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A truly one-of-one legacy estate set on Sunset Key, one of the most coveted and private islands in the Florida Keys. Just minutes by boat from Key West, this extraordinary waterfront residence offers unmatched privacy, scale, and architectural distinction. Positioned on nearly an acre and the largest homesite on the island, this classically inspired estate was designed by a renowned Naples-based architect in a modified Bermuda style. Timeless in design and rich in detail, the home reflects exceptional craftsmanship throughout. The main residence features soaring ceilings with intricate custom moldings, marble and hardwood floors, and a magnificent great room with expansive glass doors opening to a wraparound lanai, creating seamless indoor-outdoor living with sweeping sunset and open-water views. The home offers three bedrooms, three full baths, and two half baths, complemented by a detached one-bedroom, one-bath guest house. Designed for both grand entertaining and everyday living, the estate flows effortlessly between interior and exterior spaces. Highlights include a grand entertainer's kitchen with oversized island seating and bespoke cabinetry, a custom wet bar with glass-front cabinetry and stone counters, multiple indoor sitting and lounge areas, a garage and a gated entry with circular brick drive. Outdoor living is elevated by expansive covered verandas, sun terraces, and a resort-style pool and spa adorned with custom mosaic artwork, an unforgettable setting for incredible sunsets, intimate gatherings, or live music under the stars. From nearly every vantage point, enjoy ever-changing water views with passing cruise ships, yachts, fishing boats, and frequent dolphin sightings. Sunset Key residents enjoy private beaches, a fitness center, spa, tennis courts, the acclaimed Latitudes restaurant, and a full suite of resort-style amenities. A rare opportunity to own one of the most distinctive properties ever offered in the Florida Keys.

4 Beds ⋅ 6 Baths ⋅ 618455 MLS

A truly one-of-one legacy estate set on Sunset Key, one of the most coveted and private islands in the Florida Keys. Just minutes by boat from Key West, this extraordinary waterfront residence offers unmatched privacy, scale, and architectural distinction. Positioned on nearly an acre and the largest homesite on the island, this classically inspired estate was designed by a renowned Naples-based architect in a modified Bermuda style. Timeless in design and rich in detail, the home reflects exceptional craftsmanship throughout. The main residence features soaring ceilings with intricate custom moldings, marble and hardwood floors, and a magnificent great room with expansive glass doors opening to a wraparound lanai, creating seamless indoor-outdoor living with sweeping sunset and open-water views. The home offers three bedrooms, three full baths, and two half baths, complemented by a detached one-bedroom, one-bath guest house. Designed for both grand entertaining and everyday living, the estate flows effortlessly between interior and exterior spaces. Highlights include a grand entertainer's kitchen with oversized island seating and bespoke cabinetry, a custom wet bar with glass-front cabinetry and stone counters, multiple indoor sitting and lounge areas, a garage and a gated entry with circular brick drive. Outdoor living is elevated by expansive covered verandas, sun terraces, and a resort-style pool and spa adorned with custom mosaic artwork, an unforgettable setting for incredible sunsets, intimate gatherings, or live music under the stars. From nearly every vantage point, enjoy ever-changing water views with passing cruise ships, yachts, fishing boats, and frequent dolphin sightings. Sunset Key residents enjoy private beaches, a fitness center, spa, tennis courts, the acclaimed Latitudes restaurant, and a full suite of resort-style amenities. A rare opportunity to own one of the most distinctive properties ever offered in the Florida Keys.

19 Sunset, Key West

$18,250,000

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

$14,500,000

Located just a block from Duval Street, Cabana Inn is hidden amongst shady trees to create a tranquil paradise. The historic conch estate, with cottages that were meticulously converted into a comfortable Key West hotel, features modern designs throughout the interior and exterior. Featuring 24 rooms that can accommodate one to five people, the Cabana Inn offers ten room types. Hotel amenities include lush interior courtyards, a refreshing lagoon style pool, a spacious in-ground Jacuzzi, and a large sun-yard with treetop walkways.

611313 MLS

Located just a block from Duval Street, Cabana Inn is hidden amongst shady trees to create a tranquil paradise. The historic conch estate, with cottages that were meticulously converted into a comfortable Key West hotel, features modern designs throughout the interior and exterior. Featuring 24 rooms that can accommodate one to five people, the Cabana Inn offers ten room types. Hotel amenities include lush interior courtyards, a refreshing lagoon style pool, a spacious in-ground Jacuzzi, and a large sun-yard with treetop walkways.

