bestfloridakeyshomefinder.com Search Results

Unique and extraordinary triple (3) lot property located in Old Town, Key West! Currently featuring a two-story home with 2 bedrooms and 2 bathrooms, and an in-ground pool. In addition, there is a detached studio/cottage, with each separately fenced from one another. On the third lot is a garage. Come and explore these three (3) contiguous, separate lots that all have the City of Key West's, Building Permit Allocation System (BPAS). Total lot SQ FT is 11,968. If you're seeking an opportunity to either build/renovate your future home, or a lucrative development opportunity, or simply to own one of Key West's most unique properties, look no further! It's time to make the move! Come to 1405/1409 United and see that it has the best of all the locations that Key West has to offer. Walking to all the amenities that Key West has, but far enough away from all the noise of the downtown. Plenty of room to make your own mark here. Location, Location, Location is this property. Call today for your private showing!

3 Beds ⋅ 3 Baths ⋅ 616089 MLS

Unique and extraordinary triple (3) lot property located in Old Town, Key West! Currently featuring a two-story home with 2 bedrooms and 2 bathrooms, and an in-ground pool. In addition, there is a detached studio/cottage, with each separately fenced from one another. On the third lot is a garage. Come and explore these three (3) contiguous, separate lots that all have the City of Key West's, Building Permit Allocation System (BPAS). Total lot SQ FT is 11,968. If you're seeking an opportunity to either build/renovate your future home, or a lucrative development opportunity, or simply to own one of Key West's most unique properties, look no further! It's time to make the move! Come to 1405/1409 United and see that it has the best of all the locations that Key West has to offer. Walking to all the amenities that Key West has, but far enough away from all the noise of the downtown. Plenty of room to make your own mark here. Location, Location, Location is this property. Call today for your private showing!

1405-1409 United St, Key West

$2,650,000

Build new in Old Town, steps from the Atlantic. 711 Waddell Street offers something Key West's Historic District seldom allows: the opportunity to remove the existing 1952 concrete block ranch and build a brand-new, fully code-compliant home in its place. Plans for the new residence are currently in the City of Key West approval process, with approvals anticipated prior to closing, so the new owner can move forward with construction without starting the process from the beginning. The proposed design is a classic two-story Conch-style residence with 3 bedrooms and 3 baths. It features a full-width front porch with a balcony above, metal roof, louvered shutters, and wood entry doors, combining historic character with modern construction. Inside, the living room opens directly to a private pool, with an open kitchen and dining area at the center of the home. A ground-floor guest suite and an upstairs primary suite with walk-in closet and balcony access complete the plan. Off-street parking is included. The location is exceptional. The home sits across the street from the Atlantic Ocean and Louie's Backyard, one of Key West's most celebrated waterfront restaurants, in a quiet residential pocket of the Historic District. Morning walks along the water, sunset dinners across the street, and an easy bike ride to Duval Street are all part of daily life here. New construction means current hurricane and flood standards, new systems throughout, and finishes selected to your own taste. Buyer to verify plans, approval status, and permit requirements with the City of Key West.

3 Beds ⋅ 2 Baths ⋅ 621713 MLS

Build new in Old Town, steps from the Atlantic. 711 Waddell Street offers something Key West's Historic District seldom allows: the opportunity to remove the existing 1952 concrete block ranch and build a brand-new, fully code-compliant home in its place. Plans for the new residence are currently in the City of Key West approval process, with approvals anticipated prior to closing, so the new owner can move forward with construction without starting the process from the beginning. The proposed design is a classic two-story Conch-style residence with 3 bedrooms and 3 baths. It features a full-width front porch with a balcony above, metal roof, louvered shutters, and wood entry doors, combining historic character with modern construction. Inside, the living room opens directly to a private pool, with an open kitchen and dining area at the center of the home. A ground-floor guest suite and an upstairs primary suite with walk-in closet and balcony access complete the plan. Off-street parking is included. The location is exceptional. The home sits across the street from the Atlantic Ocean and Louie's Backyard, one of Key West's most celebrated waterfront restaurants, in a quiet residential pocket of the Historic District. Morning walks along the water, sunset dinners across the street, and an easy bike ride to Duval Street are all part of daily life here. New construction means current hurricane and flood standards, new systems throughout, and finishes selected to your own taste. Buyer to verify plans, approval status, and permit requirements with the City of Key West.

711 Waddell Ave, Key West

$2,650,000

Life is BETTER at the Beach! Enjoy penthouse style living with panoramic ocean views from this two story oceanfront condo! This waterfront setting is simply serene, peaceful and beautiful! Floor to ceiling windows invite natural light, revealing the breathtaking water views from inside as well as the outdoor ocean facing deck - perfect for entertaining, lounging and absorbing sunrises. This private oasis also includes an updated kitchen and countertops, a primary bedroom suite on the first floor and a full guest suite on the second floor which includes double views! You'll be immediately captivated by this well rounded gated community which includes two pools, covered parking, a fitness center, sauna, and tennis court. Close to Smathers Beach, Higgs Beach, , the White Street Pier, the Wildlife Center the gallery district. Schedule your private viewing today - easy to show!

3 Beds ⋅ 2 Baths ⋅ 621379 MLS

Life is BETTER at the Beach! Enjoy penthouse style living with panoramic ocean views from this two story oceanfront condo! This waterfront setting is simply serene, peaceful and beautiful! Floor to ceiling windows invite natural light, revealing the breathtaking water views from inside as well as the outdoor ocean facing deck - perfect for entertaining, lounging and absorbing sunrises. This private oasis also includes an updated kitchen and countertops, a primary bedroom suite on the first floor and a full guest suite on the second floor which includes double views! You'll be immediately captivated by this well rounded gated community which includes two pools, covered parking, a fitness center, sauna, and tennis court. Close to Smathers Beach, Higgs Beach, , the White Street Pier, the Wildlife Center the gallery district. Schedule your private viewing today - easy to show!

1500 Atlantic Blvd Unit 414, Key West

$2,649,000

Welcome to your private tropical retreat in the heart of Key West! Located on a quiet lane, just one block from Duval Street and a short walk to the Southernmost Point, this beautiful three (3) bedroom, three (3) bathroom home offers the perfect combination of location, privacy, and comfortable island living. Built in 2002 and meticulously maintained, the home features a spacious open floor plan connecting the living room, dining area, kitchen, and stunning outdoor space making it perfect for both everyday living and entertaining family and friends. Beautiful hardwood floors run throughout the home, while the kitchen features granite countertops, stainless steel appliances, and custom cabinetry. Two sets of French doors lead from the dining/living space and offer views of the beautiful backyard pool area. Currently set up as a den/office, the first guest bedroom is on the first floor of the home. Upstairs, the spacious primary suite features a large en-suite bathroom and an impressive walk-in closet. A laundry/utility room is at the top of the stairway landing, and across the hallway is an additional guest bedroom with private en-suite bathroom. With three bedrooms and three full bathrooms, there is plenty of room for family and guests to enjoy their own space and privacy. The backyard is where you will truly appreciate the Key West lifestyle. Surrounded by mature tropical landscaping and fully fenced for privacy, the heated and chilled swimming pool is perfect for enjoying year-round. New Trex decking surrounds the pool, creating a wonderful outdoor space for dining, entertaining, or simply relaxing in the sunshine. This home offers everything you could want in a Key West property: a fantastic Old Town location with driveway parking, a great floor plan, beautiful outdoor living space, and the privacy of a quiet lane, all just steps from the excitement of Duval Street. Call today to schedule your private showing!

