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Great opportunity to own your own home or have an excellent source of rental income. Currently the least expensive detached residence in Key West. Freshly painted interior and new AC. This renovated one bedroom condo cottage overlooking the large communal pool is just one block to vibrant White St with its cafes and restaurants, gourmet food stores, galleries and yoga studios. A short walk or bike ride to the beaches and the heart of Old Town, the Historic Seaport and Duval Street.....The compound has a large pool shared with only 3 other condos. There are lovely landscaped communal areas with fruit trees, sun decks, lounge chairs and outdoor dining areas.....Recent improvements to the home include a metal roof, impact windows plus additional storm shutters. The condo has one bedroom, a full bath with shower above, full kitchen and double doors leading to the pool and patio area.

1 Beds ⋅ 1 Baths ⋅ 621579 MLS

Great opportunity to own your own home or have an excellent source of rental income. Currently the least expensive detached residence in Key West. Freshly painted interior and new AC. This renovated one bedroom condo cottage overlooking the large communal pool is just one block to vibrant White St with its cafes and restaurants, gourmet food stores, galleries and yoga studios. A short walk or bike ride to the beaches and the heart of Old Town, the Historic Seaport and Duval Street.....The compound has a large pool shared with only 3 other condos. There are lovely landscaped communal areas with fruit trees, sun decks, lounge chairs and outdoor dining areas.....Recent improvements to the home include a metal roof, impact windows plus additional storm shutters. The condo has one bedroom, a full bath with shower above, full kitchen and double doors leading to the pool and patio area.

1318 Duncan St Unit APT 3, Key West

$3,795,000

Rare Old Town mixed-use opportunity at 1011 Whitehead Street, just steps from Duval Street, the Key West Lighthouse and the Hemingway Home. This historic property features three beautifully updated, furnished one-bedroom residences, each with its own kitchen and transient rental license, allowing the units to be rented individually or together. Private patios and balconies add classic Key West charm, while a street-level commercial storefront provides an additional income-producing component. With three valuable transient licenses, flexible use and an iconic walkable location, this is a unique opportunity to own a distinctive piece of Key West.

3 Beds ⋅ 5 Baths ⋅ 621561 MLS

Rare Old Town mixed-use opportunity at 1011 Whitehead Street, just steps from Duval Street, the Key West Lighthouse and the Hemingway Home. This historic property features three beautifully updated, furnished one-bedroom residences, each with its own kitchen and transient rental license, allowing the units to be rented individually or together. Private patios and balconies add classic Key West charm, while a street-level commercial storefront provides an additional income-producing component. With three valuable transient licenses, flexible use and an iconic walkable location, this is a unique opportunity to own a distinctive piece of Key West.

1011 Whitehead St, Key West

$6,449,000

Some Key West homes are historic because they are old. 1311 Truman Avenue is historic because of who built it, who gathered within its walls, and who saved it. Its front door came from the Old Southernmost House. Past it, Dade County pine flows through every room, chandeliers light high ceilings on both floors, and the original staircase still rises where it has stood for more than a century. A second staircase toward the rear, also original to the house, recalls the scale on which it was built. Outside, sweeping double-story porches wrap the Victorian-influenced home, set on a third of an acre. The house was built at the turn of the twentieth century by Benjamin Douglas Trevor and his wife, Mary Fogarty Trevor. Mr. Trevor founded Key West's first Steam Laundry and in 1903 became Mayor of Key West. In the decades that followed, the house became home to the Key West Woman's Club and later served as a church. In 1975 two prominent local antique dealers purchased it and returned it to its original glory, and their work received the first award for an excellent restoration given by the Old Island Restoration Foundation. That restoration still defines the house. The original windows remain, along with the moldings and trim, and verandas open to the grounds from both floors. A large covered porch offers room for both dining and living, with views over the refinished pool and the guest cottage. Over the past decade, the current owners have carried that stewardship forward. A magnificent tropical garden and a stunning pool now grace the 14,490-square-foot lot. Every bathroom has been updated and finished in a fine selection of marble, granite, and quartz, and the kitchen and appliances have been updated, bringing modern comfort to a house whose history remains its defining feature. Built by a mayor, gathered in by the Woman's Club, and saved by the restoration that set the standard for Old Town, 1311 Truman Avenue is ready for the next chapter of its story.

7 Beds ⋅ 8 Baths ⋅ 621544 MLS

Some Key West homes are historic because they are old. 1311 Truman Avenue is historic because of who built it, who gathered within its walls, and who saved it. Its front door came from the Old Southernmost House. Past it, Dade County pine flows through every room, chandeliers light high ceilings on both floors, and the original staircase still rises where it has stood for more than a century. A second staircase toward the rear, also original to the house, recalls the scale on which it was built. Outside, sweeping double-story porches wrap the Victorian-influenced home, set on a third of an acre. The house was built at the turn of the twentieth century by Benjamin Douglas Trevor and his wife, Mary Fogarty Trevor. Mr. Trevor founded Key West's first Steam Laundry and in 1903 became Mayor of Key West. In the decades that followed, the house became home to the Key West Woman's Club and later served as a church. In 1975 two prominent local antique dealers purchased it and returned it to its original glory, and their work received the first award for an excellent restoration given by the Old Island Restoration Foundation. That restoration still defines the house. The original windows remain, along with the moldings and trim, and verandas open to the grounds from both floors. A large covered porch offers room for both dining and living, with views over the refinished pool and the guest cottage. Over the past decade, the current owners have carried that stewardship forward. A magnificent tropical garden and a stunning pool now grace the 14,490-square-foot lot. Every bathroom has been updated and finished in a fine selection of marble, granite, and quartz, and the kitchen and appliances have been updated, bringing modern comfort to a house whose history remains its defining feature. Built by a mayor, gathered in by the Woman's Club, and saved by the restoration that set the standard for Old Town, 1311 Truman Avenue is ready for the next chapter of its story.

1311 Truman Ave, Key West

$1,795,000

This charming Legal Duplex located historical Old Town district with 2 COVERED CAR PARKING in your own backyard. 2 bed 2 bath downstairs and 2 bed 1 bath upstairs. Fantastic Front Porch and Upstairs Balcony. Just Blocks away from DUVAL street .

4 Beds ⋅ 3 Baths ⋅ 621528 MLS

This charming Legal Duplex located historical Old Town district with 2 COVERED CAR PARKING in your own backyard. 2 bed 2 bath downstairs and 2 bed 1 bath upstairs. Fantastic Front Porch and Upstairs Balcony. Just Blocks away from DUVAL street .

809 Fleming St, Key West

$3,700,000

This home has everything you need to enjoy the Key West lifestyle! With approximately 3,000 sq. ft. of living space and a 6-foot privacy fence surrounding the large property, there's plenty of room to entertain both inside and out. The kitchen features Sub-Zero and KitchenAid appliances and flows right into the main living area, making it perfect for everyday living and entertaining. The home also offers a full laundry room plus a bonus mudroom for extra storage and convenience. Outside is where this home really shines! Enjoy a covered deck area, large heated pool, and boating canal with a 30,000-lb. boat lift and ice machine. You're just minutes from the channel--no idling 1-2 miles down the canal like with many other homes. There's also covered parking and a garage with plenty of room to store all your toys. Best of all, this home is being sold turnkey and even includes a golf cart! Come see what sets this home apart from anything else on the market!

5 Beds ⋅ 5 Baths ⋅ 621515 MLS

This home has everything you need to enjoy the Key West lifestyle! With approximately 3,000 sq. ft. of living space and a 6-foot privacy fence surrounding the large property, there's plenty of room to entertain both inside and out. The kitchen features Sub-Zero and KitchenAid appliances and flows right into the main living area, making it perfect for everyday living and entertaining. The home also offers a full laundry room plus a bonus mudroom for extra storage and convenience. Outside is where this home really shines! Enjoy a covered deck area, large heated pool, and boating canal with a 30,000-lb. boat lift and ice machine. You're just minutes from the channel--no idling 1-2 miles down the canal like with many other homes. There's also covered parking and a garage with plenty of room to store all your toys. Best of all, this home is being sold turnkey and even includes a golf cart! Come see what sets this home apart from anything else on the market!

