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

3 Beds ⋅ 3 Baths ⋅ 620747 MLS

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

1019 Whitehead St, Key West

$199,000

Own your piece of paradise with Dolphin slip #6 at Sunset Marina, Key West! This deeded 30 foot boat slip is located in one of Key West's most desirable full service marinas, offering a protected harbor and quick access to both the Gulf and the Atlantic. This slip can accommodate vessels up to 35 feet, and includes dockside water and electric. It is located on the gated side of Sunset Marina, featuring floating concrete docks, access to the pool, hot tub, clubhouse, fish cleaning station, and ample secure parking spaces. It also includes a very desirable Versa dock floating boat lift, providing easy access to the boat and extra storage area. Available separately is the 2014 Sea Hunt center console fishing boat, offered at 49k. Whether you're searching for the perfect home port, a seasonal boating retreat, or a valuable waterfront investment, this slip offers exceptional convenience and amenities. Liveaboards are not permitted on this side of the marina.

620740 MLS

Own your piece of paradise with Dolphin slip #6 at Sunset Marina, Key West! This deeded 30 foot boat slip is located in one of Key West's most desirable full service marinas, offering a protected harbor and quick access to both the Gulf and the Atlantic. This slip can accommodate vessels up to 35 feet, and includes dockside water and electric. It is located on the gated side of Sunset Marina, featuring floating concrete docks, access to the pool, hot tub, clubhouse, fish cleaning station, and ample secure parking spaces. It also includes a very desirable Versa dock floating boat lift, providing easy access to the boat and extra storage area. Available separately is the 2014 Sea Hunt center console fishing boat, offered at 49k. Whether you're searching for the perfect home port, a seasonal boating retreat, or a valuable waterfront investment, this slip offers exceptional convenience and amenities. Liveaboards are not permitted on this side of the marina.

5555 College Rd Unit 6, Key West

$1,695,000

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

2 Beds ⋅ 2 Baths ⋅ 620684 MLS

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

907 Frances St, Key West

$4,750,000

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

7 Beds ⋅ 5 Baths ⋅ 620661 MLS

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

901 Eisenhower Dr, Key West

$375,000

2 BEDROOMS 2 BATHROOMS WITH BALCONY, GATED COMMUNITY, HUGE POOL, TENNIS COURT ,PLENTY OF PARKING AND WALKING DISTANCE OF SHOPPING, GROCERIES, RESTAURANTS AND MOVIE THEATRE.

2 Beds ⋅ 2 Baths ⋅ 620647 MLS

2 BEDROOMS 2 BATHROOMS WITH BALCONY, GATED COMMUNITY, HUGE POOL, TENNIS COURT ,PLENTY OF PARKING AND WALKING DISTANCE OF SHOPPING, GROCERIES, RESTAURANTS AND MOVIE THEATRE.

3312 N Northside Dr Unit 607, Key West

$1,139,000

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

3 Beds ⋅ 2 Baths ⋅ 620641 MLS

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

1708 South Street, Key West

$1,095,000

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

4 Beds ⋅ 5 Baths ⋅ 620612 MLS

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

1503 Atlantic Blvd, Key West

$1,575,000

Experience the best of Old Town Key West in this beautifully updated 3-bedroom, 2-bath home offering the ease of single-level living. Inside, you'll find hardwood floors, tall ceilings, French doors, stainless steel appliances, and an inviting open layout filled with natural light. Designed for the Key West lifestyle, the private backyard features a saltwater pool with heater and chiller, outdoor shower, lush tropical landscaping, spacious patio, and two dedicated off-street parking spaces. This property is turnkey, fully furnished and ready to enjoy from day one. Well maintained and tastefully updated, recent improvements include a new HVAC system, saltwater pool system, updated furnishings and termite tenting. Currently operating as a monthly vacation rental with an established rental history. Located in the center of Old Town just moments from Higgs Beach, Duval Street, the Historic Seaport, neighborhood cafés, restaurants and shopping. This property offers the privacy and feel of a single family home, it is part of an intimate two-unit condominium association with no shared common elements. Whether you're looking for a successful investment property, a full-time residence, or your own island getaway, this home checks every box. Schedule your private showing today to explore this Key West opportunity.

