storage throughout. A private landscaped courtyard with irrigation creates a quiet retreat and houses the propane whole-house generator, while the carport-level workshop and storage area provides space for bikes, kayaks, paddleboards, and beach gear. Impact windows and doors provide storm protection and peace of mind. Residents of Casa Caselles enjoy resort-style oceanfront amenities, including a large heated saltwater pool overlooking the Atlantic, expansive sun deck with loungers and umbrellas, gated privacy, pet friendly spaces, and a relaxed waterfront atmosphere. Located in Mid-Town Key West, this home is steps from the beach, dog park, tennis and pickleball courts, restaurants, and the weekly farmers market--an ideal primary residence, vacation home, or low-maintenance island retreat. * Seller may offer owner financing with competitive terms for qualified buyers*

2 Beds ⋅ 3 Baths ⋅ 619340 MLS

Wake up to the rhythm of the Atlantic Ocean and sweeping sunrise views in the gated oceanfront community of Casa Caselles. This renovated Key West townhome offers four covered balconies facing the ocean and effortless lock-and-leave coastal living in one of Mid-Town Key West's most desirable waterfront locations. 1616 Atlantic Blvd. #13 spans 2,016 sq. ft. across three levels, featuring high ceilings, abundant natural light, and open-concept living designed to capture ocean views and island breezes. The main living level showcases Atlantic Ocean views, a spacious living and dining area, and an updated kitchen with stone countertops, stainless steel appliances, and custom Hansen & Bringle cabinetry. An architectural staircase anchors the home while large sliding doors open to covered balconies ideal for outdoor dining, morning coffee, or evening cocktails overlooking the water. The top floor features two spacious en-suite bedrooms, each designed for comfort and privacy, along with laundry on the bedroom level, dual-zone A/C, and generous storage throughout. A private landscaped courtyard with irrigation creates a quiet retreat and houses the propane whole-house generator, while the carport-level workshop and storage area provides space for bikes, kayaks, paddleboards, and beach gear. Impact windows and doors provide storm protection and peace of mind. Residents of Casa Caselles enjoy resort-style oceanfront amenities, including a large heated saltwater pool overlooking the Atlantic, expansive sun deck with loungers and umbrellas, gated privacy, pet friendly spaces, and a relaxed waterfront atmosphere. Located in Mid-Town Key West, this home is steps from the beach, dog park, tennis and pickleball courts, restaurants, and the weekly farmers market--an ideal primary residence, vacation home, or low-maintenance island retreat. * Seller may offer owner financing with competitive terms for qualified buyers*

1616 Atlantic Blvd Unit 13, Key West

$1,325,000

The rare kind of antiquity that comes with all the comforts of today. Built before 1889 and reimagined for modern living, 419 Simonton Street A captures the true spirit of Old Town Key West—authentic, refined, and timeless. Once a mixed-use landmark with a flower shop below and a residence above, the home has been meticulously restored and reimagined from the ground up, with construction completed in January 2026 and every system, surface, and finish entirely new. Offered fully furnished with a bespoke interiors program by Ben Teague Design, the residence is layered with thoughtful selections, timeless materials, and a quiet sophistication that feels both intentional and effortlessly livable. The home offers two bedrooms and two-and-a-half baths, including an upstairs primary bedroom that opens to a classic Key West porch, while a second porch downstairs extends the living space and reinforces the home's effortless indoor-outdoor rhythm. Architect-led design and professionally curated landscaping elevate the curb appeal to a truly top-tier example of Old Town style—timeless proportions, thoughtful detailing, and a presence that feels historic without feeling precious. The property is part of a thoughtfully structured HOA, which also includes one attached residential unit positioned to the rear of the main home, as well as a separate detached unit located at the back of the property—allowing for shared stewardship while preserving privacy and architectural integrity. Set on one of the highest elevation blocks in Old Town and located in the coveted X-500 flood zone, this is a rare opportunity to own a home where heritage, design integrity, and modern peace of mind converge on one of Key West's most iconic streets.

2 Beds ⋅ 3 Baths ⋅ 618250 MLS

The rare kind of antiquity that comes with all the comforts of today. Built before 1889 and reimagined for modern living, 419 Simonton Street A captures the true spirit of Old Town Key West—authentic, refined, and timeless. Once a mixed-use landmark with a flower shop below and a residence above, the home has been meticulously restored and reimagined from the ground up, with construction completed in January 2026 and every system, surface, and finish entirely new. Offered fully furnished with a bespoke interiors program by Ben Teague Design, the residence is layered with thoughtful selections, timeless materials, and a quiet sophistication that feels both intentional and effortlessly livable. The home offers two bedrooms and two-and-a-half baths, including an upstairs primary bedroom that opens to a classic Key West porch, while a second porch downstairs extends the living space and reinforces the home's effortless indoor-outdoor rhythm. Architect-led design and professionally curated landscaping elevate the curb appeal to a truly top-tier example of Old Town style—timeless proportions, thoughtful detailing, and a presence that feels historic without feeling precious. The property is part of a thoughtfully structured HOA, which also includes one attached residential unit positioned to the rear of the main home, as well as a separate detached unit located at the back of the property—allowing for shared stewardship while preserving privacy and architectural integrity. Set on one of the highest elevation blocks in Old Town and located in the coveted X-500 flood zone, this is a rare opportunity to own a home where heritage, design integrity, and modern peace of mind converge on one of Key West's most iconic streets.

419 Simonton St Unit A, Key West

$1,300,000

Located on the desirable 1100 block of Olivia Street near the cemetery, this updated two bedroom, two bathroom, two story Conch home offers a balanced blend of Old Town character, privacy and walkability. This property is in the X flood zone and includes a pool and off street golf cart parking. This 1,125 square foot layout includes one bedroom and full bath on the first floor. The upstairs primary suite offers a full bath and direct access to a large private sun deck. The kitchen is generously sized for the home and opens to the main living area, with bar seating for four. Two sets of French doors in the living room open to the private backyard, allowing for indoor and outdoor use. The outdoor space is fully landscaped with mature trees and plants and includes a heated cocktail pool, outdoor dining area and additional side yard storage. A covered front porch faces Olivia Street and provides usable outdoor seating for morning coffee. Off street parking accommodates a six seater golf cart. The home is within easy walking distance to the harbor, dining and downtown Key West. Owner occupied full time for the past ten and a half years. Well suited for a primary residence, seasonal home or vacation rental in one of Old Town's most recognizable areas.

