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Up in the Treetops on Truman Avenue. Climb the white staircase, step onto your private retreat, and the street seems to disappear. This second-floor 1 bedroom, 1 bath condo at 1411 Truman Avenue sits in the tree canopy. Windows look out on green leaves and palm fronds, and the southern exposure brings in soft, steady light all day. It's turnkey and ready for the moment you arrive. Tasteful furnishings stay, and the finishes are done with care: wood-look tile floors throughout, a granite kitchen with stainless appliances, crown molding, plantation shutters, and ductless split AC. A stacked washer and dryer has its own closet, and the bedroom includes a walk-in closet with built-in storage. The condo fee covers all building insurance, including flood and wind, plus exterior maintenance and water. The location is The Meadows, one of Key West's most desirable neighborhoods. Duval Street is less than a mile away and the Historic Seaport is about a mile, so you can walk, bike, and leave the car parked. And the value is hard to beat: this is the lowest price per square foot of any 1 bedroom, 1 bath condo currently for sale in The Meadows and Old Town. Bring a toothbrush and your flip flops. Everything else is already here.

1 Beds ⋅ 1 Baths ⋅ 621903 MLS

Up in the Treetops on Truman Avenue. Climb the white staircase, step onto your private retreat, and the street seems to disappear. This second-floor 1 bedroom, 1 bath condo at 1411 Truman Avenue sits in the tree canopy. Windows look out on green leaves and palm fronds, and the southern exposure brings in soft, steady light all day. It's turnkey and ready for the moment you arrive. Tasteful furnishings stay, and the finishes are done with care: wood-look tile floors throughout, a granite kitchen with stainless appliances, crown molding, plantation shutters, and ductless split AC. A stacked washer and dryer has its own closet, and the bedroom includes a walk-in closet with built-in storage. The condo fee covers all building insurance, including flood and wind, plus exterior maintenance and water. The location is The Meadows, one of Key West's most desirable neighborhoods. Duval Street is less than a mile away and the Historic Seaport is about a mile, so you can walk, bike, and leave the car parked. And the value is hard to beat: this is the lowest price per square foot of any 1 bedroom, 1 bath condo currently for sale in The Meadows and Old Town. Bring a toothbrush and your flip flops. Everything else is already here.

1411 Truman Ave Unit 3, Key West

$1,100,000

NEW LISTING! This home, nestled in the sought-after Midtown West area, is just a few blocks away from pickleball and tennis courts, beautiful beaches, dining options, and parks. The features of this home include two bedrooms and two baths, with spacious living areas that offer lovely open spaces. The outdoor living area includes a covered deck that is perfect for al fresco dining, entertaining, or relaxing. The kitchen is equipped with a gas range and stainless steel appliances, leading to a large pantry with laundry. The living room includes built-ins for added convenience, and the family room opens up to outdoor areas, enhancing the flow of space. There is room to add a pool. The home also boasts impact-rated windows and doors, central air conditioning, a shed, a fenced yard for privacy and parking!

2 Beds ⋅ 2 Baths ⋅ 621900 MLS

NEW LISTING! This home, nestled in the sought-after Midtown West area, is just a few blocks away from pickleball and tennis courts, beautiful beaches, dining options, and parks. The features of this home include two bedrooms and two baths, with spacious living areas that offer lovely open spaces. The outdoor living area includes a covered deck that is perfect for al fresco dining, entertaining, or relaxing. The kitchen is equipped with a gas range and stainless steel appliances, leading to a large pantry with laundry. The living room includes built-ins for added convenience, and the family room opens up to outdoor areas, enhancing the flow of space. There is room to add a pool. The home also boasts impact-rated windows and doors, central air conditioning, a shed, a fenced yard for privacy and parking!

1513 Washington St, Key West

$5,365,000

Discover The Victoria House, a distinctive historic Key West residence with a transient license where timeless architectural charm meets the relaxed elegance of island living. Offered furnished at $5,365,000, this remarkable property at 806 Truman Avenue features five bedrooms, five full bathrooms, and two half bathrooms across the main residence and private pool house. Classic Victorian-inspired architecture, inviting covered porches, beautiful wood floors, vaulted beadboard ceilings, and lush tropical landscaping create an atmosphere of warmth and sophistication. Thoughtfully arranged across three levels, the main residence features two second-floor primary suites with king beds, en-suite bathrooms, and direct access to private outdoor spaces. The third floor offers a queen bedroom, a spacious two-queen bedroom suite, and a charming loft sitting area. The separate pool house provides additional privacy with a king bedroom, en-suite full bathroom, and direct access to the spectacular pool courtyard. Designed for effortless indoor-outdoor living, the tropical courtyard features a private swimming pool, spa, expansive sun decks, covered outdoor dining, upper-level balconies, and a distinctive spiral staircase. Mature palms, brick walkways, and classic white picket fencing enhance the property's unmistakable Key West character. Whether entertaining guests, relaxing beside the pool, or enjoying a quiet morning on the covered front porch, The Victoria House offers an exceptional opportunity to experience the beauty, character, and lifestyle of historic Key West. Offered furnished for a seamless transition to island living.

5 Beds ⋅ 6 Baths ⋅ 621899 MLS

Discover The Victoria House, a distinctive historic Key West residence with a transient license where timeless architectural charm meets the relaxed elegance of island living. Offered furnished at $5,365,000, this remarkable property at 806 Truman Avenue features five bedrooms, five full bathrooms, and two half bathrooms across the main residence and private pool house. Classic Victorian-inspired architecture, inviting covered porches, beautiful wood floors, vaulted beadboard ceilings, and lush tropical landscaping create an atmosphere of warmth and sophistication. Thoughtfully arranged across three levels, the main residence features two second-floor primary suites with king beds, en-suite bathrooms, and direct access to private outdoor spaces. The third floor offers a queen bedroom, a spacious two-queen bedroom suite, and a charming loft sitting area. The separate pool house provides additional privacy with a king bedroom, en-suite full bathroom, and direct access to the spectacular pool courtyard. Designed for effortless indoor-outdoor living, the tropical courtyard features a private swimming pool, spa, expansive sun decks, covered outdoor dining, upper-level balconies, and a distinctive spiral staircase. Mature palms, brick walkways, and classic white picket fencing enhance the property's unmistakable Key West character. Whether entertaining guests, relaxing beside the pool, or enjoying a quiet morning on the covered front porch, The Victoria House offers an exceptional opportunity to experience the beauty, character, and lifestyle of historic Key West. Offered furnished for a seamless transition to island living.