409 Applerouth Ln, 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

$9,000,000

**FOR STATISTICAL PURPOSES ONLY** Located in picturesque Old Town of Key West, just steps from lively Duval Street, Douglas House is a captivating guest house ensemble. Spanning across five interconnected lots, with dual street access from both Amelia and Virginia Streets, this property is a remarkable collection of 15 licensed transient accommodations and a historic 5-COP liquor license + a parking lot. Douglas House, a cherished Inn, stands out for its perfect balance of accessibility and affordability, coupled with its recent renovations, ensuring it remains in pristine condition. At its heart lies a beautifully designed pool and bar area, enveloped by lush, tropical greenery, offering a tranquil oasis amidst the vibrancy of Key West. The guest house presents a variety of lodging options, from cozy queen rooms to expansive suites equipped with bars and kitchens, all featuring a modern decor. Many of these suites offer the added luxury of private porches or balconies, overlooking the garden and pool. Guests are treated to an array of amenities including a refreshing swimming pool, a charming bar area, off-street parking, and relaxing garden spaces with winding brick paths. Complimentary Wi-Fi and tea & coffee service add to the comfort of the stay. Moreover, the Douglas House is within a short stroll of Key West's renowned attractions such as the Ernest Hemingway House, Southernmost Point Monument, and Sunset Pier at Mallory Square, not to mention the array of galleries, eateries, bars, and shops nearby. Parking lot at corner of Amelia St at 1108 Whitehead St. also for sale for guest parking & added income.

15 Beds ⋅ 16 Baths ⋅ 617393 MLS

**FOR STATISTICAL PURPOSES ONLY** Located in picturesque Old Town of Key West, just steps from lively Duval Street, Douglas House is a captivating guest house ensemble. Spanning across five interconnected lots, with dual street access from both Amelia and Virginia Streets, this property is a remarkable collection of 15 licensed transient accommodations and a historic 5-COP liquor license + a parking lot. Douglas House, a cherished Inn, stands out for its perfect balance of accessibility and affordability, coupled with its recent renovations, ensuring it remains in pristine condition. At its heart lies a beautifully designed pool and bar area, enveloped by lush, tropical greenery, offering a tranquil oasis amidst the vibrancy of Key West. The guest house presents a variety of lodging options, from cozy queen rooms to expansive suites equipped with bars and kitchens, all featuring a modern decor. Many of these suites offer the added luxury of private porches or balconies, overlooking the garden and pool. Guests are treated to an array of amenities including a refreshing swimming pool, a charming bar area, off-street parking, and relaxing garden spaces with winding brick paths. Complimentary Wi-Fi and tea & coffee service add to the comfort of the stay. Moreover, the Douglas House is within a short stroll of Key West's renowned attractions such as the Ernest Hemingway House, Southernmost Point Monument, and Sunset Pier at Mallory Square, not to mention the array of galleries, eateries, bars, and shops nearby. Parking lot at corner of Amelia St at 1108 Whitehead St. also for sale for guest parking & added income.

419 Amelia 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

$6,350,000

GRAND KEY OASIS is the epitome of luxurious island living, featuring two separate homes connected by a covered pavilion. This fabulous compound is being offered fully furnished with the main house just completely redecorated at a cost of over $100,000. The interior design will leave you marveling at the attention to detail and the sheer luxury of every room. You'll notice from the moment you enter that there's no shortage of 'grand' touches throughout this luxurious home. The living area of the main house is large enough for your whole family to gather comfortably. Everyone has a seat to watch your favorite show or the big game on the large Flat Screen TV, or simply kick back and relax in your lush surroundings. The guest house also has a living area on the second floor, giving those guests a comfortable space to relax and enjoy. Both living areas have a bathroom conveniently located nearby. The property includes a large garage for two vehicles, plus gated parking for two more...unheard of in Old Town. However, the real showstopper of GRAND KEY OASIS is the backyard, complete with one of the largest private swimming pools in Key West. The pool area, which gets plenty of sun all day long, will undoubtedly be a primary gathering spot for your group. Privacy is in abundance as the entire pool area is fenced in and surrounded by lush tropical landscaping. Spend your days swimming laps in the spacious pool or relaxing poolside in the many chaise lounges that line the deck. When you're ready to escape the sun, grab a cool drink at the outdoor covered bar complete with a huge 80'' flat screen TV. Fire up the propane grill and enjoy a BBQ using the outdoor dining set. BEST OF ALL, THIS HOME CAN BE RENTED MONTHLY WITH GROSS ANNUAL INCOME OF $300,000 OR MORE, AND STILL LEAVE PLENTY OF TIME FOR YOUR OWN FAMILY TO ENJOY IT.