2 Beds ⋅ 2 Baths ⋅ 618079 MLS

Located on the desirable 1100 block of Olivia Street near the cemetery, this updated two bedroom, two bathroom, two story Conch home offers a balanced blend of Old Town character, privacy and walkability. This property is in the X flood zone and includes a pool and off street golf cart parking. This 1,125 square foot layout includes one bedroom and full bath on the first floor. The upstairs primary suite offers a full bath and direct access to a large private sun deck. The kitchen is generously sized for the home and opens to the main living area, with bar seating for four. Two sets of French doors in the living room open to the private backyard, allowing for indoor and outdoor use. The outdoor space is fully landscaped with mature trees and plants and includes a heated cocktail pool, outdoor dining area and additional side yard storage. A covered front porch faces Olivia Street and provides usable outdoor seating for morning coffee. Off street parking accommodates a six seater golf cart. The home is within easy walking distance to the harbor, dining and downtown Key West. Owner occupied full time for the past ten and a half years. Well suited for a primary residence, seasonal home or vacation rental in one of Old Town's most recognizable areas.

1107 Olivia St, Key West

$1,300,000

Prime mixed-use investment opportunity in the heart of Key West. This well-maintained historic building features two commercial units on the ground floor with excellent visibility and foot traffic, plus five 1-bed, 1-bath residential units upstairs, creating high, diversified income. The property offers classic Old Town character with functional updates, multiple electric meters, and solid rental performance. A rare side yard and covered upper porch add additional tenant appeal. Fully leased to established tenants, this turnkey asset is ideal for investors seeking stable cash flow in a highly desirable location, just minutes from Duval Street, beaches, and Key West's top dining and entertainment.

5 Beds ⋅ 7 Baths ⋅ 618332 MLS

Prime mixed-use investment opportunity in the heart of Key West. This well-maintained historic building features two commercial units on the ground floor with excellent visibility and foot traffic, plus five 1-bed, 1-bath residential units upstairs, creating high, diversified income. The property offers classic Old Town character with functional updates, multiple electric meters, and solid rental performance. A rare side yard and covered upper porch add additional tenant appeal. Fully leased to established tenants, this turnkey asset is ideal for investors seeking stable cash flow in a highly desirable location, just minutes from Duval Street, beaches, and Key West's top dining and entertainment.

1018 Truman Ave, Key West

$1,300,000

1011 Truman Avenue is a versatile Old Town opportunity that can easily live like a spacious single-family residence while offering great flexibility for guests or multi-generational living. Currently configured as three legal units with one covered off-street parking space and located in the desirable X-Flood Zone, the property features a 795 sq. ft. ground-floor space with an industrial feel and half bath that could be reimagined as additional living, entertaining, or hobby space, plus a 416 sq. ft. one-bedroom with full bath and kitchenette hookups—ideal for an efficiency or guest suite. Upstairs, a stunning 720 sq. ft. one-bedroom, one-bath loft feels like a private primary retreat with open living and dining areas, a partitioned bedroom, beautiful master bath, full kitchen, and a private covered patio. Together, the spaces create a unique opportunity to design a large Old Town Key West residence with flexible layouts for guests, extended family, or live/work use.

2 Beds ⋅ 3 Baths ⋅ 617055 MLS

1011 Truman Avenue is a versatile Old Town opportunity that can easily live like a spacious single-family residence while offering great flexibility for guests or multi-generational living. Currently configured as three legal units with one covered off-street parking space and located in the desirable X-Flood Zone, the property features a 795 sq. ft. ground-floor space with an industrial feel and half bath that could be reimagined as additional living, entertaining, or hobby space, plus a 416 sq. ft. one-bedroom with full bath and kitchenette hookups—ideal for an efficiency or guest suite. Upstairs, a stunning 720 sq. ft. one-bedroom, one-bath loft feels like a private primary retreat with open living and dining areas, a partitioned bedroom, beautiful master bath, full kitchen, and a private covered patio. Together, the spaces create a unique opportunity to design a large Old Town Key West residence with flexible layouts for guests, extended family, or live/work use.

1011 Truman Ave, Key West

$1,300,000

This beautifully restored old Key West home offers the perfect tropical escape. Located just a block from Duval Street, Garden of Roses combines historic charm with modern upgrades, making it an ideal vacation home. Currently being rented as a monthly vacation rental! Enjoy a spacious layout with 3 bedrooms, a high-end kitchen, and bright, open living areas. Relax outdoors with a private hot tub, lush gardens, and multiple seating areas. The home also features off-street parking, hot tub, lusciously landscaped patio for entertaining or outdoor dining. Located right in the heart of Old Town Key West, just steps from the Southernmost Point and Duval Street, this home offers the perfect blend of comfort and convenience. Schedule your showing today to experience this slice of paradise!

3 Beds ⋅ 2 Baths ⋅ 617908 MLS

This beautifully restored old Key West home offers the perfect tropical escape. Located just a block from Duval Street, Garden of Roses combines historic charm with modern upgrades, making it an ideal vacation home. Currently being rented as a monthly vacation rental! Enjoy a spacious layout with 3 bedrooms, a high-end kitchen, and bright, open living areas. Relax outdoors with a private hot tub, lush gardens, and multiple seating areas. The home also features off-street parking, hot tub, lusciously landscaped patio for entertaining or outdoor dining. Located right in the heart of Old Town Key West, just steps from the Southernmost Point and Duval Street, this home offers the perfect blend of comfort and convenience. Schedule your showing today to experience this slice of paradise!

1202 Whitehead St, Key West

$1,275,000

Experience an authentic island lifestyle at this classic conch cottage nestled in the heart of Old Town. Located on a quiet lane, just steps to Duval Street and The Green Parrot, this updated home provides a unbeatable location for walking to all of the best spots in Key West. Designed in the iconic ''conch cottage'' style, the interior features Dade County Pine walls, vaulted ceilings, and modern appliances. Enjoy the ease of main-floor living with two bedrooms--each paired with a dedicated bathroom--complemented by a versatile loft space featuring the third bedroom and bathroom. The private, fully fenced outdoor space is surrounded by lush tropical greenery and offers the perfect outdoor dining setting. The front porch provides a discrete vantage point to enjoy morning coffee or evening cocktails while watching the world go by on Aronovitz Lane. Newly installed impact rated doors and windows, a newer roof (replaced in 2021), and X flood zone location keep insurances very reasonable. Offered fully furnished and with years of monthly vacation rental history, this home is ready for it's next owner, weather as a Winter home, full-time residence, or investment property.