3728 Flagler Ave, Key West

$1,350,000

DEEDED BOAT SLIP ON ISLAND! A standout waterfront opportunity in Key West, 5 McCoy Cir #5 offers the kind of coastal living that is hard to find: a townhome with a deeded boat slip, open water views, ample parking, and direct sightlines to your slip from the balcony. From the moment you enter, the unobstructed water views set the tone, creating a bright and relaxed setting across every level of the home. Designed for easy living, this 1,387 sq. ft. townhome features a smart three-level layout with generous storage, covered parking, and multiple outdoor spaces. The main living level includes an open kitchen and living area with a convenient half bath, all positioned to take full advantage of the wide water views. Step out to the large balcony and enjoy a front-row view of your boat slip, the surrounding water, and the open horizon beyond. The top floor offers two bedrooms, each with its own ensuite bathroom, creating comfortable private spaces with a clean and functional layout. Below, the covered garage area provides ample storage for boating gear, fishing equipment, bikes, tools, and everyday essentials. Plenty of storage to store your fresh catch, stone crabs, drinks, and supplies after a day on the water. The deeded boat slip is a true highlight, offering the ability to walk directly to your boat and enjoy the water with ease. The slip can comfortably fit a 25-foot boat with dual engines, making this a special option for those who value direct water access. A private patio adds another outdoor area to relax, rinse off, or organize gear before and after time on the boat. With dedicated parking, plenty of storage options, open water views from every level, and HOA coverage that includes insurance, this property brings together convenience, function, and the Key West waterfront lifestyle in one remarkable property. Come check it out by land or by boat -- pull up to the slip and we'll give you a tour!

2 Beds ⋅ 3 Baths ⋅ 621523 MLS

DEEDED BOAT SLIP ON ISLAND! A standout waterfront opportunity in Key West, 5 McCoy Cir #5 offers the kind of coastal living that is hard to find: a townhome with a deeded boat slip, open water views, ample parking, and direct sightlines to your slip from the balcony. From the moment you enter, the unobstructed water views set the tone, creating a bright and relaxed setting across every level of the home. Designed for easy living, this 1,387 sq. ft. townhome features a smart three-level layout with generous storage, covered parking, and multiple outdoor spaces. The main living level includes an open kitchen and living area with a convenient half bath, all positioned to take full advantage of the wide water views. Step out to the large balcony and enjoy a front-row view of your boat slip, the surrounding water, and the open horizon beyond. The top floor offers two bedrooms, each with its own ensuite bathroom, creating comfortable private spaces with a clean and functional layout. Below, the covered garage area provides ample storage for boating gear, fishing equipment, bikes, tools, and everyday essentials. Plenty of storage to store your fresh catch, stone crabs, drinks, and supplies after a day on the water. The deeded boat slip is a true highlight, offering the ability to walk directly to your boat and enjoy the water with ease. The slip can comfortably fit a 25-foot boat with dual engines, making this a special option for those who value direct water access. A private patio adds another outdoor area to relax, rinse off, or organize gear before and after time on the boat. With dedicated parking, plenty of storage options, open water views from every level, and HOA coverage that includes insurance, this property brings together convenience, function, and the Key West waterfront lifestyle in one remarkable property. Come check it out by land or by boat -- pull up to the slip and we'll give you a tour!

5 Mccoy Cir Unit # 5, Key West

$3,750,000

Exceptional Key West Investment Opportunity with 3 Transient Licenses. The property consists of four private one bedrooms, one bath units, each featuring its own kitchen, living area, bedroom, and full bathroom. Most importantly, three of the four units benefit from transient rental licenses allowing nightly rentals, an increasingly rare and valuable asset in the Key West market. The fourth unit is currently rented monthly. Guests enjoy a shared private courtyard with a swimming pool, creating an inviting tropical setting and a desirable amenity for vacation renters. The property also offers three parking spaces, an added convenience in Key West. Renovated in 2018, the units blend classic Key West character with modern updates. Features include Dade County pine, engineered wood flooring, granite countertops, updated kitchen cabinetry and appliances, along with updated plumbing and electrical systems. Each unit is designed to operate independently, making the property well suited for continued use as an income producing investment.

4 Beds ⋅ 4 Baths ⋅ 621522 MLS

Exceptional Key West Investment Opportunity with 3 Transient Licenses. The property consists of four private one bedrooms, one bath units, each featuring its own kitchen, living area, bedroom, and full bathroom. Most importantly, three of the four units benefit from transient rental licenses allowing nightly rentals, an increasingly rare and valuable asset in the Key West market. The fourth unit is currently rented monthly. Guests enjoy a shared private courtyard with a swimming pool, creating an inviting tropical setting and a desirable amenity for vacation renters. The property also offers three parking spaces, an added convenience in Key West. Renovated in 2018, the units blend classic Key West character with modern updates. Features include Dade County pine, engineered wood flooring, granite countertops, updated kitchen cabinetry and appliances, along with updated plumbing and electrical systems. Each unit is designed to operate independently, making the property well suited for continued use as an income producing investment.

1501 Truman Ave, Key West

$5,200,000

Where Casa Marina Charm Meets Modern Island Living. Set on an expansive 10,000 sq. ft corner lot in prestigious Casa Marina, one of Key West's most sought-after neighborhoods, this fully renovated 4-bedroom, 3-bath residence offers nearly 2,100 sq. ft of thoughtfully designed living space just moments from the Atlantic shoreline and the charm of Old Town. A comprehensive 2020 renovation transformed the home from top to bottom, delivering vaulted ceilings, energy-efficient LED lighting, and all-new hurricane-rated impact windows and doors that fill the interior with natural light. The open floor plan flows effortlessly between living, dining, and kitchen spaces, making it ideal for both everyday living and entertaining. At the heart of the home, the chef's kitchen features top-of-the-line Dacor appliances and custom bespoke cabinetry. The private primary suite is tucked at the rear of the home with an ensuite bath and sliding glass doors that open directly to the lanai. Each additional bedroom includes built-in closets, offering comfort and flexibility for guests or a home office. Outdoors, a custom heated in-ground pool with a soothing water feature is surrounded by elegant travertine decking and a spacious covered patio, creating a private tropical retreat for relaxing or hosting under the Key West sky. The low-maintenance front yard features artificial turf and landscape lighting that showcases the tropical foliage after dark. Peace of mind comes standard with a whole-house generator, 2-zone central A/C with linear vents, and a new standing seam metal roof that may qualify for wind insurance credits. A rare one-car garage and ample off-street parking complete this exceptional Casa Marina offering.

4 Beds ⋅ 3 Baths ⋅ 621521 MLS

Where Casa Marina Charm Meets Modern Island Living. Set on an expansive 10,000 sq. ft corner lot in prestigious Casa Marina, one of Key West's most sought-after neighborhoods, this fully renovated 4-bedroom, 3-bath residence offers nearly 2,100 sq. ft of thoughtfully designed living space just moments from the Atlantic shoreline and the charm of Old Town. A comprehensive 2020 renovation transformed the home from top to bottom, delivering vaulted ceilings, energy-efficient LED lighting, and all-new hurricane-rated impact windows and doors that fill the interior with natural light. The open floor plan flows effortlessly between living, dining, and kitchen spaces, making it ideal for both everyday living and entertaining. At the heart of the home, the chef's kitchen features top-of-the-line Dacor appliances and custom bespoke cabinetry. The private primary suite is tucked at the rear of the home with an ensuite bath and sliding glass doors that open directly to the lanai. Each additional bedroom includes built-in closets, offering comfort and flexibility for guests or a home office. Outdoors, a custom heated in-ground pool with a soothing water feature is surrounded by elegant travertine decking and a spacious covered patio, creating a private tropical retreat for relaxing or hosting under the Key West sky. The low-maintenance front yard features artificial turf and landscape lighting that showcases the tropical foliage after dark. Peace of mind comes standard with a whole-house generator, 2-zone central A/C with linear vents, and a new standing seam metal roof that may qualify for wind insurance credits. A rare one-car garage and ample off-street parking complete this exceptional Casa Marina offering.

1100 Johnson St, Key West

$749,000

Updated CBS Duplex on Oversized Stock Island Lot - Ready Now Opportunity is knocking on Stock Island! This well-maintained CBS duplex offers 4 bedrooms and 2 bathrooms on a generously sized lot, with abundant room to park and store vehicles, boats, trailers, and work equipment, a rare find this close to Key West. Both kitchens and both bathrooms have been tastefully updated, so you can move in or rent out without lifting a finger. Solid concrete block construction provides durability and peace of mind in the Keys climate. The yard is a true blank canvas, ready for your vision, whether that's a garden retreat, outdoor entertaining space, or added storage. Live in one side and rent the other, or add a strong income property to your portfolio. Available for immediate occupancy. Just minutes from Key West dining, marinas, and amenities.