3 Beds ⋅ 3 Baths ⋅ 621735 MLS

Welcome to your private tropical retreat in the heart of Key West! Located on a quiet lane, just one block from Duval Street and a short walk to the Southernmost Point, this beautiful three (3) bedroom, three (3) bathroom home offers the perfect combination of location, privacy, and comfortable island living. Built in 2002 and meticulously maintained, the home features a spacious open floor plan connecting the living room, dining area, kitchen, and stunning outdoor space making it perfect for both everyday living and entertaining family and friends. Beautiful hardwood floors run throughout the home, while the kitchen features granite countertops, stainless steel appliances, and custom cabinetry. Two sets of French doors lead from the dining/living space and offer views of the beautiful backyard pool area. Currently set up as a den/office, the first guest bedroom is on the first floor of the home. Upstairs, the spacious primary suite features a large en-suite bathroom and an impressive walk-in closet. A laundry/utility room is at the top of the stairway landing, and across the hallway is an additional guest bedroom with private en-suite bathroom. With three bedrooms and three full bathrooms, there is plenty of room for family and guests to enjoy their own space and privacy. The backyard is where you will truly appreciate the Key West lifestyle. Surrounded by mature tropical landscaping and fully fenced for privacy, the heated and chilled swimming pool is perfect for enjoying year-round. New Trex decking surrounds the pool, creating a wonderful outdoor space for dining, entertaining, or simply relaxing in the sunshine. This home offers everything you could want in a Key West property: a fantastic Old Town location with driveway parking, a great floor plan, beautiful outdoor living space, and the privacy of a quiet lane, all just steps from the excitement of Duval Street. Call today to schedule your private showing!

410 Louisa St, Key West

$2,595,000

Traditional key West home impeccably maintained, boasts three bedrooms, three full baths with plenty of closets throughout the home. Large private lot with a heated pool featuring a waterfall. Nice size cabana room that has a/c and heat with ample closet space can be a fourth bedroom. This home has large rooms for entertaining, quaint front porch and off street parking. A true treasure.

3 Beds ⋅ 3 Baths ⋅ 613986 MLS

Traditional key West home impeccably maintained, boasts three bedrooms, three full baths with plenty of closets throughout the home. Large private lot with a heated pool featuring a waterfall. Nice size cabana room that has a/c and heat with ample closet space can be a fourth bedroom. This home has large rooms for entertaining, quaint front porch and off street parking. A true treasure.

508 Grinnell St, Key West

$2,549,000

**Seller Financing Considered** 2924 Riviera Dr is a Must See! Meticulously renovated house on the Riviera Canal. Features 3 bedrooms, 2 full baths & 2 half baths, plus separate pool / canal side cottage. Open & airy living room & kitchen gives you spectacular views of backyard, pool and canal. You can even see the pool and canal from the front door. Owner / Seller is a carpenter. House was stripped to the concrete block walls and rebuilt (with permits) with all new materials. New impact windows & doors, roof (with straps), ductless AC ( 2 compressors, 6 heads), electrical - 200 Amp service, water supply lines, manifold style on demand water heater, Turkish Marble floors throughout (no ceramic tile), drywall on walls & ceiling, kitchen cabinets & counter tops, appliances, bathroom fixtures, and much, much more. Even has interior laundry & utility room. Expansive primary bedroom with walk thru closet and spacious ensuite bath, plus pool & canal views. Enjoy the convenience of living in Key West and having your boat in your back yard. Concrete seawall (59Ft) with newer 12,000 Ibs boat lift and inground pool (with newer pump / filter) compliment the canal-front back yard. Lot is 7,670 sq ft. Located close to schools, professional offices, shopping, airport & beaches. Just a short ride to Duval St and the all the Old Town KW attractions. House is turn-key. Simply unpack your swimsuit and start enjoying the Keys lifestyle. **Seller is open to financing the Buyer**

3 Beds ⋅ 4 Baths ⋅ 618952 MLS

**Seller Financing Considered** 2924 Riviera Dr is a Must See! Meticulously renovated house on the Riviera Canal. Features 3 bedrooms, 2 full baths & 2 half baths, plus separate pool / canal side cottage. Open & airy living room & kitchen gives you spectacular views of backyard, pool and canal. You can even see the pool and canal from the front door. Owner / Seller is a carpenter. House was stripped to the concrete block walls and rebuilt (with permits) with all new materials. New impact windows & doors, roof (with straps), ductless AC ( 2 compressors, 6 heads), electrical - 200 Amp service, water supply lines, manifold style on demand water heater, Turkish Marble floors throughout (no ceramic tile), drywall on walls & ceiling, kitchen cabinets & counter tops, appliances, bathroom fixtures, and much, much more. Even has interior laundry & utility room. Expansive primary bedroom with walk thru closet and spacious ensuite bath, plus pool & canal views. Enjoy the convenience of living in Key West and having your boat in your back yard. Concrete seawall (59Ft) with newer 12,000 Ibs boat lift and inground pool (with newer pump / filter) compliment the canal-front back yard. Lot is 7,670 sq ft. Located close to schools, professional offices, shopping, airport & beaches. Just a short ride to Duval St and the all the Old Town KW attractions. House is turn-key. Simply unpack your swimsuit and start enjoying the Keys lifestyle. **Seller is open to financing the Buyer**

2924 Riviera Dr, Key West

$2,525,000

Set on a quiet, tree-lined block in one of Key West's most sought-after residential pockets, this thoughtfully reimagined 4BD/3BA residence offers just over 2,000 square feet of refined island living -- the result of a multi-year renovation where no detail was overlooked. The first floor opens to a flexible bedroom or private office alongside a full bath, newly converted and finished to the same standard as the rest of the home. Beyond, an all-new updated kitchen anchors the space with stainless appliances, custom built-in cabinetry, fresh countertops and designer lighting. French doors wrap the open living room, flooding the interior with natural light and dissolving the line between inside and out. Step through to your private tropical oasis: a heated pool, newly resurfaced and framed in travertine, with a new outdoor shower for rinsing off after a day at the beach. A setting built equally for quiet mornings and evenings. Upstairs, the primary suite delivers an ensuite bath, walk-in closet and a private balcony made for morning coffee above the palms. Two additional guest bedrooms and a full guest bath complete the second floor. Behind the finishes, the seller has invested in everything that matters: new HVAC, on-demand hot water, all-new pool equipment, new tile flooring, baseboards and lighting throughout, plus fresh interior and exterior paint. Renovated bathrooms and updated floors carry the same considered hand from room to room. A short bike ride delivers you to Key West's finest restaurants, beaches, galleries, museums and world-famous Duval Street -- yet the block itself stays wonderfully removed from it all. A neighborhood stunner not to be missed.

4 Beds ⋅ 3 Baths ⋅ 621162 MLS

Set on a quiet, tree-lined block in one of Key West's most sought-after residential pockets, this thoughtfully reimagined 4BD/3BA residence offers just over 2,000 square feet of refined island living -- the result of a multi-year renovation where no detail was overlooked. The first floor opens to a flexible bedroom or private office alongside a full bath, newly converted and finished to the same standard as the rest of the home. Beyond, an all-new updated kitchen anchors the space with stainless appliances, custom built-in cabinetry, fresh countertops and designer lighting. French doors wrap the open living room, flooding the interior with natural light and dissolving the line between inside and out. Step through to your private tropical oasis: a heated pool, newly resurfaced and framed in travertine, with a new outdoor shower for rinsing off after a day at the beach. A setting built equally for quiet mornings and evenings. Upstairs, the primary suite delivers an ensuite bath, walk-in closet and a private balcony made for morning coffee above the palms. Two additional guest bedrooms and a full guest bath complete the second floor. Behind the finishes, the seller has invested in everything that matters: new HVAC, on-demand hot water, all-new pool equipment, new tile flooring, baseboards and lighting throughout, plus fresh interior and exterior paint. Renovated bathrooms and updated floors carry the same considered hand from room to room. A short bike ride delivers you to Key West's finest restaurants, beaches, galleries, museums and world-famous Duval Street -- yet the block itself stays wonderfully removed from it all. A neighborhood stunner not to be missed.

1427 Washington St, Key West

$2,500,000

Discover an exceptional investment opportunity in the heart of the Florida Keys! Situated on a spacious lot just 3 minutes from the beach and world-famous Duval Street, this unique multi-unit property offers versatility, comfort, and island-style living at its finest. The main residence features 5 bedrooms and 3 bathrooms across 2,432 total s/f, designed for both relaxation and entertaining. Enjoy a private pool with pool heater, along with the convenience of two elevated A/C units, both less than 4 years old. The second unit offers 3 bedrooms and 1 bathroom with 1,504 total s/f of living space, plus a 2-car garage and its own elevated A/C unit, also less than 4 years old. Built for peace of mind and modern living, the property includes a durable metal roof, impact windows throughout, camera security system, preparation for an electric vehicle charger, and separate electric and water meters for each unit. Whether you're seeking a primary residence, vacation retreat, or income-producing property, this rare Florida Keys gem combines location, flexibility, and outstanding features in one incredible package.