3 Beds ⋅ 3 Baths ⋅ 618423 MLS

Experience an authentic island lifestyle at this classic conch cottage nestled in the heart of Old Town. Located on a quiet lane, just steps to Duval Street and The Green Parrot, this updated home provides a unbeatable location for walking to all of the best spots in Key West. Designed in the iconic ''conch cottage'' style, the interior features Dade County Pine walls, vaulted ceilings, and modern appliances. Enjoy the ease of main-floor living with two bedrooms--each paired with a dedicated bathroom--complemented by a versatile loft space featuring the third bedroom and bathroom. The private, fully fenced outdoor space is surrounded by lush tropical greenery and offers the perfect outdoor dining setting. The front porch provides a discrete vantage point to enjoy morning coffee or evening cocktails while watching the world go by on Aronovitz Lane. Newly installed impact rated doors and windows, a newer roof (replaced in 2021), and X flood zone location keep insurances very reasonable. Offered fully furnished and with years of monthly vacation rental history, this home is ready for it's next owner, weather as a Winter home, full-time residence, or investment property.

4 Aronovitz Ln, Key West

$1,275,000

Unique opportunity for a creative buyer to own this 3 residential unit property. Would be a great for business owner looking for employee housing. Update all 3 homes for a family compound. Currently setup as roommate style living with a gross income of $15,000. a month. Don't miss this great location in Bahama Village steps from the Truman Waterfront, Ft. Zach beach, restaurants, galleries, shops and more!

8 Beds ⋅ 10 Baths ⋅ 615510 MLS

Unique opportunity for a creative buyer to own this 3 residential unit property. Would be a great for business owner looking for employee housing. Update all 3 homes for a family compound. Currently setup as roommate style living with a gross income of $15,000. a month. Don't miss this great location in Bahama Village steps from the Truman Waterfront, Ft. Zach beach, restaurants, galleries, shops and more!

720-726 Emma St, Key West

$1,270,000

Renovated Midtown retreat offering exceptional flexibility, thoughtful updates, and the ideal layout for modern island living. Elevated and designed for comfortable one-level living, this 4 bedroom, 3.5 bathroom home features a versatile floor plan. At the heart of the home, the newly renovated kitchen blends style and functionality with a large center island, custom cabinetry, granite countertops, and a high-end appliance package. Privately situated at the rear of the property, the fully equipped guest cottage includes a kitchenette, living area, and full bath, offering excellent flexibility for guests, extended family, or potential rental use. An additional studio space adjacent to the pool is ideal for a home office, art studio, fitness room, or wellness retreat. The sun-filled patio and pool provide the perfect setting for relaxing afternoons or hosting weekend gatherings, while the spacious lot offers ample off-street parking for vehicles and a golf cart. Ideally located just minutes from shopping, dining, and schools, this property offers a peaceful residential setting with convenient access to everything Midtown has to offer. With its combination of updated interiors, multiple living spaces, and resort-style outdoor amenities, 2211 Staples Avenue presents a rare opportunity to enjoy space, comfort, and versatility in the heart of Key West.

4 Beds ⋅ 4 Baths ⋅ 618756 MLS

Renovated Midtown retreat offering exceptional flexibility, thoughtful updates, and the ideal layout for modern island living. Elevated and designed for comfortable one-level living, this 4 bedroom, 3.5 bathroom home features a versatile floor plan. At the heart of the home, the newly renovated kitchen blends style and functionality with a large center island, custom cabinetry, granite countertops, and a high-end appliance package. Privately situated at the rear of the property, the fully equipped guest cottage includes a kitchenette, living area, and full bath, offering excellent flexibility for guests, extended family, or potential rental use. An additional studio space adjacent to the pool is ideal for a home office, art studio, fitness room, or wellness retreat. The sun-filled patio and pool provide the perfect setting for relaxing afternoons or hosting weekend gatherings, while the spacious lot offers ample off-street parking for vehicles and a golf cart. Ideally located just minutes from shopping, dining, and schools, this property offers a peaceful residential setting with convenient access to everything Midtown has to offer. With its combination of updated interiors, multiple living spaces, and resort-style outdoor amenities, 2211 Staples Avenue presents a rare opportunity to enjoy space, comfort, and versatility in the heart of Key West.

2211 Staples Ave, Key West

$1,270,000

Perfectly situated just three blocks from Duval Street and two from the grocery store, this one-of-a-kind, fully furnished penthouse has been meticulously renovated to deliver unmatched luxury living in the heart of Old Town Key West. Offering rare off-street parking, this light-filled residence is perched among the treetops and features a private balcony with serene pool and garden views. Inside, you'll find soaring ceilings, warm hardwood floors, Dade County pine accent walls, and impact-resistant doors that blend historic charm with modern comfort. The chef's kitchen is thoughtfully designed with Corian countertops, Miele appliances, an induction cooktop and convection oven, a breakfast bar ideal for dining or entertaining, and generous pantry space. The same Corian surfaces extend into the bath for a cohesive, upscale finish. A Miele washer and dryer add convenience to everyday living. The open floor plan flows seamlessly from the kitchen to the dining and living areas, creating an inviting space for relaxing or hosting guests. Original stained-glass transom windows add a touch of timeless character, reflecting the home's historic roots while complementing its modern updates. This lovingly restored condominium includes an assigned parking space, secure building access, and beautifully maintained common grounds featuring lush landscaping, a sparkling pool, sundeck, and patio area.

2 Beds ⋅ 2 Baths ⋅ 617634 MLS

Perfectly situated just three blocks from Duval Street and two from the grocery store, this one-of-a-kind, fully furnished penthouse has been meticulously renovated to deliver unmatched luxury living in the heart of Old Town Key West. Offering rare off-street parking, this light-filled residence is perched among the treetops and features a private balcony with serene pool and garden views. Inside, you'll find soaring ceilings, warm hardwood floors, Dade County pine accent walls, and impact-resistant doors that blend historic charm with modern comfort. The chef's kitchen is thoughtfully designed with Corian countertops, Miele appliances, an induction cooktop and convection oven, a breakfast bar ideal for dining or entertaining, and generous pantry space. The same Corian surfaces extend into the bath for a cohesive, upscale finish. A Miele washer and dryer add convenience to everyday living. The open floor plan flows seamlessly from the kitchen to the dining and living areas, creating an inviting space for relaxing or hosting guests. Original stained-glass transom windows add a touch of timeless character, reflecting the home's historic roots while complementing its modern updates. This lovingly restored condominium includes an assigned parking space, secure building access, and beautifully maintained common grounds featuring lush landscaping, a sparkling pool, sundeck, and patio area.