4 Beds ⋅ 2 Baths ⋅ 621519 MLS

Updated CBS Duplex on Oversized Stock Island Lot - Ready Now Opportunity is knocking on Stock Island! This well-maintained CBS duplex offers 4 bedrooms and 2 bathrooms on a generously sized lot, with abundant room to park and store vehicles, boats, trailers, and work equipment, a rare find this close to Key West. Both kitchens and both bathrooms have been tastefully updated, so you can move in or rent out without lifting a finger. Solid concrete block construction provides durability and peace of mind in the Keys climate. The yard is a true blank canvas, ready for your vision, whether that's a garden retreat, outdoor entertaining space, or added storage. Live in one side and rent the other, or add a strong income property to your portfolio. Available for immediate occupancy. Just minutes from Key West dining, marinas, and amenities.

6415 2nd Ter, Key West

$1,399,000

Situated on a spacious corner lot in desirable Midtown West, 1221 Ashby Street offers the perfect blend of comfort, privacy, and island living. The main residence features 2 bedrooms, 2 bathrooms, and inviting living spaces, while a separate 1-bedroom, 1-bathroom poolside cottage provides additional flexibility for guests or extended family. Together, the two structures offer 1,374 square feet of living space. The oversized outdoor area is designed for enjoying the Key West lifestyle, featuring a large swimming pool, spacious decking, lounge chairs, umbrellas, and an outdoor dining area ideal for entertaining. Covered off-street parking adds convenience to this property's many desirable features. Recently updated and ready for its next owner, this property offers a fantastic opportunity to enjoy island living just minutes from Key West's famous restaurants, bars, and attractions.

3 Beds ⋅ 3 Baths ⋅ 621518 MLS

Situated on a spacious corner lot in desirable Midtown West, 1221 Ashby Street offers the perfect blend of comfort, privacy, and island living. The main residence features 2 bedrooms, 2 bathrooms, and inviting living spaces, while a separate 1-bedroom, 1-bathroom poolside cottage provides additional flexibility for guests or extended family. Together, the two structures offer 1,374 square feet of living space. The oversized outdoor area is designed for enjoying the Key West lifestyle, featuring a large swimming pool, spacious decking, lounge chairs, umbrellas, and an outdoor dining area ideal for entertaining. Covered off-street parking adds convenience to this property's many desirable features. Recently updated and ready for its next owner, this property offers a fantastic opportunity to enjoy island living just minutes from Key West's famous restaurants, bars, and attractions.

1221 Ashby St, Key West

$1,895,000

Ideally located just two blocks from the beach, this beautifully renovated Key West residence blends island living, modern comfort, and plenty of space to make it your own. Set on an expansive 6,000-square-foot corner lot, the home offers more than 2,200 square feet of living space in one of Key West's most desirable residential neighborhoods. Walk to the beach and iconic White Street Pier, along with nearby pickleball courts, playgrounds, the weekly artisan market, Bayview Park, and Fausto's Food Palace. Local favorites including Salute! On The Beach and Louie's Backyard are also just minutes away. At the heart of the home is a brand-new kitchen featuring custom cabinetry, stainless steel appliances, quartz countertops, and a fresh, sophisticated finish. Thoughtful renovations throughout provide a beautifully updated foundation while leaving room for the next owners to add their own personal style. Major improvements include a new roof, impact-rated windows and doors, updated HVAC, lighting, interior and exterior paint, water heater, and other essential systems--offering peace of mind with many of the home's major components already addressed. The property also has no history of flooding, an especially valuable feature for island living. Outside, the oversized corner lot offers exceptional potential to create a private Key West retreat, with ample room for a pool, tropical landscaping, and outdoor entertaining areas. Ample street parking is available, along with off-street parking suitable for a small sedan or golf cart. With more than 2,200 square feet of living space, a substantial corner lot, extensive improvements, and an exceptional location just two blocks from the Atlantic, this Rose Street residence presents a rare opportunity to create your own piece of Key West paradise.

4 Beds ⋅ 4 Baths ⋅ 621516 MLS

Ideally located just two blocks from the beach, this beautifully renovated Key West residence blends island living, modern comfort, and plenty of space to make it your own. Set on an expansive 6,000-square-foot corner lot, the home offers more than 2,200 square feet of living space in one of Key West's most desirable residential neighborhoods. Walk to the beach and iconic White Street Pier, along with nearby pickleball courts, playgrounds, the weekly artisan market, Bayview Park, and Fausto's Food Palace. Local favorites including Salute! On The Beach and Louie's Backyard are also just minutes away. At the heart of the home is a brand-new kitchen featuring custom cabinetry, stainless steel appliances, quartz countertops, and a fresh, sophisticated finish. Thoughtful renovations throughout provide a beautifully updated foundation while leaving room for the next owners to add their own personal style. Major improvements include a new roof, impact-rated windows and doors, updated HVAC, lighting, interior and exterior paint, water heater, and other essential systems--offering peace of mind with many of the home's major components already addressed. The property also has no history of flooding, an especially valuable feature for island living. Outside, the oversized corner lot offers exceptional potential to create a private Key West retreat, with ample room for a pool, tropical landscaping, and outdoor entertaining areas. Ample street parking is available, along with off-street parking suitable for a small sedan or golf cart. With more than 2,200 square feet of living space, a substantial corner lot, extensive improvements, and an exceptional location just two blocks from the Atlantic, this Rose Street residence presents a rare opportunity to create your own piece of Key West paradise.

1423 Rose St, Key West

$1,699,000

Enjoy Old Town Key West living just two blocks from Duval Street at 615 Amelia Street. This two-bedroom, two-and-a-half-bath single family home offers inviting indoor and outdoor spaces centered around a tropical pool courtyard. The open living and dining area features wide sliding glass doors leading to a covered deck, creating an easy flow for relaxing or entertaining. Beyond the deck, lush landscaping surrounds the pool and patio, with space for outdoor dining and lounging. The kitchen offers white cabinetry, ample storage, and a windowed breakfast nook, while a vaulted ceiling gives one of the bedrooms an airy feel. The roof and windows were upgraded in 2024. Located in Flood Zone X, annual insurance costs are approximately $6,407. From morning coffee on the deck to afternoons beside the pool, this home brings together comfortable living and a convenient Old Town location.

2 Beds ⋅ 3 Baths ⋅ 621509 MLS

Enjoy Old Town Key West living just two blocks from Duval Street at 615 Amelia Street. This two-bedroom, two-and-a-half-bath single family home offers inviting indoor and outdoor spaces centered around a tropical pool courtyard. The open living and dining area features wide sliding glass doors leading to a covered deck, creating an easy flow for relaxing or entertaining. Beyond the deck, lush landscaping surrounds the pool and patio, with space for outdoor dining and lounging. The kitchen offers white cabinetry, ample storage, and a windowed breakfast nook, while a vaulted ceiling gives one of the bedrooms an airy feel. The roof and windows were upgraded in 2024. Located in Flood Zone X, annual insurance costs are approximately $6,407. From morning coffee on the deck to afternoons beside the pool, this home brings together comfortable living and a convenient Old Town location.

615 Amelia St, Key West

$1,999,999

KEY WEST LIFESTYLE !!!!!! Prime Old Town Duplex Just Two Blocks Off Duval. (each unit also available for sale ) Exceptional investment and island living opportunity in the heart of Old Town Key West. 220 Angela Street offers a classic two-story Conch duplex featuring two private residences (Units A & B), each designed for effortless indoor-outdoor living. Both units boast functional multi-level layouts, central A/C, dedicated interior laundry, and expansive upstairs and downstairs wrap-around porches overlooking lush tropical surroundings. The fully fenced grounds provide a private, shaded yard and the ultimate Old Town luxury: rare off-street parking. Live in one unit while generating passive income from the other, or hold as an income-producing multi-family portfolio piece in one of the nation's strongest rental markets. Situated on a quiet residential stretch just steps from Duval Street, Bahama Village dining, Fort Zachary Taylor State Park & Beach, and the Truman Waterfront. KEYWEST EVENTS : https://www.keywestchamber.org/visit.html

4 Beds ⋅ 4 Baths ⋅ 621502 MLS

KEY WEST LIFESTYLE !!!!!! Prime Old Town Duplex Just Two Blocks Off Duval. (each unit also available for sale ) Exceptional investment and island living opportunity in the heart of Old Town Key West. 220 Angela Street offers a classic two-story Conch duplex featuring two private residences (Units A & B), each designed for effortless indoor-outdoor living. Both units boast functional multi-level layouts, central A/C, dedicated interior laundry, and expansive upstairs and downstairs wrap-around porches overlooking lush tropical surroundings. The fully fenced grounds provide a private, shaded yard and the ultimate Old Town luxury: rare off-street parking. Live in one unit while generating passive income from the other, or hold as an income-producing multi-family portfolio piece in one of the nation's strongest rental markets. Situated on a quiet residential stretch just steps from Duval Street, Bahama Village dining, Fort Zachary Taylor State Park & Beach, and the Truman Waterfront. KEYWEST EVENTS : https://www.keywestchamber.org/visit.html

