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

2 Beds ⋅ 4 Baths ⋅ 620515 MLS

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

33 Seaside S Ct, Key West

$849,000

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

3 Beds ⋅ 3 Baths ⋅ 620501 MLS

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

3712 Duck Ave, Key West

$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

$799,000

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

4 Beds ⋅ 2 Baths ⋅ 620461 MLS

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

1421-1425 2nd St, Key West

$979,000

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

4 Beds ⋅ 2 Baths ⋅ 620453 MLS

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

1500 5th St, Key West

$1,385,000

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

3 Beds ⋅ 2 Baths ⋅ 620448 MLS

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

2313 Fogarty Ave, Key West

$745,000

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 sitting under the stars, a private tropical oasis, or the ultimate vacation rental income producer, this backyard delivers the canvas. Off-street parking which 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 a lot of boxes! And Low Insurances!

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 sitting under the stars, a private tropical oasis, or the ultimate vacation rental income producer, this backyard delivers the canvas. Off-street parking which 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 a lot of boxes! And Low Insurances!

2005 Fogarty Ave, Key West

$3,500,000

Unbeatable Old Town Location only 3 properties to Duval Street! Live extraordinary in this Historic Victorian estate right in the middle of everything! 416 Fleming is a rare opportunity to own one of Key West's iconic and meticulously maintained properties. Featuring 6+ Off-Street Parking Spaces, 5 bedrooms and 5 bathrooms, this stunning residence embodies the Key West lifestyle with expansive wraparound porches, timeless architectural details, and an unbeatable Old Town location.Originally renovated in 2001 and thoughtfully updated through 2025, the property blends historic character with modern functionality.. Situated on a generous 6,700-square-foot lot, the property offers parking for up to nine vehicles--an exceptional amenity in Old Town Key West--with ample space remaining for the addition of a private pool. Enjoy picturesque views of the surrounding historic district from the expansive porches while embracing the relaxed island atmosphere that defines Key West living. A unique and valuable feature of the property is its 15,000-gallon underground rainwater harvesting cistern, measuring approximately 11' x 13' x 19'. Designed and constructed by a retired Boeing piping engineer, the system incorporates a dual-chamber design, allowing one chamber to remain in service while the other is isolated for inspection, cleaning, and maintenance. The home's roof drainage system has been professionally plumbed to collect and direct rainwater into the cistern, with a diverter valve that allows water to be routed either into storage or discharged into the yard. With the addition of a pump, this impressive system can be reactivated for irrigation and other sustainable water-management uses.Offering historic significance, income potential, abundant parking, modern updates, and a truly rare engineering feature, this exceptional property is a one-of-a-kind opportunity in the heart of Old Town.Corner Lane Lot: dimensions 50' x 134 Bike Rack Stays!

5 Beds ⋅ 5 Baths ⋅ 620434 MLS

Unbeatable Old Town Location only 3 properties to Duval Street! Live extraordinary in this Historic Victorian estate right in the middle of everything! 416 Fleming is a rare opportunity to own one of Key West's iconic and meticulously maintained properties. Featuring 6+ Off-Street Parking Spaces, 5 bedrooms and 5 bathrooms, this stunning residence embodies the Key West lifestyle with expansive wraparound porches, timeless architectural details, and an unbeatable Old Town location.Originally renovated in 2001 and thoughtfully updated through 2025, the property blends historic character with modern functionality.. Situated on a generous 6,700-square-foot lot, the property offers parking for up to nine vehicles--an exceptional amenity in Old Town Key West--with ample space remaining for the addition of a private pool. Enjoy picturesque views of the surrounding historic district from the expansive porches while embracing the relaxed island atmosphere that defines Key West living. A unique and valuable feature of the property is its 15,000-gallon underground rainwater harvesting cistern, measuring approximately 11' x 13' x 19'. Designed and constructed by a retired Boeing piping engineer, the system incorporates a dual-chamber design, allowing one chamber to remain in service while the other is isolated for inspection, cleaning, and maintenance. The home's roof drainage system has been professionally plumbed to collect and direct rainwater into the cistern, with a diverter valve that allows water to be routed either into storage or discharged into the yard. With the addition of a pump, this impressive system can be reactivated for irrigation and other sustainable water-management uses.Offering historic significance, income potential, abundant parking, modern updates, and a truly rare engineering feature, this exceptional property is a one-of-a-kind opportunity in the heart of Old Town.Corner Lane Lot: dimensions 50' x 134 Bike Rack Stays!