800 Fleming St Unit B-3, Key West

$1,254,750

A welcoming covered front porch sets the tone for this exceptional townhome, offering the perfect place to enjoy your morning coffee or unwind with an evening cocktail while embracing the island breeze. Timeless craftsmanship meets modern comfort in this beautifully designed 3-bedroom, 3-bathroom townhome, thoughtfully created for effortless living, exceptional functionality, and relaxed tropical elegance. Step inside to a generous entry foyer that offers endless possibilities--ideal as a home office, sitting room, or welcoming reception space. The open-concept floor plan seamlessly connects the chef's kitchen, dining area, and living room, creating an inviting space for everyday living and entertaining. The custom kitchen is appointed with quality cabinetry and high-end appliances sure to impress. The spacious primary suite is conveniently located on the main level, offering privacy and the ease of single-level living. Upstairs are two additional guest bedrooms and a full bath, complemented by hardwood flooring, while the first floor showcases classic Mexican tile that adds warmth and island character. Step outside to your secluded backyard oasis. Surrounded by lush tropical landscaping, the heated pool and spa with a tranquil water feature create the perfect setting for relaxation. Multiple outdoor living and entertaining areas provide ample space for dining al fresco, hosting family and friends, or simply enjoying the peaceful surroundings. Built with durable Indian block construction, this exceptional home offers lasting quality and timeless appeal in the X500 zone. Whether you're searching for a full-time residence, vacation getaway, or investment property, this townhome delivers the perfect blend of luxury, privacy, and tropical living.

3 Beds ⋅ 3 Baths ⋅ 620423 MLS

A welcoming covered front porch sets the tone for this exceptional townhome, offering the perfect place to enjoy your morning coffee or unwind with an evening cocktail while embracing the island breeze. Timeless craftsmanship meets modern comfort in this beautifully designed 3-bedroom, 3-bathroom townhome, thoughtfully created for effortless living, exceptional functionality, and relaxed tropical elegance. Step inside to a generous entry foyer that offers endless possibilities--ideal as a home office, sitting room, or welcoming reception space. The open-concept floor plan seamlessly connects the chef's kitchen, dining area, and living room, creating an inviting space for everyday living and entertaining. The custom kitchen is appointed with quality cabinetry and high-end appliances sure to impress. The spacious primary suite is conveniently located on the main level, offering privacy and the ease of single-level living. Upstairs are two additional guest bedrooms and a full bath, complemented by hardwood flooring, while the first floor showcases classic Mexican tile that adds warmth and island character. Step outside to your secluded backyard oasis. Surrounded by lush tropical landscaping, the heated pool and spa with a tranquil water feature create the perfect setting for relaxation. Multiple outdoor living and entertaining areas provide ample space for dining al fresco, hosting family and friends, or simply enjoying the peaceful surroundings. Built with durable Indian block construction, this exceptional home offers lasting quality and timeless appeal in the X500 zone. Whether you're searching for a full-time residence, vacation getaway, or investment property, this townhome delivers the perfect blend of luxury, privacy, and tropical living.

907 United St, Key West

$1,250,000

Rare Luxurious Atlantic Oceanfront Concrete 3 story home. 2 Bedrooms 2 1/2 bathrooms located in a private gated community. Ocean views from your balconies. This exquisite home has stainless steel appliances, custom cabinetry, vaulted ceilings, tiled carport, oversized well-manicured, private back yard. Huge storage room with built in shelving. This rare unit has the largest backyard in the community and an extra private parking space. These are just a few of the amenities this lavish fortress offers. Casa Caselles is located directly on the Atlantic Ocean between 2 nature preserves with a quaint Mediterranean feel and offers a front row seat to breathtaking sunrises and wildlife. The pool is beachside and allows its owners VIP seating for star gazing, fireworks and watersports. This 20 home complex is owner occupied only. No rentals are allowed. Schedule your private showing now. No rentals allowed. Owner financing is available.

2 Beds ⋅ 3 Baths ⋅ 617125 MLS

Rare Luxurious Atlantic Oceanfront Concrete 3 story home. 2 Bedrooms 2 1/2 bathrooms located in a private gated community. Ocean views from your balconies. This exquisite home has stainless steel appliances, custom cabinetry, vaulted ceilings, tiled carport, oversized well-manicured, private back yard. Huge storage room with built in shelving. This rare unit has the largest backyard in the community and an extra private parking space. These are just a few of the amenities this lavish fortress offers. Casa Caselles is located directly on the Atlantic Ocean between 2 nature preserves with a quaint Mediterranean feel and offers a front row seat to breathtaking sunrises and wildlife. The pool is beachside and allows its owners VIP seating for star gazing, fireworks and watersports. This 20 home complex is owner occupied only. No rentals are allowed. Schedule your private showing now. No rentals allowed. Owner financing is available.

1616 Atlantic Blvd Unit 5, Key West

$1,225,000

Closest living to OLD TOWN with a boat slip!! Peace and quiet and a boaters delight! This small condo complex located in the beautiful Meadows neighborhood has an ordinance against vacation rentals which ensures consistent tranquility with a virtually private pool. One of the only properties close to Old Town where you can keep your boat in the water with an assigned boat slip. With the rising cost of boat slips and marina rates, the slip can save you upwards of a $1000 per month. This third floor 2BR/2BA unit allows for panoramic views of the marina and Key West. The property has had many upgrades during this ownership including new decorative floors with a coastal feel, an upgraded bathroom, new AC, washer and dryer, and some appliances. Enjoy entering a cool car with the covered parking, a rare find in The Meadows. Large private exterior storage space is included. The views are a must see!

2 Beds ⋅ 2 Baths ⋅ 603597 MLS

Closest living to OLD TOWN with a boat slip!! Peace and quiet and a boaters delight! This small condo complex located in the beautiful Meadows neighborhood has an ordinance against vacation rentals which ensures consistent tranquility with a virtually private pool. One of the only properties close to Old Town where you can keep your boat in the water with an assigned boat slip. With the rising cost of boat slips and marina rates, the slip can save you upwards of a $1000 per month. This third floor 2BR/2BA unit allows for panoramic views of the marina and Key West. The property has had many upgrades during this ownership including new decorative floors with a coastal feel, an upgraded bathroom, new AC, washer and dryer, and some appliances. Enjoy entering a cool car with the covered parking, a rare find in The Meadows. Large private exterior storage space is included. The views are a must see!

833 Eisenhower Dr Unit 303, Key West

$1,215,000

Welcome to 1718 United Street, a beautifully renovated home in the heart of Key West offering modern comfort with timeless island charm. This spacious residence features 3 bedrooms and 2.5 bathrooms, including a stunning spa-style master bath with double sinks and dual shower heads for the ultimate retreat. The bright and open layout showcases elegant marble countertops, thoughtfully designed finishes, and inviting living spaces perfect for both relaxing and entertaining. Step outside to enjoy the side porch facing the driveway, an ideal spot for morning coffee or evening gatherings. A standing seam metal roof adds both style and durability, giving peace of mind for years to come. To enhance the island lifestyle even further, the seller has drawings available to the buyer for a pool and tiki hut, offering the opportunity to create your own backyard oasis. Ideally located just a short bike ride to the vibrant energy of downtown Key West and world-famous Duval Street, this property combines convenience, comfort, and style—move-in ready and waiting to be enjoyed as your new island home.

