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3930 S Roosevelt Blvd Unit N108, Key West

NEW PRICE.....Welcome to this beautifully updated condo at 3930 S. Roosevelt Blvd. #N108, offering the perfect blend of comfort, convenience, and island living. Overlooking the sparkling community pool, this inviting residence features a tastefully remodeled kitchen with modern finishes, newer flooring throughout, and a bright, open living space designed for easy living and entertaining. Enjoy your morning coffee or evening cocktail with relaxing pool views, while the covered parking bay provides the added convenience and protection every Key West homeowner appreciates. Residents also enjoy outstanding community amenities, including a newly completed state-of-the-art fitness center, adding even more value to this desirable complex. Located just minutes from beaches, shopping, dining, and Old Town Key West, this move-in-ready condo is ideal as a full-time residence, vacation getaway, or investment property. Don't miss this opportunity to own a beautifully updated piece of paradise in one of Key West's most desirable locations. Call today to set up your showing.... Very easy to show

2 Beds ⋅ 2 Baths ⋅ 620690 MLS

NEW PRICE.....Welcome to this beautifully updated condo at 3930 S. Roosevelt Blvd. #N108, offering the perfect blend of comfort, convenience, and island living. Overlooking the sparkling community pool, this inviting residence features a tastefully remodeled kitchen with modern finishes, newer flooring throughout, and a bright, open living space designed for easy living and entertaining. Enjoy your morning coffee or evening cocktail with relaxing pool views, while the covered parking bay provides the added convenience and protection every Key West homeowner appreciates. Residents also enjoy outstanding community amenities, including a newly completed state-of-the-art fitness center, adding even more value to this desirable complex. Located just minutes from beaches, shopping, dining, and Old Town Key West, this move-in-ready condo is ideal as a full-time residence, vacation getaway, or investment property. Don't miss this opportunity to own a beautifully updated piece of paradise in one of Key West's most desirable locations. Call today to set up your showing.... Very easy to show

3930 S Roosevelt Blvd Unit N108, Key West

3930 S Roosevelt Blvd Unit W314, Key West

$499,000

This bright, private 2BR/2BA corner unit sits at the end of the west wing, with an extra window that fills the space with light and only one shared wall for real quiet. This unit comes with covered parking. The kitchen is outfitted with stainless steel appliances, and a full-size washer and dryer means laundry day never means leaving home. A covered parking space (#122) comes with the sale. Las Salinas Condominiums is one of the best-kept communities in Key West, and it shows. The pool is sun-drenched and inviting, and the fitness center may be the best on the island, with private access to cardio and strength rooms that are always spotless and always stocked with quality equipment. Monthly fees of $535 cover building insurance, exterior maintenance, and full on-site management, so ownership here is refreshingly hands-off. Step outside and you're close to a grocery store, a day spa, and a bus stop for easy island transportation. Just past the entrance, the two-mile Smathers Beach promenade is calling, whether that's a sunrise walk, a bike ride, or a spot to watch the sky change color every evening. Add in open-lot parking for a second vehicle, plus storage and bicycle rooms, and this is a home built for the way you actually want to live in Key West. Call today to schedule a private showing.

2 Beds ⋅ 2 Baths ⋅ 620689 MLS

This bright, private 2BR/2BA corner unit sits at the end of the west wing, with an extra window that fills the space with light and only one shared wall for real quiet. This unit comes with covered parking. The kitchen is outfitted with stainless steel appliances, and a full-size washer and dryer means laundry day never means leaving home. A covered parking space (#122) comes with the sale. Las Salinas Condominiums is one of the best-kept communities in Key West, and it shows. The pool is sun-drenched and inviting, and the fitness center may be the best on the island, with private access to cardio and strength rooms that are always spotless and always stocked with quality equipment. Monthly fees of $535 cover building insurance, exterior maintenance, and full on-site management, so ownership here is refreshingly hands-off. Step outside and you're close to a grocery store, a day spa, and a bus stop for easy island transportation. Just past the entrance, the two-mile Smathers Beach promenade is calling, whether that's a sunrise walk, a bike ride, or a spot to watch the sky change color every evening. Add in open-lot parking for a second vehicle, plus storage and bicycle rooms, and this is a home built for the way you actually want to live in Key West. Call today to schedule a private showing.