806 Truman Ave, Key West

$1,150,000

Welcome to 1025 Elgin Lane, an exquisite residence nestled in Key West's Historic Seaport District. This recently updated home seamlessly blends historic charm with modern comforts, offering an unparalleled living experience in one of Florida's most sought-after locales. The interiors are adorned with original Dade County Pine walls and flooring, exuding warmth and character that pay homage to the home's rich heritage. Recent enhancements have elevated the home's functionality and aesthetic appeal, including a new foundation, beautiful new flooring, tastefully updated bathrooms, and fresh paint inside and outside. The home features high ceilings with exposed beams and French doors that open to a private patio, perfect for morning coffee, alfresco dining, or evening gatherings under the stars. The second-floor primary suite offers a private sanctuary, complete with a walk-in closet and an en-suite bathroom featuring a classic clawfoot tub. The downstairs bedroom is generously sized and includes a walk-in closet. The front porch offers a peaceful spot to enjoy the tranquility of Elgin Lane, where minimal traffic enhances the sense of privacy. A designated off-street parking space adds to the convenience of this property. A private walkway provides direct access to Eaton Street, placing local bakeries, shops, and entertainment just steps away. Situated less than a block from the renowned Old Town Bakery and just two blocks from the lively Seaport, the home offers easy access to some of Key West's finest dining, shopping, and attractions. Whether you're seeking a serene personal retreat or a lucrative investment property, this residence offers an exceptional opportunity to own a piece of Key West's storied history.

2 Beds ⋅ 2 Baths ⋅ 621898 MLS

Welcome to 1025 Elgin Lane, an exquisite residence nestled in Key West's Historic Seaport District. This recently updated home seamlessly blends historic charm with modern comforts, offering an unparalleled living experience in one of Florida's most sought-after locales. The interiors are adorned with original Dade County Pine walls and flooring, exuding warmth and character that pay homage to the home's rich heritage. Recent enhancements have elevated the home's functionality and aesthetic appeal, including a new foundation, beautiful new flooring, tastefully updated bathrooms, and fresh paint inside and outside. The home features high ceilings with exposed beams and French doors that open to a private patio, perfect for morning coffee, alfresco dining, or evening gatherings under the stars. The second-floor primary suite offers a private sanctuary, complete with a walk-in closet and an en-suite bathroom featuring a classic clawfoot tub. The downstairs bedroom is generously sized and includes a walk-in closet. The front porch offers a peaceful spot to enjoy the tranquility of Elgin Lane, where minimal traffic enhances the sense of privacy. A designated off-street parking space adds to the convenience of this property. A private walkway provides direct access to Eaton Street, placing local bakeries, shops, and entertainment just steps away. Situated less than a block from the renowned Old Town Bakery and just two blocks from the lively Seaport, the home offers easy access to some of Key West's finest dining, shopping, and attractions. Whether you're seeking a serene personal retreat or a lucrative investment property, this residence offers an exceptional opportunity to own a piece of Key West's storied history.

1025 Elgin Ln, Key West

$350,000

Move-In Ready Island Living with Ocean Views at The Santa Clara Condominium in Key West! Discover your own slice of paradise at The Santa Clara Condominium in this beautifully renovated and furnished 1-bedroom, 1-bath residence, ideally situated on the 6th floor with stunning ocean views from your private balcony! Thoughtfully updated and tastefully furnished, this inviting residence features a beautifully renovated kitchen with stainless steel appliances, tile and laminate flooring, hurricane-resistant windows and doors, and a comfortable, functional layout. Step outside onto your private ocean-view balcony, where you can sip your morning coffee, unwind with your favorite evening beverage, and enjoy the refreshing island breezes. Embrace the best of resort-style living with an impressive array of community amenities, including a swimming pool, tennis court, secure building entry, on-site laundry facilities, plenty of parking, and well-maintained common areas. Extensive renovations were recently completed, and continued improvements enhance the community's appeal. Location, location, location! Nestled in the heart of Key West's desirable New Town neighborhood, The Santa Clara Condominium offers convenient access to fantastic restaurants, shopping, movie theater, sports complexes, beaches, medical facilities, schools, and the airport, and so much more. All the excitement of historic downtown Key West is just a short drive away. Whether you're a first-time homebuyer, savvy investor, seasonal resident, or simply searching for the perfect island getaway, this turnkey condo offers an exceptional combination of comfort, convenience, and tropical charm. Move right in, relax, and start enjoying the Key West lifestyle you've been dreaming of! Opportunities like this don't come along every day. Schedule your private showing today!

1 Beds ⋅ 1 Baths ⋅ 621897 MLS

Move-In Ready Island Living with Ocean Views at The Santa Clara Condominium in Key West! Discover your own slice of paradise at The Santa Clara Condominium in this beautifully renovated and furnished 1-bedroom, 1-bath residence, ideally situated on the 6th floor with stunning ocean views from your private balcony! Thoughtfully updated and tastefully furnished, this inviting residence features a beautifully renovated kitchen with stainless steel appliances, tile and laminate flooring, hurricane-resistant windows and doors, and a comfortable, functional layout. Step outside onto your private ocean-view balcony, where you can sip your morning coffee, unwind with your favorite evening beverage, and enjoy the refreshing island breezes. Embrace the best of resort-style living with an impressive array of community amenities, including a swimming pool, tennis court, secure building entry, on-site laundry facilities, plenty of parking, and well-maintained common areas. Extensive renovations were recently completed, and continued improvements enhance the community's appeal. Location, location, location! Nestled in the heart of Key West's desirable New Town neighborhood, The Santa Clara Condominium offers convenient access to fantastic restaurants, shopping, movie theater, sports complexes, beaches, medical facilities, schools, and the airport, and so much more. All the excitement of historic downtown Key West is just a short drive away. Whether you're a first-time homebuyer, savvy investor, seasonal resident, or simply searching for the perfect island getaway, this turnkey condo offers an exceptional combination of comfort, convenience, and tropical charm. Move right in, relax, and start enjoying the Key West lifestyle you've been dreaming of! Opportunities like this don't come along every day. Schedule your private showing today!