3 Beds ⋅ 3 Baths ⋅ 616195 MLS

Welcome to 1718 United Street, a beautifully renovated home in the heart of Key West offering modern comfort with timeless island charm. This spacious residence features 3 bedrooms and 2.5 bathrooms, including a stunning spa-style master bath with double sinks and dual shower heads for the ultimate retreat. The bright and open layout showcases elegant marble countertops, thoughtfully designed finishes, and inviting living spaces perfect for both relaxing and entertaining. Step outside to enjoy the side porch facing the driveway, an ideal spot for morning coffee or evening gatherings. A standing seam metal roof adds both style and durability, giving peace of mind for years to come. To enhance the island lifestyle even further, the seller has drawings available to the buyer for a pool and tiki hut, offering the opportunity to create your own backyard oasis. Ideally located just a short bike ride to the vibrant energy of downtown Key West and world-famous Duval Street, this property combines convenience, comfort, and style—move-in ready and waiting to be enjoyed as your new island home.

1718 United St, Key West

$1,200,000

FLIP FLOPS INLCUDED! Some homes are just addresses. This one is a lifestyle. Tucked into the heart of Old Town Key West, this beautiful historic Conch home is wrapped in the warmth of original Dade County pine and rich hardwood floors -- the kind of craftsmanship that simply isn't built anymore. The main house offers three bedrooms and a fully renovated bath, anchored by a large kitchen with generous cabinet space.. A fully enclosed porch is your place for morning coffee, chatting around the table or dining while overlooking the pool. Central air conditioning keeps things cool. Every window and door has been upgraded to impact, giving you peace of mind alongside the charm. Step outside and the magic continues. A sparkling pool with a waterfall feature and Trex decking invites you to linger. An outdoor shower makes coming in from the water effortless. The fully fenced front and back yards create a private tropical sanctuary, and off-street parking -- a true luxury in Old Town -- takes the stress out of coming home. The guest cottage is its own retreat, offering one bedroom, one bath, and a Murphy bed that makes the space as flexible as your plans. Whether it becomes a private getaway for family and friends, a creative studio or a detached office, it gives this property a versatility that is genuinely rare. The location is the final piece that makes everything click. A ten-minute walk from Duval Street -live music, art galleries, open-air restaurants, theaters and the electric pulse that makes Key West unlike anywhere else on earth. 7 minutes the other way brings you to the White Street District know for Fausto's Food Palace, where locals have shopped for generations, and the legendary Sandy's Café. This property comes fully turn-key, bedding, housewares, pool toys, bicycles, and yes, flip flops are included. Whether you wanting a second home, a monthly vacation rental or simply ready to walk through the door and start living living in paradise.

4 Beds ⋅ 2 Baths ⋅ 619738 MLS

FLIP FLOPS INLCUDED! Some homes are just addresses. This one is a lifestyle. Tucked into the heart of Old Town Key West, this beautiful historic Conch home is wrapped in the warmth of original Dade County pine and rich hardwood floors -- the kind of craftsmanship that simply isn't built anymore. The main house offers three bedrooms and a fully renovated bath, anchored by a large kitchen with generous cabinet space.. A fully enclosed porch is your place for morning coffee, chatting around the table or dining while overlooking the pool. Central air conditioning keeps things cool. Every window and door has been upgraded to impact, giving you peace of mind alongside the charm. Step outside and the magic continues. A sparkling pool with a waterfall feature and Trex decking invites you to linger. An outdoor shower makes coming in from the water effortless. The fully fenced front and back yards create a private tropical sanctuary, and off-street parking -- a true luxury in Old Town -- takes the stress out of coming home. The guest cottage is its own retreat, offering one bedroom, one bath, and a Murphy bed that makes the space as flexible as your plans. Whether it becomes a private getaway for family and friends, a creative studio or a detached office, it gives this property a versatility that is genuinely rare. The location is the final piece that makes everything click. A ten-minute walk from Duval Street -live music, art galleries, open-air restaurants, theaters and the electric pulse that makes Key West unlike anywhere else on earth. 7 minutes the other way brings you to the White Street District know for Fausto's Food Palace, where locals have shopped for generations, and the legendary Sandy's Café. This property comes fully turn-key, bedding, housewares, pool toys, bicycles, and yes, flip flops are included. Whether you wanting a second home, a monthly vacation rental or simply ready to walk through the door and start living living in paradise.

928 United St, Key West

$1,200,000

Discover the charm of 2105 Fogarty Ave—an inviting Key West gem that blends character, comfort, and an ideal island lifestyle. From the moment you step inside, you'll find bright, welcoming spaces filled with personality and warmth. Each room offers thoughtful details and natural light, creating an atmosphere that feels instantly like home. Enjoy the lush, sun-filled garden—a private outdoor retreat surrounded by tropical landscaping, perfect for morning coffee, relaxing afternoons, or entertaining under the evening sky. Inside, the open-concept living area provides an easy flow for everyday living and gatherings, enhanced by tasteful décor and a relaxed Key West vibe. The kitchen combines modern functionality with timeless charm, offering everything you need to cook, connect, and enjoy time with friends and family. Every space in this home has been carefully curated to celebrate the unique spirit of island living. And with a prime location, you're just a short bicycle ride from Key West's lively dining scene, nightlife, and beautiful beaches. Experience the best of Key West at 2105 Fogarty Ave—a home where comfort meets coastal charm. Don't miss the opportunity to make it yours. Call to schedule a showing today!

4 Beds ⋅ 3 Baths ⋅ 617092 MLS

Discover the charm of 2105 Fogarty Ave—an inviting Key West gem that blends character, comfort, and an ideal island lifestyle. From the moment you step inside, you'll find bright, welcoming spaces filled with personality and warmth. Each room offers thoughtful details and natural light, creating an atmosphere that feels instantly like home. Enjoy the lush, sun-filled garden—a private outdoor retreat surrounded by tropical landscaping, perfect for morning coffee, relaxing afternoons, or entertaining under the evening sky. Inside, the open-concept living area provides an easy flow for everyday living and gatherings, enhanced by tasteful décor and a relaxed Key West vibe. The kitchen combines modern functionality with timeless charm, offering everything you need to cook, connect, and enjoy time with friends and family. Every space in this home has been carefully curated to celebrate the unique spirit of island living. And with a prime location, you're just a short bicycle ride from Key West's lively dining scene, nightlife, and beautiful beaches. Experience the best of Key West at 2105 Fogarty Ave—a home where comfort meets coastal charm. Don't miss the opportunity to make it yours. Call to schedule a showing today!