8 Beds ⋅ 4 Baths ⋅ 619978 MLS

Discover an exceptional investment opportunity in the heart of the Florida Keys! Situated on a spacious lot just 3 minutes from the beach and world-famous Duval Street, this unique multi-unit property offers versatility, comfort, and island-style living at its finest. The main residence features 5 bedrooms and 3 bathrooms across 2,432 total s/f, designed for both relaxation and entertaining. Enjoy a private pool with pool heater, along with the convenience of two elevated A/C units, both less than 4 years old. The second unit offers 3 bedrooms and 1 bathroom with 1,504 total s/f of living space, plus a 2-car garage and its own elevated A/C unit, also less than 4 years old. Built for peace of mind and modern living, the property includes a durable metal roof, impact windows throughout, camera security system, preparation for an electric vehicle charger, and separate electric and water meters for each unit. Whether you're seeking a primary residence, vacation retreat, or income-producing property, this rare Florida Keys gem combines location, flexibility, and outstanding features in one incredible package.

1409 Whalton St, Key West

$2,499,000

Welcome to your Key West waterfront retreat. This 3bedroom 2bath home is featuring key upgrades already in place with a new roof, all new windows, updated electrical, fresh paint, and a beautiful brand new pool. Situated on an oversized 9,794 sq ft lot with room for your boat this home offers the ideal blend of comfort, outdoor living, and the flexibility to personalize over time. A rare opportunity to step into waterfront living in one of Key West's most desirable locations.

3 Beds ⋅ 2 Baths ⋅ 619667 MLS

Welcome to your Key West waterfront retreat. This 3bedroom 2bath home is featuring key upgrades already in place with a new roof, all new windows, updated electrical, fresh paint, and a beautiful brand new pool. Situated on an oversized 9,794 sq ft lot with room for your boat this home offers the ideal blend of comfort, outdoor living, and the flexibility to personalize over time. A rare opportunity to step into waterfront living in one of Key West's most desirable locations.

3612 Sunrise Dr, Key West

$2,490,000

**6%+ Cap Rate Opportunity ** Now offered at $2,490,000, this income producing Old Town property offers strong cash flow and immediate investor appeal. Located just steps from Duval Street, 402 Appelrouth Lane offers a rare investment opportunity in a premier X Flood Zone location. This mixed use property has income potential from residential and commercial units. With over 5000sqft of interior space this iconic structure showcases tall ceilings, historic architectural character and custom artistic details that give it Old Town Charm. Appelrouth Lane is known for strong foot traffic, established neighboring businesses and a desirable central location. just minutes from restaurants, galleries, shopping and Key West nightlife. Opportunities like this are exceptionally rare.

3 Beds ⋅ 8 Baths ⋅ 621784 MLS

**6%+ Cap Rate Opportunity ** Now offered at $2,490,000, this income producing Old Town property offers strong cash flow and immediate investor appeal. Located just steps from Duval Street, 402 Appelrouth Lane offers a rare investment opportunity in a premier X Flood Zone location. This mixed use property has income potential from residential and commercial units. With over 5000sqft of interior space this iconic structure showcases tall ceilings, historic architectural character and custom artistic details that give it Old Town Charm. Appelrouth Lane is known for strong foot traffic, established neighboring businesses and a desirable central location. just minutes from restaurants, galleries, shopping and Key West nightlife. Opportunities like this are exceptionally rare.

402 Applerouth Ln, Key West

$2,475,000

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

3 Beds ⋅ 2 Baths ⋅ 621462 MLS

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

1212 Olivia St, Key West

$2,434,000

Stunning modern home in New Town offering 2,525 sq. ft. of beautifully designed living space on an 8,250 sq. ft. lot. This 3-bedroom, 2 full + 2 half bath home features a desirable split floor plan with a private primary suite, complete with a walk-through closet and spa-like ensuite bath, plus two guest bedrooms and a full bath. The open-concept living, dining, and kitchen area is ideal for entertaining, highlighted by a 15-ft island and high-end Viking stainless steel appliances. The chef's kitchen also includes a wine cooler, ice maker, warming drawer, dual beverage drawers, and a dedicated coffee/wine station. Additional features include a walk-in pantry with drop-down desk, separate laundry room, and convenient half bath. Outdoor living is just as impressive, with French doors opening to a private backyard oasis featuring an Ipe wood deck, outdoor kitchen, outdoor shower, and an air-conditioned half bath. Enjoy the large heated pool and spa surrounded by lush landscaping. The property also offers a covered dual carport with built-in storage and additional brick parking for guests. Located just down the road from a public boat ramp and perfect for sunrise and sunset walks.

3 Beds ⋅ 4 Baths ⋅ 620092 MLS

Stunning modern home in New Town offering 2,525 sq. ft. of beautifully designed living space on an 8,250 sq. ft. lot. This 3-bedroom, 2 full + 2 half bath home features a desirable split floor plan with a private primary suite, complete with a walk-through closet and spa-like ensuite bath, plus two guest bedrooms and a full bath. The open-concept living, dining, and kitchen area is ideal for entertaining, highlighted by a 15-ft island and high-end Viking stainless steel appliances. The chef's kitchen also includes a wine cooler, ice maker, warming drawer, dual beverage drawers, and a dedicated coffee/wine station. Additional features include a walk-in pantry with drop-down desk, separate laundry room, and convenient half bath. Outdoor living is just as impressive, with French doors opening to a private backyard oasis featuring an Ipe wood deck, outdoor kitchen, outdoor shower, and an air-conditioned half bath. Enjoy the large heated pool and spa surrounded by lush landscaping. The property also offers a covered dual carport with built-in storage and additional brick parking for guests. Located just down the road from a public boat ramp and perfect for sunrise and sunset walks.

1511 17th Ter, Key West

$2,399,000

Welcome to 1320 Eliza Street, a beautiful historic Key West home filled with Old World charm and character. Once serving as a local schoolhouse, this unique property sits on a stunning, tropically landscaped corner lot in a quiet neighborhood, offering the perfect combination of history and privacy in Old Town, Key West. Featuring four (4) bedrooms, two (2) full bathrooms, and two (2) half bathrooms, this home offers plenty of space for family and guests, both indoors and out. A brand-new roof was recently installed, and the home has just been tented, providing added peace of mind. The main residence offers generous living spaces that open beautifully to the lush tropical gardens surrounding the home. The spacious living room flows directly onto a covered porch, allowing you to enjoy the wonderful Key West weather year-round. The chef's kitchen is perfect for preparing everything from a gourmet dinner to a casual meal with family and friends. The first-floor primary bedroom offers plenty of room for a king-size bed, along with a spacious walk-in closet. The second guest bedroom features its own en-suite bathroom and private front porch, giving guests their own special place to relax and enjoy the Key West lifestyle. Upstairs, you'll find a third bedroom along with an oversized walk-in storage area and ample closet space. Step outside and enjoy your own private tropical retreat. Beautiful gardens surround the heated and chilled swimming pool, creating a wonderful setting for entertaining or simply relaxing in the sunshine. Tucked away in the back corner of the property, the separate pool house offers additional privacy and flexibility, making it perfect for guests, a home office, or a quiet getaway. Complete with a half bathroom and outdoor shower, it offers what we like to call a true Key West bathroom! This home is a must see! Schedule your private showing today!