3 Beds ⋅ 2 Baths ⋅ 620577 MLS

Experience the best of Old Town Key West in this beautifully updated 3-bedroom, 2-bath home offering the ease of single-level living. Inside, you'll find hardwood floors, tall ceilings, French doors, stainless steel appliances, and an inviting open layout filled with natural light. Designed for the Key West lifestyle, the private backyard features a saltwater pool with heater and chiller, outdoor shower, lush tropical landscaping, spacious patio, and two dedicated off-street parking spaces. This property is turnkey, fully furnished and ready to enjoy from day one. Well maintained and tastefully updated, recent improvements include a new HVAC system, saltwater pool system, updated furnishings and termite tenting. Currently operating as a monthly vacation rental with an established rental history. Located in the center of Old Town just moments from Higgs Beach, Duval Street, the Historic Seaport, neighborhood cafés, restaurants and shopping. This property offers the privacy and feel of a single family home, it is part of an intimate two-unit condominium association with no shared common elements. Whether you're looking for a successful investment property, a full-time residence, or your own island getaway, this home checks every box. Schedule your private showing today to explore this Key West opportunity.

1005 Watson St Unit 1, Key West

$1,199,000

Welcome to Seaside Residences, one of Key West's most sought-after gated communities. This beautifully updated three-story townhome is one of the largest residences in the community, offering 2 bedrooms, 3.5 bathrooms, 1,824 square feet of thoughtfully designed living space, making it the second-largest property in Seaside Residences. A private elevator services all three levels, providing both comfort and convenience. Enjoy the best island living with three private balconies offering beautiful sunrise and sunset views, plus a private rooftop deck perfect for relaxing, entertaining, or soaking up the Florida sunshine. The ground level features a private garage, laundry area, half bath, and a spacious outdoor patio complete with a tranquil fountain and fire pit--an ideal space for gathering with family and friends. The second level offers a spacious primary suite with an ensuite bath featuring dual vanities and a large walk-in shower, while the guest bedroom enjoys its own private full bath. The top floor showcases an open-concept living, dining, and kitchen area filled with abundant natural light. The kitchen features rich wood cabinetry, granite countertops, stainless steel appliances, generous pantry space, and an ideal layout for both everyday living and entertaining. Recent upgrades include a new air conditioning system, new water heater, and impact-resistant windows and doors throughout, providing peace of mind, energy efficiency, and storm protection. Residents enjoy exceptional community amenities including a resort-style pool, fitness center, and the convenience of building insurance covered through the HOA. Ideally located just steps beaches, Old Town Key West, world-class dining, shopping, marinas, and local attractions, this property also allows short-term rentals, making it an outstanding opportunity as a full-time residence, luxurious vacation home, or exceptional income-producing investment.

2 Beds ⋅ 4 Baths ⋅ 620515 MLS

Welcome to Seaside Residences, one of Key West's most sought-after gated communities. This beautifully updated three-story townhome is one of the largest residences in the community, offering 2 bedrooms, 3.5 bathrooms, 1,824 square feet of thoughtfully designed living space, making it the second-largest property in Seaside Residences. A private elevator services all three levels, providing both comfort and convenience. Enjoy the best island living with three private balconies offering beautiful sunrise and sunset views, plus a private rooftop deck perfect for relaxing, entertaining, or soaking up the Florida sunshine. The ground level features a private garage, laundry area, half bath, and a spacious outdoor patio complete with a tranquil fountain and fire pit--an ideal space for gathering with family and friends. The second level offers a spacious primary suite with an ensuite bath featuring dual vanities and a large walk-in shower, while the guest bedroom enjoys its own private full bath. The top floor showcases an open-concept living, dining, and kitchen area filled with abundant natural light. The kitchen features rich wood cabinetry, granite countertops, stainless steel appliances, generous pantry space, and an ideal layout for both everyday living and entertaining. Recent upgrades include a new air conditioning system, new water heater, and impact-resistant windows and doors throughout, providing peace of mind, energy efficiency, and storm protection. Residents enjoy exceptional community amenities including a resort-style pool, fitness center, and the convenience of building insurance covered through the HOA. Ideally located just steps beaches, Old Town Key West, world-class dining, shopping, marinas, and local attractions, this property also allows short-term rentals, making it an outstanding opportunity as a full-time residence, luxurious vacation home, or exceptional income-producing investment.