416 Fleming St, Key West

$799,000

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

2 Beds ⋅ 2 Baths ⋅ 620402 MLS

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

3715 Flagler Ave, Key West

$1,195,000

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

2 Beds ⋅ 2 Baths ⋅ 620360 MLS

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

1126 Grinnell St, Key West

$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

$3,795,000

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

$1,850,000

701 Simonton Street offers a standout commercial presence in the heart of Old Town Key West, positioned on the highly visible corner of Simonton and Angela Streets. This single-story commercial building features 1,745 square feet of functional interior space on a 6,510 square foot lot, with 8+ off-street parking spaces and a convenient drive-through parking layout. The existing floor plan includes five private offices, a reception/lobby area, storage, central air conditioning, and a security system, creating flexibility for many uses. Frame construction, a metal roof, and an X flood zone location add practical appeal for an owner-user or investor. Located in the Historic Neighborhood Commercial (HNC-1) zoning district, this corner property offers strong visibility, convenient access, and rare on-site parking in one of Key West's most established and walkable Old Town locations. Located in the Transient rental License Transfer receivership zone as shown in the map attached.

3 Baths ⋅ 620342 MLS

701 Simonton Street offers a standout commercial presence in the heart of Old Town Key West, positioned on the highly visible corner of Simonton and Angela Streets. This single-story commercial building features 1,745 square feet of functional interior space on a 6,510 square foot lot, with 8+ off-street parking spaces and a convenient drive-through parking layout. The existing floor plan includes five private offices, a reception/lobby area, storage, central air conditioning, and a security system, creating flexibility for many uses. Frame construction, a metal roof, and an X flood zone location add practical appeal for an owner-user or investor. Located in the Historic Neighborhood Commercial (HNC-1) zoning district, this corner property offers strong visibility, convenient access, and rare on-site parking in one of Key West's most established and walkable Old Town locations. Located in the Transient rental License Transfer receivership zone as shown in the map attached.

701 Simonton 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

$439,000

Lowest-Priced Commercial Retail Space in Old Town -- Offering an 8% CAP Rate. Positioned along high-visibility Truman Avenue, this commercial condominium delivers exceptional exposure in the heart of Key West, surrounded by a vibrant mix of shops, restaurants, residences, and historic attractions. The flexible space is well suited for retail, professional office, salon, studio, or gallery use. Recent improvements include new flooring, fresh interior paint, and a renovated bathroom, creating a clean, turnkey environment ready for immediate occupancy. Strong pedestrian and vehicle traffic add to the appeal of this established Old Town commercial corridor. HOA is $576/month and includes building insurance, exterior maintenance, and common-area care. An outstanding opportunity for an owner-user or investor seeking an accessible entry point into the Old Town commercial market. Schedule your private showing today.

1 Baths ⋅ 620196 MLS

Lowest-Priced Commercial Retail Space in Old Town -- Offering an 8% CAP Rate. Positioned along high-visibility Truman Avenue, this commercial condominium delivers exceptional exposure in the heart of Key West, surrounded by a vibrant mix of shops, restaurants, residences, and historic attractions. The flexible space is well suited for retail, professional office, salon, studio, or gallery use. Recent improvements include new flooring, fresh interior paint, and a renovated bathroom, creating a clean, turnkey environment ready for immediate occupancy. Strong pedestrian and vehicle traffic add to the appeal of this established Old Town commercial corridor. HOA is $576/month and includes building insurance, exterior maintenance, and common-area care. An outstanding opportunity for an owner-user or investor seeking an accessible entry point into the Old Town commercial market. Schedule your private showing today.

1012 Truman Ave Unit 6, Key West

$3,295,000

This large restaurant/bar in the heart of downtown Key West is presently rented for $18,000 NNN a month with over three years remaining on the lease. The location is excellent and the building has an effective rebuild date of 2005. The present tenant may be negotiable. Buy a piece of Key West. Call today.

2 Baths ⋅ 620183 MLS

This large restaurant/bar in the heart of downtown Key West is presently rented for $18,000 NNN a month with over three years remaining on the lease. The location is excellent and the building has an effective rebuild date of 2005. The present tenant may be negotiable. Buy a piece of Key West. Call today.