3930 S Roosevelt Blvd Unit W314, Key West

$4,995,000

Welcome to an extraordinary oceanfront residence in the exclusive Casa Caselles community, where two townhomes have been masterfully combined into one spectacular 4,224 sq. ft. luxury retreat. Completely reimagined, this one-of-a-kind home features a private interior elevator with automatic doors accessing all floors, exceptional craftsmanship, and effortless oceanfront and poolside living. Offering 4 en-suite bedrooms, 4.5 baths, 2 expansive living rooms divided by a wall insulated with commercial soundproofing, an exercise room, and a hidden office seamlessly integrated into the custom kitchen, the residence is designed for everyday comfort and grand-scale entertaining. The chef's kitchen centers around an oversized island with custom European-style cabinetry, premium quartz countertops, a BlueStar gas range, paneled Sub-Zero refrigerator, Cove dishwasher, U-Line ice maker, wine refrigerator, and Perlick refrigerator/freezer drawers. The family room includes an electric fireplace and custom wet bar with refrigerator drawers, dishwasher, and built-in cabinetry. Travertine flooring, custom built-ins, hidden storage, recessed lighting, remote-controlled window coverings, and in-wall TV wiring reflect meticulous attention to detail. Every major system has been replaced, including electrical, plumbing, insulation, and HVAC. Twelve balconies and hurricane-rated sliding glass doors provide beautiful light in every room, while a whole-house generator provides peace of mind. The luxurious primary suite offers a custom walk-in closet, and every bedroom has private balcony access. A guest suite includes a zero-entry shower for added comfort and accessibility. Tiled courtyards, expanded entertaining terraces, covered parking for four vehicles, an outdoor shower, and multiple laundry areas enhance daily living. Residents also enjoy an oceanfront pool overlooking the Atlantic, completing one of Key West's most distinctive waterfront residences.

4 Beds ⋅ 5 Baths ⋅ 620618 MLS

Welcome to an extraordinary oceanfront residence in the exclusive Casa Caselles community, where two townhomes have been masterfully combined into one spectacular 4,224 sq. ft. luxury retreat. Completely reimagined, this one-of-a-kind home features a private interior elevator with automatic doors accessing all floors, exceptional craftsmanship, and effortless oceanfront and poolside living. Offering 4 en-suite bedrooms, 4.5 baths, 2 expansive living rooms divided by a wall insulated with commercial soundproofing, an exercise room, and a hidden office seamlessly integrated into the custom kitchen, the residence is designed for everyday comfort and grand-scale entertaining. The chef's kitchen centers around an oversized island with custom European-style cabinetry, premium quartz countertops, a BlueStar gas range, paneled Sub-Zero refrigerator, Cove dishwasher, U-Line ice maker, wine refrigerator, and Perlick refrigerator/freezer drawers. The family room includes an electric fireplace and custom wet bar with refrigerator drawers, dishwasher, and built-in cabinetry. Travertine flooring, custom built-ins, hidden storage, recessed lighting, remote-controlled window coverings, and in-wall TV wiring reflect meticulous attention to detail. Every major system has been replaced, including electrical, plumbing, insulation, and HVAC. Twelve balconies and hurricane-rated sliding glass doors provide beautiful light in every room, while a whole-house generator provides peace of mind. The luxurious primary suite offers a custom walk-in closet, and every bedroom has private balcony access. A guest suite includes a zero-entry shower for added comfort and accessibility. Tiled courtyards, expanded entertaining terraces, covered parking for four vehicles, an outdoor shower, and multiple laundry areas enhance daily living. Residents also enjoy an oceanfront pool overlooking the Atlantic, completing one of Key West's most distinctive waterfront residences.

1616 Atlantic Blvd Unit 11, 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

$725,000

''Seaport Sanctuary'' Located within the Land's End compound steps away from the Historic Key West Seaport and Harbor Walk. This 1 bedroom 1 bath conch cottage features an open floor plan with a storage loft, cathedral ceilings and hardwood floors. Nestled down a brick pathway across from the residents only heated pool. Professionally maintained landscaping surrounds this 6 freestanding conch home complex. Call today!

1 Beds ⋅ 1 Baths ⋅ 620493 MLS

''Seaport Sanctuary'' Located within the Land's End compound steps away from the Historic Key West Seaport and Harbor Walk. This 1 bedroom 1 bath conch cottage features an open floor plan with a storage loft, cathedral ceilings and hardwood floors. Nestled down a brick pathway across from the residents only heated pool. Professionally maintained landscaping surrounds this 6 freestanding conch home complex. Call today!

308 Margaret St Unit 3, 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

$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

$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

$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

$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

$639,000

Discover your ideal pied-à-terre in the heart of Key West! This charming 1-bedroom, 1-bathroom apartment on Olivia Street offers a perfect blend of comfort and convenience. Featuring two balconies, you can enjoy your morning coffee or unwind in the evening while soaking up the tropical vibes. The cozy living space is adorned with modern finishes, complemented by a well-equipped kitchen that makes entertaining a breeze. Located just steps from local attractions, exquisite dining, and vibrant nightlife, this apartment is an excellent choice for those seeking the ultimate island lifestyle. Experience your perfect getaway in this Key West gem!

1 Beds ⋅ 1 Baths ⋅ 620158 MLS

Discover your ideal pied-à-terre in the heart of Key West! This charming 1-bedroom, 1-bathroom apartment on Olivia Street offers a perfect blend of comfort and convenience. Featuring two balconies, you can enjoy your morning coffee or unwind in the evening while soaking up the tropical vibes. The cozy living space is adorned with modern finishes, complemented by a well-equipped kitchen that makes entertaining a breeze. Located just steps from local attractions, exquisite dining, and vibrant nightlife, this apartment is an excellent choice for those seeking the ultimate island lifestyle. Experience your perfect getaway in this Key West gem!