3312 Northside Dr Unit 605, Key West

$895,000

A Key West Antiquity. A fresh point of view. The story of 921 Angela Street reaches into Key West's cigar-making past. The address appears in the city's 1906 directory as the residence of cigar maker Claude Johnson--a connection to the craftsmen who helped shape the island. Today, Dade County pine walls and floors, high ceilings, and a front porch that participates in the neighborhood carry that Old Town character forward. Set in the X-500 flood zone within Key West's Historic District, this two-bedroom, two-bath cottage offers the opportunity for thoughtful renovation--a chance to bring the home into the present while preserving its enduring appeal. Downstairs, the living area, kitchen, and guest bedroom establish a straightforward layout. Upstairs, the primary suite has its own bath and closet. Outside, privacy fencing and mature tropical landscaping frame a backyard ready for your own vision. The rear deck offers space for outdoor dining and quiet afternoons, with the possibility of a cocktail pool, subject to space, permitting, and required approvals. Walk to neighborhood restaurants, galleries, and world-famous Duval Street, or bicycle to the island's beaches and parks. Mornings on the porch. Afternoons by the water. A tropical retreat shaped around the way you want to live. An Old Town original, ready for a little imagination and a thoughtful hand.

2 Beds ⋅ 2 Baths ⋅ 621896 MLS

A Key West Antiquity. A fresh point of view. The story of 921 Angela Street reaches into Key West's cigar-making past. The address appears in the city's 1906 directory as the residence of cigar maker Claude Johnson--a connection to the craftsmen who helped shape the island. Today, Dade County pine walls and floors, high ceilings, and a front porch that participates in the neighborhood carry that Old Town character forward. Set in the X-500 flood zone within Key West's Historic District, this two-bedroom, two-bath cottage offers the opportunity for thoughtful renovation--a chance to bring the home into the present while preserving its enduring appeal. Downstairs, the living area, kitchen, and guest bedroom establish a straightforward layout. Upstairs, the primary suite has its own bath and closet. Outside, privacy fencing and mature tropical landscaping frame a backyard ready for your own vision. The rear deck offers space for outdoor dining and quiet afternoons, with the possibility of a cocktail pool, subject to space, permitting, and required approvals. Walk to neighborhood restaurants, galleries, and world-famous Duval Street, or bicycle to the island's beaches and parks. Mornings on the porch. Afternoons by the water. A tropical retreat shaped around the way you want to live. An Old Town original, ready for a little imagination and a thoughtful hand.

921 Angela St, Key West

$1,700,000

Strong value-add multifamily fourplex investment opportunity with major capital improvements already completed. The property offers four two-bedroom residences totaling approximately 3,000 square feet, with each unit comprising approximately 750 square feet. The lower level includes two residences, while the upper level features two additional residences with approximately 960 square feet of combined balcony space. Major improvements include a new standing-seam metal roof, new impact-resistant windows and doors throughout, and completed concrete, stucco, and exterior work. The property is ready for the next owner to complete the remaining work and execute their preferred investment strategy. Once completed and delivered furnished, the property is projected to have the potential to generate more than $200,000 in annual gross rental income across all four units. Additional potential may include condominium conversion, subject to all applicable approvals and requirements. A compelling opportunity to complete, stabilize, and maximize a well-positioned Key West income-producing asset.

8 Beds ⋅ 5 Baths ⋅ 621893 MLS

Strong value-add multifamily fourplex investment opportunity with major capital improvements already completed. The property offers four two-bedroom residences totaling approximately 3,000 square feet, with each unit comprising approximately 750 square feet. The lower level includes two residences, while the upper level features two additional residences with approximately 960 square feet of combined balcony space. Major improvements include a new standing-seam metal roof, new impact-resistant windows and doors throughout, and completed concrete, stucco, and exterior work. The property is ready for the next owner to complete the remaining work and execute their preferred investment strategy. Once completed and delivered furnished, the property is projected to have the potential to generate more than $200,000 in annual gross rental income across all four units. Additional potential may include condominium conversion, subject to all applicable approvals and requirements. A compelling opportunity to complete, stabilize, and maximize a well-positioned Key West income-producing asset.

1224 2nd St, Key West

$5,650,000

Discover timeless design and effortless indoor-outdoor living in this custom-built 4-bedroom, 3.5-bath residence in Key West's coveted Casa Marina neighborhood. Completed in 2017, the home blends architectural elegance with comfortable everyday living, surrounded by lush landscaping and lighting throughout. At the heart of the home, a grand living room features soaring ceilings, cove lighting, and expansive NanaWall impact glass doors that open on both sides to both the pool and backyard patio. Designed for entertaining, the outdoor space features a substantial dining area and built-in kitchen. Inside, the kitchen and dining room are thoughtfully separated from the living room by a wall, with two connecting passages providing an easy flow between the spaces. The chef's kitchen showcases semi-precious dumortierite quartz countertops and premium Thermador appliances. A striking powder room features crushed Capiz shell wallpaper, an illuminated onyx sink, and a bronze waterfall faucet. The first-floor primary suite opens to an orchid potting garden on one side and an oversized outdoor shower on the other. Its bath features a private water closet and a six-foot window welcoming natural light. Upstairs, a bedroom or office offers a private terrace overlooking the pools, while two additional ensuite bedrooms share a den complete with a wet bar, and a full-size laundry room From the coral stone entry pathways over interconnected pools to the glass-railed staircase, and espresso Acacia wood flooring, thoughtful details distinguish this home. Additional amenities include a covered carport with a motorized door and EV charging, a whole-house generator, and a heated and chilled pool.