33 Seaside S Ct, Key West

$849,000

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

3 Beds ⋅ 3 Baths ⋅ 620501 MLS

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

3712 Duck Ave, Key West

$1,825,000

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

2 Beds ⋅ 2 Baths ⋅ 620470 MLS

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

1115 South Street, Key West

$584,900

Updated home in a prime central Key West location! Perfect for a local buyer or as an affordable second home in a quieter part of town, this move-in-ready property offers comfort, convenience, and tropical charm. The home features two generously sized bedrooms, two full bathrooms, and is situated on a corner lot in New Town. Warm wood flooring runs throughout, while the kitchen and dining area showcase Corian countertops, stainless steel appliances, classic wainscoting details, and a timeless neutral coastal palette that creates a bright, relaxed island atmosphere. French doors offer a bright and inviting living area and open to a composite deck and a lush, fully fenced yard, creating an ideal setting for indoor-outdoor living. Enjoy your morning coffee from the upstairs porch overlooking the tropical landscape, complete with a peek-a-boo view of the nearby park and recreational facilities. The private, gated yard is a true island retreat, featuring banana and mature mango trees that produce an abundance of fruit, vibrant bougainvillea, and an outdoor shower that's perfect after beach or boating days. Additional highlights include off-street parking, no HOA fees, and a welcoming townhome-style layout designed for easy living. Conveniently located near schools, shopping, beaches, grocery stores, sports fields, and movie theaters, this home offers the best of the Key West lifestyle, with everyday conveniences just a short walk or bike ride away.

2 Beds ⋅ 2 Baths ⋅ 620466 MLS

Updated home in a prime central Key West location! Perfect for a local buyer or as an affordable second home in a quieter part of town, this move-in-ready property offers comfort, convenience, and tropical charm. The home features two generously sized bedrooms, two full bathrooms, and is situated on a corner lot in New Town. Warm wood flooring runs throughout, while the kitchen and dining area showcase Corian countertops, stainless steel appliances, classic wainscoting details, and a timeless neutral coastal palette that creates a bright, relaxed island atmosphere. French doors offer a bright and inviting living area and open to a composite deck and a lush, fully fenced yard, creating an ideal setting for indoor-outdoor living. Enjoy your morning coffee from the upstairs porch overlooking the tropical landscape, complete with a peek-a-boo view of the nearby park and recreational facilities. The private, gated yard is a true island retreat, featuring banana and mature mango trees that produce an abundance of fruit, vibrant bougainvillea, and an outdoor shower that's perfect after beach or boating days. Additional highlights include off-street parking, no HOA fees, and a welcoming townhome-style layout designed for easy living. Conveniently located near schools, shopping, beaches, grocery stores, sports fields, and movie theaters, this home offers the best of the Key West lifestyle, with everyday conveniences just a short walk or bike ride away.

3201 Pearl Ave, Key West

$799,000

Duplex has 1,342 square feet of living space on a 2,841 square foot lot with 2 two bedroom one units generating $74,400.00 annually. Units have been recently renovated and ready for new tenants. Now offered separate from the vacant lot. Can also be purchased with lot at discounted price for both.

4 Beds ⋅ 2 Baths ⋅ 620461 MLS

Duplex has 1,342 square feet of living space on a 2,841 square foot lot with 2 two bedroom one units generating $74,400.00 annually. Units have been recently renovated and ready for new tenants. Now offered separate from the vacant lot. Can also be purchased with lot at discounted price for both.

1421-1425 2nd St, Key West

$979,000

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

4 Beds ⋅ 2 Baths ⋅ 620453 MLS

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

1500 5th St, Key West

$1,385,000

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

3 Beds ⋅ 2 Baths ⋅ 620448 MLS

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

2313 Fogarty Ave, Key West

$749,000

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

3 Beds ⋅ 2 Baths ⋅ 620436 MLS

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

2005 Fogarty Ave, Key West

$889,000

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

3 Beds ⋅ 2 Baths ⋅ 620435 MLS

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

2317 Fogarty Ave, Key West

$3,500,000

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

5 Beds ⋅ 5 Baths ⋅ 620434 MLS

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

416 Fleming St, Key West

$799,000

Welcome to this charming 2-bedroom, 2-bath Conch house offering 1,216 sq. ft. of comfortable living space in one of Key West's most convenient locations. The home is filled with warmth and character, highlighted by vaulted wood ceilings with exposed beams that create an inviting coastal atmosphere. Natural light pours through the impact windows and full wall of sliding glass doors, while the thoughtful floor plan provides comfortable areas for both everyday living and entertaining. The well-appointed kitchen offers ample cabinetry, generous counter space and bar seating that creates a natural gathering place for family and guests. A dedicated laundry area adds every day convenience, while the home's open and functional layout enhances its comfortable coastal appeal. An inviting Florida Room extends the living area and serves as the perfect connection to the private backyard retreat. Step outside to discover your own massive fenced-in backyard designed for relaxation, featuring lush landscaping, a hot tub and plenty of entertaining space. Centrally located in New Town, you'll enjoy easy access to beaches, shopping, restaurants, schools, and all the attractions that make island living so desirable. Whether you're looking for a full-time residence, seasonal escape, or island investment, this Key West home offers comfort, character and an exceptional location.