1402 Olivia St Unit 2, Key West

$750,000

TRANSIENT LICENCE RECEIVERSHIP ZONE! Welcome to your slice of paradise in Key West! This charming 2-bedroom, 2-bathroom condo located just steps from Duval Street offers an incredible opportunity. Currently utilized as an income-producing vacation rental, this home presents the perfect blend of comfort and convenience. Nestled in the heart of Key West, this condo boasts proximity to renowned attractions, vibrant restaurants, and the lively energy of Duval Street, ensuring endless entertainment options for residents and guests alike. Just a few blocks away lies Key West's South Beach, where sun-soaked days and breathtaking sunrises await. The interior of this inviting condo features two spacious bedrooms, providing ample room for relaxation and rejuvenation after a day of exploring the island. The well-appointed bathrooms offer both style and functionality, catering to the needs of residents and visitors. Whether you're lounging on the private balcony, enjoying the tropical breeze, or venturing out to experience the vibrant culture of Key West, this condo offers the quintessential island lifestyle. Don't miss your chance to own a piece of paradise and capitalize on the flourishing vacation rental market in this coveted location. Seize this opportunity to invest in Key West living at its finest. Schedule your showing today and envision the endless possibilities that await in this delightful condo just steps from Duval Street!

2 Beds ⋅ 2 Baths ⋅ 620157 MLS

TRANSIENT LICENCE RECEIVERSHIP ZONE! Welcome to your slice of paradise in Key West! This charming 2-bedroom, 2-bathroom condo located just steps from Duval Street offers an incredible opportunity. Currently utilized as an income-producing vacation rental, this home presents the perfect blend of comfort and convenience. Nestled in the heart of Key West, this condo boasts proximity to renowned attractions, vibrant restaurants, and the lively energy of Duval Street, ensuring endless entertainment options for residents and guests alike. Just a few blocks away lies Key West's South Beach, where sun-soaked days and breathtaking sunrises await. The interior of this inviting condo features two spacious bedrooms, providing ample room for relaxation and rejuvenation after a day of exploring the island. The well-appointed bathrooms offer both style and functionality, catering to the needs of residents and visitors. Whether you're lounging on the private balcony, enjoying the tropical breeze, or venturing out to experience the vibrant culture of Key West, this condo offers the quintessential island lifestyle. Don't miss your chance to own a piece of paradise and capitalize on the flourishing vacation rental market in this coveted location. Seize this opportunity to invest in Key West living at its finest. Schedule your showing today and envision the endless possibilities that await in this delightful condo just steps from Duval Street!

508 Louisa St Unit 3, Key West

$1,300,000

Embrace the enchantment of Old Key West Charm in this Beautifully Updated Historic Conch 3 Bedroom-2 Bath Home, featuring a Tropical Landscaped community Pool creating ultimate relaxation. This timeless Conch Cottage is nestled in a secure gated compound of six Key West Style Cottages. Low HOA Fee $288 Monthly includes Pool and Landscaping maintenance. This home is in an X500 Flood Zone, Banks do not require Flood Insurance. Situated in the highly coveted Old Town North neighborhood, this home is in the heart of everything quintessentially Key West. Revel in the exquisite architecture, savor the diverse culinary delights, explore unique boutiques, and immerse yourself in the vibrant nightlife and rich cultural scene just a leisurely stroll from your doorstep. Just four blocks to the Historic Seaport and across from the iconic Five Brothers Coffee Shop. The renovated Living Room, Dining Room, and Kitchen features classic Vaulted Wood Ceilings, and Hard Wood Flooring. The renovated Modern Bathroom also features a Vaulted Wood Ceiling, and a spacious Glass and Tile Walk-In Shower, Custom Lighting, Custom Sink-Vanity, and Custom Mirrors. The lovely, renovated Kitchen features Stainless Steel Appliances, Custom Wood Cabinets, and a Custom Ceiling Fan-Light fixture. A spacious Covered and Screened Wood Accented Patio area connects the Main 2 Bedroom - 1 Bathroom Cottage to the adjoining Studio 1 Bedroom - 1 Bathroom separate living area. The Studio has a New AC Unit, Refrigerator, Microwave Oven, and an Air Fryer Oven. The Studio Bathroom has also been renovated with a Modern Glass and Tile Walk-In Shower, Custom Sink, Custom Lighted Mirror, and Custom Lighting. Both living areas have their own separate and private door entrances. Excellent Rental Income opportunity. This ideal 3BR-2BA floor plan can accommodate the owner living in one side, while renting the other side. Paradise Awaits in Old Town North Key West.