3 Beds ⋅ 4 Baths ⋅ 621891 MLS

Discover timeless design and effortless indoor-outdoor living in this custom-built 4-bedroom, 3.5-bath residence in Key West's coveted Casa Marina neighborhood. Completed in 2017, the home blends architectural elegance with comfortable everyday living, surrounded by lush landscaping and lighting throughout. At the heart of the home, a grand living room features soaring ceilings, cove lighting, and expansive NanaWall impact glass doors that open on both sides to both the pool and backyard patio. Designed for entertaining, the outdoor space features a substantial dining area and built-in kitchen. Inside, the kitchen and dining room are thoughtfully separated from the living room by a wall, with two connecting passages providing an easy flow between the spaces. The chef's kitchen showcases semi-precious dumortierite quartz countertops and premium Thermador appliances. A striking powder room features crushed Capiz shell wallpaper, an illuminated onyx sink, and a bronze waterfall faucet. The first-floor primary suite opens to an orchid potting garden on one side and an oversized outdoor shower on the other. Its bath features a private water closet and a six-foot window welcoming natural light. Upstairs, a bedroom or office offers a private terrace overlooking the pools, while two additional ensuite bedrooms share a den complete with a wet bar, and a full-size laundry room From the coral stone entry pathways over interconnected pools to the glass-railed staircase, and espresso Acacia wood flooring, thoughtful details distinguish this home. Additional amenities include a covered carport with a motorized door and EV charging, a whole-house generator, and a heated and chilled pool.

1119 Johnson St, Key West

$525,000

Enjoy the relaxed Key West lifestyle at Salt Ponds, a residential condominium community surrounded by tropical landscaping and a peaceful island atmosphere. This inviting home offers a comfortable setting for everyday living or a seasonal retreat, with convenient access to Key West's beaches, dining, shopping, and Old Town. A welcoming opportunity to enjoy island life in a well-established community. Private carport included.

2 Beds ⋅ 2 Baths ⋅ 621888 MLS

Enjoy the relaxed Key West lifestyle at Salt Ponds, a residential condominium community surrounded by tropical landscaping and a peaceful island atmosphere. This inviting home offers a comfortable setting for everyday living or a seasonal retreat, with convenient access to Key West's beaches, dining, shopping, and Old Town. A welcoming opportunity to enjoy island life in a well-established community. Private carport included.

3635 Seaside Dr Unit 205, Key West

$5,300,000

A rare opportunity to own a beautifully renovated historic property on coveted Fleming Street in the heart of Old Town Key West. Thoughtfully designed and renovated with exceptional craftsmanship, this unique property offers 7 bedrooms and 6 baths, creating an extraordinary combination of flexibility, privacy, and Old Town charm. The property is comprised of a 5-bedroom, 4-bath main residence, a separate one-bedroom guest apartment, and a one-bedroom pool cottage, each offering its own living space and kitchen. The guest apartment provides the perfect private quarters for visiting family and friends, or could easily be incorporated into the main residence to create additional living space or an expansive primary suite. The detached pool cottage offers yet another private retreat or rental opportunity. Outdoor living is at the heart of this exceptional property. A secluded, lushly landscaped entertaining area features a lagoon-style heated saltwater pool, tiki bar, and outdoor shower - an ideal setting for relaxing afternoons, sunset cocktails, and entertaining guests. Front and rear balconies provide additional opportunities to enjoy the quintessential Key West lifestyle, from morning coffee to evening cocktails. A private off-street parking space adds an especially valuable convenience in Old Town. Inside, the renovation reflects an exceptional level of craftsmanship and attention to detail, with beautiful finishes and crown molding throughout. Just a few blocks from the energy of Duval Street, the Historic Seaport and all that Old Town Key West has to offer, yet designed to provide a private oasis when you return home. A truly special property with endless possibilities for living, entertaining, and enjoying the Key West lifestyle. Owner is a licensed Florida Real Estate agent.

7 Beds ⋅ 6 Baths ⋅ 621882 MLS

A rare opportunity to own a beautifully renovated historic property on coveted Fleming Street in the heart of Old Town Key West. Thoughtfully designed and renovated with exceptional craftsmanship, this unique property offers 7 bedrooms and 6 baths, creating an extraordinary combination of flexibility, privacy, and Old Town charm. The property is comprised of a 5-bedroom, 4-bath main residence, a separate one-bedroom guest apartment, and a one-bedroom pool cottage, each offering its own living space and kitchen. The guest apartment provides the perfect private quarters for visiting family and friends, or could easily be incorporated into the main residence to create additional living space or an expansive primary suite. The detached pool cottage offers yet another private retreat or rental opportunity. Outdoor living is at the heart of this exceptional property. A secluded, lushly landscaped entertaining area features a lagoon-style heated saltwater pool, tiki bar, and outdoor shower - an ideal setting for relaxing afternoons, sunset cocktails, and entertaining guests. Front and rear balconies provide additional opportunities to enjoy the quintessential Key West lifestyle, from morning coffee to evening cocktails. A private off-street parking space adds an especially valuable convenience in Old Town. Inside, the renovation reflects an exceptional level of craftsmanship and attention to detail, with beautiful finishes and crown molding throughout. Just a few blocks from the energy of Duval Street, the Historic Seaport and all that Old Town Key West has to offer, yet designed to provide a private oasis when you return home. A truly special property with endless possibilities for living, entertaining, and enjoying the Key West lifestyle. Owner is a licensed Florida Real Estate agent.