220 Angela St A & B, Unit A&B, Key West

1 Sharkys Golf Cart Repair & Rental, Key West

$349,000

SHARKY'S GOLF CART REPAIR & RENTAL -- TURNKEY KEY WEST BUSINESS OPPORTUNITY | $349,000 Rare opportunity to acquire an established Key West mobile golf cart and scooter repair, service and rental business serving Key West and Stock Island. Sharky's offers a flexible mobile business model with multiple revenue streams and the ability to operate without the overhead of a traditional storefront. The sale includes two service trucks equipped with tools and equipment, plus four new gas Club Car rental golf carts. Ideal for an owner-operator, entrepreneur, or an existing golf cart/powersports business looking to establish or expand a presence in the Florida Keys. Strong opportunity to build upon an established operation with a loyal and long standing customer base while enjoying the lifestyle and year-round demand of Key West. Offered at only $349,000 with a Net income to support. Financial information available to qualified buyers upon request and verification.

621498 MLS

SHARKY'S GOLF CART REPAIR & RENTAL -- TURNKEY KEY WEST BUSINESS OPPORTUNITY | $349,000 Rare opportunity to acquire an established Key West mobile golf cart and scooter repair, service and rental business serving Key West and Stock Island. Sharky's offers a flexible mobile business model with multiple revenue streams and the ability to operate without the overhead of a traditional storefront. The sale includes two service trucks equipped with tools and equipment, plus four new gas Club Car rental golf carts. Ideal for an owner-operator, entrepreneur, or an existing golf cart/powersports business looking to establish or expand a presence in the Florida Keys. Strong opportunity to build upon an established operation with a loyal and long standing customer base while enjoying the lifestyle and year-round demand of Key West. Offered at only $349,000 with a Net income to support. Financial information available to qualified buyers upon request and verification.

1 Sharkys Golf Cart Repair & Rental, Key West

$3,750,000

New construction, Elevated 3BD/3.5BA with heated pool and gated off-street parking on coveted Olivia Street. The Twins on Olivia is a Key West landmark reborn. The original structures, known locally as 'Olivia's Twins' and documented on the 1892 Sanborn maps, were condemned by the city and demolished. In their place, Kanga Construction has built an all-new 2,421 sq ft home on a 2,773 sq ft lot, designed with extensive guidance from Key West's HARC to honor the original twins in form and spirit. That history lives on in two separate staircases, a nod to the original pair of homes that also gives guests or family their own side of the house. All three bedrooms have ensuite baths and built-in closets, and dual-zone A/C with two whole-house dehumidifiers keeps every room comfortable year-round. French oak floors run throughout bright, open living spaces. The kitchen pairs Viking appliances, including a gas range and ice maker, with custom Hansel & Bringle cabinetry and quartz countertops. Impact-rated windows and doors, among them a custom mahogany front door with matching mahogany entry and lattice details, combine island craftsmanship with hurricane protection. Outside, ipe decking surrounds a heated pool with waterfall, set within private tropical landscaping. Off-street parking sits behind an electric gate. The home is offered fully turnkey, with a curated furniture package by local designer David Smith valued at over $150,000 plus plantation shutters throughout, all steps from Old Town's best restaurants, galleries and landmarks. Historic Key West character, built new.

3 Beds ⋅ 4 Baths ⋅ 621485 MLS

New construction, Elevated 3BD/3.5BA with heated pool and gated off-street parking on coveted Olivia Street. The Twins on Olivia is a Key West landmark reborn. The original structures, known locally as 'Olivia's Twins' and documented on the 1892 Sanborn maps, were condemned by the city and demolished. In their place, Kanga Construction has built an all-new 2,421 sq ft home on a 2,773 sq ft lot, designed with extensive guidance from Key West's HARC to honor the original twins in form and spirit. That history lives on in two separate staircases, a nod to the original pair of homes that also gives guests or family their own side of the house. All three bedrooms have ensuite baths and built-in closets, and dual-zone A/C with two whole-house dehumidifiers keeps every room comfortable year-round. French oak floors run throughout bright, open living spaces. The kitchen pairs Viking appliances, including a gas range and ice maker, with custom Hansel & Bringle cabinetry and quartz countertops. Impact-rated windows and doors, among them a custom mahogany front door with matching mahogany entry and lattice details, combine island craftsmanship with hurricane protection. Outside, ipe decking surrounds a heated pool with waterfall, set within private tropical landscaping. Off-street parking sits behind an electric gate. The home is offered fully turnkey, with a curated furniture package by local designer David Smith valued at over $150,000 plus plantation shutters throughout, all steps from Old Town's best restaurants, galleries and landmarks. Historic Key West character, built new.

1010 Olivia St, Key West

$1,195,000

Welcome to your dream home in the heart of Key West's MidTown! This beautifully updated 3-bedroom, 2-bathroom residence blends modern comfort with island charm. Step inside to a spacious, open-concept living area designed for both relaxing and entertaining. The true highlight is the private backyard oasis -- featuring a sparkling pool surrounded by fresh tropical landscaping, an expansive deck, and plenty of room for outdoor dining and lounging. Whether hosting guests or enjoying a quiet evening under the palms, this outdoor retreat feels like your own private paradise. Recent renovations provide peace of mind, including new impact windows and doors, Hardie board siding, and other thoughtful upgrades. Off-street parking adds everyday convenience. Perfectly located in the desirable MidTown neighborhood, this home keeps you close to shopping, dining, and all the best of Key West living. Don't miss this opportunity to own a beautifully updated slice of paradise in Key West -- schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ 621482 MLS

Welcome to your dream home in the heart of Key West's MidTown! This beautifully updated 3-bedroom, 2-bathroom residence blends modern comfort with island charm. Step inside to a spacious, open-concept living area designed for both relaxing and entertaining. The true highlight is the private backyard oasis -- featuring a sparkling pool surrounded by fresh tropical landscaping, an expansive deck, and plenty of room for outdoor dining and lounging. Whether hosting guests or enjoying a quiet evening under the palms, this outdoor retreat feels like your own private paradise. Recent renovations provide peace of mind, including new impact windows and doors, Hardie board siding, and other thoughtful upgrades. Off-street parking adds everyday convenience. Perfectly located in the desirable MidTown neighborhood, this home keeps you close to shopping, dining, and all the best of Key West living. Don't miss this opportunity to own a beautifully updated slice of paradise in Key West -- schedule your private showing today!

2911 Seidenberg Ave, Key West

$1,695,000

LOCATION! Situated on Garrison Bight, across the canal from the Key West Yacht Club, 5 Hilton Haven Dr. provides the best boating access on Key West. Tremendous opportunity for a buyer with a vision. The 4-bedroom, 4.5 bath, 2,027 sq. ft. home that is currently divided into 4 separate units in need of extensive repair. Or this home could be a good candidate for rebuilding as your single-family dream home with a pool, separate pool house, and 60' of dockage. Tucked away on one of Key West's few private drives, the home enjoys limited traffic and added privacy. Equipped with 2 electric meters and 9,058 sq. ft. lot, this property offers options and flexibility for bringing your vision to life.

4 Beds ⋅ 5 Baths ⋅ 621480 MLS

LOCATION! Situated on Garrison Bight, across the canal from the Key West Yacht Club, 5 Hilton Haven Dr. provides the best boating access on Key West. Tremendous opportunity for a buyer with a vision. The 4-bedroom, 4.5 bath, 2,027 sq. ft. home that is currently divided into 4 separate units in need of extensive repair. Or this home could be a good candidate for rebuilding as your single-family dream home with a pool, separate pool house, and 60' of dockage. Tucked away on one of Key West's few private drives, the home enjoys limited traffic and added privacy. Equipped with 2 electric meters and 9,058 sq. ft. lot, this property offers options and flexibility for bringing your vision to life.