3 Beds ⋅ 2 Baths ⋅ 620150 MLS

Embrace the enchantment of Old Key West Charm in this Beautifully Updated Historic Conch 3 Bedroom-2 Bath Home, featuring a Tropical Landscaped community Pool creating ultimate relaxation. This timeless Conch Cottage is nestled in a secure gated compound of six Key West Style Cottages. Low HOA Fee $288 Monthly includes Pool and Landscaping maintenance. This home is in an X500 Flood Zone, Banks do not require Flood Insurance. Situated in the highly coveted Old Town North neighborhood, this home is in the heart of everything quintessentially Key West. Revel in the exquisite architecture, savor the diverse culinary delights, explore unique boutiques, and immerse yourself in the vibrant nightlife and rich cultural scene just a leisurely stroll from your doorstep. Just four blocks to the Historic Seaport and across from the iconic Five Brothers Coffee Shop. The renovated Living Room, Dining Room, and Kitchen features classic Vaulted Wood Ceilings, and Hard Wood Flooring. The renovated Modern Bathroom also features a Vaulted Wood Ceiling, and a spacious Glass and Tile Walk-In Shower, Custom Lighting, Custom Sink-Vanity, and Custom Mirrors. The lovely, renovated Kitchen features Stainless Steel Appliances, Custom Wood Cabinets, and a Custom Ceiling Fan-Light fixture. A spacious Covered and Screened Wood Accented Patio area connects the Main 2 Bedroom - 1 Bathroom Cottage to the adjoining Studio 1 Bedroom - 1 Bathroom separate living area. The Studio has a New AC Unit, Refrigerator, Microwave Oven, and an Air Fryer Oven. The Studio Bathroom has also been renovated with a Modern Glass and Tile Walk-In Shower, Custom Sink, Custom Lighted Mirror, and Custom Lighting. Both living areas have their own separate and private door entrances. Excellent Rental Income opportunity. This ideal 3BR-2BA floor plan can accommodate the owner living in one side, while renting the other side. Paradise Awaits in Old Town North Key West.

611 Grinnell St Unit 4, Key West

$1,239,000

OPEN HOUSE 09/19 from 11AM to 1PM Home has just been freshly painted and Is vacant easy to show. Owner also will give 5k credit towards buyers closing expenses Welcome to one of the most sought after gated communities in Key West Seaside Residences. This beautiful updated 2-bedroom 3.5 half bath offers 1824sq. ft of living space. It is a three-level townhouse with your own private elevator that accommodates all three levels. You have four private balconies on the top two floors which gives you a perfect view of the beautiful sunrises and sunsets. Not to mention that the roof deck has its private surroundings for beautiful views of the Atlantic Ocean and suntanning. On the first floor you will pull up to your private garage. There is also your laundry and half bath with Air conditioning. The rest of the first floor is your Bar/BBQ and ample space for entertaining your family and guests. This townhome comes with one of the few units with extra side yard which is turf with a putting green. Moving to the second floor there is your primary suite and ensuite bathroom with double vanities. There is a large shower for relaxing. Second bedroom also has its private full bath. Third floor opens to the main living room ocean view which flows to the dining room. The Kitchen features wood cabinetry with lots of storage. Granite countertops. Stainless Appliances and plenty of pantry storage, there is abundance of natural sunlight that flows across from large windows and doors. Townhouse comes with all impact hurricane windows and doors. Washer and dryer are fairly new (2023) and tankless water heater as well (2023). Air Condition replaced in September of 2023. (Priced to Sell). Included in your HOA fees are your insurances, pool and fitness center. Owner does hold a Florida Real Estate License

2 Beds ⋅ 4 Baths ⋅ 620140 MLS

OPEN HOUSE 09/19 from 11AM to 1PM Home has just been freshly painted and Is vacant easy to show. Owner also will give 5k credit towards buyers closing expenses Welcome to one of the most sought after gated communities in Key West Seaside Residences. This beautiful updated 2-bedroom 3.5 half bath offers 1824sq. ft of living space. It is a three-level townhouse with your own private elevator that accommodates all three levels. You have four private balconies on the top two floors which gives you a perfect view of the beautiful sunrises and sunsets. Not to mention that the roof deck has its private surroundings for beautiful views of the Atlantic Ocean and suntanning. On the first floor you will pull up to your private garage. There is also your laundry and half bath with Air conditioning. The rest of the first floor is your Bar/BBQ and ample space for entertaining your family and guests. This townhome comes with one of the few units with extra side yard which is turf with a putting green. Moving to the second floor there is your primary suite and ensuite bathroom with double vanities. There is a large shower for relaxing. Second bedroom also has its private full bath. Third floor opens to the main living room ocean view which flows to the dining room. The Kitchen features wood cabinetry with lots of storage. Granite countertops. Stainless Appliances and plenty of pantry storage, there is abundance of natural sunlight that flows across from large windows and doors. Townhouse comes with all impact hurricane windows and doors. Washer and dryer are fairly new (2023) and tankless water heater as well (2023). Air Condition replaced in September of 2023. (Priced to Sell). Included in your HOA fees are your insurances, pool and fitness center. Owner does hold a Florida Real Estate License