2 Beds ⋅ 2 Baths ⋅ 620402 MLS

Welcome to this charming 2-bedroom, 2-bath Conch house offering 1,216 sq. ft. of comfortable living space in one of Key West's most convenient locations. The home is filled with warmth and character, highlighted by vaulted wood ceilings with exposed beams that create an inviting coastal atmosphere. Natural light pours through the impact windows and full wall of sliding glass doors, while the thoughtful floor plan provides comfortable areas for both everyday living and entertaining. The well-appointed kitchen offers ample cabinetry, generous counter space and bar seating that creates a natural gathering place for family and guests. A dedicated laundry area adds every day convenience, while the home's open and functional layout enhances its comfortable coastal appeal. An inviting Florida Room extends the living area and serves as the perfect connection to the private backyard retreat. Step outside to discover your own massive fenced-in backyard designed for relaxation, featuring lush landscaping, a hot tub and plenty of entertaining space. Centrally located in New Town, you'll enjoy easy access to beaches, shopping, restaurants, schools, and all the attractions that make island living so desirable. Whether you're looking for a full-time residence, seasonal escape, or island investment, this Key West home offers comfort, character and an exceptional location.

3715 Flagler Ave, Key West

$1,195,000

Tucked into the heart of Old Town Key West, this beautifully renovated duplex offers two distinct 1-bedroom, 1-bath residences, each finished with a refined European style kitchen. Clean lines, quality cabinetry, and thoughtful detailing give both sides a fresh, elevated feel while preserving the easygoing island character that makes Old Town so sought after. Each unit lives comfortably and independently, making this an ideal setup for an owner-occupant looking to offset costs, an investor seeking dual income streams, or a buyer wanting a flexible space for family and guests. Private yard space adds room to garden, relax, or entertain under the palms, a true rarity at this address.

2 Beds ⋅ 2 Baths ⋅ 620360 MLS

Tucked into the heart of Old Town Key West, this beautifully renovated duplex offers two distinct 1-bedroom, 1-bath residences, each finished with a refined European style kitchen. Clean lines, quality cabinetry, and thoughtful detailing give both sides a fresh, elevated feel while preserving the easygoing island character that makes Old Town so sought after. Each unit lives comfortably and independently, making this an ideal setup for an owner-occupant looking to offset costs, an investor seeking dual income streams, or a buyer wanting a flexible space for family and guests. Private yard space adds room to garden, relax, or entertain under the palms, a true rarity at this address.

1126 Grinnell St, Key West

$599,000

Inside the gates of Key West Golf Club -- the only gated golf course community on the island, with an 18-hole Rees Jones course, two pools, a fitness center, and 24-hour security. This pet-friendly, fully-fenced yard, 2-bedroom, 1.5-bathroom Key West townhome sits on a corner lot with on-street parking and guest parking, steps from the mail, pool, and gym. It lives bigger than most: tile through the first floor, sustainable and comfortable cork flooring upstairs, and a permitted balcony enclosure that adds space other units don't have. Covered front porch, two spacious screened porches, In-unit washer and dryer, plus dedicated storage. One owner since new, with a new roof, new A/C, updated kitchen and bathrooms, and full shutter coverage -- move-in ready. Thirty-day minimum rentals permitted. Minutes to the airport, Old Town, the beaches, restaurants, entertainment, and the marinas.

2 Beds ⋅ 2 Baths ⋅ 620312 MLS

Inside the gates of Key West Golf Club -- the only gated golf course community on the island, with an 18-hole Rees Jones course, two pools, a fitness center, and 24-hour security. This pet-friendly, fully-fenced yard, 2-bedroom, 1.5-bathroom Key West townhome sits on a corner lot with on-street parking and guest parking, steps from the mail, pool, and gym. It lives bigger than most: tile through the first floor, sustainable and comfortable cork flooring upstairs, and a permitted balcony enclosure that adds space other units don't have. Covered front porch, two spacious screened porches, In-unit washer and dryer, plus dedicated storage. One owner since new, with a new roof, new A/C, updated kitchen and bathrooms, and full shutter coverage -- move-in ready. Thirty-day minimum rentals permitted. Minutes to the airport, Old Town, the beaches, restaurants, entertainment, and the marinas.

