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Welcome to your dream oasis, perfectly situated directly across from a beautiful park with rare dual-street accessibility. This exceptional property blends spacious design with incredible versatility, featuring a 3-bedroom, 3-bathroom main residence, a fully detached private guest cottage, and entrances from two different streets at the front and back. As you step into the main home, you are immediately greeted by soaring, high ceilings and abundant natural light that amplify the open and airy layout. The floor plan flows effortlessly into the outdoor living spaces, featuring beautifully crafted brick-layered patios--perfect for dining alfresco, entertaining guests, or simply enjoying the peaceful breeze. Security and convenience meet at the rear of the property, which boasts off-street gated parking accessed securely from the back street. The separate backyard cottage provides the ultimate flexibility, making it an ideal space for a private home office, an artist's studio. Combined with the serene park views right out your front door and premium dual-access convenience, this unique property offers the perfect balance of community connection and private retreat.

3 Beds ⋅ 3 Baths ⋅ 621643 MLS

Welcome to your dream oasis, perfectly situated directly across from a beautiful park with rare dual-street accessibility. This exceptional property blends spacious design with incredible versatility, featuring a 3-bedroom, 3-bathroom main residence, a fully detached private guest cottage, and entrances from two different streets at the front and back. As you step into the main home, you are immediately greeted by soaring, high ceilings and abundant natural light that amplify the open and airy layout. The floor plan flows effortlessly into the outdoor living spaces, featuring beautifully crafted brick-layered patios--perfect for dining alfresco, entertaining guests, or simply enjoying the peaceful breeze. Security and convenience meet at the rear of the property, which boasts off-street gated parking accessed securely from the back street. The separate backyard cottage provides the ultimate flexibility, making it an ideal space for a private home office, an artist's studio. Combined with the serene park views right out your front door and premium dual-access convenience, this unique property offers the perfect balance of community connection and private retreat.

5435 5th Ave, Key West

$1,400,000

644 William Street The property being sold is 644 William Street. The current property record/card reflects both 644 and 646 William Street, although the property being conveyed is 644 William Street. The structure at 644 William Street is a two-and-a-half-story home currently configured as a duplex and is in need of renovation. The first floor consists of two bedrooms and two bathrooms. The second floor contains two bedrooms and one bathroom. A stairwell provides access to the third floor, which is currently unfinished and is not completed or configured as living space. In its current condition, the property contains four bedrooms and three bathrooms of finished living area, with additional unfinished space on the third floor. The property is currently being used/configured as a duplex and will require renovation.

3 Beds ⋅ 2 Baths ⋅ 621406 MLS

644 William Street The property being sold is 644 William Street. The current property record/card reflects both 644 and 646 William Street, although the property being conveyed is 644 William Street. The structure at 644 William Street is a two-and-a-half-story home currently configured as a duplex and is in need of renovation. The first floor consists of two bedrooms and two bathrooms. The second floor contains two bedrooms and one bathroom. A stairwell provides access to the third floor, which is currently unfinished and is not completed or configured as living space. In its current condition, the property contains four bedrooms and three bathrooms of finished living area, with additional unfinished space on the third floor. The property is currently being used/configured as a duplex and will require renovation.

646 William St, Key West

$535,000

Priced to sell and one of the most affordable opportunities in the popular Key West Estates! 3316 Harriet Avenue is an excellent option for a first-time homebuyer, investor, or workforce housing, offering NO HOA fees, deeded parking, shed, screened in covered porch, air-conditioning, and a private fenced outdoor area complete with landscaping. Conveniently located in New Town near shopping, schools, recreation, and everything Key West has to offer! This property provides a rare opportunity to own in Key West at an approachable price point. Schedule a showing today!

2 Beds ⋅ 2 Baths ⋅ 621365 MLS

Priced to sell and one of the most affordable opportunities in the popular Key West Estates! 3316 Harriet Avenue is an excellent option for a first-time homebuyer, investor, or workforce housing, offering NO HOA fees, deeded parking, shed, screened in covered porch, air-conditioning, and a private fenced outdoor area complete with landscaping. Conveniently located in New Town near shopping, schools, recreation, and everything Key West has to offer! This property provides a rare opportunity to own in Key West at an approachable price point. Schedule a showing today!

3316 Harriet Ave, Key West

$999,000

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

3 Beds ⋅ 2 Baths ⋅ 620987 MLS

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

506 Grinnell St, Key West

$995,000

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

3 Beds ⋅ 3 Baths ⋅ 620923 MLS

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

2309 Patterson Ave, Key West

$4,750,000

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

7 Beds ⋅ 5 Baths ⋅ 620661 MLS

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

901 Eisenhower Dr, Key West

$895,000

This large home on an extra large 6300 sf corner lot is an excellent opportunity for a renovation project. The main home is just under 1600 sf and consists of 4 bedrooms and 2 bathrooms and there is also a good sized detached structure of almost 200 sf that could be turned in to, among other ideas, an extra bedroom, artist's studio or pool cabana. The home had the roof replaced in 2014 and has storm shutters. There are terrazzo floors. The extra large lot has sour orange, Spanish lime and banana trees, off street parking and plenty of room for a pool.