25 Seaside South Ct, Key West

$839,000

*** BEST PRICED 2/2 CONDO IN OLD TOWN *** Lionsgate community, heart of Old Town, one of Key West's most coveted small communities, known for its heated saltwater pool, lush tropical landscaping, and neighbors who actually know each other. Unit 321 sits on the second floor with vaulted ceilings, exposed beams, and an open layout that lives significantly larger than 944 sq ft. The kitchen and living room flow together naturally, good for cooking, entertaining, or simply unwinding. Quartz countertops, new laminate flooring, and fresh paint throughout make this move-in ready. Storage is genuinely rare here: a dedicated laundry room, an attic, and an assigned parking space at the unit. EV and golf-cart charging ready. X flood zone. This is a second home that actually feels like one.

2 Beds ⋅ 2 Baths ⋅ 620130 MLS

*** BEST PRICED 2/2 CONDO IN OLD TOWN *** Lionsgate community, heart of Old Town, one of Key West's most coveted small communities, known for its heated saltwater pool, lush tropical landscaping, and neighbors who actually know each other. Unit 321 sits on the second floor with vaulted ceilings, exposed beams, and an open layout that lives significantly larger than 944 sq ft. The kitchen and living room flow together naturally, good for cooking, entertaining, or simply unwinding. Quartz countertops, new laminate flooring, and fresh paint throughout make this move-in ready. Storage is genuinely rare here: a dedicated laundry room, an attic, and an assigned parking space at the unit. EV and golf-cart charging ready. X flood zone. This is a second home that actually feels like one.

1124 Olivia St Unit 321, Key West

$1,999,999

Tucked into the heart of Old Town, this beautifully restored residence pairs Key West's historic character with thoughtful modern updates--all just one block off Duval Street and three blocks from the iconic Southernmost Point. Taken down to the studs and fully renovated in 2018, the three-bedroom, two-bath home delivers high-end finishes throughout, plus the rare bonuses of a private gated courtyard and off-street parking. The layout is built for easy island living, blurring the line between indoors and out. Refined touches run throughout: impact-rated doors and windows, rich oak floors, custom tilework, and original Dade County Pine that's been carefully preserved. At the center of it all, the kitchen is made for entertaining, with stainless appliances, brushed marble counters, and eye-catching copper and bronze fixtures. The generously sized primary suite is a true retreat--vaulted cypress ceilings, a spa-inspired en suite, a showpiece copper soaking tub, and custom closets with room to spare. Add in abundant storage and easy-care landscaping, and the practical details are covered too. For buyers chasing style, comfort, and true walkability in one of Key West's most sought-after neighborhoods, this one belongs at the top of the list.

3 Beds ⋅ 2 Baths ⋅ 620106 MLS

Tucked into the heart of Old Town, this beautifully restored residence pairs Key West's historic character with thoughtful modern updates--all just one block off Duval Street and three blocks from the iconic Southernmost Point. Taken down to the studs and fully renovated in 2018, the three-bedroom, two-bath home delivers high-end finishes throughout, plus the rare bonuses of a private gated courtyard and off-street parking. The layout is built for easy island living, blurring the line between indoors and out. Refined touches run throughout: impact-rated doors and windows, rich oak floors, custom tilework, and original Dade County Pine that's been carefully preserved. At the center of it all, the kitchen is made for entertaining, with stainless appliances, brushed marble counters, and eye-catching copper and bronze fixtures. The generously sized primary suite is a true retreat--vaulted cypress ceilings, a spa-inspired en suite, a showpiece copper soaking tub, and custom closets with room to spare. Add in abundant storage and easy-care landscaping, and the practical details are covered too. For buyers chasing style, comfort, and true walkability in one of Key West's most sought-after neighborhoods, this one belongs at the top of the list.

1119 Whitehead St, Key West

$900,000

*Seller Motivated, told us to bring all reasonable Offers. 3/1 with a guest cottage/office space at rear of property with private full bath and kitchenette. 4/2 with cottage. All just awaiting a Buyers personal taste!. Huge lot with incredible area for big a beautiful pool! This is a perfect family 3/1 home in one of the best New Town neighborhoods. This fully gated home sits on a massive 7000 sf oversized lot and is completely move-in ready. The home boasts three bedrooms and one bath. The floor plan in the kitchen and living area flows perfectly for open living. Glass French doors open to the back patio (that could be enclosed for Florida room) and look out at the massive green lawn and native trees. The large back yard is perfect for expansion or creating your very own tropical oasis. Set back in complete privacy is a beautiful guest suite/office space with bath. The side yard with an additional privacy fence is perfect boat parking. This property is a must see! Occupied so must allow 24 hour notice.