4 Beds ⋅ 4 Baths ⋅ 621742 MLS

Welcome to 1320 Eliza Street, a beautiful historic Key West home filled with Old World charm and character. Once serving as a local schoolhouse, this unique property sits on a stunning, tropically landscaped corner lot in a quiet neighborhood, offering the perfect combination of history and privacy in Old Town, Key West. Featuring four (4) bedrooms, two (2) full bathrooms, and two (2) half bathrooms, this home offers plenty of space for family and guests, both indoors and out. A brand-new roof was recently installed, and the home has just been tented, providing added peace of mind. The main residence offers generous living spaces that open beautifully to the lush tropical gardens surrounding the home. The spacious living room flows directly onto a covered porch, allowing you to enjoy the wonderful Key West weather year-round. The chef's kitchen is perfect for preparing everything from a gourmet dinner to a casual meal with family and friends. The first-floor primary bedroom offers plenty of room for a king-size bed, along with a spacious walk-in closet. The second guest bedroom features its own en-suite bathroom and private front porch, giving guests their own special place to relax and enjoy the Key West lifestyle. Upstairs, you'll find a third bedroom along with an oversized walk-in storage area and ample closet space. Step outside and enjoy your own private tropical retreat. Beautiful gardens surround the heated and chilled swimming pool, creating a wonderful setting for entertaining or simply relaxing in the sunshine. Tucked away in the back corner of the property, the separate pool house offers additional privacy and flexibility, making it perfect for guests, a home office, or a quiet getaway. Complete with a half bathroom and outdoor shower, it offers what we like to call a true Key West bathroom! This home is a must see! Schedule your private showing today!

1320 Eliza St, Key West

$2,399,000

Waterfront Home in Key West- 60 feet of water frontage, no homes across the canal and a fully gated lot, with your boat behind the house and downtown Key West minutes away. A wall of impact sliding glass doors opens the main living area to the screened patio, the newly renovated pool and the canal beyond. The kitchen has a large center island, premium cabinetry and a dining area that looks out over the pool to the water. Outside is set up for real use: an outdoor kitchen, an outdoor bathroom, shell stone limestone walkways and landscaped grounds. Three bedrooms, two of them en suite, and four full baths. A whole-home generator, two-zone air conditioning, a dedicated laundry room and covered parking. Canal control depth is approx. 3 feet, with approx. 12 feet of bridge clearance at low tide. Move-in ready. Call to see 3206 Riviera Drive in person.

3 Beds ⋅ 4 Baths ⋅ 620879 MLS

Waterfront Home in Key West- 60 feet of water frontage, no homes across the canal and a fully gated lot, with your boat behind the house and downtown Key West minutes away. A wall of impact sliding glass doors opens the main living area to the screened patio, the newly renovated pool and the canal beyond. The kitchen has a large center island, premium cabinetry and a dining area that looks out over the pool to the water. Outside is set up for real use: an outdoor kitchen, an outdoor bathroom, shell stone limestone walkways and landscaped grounds. Three bedrooms, two of them en suite, and four full baths. A whole-home generator, two-zone air conditioning, a dedicated laundry room and covered parking. Canal control depth is approx. 3 feet, with approx. 12 feet of bridge clearance at low tide. Move-in ready. Call to see 3206 Riviera Drive in person.

3206 Riviera Dr, Key West

$2,399,000

Discover a rare blend of history, artistry, and luxury in this extraordinary residence at the celebrated William Fleming House--one of Old Town Key West's most iconic and meticulously restored historic buildings. Originally constructed in the 1890s as Peacon's General Store, this architectural treasure has been transformed into an exclusive boutique condominium, exquisitely and entirely renovated. Inside, the first level condo rises to an unforgettable 16 feet, creating a sense of openness and serenity that feels both dramatic and inviting. Sunlight pours through impact-rated windows and doors, illuminating the vintage wood flooring and expansive walls that are ideal for showcasing meaningful art and personal collections. The thoughtfully designed layout includes two bedrooms, two full bathrooms, a half bath and a versatile loft space- accessed by a traditional staircase--offering remarkable flexibility for work, guests, creative pursuits, or quiet retreat. A private outdoor deck extends your living space and provides a peaceful spot for morning coffee or evening unwinding. The William Fleming House elevates daily living with its heated outdoor pool, lush tropical landscaping, and assigned off-street parking. Located in the desirable X-flood zone and directly across from Williams Hall, this residence places you in the heart of Old Town's cultural and architectural richness. With its unmatched scale, history, and character, this home invites you to bring your vision and transform it into a truly exceptional Key West sanctuary--one that reflects your style, your story, and your sense of place.

2 Beds ⋅ 3 Baths ⋅ 619742 MLS

Discover a rare blend of history, artistry, and luxury in this extraordinary residence at the celebrated William Fleming House--one of Old Town Key West's most iconic and meticulously restored historic buildings. Originally constructed in the 1890s as Peacon's General Store, this architectural treasure has been transformed into an exclusive boutique condominium, exquisitely and entirely renovated. Inside, the first level condo rises to an unforgettable 16 feet, creating a sense of openness and serenity that feels both dramatic and inviting. Sunlight pours through impact-rated windows and doors, illuminating the vintage wood flooring and expansive walls that are ideal for showcasing meaningful art and personal collections. The thoughtfully designed layout includes two bedrooms, two full bathrooms, a half bath and a versatile loft space- accessed by a traditional staircase--offering remarkable flexibility for work, guests, creative pursuits, or quiet retreat. A private outdoor deck extends your living space and provides a peaceful spot for morning coffee or evening unwinding. The William Fleming House elevates daily living with its heated outdoor pool, lush tropical landscaping, and assigned off-street parking. Located in the desirable X-flood zone and directly across from Williams Hall, this residence places you in the heart of Old Town's cultural and architectural richness. With its unmatched scale, history, and character, this home invites you to bring your vision and transform it into a truly exceptional Key West sanctuary--one that reflects your style, your story, and your sense of place.

800 Fleming St Unit Unit C1, Key West

$2,395,000

This Income Producing property with future rentals scheduled, 319 Grinnell Street is a captivating residence in the heart of Key West's Historic Seaport, where charm and character abound. This beautifully framed Key West-style home reflects the rich tapestry of the area's history, showcasing classic architecture with inviting porches and intricate details that honor the past. Nestled among a collection of historic homes, 319 Grinnell Street offers a serene escape while remaining close to the vibrant pulse of the seaport. The Historic Seaport is a treasure trove of maritime heritage, featuring streets lined with art galleries, eclectic shops, and gourmet dining options. This lively district, once the center of the island's shipping trade, now celebrates Key West's legacy through its well-preserved structures and vibrant community life. Owning 319 Grinnell Street means immersing yourself in a lifestyle rich with culture and history. Enjoy leisurely strolls along the quaint streets, where the scent of jasmine and the sounds of laughter fill the air. This home is not just a residence; it's an invitation to embrace the unique spirit of Key West, making it a perfect sanctuary for those who value both tradition and modern living. Experience the allure of 319 Grinnell Street, where historic charm meets contemporary comfort in the heart of the enchanting Historic Seaport. Professional Vacation Rental Management is available for this property. Call for a showing today.

3 Beds ⋅ 2 Baths ⋅ 618819 MLS

This Income Producing property with future rentals scheduled, 319 Grinnell Street is a captivating residence in the heart of Key West's Historic Seaport, where charm and character abound. This beautifully framed Key West-style home reflects the rich tapestry of the area's history, showcasing classic architecture with inviting porches and intricate details that honor the past. Nestled among a collection of historic homes, 319 Grinnell Street offers a serene escape while remaining close to the vibrant pulse of the seaport. The Historic Seaport is a treasure trove of maritime heritage, featuring streets lined with art galleries, eclectic shops, and gourmet dining options. This lively district, once the center of the island's shipping trade, now celebrates Key West's legacy through its well-preserved structures and vibrant community life. Owning 319 Grinnell Street means immersing yourself in a lifestyle rich with culture and history. Enjoy leisurely strolls along the quaint streets, where the scent of jasmine and the sounds of laughter fill the air. This home is not just a residence; it's an invitation to embrace the unique spirit of Key West, making it a perfect sanctuary for those who value both tradition and modern living. Experience the allure of 319 Grinnell Street, where historic charm meets contemporary comfort in the heart of the enchanting Historic Seaport. Professional Vacation Rental Management is available for this property. Call for a showing today.