404 Southard St Unit 2, Key West

$1,799,000

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

3 Beds ⋅ 3 Baths ⋅ 620176 MLS

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

2101 Harris Ave, Key West

$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

$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

$1,179,000

OPEN HOUSE 10/24 from 12pM to 2PM 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 10/24 from 12pM to 2PM 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

$2,434,000

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

3 Beds ⋅ 4 Baths ⋅ 620092 MLS

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

1511 17th Ter, Key West

1901 S Roosevelt Blvd Unit 401S, Key West

$890,000

Major price improvement for an amazing full ocean view penthouse unit! Presumably the best view in the preferred South Wing of La Brisa Condominiums, enjoy a panoramic view of the Atlantic Ocean and all the activity and fun of Smather's Beach. Ready for your improvements, the condo has a modern open floor plan, spacious master suite with a large walk in closet, and a private balcony to enjoy the view. There is ultimate convenience from the condo unit to the assigned covered parking and storage. Meticulously maintained with professional on site management, La Brisa Condominiums feature superb amenities like a heated swimming pool, hot tub, saunas, a clubhouse, lighted tennis/pickleball court, car wash and grilling area. There is even a complimentary EV charging station. The home is available for your immediate occupancy, with no leases in place or follow on seller occupancy requirements. Centrally located on Key West, with bike paths and public transportation nearby, the Southmost City is yours to explore. Photos depicting furnishings have been virtually staged. Now priced for only $890,000!

2 Beds ⋅ 2 Baths ⋅ 620086 MLS

Major price improvement for an amazing full ocean view penthouse unit! Presumably the best view in the preferred South Wing of La Brisa Condominiums, enjoy a panoramic view of the Atlantic Ocean and all the activity and fun of Smather's Beach. Ready for your improvements, the condo has a modern open floor plan, spacious master suite with a large walk in closet, and a private balcony to enjoy the view. There is ultimate convenience from the condo unit to the assigned covered parking and storage. Meticulously maintained with professional on site management, La Brisa Condominiums feature superb amenities like a heated swimming pool, hot tub, saunas, a clubhouse, lighted tennis/pickleball court, car wash and grilling area. There is even a complimentary EV charging station. The home is available for your immediate occupancy, with no leases in place or follow on seller occupancy requirements. Centrally located on Key West, with bike paths and public transportation nearby, the Southmost City is yours to explore. Photos depicting furnishings have been virtually staged. Now priced for only $890,000!

1901 S Roosevelt Blvd Unit 401S, Key West

$1,250,000

With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting one unit while living in the other. Set on a 5,000 sq ft lot, the property is surrounded by lush, mature tropical landscaping with a wide variety of plants and palms, creating a private, shaded, treehouse-like setting filled with natural light. Two large screened porches and additional open-air spaces provide ideal indoor-outdoor living, while an outdoor shower enhances the island lifestyle. The home has been thoughtfully updated and well cared for, featuring Mitsubishi mini-split A/C systems in both units, a new hot water heater, new ceiling fans, impact windows upstairs, new gutters, updated appliances, and soft-close cabinetry. Interior finishes include a mix of pine, vinyl, and concrete flooring, along with stainless, Formica, and butcher block countertops. Both units offer full bathrooms with tubs. Additional highlights include two off-street parking spaces, low-maintenance grounds, and multiple windows throughout for abundant natural light and airflow. Located in desirable Midtown East, just minutes from everything Key West has to offer, this is a versatile, income-producing property with strong upside potential.

2 Beds ⋅ 2 Baths ⋅ 620075 MLS

With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting one unit while living in the other. Set on a 5,000 sq ft lot, the property is surrounded by lush, mature tropical landscaping with a wide variety of plants and palms, creating a private, shaded, treehouse-like setting filled with natural light. Two large screened porches and additional open-air spaces provide ideal indoor-outdoor living, while an outdoor shower enhances the island lifestyle. The home has been thoughtfully updated and well cared for, featuring Mitsubishi mini-split A/C systems in both units, a new hot water heater, new ceiling fans, impact windows upstairs, new gutters, updated appliances, and soft-close cabinetry. Interior finishes include a mix of pine, vinyl, and concrete flooring, along with stainless, Formica, and butcher block countertops. Both units offer full bathrooms with tubs. Additional highlights include two off-street parking spaces, low-maintenance grounds, and multiple windows throughout for abundant natural light and airflow. Located in desirable Midtown East, just minutes from everything Key West has to offer, this is a versatile, income-producing property with strong upside potential.

1911 Seidenberg Ave, 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

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