3 Beds ⋅ 2 Baths ⋅ 620104 MLS

*Seller Motivated, told us to bring all reasonable Offers. 3/1 with a guest cottage/office space at rear of property with private full bath and kitchenette. 4/2 with cottage. All just awaiting a Buyers personal taste!. Huge lot with incredible area for big a beautiful pool! This is a perfect family 3/1 home in one of the best New Town neighborhoods. This fully gated home sits on a massive 7000 sf oversized lot and is completely move-in ready. The home boasts three bedrooms and one bath. The floor plan in the kitchen and living area flows perfectly for open living. Glass French doors open to the back patio (that could be enclosed for Florida room) and look out at the massive green lawn and native trees. The large back yard is perfect for expansion or creating your very own tropical oasis. Set back in complete privacy is a beautiful guest suite/office space with bath. The side yard with an additional privacy fence is perfect boat parking. This property is a must see! Occupied so must allow 24 hour notice.

1227 20th, Key West

$2,499,000

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

3 Beds ⋅ 4 Baths ⋅ 620092 MLS

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

1511 17th Ter, Key West

$1,375,000

Experience quintessential island living in this stunning waterfront townhome at Flagler's Landing, where sweeping Gulf views meet a central Key West location with private boat dockage. This elevated residence offers ~1,387 sq ft of living space with open water views from the main living areas, private balcony, and both upstairs bedrooms. Designed for effortless entertaining, the main level features an open-concept layout with spacious living and dining areas. The gourmet kitchen anchors the space with a custom coral stone island (seating for six), custom cabinetry, under-cabinet lighting, premium GE appliances, a six-burner range, and a new refrigerator. Warm bamboo flooring, recessed lighting, and a wide waterfront balcony create an ideal indoor-outdoor flow for sunsets and ocean breezes. A powder bath completes this level. A spiral staircase leads to the second level, where the hallway offers built-in bookshelves and a front-facing balcony. Both serene bedrooms feature walk-in closets and expansive water views. The primary and guest suites share a full bath with a glass walk-in shower, large vanity, and jacuzzi-style tub. Additional features include central A/C, ground-level covered parking, dedicated storage, a laundry area, and a ground-floor brick patio. For boating enthusiasts, the property includes a private shallow-draft slip suitable for a ~24 ft boat. Residents also enjoy community access to a heated concrete pool. Situated near beaches, dining, shopping, and marinas, this home is a rare opportunity to own a piece of paradise in an exclusive Key West enclave.

2 Beds ⋅ 2 Baths ⋅ 620045 MLS

Experience quintessential island living in this stunning waterfront townhome at Flagler's Landing, where sweeping Gulf views meet a central Key West location with private boat dockage. This elevated residence offers ~1,387 sq ft of living space with open water views from the main living areas, private balcony, and both upstairs bedrooms. Designed for effortless entertaining, the main level features an open-concept layout with spacious living and dining areas. The gourmet kitchen anchors the space with a custom coral stone island (seating for six), custom cabinetry, under-cabinet lighting, premium GE appliances, a six-burner range, and a new refrigerator. Warm bamboo flooring, recessed lighting, and a wide waterfront balcony create an ideal indoor-outdoor flow for sunsets and ocean breezes. A powder bath completes this level. A spiral staircase leads to the second level, where the hallway offers built-in bookshelves and a front-facing balcony. Both serene bedrooms feature walk-in closets and expansive water views. The primary and guest suites share a full bath with a glass walk-in shower, large vanity, and jacuzzi-style tub. Additional features include central A/C, ground-level covered parking, dedicated storage, a laundry area, and a ground-floor brick patio. For boating enthusiasts, the property includes a private shallow-draft slip suitable for a ~24 ft boat. Residents also enjoy community access to a heated concrete pool. Situated near beaches, dining, shopping, and marinas, this home is a rare opportunity to own a piece of paradise in an exclusive Key West enclave.

9 Mccoy Cir Unit 9, Key West

$1,249,000

Welcome to this beautifully renovated 3-bedroom, 2-bathroom home that perfectly blends modern finishes with warm, inviting living spaces. From the moment you arrive, you'll love the charming curb appeal, spacious covered front porch, and bright, airy interior filled with natural light. The heart of the home is the stunning chef's kitchen featuring an oversized quartz island, custom white shaker cabinetry, stainless steel appliances, abundant storage, and sleek designer finishes throughout. The open-concept layout flows seamlessly into the living and dining areas, making it ideal for entertaining and everyday living. The bedrooms offer comfort and flexibility, and both bathrooms have been thoughtfully updated with clean, modern touches. Located in a desirable neighborhood close to schools, shopping, dining, and local amenities, this move-in-ready home offers the perfect combination of style, comfort, and functionality.

