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Located on the northside of Old Town only two blocks from the historic Key West Port, NYAH is walking distance from the main strip of bars and restaurants on Duval and proximate to historical landmarks such as the Southernmost Point, Ernest Hemingway Home, Key West Butterfly Conservatory, and Mallory Square. The Property is designed for hosting group travelers offering both private and shared guestrooms. Private Rooms can accommodate groups of up to six people and each guest is provided their own bed, locker, and set of towels. Guestroom amenities include en-suite bathrooms, private lockers, and personal charging docks. Home to three outdoor pools, NYAH is in possession of a bar license and serves drinks from the front desk. NYAH also features an office space which can be converted into a 3-bedroom transient unit. As the Property holds 36 transient licenses, no additional ROGO is needed.

611315 MLS

Located on the northside of Old Town only two blocks from the historic Key West Port, NYAH is walking distance from the main strip of bars and restaurants on Duval and proximate to historical landmarks such as the Southernmost Point, Ernest Hemingway Home, Key West Butterfly Conservatory, and Mallory Square. The Property is designed for hosting group travelers offering both private and shared guestrooms. Private Rooms can accommodate groups of up to six people and each guest is provided their own bed, locker, and set of towels. Guestroom amenities include en-suite bathrooms, private lockers, and personal charging docks. Home to three outdoor pools, NYAH is in possession of a bar license and serves drinks from the front desk. NYAH also features an office space which can be converted into a 3-bedroom transient unit. As the Property holds 36 transient licenses, no additional ROGO is needed.

823 Fleming St, Key West

$13,500,000

Statistical Purposes Only

620099 MLS

Statistical Purposes Only

313 Duval St, Key West

$9,500,000

Heron House Court presents a unique chance to own a boutique guesthouse in the heart of Old Town Key West. This historic gem has been well maintained through the years & offers 15 deluxe rooms (14 licensed transient rentals).The relaxed atmosphere, with its private porches and multiple decked lounging areas throughout creates a wonderful ambiance. Steeped in history, Heron House Court circa 1900, was originally built to house the workers of Flagler's famous overseas Railway & is listed on the national register of historic places. Perfectly situated just a short stroll from Duval Street's world-class dining, shopping, and nightlife, as well as the Historic Seaport boardwalk, this island retreat attracts a steady stream of visitors year-round. The island-style setting, lush tropical gardens, expansive covered porches, and serene heated pool, create an unforgettable Key West experience. Sold fully furnished and turnkey, this well-established business includes all equipment, booking software, and a proven rental history, ensuring a smooth ownership transition. Heron House Court is a rare and wonderful opportunity to own in one of the most sought-after locations in Key West with unlimited potential.

15 Beds ⋅ 18 Baths ⋅ 614404 MLS

Heron House Court presents a unique chance to own a boutique guesthouse in the heart of Old Town Key West. This historic gem has been well maintained through the years & offers 15 deluxe rooms (14 licensed transient rentals).The relaxed atmosphere, with its private porches and multiple decked lounging areas throughout creates a wonderful ambiance. Steeped in history, Heron House Court circa 1900, was originally built to house the workers of Flagler's famous overseas Railway & is listed on the national register of historic places. Perfectly situated just a short stroll from Duval Street's world-class dining, shopping, and nightlife, as well as the Historic Seaport boardwalk, this island retreat attracts a steady stream of visitors year-round. The island-style setting, lush tropical gardens, expansive covered porches, and serene heated pool, create an unforgettable Key West experience. Sold fully furnished and turnkey, this well-established business includes all equipment, booking software, and a proven rental history, ensuring a smooth ownership transition. Heron House Court is a rare and wonderful opportunity to own in one of the most sought-after locations in Key West with unlimited potential.

412 Frances St, Key West

$7,500,000

Brand new waterfront home on Sunset Key. For statistical purposes only.

4 Beds ⋅ 5 Baths ⋅ 619683 MLS

Brand new waterfront home on Sunset Key. For statistical purposes only.

2 Sunset, Key West

$7,250,000

Located in the heart of Old Town, 616 Eaton Street tells a story that spans more than a century. Built in 1911 and thoughtfully brought into the present day, with additions & renovations, this property reflects the enduring character of Key West while offering the comforts and conveniences of modern living. This 5BD, 5 full BA, and 2 half BA estate spans over 4,000sf and sits on an expansive 12,478sf lot. Set back from the street, it offers a level of privacy that is rare for such a central location. The main residence is designed for both everyday living & entertaining and has been furnished with new furniture & finishings adding a refined & move in ready touch. The fabulous kitchen, outfitted with top of the line finishes, opens through huge sliding glass windows to an outdoor bar & entertaining pavilion creating a seamless indoor & outdoor experience. Upstairs, the primary suite offers a quiet escape with its own office, laundry, and a generous covered porch. Throughout the home, reclaimed hardwood floors from the Biltmore, tall ceilings, and natural light highlight the balance between historic charm & modern upgrades. The outdoor space serves as the heart of the property, anchored by a heated & chilled saltwater pool with a tranquil water feature. Two detached guest houses provide a total of 3BD & 3BA, complemented by an additional cottage that can function as a 4th bedroom & bath or a private entertaining retreat. The versatility of this home is truly exceptional, ideal for hosting guests, extended stays, or creating secluded personal spaces. Additional features include a 1,500sf climate controlled attic for storage, off-street parking for up to 7 vehicles, a carport, and a golf cart garage. Positioned in the desirable X flood zone and just 2 blocks from Duval St. and the Historic Seaport, this property represents a rare opportunity to own a significant piece of Key West history, thoughtfully updated for modern living.

5 Beds ⋅ 7 Baths ⋅ 619282 MLS

Located in the heart of Old Town, 616 Eaton Street tells a story that spans more than a century. Built in 1911 and thoughtfully brought into the present day, with additions & renovations, this property reflects the enduring character of Key West while offering the comforts and conveniences of modern living. This 5BD, 5 full BA, and 2 half BA estate spans over 4,000sf and sits on an expansive 12,478sf lot. Set back from the street, it offers a level of privacy that is rare for such a central location. The main residence is designed for both everyday living & entertaining and has been furnished with new furniture & finishings adding a refined & move in ready touch. The fabulous kitchen, outfitted with top of the line finishes, opens through huge sliding glass windows to an outdoor bar & entertaining pavilion creating a seamless indoor & outdoor experience. Upstairs, the primary suite offers a quiet escape with its own office, laundry, and a generous covered porch. Throughout the home, reclaimed hardwood floors from the Biltmore, tall ceilings, and natural light highlight the balance between historic charm & modern upgrades. The outdoor space serves as the heart of the property, anchored by a heated & chilled saltwater pool with a tranquil water feature. Two detached guest houses provide a total of 3BD & 3BA, complemented by an additional cottage that can function as a 4th bedroom & bath or a private entertaining retreat. The versatility of this home is truly exceptional, ideal for hosting guests, extended stays, or creating secluded personal spaces. Additional features include a 1,500sf climate controlled attic for storage, off-street parking for up to 7 vehicles, a carport, and a golf cart garage. Positioned in the desirable X flood zone and just 2 blocks from Duval St. and the Historic Seaport, this property represents a rare opportunity to own a significant piece of Key West history, thoughtfully updated for modern living.

616 Eaton St, Key West

$7,200,000

A rare opportunity to own the only active listing on the most prestigious shoreline of Sunset Key — Crescent Beach. This immaculate 4-bedroom, 3.5-bath home offers direct beach access from your backyard and showcases vibrant, dramatic island flair throughout. Upon entry, you're welcomed by soaring 25-ft ceilings, a dramatic great room with a custom chandelier, and an open layout flowing into the dining area and updated chef's kitchen featuring slab granite countertops, Wolf range and oven, Sub-Zero refrigeration, and a new dishwasher. The main level also includes two bedrooms, a half bath, and a laundry room. Outside, a brand-new travertine terrace and new pool create an exceptional indoor-outdoor living experience. A private gate opens directly onto Crescent Beach, where you can enjoy peaceful mornings and spectacular nightly sunsets. Upstairs, the expansive master suite offers breathtaking waterfront views, a private porch overlooking Crescent Beach, and the serene sound of waves washing ashore. Additional features include a walk-in closet and a stunning ensuite bathroom with deep green granite countertops, a soaking tub, and a walk-in shower. A second ensuite guest room completes the upper level. Meticulously maintained by only its second owner in 20 years, this home includes significant recent upgrades: new roof, new A/C systems, new pool, and refreshed landscaping and lighting. Offered furnished with high-end island-style décor. A truly one-of-a-kind opportunity to own a turnkey luxury residence in the most coveted location on Sunset Key.

4 Beds ⋅ 4 Baths ⋅ 617398 MLS

A rare opportunity to own the only active listing on the most prestigious shoreline of Sunset Key — Crescent Beach. This immaculate 4-bedroom, 3.5-bath home offers direct beach access from your backyard and showcases vibrant, dramatic island flair throughout. Upon entry, you're welcomed by soaring 25-ft ceilings, a dramatic great room with a custom chandelier, and an open layout flowing into the dining area and updated chef's kitchen featuring slab granite countertops, Wolf range and oven, Sub-Zero refrigeration, and a new dishwasher. The main level also includes two bedrooms, a half bath, and a laundry room. Outside, a brand-new travertine terrace and new pool create an exceptional indoor-outdoor living experience. A private gate opens directly onto Crescent Beach, where you can enjoy peaceful mornings and spectacular nightly sunsets. Upstairs, the expansive master suite offers breathtaking waterfront views, a private porch overlooking Crescent Beach, and the serene sound of waves washing ashore. Additional features include a walk-in closet and a stunning ensuite bathroom with deep green granite countertops, a soaking tub, and a walk-in shower. A second ensuite guest room completes the upper level. Meticulously maintained by only its second owner in 20 years, this home includes significant recent upgrades: new roof, new A/C systems, new pool, and refreshed landscaping and lighting. Offered furnished with high-end island-style décor. A truly one-of-a-kind opportunity to own a turnkey luxury residence in the most coveted location on Sunset Key.