5 Hilton Haven Dr, Key West

$1,169,000

Your Old Town Key West dream can start now -- with income built in. This exceptional 2-bedroom, 2.5-bath, townhouse-style condo offers a rare combination of Old Town lifestyle, flexible living space, and income-producing potential. Currently configured with a lock-off 1-bedroom apartment, the property offers an ideal opportunity for the future Key West homeowner: enjoy the larger 1 Bedroom, 1.5 Bath unit with private garden/patio as your own Key West retreat while the lock-off apartment provides substantial annual rental income. When the time comes to make Key West your full-time home, the property can be easily converted back to its original spacious 2-bedroom townhouse-style layout. A private gated entry opens to your own generous outdoor oasis, complete with a waterfall pond, large patio, and charming ''she-shed'' -- perfect for storage, an art studio, or entertaining. Inside, you'll find high ceilings, abundant natural light, generous storage, in-unit washer/dryers, and newer stainless-steel appliances. Just two blocks from Duval Street in the heart of Old Town's vibrant Bahama Village, you're surrounded by restaurants, galleries, shops, nightlife, and countless Key West attractions -- all within easy walking distance. Whether you're ready for a Key West home now or envision making the island your full-time home in the future, this is a rare opportunity to own your piece of Old Town, enjoy income along the way, and ultimately create the spacious Key West home you've been dreaming of. Some seller financing considered. Seller is a Florida Licensed Realtor. Photos 10-17 show Original Layout, 18=FloorPlan, 19-37 show Back Unit, 38-49 show Front Lock-Off Apt.

2 Beds ⋅ 3 Baths ⋅ 621479 MLS

Your Old Town Key West dream can start now -- with income built in. This exceptional 2-bedroom, 2.5-bath, townhouse-style condo offers a rare combination of Old Town lifestyle, flexible living space, and income-producing potential. Currently configured with a lock-off 1-bedroom apartment, the property offers an ideal opportunity for the future Key West homeowner: enjoy the larger 1 Bedroom, 1.5 Bath unit with private garden/patio as your own Key West retreat while the lock-off apartment provides substantial annual rental income. When the time comes to make Key West your full-time home, the property can be easily converted back to its original spacious 2-bedroom townhouse-style layout. A private gated entry opens to your own generous outdoor oasis, complete with a waterfall pond, large patio, and charming ''she-shed'' -- perfect for storage, an art studio, or entertaining. Inside, you'll find high ceilings, abundant natural light, generous storage, in-unit washer/dryers, and newer stainless-steel appliances. Just two blocks from Duval Street in the heart of Old Town's vibrant Bahama Village, you're surrounded by restaurants, galleries, shops, nightlife, and countless Key West attractions -- all within easy walking distance. Whether you're ready for a Key West home now or envision making the island your full-time home in the future, this is a rare opportunity to own your piece of Old Town, enjoy income along the way, and ultimately create the spacious Key West home you've been dreaming of. Some seller financing considered. Seller is a Florida Licensed Realtor. Photos 10-17 show Original Layout, 18=FloorPlan, 19-37 show Back Unit, 38-49 show Front Lock-Off Apt.

927 Thomas St Unit 1, Key West

$3,400,000

Discover the perfect blend of transient investment potential and coastal charm on Atlantic Boulevard. Just steps from the beach, this exceptional property offers a truly enchanting lifestyle with a distinctive boho-coastal aesthetic. The Atlantis House featuring five bedrooms and four bathrooms across three thoughtfully curated living spaces, this one-of-a-kind compound combines character, comfort, and style with an exciting opportunity for transient rental income. The primary residence is an exquisite 3-BR/2-BA monthly rental boasting a light-filled, open-concept floor plan for effortless island entertaining. You are welcomed into a mosaic-tiled foyer featuring whimsical swinging hammock chairs and a charming custom scooter coffee bar, flowing into spacious living areas adorned with timeless terrazzo floors. The heart of the home is a true gourmet kitchen, featuring a large island, pristine white quartz countertops, and separate Sub-Zero refrigerator and freezer. The main level offers two luxurious bedrooms opening to a beautifully landscaped fenced yard with a bistro patio. A spiral staircase leads upstairs to a third bedroom--a spectacular oasis with open water views. This level features dual sliding doors opening onto a magical, Trex rooftop terrace with a dining pergola and views of the Atlantic. It is the perfect perch to watch the sunrise with coffee in hand and return for the sunset. Around the corner are two detached, transient-licensed 1BR/1BA guest suites with dedicated parking. Both offer tasteful decor and private access to a backyard oasis with a large shared deck shaded by towering palms. Live the ultimate Key West lifestyle, a stone's throw from launching your kayak at the beach and a one-minute walk from the iconic White Street Pier. The Atlantis House conveys with its own house-made Atlantis Key Lime Pie recipe, passed from the former owner to the new owner, a tradition carried for more than 30 years. A one-of-a-kind treasure!

5 Beds ⋅ 4 Baths ⋅ 621477 MLS

Discover the perfect blend of transient investment potential and coastal charm on Atlantic Boulevard. Just steps from the beach, this exceptional property offers a truly enchanting lifestyle with a distinctive boho-coastal aesthetic. The Atlantis House featuring five bedrooms and four bathrooms across three thoughtfully curated living spaces, this one-of-a-kind compound combines character, comfort, and style with an exciting opportunity for transient rental income. The primary residence is an exquisite 3-BR/2-BA monthly rental boasting a light-filled, open-concept floor plan for effortless island entertaining. You are welcomed into a mosaic-tiled foyer featuring whimsical swinging hammock chairs and a charming custom scooter coffee bar, flowing into spacious living areas adorned with timeless terrazzo floors. The heart of the home is a true gourmet kitchen, featuring a large island, pristine white quartz countertops, and separate Sub-Zero refrigerator and freezer. The main level offers two luxurious bedrooms opening to a beautifully landscaped fenced yard with a bistro patio. A spiral staircase leads upstairs to a third bedroom--a spectacular oasis with open water views. This level features dual sliding doors opening onto a magical, Trex rooftop terrace with a dining pergola and views of the Atlantic. It is the perfect perch to watch the sunrise with coffee in hand and return for the sunset. Around the corner are two detached, transient-licensed 1BR/1BA guest suites with dedicated parking. Both offer tasteful decor and private access to a backyard oasis with a large shared deck shaded by towering palms. Live the ultimate Key West lifestyle, a stone's throw from launching your kayak at the beach and a one-minute walk from the iconic White Street Pier. The Atlantis House conveys with its own house-made Atlantis Key Lime Pie recipe, passed from the former owner to the new owner, a tradition carried for more than 30 years. A one-of-a-kind treasure!

1401 Atlantic Blvd, Key West

$3,400,000

Discover the perfect blend of transient investment potential and coastal charm on Atlantic Boulevard. Just steps from the beach, this exceptional property offers a truly enchanting lifestyle with a distinctive boho-coastal aesthetic. The Atlantis House featuring five bedrooms and four bathrooms across three thoughtfully curated living spaces, this one-of-a-kind compound combines character, comfort, and style with an exciting opportunity for transient rental income. The primary residence is an exquisite 3-BR/2-BA monthly rental boasting a light-filled, open-concept floor plan for effortless island entertaining. You are welcomed into a mosaic-tiled foyer featuring whimsical swinging hammock chairs and a charming custom scooter coffee bar, flowing into spacious living areas adorned with timeless terrazzo floors. The heart of the home is a true gourmet kitchen, featuring a large island, pristine white quartz countertops, and separate Sub-Zero refrigerator and freezer. The main level offers two luxurious bedrooms opening to a beautifully landscaped fenced yard with a bistro patio. A spiral staircase leads upstairs to a third bedroom--a spectacular oasis with open water views. This level features dual sliding doors opening onto a magical, Trex rooftop terrace with a dining pergola and views of the Atlantic. It is the perfect perch to watch the sunrise with coffee in hand and return for the sunset. Around the corner are two detached, transient-licensed 1BR/1BA guest suites with dedicated parking. Both offer tasteful decor and private access to a backyard oasis with a large shared deck shaded by towering palms. Live the ultimate Key West lifestyle, a stone's throw from launching your kayak at the beach and a one-minute walk from the iconic White Street Pier. The Atlantis House conveys with its own house-made Atlantis Key Lime Pie recipe, passed from the former owner to the new owner, a tradition carried for more than 30 years. A one-of-a-kind treasure!