923 Fleming St, Key West

$2,199,000

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

3 Beds ⋅ 2 Baths ⋅ 621869 MLS

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

3821 Eagle Ave, Key West

$2,249,000

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

4 Beds ⋅ 4 Baths ⋅ 621864 MLS

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

1104 Packer St, Key West

$895,000

Historic Old Town Key West charm, completely reimagined with the luxury and convenience of modern living. Located in the desirable X Flood Zone, this extraordinary townhome has undergone an extensive, top to bottom transformation. Far more than a visual renovation, the home features under the hood all new plumbing and electric wiring and systems. The beautifully redesigned interiors, contemporary finishes, and thoughtful upgrades throughout makes nearly everything feels brand new. One of only two units, the property enjoys an exceptionally low HOA fee of just $35 per month, covering common area insurance, maintenance, and reserves. Even better, this stunning home is offered fully furnished as shown. Just bring your toothbrush and begin enjoying the island lifestyle on the day of closing. Inside are two inviting bedrooms, two beautifully renovated full bathrooms, and a versatile bonus area with a Murphy bed for guests or a home office. The primary suite features a private ensuite bath, while both bathrooms showcase luxurious tiled walk-in showers and modern fixtures. The completely reimagined kitchen features a Frigidaire refrigerator, THOR gas range, ZLINE microwave, Samsung smart dishwasher, island sink with disposal, GE Profile all-in-one washer/dryer, wine cooler, and beverage cooler. Soaring cathedral ceilings and two expansive skylights fill the living space with natural light. Central air conditioning and a supplemental mini-split provide year-round comfort. Outside, a private tropical retreat awaits, complete with a spacious deck, built-in seating, propane fire feature, string lights, privacy fencing, and full size hot tub. A rare opportunity to enjoy the character of historic Key West with the freshness of a thoroughly reinvented home. Ideal as a primary residence, second home, or potential monthly rental. Completely reimagined, beautifully furnished, and move in ready.

3 Beds ⋅ 2 Baths ⋅ 621844 MLS

Historic Old Town Key West charm, completely reimagined with the luxury and convenience of modern living. Located in the desirable X Flood Zone, this extraordinary townhome has undergone an extensive, top to bottom transformation. Far more than a visual renovation, the home features under the hood all new plumbing and electric wiring and systems. The beautifully redesigned interiors, contemporary finishes, and thoughtful upgrades throughout makes nearly everything feels brand new. One of only two units, the property enjoys an exceptionally low HOA fee of just $35 per month, covering common area insurance, maintenance, and reserves. Even better, this stunning home is offered fully furnished as shown. Just bring your toothbrush and begin enjoying the island lifestyle on the day of closing. Inside are two inviting bedrooms, two beautifully renovated full bathrooms, and a versatile bonus area with a Murphy bed for guests or a home office. The primary suite features a private ensuite bath, while both bathrooms showcase luxurious tiled walk-in showers and modern fixtures. The completely reimagined kitchen features a Frigidaire refrigerator, THOR gas range, ZLINE microwave, Samsung smart dishwasher, island sink with disposal, GE Profile all-in-one washer/dryer, wine cooler, and beverage cooler. Soaring cathedral ceilings and two expansive skylights fill the living space with natural light. Central air conditioning and a supplemental mini-split provide year-round comfort. Outside, a private tropical retreat awaits, complete with a spacious deck, built-in seating, propane fire feature, string lights, privacy fencing, and full size hot tub. A rare opportunity to enjoy the character of historic Key West with the freshness of a thoroughly reinvented home. Ideal as a primary residence, second home, or potential monthly rental. Completely reimagined, beautifully furnished, and move in ready.

1004 Watson St Unit 1, Key West

$979,000

Available for immediate occupancy and offered at $979,000, 1709 Catherine Street combines a modern open floor plan with a spacious lot. This 3 bedroom and 2 bath home sits on more than 6,800 sq. ft., offering ample outdoor space and potential for future expansion. The fully fenced rear yard features a patio, a generous, covered porch, and a versatile 14 x 10 storage shed. With its substantial size, open space free of protected trees, and access for equipment, the yard offers potential for a swimming pool addition. A wide gate on the right side provides access for boat, RV, or additional vehicle parking, as permitted by code. Off-street parking accommodates 3 or more cars, with potential to add an EV charging station. A newer metal roof and impeccably maintained exterior complement the home's practical features, including wiring, plumbing, and propane tanks in place for the addition of a whole-house generator. Enjoy all the conveniences of living on the preferred western half of the island. Photos were taken in 2025 and are considered a fair representation of the property.

3 Beds ⋅ 2 Baths ⋅ 621825 MLS

Available for immediate occupancy and offered at $979,000, 1709 Catherine Street combines a modern open floor plan with a spacious lot. This 3 bedroom and 2 bath home sits on more than 6,800 sq. ft., offering ample outdoor space and potential for future expansion. The fully fenced rear yard features a patio, a generous, covered porch, and a versatile 14 x 10 storage shed. With its substantial size, open space free of protected trees, and access for equipment, the yard offers potential for a swimming pool addition. A wide gate on the right side provides access for boat, RV, or additional vehicle parking, as permitted by code. Off-street parking accommodates 3 or more cars, with potential to add an EV charging station. A newer metal roof and impeccably maintained exterior complement the home's practical features, including wiring, plumbing, and propane tanks in place for the addition of a whole-house generator. Enjoy all the conveniences of living on the preferred western half of the island. Photos were taken in 2025 and are considered a fair representation of the property.

1709 Catherine St, Key West

$2,099,000

Rare old town 4 unit property. On the corner of Angela and Ashe streets. This property consists of a 2 bedroom unit and 3 1 bedroom units. All units have separate water and electric meters. Each unit has dedicated outdoor space. This is a perfect investment property. Buyers would need to verify use and refurbishment with the City. Currently two units have long term tenants. Two units are vacant. This is a great opportunity in a perfect location.

5 Beds ⋅ 4 Baths ⋅ 621819 MLS

Rare old town 4 unit property. On the corner of Angela and Ashe streets. This property consists of a 2 bedroom unit and 3 1 bedroom units. All units have separate water and electric meters. Each unit has dedicated outdoor space. This is a perfect investment property. Buyers would need to verify use and refurbishment with the City. Currently two units have long term tenants. Two units are vacant. This is a great opportunity in a perfect location.