16 Sunset, Key West

$6,600,000

Escape to Sunset Key, a private island sanctuary where refined elegance meets effortless tranquility. Just a four-minute ferry ride--operating 24 hours a day--from the vibrant charm in the heart of downtown Key West, this serene enclave offers the rare balance of seclusion and accessibility, keeping the energy of Old Town within effortless reach at any hour. This exquisite three-bedroom, three-bath beachfront home is thoughtfully designed to capture the essence of elevated island living. Wake to sweeping water views from the primary suite, and enjoy the same serene vistas from the main living area, where natural light and coastal beauty take center stage. Step outside to your private pool and spa, where you can unwind to the rhythm of waves lapping along the shoreline, all while enjoying gentle sea breezes and breathtaking sunsets over the Gulf of Mexico. The expansive main-level primary suite provides a tranquil retreat, while two beautifully appointed guest suites upstairs ensure comfort and privacy for all. Rich hardwood floors and natural stone finishes flow seamlessly throughout, complemented by a warm, sophisticated island aesthetic. Set within a private island enclave, Sunset Key offers access to exceptional amenities, including a gourmet waterfront restaurant, full-service spa, state-of-the-art fitness center, private beaches, tennis courts, and convenient ferry service. Perfectly positioned within minutes of Old Town Key West yet blissfully removed from the crowds, this secluded setting delivers a truly elevated lifestyle--where every detail is designed for quiet luxury and effortless escape.

3 Beds ⋅ 3 Baths ⋅ 619242 MLS

Escape to Sunset Key, a private island sanctuary where refined elegance meets effortless tranquility. Just a four-minute ferry ride--operating 24 hours a day--from the vibrant charm in the heart of downtown Key West, this serene enclave offers the rare balance of seclusion and accessibility, keeping the energy of Old Town within effortless reach at any hour. This exquisite three-bedroom, three-bath beachfront home is thoughtfully designed to capture the essence of elevated island living. Wake to sweeping water views from the primary suite, and enjoy the same serene vistas from the main living area, where natural light and coastal beauty take center stage. Step outside to your private pool and spa, where you can unwind to the rhythm of waves lapping along the shoreline, all while enjoying gentle sea breezes and breathtaking sunsets over the Gulf of Mexico. The expansive main-level primary suite provides a tranquil retreat, while two beautifully appointed guest suites upstairs ensure comfort and privacy for all. Rich hardwood floors and natural stone finishes flow seamlessly throughout, complemented by a warm, sophisticated island aesthetic. Set within a private island enclave, Sunset Key offers access to exceptional amenities, including a gourmet waterfront restaurant, full-service spa, state-of-the-art fitness center, private beaches, tennis courts, and convenient ferry service. Perfectly positioned within minutes of Old Town Key West yet blissfully removed from the crowds, this secluded setting delivers a truly elevated lifestyle--where every detail is designed for quiet luxury and effortless escape.

5 Sunset, Key West

$6,500,000

A Rare Investment Opportunity in the Heart of Old Town Key West. NIGHTLY rentals allowed. Introducing The Watson House—one of the largest and most versatile TRANSIENTLY licensed estates in Key West. Situated just one block off Duval Street on iconic Simonton Street, this 11-bedroom, 11-bath compound spans two distinct residences: a stately 7-bedroom mansion and a sleek, modern 4-bedroom villa—each with its own private pool. Zoned with two transient licenses and off-street parking for 4+ vehicles, this exceptional property offers unmatched flexibility for luxury rentals or private use. The grand mansion was reimagined in July 2022 by a local designer, featuring fresh paint, stylish new furnishings, and 12-foot soaring ceilings. The main level includes two guest rooms with baths, formal living and dining rooms, a parlor, and a well-appointed kitchen that opens to the pool deck and outdoor dining area. Upstairs, four en suite bedrooms include two primary suites with private balconies—one overlooking Simonton Street, the other with views of the pool. A spacious third-floor suite, accessed via an interior or exterior staircase, offers a private living room, wet bar, and yet another balcony retreat. The villa, renovated to the studs in 2014, offers a clean, contemporary design with 4 bedrooms, 4 baths, full kitchen, living area, private pool, and outdoor bar—perfect for entertaining. Whether you choose to rent the estate in its entirety or as two separate homes, The Watson House is a rare asset in Key West's luxury rental market—highly sought-after and consistently booked well in advance.

11 Beds ⋅ 11 Baths ⋅ 615623 MLS

A Rare Investment Opportunity in the Heart of Old Town Key West. NIGHTLY rentals allowed. Introducing The Watson House—one of the largest and most versatile TRANSIENTLY licensed estates in Key West. Situated just one block off Duval Street on iconic Simonton Street, this 11-bedroom, 11-bath compound spans two distinct residences: a stately 7-bedroom mansion and a sleek, modern 4-bedroom villa—each with its own private pool. Zoned with two transient licenses and off-street parking for 4+ vehicles, this exceptional property offers unmatched flexibility for luxury rentals or private use. The grand mansion was reimagined in July 2022 by a local designer, featuring fresh paint, stylish new furnishings, and 12-foot soaring ceilings. The main level includes two guest rooms with baths, formal living and dining rooms, a parlor, and a well-appointed kitchen that opens to the pool deck and outdoor dining area. Upstairs, four en suite bedrooms include two primary suites with private balconies—one overlooking Simonton Street, the other with views of the pool. A spacious third-floor suite, accessed via an interior or exterior staircase, offers a private living room, wet bar, and yet another balcony retreat. The villa, renovated to the studs in 2014, offers a clean, contemporary design with 4 bedrooms, 4 baths, full kitchen, living area, private pool, and outdoor bar—perfect for entertaining. Whether you choose to rent the estate in its entirety or as two separate homes, The Watson House is a rare asset in Key West's luxury rental market—highly sought-after and consistently booked well in advance.

525 Simonton St, Key West

$5,800,000

Experience the best of both worlds at this stunning residence on the exclusive 27-acre island of Sunset Key. Located approximately 500 yards offshore, you'll enjoy complete privacy while just a 5-minute private ferry ride from world-class dining, shopping, galleries, and nightlife. Featuring 3 beds, 3 baths, and a private pool, this waterfront home is designed to embrace water views from virtually every room. A grand entry welcomes you inside, where soaring ceilings, abundant natural light through impact windows and doors, and elegant coastal finishes immediately set the tone. The main level is thoughtfully designed for both everyday living and entertaining, featuring an open-concept Great Room, a Chef's Kitchen with premium appliances, and a spacious guest bedroom and full bath. Upstairs, a split-bedroom layout provides privacy and comfort with two luxurious suites, each offering a private balcony to enjoy the island breezes and harbor views. Step outside to your own tropical oasis, where a resort-style pool and patio create the perfect setting for relaxation. Spend your days watching boats glide through the harbor and your evenings enjoying sounds of live music drift across the water from Mallory Square. As a resident of Sunset Key, you'll enjoy access to an unmatched collection of amenities, including private sandy beaches, tennis courts, fitness center, spa, full-service concierge, 24-hour ferry, the renowned Latitudes restaurant, and beautifully maintained tropical grounds. Owners also enjoy the convenience of optional mainland parking as well as access to the private lounge while you wait for the ferry. Offering a rare combination of luxury, exclusivity, and convenience, this island retreat captures the very essence of the Key West lifestyle.

3 Beds ⋅ 3 Baths ⋅ 620287 MLS

Experience the best of both worlds at this stunning residence on the exclusive 27-acre island of Sunset Key. Located approximately 500 yards offshore, you'll enjoy complete privacy while just a 5-minute private ferry ride from world-class dining, shopping, galleries, and nightlife. Featuring 3 beds, 3 baths, and a private pool, this waterfront home is designed to embrace water views from virtually every room. A grand entry welcomes you inside, where soaring ceilings, abundant natural light through impact windows and doors, and elegant coastal finishes immediately set the tone. The main level is thoughtfully designed for both everyday living and entertaining, featuring an open-concept Great Room, a Chef's Kitchen with premium appliances, and a spacious guest bedroom and full bath. Upstairs, a split-bedroom layout provides privacy and comfort with two luxurious suites, each offering a private balcony to enjoy the island breezes and harbor views. Step outside to your own tropical oasis, where a resort-style pool and patio create the perfect setting for relaxation. Spend your days watching boats glide through the harbor and your evenings enjoying sounds of live music drift across the water from Mallory Square. As a resident of Sunset Key, you'll enjoy access to an unmatched collection of amenities, including private sandy beaches, tennis courts, fitness center, spa, full-service concierge, 24-hour ferry, the renowned Latitudes restaurant, and beautifully maintained tropical grounds. Owners also enjoy the convenience of optional mainland parking as well as access to the private lounge while you wait for the ferry. Offering a rare combination of luxury, exclusivity, and convenience, this island retreat captures the very essence of the Key West lifestyle.