5 Beds ⋅ 4 Baths ⋅ 621476 MLS

Discover the perfect blend of transient investment potential and coastal charm on Atlantic Boulevard. Just steps from the beach, this exceptional property offers a truly enchanting lifestyle with a distinctive boho-coastal aesthetic. The Atlantis House featuring five bedrooms and four bathrooms across three thoughtfully curated living spaces, this one-of-a-kind compound combines character, comfort, and style with an exciting opportunity for transient rental income. The primary residence is an exquisite 3-BR/2-BA monthly rental boasting a light-filled, open-concept floor plan for effortless island entertaining. You are welcomed into a mosaic-tiled foyer featuring whimsical swinging hammock chairs and a charming custom scooter coffee bar, flowing into spacious living areas adorned with timeless terrazzo floors. The heart of the home is a true gourmet kitchen, featuring a large island, pristine white quartz countertops, and separate Sub-Zero refrigerator and freezer. The main level offers two luxurious bedrooms opening to a beautifully landscaped fenced yard with a bistro patio. A spiral staircase leads upstairs to a third bedroom--a spectacular oasis with open water views. This level features dual sliding doors opening onto a magical, Trex rooftop terrace with a dining pergola and views of the Atlantic. It is the perfect perch to watch the sunrise with coffee in hand and return for the sunset. Around the corner are two detached, transient-licensed 1BR/1BA guest suites with dedicated parking. Both offer tasteful decor and private access to a backyard oasis with a large shared deck shaded by towering palms. Live the ultimate Key West lifestyle, a stone's throw from launching your kayak at the beach and a one-minute walk from the iconic White Street Pier. The Atlantis House conveys with its own house-made Atlantis Key Lime Pie recipe, passed from the former owner to the new owner, a tradition carried for more than 30 years. A one-of-a-kind treasure!

1401 Atlantic Blvd, Key West

1901 S Roosevelt Blvd Unit 208E, Key West

$1,349,000

Direct ocean views await at this rarely available 3-bedroom, 2-bath condominium in Key West's gated La Brisa community, directly across from Smathers Beach. Whether you're seeking a full-time residence or a seasonal escape, Unit 208E offers bright living spaces, an updated kitchen, and resort-style amenities. The open floor plan connects the kitchen, dining, and living areas, creating an inviting space for everyday living and entertaining. Sliding glass doors open to a private balcony overlooking the ocean--an ideal setting for morning coffee and enjoying the sea breeze. The updated kitchen features modern cabinetry and ample counter space. The primary suite features ocean views through a large picture window, direct balcony access, generous closet space, and an en-suite bath. Two additional bedrooms offer comfortable accommodations for family and guests or space for a home office. La Brisa's amenities include a heated pool, hot tub, tennis and pickleball court, clubhouse, BBQ area, EV charging stations, and gated entry. Enjoy convenient access to the beach, bike paths, airport, and Key West's dining and attractions. Seller is a family member of the listing agent.

3 Beds ⋅ 2 Baths ⋅ 621474 MLS

Direct ocean views await at this rarely available 3-bedroom, 2-bath condominium in Key West's gated La Brisa community, directly across from Smathers Beach. Whether you're seeking a full-time residence or a seasonal escape, Unit 208E offers bright living spaces, an updated kitchen, and resort-style amenities. The open floor plan connects the kitchen, dining, and living areas, creating an inviting space for everyday living and entertaining. Sliding glass doors open to a private balcony overlooking the ocean--an ideal setting for morning coffee and enjoying the sea breeze. The updated kitchen features modern cabinetry and ample counter space. The primary suite features ocean views through a large picture window, direct balcony access, generous closet space, and an en-suite bath. Two additional bedrooms offer comfortable accommodations for family and guests or space for a home office. La Brisa's amenities include a heated pool, hot tub, tennis and pickleball court, clubhouse, BBQ area, EV charging stations, and gated entry. Enjoy convenient access to the beach, bike paths, airport, and Key West's dining and attractions. Seller is a family member of the listing agent.

1901 S Roosevelt Blvd Unit 208E, Key West

$1,725,000

Tucked behind the gates of Seaside Residences, this exceptional 4-floor Townhome delivers the kind of Atlantic views most people only dream about. With four generous bedrooms and four beautifully appointed bathrooms, this home blends comfort with effortless style. A private four-stop elevator glides you between floors, while six separate balconies give you endless options for your morning coffee or evening cocktail: some framed by open ocean, others overlooking lush, tranquil surroundings. The chef's kitchen doesn't disappoint: high-end appliances, a trash compactor, in-unit trash chutes, and a pantry large enough to keep everything organized. First-floor laundry adds everyday convenience, and storage is never an issue thanks to closets tucked throughout the home. Step outside to your own private, garden lined patio and outdoor shower makes rinsing off after beach days effortless. Inside, granite counters and hardwood floors run throughout, and the attached garage comes with an automatic opener. Climb the indoor ladder up to your rooftop deck for unbeatable stargazing or sunbathing with a bird's eye view of the coastline. Residents also enjoy access to the community's shared pool, perfect for a relaxed swim without the upkeep of a private one. Fully furnished with high end furnishings throughout, this Townhome is a rare find in one of the area's most prestigious gated communities where luxury truly meets the ocean.

4 Beds ⋅ 4 Baths ⋅ 621472 MLS

Tucked behind the gates of Seaside Residences, this exceptional 4-floor Townhome delivers the kind of Atlantic views most people only dream about. With four generous bedrooms and four beautifully appointed bathrooms, this home blends comfort with effortless style. A private four-stop elevator glides you between floors, while six separate balconies give you endless options for your morning coffee or evening cocktail: some framed by open ocean, others overlooking lush, tranquil surroundings. The chef's kitchen doesn't disappoint: high-end appliances, a trash compactor, in-unit trash chutes, and a pantry large enough to keep everything organized. First-floor laundry adds everyday convenience, and storage is never an issue thanks to closets tucked throughout the home. Step outside to your own private, garden lined patio and outdoor shower makes rinsing off after beach days effortless. Inside, granite counters and hardwood floors run throughout, and the attached garage comes with an automatic opener. Climb the indoor ladder up to your rooftop deck for unbeatable stargazing or sunbathing with a bird's eye view of the coastline. Residents also enjoy access to the community's shared pool, perfect for a relaxed swim without the upkeep of a private one. Fully furnished with high end furnishings throughout, this Townhome is a rare find in one of the area's most prestigious gated communities where luxury truly meets the ocean.

37 Seaside South Ct, Key West

$799,000

Welcome to 2506 Seidenberg Avenue, a spacious 3-bedroom, 3-bath home offering 1,922 square feet of living space in the heart of Midtown Key West. Framed by tropical landscaping and a classic white picket fence, this home offers plenty of space and a flexible layout for comfortable island living. The main living area flows into a large eat-in kitchen featuring abundant cabinetry, stainless steel appliances, generous counter space, and plenty of room for dining and entertaining. Three bedrooms and three full baths provide ample accommodations, while additional living space at the rear of the property offers added flexibility for guests, a home office, den, or private retreat. A garage provides valuable parking and storage. Centrally located just minutes from Old Town, beaches, shopping, dining, and all that Key West has to offer. With nearly 2,000 square feet, versatile additional living space, a garage, and a convenient Midtown location, 2506 Seidenberg Avenue presents a unique opportunity to make a Key West home your own. Owner financing may be available.

3 Beds ⋅ 3 Baths ⋅ 621467 MLS

Welcome to 2506 Seidenberg Avenue, a spacious 3-bedroom, 3-bath home offering 1,922 square feet of living space in the heart of Midtown Key West. Framed by tropical landscaping and a classic white picket fence, this home offers plenty of space and a flexible layout for comfortable island living. The main living area flows into a large eat-in kitchen featuring abundant cabinetry, stainless steel appliances, generous counter space, and plenty of room for dining and entertaining. Three bedrooms and three full baths provide ample accommodations, while additional living space at the rear of the property offers added flexibility for guests, a home office, den, or private retreat. A garage provides valuable parking and storage. Centrally located just minutes from Old Town, beaches, shopping, dining, and all that Key West has to offer. With nearly 2,000 square feet, versatile additional living space, a garage, and a convenient Midtown location, 2506 Seidenberg Avenue presents a unique opportunity to make a Key West home your own. Owner financing may be available.