3 Beds ⋅ 2 Baths ⋅ 620013 MLS

Welcome to this beautifully renovated 3-bedroom, 2-bathroom home that perfectly blends modern finishes with warm, inviting living spaces. From the moment you arrive, you'll love the charming curb appeal, spacious covered front porch, and bright, airy interior filled with natural light. The heart of the home is the stunning chef's kitchen featuring an oversized quartz island, custom white shaker cabinetry, stainless steel appliances, abundant storage, and sleek designer finishes throughout. The open-concept layout flows seamlessly into the living and dining areas, making it ideal for entertaining and everyday living. The bedrooms offer comfort and flexibility, and both bathrooms have been thoughtfully updated with clean, modern touches. Located in a desirable neighborhood close to schools, shopping, dining, and local amenities, this move-in-ready home offers the perfect combination of style, comfort, and functionality.

2116 Fogarty Ave, Key West

$2,500,000

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

8 Beds ⋅ 4 Baths ⋅ 619978 MLS

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

1409 Whalton St, Key West

$3,400,000

Located within the quiet, gated security of Old Town Villas, this 3-bedroom, 3-bathroom townhome offers a sophisticated, low-maintenance island retreat just one block off of Duval St. Built in 2017, with solid concrete construction, this exceptional residence blends contemporary elegance with a thoughtfully designed layout that maximizes privacy, comfort, and functionality. Stepping inside, the interior is highlighted by beautiful tile flooring that runs seamlessly throughout. The main level features an open-concept layout with a spacious living room and chef's kitchen complete with stainless steel appliances and granite peninsula offering abundant prep space and casual seating. Just off the kitchen, a flexible-use room can serve as a dining area or private bedroom suite, complete with its own ensuite bathroom. A hallmark of this property is the extensive amount of premium, custom-built cabinetry and shelving installed throughout by the California Closets, offering unparalleled storage and organization. For effortless luxury, a private elevator services all four levels, transporting you from the two-car garage all the way to the rooftop terrace. The third floor hosts two spacious ensuite bedrooms, each featuring private balconies and large walk-in closets complete with custom organizational systems. The top floor is dedicated to an open living room and office area--a flexible bonus space filled with natural light. Step out from this upper lounge onto the spectacular rooftop terrace, equipped with custom awnings for comfortable shade, designed to capture both sunrise serenity and vibrant sunset views. For total peace of mind, the home features impact-rated windows and doors throughout. Beyond your front door, enjoy the exclusive community amenities, including a large pool and cabana. Conveniently situated near the very best dining and boutiques Key West has to offer, this home delivers the ultimate blend of privacy, location and the coveted Key West lifestyle.

3 Beds ⋅ 3 Baths ⋅ 619959 MLS

Located within the quiet, gated security of Old Town Villas, this 3-bedroom, 3-bathroom townhome offers a sophisticated, low-maintenance island retreat just one block off of Duval St. Built in 2017, with solid concrete construction, this exceptional residence blends contemporary elegance with a thoughtfully designed layout that maximizes privacy, comfort, and functionality. Stepping inside, the interior is highlighted by beautiful tile flooring that runs seamlessly throughout. The main level features an open-concept layout with a spacious living room and chef's kitchen complete with stainless steel appliances and granite peninsula offering abundant prep space and casual seating. Just off the kitchen, a flexible-use room can serve as a dining area or private bedroom suite, complete with its own ensuite bathroom. A hallmark of this property is the extensive amount of premium, custom-built cabinetry and shelving installed throughout by the California Closets, offering unparalleled storage and organization. For effortless luxury, a private elevator services all four levels, transporting you from the two-car garage all the way to the rooftop terrace. The third floor hosts two spacious ensuite bedrooms, each featuring private balconies and large walk-in closets complete with custom organizational systems. The top floor is dedicated to an open living room and office area--a flexible bonus space filled with natural light. Step out from this upper lounge onto the spectacular rooftop terrace, equipped with custom awnings for comfortable shade, designed to capture both sunrise serenity and vibrant sunset views. For total peace of mind, the home features impact-rated windows and doors throughout. Beyond your front door, enjoy the exclusive community amenities, including a large pool and cabana. Conveniently situated near the very best dining and boutiques Key West has to offer, this home delivers the ultimate blend of privacy, location and the coveted Key West lifestyle.

141 Simonton St, Key West

$2,290,000

Four Apartment Property with Off Street Parking in a Prime Old Town Key West Location with LOTS of OPTIONS! 1104 Truman Avenue is a legal four-unit property with multiple use possibilities. Generous off-street parking; a rare and valuable feature in Old Town, enhances desirability for business and/or residential occupants. Classic Conch-style construction with covered porches adds to the property's island appeal and long-term value. The property currently consists of one 2BR/1BA unit and three 1BR/1BA units, all licensed rentals.. Flexible layout supports a variety of uses including long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with possible commercial use on the ground level and residential above. The property also offers the potential to be a duplex or reimagined as a spacious single-family residence. (Buyer to verify) This is an extremely well-located property with multiple use possibilities in a high-demand rental market.