293 Sunset, Key West

$5,000,000

DEVELOPERS DREAM! 4 parcels on the water with 11 ROGO's, 240' of water frontage, 10,000 sq. ft. of bay bottom. The properties are located on both sides of Hilton Haven Road. Amazing opportunity, call for appointment, please do not disturb tenants. Listing agent must accompany parties. Property is also offered to be purchased in smaller pieces, see MLS #618800, 618801 or 618802.

11 Beds ⋅ 11 Baths ⋅ 609429 MLS

DEVELOPERS DREAM! 4 parcels on the water with 11 ROGO's, 240' of water frontage, 10,000 sq. ft. of bay bottom. The properties are located on both sides of Hilton Haven Road. Amazing opportunity, call for appointment, please do not disturb tenants. Listing agent must accompany parties. Property is also offered to be purchased in smaller pieces, see MLS #618800, 618801 or 618802.

9 Hilton Haven Dr, Key West

$4,700,000

Nestled in the storied heart of Old Town Key West, this grand estate is a masterpiece of luxury & history. Spanning a majestic 8,397 sq. ft. lot, the property at 1014 Southard St. Invites you into a world where classic charm meets modern elegance. With 4 bedrooms and 3.5 Baths and over 3,000 sq. ft. of interior space across two separate structures, enjoy an unparalleled gem in one of Key West's most coveted neighborhoods. Constructed in 1899 by renowned William Cash, this estate radiates a colonial grandeur, enriched with a cranberry cut -glass transom sophisticated dark green shutters & classic french doors. The current owners have meticulously restored the property using only the finest selection of materials, from river reclaimed old growth hardwood floors in living room and hallways, to stunning Blue Castle Limestone in master suite and kitchen and continued through the magnificent garden and pool to the separate guest quarters. Smarthome features have been introduced, including Zigbee Lights integrated with Home assistant, sensor mix's, Ecobee Thermostats, 6 Node Eero Mesh Network, Abode Alarm Systems & Nest protect Sensors. The master suite located on the ground level is a peaceful sanctuary with private library & den, exceptional ensuite, three sets of French doors and opens out to the magnificent saltwater pool and tropical landscaped garden. Two additional bedrooms on second floor in main house share a bath and private veranda. Separate cottage provides exceptional guest quarters and can be accessed from Roberts Lane for additional convenience. Stunning post & beam cathedral ceilings, Limestone floor, built-in bar and kitchenette and spacious living room offers excellent space for entertaining with deck and pool access. Additional features include, One off-street parking spot, equipped with Tesla charging station & new 2023 generator powered by dual propane tanks. Welcome to Key West Living at it's finest.

4 Beds ⋅ 4 Baths ⋅ 617209 MLS

Nestled in the storied heart of Old Town Key West, this grand estate is a masterpiece of luxury & history. Spanning a majestic 8,397 sq. ft. lot, the property at 1014 Southard St. Invites you into a world where classic charm meets modern elegance. With 4 bedrooms and 3.5 Baths and over 3,000 sq. ft. of interior space across two separate structures, enjoy an unparalleled gem in one of Key West's most coveted neighborhoods. Constructed in 1899 by renowned William Cash, this estate radiates a colonial grandeur, enriched with a cranberry cut -glass transom sophisticated dark green shutters & classic french doors. The current owners have meticulously restored the property using only the finest selection of materials, from river reclaimed old growth hardwood floors in living room and hallways, to stunning Blue Castle Limestone in master suite and kitchen and continued through the magnificent garden and pool to the separate guest quarters. Smarthome features have been introduced, including Zigbee Lights integrated with Home assistant, sensor mix's, Ecobee Thermostats, 6 Node Eero Mesh Network, Abode Alarm Systems & Nest protect Sensors. The master suite located on the ground level is a peaceful sanctuary with private library & den, exceptional ensuite, three sets of French doors and opens out to the magnificent saltwater pool and tropical landscaped garden. Two additional bedrooms on second floor in main house share a bath and private veranda. Separate cottage provides exceptional guest quarters and can be accessed from Roberts Lane for additional convenience. Stunning post & beam cathedral ceilings, Limestone floor, built-in bar and kitchenette and spacious living room offers excellent space for entertaining with deck and pool access. Additional features include, One off-street parking spot, equipped with Tesla charging station & new 2023 generator powered by dual propane tanks. Welcome to Key West Living at it's finest.

1014 Southard St, Key West

$4,500,000

Step into Key West history with this remarkable property, available for the first time in generations! Located just a block from world-famous Duval Street and across from the Federal Courthouse, this property at 314 Simonton Street offers a unique blend of historic charm and modern potential. Originally a hotel with a Ford dealership on the ground floor, this three-level building is steeped in heritage. Even the legendary Ernest Hemingway chose it as his base, staying here for a month while awaiting delivery of his car in 1928. Currently set up and legally recognized as 8 units, an atrium, garage, and a pool, this property provides an unmatched opportunity for someone who loves trophy properties. Whether you envision a grand single-family estate or multi-unit living combined with commercial space on the lower level, the possibilities are endless.Don't miss the chance to own a piece of Key West's past while shaping its future with this truly one-of-a-kind property.

8 Beds ⋅ 11 Baths ⋅ 612250 MLS

Step into Key West history with this remarkable property, available for the first time in generations! Located just a block from world-famous Duval Street and across from the Federal Courthouse, this property at 314 Simonton Street offers a unique blend of historic charm and modern potential. Originally a hotel with a Ford dealership on the ground floor, this three-level building is steeped in heritage. Even the legendary Ernest Hemingway chose it as his base, staying here for a month while awaiting delivery of his car in 1928. Currently set up and legally recognized as 8 units, an atrium, garage, and a pool, this property provides an unmatched opportunity for someone who loves trophy properties. Whether you envision a grand single-family estate or multi-unit living combined with commercial space on the lower level, the possibilities are endless.Don't miss the chance to own a piece of Key West's past while shaping its future with this truly one-of-a-kind property.

314 Simonton St, Key West

$4,425,000

MOTIVATED SELLERS! Exceptional Old Town estate with pool, gardens, and 2 guest houses in the heart of Key West. This impeccable property blends timeless architecture with modern updates across three beautifully appointed structures. Behind a privacy wall & gate, the estate includes a grand main residence and two guest houses (both with kitchenettes), offering a total of four bedrooms and four-and-a-half baths. The main house welcomes you with an open floor plan, soaring ceilings, and a light-filled living and dining area. A dramatic wall of glass featuring new 40-foot impact-rated Nana doors and skylights opens to reveal lush tropical gardens and a resurfaced PebbleTec pool with a cascading waterfall. The heated, chilled, and saltwater-converted pool includes new tiled coping and a remote-controlled waterproof outdoor TV for movies or game nights under the stars. The gourmet kitchen features top-of-the-line appliances, Italian cabinetry, Silestone countertops, and a new espresso bar with wine cooler and beverage center. Real stone and hardwood floors run throughout, including two spacious bedrooms, each with an en-suite bath. The primary suite offers French doors and a spa-like bathroom with premium fixtures. The front guest house provides flexible living space currently a den or ''man cave'' with a bedroom, pantry kitchen, and a stunning bath clad in rare iridescent Czechoslovakian green glass from the 1950s. The rear guest cottage, tucked at the back of the property, includes its own sitting & dining areas, wet-bar, vaulted ceilings, a unique bath with outdoor shower & a private porch overlooking the pool & garden. Additional upgrades include a whole-house generator, new exterior lighting and irrigation by Blue Island, a state-of-the-art sound system, hurricane and plantation shutters, fresh exterior paint, and lush landscaping. 2 off-street parking spaces complete this remarkable Old Town retreat.

4 Beds ⋅ 5 Baths ⋅ 617020 MLS

MOTIVATED SELLERS! Exceptional Old Town estate with pool, gardens, and 2 guest houses in the heart of Key West. This impeccable property blends timeless architecture with modern updates across three beautifully appointed structures. Behind a privacy wall & gate, the estate includes a grand main residence and two guest houses (both with kitchenettes), offering a total of four bedrooms and four-and-a-half baths. The main house welcomes you with an open floor plan, soaring ceilings, and a light-filled living and dining area. A dramatic wall of glass featuring new 40-foot impact-rated Nana doors and skylights opens to reveal lush tropical gardens and a resurfaced PebbleTec pool with a cascading waterfall. The heated, chilled, and saltwater-converted pool includes new tiled coping and a remote-controlled waterproof outdoor TV for movies or game nights under the stars. The gourmet kitchen features top-of-the-line appliances, Italian cabinetry, Silestone countertops, and a new espresso bar with wine cooler and beverage center. Real stone and hardwood floors run throughout, including two spacious bedrooms, each with an en-suite bath. The primary suite offers French doors and a spa-like bathroom with premium fixtures. The front guest house provides flexible living space currently a den or ''man cave'' with a bedroom, pantry kitchen, and a stunning bath clad in rare iridescent Czechoslovakian green glass from the 1950s. The rear guest cottage, tucked at the back of the property, includes its own sitting & dining areas, wet-bar, vaulted ceilings, a unique bath with outdoor shower & a private porch overlooking the pool & garden. Additional upgrades include a whole-house generator, new exterior lighting and irrigation by Blue Island, a state-of-the-art sound system, hurricane and plantation shutters, fresh exterior paint, and lush landscaping. 2 off-street parking spaces complete this remarkable Old Town retreat.