5 Beds ⋅ 6 Baths ⋅ 616897 MLS

GRAND KEY OASIS is the epitome of luxurious island living, featuring two separate homes connected by a covered pavilion. This fabulous compound is being offered fully furnished with the main house just completely redecorated at a cost of over $100,000. The interior design will leave you marveling at the attention to detail and the sheer luxury of every room. You'll notice from the moment you enter that there's no shortage of 'grand' touches throughout this luxurious home. The living area of the main house is large enough for your whole family to gather comfortably. Everyone has a seat to watch your favorite show or the big game on the large Flat Screen TV, or simply kick back and relax in your lush surroundings. The guest house also has a living area on the second floor, giving those guests a comfortable space to relax and enjoy. Both living areas have a bathroom conveniently located nearby. The property includes a large garage for two vehicles, plus gated parking for two more...unheard of in Old Town. However, the real showstopper of GRAND KEY OASIS is the backyard, complete with one of the largest private swimming pools in Key West. The pool area, which gets plenty of sun all day long, will undoubtedly be a primary gathering spot for your group. Privacy is in abundance as the entire pool area is fenced in and surrounded by lush tropical landscaping. Spend your days swimming laps in the spacious pool or relaxing poolside in the many chaise lounges that line the deck. When you're ready to escape the sun, grab a cool drink at the outdoor covered bar complete with a huge 80'' flat screen TV. Fire up the propane grill and enjoy a BBQ using the outdoor dining set. BEST OF ALL, THIS HOME CAN BE RENTED MONTHLY WITH GROSS ANNUAL INCOME OF $300,000 OR MORE, AND STILL LEAVE PLENTY OF TIME FOR YOUR OWN FAMILY TO ENJOY IT.

326 Caroline St, Key West

$6,300,000

The Royal Compound is currently generating $500,000 a year from first-class guests who will accept only the best in vacation homes. What's interesting is that most of the rental income comes from monthly rentals, so you can expect almost as much income without a transient license. This extraordinary home is situated on one of the largest lots (14,183 SF) in Truman Annex and is being offered as the ultimate turnkey property. There are a total of 5 bedrooms and 4 bathrooms: 3 bedrooms and 2 bathrooms in the main house and two 1 bedroom, 1 bathroom private cottages. This expansive property includes a covered seating and dining area under the gazebo, which overlooks the resort-style heated pool and outdoor kitchen. The value of this home is not only its privacy with exotic landscaping, but its ability to generate income when you are away. Schedule your private showing of The Royal Compound to appreciate the uniqueness of this one-of-a-kind property!

5 Beds ⋅ 4 Baths ⋅ 612065 MLS

The Royal Compound is currently generating $500,000 a year from first-class guests who will accept only the best in vacation homes. What's interesting is that most of the rental income comes from monthly rentals, so you can expect almost as much income without a transient license. This extraordinary home is situated on one of the largest lots (14,183 SF) in Truman Annex and is being offered as the ultimate turnkey property. There are a total of 5 bedrooms and 4 bathrooms: 3 bedrooms and 2 bathrooms in the main house and two 1 bedroom, 1 bathroom private cottages. This expansive property includes a covered seating and dining area under the gazebo, which overlooks the resort-style heated pool and outdoor kitchen. The value of this home is not only its privacy with exotic landscaping, but its ability to generate income when you are away. Schedule your private showing of The Royal Compound to appreciate the uniqueness of this one-of-a-kind property!