2105 Fogarty Ave, Key West

$1,184,000

Welcome to 1006 16th Terrace, a charming two-story residence nestled in the New Town area of Key West, Florida. Whether you are looking for a single-family home or a Multigenerational living arrangement, this property at 1006 16th Terrace combines comfort, functionality & the charm of Key West living. Home boasts 5 bedrooms and 3 bathrooms offering a floorplan that will accommodate multiple situations. The exterior of the home is a testament to meticulous landscaping, creating a serene & inviting atmosphere. A detached storage unit provides additional space for a multitude of uses. The residence features a two-zone air conditioning system, ensuring optimal comfort throughout the year. The home has been recently painted, adding to its fresh & well-kept appearance. The original ground level home was built in 1965; however, the second story addition was built in 1993, with an open floorplan, bamboo floors and a window view of the Gulf of American. Enjoy the oversized balcony among the many trees. The home is equipped with storm rated windows and doors for your added protection. Some of the room photos have been virtually staged...

5 Beds ⋅ 4 Baths ⋅ 614318 MLS

Welcome to 1006 16th Terrace, a charming two-story residence nestled in the New Town area of Key West, Florida. Whether you are looking for a single-family home or a Multigenerational living arrangement, this property at 1006 16th Terrace combines comfort, functionality & the charm of Key West living. Home boasts 5 bedrooms and 3 bathrooms offering a floorplan that will accommodate multiple situations. The exterior of the home is a testament to meticulous landscaping, creating a serene & inviting atmosphere. A detached storage unit provides additional space for a multitude of uses. The residence features a two-zone air conditioning system, ensuring optimal comfort throughout the year. The home has been recently painted, adding to its fresh & well-kept appearance. The original ground level home was built in 1965; however, the second story addition was built in 1993, with an open floorplan, bamboo floors and a window view of the Gulf of American. Enjoy the oversized balcony among the many trees. The home is equipped with storm rated windows and doors for your added protection. Some of the room photos have been virtually staged...

1006 16th Ter, Key West

$1,175,000

The Secret Garden House on Johnson Lane is more than a home, this is a hidden sanctuary in the heart of Old Town Key West -- a soulful retreat where historic architecture, tropical landscape, and effortless indoor-outdoor living exist in complete harmony. Rich in character, creativity, and quiet beauty, the property captures the essence of authentic island living with a sense of intimacy and calm that feels worlds away. Celebrated for its distinctive design, the home has been featured in Design Within Reach Magazine and other notable publications highlighting its iconic interpretation of tropical modernism and handcrafted island living. Originally built as two modest cigar workers' cottages in the early 1900s, the homes were thoughtfully joined and transformed into a one-of-a-kind compound that honors the simplicity and artistry of old Key West. Lush exotic and indigenous landscaping unfolds as a private garden escape layered with mature palms, native plantings, orchids, and a rare working well that speaks to the home's historic roots. Natural light and warm ocean breezes move effortlessly throughout the interiors. Skylights, louvered openings, covered breezeways, and disappearing sliders create a seamless connection between inside and out, while handcrafted details and natural materials bring warmth and texture to every space. The interiors are understated yet deeply refined -- exposed beams, whitewashed walls, custom built-ins, lofted spaces, and quiet corners designed for reading, creating, and gathering. Every room feels intentional, balancing simplicity with an unmistakable sense of soul. Outdoor living is woven into the experience of the home. Intimate decks, shaded seating areas, and garden pathways invite slow mornings, candlelit dinners, and evenings spent beneath the palms surrounded by the sounds of the tropics. Private, artistic, and entirely authentic, this is the kind of Key West property rarely offered.

2 Beds ⋅ 2 Baths ⋅ 619811 MLS

The Secret Garden House on Johnson Lane is more than a home, this is a hidden sanctuary in the heart of Old Town Key West -- a soulful retreat where historic architecture, tropical landscape, and effortless indoor-outdoor living exist in complete harmony. Rich in character, creativity, and quiet beauty, the property captures the essence of authentic island living with a sense of intimacy and calm that feels worlds away. Celebrated for its distinctive design, the home has been featured in Design Within Reach Magazine and other notable publications highlighting its iconic interpretation of tropical modernism and handcrafted island living. Originally built as two modest cigar workers' cottages in the early 1900s, the homes were thoughtfully joined and transformed into a one-of-a-kind compound that honors the simplicity and artistry of old Key West. Lush exotic and indigenous landscaping unfolds as a private garden escape layered with mature palms, native plantings, orchids, and a rare working well that speaks to the home's historic roots. Natural light and warm ocean breezes move effortlessly throughout the interiors. Skylights, louvered openings, covered breezeways, and disappearing sliders create a seamless connection between inside and out, while handcrafted details and natural materials bring warmth and texture to every space. The interiors are understated yet deeply refined -- exposed beams, whitewashed walls, custom built-ins, lofted spaces, and quiet corners designed for reading, creating, and gathering. Every room feels intentional, balancing simplicity with an unmistakable sense of soul. Outdoor living is woven into the experience of the home. Intimate decks, shaded seating areas, and garden pathways invite slow mornings, candlelit dinners, and evenings spent beneath the palms surrounded by the sounds of the tropics. Private, artistic, and entirely authentic, this is the kind of Key West property rarely offered.

816 Johnson Ln, Key West

$1,170,000

Hidden away on one of Old Town's most storied streets, 1016 Varela St. Rear is the kind of Key West address that feels like a private discovery. Originally constructed in the 1920s, this piece of living Key West history has been thoughtfully renovated while honoring the character that only a century of island life can impart. Tucked discreetly behind the street, the fully restored 3-bedroom, 3-bathroom residence offers a rare sense of seclusion in the heart of historic Old Town -- without sacrificing a single step of the legendary walkability that defines this neighborhood. Duval Street, world-class dining, the harbor, and the full tapestry of Key West life are all moments away on foot. Arrive home to a covered front porch -- the quintessential Key West perch for morning coffee or evening cocktails. Inside, soaring cathedral ceilings flood the living spaces with light and volume, while refinished hardwood floors, an updated kitchen, and impact windows throughout speak to a renovation done with care and intention. The private rear yard offers room for a pool, a rare opportunity to create your own tropical retreat in the heart of Old Town. A separate upstairs apartment with its own private entrance offers exceptional flexibility: a sanctuary for a young adult, an elegant in-law suite, or an income-producing rental that helps carry the property. For the discerning buyer, two details stand above the rest: 1016 Varela Rear sits in an X flood zone -- the premier flood designation in the Keys, carrying no flood insurance requirement -- and the property carries an assumable VA loan, a remarkable financial advantage for qualified buyers in today's market. In Old Town Key West, a century-old home with this much flexibility and this little compromise is extraordinarily rare. Welcome to your hidden corner of paradise.