1006-1008 Fleming St, Key West

$4,300,000

A Grand Historic Masterpiece! Few residences capture the true spirit of Old Town Key West quite like 406 United Street. Rooted in one of the island's most defining eras of growth and prosperity, this remarkable home is a celebration of historic craftsmanship, generous scale, and timeless value. Spanning 3,624 square feet, this 4bedroom, 4.5bath residence offers exceptional versatility, perfect for full-time living, a luxurious vacation retreat, or hosting extended family & guests. The home is being offered fully furnished, allowing for effortless enjoyment from day one. Each bedroom is spacious and thoughtfully designed with its own en suite bath, providing privacy and comfort throughout. Soaring ceilings, transom windows, and original Dade County pine walls honor the home's heritage, while modern upgrades including updated systems, surround sound, and security features blend historic charm with contemporary convenience. The chefs eat-in kitchen is both elegant and functional, featuring Viking appliances, granite countertops, and a layout ideal for entertaining. Sun-filled living spaces flow beautifully through expansive impact glass doors to the outdoors, where a heated saltwater pool and separate hot tub are surrounded by lush tropical landscaping, irrigation, and ambient lighting creating a private island oasis. Upstairs, the primary suite is a true retreat, showcasing vaulted ceilings and a spa-inspired bath with a soaking tub, multiple shower heads and dual vanities. An additional upstairs en-suite offers its own private entrance and balcony, providing flexibility for guests or extended stays. Just one block from Duval St. & the iconic Southernmost Point, with covered off-street parking, it's within walking distance to the very best of Key West's dining, nightlife, & culture. This is a rare opportunity to own a historically significant home that lives expansively, entertains effortlessly, and embodies the charm that makes Key West truly unlike anywhere else!

4 Beds ⋅ 5 Baths ⋅ 617845 MLS

A Grand Historic Masterpiece! Few residences capture the true spirit of Old Town Key West quite like 406 United Street. Rooted in one of the island's most defining eras of growth and prosperity, this remarkable home is a celebration of historic craftsmanship, generous scale, and timeless value. Spanning 3,624 square feet, this 4bedroom, 4.5bath residence offers exceptional versatility, perfect for full-time living, a luxurious vacation retreat, or hosting extended family & guests. The home is being offered fully furnished, allowing for effortless enjoyment from day one. Each bedroom is spacious and thoughtfully designed with its own en suite bath, providing privacy and comfort throughout. Soaring ceilings, transom windows, and original Dade County pine walls honor the home's heritage, while modern upgrades including updated systems, surround sound, and security features blend historic charm with contemporary convenience. The chefs eat-in kitchen is both elegant and functional, featuring Viking appliances, granite countertops, and a layout ideal for entertaining. Sun-filled living spaces flow beautifully through expansive impact glass doors to the outdoors, where a heated saltwater pool and separate hot tub are surrounded by lush tropical landscaping, irrigation, and ambient lighting creating a private island oasis. Upstairs, the primary suite is a true retreat, showcasing vaulted ceilings and a spa-inspired bath with a soaking tub, multiple shower heads and dual vanities. An additional upstairs en-suite offers its own private entrance and balcony, providing flexibility for guests or extended stays. Just one block from Duval St. & the iconic Southernmost Point, with covered off-street parking, it's within walking distance to the very best of Key West's dining, nightlife, & culture. This is a rare opportunity to own a historically significant home that lives expansively, entertains effortlessly, and embodies the charm that makes Key West truly unlike anywhere else!

406 United St, Key West

$4,250,000

Some homes are built; others are crafted with intention, atmosphere, and a sense of place. This is unmistakably the latter-a private Casa Marina sanctuary conceived for the purest expression of Key West living. Set on a prime corner lot and discreetly veiled behind mature landscaping this contemporary compound unfolds like a resort, revealing a world of light, scale, and serenity. The moment you enter, the great room rises dramatically with soaring ceilings and a full expanse of nano-wall glass that dissolves the boundary between indoors and out. The view extends across an all-tile infinity pool, fire-lit relaxation cabana, and lush tropical gardens all designed by Craig Reynolds designed for quiet retreat and/or entertaining. Comprising two architecturally harmonious structures totaling three bedrooms and three-and-a-half baths, the estate balances openness with privacy. The main residence offers two bedrooms, two-and-a-half baths, a den, and an additional office or sitting room off the primary suite. The primary bath is a study in thoughtful luxury, with distinct his-and-hers sides. Heavy wood doors and subtle Balinese influences lend warmth and soul to the home's clean, modern lines. The separate one-bedroom, one-bath guest cottage-with its own loft creates an ideal retreat for guests or extended stays, offering independence without sacrificing connection to the property's central oasis. Designed for those who love to cook and entertain, the chef's kitchen anchors the main living space, while a granite-topped outdoor grill extends the experience outdoors. Impact glass, electric hurricane shutters, tile floors, a heated pool and separate spa, irrigation system, outdoor lighting, a whole-house generator and a Sonos system ensure the home lives as effortlessly as it looks. While meticulously maintained with off street parking on both sides of the property, this gem stands as a rare fusion of privacy, craftsmanship, and resort-style living

3 Beds ⋅ 4 Baths ⋅ 619613 MLS

Some homes are built; others are crafted with intention, atmosphere, and a sense of place. This is unmistakably the latter-a private Casa Marina sanctuary conceived for the purest expression of Key West living. Set on a prime corner lot and discreetly veiled behind mature landscaping this contemporary compound unfolds like a resort, revealing a world of light, scale, and serenity. The moment you enter, the great room rises dramatically with soaring ceilings and a full expanse of nano-wall glass that dissolves the boundary between indoors and out. The view extends across an all-tile infinity pool, fire-lit relaxation cabana, and lush tropical gardens all designed by Craig Reynolds designed for quiet retreat and/or entertaining. Comprising two architecturally harmonious structures totaling three bedrooms and three-and-a-half baths, the estate balances openness with privacy. The main residence offers two bedrooms, two-and-a-half baths, a den, and an additional office or sitting room off the primary suite. The primary bath is a study in thoughtful luxury, with distinct his-and-hers sides. Heavy wood doors and subtle Balinese influences lend warmth and soul to the home's clean, modern lines. The separate one-bedroom, one-bath guest cottage-with its own loft creates an ideal retreat for guests or extended stays, offering independence without sacrificing connection to the property's central oasis. Designed for those who love to cook and entertain, the chef's kitchen anchors the main living space, while a granite-topped outdoor grill extends the experience outdoors. Impact glass, electric hurricane shutters, tile floors, a heated pool and separate spa, irrigation system, outdoor lighting, a whole-house generator and a Sonos system ensure the home lives as effortlessly as it looks. While meticulously maintained with off street parking on both sides of the property, this gem stands as a rare fusion of privacy, craftsmanship, and resort-style living

1320 Grinnell St, Key West

$4,200,000

924 Flagler is an iconic home in the sought after Casa Marina area. Totally renovated and upgraded, this home has received multiple design and restoration awards. The incredible property has over 12,300 square feet of expansive grounds including meandering walkways, an outbuilding, a two car garage. It features lush tropical landscaping and spralling open spaces. The interior of this concrete home features 14 ft. ceilings on the first floor and 12' on the second floor. A sunroom entry is lined with Palladian doors and opens to a patio and the living room. An office, powder room, large dining room and the chef's kitchen complete the first floor. The second floor features the primary bedroom and a sitting room converted from a fourth bedroom plus two more guest bedrooms and a bath. A spacious second floor sun porch offers beautiful views and more space to relax. The list of improvements, upgrades and amenities is extensive and include hurricane rated roofs over the home and the garage, custom mahogany wood windows and doors, copper gutters and downspouts to a 7,000 gallon cistern used for irrigation, custom Hanson & Bringle millwork and cabinetry, Cat 5 & 6 wiring, McIntosh audio system throughout the house, a whole house generator, updated electric and plumbing, an electronic gated driveway. This one of a kind home is a Key West treasure in an excellent location.

4 Beds ⋅ 3 Baths ⋅ 617929 MLS

924 Flagler is an iconic home in the sought after Casa Marina area. Totally renovated and upgraded, this home has received multiple design and restoration awards. The incredible property has over 12,300 square feet of expansive grounds including meandering walkways, an outbuilding, a two car garage. It features lush tropical landscaping and spralling open spaces. The interior of this concrete home features 14 ft. ceilings on the first floor and 12' on the second floor. A sunroom entry is lined with Palladian doors and opens to a patio and the living room. An office, powder room, large dining room and the chef's kitchen complete the first floor. The second floor features the primary bedroom and a sitting room converted from a fourth bedroom plus two more guest bedrooms and a bath. A spacious second floor sun porch offers beautiful views and more space to relax. The list of improvements, upgrades and amenities is extensive and include hurricane rated roofs over the home and the garage, custom mahogany wood windows and doors, copper gutters and downspouts to a 7,000 gallon cistern used for irrigation, custom Hanson & Bringle millwork and cabinetry, Cat 5 & 6 wiring, McIntosh audio system throughout the house, a whole house generator, updated electric and plumbing, an electronic gated driveway. This one of a kind home is a Key West treasure in an excellent location.