1125 Angela St, Key West

$1,895,000

A former church with a practical second calling. At 905 Grinnell Street, four occupied residences carry monthly rents totaling $11,249. There is also off-street parking--a feature whose virtues need little explanation to anyone acquainted with Old Town. The building retains its distinctive character while accommodating a three-bedroom residence, two two-bedroom residences, and a studio, each with one bathroom. Separate entrances and outdoor spaces lend the apartments a measure of independence. Together, they comprise approximately 3,383 square feet on a 5,737-square-foot lot. Concrete-block construction, a metal roof, and a location in the X-500 flood zone supply the practical details. The surrounding Historic District supplies the rest: neighborhood restaurants, shops, and Duval Street within walking distance. Offered at $1,895,000, with tenants in place and an established rental history. Rental and operating statements are available for those who prefer to read beyond the photographs.

8 Beds ⋅ 4 Baths ⋅ 621807 MLS

A former church with a practical second calling. At 905 Grinnell Street, four occupied residences carry monthly rents totaling $11,249. There is also off-street parking--a feature whose virtues need little explanation to anyone acquainted with Old Town. The building retains its distinctive character while accommodating a three-bedroom residence, two two-bedroom residences, and a studio, each with one bathroom. Separate entrances and outdoor spaces lend the apartments a measure of independence. Together, they comprise approximately 3,383 square feet on a 5,737-square-foot lot. Concrete-block construction, a metal roof, and a location in the X-500 flood zone supply the practical details. The surrounding Historic District supplies the rest: neighborhood restaurants, shops, and Duval Street within walking distance. Offered at $1,895,000, with tenants in place and an established rental history. Rental and operating statements are available for those who prefer to read beyond the photographs.

905 Grinnell St, Key West

$2,190,000

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

5 Beds ⋅ 4 Baths ⋅ 621798 MLS

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

1519 Johnson St, Key West

$850,000

Located in the heart of downtown Key West's Historic Seaport, Conch Harbor Marina offers unparalleled access to both the Gulf of Mexico and the Atlantic Ocean, making it an ideal home base for boating enthusiasts. Slip 16 accommodates vessels up to 45' LOA and includes deeded bay-bottom ownership. Whether you're passionate about fishing, cruising, or exploring the nearby islands, this slip offers the ideal storage solution with direct access to some of the best waters in the Keys. Enjoy the flexibility to live aboard, keep the slip for your own boating and island lifestyle, or take advantage of the marina's rental program when you're not using it. This secure, gated dock slip offer convenient access to the boardwalk along the Historic Seaport. Slip ownership offers a variety of amenities and an unbeatable Old Town location, just a short walk to Duval Street, restaurants, shops, and entertainment. Conch Harbor Marina offers high-speed fueling, in-slip pump-out service, shower and laundry facilities, a large on-site pool, a ship store stocked with bait and fishing supplies, and beautiful Ipe docks. Don't miss this rare opportunity to own your own piece of the Key West boating lifestyle at iconic marina at Conch Harbor. *Buyer to verify depth and dimensions.

621792 MLS

Located in the heart of downtown Key West's Historic Seaport, Conch Harbor Marina offers unparalleled access to both the Gulf of Mexico and the Atlantic Ocean, making it an ideal home base for boating enthusiasts. Slip 16 accommodates vessels up to 45' LOA and includes deeded bay-bottom ownership. Whether you're passionate about fishing, cruising, or exploring the nearby islands, this slip offers the ideal storage solution with direct access to some of the best waters in the Keys. Enjoy the flexibility to live aboard, keep the slip for your own boating and island lifestyle, or take advantage of the marina's rental program when you're not using it. This secure, gated dock slip offer convenient access to the boardwalk along the Historic Seaport. Slip ownership offers a variety of amenities and an unbeatable Old Town location, just a short walk to Duval Street, restaurants, shops, and entertainment. Conch Harbor Marina offers high-speed fueling, in-slip pump-out service, shower and laundry facilities, a large on-site pool, a ship store stocked with bait and fishing supplies, and beautiful Ipe docks. Don't miss this rare opportunity to own your own piece of the Key West boating lifestyle at iconic marina at Conch Harbor. *Buyer to verify depth and dimensions.

951 Caroline St Unit 16, Key West

$2,490,000

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

3 Beds ⋅ 8 Baths ⋅ 621784 MLS

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

402 Applerouth Ln, Key West

$569,000

Your opportunity to own an affordable townhome in Key West with updates already in place. A newly upgraded downstairs entryway features flood-resilient wall construction, new modern vinyl flooring on the first floor and a custom-made staircase. Additional updates include a new water heater and a new smart thermostat. Nestled in the back of the Solana Village complex, with no front-facing or rear neighbors, this well-maintained home offers a tucked-away, private setting. Featuring two bedrooms and one-and-a-half baths, approximately 1,050 square feet, a two-car carport and ground-level storage, it offers comfort and convenience with opportunities to add your own personal style. A junior Olympic-sized community pool and a private community playground and green space are only steps away. A low annual HOA fee of $1,500 adds to the appeal. Enjoy a convenient location near schools, shopping, dining and all the attractions that make Key West such a special place to call home. Whether you're a first-time buyer, looking for an island getaway or considering an investment property, 3314 Northside Drive, Unit 62 offers an accessible entry into Key West living. The seller is offering a $1,000 credit toward your choice of washer/dryer unit.

2 Beds ⋅ 2 Baths ⋅ 621781 MLS

Your opportunity to own an affordable townhome in Key West with updates already in place. A newly upgraded downstairs entryway features flood-resilient wall construction, new modern vinyl flooring on the first floor and a custom-made staircase. Additional updates include a new water heater and a new smart thermostat. Nestled in the back of the Solana Village complex, with no front-facing or rear neighbors, this well-maintained home offers a tucked-away, private setting. Featuring two bedrooms and one-and-a-half baths, approximately 1,050 square feet, a two-car carport and ground-level storage, it offers comfort and convenience with opportunities to add your own personal style. A junior Olympic-sized community pool and a private community playground and green space are only steps away. A low annual HOA fee of $1,500 adds to the appeal. Enjoy a convenient location near schools, shopping, dining and all the attractions that make Key West such a special place to call home. Whether you're a first-time buyer, looking for an island getaway or considering an investment property, 3314 Northside Drive, Unit 62 offers an accessible entry into Key West living. The seller is offering a $1,000 credit toward your choice of washer/dryer unit.