5 Beds ⋅ 4 Baths ⋅ 619927 MLS

Four Apartment Property with Off Street Parking in a Prime Old Town Key West Location with LOTS of OPTIONS! 1104 Truman Avenue is a legal four-unit property with multiple use possibilities. Generous off-street parking; a rare and valuable feature in Old Town, enhances desirability for business and/or residential occupants. Classic Conch-style construction with covered porches adds to the property's island appeal and long-term value. The property currently consists of one 2BR/1BA unit and three 1BR/1BA units, all licensed rentals.. Flexible layout supports a variety of uses including long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with possible commercial use on the ground level and residential above. The property also offers the potential to be a duplex or reimagined as a spacious single-family residence. (Buyer to verify) This is an extremely well-located property with multiple use possibilities in a high-demand rental market.

1104 Truman Ave, Key West

$1,599,999

Endless possiblities! Two units to rent for the investor or live in one and produce income from the other unit. Downstairs you have a 3/1.5 with an open floor plan and covered porch with a patio. Upstairs you have a 2/1 floor plan and a mother in law lock out. All units have W/D hook ups and central air. Low maintence yardcare. Covered and dedicated parking with street parking as well. Great location close to downtown and the beaches. Owner is a general contractor and has lived in the home since 1972 and added the second story in 1994.

7 Beds ⋅ 5 Baths ⋅ 619911 MLS

Endless possiblities! Two units to rent for the investor or live in one and produce income from the other unit. Downstairs you have a 3/1.5 with an open floor plan and covered porch with a patio. Upstairs you have a 2/1 floor plan and a mother in law lock out. All units have W/D hook ups and central air. Low maintence yardcare. Covered and dedicated parking with street parking as well. Great location close to downtown and the beaches. Owner is a general contractor and has lived in the home since 1972 and added the second story in 1994.

1504 Flagler Ave, Key West

$6,200,000

You can renovate a house. You can't recreate the land. At the end of Sunrise Lane, on a 28,500 SF peninsula with water on three sides, sits one of the most compelling residential sites in Key West. 3750 Sunrise Lane combines land, privacy, waterfront, and scale in a way that simply does not come to market. This is not just a residence. It is the chance to build a significant Key West waterfront estate around the one thing that cannot be improved upon: the setting. Originally built in the 1950s and extensively expanded and rebuilt in 1999, the 5,378 SF residence offers five bedrooms and four and a half baths with heart pine floors, French doors, abundant natural light, and wide waterfront terraces. Three bedrooms and a spacious primary suite are on the first floor, while two upstairs guest bedrooms open to a covered balcony and rare widow's walk with sweeping water and protected land views. An expansive family-style kitchen and breakfast room anchors the home, complemented by a den with built-in wet bar and a separate studio and flex room offering multiple possibilities. Outside, the true scale of the property reveals itself. More than 3,200 SF of brick patios surround the large pool and tropical landscaping. Over 500 linear feet of seawall provides protected dockage, two boat lifts, and immediate deep-water access to the Atlantic and Gulf. A finished 828 SF, four-door garage completes this exceptional waterfront property. The residence is offered as a restoration and reimagination opportunity. It carries deferred maintenance, and with it the freedom to shape the property's next chapter rather than inherit someone else's. Restore its character. Rethink its spaces. Create a waterfront compound worthy of the site. 28,500 SF of land. Water on three sides. More than 500 feet of seawall. Protected dockage. Direct access to the Atlantic and Gulf. Homes can be transformed. Land like this cannot be recreated.

5 Beds ⋅ 5 Baths ⋅ 619886 MLS

You can renovate a house. You can't recreate the land. At the end of Sunrise Lane, on a 28,500 SF peninsula with water on three sides, sits one of the most compelling residential sites in Key West. 3750 Sunrise Lane combines land, privacy, waterfront, and scale in a way that simply does not come to market. This is not just a residence. It is the chance to build a significant Key West waterfront estate around the one thing that cannot be improved upon: the setting. Originally built in the 1950s and extensively expanded and rebuilt in 1999, the 5,378 SF residence offers five bedrooms and four and a half baths with heart pine floors, French doors, abundant natural light, and wide waterfront terraces. Three bedrooms and a spacious primary suite are on the first floor, while two upstairs guest bedrooms open to a covered balcony and rare widow's walk with sweeping water and protected land views. An expansive family-style kitchen and breakfast room anchors the home, complemented by a den with built-in wet bar and a separate studio and flex room offering multiple possibilities. Outside, the true scale of the property reveals itself. More than 3,200 SF of brick patios surround the large pool and tropical landscaping. Over 500 linear feet of seawall provides protected dockage, two boat lifts, and immediate deep-water access to the Atlantic and Gulf. A finished 828 SF, four-door garage completes this exceptional waterfront property. The residence is offered as a restoration and reimagination opportunity. It carries deferred maintenance, and with it the freedom to shape the property's next chapter rather than inherit someone else's. Restore its character. Rethink its spaces. Create a waterfront compound worthy of the site. 28,500 SF of land. Water on three sides. More than 500 feet of seawall. Protected dockage. Direct access to the Atlantic and Gulf. Homes can be transformed. Land like this cannot be recreated.

3750 Sunrise Ln, Key West