4 Beds ⋅ 2 Baths ⋅ 620315 MLS

This large home on an extra large 6300 sf corner lot is an excellent opportunity for a renovation project. The main home is just under 1600 sf and consists of 4 bedrooms and 2 bathrooms and there is also a good sized detached structure of almost 200 sf that could be turned in to, among other ideas, an extra bedroom, artist's studio or pool cabana. The home had the roof replaced in 2014 and has storm shutters. There are terrazzo floors. The extra large lot has sour orange, Spanish lime and banana trees, off street parking and plenty of room for a pool.

3746 Paula Ave, Key West

$825,000

Prime redevelopment opportunity in the coveted upper section of Eagle Avenue, now offered with owner financing. This legal duplex is situated on one of the most desirable blocks in Key West, within a well-established residential neighborhood, presenting a compelling opportunity for investors, builders, or end users looking to create value. The main house is ready for a full renovation, offering a blank canvas to reimagine, customize, or redevelop to maximize returns. A City of Key West build-back letter is already in place, preserving valuable redevelopment rights and helping to streamline the process. For those seeking a larger project, this property can be combined with the adjacent vacant, buildable lot at 3705 Eagle Avenue creating a unique opportunity for expansion or future development. Ideally located near schools, shopping, beaches, and just minutes from Old Town, this is a rare chance to invest, renovate, or rebuild in a premier Key West location.

2 Beds ⋅ 2 Baths ⋅ 619418 MLS

Prime redevelopment opportunity in the coveted upper section of Eagle Avenue, now offered with owner financing. This legal duplex is situated on one of the most desirable blocks in Key West, within a well-established residential neighborhood, presenting a compelling opportunity for investors, builders, or end users looking to create value. The main house is ready for a full renovation, offering a blank canvas to reimagine, customize, or redevelop to maximize returns. A City of Key West build-back letter is already in place, preserving valuable redevelopment rights and helping to streamline the process. For those seeking a larger project, this property can be combined with the adjacent vacant, buildable lot at 3705 Eagle Avenue creating a unique opportunity for expansion or future development. Ideally located near schools, shopping, beaches, and just minutes from Old Town, this is a rare chance to invest, renovate, or rebuild in a premier Key West location.

3711 Eagle Ave, Key West

$765,000

Location, Location, Location! A renovation project that will increase the value of your investment exponentially! This home is located between the Southernmost Point and the Hemingway House in the world-renowned City of Key West Florida. Besides the excellent location, this home has concrete fences, a concrete gated entry from Whitehead Street, a nice sized rear deck/patio, front sitting/garden area, side walkways and plenty of room to add your favorite things to the yard spaces. An outside shower finishes off the exterior, a Key West ''must''. The interior has the sought after Dade County Pine on the walls, extremely high ceilings, and a large loft where you can stand up at the center. This home has everything you may want in a renovation project, not too big, not too small, just bring your ideas, toolbox and a paint can. Let's get to work on this home before the rest of the world finds out about it! Easy to see.

2 Beds ⋅ 1 Baths ⋅ 611075 MLS

Location, Location, Location! A renovation project that will increase the value of your investment exponentially! This home is located between the Southernmost Point and the Hemingway House in the world-renowned City of Key West Florida. Besides the excellent location, this home has concrete fences, a concrete gated entry from Whitehead Street, a nice sized rear deck/patio, front sitting/garden area, side walkways and plenty of room to add your favorite things to the yard spaces. An outside shower finishes off the exterior, a Key West ''must''. The interior has the sought after Dade County Pine on the walls, extremely high ceilings, and a large loft where you can stand up at the center. This home has everything you may want in a renovation project, not too big, not too small, just bring your ideas, toolbox and a paint can. Let's get to work on this home before the rest of the world finds out about it! Easy to see.

1102 Whitehead St, Key West

$2,790,000

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

$899,000

Unique opportunity to renovate this historic Old Town eyebrow home on a quiet, one-way, block of Elizabeth Street. Situated on a 3038 Sq.ft. lot there is ample space for off-street parking, a pool and 5 bedrooms with a renovation. Please note that advanced notice is required to arrange showings.

3 Beds ⋅ 3 Baths ⋅ 618708 MLS

Unique opportunity to renovate this historic Old Town eyebrow home on a quiet, one-way, block of Elizabeth Street. Situated on a 3038 Sq.ft. lot there is ample space for off-street parking, a pool and 5 bedrooms with a renovation. Please note that advanced notice is required to arrange showings.

818 Elizabeth St Unit Front, Key West

$1,449,000

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

3 Beds ⋅ 3 Baths ⋅ 617589 MLS

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

1505 Johnson St, Key West

$1,775,000

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

4 Beds ⋅ 2 Baths ⋅ 618211 MLS

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

1115 Fleming St, Key West

$1,089,000

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

3 Beds ⋅ 1 Baths ⋅ 614442 MLS

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

719 Elizabeth St, Key West

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