924 Flagler Ave, Key West

$4,000,000

MAJOR PRICE IMPROVEMENT! This beautiful Key West home on two lots just blocks from the Atlantic Ocean has undergone a total property renovation including a magnificent addition. Quality materials and custom finishes have been utilized to produce a luxurious yet casually elegant 4BR/3.5BA single level home with two cottages, generous gated off street parking, heated/chilled pool and amenities aplenty. Old Key West greets you at the entry gates with historic Old Town curbstones flowing through the lush landscaping designed by Craig Reynolds. Architect, William Horn, has thoughtfully redesigned the home, pool cottage and guest cottage which can amazingly transform into a garage should you choose. The expansive Great Room is a WOW with gleaming Dade County Pine floors and soaring ceilings. French doors and banks of tall windows provide long views of the inviting pool, spacious decking and tropical foliage. Grand Chef's kitchen with Wolf appliances, floor to ceiling custom cabinetry and walk-in pantry. The handsome primary bedroom suite with sumptuous bath and shower includes dual custom closets and a glorious private sun room that also opens to the pool. Outdoor kitchen, private outdoor shower, Big A*s Fans, smart home technology, Sonos system, indoor/outdoor speakers, security cameras, tank-less hot water heater, generator and enormous propane tank are but a few of the many amenities of this spectacular property. No expense has been spared to create the ultimate Key West home for private indoor and outdoor island living. Can easily be Turn Key/Move In Ready! Furniture, furnishings, electronics, household goods, 4 electric bikes, electric golf car and artwork are all available to be purchased separately should you desire a seamless, stress-free and immediate occupancy upon closing.

4 Beds ⋅ 4 Baths ⋅ 618030 MLS

MAJOR PRICE IMPROVEMENT! This beautiful Key West home on two lots just blocks from the Atlantic Ocean has undergone a total property renovation including a magnificent addition. Quality materials and custom finishes have been utilized to produce a luxurious yet casually elegant 4BR/3.5BA single level home with two cottages, generous gated off street parking, heated/chilled pool and amenities aplenty. Old Key West greets you at the entry gates with historic Old Town curbstones flowing through the lush landscaping designed by Craig Reynolds. Architect, William Horn, has thoughtfully redesigned the home, pool cottage and guest cottage which can amazingly transform into a garage should you choose. The expansive Great Room is a WOW with gleaming Dade County Pine floors and soaring ceilings. French doors and banks of tall windows provide long views of the inviting pool, spacious decking and tropical foliage. Grand Chef's kitchen with Wolf appliances, floor to ceiling custom cabinetry and walk-in pantry. The handsome primary bedroom suite with sumptuous bath and shower includes dual custom closets and a glorious private sun room that also opens to the pool. Outdoor kitchen, private outdoor shower, Big A*s Fans, smart home technology, Sonos system, indoor/outdoor speakers, security cameras, tank-less hot water heater, generator and enormous propane tank are but a few of the many amenities of this spectacular property. No expense has been spared to create the ultimate Key West home for private indoor and outdoor island living. Can easily be Turn Key/Move In Ready! Furniture, furnishings, electronics, household goods, 4 electric bikes, electric golf car and artwork are all available to be purchased separately should you desire a seamless, stress-free and immediate occupancy upon closing.

1227 Washington St, Key West

$3,950,000

New Construction & Furnished in Key West. Experience timeless Key West charm blended with modern luxury in this stunning property, re-built completely to the historic standard of the original home. Located in the highly sought-after Casa Marina neighborhood just five blocks from Higgs Beach and six blocks from Duval Street, this residence offers the ideal balance of privacy and proximity to all that Key West has to offer. Step inside to discover over 900 square feet of wraparound Brazilian hardwood porches and a beautifully designed interior featuring custom-stained Heart Pine floors, Shiplap walls, and an abundance of natural light. The wide entrance hallway leads to a soaring great room with 20-foot ceilings and skylights, seamlessly connecting the living, dining, and kitchen spaces. The chef's kitchen is a true showpiece, boasting a large center island with seating for six, a wet bar, dual pantries, and a full Viking Professional appliance package. The main level includes a spacious master suite and two guest bedrooms, each with private baths and individual porch access. A convenient half bath is located off the hallway, while the laundry room--complete with an additional half bath--opens directly to the back deck and pool area. Enjoy Key West's outdoor lifestyle with a 15' x 8' pool with water feature, custom mahogany impact doors with transoms, impact windows, and lush professional landscaping. Upstairs, the charm continues with two additional ensuite bedrooms, walk-in closets, an interior balcony overlooking the great room, and a massive air-conditioned storage space spanning half of the second floor. Additional features include: Buried 250-gallon propane tank (servicing gas stove, on-demand water heater, generator-ready) and off-street parking with gate. This exceptional Casa Marina residence offers the best of Key West living--historic elegance, impeccable craftsmanship, and modern comforts.

5 Beds ⋅ 7 Baths ⋅ 620098 MLS

New Construction & Furnished in Key West. Experience timeless Key West charm blended with modern luxury in this stunning property, re-built completely to the historic standard of the original home. Located in the highly sought-after Casa Marina neighborhood just five blocks from Higgs Beach and six blocks from Duval Street, this residence offers the ideal balance of privacy and proximity to all that Key West has to offer. Step inside to discover over 900 square feet of wraparound Brazilian hardwood porches and a beautifully designed interior featuring custom-stained Heart Pine floors, Shiplap walls, and an abundance of natural light. The wide entrance hallway leads to a soaring great room with 20-foot ceilings and skylights, seamlessly connecting the living, dining, and kitchen spaces. The chef's kitchen is a true showpiece, boasting a large center island with seating for six, a wet bar, dual pantries, and a full Viking Professional appliance package. The main level includes a spacious master suite and two guest bedrooms, each with private baths and individual porch access. A convenient half bath is located off the hallway, while the laundry room--complete with an additional half bath--opens directly to the back deck and pool area. Enjoy Key West's outdoor lifestyle with a 15' x 8' pool with water feature, custom mahogany impact doors with transoms, impact windows, and lush professional landscaping. Upstairs, the charm continues with two additional ensuite bedrooms, walk-in closets, an interior balcony overlooking the great room, and a massive air-conditioned storage space spanning half of the second floor. Additional features include: Buried 250-gallon propane tank (servicing gas stove, on-demand water heater, generator-ready) and off-street parking with gate. This exceptional Casa Marina residence offers the best of Key West living--historic elegance, impeccable craftsmanship, and modern comforts.

1311 Grinnell St, Key West

$3,875,000

Welcome to the ''Polynesian Courtyard Retreat''. Set within the highly sought-after Casa Marina neighborhood, this exceptional Key West estate offers a rare private tropical sanctuary on an expansive 11,220 sq ft lot. Surrounded by lush, mature landscaping with tropical and fruit trees, the property creates a serene island retreat designed for both relaxation and entertaining. The main residence features 4 bedrooms and 3 baths, with elegant living spaces that seamlessly connect to the outdoors with each bedroom opening to the beautifully landscaped grounds. A sparkling pool anchors the outdoor oasis, providing ample space for gatherings and island living at its finest. Tucked discreetly among the gardens is a charming detached guest cottage, offering a secluded retreat complete with a full bath, sauna, and living area—perfect for guests, extended family, or a private studio. In addition to the home's rarity is a two-car garage with parking for five or more additional vehicles, an exceptional feature in Key West. Ideally located within walking distance to beaches, tennis and pickleball courts, children's and dog parks, and the iconic White Street Pier, this home is also just minutes from Duval Street's renowned dining, entertainment, art, and theater scene. A truly special opportunity to own a private estate that captures the essence of Key West living.

5 Beds ⋅ 4 Baths ⋅ 618052 MLS

Welcome to the ''Polynesian Courtyard Retreat''. Set within the highly sought-after Casa Marina neighborhood, this exceptional Key West estate offers a rare private tropical sanctuary on an expansive 11,220 sq ft lot. Surrounded by lush, mature landscaping with tropical and fruit trees, the property creates a serene island retreat designed for both relaxation and entertaining. The main residence features 4 bedrooms and 3 baths, with elegant living spaces that seamlessly connect to the outdoors with each bedroom opening to the beautifully landscaped grounds. A sparkling pool anchors the outdoor oasis, providing ample space for gatherings and island living at its finest. Tucked discreetly among the gardens is a charming detached guest cottage, offering a secluded retreat complete with a full bath, sauna, and living area—perfect for guests, extended family, or a private studio. In addition to the home's rarity is a two-car garage with parking for five or more additional vehicles, an exceptional feature in Key West. Ideally located within walking distance to beaches, tennis and pickleball courts, children's and dog parks, and the iconic White Street Pier, this home is also just minutes from Duval Street's renowned dining, entertainment, art, and theater scene. A truly special opportunity to own a private estate that captures the essence of Key West living.

905 Von Phister St, Key West

$3,800,000

The wait for perfection has concluded at 1314 Johnson Street. Brand new and never lived in, this pristine masterpiece is where architectural integrity meets the effortless spirit of the Key West lifestyle. Situated just two blocks from the iconic Casa Marina Resort and the beautiful sands of Higgs Beach, this residence offers a rare combination of 3,400 square feet of sophisticated interior living and nearly 2,900 square feet of private, expansive decking. Arrival is marked by a sense of total seclusion, ensured by a secure perimeter and a private electric driveway gate. The home's exterior is finished in premium Hardie board siding, complemented by high-impact windows and doors that provide both architectural beauty and absolute peace of mind. Inside, the home unfolds with wide-plank white oak flooring, eight-foot solid core doors, and soaring ceilings. A stunning chef's kitchen serves as the home's vibrant center, featuring professional-grade Viking appliances, crisp white cabinetry, a striking navy blue island, and Carrara quartz countertops. Designed for the modern host, the home's foundation is defined by dual primary suites—one on each level—providing guests with an unparalleled and private retreat. Each of the four bedrooms features walk-in closets and a private ensuite bath showcasing James Martin vanities and elegant tile work. The interior transitions seamlessly to a secluded outdoor oasis, where a 10' x 20' heated pool and soothing waterfall feature provide a tranquil backdrop for the full alfresco summer kitchen. From the whole-house generator to the low-maintenance composite decking, every element of this turnkey, never-lived-in estate has been meticulously selected for the buyer who demands the highest standard of luxury. Beyond a mere residence, this brand-new sanctuary stands as an exquisite retreat waiting for you to call home.