1 Spoonbill Way, Key West

$2,800,000

High Income-Producing Transient Licensed Gem in the Heart of Old Town Key West! Rare opportunity to own a highly sought-after transient licensed vacation rental in one of Key West's most desirable Old Town locations. This charming 2-bedroom, 2-bath home also features a versatile bonus room, offering additional space for guests, a home office, or a creative retreat. Thoughtfully updated from top to bottom, the property boasts a new roof, A/C system, appliances, water heater, furniture, decking, pool and much more--providing a truly turnkey investment. A proven performer, this popular vacation rental enjoys strong occupancy, excellent reviews, and consistent income potential. ''Potter's Cottage'' a true Key West conch house, showcases artistic character and unique touches of the former owner who was a well known Key West potter, creating an authentic Key West experience that guests love. Outside, enjoy a beautifully refreshed salt water pool area, a covered lanai, an outdoor shower, new Trex decking, and inviting outdoor living spaces designed for relaxation and entertaining. The quaint front porch offers the perfect spot to unwind and soak in the vibrant neighborhood atmosphere. Ideally situated in the heart of Old Town, you're just steps from Duval Street, world-class dining, shopping, galleries, entertainment, and historic attractions. Leave the car behind--everything Key West has to offer is within easy walking or biking distance. Whether you're seeking a profitable investment, a personal island getaway, or the best of both worlds, this exceptional property delivers. A buyer can step into existing bookings and reputation on day one, proven 5.0 rating, 100 plus reviews and strong repeat bookings. Schedule your private showing today and discover this outstanding Key West opportunity.

2 Beds ⋅ 2 Baths ⋅ 620355 MLS

High Income-Producing Transient Licensed Gem in the Heart of Old Town Key West! Rare opportunity to own a highly sought-after transient licensed vacation rental in one of Key West's most desirable Old Town locations. This charming 2-bedroom, 2-bath home also features a versatile bonus room, offering additional space for guests, a home office, or a creative retreat. Thoughtfully updated from top to bottom, the property boasts a new roof, A/C system, appliances, water heater, furniture, decking, pool and much more--providing a truly turnkey investment. A proven performer, this popular vacation rental enjoys strong occupancy, excellent reviews, and consistent income potential. ''Potter's Cottage'' a true Key West conch house, showcases artistic character and unique touches of the former owner who was a well known Key West potter, creating an authentic Key West experience that guests love. Outside, enjoy a beautifully refreshed salt water pool area, a covered lanai, an outdoor shower, new Trex decking, and inviting outdoor living spaces designed for relaxation and entertaining. The quaint front porch offers the perfect spot to unwind and soak in the vibrant neighborhood atmosphere. Ideally situated in the heart of Old Town, you're just steps from Duval Street, world-class dining, shopping, galleries, entertainment, and historic attractions. Leave the car behind--everything Key West has to offer is within easy walking or biking distance. Whether you're seeking a profitable investment, a personal island getaway, or the best of both worlds, this exceptional property delivers. A buyer can step into existing bookings and reputation on day one, proven 5.0 rating, 100 plus reviews and strong repeat bookings. Schedule your private showing today and discover this outstanding Key West opportunity.

1009 Whitehead St, Key West

$3,800,000

First time offered in more than 25 years, this beloved Old Town address presents a rare opportunity to own a complete compound on one of Key West's most private and premier streets. Located in the desirable X flood zone, the property features three bedrooms, three baths, and off-street parking for two vehicles. Rich in character and timeless Key West architecture, the home showcases beautifully white-painted, Dade County pine floors and walls, crown molding, and an open-concept living space. Dramatic cathedral ceilings in the living and dining areas create an airy, expansive atmosphere filled with natural light. The main residence offers excellent storage with multiple closets, two spacious bedrooms each with a private en-suite bath, a dedicated library/office, and a separate utility room. True to classic indoor-outdoor island living, French doors open from nearly every room, leading to a private oasis designed for entertaining. The backyard features a private 26' x 11' heated pool accented by dual waterfalls, a gas fire pit, an outdoor shower, and an expansive patio surrounded by lush landscaping. Enjoy the large, comfortable covered porch, perfect for enjoying coffee and the morning paper or an afternoon nap. Guests will be delighted to stay in the detached cottage with ample closet space and a beautifully appointed bath finished with floor-to-ceiling glass tile. Thoughtfully designed, the bath offers dual access--one entrance from the bedroom and another directly from the patio--making it an ideal pool bath. Adding to the property's charm is a lighted turf area with an added surprise, perfect for large parties and room for the kids or pets to play. Relax on the front porch, currently separated from the back porch by a privacy wall. With a small extension, the home's original wraparound design can be fully restored. This extraordinary opportunity to own a classic period home in the heart of Old Town is not to be missed. Call today to schedule your private showing.