3314 Northside Dr Unit 62, Key West

2601 S Roosevelt Blvd Unit 610A, Key West

$995,000

This stunning 3 bedroom penthouse condo overlooks the ocean, pool, and has a bird's eye view of the Gulf. Brilliant white, crisp kitchen with updated appliances and smartly appointed living/dining room, this is a home ready for living the Key West Beach Life! Updated bathrooms feature one with a tub, and one with a large walk-in shower. Bright cheery bedrooms and an in-condo laundry round out this PERFECT oceanview piece of Paradise!

3 Beds ⋅ 2 Baths ⋅ 621777 MLS

This stunning 3 bedroom penthouse condo overlooks the ocean, pool, and has a bird's eye view of the Gulf. Brilliant white, crisp kitchen with updated appliances and smartly appointed living/dining room, this is a home ready for living the Key West Beach Life! Updated bathrooms feature one with a tub, and one with a large walk-in shower. Bright cheery bedrooms and an in-condo laundry round out this PERFECT oceanview piece of Paradise!

2601 S Roosevelt Blvd Unit 610A, Key West

$2,250,000

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

3 Beds ⋅ 3 Baths ⋅ 621771 MLS

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

115 Front St Unit APT 101, Key West

$825,000

Charming Home in the Meadows, Old Town, Key West. This beautiful completely renovated one bedroom cottage on Pearl Street is move in ready, and is being sold furnished. Stepping into the home through the custom built Dutch-door, the interior is bright, the walls are shadow-gap wood, there is new flooring, and recessed LED lighting throughout. The Bedroom has a murphy bed, and built in bedroom drawers, with additional storage. The Kitchen has custom cabinets, granite countertops, and is steps away from the back deck with a Tiki and wet bar - and outside seating area. Mitsubishi mini split AC, Custom shades, All new impact windows and doors, and the front Dutch Door has hurricane panels. During the renovation, the whole house was insulated between the studs, 3/4 inch pressure treated plywood added, then 1' fire rock, and then lap siding- PT-kiln dried-dipped on both sides with primer. This property is completely fenced, has a sprinkler system, Outdoor shower, and the best part- is a wonderful front porch to relax and watch the world go by! Home Owners insurance is $ 1471.58, Flood Insurance is $ 1463.00

1 Beds ⋅ 1 Baths ⋅ 621769 MLS

Charming Home in the Meadows, Old Town, Key West. This beautiful completely renovated one bedroom cottage on Pearl Street is move in ready, and is being sold furnished. Stepping into the home through the custom built Dutch-door, the interior is bright, the walls are shadow-gap wood, there is new flooring, and recessed LED lighting throughout. The Bedroom has a murphy bed, and built in bedroom drawers, with additional storage. The Kitchen has custom cabinets, granite countertops, and is steps away from the back deck with a Tiki and wet bar - and outside seating area. Mitsubishi mini split AC, Custom shades, All new impact windows and doors, and the front Dutch Door has hurricane panels. During the renovation, the whole house was insulated between the studs, 3/4 inch pressure treated plywood added, then 1' fire rock, and then lap siding- PT-kiln dried-dipped on both sides with primer. This property is completely fenced, has a sprinkler system, Outdoor shower, and the best part- is a wonderful front porch to relax and watch the world go by! Home Owners insurance is $ 1471.58, Flood Insurance is $ 1463.00

817 Pearl St, Key West

$2,195,000

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

5 Beds ⋅ 5 Baths ⋅ 621768 MLS

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

2827 Harris Ave, Key West

$2,895,000

Fully restored historic 3BD/3BA with 1,600 sq ft of total living space in the heart of Old Town, with pool, private guest cottage, and off-street parking, located in X flood zone and offered turnkey. Some historic homes ask their next owners to take on a century of hidden repairs. This one asks only that you move in. With great care and pride, the owner restored the house from foundation to roof: a new foundation, new windows and siding, all-new electrical and plumbing, and every system beneath the surface brought current. The result is the character of an Old Town classic with the soundness of a home built today, and none of the worries that usually come with an older house. Inside, the main house is arranged as a 2BD/2BA, with both bedrooms ensuite, giving each occupant a private retreat of their own. Outside, the pool sets the tone for long winter afternoons in the tropical sun. Beside it, a separate 1BD/1BA guest cottage gives visiting family or friends their own quarters and bath, so everyone can share the season while keeping their privacy. Off-street parking for one car, a true premium in Old Town, makes arrivals and departures easy. The home is offered fully turnkey, with interiors curated by local designer Amie Woeppel, so a seasonal owner can arrive, unpack, and start living, with nothing left to fix or furnish. Every choice reflects an owner who restored this house to be lived in and loved, not simply sold. From the front door, Duval Street is a six-minute walk, with a wide selection of restaurants and bars along the way. Old Town history, rebuilt from the ground up and ready for its next chapter.

3 Beds ⋅ 3 Baths ⋅ 621758 MLS

Fully restored historic 3BD/3BA with 1,600 sq ft of total living space in the heart of Old Town, with pool, private guest cottage, and off-street parking, located in X flood zone and offered turnkey. Some historic homes ask their next owners to take on a century of hidden repairs. This one asks only that you move in. With great care and pride, the owner restored the house from foundation to roof: a new foundation, new windows and siding, all-new electrical and plumbing, and every system beneath the surface brought current. The result is the character of an Old Town classic with the soundness of a home built today, and none of the worries that usually come with an older house. Inside, the main house is arranged as a 2BD/2BA, with both bedrooms ensuite, giving each occupant a private retreat of their own. Outside, the pool sets the tone for long winter afternoons in the tropical sun. Beside it, a separate 1BD/1BA guest cottage gives visiting family or friends their own quarters and bath, so everyone can share the season while keeping their privacy. Off-street parking for one car, a true premium in Old Town, makes arrivals and departures easy. The home is offered fully turnkey, with interiors curated by local designer Amie Woeppel, so a seasonal owner can arrive, unpack, and start living, with nothing left to fix or furnish. Every choice reflects an owner who restored this house to be lived in and loved, not simply sold. From the front door, Duval Street is a six-minute walk, with a wide selection of restaurants and bars along the way. Old Town history, rebuilt from the ground up and ready for its next chapter.