3 Beds ⋅ 3 Baths ⋅ 619952 MLS

Hidden away on one of Old Town's most storied streets, 1016 Varela St. Rear is the kind of Key West address that feels like a private discovery. Originally constructed in the 1920s, this piece of living Key West history has been thoughtfully renovated while honoring the character that only a century of island life can impart. Tucked discreetly behind the street, the fully restored 3-bedroom, 3-bathroom residence offers a rare sense of seclusion in the heart of historic Old Town -- without sacrificing a single step of the legendary walkability that defines this neighborhood. Duval Street, world-class dining, the harbor, and the full tapestry of Key West life are all moments away on foot. Arrive home to a covered front porch -- the quintessential Key West perch for morning coffee or evening cocktails. Inside, soaring cathedral ceilings flood the living spaces with light and volume, while refinished hardwood floors, an updated kitchen, and impact windows throughout speak to a renovation done with care and intention. The private rear yard offers room for a pool, a rare opportunity to create your own tropical retreat in the heart of Old Town. A separate upstairs apartment with its own private entrance offers exceptional flexibility: a sanctuary for a young adult, an elegant in-law suite, or an income-producing rental that helps carry the property. For the discerning buyer, two details stand above the rest: 1016 Varela Rear sits in an X flood zone -- the premier flood designation in the Keys, carrying no flood insurance requirement -- and the property carries an assumable VA loan, a remarkable financial advantage for qualified buyers in today's market. In Old Town Key West, a century-old home with this much flexibility and this little compromise is extraordinarily rare. Welcome to your hidden corner of paradise.

1016 Varela St Unit Rear, Key West

$1,150,000

Welcome home! Charming Old Town Key West Cottage with Off-Street Parking. Situated on a desirable corner lot in Old Town, this 2-bedroom, 1-bath conch cottage offers the quintessential Key West lifestyle. Inside, natural light highlights the home's historic Dade County pine walls and original wood floors, blending timeless character with modern comfort. The updated kitchen and dining area create an inviting space for entertaining, flowing seamlessly into the living room and extending to a private outdoor retreat. Located in the desirable X flood zone, this property combines historic charm, modern updates, and an exceptional location--everything you need to experience the best of Key West living.

2 Beds ⋅ 1 Baths ⋅ 620334 MLS

Welcome home! Charming Old Town Key West Cottage with Off-Street Parking. Situated on a desirable corner lot in Old Town, this 2-bedroom, 1-bath conch cottage offers the quintessential Key West lifestyle. Inside, natural light highlights the home's historic Dade County pine walls and original wood floors, blending timeless character with modern comfort. The updated kitchen and dining area create an inviting space for entertaining, flowing seamlessly into the living room and extending to a private outdoor retreat. Located in the desirable X flood zone, this property combines historic charm, modern updates, and an exceptional location--everything you need to experience the best of Key West living.

1124 Watson St, Key West

$1,150,000

Welcome to 2827 Staples Avenue, a beautifully updated Key West residence where timeless island charm meets modern living. From its manicured front lawn framed by tropical landscaping and a welcoming front porch, to its private backyard retreat, this home captures the essence of easy Key West living. Inside, the open layout flows effortlessly with vaulted ceilings, abundant natural light, and a blend of hardwood and modern plank flooring. The remodeled kitchen features quartz countertops, shaker cabinetry, and stainless steel appliances, while the bathrooms have been thoughtfully designed with spa-inspired finishes including a soaking tub, dual vanities, and a walk-in shower. A dedicated laundry room and multiple living areas provide comfort and convenience. Step outside to your private tropical retreat, complete with a sparkling pool, covered porch with fans and string lighting, lush landscaping, and a custom-built bar perfect for entertaining family and friends. What truly sets this property apart is the solar panel system, designed to provide energy efficiency and keep electric bills almost nonexistent—an incredible benefit rarely found in the Keys. Centrally located in Midtown, this home offers the perfect blend of style, sustainability, and the relaxed island lifestyle, just minutes from beaches, dining, and Old Town.

4 Beds ⋅ 2 Baths ⋅ 616764 MLS

Welcome to 2827 Staples Avenue, a beautifully updated Key West residence where timeless island charm meets modern living. From its manicured front lawn framed by tropical landscaping and a welcoming front porch, to its private backyard retreat, this home captures the essence of easy Key West living. Inside, the open layout flows effortlessly with vaulted ceilings, abundant natural light, and a blend of hardwood and modern plank flooring. The remodeled kitchen features quartz countertops, shaker cabinetry, and stainless steel appliances, while the bathrooms have been thoughtfully designed with spa-inspired finishes including a soaking tub, dual vanities, and a walk-in shower. A dedicated laundry room and multiple living areas provide comfort and convenience. Step outside to your private tropical retreat, complete with a sparkling pool, covered porch with fans and string lighting, lush landscaping, and a custom-built bar perfect for entertaining family and friends. What truly sets this property apart is the solar panel system, designed to provide energy efficiency and keep electric bills almost nonexistent—an incredible benefit rarely found in the Keys. Centrally located in Midtown, this home offers the perfect blend of style, sustainability, and the relaxed island lifestyle, just minutes from beaches, dining, and Old Town.

2827 Staples Ave, Key West

$1,135,000

Welcome to 1120 Stump Lane, a beautifully renovated 2-bedroom, 2-bath retreat tucked away on a highly desirable and quiet lane in the heart of Old Town Key West. This turnkey home offers true peace of mind, with major updates completed in recent years, including a new roof, plumbing, air conditioning systems, and electrical. Impact windows and doors further enhance comfort and security. From the moment you arrive, you'll be charmed by the inviting front porch, classic wood shutters, and quality craftsmanship throughout. Inside, the living room welcomes you with stunning vaulted ceilings and an airy, open feel. The thoughtfully designed floor plan flows seamlessly into the fully renovated kitchen, featuring an island, bar top with seating, quartz countertop, upgraded appliances, and abundant cabinetry. The first floor also offers a guest bedroom, a full bath, and a convenient laundry area. Upstairs, the primary suite provides a peaceful escape, complete with an ensuite bathroom, office nook, built-ins, and two closets for ample storage. Step outside to your private backyard oasis, where a composite deck and low-maintenance yard create the perfect setting for sunbathing, relaxing, or enjoying an al fresco meal. The location is unbeatable--just a short stroll to top-rated restaurants, the historic seaport, charming shops and boutiques, and world-famous Duval Street--yet quietly removed on a serene, private lane. Move right in and start enjoying the best of Key West living.