4 Beds ⋅ 6 Baths ⋅ 618135 MLS

The wait for perfection has concluded at 1314 Johnson Street. Brand new and never lived in, this pristine masterpiece is where architectural integrity meets the effortless spirit of the Key West lifestyle. Situated just two blocks from the iconic Casa Marina Resort and the beautiful sands of Higgs Beach, this residence offers a rare combination of 3,400 square feet of sophisticated interior living and nearly 2,900 square feet of private, expansive decking. Arrival is marked by a sense of total seclusion, ensured by a secure perimeter and a private electric driveway gate. The home's exterior is finished in premium Hardie board siding, complemented by high-impact windows and doors that provide both architectural beauty and absolute peace of mind. Inside, the home unfolds with wide-plank white oak flooring, eight-foot solid core doors, and soaring ceilings. A stunning chef's kitchen serves as the home's vibrant center, featuring professional-grade Viking appliances, crisp white cabinetry, a striking navy blue island, and Carrara quartz countertops. Designed for the modern host, the home's foundation is defined by dual primary suites—one on each level—providing guests with an unparalleled and private retreat. Each of the four bedrooms features walk-in closets and a private ensuite bath showcasing James Martin vanities and elegant tile work. The interior transitions seamlessly to a secluded outdoor oasis, where a 10' x 20' heated pool and soothing waterfall feature provide a tranquil backdrop for the full alfresco summer kitchen. From the whole-house generator to the low-maintenance composite decking, every element of this turnkey, never-lived-in estate has been meticulously selected for the buyer who demands the highest standard of luxury. Beyond a mere residence, this brand-new sanctuary stands as an exquisite retreat waiting for you to call home.

1314 Johnson, Key West

$3,700,000

Experience refined island living in this BRAND NEW residence perfectly situated on a generous 10,800 square foot lot and elevated at an impressive 10.5 feet. This 3 bedroom, 3.5 bath home is a testament to modern coastal luxury, where timeless design meets effortless functionality. Constructed entirely of concrete, the open concept layout is framed by soaring cathedral ceilings and expansive impact-glass doors that bathe the interiors in natural light and invite the outdoors in. Premium finishes and high end appliances enhance every detail, creating a sophisticated yet comfortable living environment. The home features two primary suites — one upstairs and one downstairs — each with private outdoor access for seamless indoor-outdoor living. A separate, fully equipped guest cottage offers privacy and tranquility, complete with wide sliding doors that capture lush garden views. Designed by renowned landscape architect Craig Reynolds, the tropical grounds are a private oasis. Multiple covered patios surround the heated and chilled pool with sun shelf seating, while a striking coral rock outdoor shower adds a touch of island luxury. Additional features include a 481 square foot garage for parking and storage, a whole house Generac generator, standing seam metal roof, and all impact rated windows and doors, ensuring peace of mind and durability. Every element of this turnkey property has been curated with precision and care, resulting in a one-of-a-kind retreat that embodies the essence of elegant coastal living in Key West.

3 Beds ⋅ 4 Baths ⋅ 617013 MLS

Experience refined island living in this BRAND NEW residence perfectly situated on a generous 10,800 square foot lot and elevated at an impressive 10.5 feet. This 3 bedroom, 3.5 bath home is a testament to modern coastal luxury, where timeless design meets effortless functionality. Constructed entirely of concrete, the open concept layout is framed by soaring cathedral ceilings and expansive impact-glass doors that bathe the interiors in natural light and invite the outdoors in. Premium finishes and high end appliances enhance every detail, creating a sophisticated yet comfortable living environment. The home features two primary suites — one upstairs and one downstairs — each with private outdoor access for seamless indoor-outdoor living. A separate, fully equipped guest cottage offers privacy and tranquility, complete with wide sliding doors that capture lush garden views. Designed by renowned landscape architect Craig Reynolds, the tropical grounds are a private oasis. Multiple covered patios surround the heated and chilled pool with sun shelf seating, while a striking coral rock outdoor shower adds a touch of island luxury. Additional features include a 481 square foot garage for parking and storage, a whole house Generac generator, standing seam metal roof, and all impact rated windows and doors, ensuring peace of mind and durability. Every element of this turnkey property has been curated with precision and care, resulting in a one-of-a-kind retreat that embodies the essence of elegant coastal living in Key West.

3741 Eagle Ave, Key West

$3,300,000

Discover a rare investment and lifestyle opportunity at 'Zen Villa,' a prestigious compound anchored in the coveted X-Flood Zone of Old Town, Key West. Spanning a spacious 5,891 SF lot, this unique offering encompasses three distinct residences: the luxurious main estate at 400 Aronovitz Lane and two charming, income-generating cottages at 621 and 623 Whitehead Street. The main residence is a masterpiece of contemporary island design. Step inside to an airy lounge defined by soaring 18-foot cathedral ceilings and a chic wet bar featuring granite finishes and a premium beverage center—perfect for entertaining. The open-concept floor plan dissolves the lines between indoors and out, leading you through expansive glass sliders to a tropical sanctuary. Designed by renowned landscape architect Craig Reynolds, the private courtyard features a heated pool with a tranquil water feature, lush native flora, and ambient lighting. Accommodations in the main house are nothing short of spectacular. The first-floor primary suite serves as a spa-like retreat with marble finishes and a steam shower. Upstairs, a second primary suite offers a private covered porch with an outdoor shower, while a cozy guest room invites relaxation with a deep soaking tub. The value of this compound is unmatched, with the two Whitehead Street cottages (1BD/1BA each) providing immediate rental income or flexible guest housing. Zoned Historic Residential Office (HRO) with an ADA-compliant entrance, the property offers versatile live-work possibilities. Complete with 3+ off-street parking spaces and located steps from Duval Street and Fort Zachary Taylor, Zen Villa is your ultimate key to paradise.

5 Beds ⋅ 6 Baths ⋅ 615720 MLS

Discover a rare investment and lifestyle opportunity at 'Zen Villa,' a prestigious compound anchored in the coveted X-Flood Zone of Old Town, Key West. Spanning a spacious 5,891 SF lot, this unique offering encompasses three distinct residences: the luxurious main estate at 400 Aronovitz Lane and two charming, income-generating cottages at 621 and 623 Whitehead Street. The main residence is a masterpiece of contemporary island design. Step inside to an airy lounge defined by soaring 18-foot cathedral ceilings and a chic wet bar featuring granite finishes and a premium beverage center—perfect for entertaining. The open-concept floor plan dissolves the lines between indoors and out, leading you through expansive glass sliders to a tropical sanctuary. Designed by renowned landscape architect Craig Reynolds, the private courtyard features a heated pool with a tranquil water feature, lush native flora, and ambient lighting. Accommodations in the main house are nothing short of spectacular. The first-floor primary suite serves as a spa-like retreat with marble finishes and a steam shower. Upstairs, a second primary suite offers a private covered porch with an outdoor shower, while a cozy guest room invites relaxation with a deep soaking tub. The value of this compound is unmatched, with the two Whitehead Street cottages (1BD/1BA each) providing immediate rental income or flexible guest housing. Zoned Historic Residential Office (HRO) with an ADA-compliant entrance, the property offers versatile live-work possibilities. Complete with 3+ off-street parking spaces and located steps from Duval Street and Fort Zachary Taylor, Zen Villa is your ultimate key to paradise.

400 Aronovitz Ln, Key West

$3,250,000

Situated in the prestigious heart of Old Town, 906 Southard Street is an impeccably restored Historic Key West eyebrow house filled with timeless architectural character. This Home has off street parking, pool and all that Key West Charm you are looking for. A large ipe wood front porch adorned with classic gingerbread trim and iconic gas lanterns welcomes you to the refined residence. This home offers three (3) spacious bedrooms, each with its own private ensuite bathroom, ensuring comfort and privacy for residents and guests alike. The gourmet kitchen is a chef's masterpiece, featuring Carrera marble countertops, cherrywood cabinets, a gas Viking Professional range, two Liebherr refrigerators, and a dedicated ice maker and wine fridge. Adjacent, the skylight-lit dining area provides an inviting, sophisticated setting perfect for both intimate dinners and entertaining. Designed for indoor-outdoor living, the property features an outdoor dining area, with an ipe wood covered porch, a heated pool with waterfall feature, surrounded by lush tropical landscaping for complete relaxation and privacy. Additional premium amenities include a whole house generator, brick-paved, gated driveway with car port, and a spacious storage shed for added convenience. Thoughtfully curated and beautifully appointed, this exceptional residence offers a rare opportunity to own a piece of Key West history while enjoying the finest modern comforts. Call today for your private showing! Some photo have been virtually staged.