319 Grinnell St, Key West

$2,380,000

Experience the ultimate Key West waterfront lifestyle with this private tropical retreat on the highly coveted Riviera Canal--one of the island's only canals offering direct boating access to world-class fishing and diving. Tucked behind a gated entrance, this beautifully landscaped property welcomes you into a lush, secluded garden setting that feels like your own hidden oasis in the heart of Key West. This meticulously maintained 3-bedroom, 2-bath ground-level pool home blends comfort, style, and functionality. Inside, you'll find elegant travertine flooring throughout, granite countertops, stainless steel appliances, and a wet bar--perfect for entertaining. The thoughtfully designed layout features two separate living areas, with both the main living space and the primary suite opening through hurricane-impact sliding glass doors to the backyard. Step outside to your private resort-style escape, where a stunning in-ground concrete pool overlooks the tranquil canal. Enjoy peaceful water views, frequent visits from manatees, and the natural privacy provided by protected mangroves across the water. The screened, covered lanai creates the perfect setting for outdoor dining and relaxation year-round. Boaters will appreciate the 15,000 lb boat lift, allowing you to go from home to open water in minutes. Additional premium features include a newer generator with large propane tanks, outdoor shower, electric gate, automated irrigation and landscape lighting, covered carport, and secure off-street parking for two vehicles. Located just minutes from Key West International Airport, dining, and local attractions, this exceptional property offers the perfect blend of convenience, privacy, and island luxury. Whether you're seeking a full-time residence or a vacation escape, this waterfront home is a rare opportunity to own a true piece of paradise.

3 Beds ⋅ 2 Baths ⋅ 619644 MLS

Experience the ultimate Key West waterfront lifestyle with this private tropical retreat on the highly coveted Riviera Canal--one of the island's only canals offering direct boating access to world-class fishing and diving. Tucked behind a gated entrance, this beautifully landscaped property welcomes you into a lush, secluded garden setting that feels like your own hidden oasis in the heart of Key West. This meticulously maintained 3-bedroom, 2-bath ground-level pool home blends comfort, style, and functionality. Inside, you'll find elegant travertine flooring throughout, granite countertops, stainless steel appliances, and a wet bar--perfect for entertaining. The thoughtfully designed layout features two separate living areas, with both the main living space and the primary suite opening through hurricane-impact sliding glass doors to the backyard. Step outside to your private resort-style escape, where a stunning in-ground concrete pool overlooks the tranquil canal. Enjoy peaceful water views, frequent visits from manatees, and the natural privacy provided by protected mangroves across the water. The screened, covered lanai creates the perfect setting for outdoor dining and relaxation year-round. Boaters will appreciate the 15,000 lb boat lift, allowing you to go from home to open water in minutes. Additional premium features include a newer generator with large propane tanks, outdoor shower, electric gate, automated irrigation and landscape lighting, covered carport, and secure off-street parking for two vehicles. Located just minutes from Key West International Airport, dining, and local attractions, this exceptional property offers the perfect blend of convenience, privacy, and island luxury. Whether you're seeking a full-time residence or a vacation escape, this waterfront home is a rare opportunity to own a true piece of paradise.

3108 Riviera Dr, Key West

$2,250,000

Prior to the development of Truman Annex which was a notable Naval base located in the center of Key West, now has many upscale homes and condos. This newly renovated 3-bedroom, 3-bathroom residence blends historic charm with cutting-edge contemporary design by interior designer David Smith. Step inside to soaring open ceilings with exposed ductwork and striking geometric lighting. Smart home technology is seamlessly integrated, allowing you to control the entire residence from your iPhone or iPad. Blackout and privacy illusion shades are installed throughout with impact windows and doors. The chef's kitchen is a true showpiece, featuring illuminated crystalline quartz countertops, an oversized island with under-counter lighting, and premium Miele appliances. A sleek induction cooktop with downdraft ventilation, walnut cabinetry with custom divider drawers, and 48'' x 48'' high-grade porcelain tile flooring complete the space. The primary suite offers ,a dramatic down-lit interlocking panel accent wall, a custom walk-in closet, and views of the historic Little White House. Spa-inspired bathrooms showcase porcelain walls, quartz sinks, smart toilets, and multi-head showers. The second en-suite bedroom features a private terrace, illuminated niche, and a luxurious walk-in shower. Every closet in the home is custom-designed and thoughtfully lit. Additional highlights include a fully furnished turnkey offering, oversized 8' doors, recessed window trims and baseboards, a large community pool, and one covered deeded parking space.

3 Beds ⋅ 3 Baths ⋅ 621771 MLS

Prior to the development of Truman Annex which was a notable Naval base located in the center of Key West, now has many upscale homes and condos. This newly renovated 3-bedroom, 3-bathroom residence blends historic charm with cutting-edge contemporary design by interior designer David Smith. Step inside to soaring open ceilings with exposed ductwork and striking geometric lighting. Smart home technology is seamlessly integrated, allowing you to control the entire residence from your iPhone or iPad. Blackout and privacy illusion shades are installed throughout with impact windows and doors. The chef's kitchen is a true showpiece, featuring illuminated crystalline quartz countertops, an oversized island with under-counter lighting, and premium Miele appliances. A sleek induction cooktop with downdraft ventilation, walnut cabinetry with custom divider drawers, and 48'' x 48'' high-grade porcelain tile flooring complete the space. The primary suite offers ,a dramatic down-lit interlocking panel accent wall, a custom walk-in closet, and views of the historic Little White House. Spa-inspired bathrooms showcase porcelain walls, quartz sinks, smart toilets, and multi-head showers. The second en-suite bedroom features a private terrace, illuminated niche, and a luxurious walk-in shower. Every closet in the home is custom-designed and thoughtfully lit. Additional highlights include a fully furnished turnkey offering, oversized 8' doors, recessed window trims and baseboards, a large community pool, and one covered deeded parking space.

115 Front St Unit APT 101, Key West

$2,250,000

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

5 Beds ⋅ 4 Baths ⋅ 621640 MLS

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

811 Olivia St, Key West

$2,250,000

If you are seeking a private tropical backyard oasis look no further. This charming 2 story home is situated on a corner parcel in a quiet and peaceful mid town neighborhood. Behind the white picket fence, you will be welcomed to a great room with dramatic ceiling heights, wrapped with sliding glass doorwalls that open to over 500 square feet of covered porches. This home has been very well maintained with several recent updates, including impact windows and doors, pool resurfacing, a new primary A/C unit, deck and interior paint and a charging station for an electric vehicle. A thoughtful floor plan great for entertaining, includes 3bd/3.5ba with the primary suite on the main level. Two additional bedrooms with ensuite baths are private to the upstairs. Built in just 1999 this home is an open palette awaiting your personal selection of cosmetic updates without the unknown obstacles of a historic home. The magic of this home lives in the sprawling backyard wrapped in mature tropical gardens with a large, heated saltwater pool. An excellent opportunity to personalize a well built home that caters to indoor/outdoor living ideal for the year round tropical climate!

3 Beds ⋅ 4 Baths ⋅ 621172 MLS

If you are seeking a private tropical backyard oasis look no further. This charming 2 story home is situated on a corner parcel in a quiet and peaceful mid town neighborhood. Behind the white picket fence, you will be welcomed to a great room with dramatic ceiling heights, wrapped with sliding glass doorwalls that open to over 500 square feet of covered porches. This home has been very well maintained with several recent updates, including impact windows and doors, pool resurfacing, a new primary A/C unit, deck and interior paint and a charging station for an electric vehicle. A thoughtful floor plan great for entertaining, includes 3bd/3.5ba with the primary suite on the main level. Two additional bedrooms with ensuite baths are private to the upstairs. Built in just 1999 this home is an open palette awaiting your personal selection of cosmetic updates without the unknown obstacles of a historic home. The magic of this home lives in the sprawling backyard wrapped in mature tropical gardens with a large, heated saltwater pool. An excellent opportunity to personalize a well built home that caters to indoor/outdoor living ideal for the year round tropical climate!