3 Beds ⋅ 3 Baths ⋅ 620343 MLS

First time offered in more than 25 years, this beloved Old Town address presents a rare opportunity to own a complete compound on one of Key West's most private and premier streets. Located in the desirable X flood zone, the property features three bedrooms, three baths, and off-street parking for two vehicles. Rich in character and timeless Key West architecture, the home showcases beautifully white-painted, Dade County pine floors and walls, crown molding, and an open-concept living space. Dramatic cathedral ceilings in the living and dining areas create an airy, expansive atmosphere filled with natural light. The main residence offers excellent storage with multiple closets, two spacious bedrooms each with a private en-suite bath, a dedicated library/office, and a separate utility room. True to classic indoor-outdoor island living, French doors open from nearly every room, leading to a private oasis designed for entertaining. The backyard features a private 26' x 11' heated pool accented by dual waterfalls, a gas fire pit, an outdoor shower, and an expansive patio surrounded by lush landscaping. Enjoy the large, comfortable covered porch, perfect for enjoying coffee and the morning paper or an afternoon nap. Guests will be delighted to stay in the detached cottage with ample closet space and a beautifully appointed bath finished with floor-to-ceiling glass tile. Thoughtfully designed, the bath offers dual access--one entrance from the bedroom and another directly from the patio--making it an ideal pool bath. Adding to the property's charm is a lighted turf area with an added surprise, perfect for large parties and room for the kids or pets to play. Relax on the front porch, currently separated from the back porch by a privacy wall. With a small extension, the home's original wraparound design can be fully restored. This extraordinary opportunity to own a classic period home in the heart of Old Town is not to be missed. Call today to schedule your private showing.

619 Ashe St, 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

5555 College Rd Unit Dolphin 7, Key West

$225,000

Best wet slip deal in Key West for up to 35' x 15' boat. Gated secure marina community with Bellingham floating docks, plenty of parking, a clubhouse and pool. This slip keeps your boat out of the water and includes a $30,000 HARBOR HOIST BOAT LIFT. Immediately across marina is fuel dock and ship's store. Drive in and park your car, start up your boat and immediately enjoy ingress / egress to the Gulf of Mexico and the Atlantic Ocean. Liveaboard limited to 2 nights per week / max 7 nights per month.

620189 MLS

Best wet slip deal in Key West for up to 35' x 15' boat. Gated secure marina community with Bellingham floating docks, plenty of parking, a clubhouse and pool. This slip keeps your boat out of the water and includes a $30,000 HARBOR HOIST BOAT LIFT. Immediately across marina is fuel dock and ship's store. Drive in and park your car, start up your boat and immediately enjoy ingress / egress to the Gulf of Mexico and the Atlantic Ocean. Liveaboard limited to 2 nights per week / max 7 nights per month.

5555 College Rd Unit Dolphin 7, Key West

$3,495,000

Caroline Street, steps from the Historic Seaport. This is the Key West people picture before they ever get here. Built in the late 1800s as a cigar factory, when Key West was the cigar capital of the country. That origin is why it lives so much larger than the cottages around it: the volume, the ceiling height, the proportions of a working building rather than a bungalow. The Dade County pine is original, refinished rather than replaced, and irreplaceable. What 2023 changed was everything behind it -- raised to modern flood elevation, impact-rated windows and doors, and finishes chosen by a designer who wasn't in a hurry. Native coral walls, Jerusalem limestone, terrazzo, and marble under high ceilings. Out front, double balconies span the facade -- the real living room here. Coffee on the upper, cocktails on the lower, and Caroline Street putting on its show below: the walk to the Seaport, the whole slow parade of Old Town. Out back, collapsing glass doors open to the garden: a heated and chilled plunge pool with waterfall, walled and private -- the kind of courtyard that makes 4pm the best hour of the day. Four bedrooms, four en-suite baths, plus a guest half bath. The oversized upstairs primary has walk-in closets and a spa-caliber bath with double shower, artist-made cabinetry, and coral detail you won't see twice. A second primary on the main floor adds flexibility, plus a loft/office upstairs. The kitchen was built for how people actually entertain here: a six-seat island, full JennAir appliance package, open flow to the living and dining rooms. And it earns from day one. Six-figures in booked rental revenue transfers with the sale, repeat guests already on the calendar. Residence, winter escape, or income property -- it does all three. Sold furnished. No HOA. Seller financing possible. Three minutes to Duval. One minute to the shrimp boats. Homes on this block rarely trade, and almost never finished like this.