2506 Seidenberg Ave, Key West

$6,895,000

The Autograph House is a newly built, architect-designed luxury property in the heart of Old Town Key West, ideally positioned just one block from Duval Street and the island's most celebrated attractions. Blending refined modern design with the relaxed elegance of Key West, this exceptional property offers a rare combination of sophistication, privacy and walkable convenience. The home encompasses a stunning two-story Main Residence with four private bedroom suites, each featuring an en-suite bath with custom millwork, along with a beautifully appointed two-bedroom, two-bath Guest Cottage. Together, the residences create an exceptional six-bedroom, six-bathroom estate ideal for multi-generational living, extended stays, or entertaining. The Main Residence features an expansive open-concept living, dining, and chef's kitchen with premium Miele appliances, Fisher & Paykel column refrigeration, custom cabinetry, and a generous island. Floor-to-ceiling impact-rated sliding glass doors open seamlessly to a covered outdoor living and entertaining area, complete with lounge seating, a fully equipped outdoor kitchen, grill, beverage refrigerator, and dining space. Lush tropical landscaping surrounds a private heated pool and separate hot tub. The Main Residence pool features a waterfall and built-in bench seating, while the Guest Cottage offers its own private spa hot tub. An outdoor shower and secluded garden spaces further enhance the resort-like setting. Throughout the property, custom finishes, beautiful furnishings, Sonos audio, and full-size laundry facilities reflect an exceptional level of comfort and attention to detail. Perfectly situated in Old Town's X-Flood Zone, this home places Duval Street, Mallory Square, world-class dining, galleries, shopping, beaches, and iconic Key West landmarks just moments away. A rare opportunity to own a turnkey luxury compound in one of Key West's most coveted locations. Call today for a showing!

6 Beds ⋅ 7 Baths ⋅ 621466 MLS

The Autograph House is a newly built, architect-designed luxury property in the heart of Old Town Key West, ideally positioned just one block from Duval Street and the island's most celebrated attractions. Blending refined modern design with the relaxed elegance of Key West, this exceptional property offers a rare combination of sophistication, privacy and walkable convenience. The home encompasses a stunning two-story Main Residence with four private bedroom suites, each featuring an en-suite bath with custom millwork, along with a beautifully appointed two-bedroom, two-bath Guest Cottage. Together, the residences create an exceptional six-bedroom, six-bathroom estate ideal for multi-generational living, extended stays, or entertaining. The Main Residence features an expansive open-concept living, dining, and chef's kitchen with premium Miele appliances, Fisher & Paykel column refrigeration, custom cabinetry, and a generous island. Floor-to-ceiling impact-rated sliding glass doors open seamlessly to a covered outdoor living and entertaining area, complete with lounge seating, a fully equipped outdoor kitchen, grill, beverage refrigerator, and dining space. Lush tropical landscaping surrounds a private heated pool and separate hot tub. The Main Residence pool features a waterfall and built-in bench seating, while the Guest Cottage offers its own private spa hot tub. An outdoor shower and secluded garden spaces further enhance the resort-like setting. Throughout the property, custom finishes, beautiful furnishings, Sonos audio, and full-size laundry facilities reflect an exceptional level of comfort and attention to detail. Perfectly situated in Old Town's X-Flood Zone, this home places Duval Street, Mallory Square, world-class dining, galleries, shopping, beaches, and iconic Key West landmarks just moments away. A rare opportunity to own a turnkey luxury compound in one of Key West's most coveted locations. Call today for a showing!

317 Whitehead St, Key West

$4,300,000

There is a certain rhythm to life in Key West. Mornings begin outside, friends have a way of staying longer than planned, and some of the best evenings never make it past the backyard. 1614 Washington Street was designed for exactly that kind of life. Natural light, high ceilings, and an easy connection to the outdoors give the home an immediate sense of openness. The main living spaces flow naturally toward the pool and tropical garden, creating a setting that works just as well for a quiet morning at home as it does for dinner with friends that stretches late into the evening. The heated and chilled pool features two distinct levels--a shallow splash deck and a deeper swimming area--connected by cascading water features and surrounded by mature tropical landscaping that feels remarkably private. The floor plan understands that guests are part of island life, but privacy still matters. The first-floor primary suite creates a comfortable retreat for the owners, while upstairs, three en-suite bedrooms surround their own den and lounge. Family and friends can settle in, unpack, and have a space of their own rather than simply occupying yours. Behind that relaxed lifestyle is a house designed to make living here easier. Award-winning local architect Matthew Stratton brought together solid masonry construction, impact-rated windows and doors, solar power with Tesla battery storage, an EV charger, custom cabinetry, quartz surfaces, and thoughtful systems chosen for the realities of coastal living. The technology is there when you need it and nearly invisible when you don't. Morning walks, bike rides, the beach, neighborhood restaurants, galleries, and everything that makes Key West unlike anywhere else are simply part of the day. 1614 Washington invites you to open the doors, gather the people you love, jump in the pool, stay for dinner, and make yourself at home. Because ultimately, the best luxury isn't about having more. It's having a home that lets you live well.

4 Beds ⋅ 5 Baths ⋅ 621463 MLS

There is a certain rhythm to life in Key West. Mornings begin outside, friends have a way of staying longer than planned, and some of the best evenings never make it past the backyard. 1614 Washington Street was designed for exactly that kind of life. Natural light, high ceilings, and an easy connection to the outdoors give the home an immediate sense of openness. The main living spaces flow naturally toward the pool and tropical garden, creating a setting that works just as well for a quiet morning at home as it does for dinner with friends that stretches late into the evening. The heated and chilled pool features two distinct levels--a shallow splash deck and a deeper swimming area--connected by cascading water features and surrounded by mature tropical landscaping that feels remarkably private. The floor plan understands that guests are part of island life, but privacy still matters. The first-floor primary suite creates a comfortable retreat for the owners, while upstairs, three en-suite bedrooms surround their own den and lounge. Family and friends can settle in, unpack, and have a space of their own rather than simply occupying yours. Behind that relaxed lifestyle is a house designed to make living here easier. Award-winning local architect Matthew Stratton brought together solid masonry construction, impact-rated windows and doors, solar power with Tesla battery storage, an EV charger, custom cabinetry, quartz surfaces, and thoughtful systems chosen for the realities of coastal living. The technology is there when you need it and nearly invisible when you don't. Morning walks, bike rides, the beach, neighborhood restaurants, galleries, and everything that makes Key West unlike anywhere else are simply part of the day. 1614 Washington invites you to open the doors, gather the people you love, jump in the pool, stay for dinner, and make yourself at home. Because ultimately, the best luxury isn't about having more. It's having a home that lets you live well.

1614 Washington St, Key West

$2,475,000

Discover the charm of what was once a carriage house and now a single-level home nestled in the highly desirable Meadows neighborhood of Old Town Key West. This inviting 3-bedroom, 2-bath residence blends historic character with modern updates, offering the quintessential island lifestyle. Effortless indoor-outdoor living defines this home, which features an open, airy feel that flows seamlessly to a private backyard oasis. The renovated kitchen features quartz countertops, modern finishes perfect for entertaining or everyday living. A versatile bonus loft provides the ideal space for a home office. Step outside to your own tropical retreat, complete with a sparkling pool surrounded by a spacious brick patio, cabana bar, fabulous outdoor shower and mature landscaping that creates privacy and a lush island ambiance. Topped off with off-street parking, whole house generator, x flood zone and close proximity to everything that makes Key West living so special, while still providing a peaceful neighborhood setting. This is truly a gem waiting to become your tropical island home!

3 Beds ⋅ 2 Baths ⋅ 621462 MLS

Discover the charm of what was once a carriage house and now a single-level home nestled in the highly desirable Meadows neighborhood of Old Town Key West. This inviting 3-bedroom, 2-bath residence blends historic character with modern updates, offering the quintessential island lifestyle. Effortless indoor-outdoor living defines this home, which features an open, airy feel that flows seamlessly to a private backyard oasis. The renovated kitchen features quartz countertops, modern finishes perfect for entertaining or everyday living. A versatile bonus loft provides the ideal space for a home office. Step outside to your own tropical retreat, complete with a sparkling pool surrounded by a spacious brick patio, cabana bar, fabulous outdoor shower and mature landscaping that creates privacy and a lush island ambiance. Topped off with off-street parking, whole house generator, x flood zone and close proximity to everything that makes Key West living so special, while still providing a peaceful neighborhood setting. This is truly a gem waiting to become your tropical island home!

1212 Olivia St, Key West

$2,195,000

Completed in 2025, this brand-new, elevated two-story home rises above the surrounding homes and is built above flood level. Excellent location close to the beach. Category 5 hurricane-rated construction, impact windows and doors, and Hardie board siding combine coastal style with storm protection. The home offers 3 bedrooms and 3 bathrooms, plus an office currently set up with bunk beds as a fourth sleeping space. Separate laundry room. The backyard is a gorgeous tropical retreat. A large heated pool and spa are surrounded by a gorgeous stone deck, lush landscaping and dramatic evening lighting. A huge poolside Tiki hut creates a spectacular setting for shaded dining, lounging and entertaining, while a putting green adds to the fun. Generous gathering areas and a completely fenced yard make this outdoor oasis perfect for sunny afternoons and unforgettable evenings beneath the palms. Inside, bright, open living and dining spaces flow into a beautiful kitchen with white cabinetry, stainless steel appliances, a blue tile backsplash and a generous island with seating. Balconies extend the living space outdoors. Beneath the home, a large covered area offers room to watch sports, relax and entertain, or serve as a carport. A permitted downstairs enclosure provides valuable storage and pool cabana. New construction, an elevated setting and an exceptional backyard come together in one remarkable property. Don't miss your opportunity to make this tropical escape your own!