1300 Seminary St, Key West

$2,249,000

Some places in Key West you visit. This one you call home. 1104 Packer St is a storybook Conch cottage, full of surprises & charm. Inside, a grand foyer & tall ceilings welcome you in, and the home opens with a warmth that feels instantly familiar. Hardwood floors run throughout & original pulley windows nod to the island's history. Enjoy morning coffee or evening sundown from your own front porch. The open living & dining room is wrapped in windows framing your backyard oasis, with vaulted ceilings & natural light in every corner. French doors open to the pool, so gatherings flow easily from table to terrace. The large kitchen, with new Bosch appliances, Viking range & tons of storage, overlooks the pool & living/dining areas allowing the host to be part of the celebration. Step outside & the world softens. The new heated saltwater pool, installed 2026, shimmers beside travertine decking & an undercover porch/lanai, a private sanctuary for long afternoons & quiet evenings. When night falls & the island hushes, stretch out on a lounge chair & count the stars. The large ensuite primary bedroom is a true retreat, with a stunning new bath: two vanities, a classic clawfoot tub for long, quiet soaks & a spa-like shower. A third bedroom/office has a private entrance. Upstairs, a second guest bedroom offers an ensuite bath, & and private ensuite guest cottage keeps visitors comfortable & independent. Recent remodel includes new roof, AC, heated saltwater pool, tankless water heater, refreshed kitchen w/new appliances, & remodeled primary bath. Just arrive & exhale. This private home sits in a quiet, desired location, low risk flood zone only steps from Duval St, restaurants, entertainment & the beach. Old Conch soul, thoughtfully modern, ready to be yours. Come home to 1104 Packer St.

4 Beds ⋅ 4 Baths ⋅ 621864 MLS

Some places in Key West you visit. This one you call home. 1104 Packer St is a storybook Conch cottage, full of surprises & charm. Inside, a grand foyer & tall ceilings welcome you in, and the home opens with a warmth that feels instantly familiar. Hardwood floors run throughout & original pulley windows nod to the island's history. Enjoy morning coffee or evening sundown from your own front porch. The open living & dining room is wrapped in windows framing your backyard oasis, with vaulted ceilings & natural light in every corner. French doors open to the pool, so gatherings flow easily from table to terrace. The large kitchen, with new Bosch appliances, Viking range & tons of storage, overlooks the pool & living/dining areas allowing the host to be part of the celebration. Step outside & the world softens. The new heated saltwater pool, installed 2026, shimmers beside travertine decking & an undercover porch/lanai, a private sanctuary for long afternoons & quiet evenings. When night falls & the island hushes, stretch out on a lounge chair & count the stars. The large ensuite primary bedroom is a true retreat, with a stunning new bath: two vanities, a classic clawfoot tub for long, quiet soaks & a spa-like shower. A third bedroom/office has a private entrance. Upstairs, a second guest bedroom offers an ensuite bath, & and private ensuite guest cottage keeps visitors comfortable & independent. Recent remodel includes new roof, AC, heated saltwater pool, tankless water heater, refreshed kitchen w/new appliances, & remodeled primary bath. Just arrive & exhale. This private home sits in a quiet, desired location, low risk flood zone only steps from Duval St, restaurants, entertainment & the beach. Old Conch soul, thoughtfully modern, ready to be yours. Come home to 1104 Packer St.

1104 Packer St, Key West

$2,247,000

Prime Old Town Key West Location with Off Street Parking and 55 ft of Truman Avenue Frontage. The property currently consists of four licensed rental apartments; one 2BR/1BA unit and three 1BR/1BA units. Property formerly configured for two business offices. Perfect for your business downstairs and reside upstairs. Generous off-street parking; a rare and valuable feature in Old Town, enhances desirability for business and/or residential occupants. Lots of Options: long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with commercial use on the ground level and residential above. The flexible interior layout also offers the potential to be a duplex. Or reimagine as a spacious single-family residence. Conversion to four condos offers the highest investment return. This is an extremely well-located property with multiple use possibilities. Buyer to verify any conversion from existing use. Classic Conch-style construction with covered porches adds to the property's island appeal and long-term value.

5 Beds ⋅ 4 Baths ⋅ 619930 MLS

Prime Old Town Key West Location with Off Street Parking and 55 ft of Truman Avenue Frontage. The property currently consists of four licensed rental apartments; one 2BR/1BA unit and three 1BR/1BA units. Property formerly configured for two business offices. Perfect for your business downstairs and reside upstairs. Generous off-street parking; a rare and valuable feature in Old Town, enhances desirability for business and/or residential occupants. Lots of Options: long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with commercial use on the ground level and residential above. The flexible interior layout also offers the potential to be a duplex. Or reimagine as a spacious single-family residence. Conversion to four condos offers the highest investment return. This is an extremely well-located property with multiple use possibilities. Buyer to verify any conversion from existing use. Classic Conch-style construction with covered porches adds to the property's island appeal and long-term value.

1104 Truman Ave, Key West

$2,247,000

LOTS OF OPTIONS! Prime Old Town Key West Location with Off Street Parking. A variety of uses; long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with possible commercial use on the ground level and residential above. The flexible interior layout offers the potential to be a duplex or reimagined as a spacious single-family residence. Conversion to four condos offers the highest investment return. (Buyer to verify) Generous off-street parking; a rare and valuable feature in Old Town, enhances desirability for business and/or residential occupants. Classic Conch-style construction with covered porches adds to the property's island appeal and long-term value. The property currently consists of four apartments; one 2BR/1BA unit and three 1BR/1BA units, all licensed rentals.. This is an extremely well-located property with multiple use possibilities in a high-demand market.

5 Beds ⋅ 4 Baths ⋅ 619927 MLS

LOTS OF OPTIONS! Prime Old Town Key West Location with Off Street Parking. A variety of uses; long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with possible commercial use on the ground level and residential above. The flexible interior layout offers the potential to be a duplex or reimagined as a spacious single-family residence. Conversion to four condos offers the highest investment return. (Buyer to verify) Generous off-street parking; a rare and valuable feature in Old Town, enhances desirability for business and/or residential occupants. Classic Conch-style construction with covered porches adds to the property's island appeal and long-term value. The property currently consists of four apartments; one 2BR/1BA unit and three 1BR/1BA units, all licensed rentals.. This is an extremely well-located property with multiple use possibilities in a high-demand market.

1104 Truman Ave, Key West

$2,229,000

Welcome to 3801 Flagler Avenue in beautiful Key West! A stunning home designed for luxury, comfort, and privacy, offering the perfect indoor/outdoor island lifestyle. Situated on an oversized 9,500-square-foot lot, a rare find in Key West, this property features two separate structures, a spectacular two-tier saltwater pool with a tanning ledge and waterfall feature, and beautifully landscaped tropical grounds. The entire property feels like your own private resort. The main residence features one bedroom, one bathroom, a gourmet chef's kitchen, a spacious living area, and a beautiful second-floor loft. The open design and natural light give this home a peaceful, Zen-like feel. The second structure, located above the oversized two-car garage, provides the perfect accommodations for family and guests. Featuring two bedrooms, two bathrooms, and a generous living room, this separate living space offers exceptional comfort and privacy. Your guests will feel right at home while everyone enjoys their own personal space. Built for peace of mind and designed for effortless living, this newer-construction home offers exceptional features, including an elevated design above the FEMA AE-8 flood elevation, a whole-house generator, hurricane-impact windows and doors, and durable Hardi Board siding. Enjoy all the charm and beauty of Key West without the constant maintenance often associated with historic island homes. Step outside and discover your own tropical paradise. The beautifully landscaped grounds and stunning saltwater pool create a resort-style setting perfect for entertaining, unwinding or spending endless days soaking up the Florida Keys sunshine. Luxury, privacy, and convenience come together beautifully at 3801 Flagler Avenue. Owner is a licensed Florida Real Estate Broker. Call today to schedule your private showing!