3 Beds ⋅ 3 Baths ⋅ 617607 MLS

Situated in the prestigious heart of Old Town, 906 Southard Street is an impeccably restored Historic Key West eyebrow house filled with timeless architectural character. This Home has off street parking, pool and all that Key West Charm you are looking for. A large ipe wood front porch adorned with classic gingerbread trim and iconic gas lanterns welcomes you to the refined residence. This home offers three (3) spacious bedrooms, each with its own private ensuite bathroom, ensuring comfort and privacy for residents and guests alike. The gourmet kitchen is a chef's masterpiece, featuring Carrera marble countertops, cherrywood cabinets, a gas Viking Professional range, two Liebherr refrigerators, and a dedicated ice maker and wine fridge. Adjacent, the skylight-lit dining area provides an inviting, sophisticated setting perfect for both intimate dinners and entertaining. Designed for indoor-outdoor living, the property features an outdoor dining area, with an ipe wood covered porch, a heated pool with waterfall feature, surrounded by lush tropical landscaping for complete relaxation and privacy. Additional premium amenities include a whole house generator, brick-paved, gated driveway with car port, and a spacious storage shed for added convenience. Thoughtfully curated and beautifully appointed, this exceptional residence offers a rare opportunity to own a piece of Key West history while enjoying the finest modern comforts. Call today for your private showing! Some photo have been virtually staged.

906 Southard St, Key West

$3,250,000

This British designer has spent over twenty years crafting contemporary properties in a luxurious Caribbean setting. Well-known for attention to detail and a commitment to sourcing the finest materials, this builder's constructions are exceptional. The spacious living room effortlessly merges with the outdoors upon opening the storm-proof sliding doors, creating a seamless transition between interior and exterior space..........The house features elegant tile floors throughout the first floor, while the second level is distinguished by luxurious hickory wood flooring. The dining room is tailored to accommodate a bespoke layout, complete with ambient mood lighting and refined cove molding. A a generously proportioned bedroom and bathroom, complete with private access to the pool area, are nestled at the rear of the first floor. This stunning four-bedroom, five-bathroom residence boasts an impressive 2,628 square feet of living space, set amidst a meticulously landscaped 5,600 square-foot lot. The masterful landscaping is the work of a renowned expert, celebrated for work on the most exclusive properties in the Florida Keys..........The main bedroom of this stunning residence has a beautiful bathroom with soaking tub, huge closet and sliding doors that open onto the upstairs balcony. The expansive wrap-around balcony also provides access to the two additional bedrooms, each featuring their own bathroom. The property's reflective metal cool roof is engineered to optimize energy efficiency and provide year-round comfort. Three independent air conditioning units ensure a consistently cool environment. There is also a 500 gallon underground gas tank and a 2.2 kw house generator. Additional features include off-street parking for multiple vehicles, a private driveway, and secure electronic gates and security camera system, solidifying this property's reputation as a masterpiece of timeless craftsmanship. Once you step inside, its allure will undoubtedly capture your heart

4 Beds ⋅ 5 Baths ⋅ 616940 MLS

This British designer has spent over twenty years crafting contemporary properties in a luxurious Caribbean setting. Well-known for attention to detail and a commitment to sourcing the finest materials, this builder's constructions are exceptional. The spacious living room effortlessly merges with the outdoors upon opening the storm-proof sliding doors, creating a seamless transition between interior and exterior space..........The house features elegant tile floors throughout the first floor, while the second level is distinguished by luxurious hickory wood flooring. The dining room is tailored to accommodate a bespoke layout, complete with ambient mood lighting and refined cove molding. A a generously proportioned bedroom and bathroom, complete with private access to the pool area, are nestled at the rear of the first floor. This stunning four-bedroom, five-bathroom residence boasts an impressive 2,628 square feet of living space, set amidst a meticulously landscaped 5,600 square-foot lot. The masterful landscaping is the work of a renowned expert, celebrated for work on the most exclusive properties in the Florida Keys..........The main bedroom of this stunning residence has a beautiful bathroom with soaking tub, huge closet and sliding doors that open onto the upstairs balcony. The expansive wrap-around balcony also provides access to the two additional bedrooms, each featuring their own bathroom. The property's reflective metal cool roof is engineered to optimize energy efficiency and provide year-round comfort. Three independent air conditioning units ensure a consistently cool environment. There is also a 500 gallon underground gas tank and a 2.2 kw house generator. Additional features include off-street parking for multiple vehicles, a private driveway, and secure electronic gates and security camera system, solidifying this property's reputation as a masterpiece of timeless craftsmanship. Once you step inside, its allure will undoubtedly capture your heart

1610 South Street, Key West

$3,200,000

Located on Georgia Street, this stunning newly built retreat captures the timeless charm of Key West with a sophisticated modern twist, offering a lifestyle of exceptional luxury just one block from the beach and the Casa Marina district. This beautifully designed residence features four bedrooms, each serving as a private sanctuary complete with spa-inspired en-suite baths and spacious walk-in closets. A serene palette of calming hues is elevated by elegant Eastern Accents linens, custom window treatments, and handcrafted wood shutters that welcome the island breeze. Designer wallpaper worthy of an Architectural Digest feature adds artistry and personality throughout, transforming every bedroom into a luxurious retreat. The open-concept floor plan seamlessly blends indoor and outdoor living, creating an effortless setting for both relaxation and entertaining. The gourmet kitchen, elegant dining area, and inviting living spaces all flow beautifully together while overlooking the spectacular saltwater pool. Outside, sleek glass railings, and lush mature landscaping create a private, resort-style oasis where every day feels like a vacation. The kitchen is truly a showpiece -- a masterful blend of form and function where every detail has been thoughtfully curated. A large statement island anchors the space, inviting conversation. Brass-accented light fixtures cast a warm glow overhead, perfectly complementing the stunning designer backsplash and layered finishes that bring the entire space together. Additional features include impact-resistant windows and patio doors, as well as convenient off-street parking.

4 Beds ⋅ 5 Baths ⋅ 620048 MLS

Located on Georgia Street, this stunning newly built retreat captures the timeless charm of Key West with a sophisticated modern twist, offering a lifestyle of exceptional luxury just one block from the beach and the Casa Marina district. This beautifully designed residence features four bedrooms, each serving as a private sanctuary complete with spa-inspired en-suite baths and spacious walk-in closets. A serene palette of calming hues is elevated by elegant Eastern Accents linens, custom window treatments, and handcrafted wood shutters that welcome the island breeze. Designer wallpaper worthy of an Architectural Digest feature adds artistry and personality throughout, transforming every bedroom into a luxurious retreat. The open-concept floor plan seamlessly blends indoor and outdoor living, creating an effortless setting for both relaxation and entertaining. The gourmet kitchen, elegant dining area, and inviting living spaces all flow beautifully together while overlooking the spectacular saltwater pool. Outside, sleek glass railings, and lush mature landscaping create a private, resort-style oasis where every day feels like a vacation. The kitchen is truly a showpiece -- a masterful blend of form and function where every detail has been thoughtfully curated. A large statement island anchors the space, inviting conversation. Brass-accented light fixtures cast a warm glow overhead, perfectly complementing the stunning designer backsplash and layered finishes that bring the entire space together. Additional features include impact-resistant windows and patio doors, as well as convenient off-street parking.

1522 Georgia St, Key West

$3,100,000

Exquisite Old Town residence just completed! Rare opportunity to own your Key West dream home designed to satisfy both peace of mind and self-indulging luxuries. This historic structure has been rebuilt from the foundation up to create the perfect harmony of historic restoration, structural integrity and custom design. Luxurious 5 bed/ 4 bath including a detached poolside cabana and off-street parking. An exceptional floor plan perfectly combines open concept living and defined spaces with attention to both function and elegance. Practice your culinary skills in a luxury kitchen with a high end appliance package to include Viking and Subzero. Delight in the perfect combination of indoor/outdoor living with custom door wall and sliders off bedrooms that lead to vast covered porches both up and down that cater to space for both dining and lounging Relax around the custom pool with sun shelf and waterfall or on the sunny poolside patio surrounded with tropical vegetation. Located in the X flood zone plus new roof and new impact windows/doors throughout lend itself to energy saving, sound proofing, insurance discounts and ease of ownership. An ideal combination of historic character,a modern floor plan, sprawling spaces and designer finishes await you in this Key West dream home!

5 Beds ⋅ 4 Baths ⋅ 617913 MLS

Exquisite Old Town residence just completed! Rare opportunity to own your Key West dream home designed to satisfy both peace of mind and self-indulging luxuries. This historic structure has been rebuilt from the foundation up to create the perfect harmony of historic restoration, structural integrity and custom design. Luxurious 5 bed/ 4 bath including a detached poolside cabana and off-street parking. An exceptional floor plan perfectly combines open concept living and defined spaces with attention to both function and elegance. Practice your culinary skills in a luxury kitchen with a high end appliance package to include Viking and Subzero. Delight in the perfect combination of indoor/outdoor living with custom door wall and sliders off bedrooms that lead to vast covered porches both up and down that cater to space for both dining and lounging Relax around the custom pool with sun shelf and waterfall or on the sunny poolside patio surrounded with tropical vegetation. Located in the X flood zone plus new roof and new impact windows/doors throughout lend itself to energy saving, sound proofing, insurance discounts and ease of ownership. An ideal combination of historic character,a modern floor plan, sprawling spaces and designer finishes await you in this Key West dream home!