2 Beds ⋅ 2 Baths ⋅ 618951 MLS

Welcome to 1120 Stump Lane, a beautifully renovated 2-bedroom, 2-bath retreat tucked away on a highly desirable and quiet lane in the heart of Old Town Key West. This turnkey home offers true peace of mind, with major updates completed in recent years, including a new roof, plumbing, air conditioning systems, and electrical. Impact windows and doors further enhance comfort and security. From the moment you arrive, you'll be charmed by the inviting front porch, classic wood shutters, and quality craftsmanship throughout. Inside, the living room welcomes you with stunning vaulted ceilings and an airy, open feel. The thoughtfully designed floor plan flows seamlessly into the fully renovated kitchen, featuring an island, bar top with seating, quartz countertop, upgraded appliances, and abundant cabinetry. The first floor also offers a guest bedroom, a full bath, and a convenient laundry area. Upstairs, the primary suite provides a peaceful escape, complete with an ensuite bathroom, office nook, built-ins, and two closets for ample storage. Step outside to your private backyard oasis, where a composite deck and low-maintenance yard create the perfect setting for sunbathing, relaxing, or enjoying an al fresco meal. The location is unbeatable--just a short stroll to top-rated restaurants, the historic seaport, charming shops and boutiques, and world-famous Duval Street--yet quietly removed on a serene, private lane. Move right in and start enjoying the best of Key West living.

1120 Stump Ln, Key West

$1,130,000

Welcome to one of Key West's most inviting neighborhoods, where tree-lined streets and a true sense of community create the perfect backdrop for Island Living. From 1705 Von-Phister, you can bike to the beach in minutes, take the golf cart to downtown for dining and entertainment or simply relax at home in a quiet, family friendly setting. This property's elevation is at 6.5 Ft and has an assumable & affordable flood Insurance Policy of $1900 per year. One Level living with 3 spacious bedrooms, 2 of which are ensuite and all three have great closet space. Master bedroom features a double patio door leading out to the rear garden with private sun filled new deck area and ample space available for a pool; permitting currently in progress. All 3 bathrooms have been recently updated with new fixtures, floors and a stunning combination of Ceramic tile & quartz Stone. Exterior features two structures, one of which could be a pool cabana or work studio, already equipped with power. The second structure is smaller offers an excellent storage option. A generous side yard side offers a convenient entrance from your vehicle and additional storage of kayaks, paddleboards, bikes and scooters. Off street parking and large spacious front garden. A neighborhood gem that offers convenience and community - ready to be enjoyed from the moment you sign on the dotted Line. Being offered furnished to facilitate a stress-free move-in experience.

3 Beds ⋅ 3 Baths ⋅ 616522 MLS

Welcome to one of Key West's most inviting neighborhoods, where tree-lined streets and a true sense of community create the perfect backdrop for Island Living. From 1705 Von-Phister, you can bike to the beach in minutes, take the golf cart to downtown for dining and entertainment or simply relax at home in a quiet, family friendly setting. This property's elevation is at 6.5 Ft and has an assumable & affordable flood Insurance Policy of $1900 per year. One Level living with 3 spacious bedrooms, 2 of which are ensuite and all three have great closet space. Master bedroom features a double patio door leading out to the rear garden with private sun filled new deck area and ample space available for a pool; permitting currently in progress. All 3 bathrooms have been recently updated with new fixtures, floors and a stunning combination of Ceramic tile & quartz Stone. Exterior features two structures, one of which could be a pool cabana or work studio, already equipped with power. The second structure is smaller offers an excellent storage option. A generous side yard side offers a convenient entrance from your vehicle and additional storage of kayaks, paddleboards, bikes and scooters. Off street parking and large spacious front garden. A neighborhood gem that offers convenience and community - ready to be enjoyed from the moment you sign on the dotted Line. Being offered furnished to facilitate a stress-free move-in experience.

1705 Von Phister St, Key West

$1,125,000

Ocean Views! Over 2730 interior sq ft townhome with Ocean Views! This is the largest floor plan at SeaSide Court. Boasting 6 balconies - 4 bed - 4 bath - 3 levels over private garage. Only one other of these largest floor plans has come up for sell in the MLS in three years! Concrete construction with impact rated windows & doors gives you lock it & leave convenience. Features stainless steel kitchen appliances, two garden tubs & four showers. For your convenience it has trash and laundry chutes on multiple floors plus parking for three cars (one inside private garage, one in exclusive space outside the garage and one is in open parking around the pool). No attached unit on one side of this town home. On the ground level you have garage, interior storage, laundry room and covered area leading out to a secluded (fenced) courtyard. This is a great space for entertaining, dinning, bar area, etc... to enjoy our mild winter weather. Some owners in this community have built small, private pools in their court yards (this one does NOT have a private pool). Up on the roof you'll find a small, private roof top deck for enjoying sunrises, sunsets, star gazing or working on your tan! The SeaSide complex is gated, has two pools and a club house with weight / work out room. The private elevator goes from the ground level up to all three levels & has just been serviced. The roof-top deck is accessible from a 'ships ladder' only. Proof of funds or mortgage pre-qual required before showing and must accompany all offers. HOA fees cover wind insurance but not flood. See documents tab for Assoc docs, budget, etc...

4 Beds ⋅ 4 Baths ⋅ 617821 MLS

Ocean Views! Over 2730 interior sq ft townhome with Ocean Views! This is the largest floor plan at SeaSide Court. Boasting 6 balconies - 4 bed - 4 bath - 3 levels over private garage. Only one other of these largest floor plans has come up for sell in the MLS in three years! Concrete construction with impact rated windows & doors gives you lock it & leave convenience. Features stainless steel kitchen appliances, two garden tubs & four showers. For your convenience it has trash and laundry chutes on multiple floors plus parking for three cars (one inside private garage, one in exclusive space outside the garage and one is in open parking around the pool). No attached unit on one side of this town home. On the ground level you have garage, interior storage, laundry room and covered area leading out to a secluded (fenced) courtyard. This is a great space for entertaining, dinning, bar area, etc... to enjoy our mild winter weather. Some owners in this community have built small, private pools in their court yards (this one does NOT have a private pool). Up on the roof you'll find a small, private roof top deck for enjoying sunrises, sunsets, star gazing or working on your tan! The SeaSide complex is gated, has two pools and a club house with weight / work out room. The private elevator goes from the ground level up to all three levels & has just been serviced. The roof-top deck is accessible from a 'ships ladder' only. Proof of funds or mortgage pre-qual required before showing and must accompany all offers. HOA fees cover wind insurance but not flood. See documents tab for Assoc docs, budget, etc...

43 Seaside South Ct, Key West