3 Beds ⋅ 3 Baths ⋅ 621725 MLS

Welcome to 3801 Flagler Avenue in beautiful Key West! A stunning home designed for luxury, comfort, and privacy, offering the perfect indoor/outdoor island lifestyle. Situated on an oversized 9,500-square-foot lot, a rare find in Key West, this property features two separate structures, a spectacular two-tier saltwater pool with a tanning ledge and waterfall feature, and beautifully landscaped tropical grounds. The entire property feels like your own private resort. The main residence features one bedroom, one bathroom, a gourmet chef's kitchen, a spacious living area, and a beautiful second-floor loft. The open design and natural light give this home a peaceful, Zen-like feel. The second structure, located above the oversized two-car garage, provides the perfect accommodations for family and guests. Featuring two bedrooms, two bathrooms, and a generous living room, this separate living space offers exceptional comfort and privacy. Your guests will feel right at home while everyone enjoys their own personal space. Built for peace of mind and designed for effortless living, this newer-construction home offers exceptional features, including an elevated design above the FEMA AE-8 flood elevation, a whole-house generator, hurricane-impact windows and doors, and durable Hardi Board siding. Enjoy all the charm and beauty of Key West without the constant maintenance often associated with historic island homes. Step outside and discover your own tropical paradise. The beautifully landscaped grounds and stunning saltwater pool create a resort-style setting perfect for entertaining, unwinding or spending endless days soaking up the Florida Keys sunshine. Luxury, privacy, and convenience come together beautifully at 3801 Flagler Avenue. Owner is a licensed Florida Real Estate Broker. Call today to schedule your private showing!

3801 Flagler Ave, Key West

$2,199,000

Beyond the doors of 3821 Eagle Avenue, a private courtyard evokes the intimacy of a Tuscan retreat. Cascading vines, sculptural bougainvillea and lush greenery frame the 29x15 pool while a shaded terrace invites long lunches that linger into evening. Expansive folding glass doors connect the interiors to the outdoors allowing gatherings to flow naturally from kitchen to poolside. Warm wood cabinetry and a substantial waterfall edge island anchor a kitchen that knows culinary appointed with a Wolf induction range, Wolf hibachi grill, Double Fulgor Milano ovens and Hestan wine refrigeration. Generous surfaces invite abundant platters and conversation while the outdoor kitchen complete with a sink, two gas burners and a large Green Egg extends the experience into the garden. Large impact windows bring garden views into the bedrooms and living spaces keeping the surrounding greenery in sight throughout the home. The home balances open spaces for entertaining with the privacy of a personal escape. Its setting on Eagle Avenue, a beautiful wide street with sidewalks seldom found in Key West, completes a home with a distinctly Mediterranean sensibility and an unmistakable island soul.

3 Beds ⋅ 2 Baths ⋅ 621869 MLS

Beyond the doors of 3821 Eagle Avenue, a private courtyard evokes the intimacy of a Tuscan retreat. Cascading vines, sculptural bougainvillea and lush greenery frame the 29x15 pool while a shaded terrace invites long lunches that linger into evening. Expansive folding glass doors connect the interiors to the outdoors allowing gatherings to flow naturally from kitchen to poolside. Warm wood cabinetry and a substantial waterfall edge island anchor a kitchen that knows culinary appointed with a Wolf induction range, Wolf hibachi grill, Double Fulgor Milano ovens and Hestan wine refrigeration. Generous surfaces invite abundant platters and conversation while the outdoor kitchen complete with a sink, two gas burners and a large Green Egg extends the experience into the garden. Large impact windows bring garden views into the bedrooms and living spaces keeping the surrounding greenery in sight throughout the home. The home balances open spaces for entertaining with the privacy of a personal escape. Its setting on Eagle Avenue, a beautiful wide street with sidewalks seldom found in Key West, completes a home with a distinctly Mediterranean sensibility and an unmistakable island soul.

3821 Eagle Ave, Key West

$2,199,000

On a quiet lane in Old Town, this classic Conch home offers a setting where life feels just a little slower and a lot more enjoyable. From the moment you step inside, the home draws you outward, where indoor living blends naturally with the surrounding outdoor spaces. The heart of the home is built around entertaining. The living area, kitchen, and dining space come together in a way that encourages gathering, while the outdoor covered patio is perfect for dining or lounging creating a natural extension for everything from slow mornings to late evenings. Step outside and the pace shifts. Sitting on a large L shaped lot, the pool becomes the centerpiece, surrounded by deck space, greenery, and just enough privacy to make it feel like your own little corner of the island. The inviting primary suite is a peaceful retreat, featuring vaulted ceilings and French doors that open directly to the pool. Upstairs, two additional bedrooms and a shared bath provide comfortable separation, while the detached poolside cottage, with its own bath and outdoor shower offers flexible space for guests, a workspace, or added privacy. A convenient powder room is also located just off the kitchen. Dade County pine walls, wood floors, and tall ceilings bring warmth and authenticity, giving the home a sense of history without ever feeling heavy. It is comfortable, inviting, and easy to live in, the kind of home that makes everyday moments feel just a little more special. Quiet, central, and layered with history, 1109 Stump Lane stands as one of Old Town's most compelling hidden opportunities, a rare chance to own a truly private retreat in the heart of Key West.

3 Beds ⋅ 4 Baths ⋅ 619404 MLS

On a quiet lane in Old Town, this classic Conch home offers a setting where life feels just a little slower and a lot more enjoyable. From the moment you step inside, the home draws you outward, where indoor living blends naturally with the surrounding outdoor spaces. The heart of the home is built around entertaining. The living area, kitchen, and dining space come together in a way that encourages gathering, while the outdoor covered patio is perfect for dining or lounging creating a natural extension for everything from slow mornings to late evenings. Step outside and the pace shifts. Sitting on a large L shaped lot, the pool becomes the centerpiece, surrounded by deck space, greenery, and just enough privacy to make it feel like your own little corner of the island. The inviting primary suite is a peaceful retreat, featuring vaulted ceilings and French doors that open directly to the pool. Upstairs, two additional bedrooms and a shared bath provide comfortable separation, while the detached poolside cottage, with its own bath and outdoor shower offers flexible space for guests, a workspace, or added privacy. A convenient powder room is also located just off the kitchen. Dade County pine walls, wood floors, and tall ceilings bring warmth and authenticity, giving the home a sense of history without ever feeling heavy. It is comfortable, inviting, and easy to live in, the kind of home that makes everyday moments feel just a little more special. Quiet, central, and layered with history, 1109 Stump Lane stands as one of Old Town's most compelling hidden opportunities, a rare chance to own a truly private retreat in the heart of Key West.

1109 Stump Ln, Key West

$2,195,000

This stunning 5-bedroom, 5-bathroom fortress of a home, completely reimagined and rebuilt in 2023, offers 3,062 sq. ft. of luxurious living space on a 5,040 sq. ft. lot. Featuring 9-foot ceilings, custom wood cabinetry, porcelain wood-look tile and luxury vinyl flooring, the home showcases exceptional craftsmanship throughout. The chef's kitchen is a true centerpiece, featuring an impressive 17-foot island with seating for eight, professional grade appliances, a 36-inch gas range with vented hood, and a wine refrigerator. The spacious primary suite features a walk-in closet and a spa inspired wet room with dual showerheads, a clawfoot soaking tub, and dual vanities. Additional conveniences include laundry areas on both floors and abundant storage, including attic and under-home space. Built with durability and efficiency in mind, the home features impact resistant windows, spray foam insulation, and a double strapped aluminum standing seam roof. The backyard offers an inviting outdoor retreat, highlighted by a heated pool and traditional thatched chickee hut, perfect for relaxing or entertaining in true Key West style. From the moment you step inside, you'll appreciate the striking architectural symmetry, exquisite craftsmanship, and meticulous attention to detail that make this exceptional Key West residence truly one of a kind. *Please note that some photos have been digitally staged or altered*