3 Beds ⋅ 2 Baths ⋅ 621461 MLS

Completed in 2025, this brand-new, elevated two-story home rises above the surrounding homes and is built above flood level. Excellent location close to the beach. Category 5 hurricane-rated construction, impact windows and doors, and Hardie board siding combine coastal style with storm protection. The home offers 3 bedrooms and 3 bathrooms, plus an office currently set up with bunk beds as a fourth sleeping space. Separate laundry room. The backyard is a gorgeous tropical retreat. A large heated pool and spa are surrounded by a gorgeous stone deck, lush landscaping and dramatic evening lighting. A huge poolside Tiki hut creates a spectacular setting for shaded dining, lounging and entertaining, while a putting green adds to the fun. Generous gathering areas and a completely fenced yard make this outdoor oasis perfect for sunny afternoons and unforgettable evenings beneath the palms. Inside, bright, open living and dining spaces flow into a beautiful kitchen with white cabinetry, stainless steel appliances, a blue tile backsplash and a generous island with seating. Balconies extend the living space outdoors. Beneath the home, a large covered area offers room to watch sports, relax and entertain, or serve as a carport. A permitted downstairs enclosure provides valuable storage and pool cabana. New construction, an elevated setting and an exceptional backyard come together in one remarkable property. Don't miss your opportunity to make this tropical escape your own!

1716 Laird St, Key West

$199,000

Sunset Marina offers a range of amenities and attractions that make it a desirable destination for live aboard boaters and visitors alike. Starfish # 6 is a 30 ft boat slip that accommodates a max of 35 ft overall boat length. The marina features a variety of boat slips that can accommodate different sizes of vessels, providing easy access to the water. A convenient fuel dock is available for quick refueling, ensuring that boaters can get back on the water without delay. Clean and well-maintained restrooms and shower facilities are provided for guests, enhancing comfort during extended stays. On-site laundry facilities offer the convenience of washing clothes while enjoying time at the marina. Sunset Marina is known for its stunning views, particularly during sunset, making it a great spot for relaxation and photography. The surrounding waters are perfect for a variety of activities, including fishing, kayaking, and paddleboarding. Nearby restaurants and bars provide a range of dining experiences, from casual bites to fine dining, often with waterfront views. Located near local attractions such as parks, beaches, and shops, visitors can easily explore the surrounding area. The combination of these amenities and the beautiful setting makes Sunset Marina a popular choice for boaters seeking both convenience and enjoyment.

621459 MLS

Sunset Marina offers a range of amenities and attractions that make it a desirable destination for live aboard boaters and visitors alike. Starfish # 6 is a 30 ft boat slip that accommodates a max of 35 ft overall boat length. The marina features a variety of boat slips that can accommodate different sizes of vessels, providing easy access to the water. A convenient fuel dock is available for quick refueling, ensuring that boaters can get back on the water without delay. Clean and well-maintained restrooms and shower facilities are provided for guests, enhancing comfort during extended stays. On-site laundry facilities offer the convenience of washing clothes while enjoying time at the marina. Sunset Marina is known for its stunning views, particularly during sunset, making it a great spot for relaxation and photography. The surrounding waters are perfect for a variety of activities, including fishing, kayaking, and paddleboarding. Nearby restaurants and bars provide a range of dining experiences, from casual bites to fine dining, often with waterfront views. Located near local attractions such as parks, beaches, and shops, visitors can easily explore the surrounding area. The combination of these amenities and the beautiful setting makes Sunset Marina a popular choice for boaters seeking both convenience and enjoyment.

5555 College Rd Unit 6, Key West

$6,450,000

A rare opportunity in the heart of Old Town Key West's coveted Seaport neighborhood, this exceptional multi-residence property combines the charm and architectural character of historic Key West with the comfort, quality and convenience of newly constructed living. Thoughtfully designed to retain the home's traditional aesthetic, the property offers remarkable flexibility as a private compound, multigenerational residence or sophisticated investment property, with beautifully finished interiors, resort-style outdoor spaces and exceptional parking for the neighborhood. The main residence is a legal triplex, with each home offering its own privacy and character and 3 off street parking spaces. At the front of the property, a charming 1-bedroom, 1-bath residence occupies the first floor and opens to a generous covered porch and private yard. A separate side entrance leads to a distinctive three-story, 2-bedroom, 2.5-bath residence with its own side porch and upper levels overlooking the front of the property. Occupying the rear portion of the main house is the largest residence, a spacious 3-bedroom, 3.5-bath home arranged entirely on the main living level. Beautifully finished interiors open to a lush tropical retreat with a private pool, fountains, expansive patios, outdoor dining and multiple lounging areas. An unfinished basement offers exceptional potential for a wine cellar, tasting room or collection space. A landscaped walkway leads to a separate 1-bedroom, 1-bath cottage fronting Peacon Lane, with a private rear deck, outdoor dining area and two-car off-street parking. Importantly, the Peacon Lane residence sits on its own separate legal parcel, providing the rare flexibility for it to be owned or sold independently from the main property should a future owner ever choose to do so. Just beyond the gates, the waterfront, restaurants, galleries, shops and historic sites are all within an easy walk in one of Old Town Key West's most desirable neighborhoods.

7 Beds ⋅ 9 Baths ⋅ 621458 MLS

A rare opportunity in the heart of Old Town Key West's coveted Seaport neighborhood, this exceptional multi-residence property combines the charm and architectural character of historic Key West with the comfort, quality and convenience of newly constructed living. Thoughtfully designed to retain the home's traditional aesthetic, the property offers remarkable flexibility as a private compound, multigenerational residence or sophisticated investment property, with beautifully finished interiors, resort-style outdoor spaces and exceptional parking for the neighborhood. The main residence is a legal triplex, with each home offering its own privacy and character and 3 off street parking spaces. At the front of the property, a charming 1-bedroom, 1-bath residence occupies the first floor and opens to a generous covered porch and private yard. A separate side entrance leads to a distinctive three-story, 2-bedroom, 2.5-bath residence with its own side porch and upper levels overlooking the front of the property. Occupying the rear portion of the main house is the largest residence, a spacious 3-bedroom, 3.5-bath home arranged entirely on the main living level. Beautifully finished interiors open to a lush tropical retreat with a private pool, fountains, expansive patios, outdoor dining and multiple lounging areas. An unfinished basement offers exceptional potential for a wine cellar, tasting room or collection space. A landscaped walkway leads to a separate 1-bedroom, 1-bath cottage fronting Peacon Lane, with a private rear deck, outdoor dining area and two-car off-street parking. Importantly, the Peacon Lane residence sits on its own separate legal parcel, providing the rare flexibility for it to be owned or sold independently from the main property should a future owner ever choose to do so. Just beyond the gates, the waterfront, restaurants, galleries, shops and historic sites are all within an easy walk in one of Old Town Key West's most desirable neighborhoods.

723 Eaton St, Key West

5555 College Rd Unit Sailfish 2, Key West

$295,000

Best deeded wet slip location in this Key West marina for a 55' LOA boat! Stage your boat along the main dock, close to the clubhouse, pool, hot tub and parking. This property is a gated secure community and just minutes from the golf course and downtown activities. Liveaboard is limited to 2 nights per week, 7 nights per month. Local marina amenities include access to a ship's store and fuel dock. Located on the leeway side of the island with Bellingham floating docks, the slip has easy ingress / egress to the Gulf and Atlantic Ocean.

621452 MLS

Best deeded wet slip location in this Key West marina for a 55' LOA boat! Stage your boat along the main dock, close to the clubhouse, pool, hot tub and parking. This property is a gated secure community and just minutes from the golf course and downtown activities. Liveaboard is limited to 2 nights per week, 7 nights per month. Local marina amenities include access to a ship's store and fuel dock. Located on the leeway side of the island with Bellingham floating docks, the slip has easy ingress / egress to the Gulf and Atlantic Ocean.

5555 College Rd Unit Sailfish 2, Key West