4 Beds ⋅ 5 Baths ⋅ 620222 MLS

Caroline Street, steps from the Historic Seaport. This is the Key West people picture before they ever get here. Built in the late 1800s as a cigar factory, when Key West was the cigar capital of the country. That origin is why it lives so much larger than the cottages around it: the volume, the ceiling height, the proportions of a working building rather than a bungalow. The Dade County pine is original, refinished rather than replaced, and irreplaceable. What 2023 changed was everything behind it -- raised to modern flood elevation, impact-rated windows and doors, and finishes chosen by a designer who wasn't in a hurry. Native coral walls, Jerusalem limestone, terrazzo, and marble under high ceilings. Out front, double balconies span the facade -- the real living room here. Coffee on the upper, cocktails on the lower, and Caroline Street putting on its show below: the walk to the Seaport, the whole slow parade of Old Town. Out back, collapsing glass doors open to the garden: a heated and chilled plunge pool with waterfall, walled and private -- the kind of courtyard that makes 4pm the best hour of the day. Four bedrooms, four en-suite baths, plus a guest half bath. The oversized upstairs primary has walk-in closets and a spa-caliber bath with double shower, artist-made cabinetry, and coral detail you won't see twice. A second primary on the main floor adds flexibility, plus a loft/office upstairs. The kitchen was built for how people actually entertain here: a six-seat island, full JennAir appliance package, open flow to the living and dining rooms. And it earns from day one. Six-figures in booked rental revenue transfers with the sale, repeat guests already on the calendar. Residence, winter escape, or income property -- it does all three. Sold furnished. No HOA. Seller financing possible. Three minutes to Duval. One minute to the shrimp boats. Homes on this block rarely trade, and almost never finished like this.

710 Caroline St, Key West

$1,799,765

Discover the perfect blend of island charm, comfort, and versality in this exceptional Key West property featuring a main residence and a spacious guest house. The main home offers 2 bed, and 2 baths thoughtfully designed with bright, open living space and classic Key West character. Added value is the separate guest house featuring an open concept floor plan, a beautiful bathroom, with open first floor bedroom, and an additional sleeping area on the second floor overlook that accommodates up to six guests. Perfect for the extended family/friends, or income producing opportunities, this flexible space offers endless possibilities. End your day with a relaxing swim in your inground 15x15 pool while looking at the stars.

3 Beds ⋅ 3 Baths ⋅ 620197 MLS

Discover the perfect blend of island charm, comfort, and versality in this exceptional Key West property featuring a main residence and a spacious guest house. The main home offers 2 bed, and 2 baths thoughtfully designed with bright, open living space and classic Key West character. Added value is the separate guest house featuring an open concept floor plan, a beautiful bathroom, with open first floor bedroom, and an additional sleeping area on the second floor overlook that accommodates up to six guests. Perfect for the extended family/friends, or income producing opportunities, this flexible space offers endless possibilities. End your day with a relaxing swim in your inground 15x15 pool while looking at the stars.

1523 Seminary St, Key West

$3,495,000

Stunning possibilities abound for this home on a double lot on the best street in the much sought after Casa Marina neighborhood in Key West. 1017 Washington Street is a renovation away from being your trophy property. The existing house has lots of room with 2,604 square feet of finished space with 4 bedrooms and 2.5 bathrooms. The oversized lot has even more room with 10, 724 square feet, a large swimming pool and an outdoor shed perfect for outdoor kitchen and living space. The property has never flooded and sits above flood. The possibilities are endless. Come see it today.

4 Beds ⋅ 3 Baths ⋅ 620188 MLS

Stunning possibilities abound for this home on a double lot on the best street in the much sought after Casa Marina neighborhood in Key West. 1017 Washington Street is a renovation away from being your trophy property. The existing house has lots of room with 2,604 square feet of finished space with 4 bedrooms and 2.5 bathrooms. The oversized lot has even more room with 10, 724 square feet, a large swimming pool and an outdoor shed perfect for outdoor kitchen and living space. The property has never flooded and sits above flood. The possibilities are endless. Come see it today.