5 Beds ⋅ 5 Baths ⋅ 621768 MLS

This stunning 5-bedroom, 5-bathroom fortress of a home, completely reimagined and rebuilt in 2023, offers 3,062 sq. ft. of luxurious living space on a 5,040 sq. ft. lot. Featuring 9-foot ceilings, custom wood cabinetry, porcelain wood-look tile and luxury vinyl flooring, the home showcases exceptional craftsmanship throughout. The chef's kitchen is a true centerpiece, featuring an impressive 17-foot island with seating for eight, professional grade appliances, a 36-inch gas range with vented hood, and a wine refrigerator. The spacious primary suite features a walk-in closet and a spa inspired wet room with dual showerheads, a clawfoot soaking tub, and dual vanities. Additional conveniences include laundry areas on both floors and abundant storage, including attic and under-home space. Built with durability and efficiency in mind, the home features impact resistant windows, spray foam insulation, and a double strapped aluminum standing seam roof. The backyard offers an inviting outdoor retreat, highlighted by a heated pool and traditional thatched chickee hut, perfect for relaxing or entertaining in true Key West style. From the moment you step inside, you'll appreciate the striking architectural symmetry, exquisite craftsmanship, and meticulous attention to detail that make this exceptional Key West residence truly one of a kind. *Please note that some photos have been digitally staged or altered*

2827 Harris Ave, Key West

$2,190,000

Discover island living at this spacious two-story, 5-bedroom, 4-bathroom retreat nestled in a quiet residential neighborhood right in the heart of Key West. Perfectly positioned this inviting property offers easy access to the beaches, tennis and pickleball courts, bocce courts, and the local dog park. Enjoy a leisurely bike ride to the vibrant energy of downtown Key West and Duval Street, then return home to your own private tropical escape. Inside, an open and welcoming floor plan features beautiful gray-blue tile flooring, a stylish kitchen, and generous living and dining areas designed for gathering with family and friends. With room to accommodate up to 14 people, the home offers exceptional flexibility for a large family, visiting guests, or those seeking a second home with income potential. The upper level provides two additional rooms, ideal for extra sleeping space, a home office, or a relaxing den. Step outside to a private backyard oasis featuring lush tropical landscaping, an expansive swimming pool, and a spacious deck perfect for outdoor dining, entertaining, and soaking up the Florida sunshine. A detached pool house adds another dimension of versatility, complete with a one-bedroom, one-bathroom studio and kitchenette--ideal for guests or additional living space. Offered fully furnished and with a history of vacation rental income, this property presents an exciting opportunity for investors seeking an income-producing asset or buyers looking to combine a personal island getaway with rental potential. Whether you envision a welcoming family retreat, a second home in paradise, or an investment in the Florida Keys lifestyle, 1519 Johnson Street offers space, flexibility, and a desirable central location to make it your own.

5 Beds ⋅ 4 Baths ⋅ 621798 MLS

Discover island living at this spacious two-story, 5-bedroom, 4-bathroom retreat nestled in a quiet residential neighborhood right in the heart of Key West. Perfectly positioned this inviting property offers easy access to the beaches, tennis and pickleball courts, bocce courts, and the local dog park. Enjoy a leisurely bike ride to the vibrant energy of downtown Key West and Duval Street, then return home to your own private tropical escape. Inside, an open and welcoming floor plan features beautiful gray-blue tile flooring, a stylish kitchen, and generous living and dining areas designed for gathering with family and friends. With room to accommodate up to 14 people, the home offers exceptional flexibility for a large family, visiting guests, or those seeking a second home with income potential. The upper level provides two additional rooms, ideal for extra sleeping space, a home office, or a relaxing den. Step outside to a private backyard oasis featuring lush tropical landscaping, an expansive swimming pool, and a spacious deck perfect for outdoor dining, entertaining, and soaking up the Florida sunshine. A detached pool house adds another dimension of versatility, complete with a one-bedroom, one-bathroom studio and kitchenette--ideal for guests or additional living space. Offered fully furnished and with a history of vacation rental income, this property presents an exciting opportunity for investors seeking an income-producing asset or buyers looking to combine a personal island getaway with rental potential. Whether you envision a welcoming family retreat, a second home in paradise, or an investment in the Florida Keys lifestyle, 1519 Johnson Street offers space, flexibility, and a desirable central location to make it your own.

1519 Johnson St, Key West

$2,150,000

Tucked away on a quiet private lane, this charming classic Key West cottage offers the perfect blend of historic character and modern comfort. Thoughtfully renovated, the home features a spacious, light-filled kitchen with updated finishes--ideal for entertaining or relaxed island living. The home works beautifully as a two-primary suite layout, with the flexibility to convert one suite into a third bedroom or private study. Step outside to your own tropical retreat, complete with a refreshing plunge pool surrounded by lush landscaping. Located in the heart of Old Town, you're just moments from dining, shops, and the vibrant local scene, yet enjoy the peace and privacy of a hidden setting. Additional highlights include off-street parking--a rare and valuable convenience in this sought-after neighborhood. Whether you're seeking a full-time residence, vacation home, or investment property, this cottage captures the essence of Key West living. Possible Seller financing. .

3 Beds ⋅ 2 Baths ⋅ 619599 MLS

Tucked away on a quiet private lane, this charming classic Key West cottage offers the perfect blend of historic character and modern comfort. Thoughtfully renovated, the home features a spacious, light-filled kitchen with updated finishes--ideal for entertaining or relaxed island living. The home works beautifully as a two-primary suite layout, with the flexibility to convert one suite into a third bedroom or private study. Step outside to your own tropical retreat, complete with a refreshing plunge pool surrounded by lush landscaping. Located in the heart of Old Town, you're just moments from dining, shops, and the vibrant local scene, yet enjoy the peace and privacy of a hidden setting. Additional highlights include off-street parking--a rare and valuable convenience in this sought-after neighborhood. Whether you're seeking a full-time residence, vacation home, or investment property, this cottage captures the essence of Key West living. Possible Seller financing. .

810 Carey Ln, Key West

$2,150,000

This fully renovated canal front home at 1724 Bahama Drive offers modern waterfront living in a highly convenient location in Key West. The property features four bedrooms and four bathrooms and includes a separate mother in law unit, making it well suited for guests, extended family, or flexible use. The home has been completely updated with a new kitchen featuring quartz countertops, custom cabinetry, and stainless steel Thermador appliances. New tile flooring, updated lighting, and fully renovated bathrooms with clean modern finishes create a bright and comfortable interior throughout. The home also includes a new central air conditioning system and discreet security cameras that blend seamlessly into the design. A new roof adds peace of mind and makes this a true move in ready property. Outside, the home offers 56 feet of concrete seawall along a calm canal, providing excellent dockage potential and easy access for boating and paddleboarding. The outdoor space includes a bar and grilling area that is ideal for entertaining, along with a fully fenced yard finished with low maintenance turf for privacy and ease of care. The location is one of the home's strongest features. It is close to schools and the local high school and is within five minutes of grocery stores, restaurants, and beaches. Downtown Key West is approximately ten minutes away, offering quick access to Old Town, shopping, dining, and entertainment. This is a rare opportunity to own a fully renovated canal front home with flexible living space, boat ready frontage, and a central Key West location. One of the owners is a Licensed Florida Realtor.

4 Beds ⋅ 4 Baths ⋅ 618256 MLS

This fully renovated canal front home at 1724 Bahama Drive offers modern waterfront living in a highly convenient location in Key West. The property features four bedrooms and four bathrooms and includes a separate mother in law unit, making it well suited for guests, extended family, or flexible use. The home has been completely updated with a new kitchen featuring quartz countertops, custom cabinetry, and stainless steel Thermador appliances. New tile flooring, updated lighting, and fully renovated bathrooms with clean modern finishes create a bright and comfortable interior throughout. The home also includes a new central air conditioning system and discreet security cameras that blend seamlessly into the design. A new roof adds peace of mind and makes this a true move in ready property. Outside, the home offers 56 feet of concrete seawall along a calm canal, providing excellent dockage potential and easy access for boating and paddleboarding. The outdoor space includes a bar and grilling area that is ideal for entertaining, along with a fully fenced yard finished with low maintenance turf for privacy and ease of care. The location is one of the home's strongest features. It is close to schools and the local high school and is within five minutes of grocery stores, restaurants, and beaches. Downtown Key West is approximately ten minutes away, offering quick access to Old Town, shopping, dining, and entertainment. This is a rare opportunity to own a fully renovated canal front home with flexible living space, boat ready frontage, and a central Key West location. One of the owners is a Licensed Florida Realtor.

1724 Bahama Dr, Key West

How much is your home worth?

How much is your home worth?