711 Olivia St, Key West

$1,050,000

***Beautifully maintained, thoughtfully improved, and ready for its next chapter in Key West!*** Discover 3315 Donald Avenue, a home where quality, comfort, and island living come together beautifully! Tucked into desirable Buttonwood Court, this inviting 3-bedroom, 2-bath residence offers soaring vaulted ceilings, premier lighting, warm natural wood cabinetry, granite countertops, a spacious kitchen island, and a convenient pantry. The open, welcoming interior flows through sliding glass doors to a screened rear porch overlooking a natural wildlife area. Here, beautiful sunrises greet you from the back of the home, creating a peaceful setting for morning coffee or simply enjoying the natural surroundings. Pride of ownership is evident throughout, with thoughtful improvements, quality finishes, and inviting outdoor spaces designed for easy Key West living. Enjoy the convenience of being just minutes from Old Town's restaurants, galleries, entertainment, and waterfront attractions while returning home to a quieter neighborhood setting. With its appealing combination of location, comfort, and exceptional care, this property presents a wonderful opportunity for locals looking to put down roots or anyone ready to make Key West home. **A home that's been cared for with intention and is ready to be enjoyed from day one!**

3 Beds ⋅ 2 Baths ⋅ 621749 MLS

***Beautifully maintained, thoughtfully improved, and ready for its next chapter in Key West!*** Discover 3315 Donald Avenue, a home where quality, comfort, and island living come together beautifully! Tucked into desirable Buttonwood Court, this inviting 3-bedroom, 2-bath residence offers soaring vaulted ceilings, premier lighting, warm natural wood cabinetry, granite countertops, a spacious kitchen island, and a convenient pantry. The open, welcoming interior flows through sliding glass doors to a screened rear porch overlooking a natural wildlife area. Here, beautiful sunrises greet you from the back of the home, creating a peaceful setting for morning coffee or simply enjoying the natural surroundings. Pride of ownership is evident throughout, with thoughtful improvements, quality finishes, and inviting outdoor spaces designed for easy Key West living. Enjoy the convenience of being just minutes from Old Town's restaurants, galleries, entertainment, and waterfront attractions while returning home to a quieter neighborhood setting. With its appealing combination of location, comfort, and exceptional care, this property presents a wonderful opportunity for locals looking to put down roots or anyone ready to make Key West home. **A home that's been cared for with intention and is ready to be enjoyed from day one!**

3315 Donald Ave, Key West

$2,399,000

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

4 Beds ⋅ 4 Baths ⋅ 621742 MLS

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

1320 Eliza St, Key West

$2,649,000

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

3 Beds ⋅ 3 Baths ⋅ 621735 MLS

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

410 Louisa St, Key West

$1,505,000

ASSUMABLE 5.625% VA LOAN! Discover your private Key West retreat at 1414 18th Street, where a beautifully renovated home, inviting tropical pool, and attractive financing opportunity come together. Set on a 6,000 square foot corner lot in a quiet New Town neighborhood, this concrete block home offers privacy, comfort, and easy island living. The sparkling pool is a standout feature, complete with a cascading coral waterfall that sets the mood for relaxing afternoons and entertaining friends. Private outdoor spaces and low maintenance landscaping mean more time enjoying the sunshine and less time on upkeep. Inside, a bright, open floor plan features luxury vinyl plank flooring, recessed lighting, and tasteful modern updates. The renovated kitchen includes quartz countertops, stainless steel appliances, a gas range, and updated cabinetry, with an easy connection to the living areas. All 3 bedrooms are generously sized, and all 3 bathrooms have been updated. The primary suite includes a spacious walk in closet. A dedicated laundry area with a full size washer and dryer, additional interior storage, and generous off street parking add everyday convenience. Just minutes from beaches, shopping, dining, and Old Town, this move in ready property combines the convenience of New Town with the feel of a private island escape. An existing 5.625% VA loan may be assumable by a qualified buyer, including a nonveteran, subject to loan servicer approval and applicable VA requirements. Contact us for loan details and assumption terms. Whether you're looking for a full time home, seasonal getaway, or investment opportunity, 1414 18th Street offers updated living spaces, a wonderful poolside lifestyle, and low maintenance appeal.

3 Beds ⋅ 3 Baths ⋅ 621726 MLS

ASSUMABLE 5.625% VA LOAN! Discover your private Key West retreat at 1414 18th Street, where a beautifully renovated home, inviting tropical pool, and attractive financing opportunity come together. Set on a 6,000 square foot corner lot in a quiet New Town neighborhood, this concrete block home offers privacy, comfort, and easy island living. The sparkling pool is a standout feature, complete with a cascading coral waterfall that sets the mood for relaxing afternoons and entertaining friends. Private outdoor spaces and low maintenance landscaping mean more time enjoying the sunshine and less time on upkeep. Inside, a bright, open floor plan features luxury vinyl plank flooring, recessed lighting, and tasteful modern updates. The renovated kitchen includes quartz countertops, stainless steel appliances, a gas range, and updated cabinetry, with an easy connection to the living areas. All 3 bedrooms are generously sized, and all 3 bathrooms have been updated. The primary suite includes a spacious walk in closet. A dedicated laundry area with a full size washer and dryer, additional interior storage, and generous off street parking add everyday convenience. Just minutes from beaches, shopping, dining, and Old Town, this move in ready property combines the convenience of New Town with the feel of a private island escape. An existing 5.625% VA loan may be assumable by a qualified buyer, including a nonveteran, subject to loan servicer approval and applicable VA requirements. Contact us for loan details and assumption terms. Whether you're looking for a full time home, seasonal getaway, or investment opportunity, 1414 18th Street offers updated living spaces, a wonderful poolside lifestyle, and low maintenance appeal.

1414 18th St, Key West

$2,229,000

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

3 Beds ⋅ 3 Baths ⋅ 621725 MLS

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

3801 Flagler Ave, Key West

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