1017 Washington St, Key West

$979,000

Wonderful Home with a Small Cottage, Salt Water Pool, and Off Street Parking, and 2 Brand New Roofs, on the Main House and the Guest Cottage!. Additionally- there is a New Insurance Mitigation report dated 8/28/2026! Affordable insurance premiums. Currently $13,367.48 a year for flood, windstorm, and homeowners insurance. The Main Home has an open living room with cathedral ceilings, and a loft . The Kitchen has French Doors leading to a large deck, and a private back fenced yard. Chicago brick surrounds the Salt Water Pool and cottage, with lots of additional space. There are plans by Serge with Artibus Designs for an addition added on to the home if desired giving an additional bedroom, bath, dining room, etc. Wonderful property as is or expand for more square footage!

2 Beds ⋅ 2 Baths ⋅ 620187 MLS

Wonderful Home with a Small Cottage, Salt Water Pool, and Off Street Parking, and 2 Brand New Roofs, on the Main House and the Guest Cottage!. Additionally- there is a New Insurance Mitigation report dated 8/28/2026! Affordable insurance premiums. Currently $13,367.48 a year for flood, windstorm, and homeowners insurance. The Main Home has an open living room with cathedral ceilings, and a loft . The Kitchen has French Doors leading to a large deck, and a private back fenced yard. Chicago brick surrounds the Salt Water Pool and cottage, with lots of additional space. There are plans by Serge with Artibus Designs for an addition added on to the home if desired giving an additional bedroom, bath, dining room, etc. Wonderful property as is or expand for more square footage!

3808 Duck Ave, Key West

$1,799,000

There is something special about a home where everything has already been done for you, and at 2101 Harris Avenue, all that is left is to move in and start enjoying it! Completely reimagined from top to bottom in 2025, this beautifully renovated Midtown East home feels fresh, welcoming, and ready for its next chapter. Set on a fully fenced corner lot with all new landscaping, the property offers both privacy and convenience, just minutes from schools, restaurants, shopping, and everything that makes Key West so special. Inside, sunlight fills the home through impact windows and doors, filling the home with a bright and airy feel. At the center of it all is a beautifully designed kitchen, where a large island with waterfall quartz counters comfortably seats 4 and naturally becomes the place where family and friends gather. From there, everything flows effortlessly outdoors. Large entertaining spaces connect beautifully to the covered rear porch and pool area, making the home feel bigger, brighter, and built for gathering. Whether it is dinner with friends, a lazy afternoon by the water, or simply enjoying the view from inside, the connection between indoor and outdoor living feels natural and easy. The heated pool, complete with a shallow sun shelf, becomes the centerpiece of the backyard, surrounded by generous space for lounging and outdoor dining. The 3 bedroom, 2.5 bathroom layout is equally inviting, highlighted by a spacious primary suite featuring a large walk in closet and private balcony. Beautifully renovated and thoughtfully designed, this is a home ready to be enjoyed from day one.

3 Beds ⋅ 3 Baths ⋅ 620176 MLS

There is something special about a home where everything has already been done for you, and at 2101 Harris Avenue, all that is left is to move in and start enjoying it! Completely reimagined from top to bottom in 2025, this beautifully renovated Midtown East home feels fresh, welcoming, and ready for its next chapter. Set on a fully fenced corner lot with all new landscaping, the property offers both privacy and convenience, just minutes from schools, restaurants, shopping, and everything that makes Key West so special. Inside, sunlight fills the home through impact windows and doors, filling the home with a bright and airy feel. At the center of it all is a beautifully designed kitchen, where a large island with waterfall quartz counters comfortably seats 4 and naturally becomes the place where family and friends gather. From there, everything flows effortlessly outdoors. Large entertaining spaces connect beautifully to the covered rear porch and pool area, making the home feel bigger, brighter, and built for gathering. Whether it is dinner with friends, a lazy afternoon by the water, or simply enjoying the view from inside, the connection between indoor and outdoor living feels natural and easy. The heated pool, complete with a shallow sun shelf, becomes the centerpiece of the backyard, surrounded by generous space for lounging and outdoor dining. The 3 bedroom, 2.5 bathroom layout is equally inviting, highlighted by a spacious primary suite featuring a large walk in closet and private balcony. Beautifully renovated and thoughtfully designed, this is a home ready to be enjoyed from day one.

2101 Harris Ave, Key West