1114 Grinnell St, Key West

$3,100,000

Some homes are renovated. This one was restored - with the kind of patience and reverence that only comes once in a generation. 1230 South Street is a five-bedroom, five-and-a-half-bath estate that stands apart not simply for what it has, but for what it represents: a masterwork of historical accuracy and modern luxury, executed without compromise. Original Dade County Pine runs throughout the interiors, grounding the home in its authentic Key West heritage. Rich ipe decking frames the outdoor living spaces with warmth and permanence. Every impact-rated window and door has been selected to honor the home's historic character while delivering the peace of mind today's discerning buyer expects. At the heart of the property, a brand-new heated pool anchors the lush tropical grounds - part private resort, part quiet sanctuary. A newly constructed pool cottage extends the possibilities further, offering rare flexibility for guests, extended family, or a private studio. On an island where space is increasingly precious, this kind of versatility is genuinely hard to find. Inside, natural light moves generously through rooms that shift effortlessly between intimate and expansive. Each bedroom suite has been thoughtfully considered - private, refined, unhurried. The boundary between indoors and out dissolves entirely. But 1230 South Street carries a significance that no spec sheet can fully capture. It is among the final projects of Michael Pelkey, the beloved Key West designer whose work helped define the island's aesthetic for decades. His signature is everywhere - restrained yet soulful, luxurious yet deeply rooted in place. To live here is to inhabit a piece of Key West design history. To own it is to become its steward. Steps from beaches, dining, and the cultural heartbeat of the island, yet fully removed from it when you want to be - this is the rare offering that delivers on every promise. Not just a home. A legacy.

5 Beds ⋅ 6 Baths ⋅ 618118 MLS

Some homes are renovated. This one was restored - with the kind of patience and reverence that only comes once in a generation. 1230 South Street is a five-bedroom, five-and-a-half-bath estate that stands apart not simply for what it has, but for what it represents: a masterwork of historical accuracy and modern luxury, executed without compromise. Original Dade County Pine runs throughout the interiors, grounding the home in its authentic Key West heritage. Rich ipe decking frames the outdoor living spaces with warmth and permanence. Every impact-rated window and door has been selected to honor the home's historic character while delivering the peace of mind today's discerning buyer expects. At the heart of the property, a brand-new heated pool anchors the lush tropical grounds - part private resort, part quiet sanctuary. A newly constructed pool cottage extends the possibilities further, offering rare flexibility for guests, extended family, or a private studio. On an island where space is increasingly precious, this kind of versatility is genuinely hard to find. Inside, natural light moves generously through rooms that shift effortlessly between intimate and expansive. Each bedroom suite has been thoughtfully considered - private, refined, unhurried. The boundary between indoors and out dissolves entirely. But 1230 South Street carries a significance that no spec sheet can fully capture. It is among the final projects of Michael Pelkey, the beloved Key West designer whose work helped define the island's aesthetic for decades. His signature is everywhere - restrained yet soulful, luxurious yet deeply rooted in place. To live here is to inhabit a piece of Key West design history. To own it is to become its steward. Steps from beaches, dining, and the cultural heartbeat of the island, yet fully removed from it when you want to be - this is the rare offering that delivers on every promise. Not just a home. A legacy.

1230 South Street, Key West

$3,050,000

A true Key West classic. The kind of home people come here dreaming of finding. Tucked away in the Casa Marina neighborhood, one of the island's most coveted enclaves, this property captures that unmistakable blend of tropical elegance, privacy, and effortless island living. The location alone is exceptional. Just three blocks from the beach, tennis courts, and a short stroll to some of Key West's best dining. But it's what happens beyond the gates that truly sets this home apart. Inside, the design is both refined and inviting. Custom built by an award winning architect, the home is filled with natural light, soaring ceilings, and a seamless connection between indoor and outdoor living. Every space flows effortlessly into the next, leading you out to a lush tropical oasis that feels completely private. An incredible orchid garden, mature landscaping, and multiple outdoor living areas create a setting that is both tranquil and unforgettable. The primary suite opens to its own private terrace, perfect for quiet mornings or unwinding at the end of the day. Guest spaces each enjoy their own connection to the outdoors, offering comfort and privacy for everyone. And behind the beauty, there is substance. This home has been meticulously maintained and thoughtfully upgraded with impact features, solar panels, a whole home generator, updated mechanical systems, and smart home technology throughout. It is designed for both peace of mind and modern convenience. Whether you are looking for the perfect winter escape or a full time residence, this home delivers something rare. Easy. Effortless. And unmistakably Key West.

3 Beds ⋅ 3 Baths ⋅ 619421 MLS

A true Key West classic. The kind of home people come here dreaming of finding. Tucked away in the Casa Marina neighborhood, one of the island's most coveted enclaves, this property captures that unmistakable blend of tropical elegance, privacy, and effortless island living. The location alone is exceptional. Just three blocks from the beach, tennis courts, and a short stroll to some of Key West's best dining. But it's what happens beyond the gates that truly sets this home apart. Inside, the design is both refined and inviting. Custom built by an award winning architect, the home is filled with natural light, soaring ceilings, and a seamless connection between indoor and outdoor living. Every space flows effortlessly into the next, leading you out to a lush tropical oasis that feels completely private. An incredible orchid garden, mature landscaping, and multiple outdoor living areas create a setting that is both tranquil and unforgettable. The primary suite opens to its own private terrace, perfect for quiet mornings or unwinding at the end of the day. Guest spaces each enjoy their own connection to the outdoors, offering comfort and privacy for everyone. And behind the beauty, there is substance. This home has been meticulously maintained and thoughtfully upgraded with impact features, solar panels, a whole home generator, updated mechanical systems, and smart home technology throughout. It is designed for both peace of mind and modern convenience. Whether you are looking for the perfect winter escape or a full time residence, this home delivers something rare. Easy. Effortless. And unmistakably Key West.

1020 Von Phister St, Key West

$3,050,000

'For Statistical Purposes Only'

4 Beds ⋅ 3 Baths ⋅ 619395 MLS

'For Statistical Purposes Only'

421 Virginia St, Key West

$2,950,000

1420 Whalton Street is a masterfully engineered beautifully furnished luxury residence where elevated construction, refined design, and resort-style amenities converge in one of Key West's most desirable residential neighborhoods. This move-in ready gem was built by Shaw Construction in 2023 with Insulated Concrete Form (ICF) construction and reinforced rebar, the home offers exceptional structural integrity, energy efficiency, and prepped for solar for long term durability. The structure is thoughtfully elevated for peace of mind. Hurricane impact glass is installed throughout. The private outdoor oasis features a saltwater pool with 6-foot depth, integrated spa jets, and true spa-style pool configuration, surrounded by a professionally designed tropical landscape. Approved gazebo plans convey. Inside, 10-foot ceilings and reclaimed Dade County pine floors bring warmth and character throughout. The home offers four en-suite bedrooms plus a dedicated powder room, along with a laundry/utility room, custom dog room, and attic storage. The chef's kitchen is equipped with Sub-Zero, Wolf, and Cove appliances, including a Sub-Zero beverage cooler and wine cooler, and custom cabinetry by Hansen & Bringle, the most respected high-end local cabinet maker. Comfort is engineered with two top-of-the-line American Standard/Trane multi-speed A/C systems, featuring zoned climate control, built-in humidification, and UV air purification. The Pneumatic Vacuum Elevator (PVE) for your convenience is efficient, quiet and low-maintenance. Additional highlights include a top-tier security system with cameras, wiring for a MusicCast sound system, Hunter Douglas Duette shades, solar-ready conduits, and a high-capacity propane system with premium generator capable of powering the home for up to 10 days, supported by a dedicated A/C sub-panel. A rare opportunity to own a technically advanced, beautifully finished luxury residence in the heart of Key We

4 Beds ⋅ 5 Baths ⋅ 617916 MLS

1420 Whalton Street is a masterfully engineered beautifully furnished luxury residence where elevated construction, refined design, and resort-style amenities converge in one of Key West's most desirable residential neighborhoods. This move-in ready gem was built by Shaw Construction in 2023 with Insulated Concrete Form (ICF) construction and reinforced rebar, the home offers exceptional structural integrity, energy efficiency, and prepped for solar for long term durability. The structure is thoughtfully elevated for peace of mind. Hurricane impact glass is installed throughout. The private outdoor oasis features a saltwater pool with 6-foot depth, integrated spa jets, and true spa-style pool configuration, surrounded by a professionally designed tropical landscape. Approved gazebo plans convey. Inside, 10-foot ceilings and reclaimed Dade County pine floors bring warmth and character throughout. The home offers four en-suite bedrooms plus a dedicated powder room, along with a laundry/utility room, custom dog room, and attic storage. The chef's kitchen is equipped with Sub-Zero, Wolf, and Cove appliances, including a Sub-Zero beverage cooler and wine cooler, and custom cabinetry by Hansen & Bringle, the most respected high-end local cabinet maker. Comfort is engineered with two top-of-the-line American Standard/Trane multi-speed A/C systems, featuring zoned climate control, built-in humidification, and UV air purification. The Pneumatic Vacuum Elevator (PVE) for your convenience is efficient, quiet and low-maintenance. Additional highlights include a top-tier security system with cameras, wiring for a MusicCast sound system, Hunter Douglas Duette shades, solar-ready conduits, and a high-capacity propane system with premium generator capable of powering the home for up to 10 days, supported by a dedicated A/C sub-panel. A rare opportunity to own a technically advanced, beautifully finished luxury residence in the heart of Key We

1420 Whalton St, Key West