101 Admirals Ln, 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

$5,745,000

Located in the heart of Old Town, this truly magical estate presents an opportunity to own a private compound of remarkable scale and architectural distinction. Set on an oversized lot with off-street parking for two, the property features two fully independent residences--each appointed with impact-rated windows and doors. Situated along iconic Millionaire's Row, the main residence is a masterfully restored historic home that pays homage to its original character while embracing today's highest standards of luxury and comfort. Offering four spacious ensuite bedrooms, the main home includes a versatile first-floor suite that can easily function as a first floor primary bedroom or den. Additional features include original Dade County pine walls, reclaimed river wood flooring, soaring ceilings, and generous windows that bathe the interiors in natural light. At the heart of the home lies a chef-caliber gourmet kitchen with custom cabinetry, Sub-Zero and Wolf appliances, sculpted marble countertops, a built-in wine cooler and dedicated coffee center. French doors open to the wraparound porches- offering an idyllic setting for morning coffee, sunset cocktails, or alfresco dining. The estate's newly constructed guest house features two additional ensuite bedrooms, dramatic vaulted ceilings, and a charming loft ideal for additional living. The fully equipped kitchen features high-end Miele appliances and striking artisan tile. Anchoring the property is an extraordinary outdoor living environment conceived by renowned landscape architect Craig Reynolds. This lush, resort-style sanctuary showcases a sparkling saline swimming pool, cascading waterfall, outdoor shower, and a discreet poolside half bath. 1109 Fleming is more than a residence--it is a landmark Old Town estate equally suited for full-time living, a refined second home, or a legacy property to be enjoyed for generations on one of Key West's most prestigious streets.

6 Beds ⋅ 7 Baths ⋅ 617783 MLS

Located in the heart of Old Town, this truly magical estate presents an opportunity to own a private compound of remarkable scale and architectural distinction. Set on an oversized lot with off-street parking for two, the property features two fully independent residences--each appointed with impact-rated windows and doors. Situated along iconic Millionaire's Row, the main residence is a masterfully restored historic home that pays homage to its original character while embracing today's highest standards of luxury and comfort. Offering four spacious ensuite bedrooms, the main home includes a versatile first-floor suite that can easily function as a first floor primary bedroom or den. Additional features include original Dade County pine walls, reclaimed river wood flooring, soaring ceilings, and generous windows that bathe the interiors in natural light. At the heart of the home lies a chef-caliber gourmet kitchen with custom cabinetry, Sub-Zero and Wolf appliances, sculpted marble countertops, a built-in wine cooler and dedicated coffee center. French doors open to the wraparound porches- offering an idyllic setting for morning coffee, sunset cocktails, or alfresco dining. The estate's newly constructed guest house features two additional ensuite bedrooms, dramatic vaulted ceilings, and a charming loft ideal for additional living. The fully equipped kitchen features high-end Miele appliances and striking artisan tile. Anchoring the property is an extraordinary outdoor living environment conceived by renowned landscape architect Craig Reynolds. This lush, resort-style sanctuary showcases a sparkling saline swimming pool, cascading waterfall, outdoor shower, and a discreet poolside half bath. 1109 Fleming is more than a residence--it is a landmark Old Town estate equally suited for full-time living, a refined second home, or a legacy property to be enjoyed for generations on one of Key West's most prestigious streets.

1109 Fleming St, 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

$4,300,000

Step into your stunning dream home with tropical light and refined elegance. 1217 Johnson Street is where luxury meets island soul. Situated on one of Key West's most serene streets, this newly built sanctuary rises safely above floodwaters, crafted with Category 5 hurricane resilience, impact windows and doors, a steadfast generator, and durable Hardie board siding. Set on a 6,160 sq ft lot in a peaceful neighborhood just steps from Higgs Beach and the White Street Pier, this 5 bedroom, 6 bath home seamlessly blends modern design and island charm. The conch-style architecture welcomes you with a classic front porch, leading inside to more than 3,600 sq ft of living space with beautiful wood floors. Inside, a dramatic two-story foyer with stacked glass frames views of the saltwater pool and waterfall. Glass doors open wide to merge the living area with the lushly landscaped outdoor space, perfect for entertaining. A gazebo offers a shady spot to relax, while the poolside cabana includes a bath for added convenience. The chef's kitchen, crafted by Hansen & Bringle, is a showpiece with quartz counters, shaker-style cabinets, a luxurious waterfall island, and professional grade Viking appliances. Upstairs are three bedrooms, including two primary suites with Juliet balconies that capture refreshing ocean breezes, plus a versatile room which could be an office, gym, or an enormous closet. Landscape lighting, irrigation and secure gated off-street parking for 2 adds peace of mind. Walk or bike to nearby beaches, savor sunset strolls, and let every day feel like a gentle escape. Your private oasis in Key West awaits. Offered fully furnished with a few exclusions, as well as a 2025 Icon Golf Cart, a 2023 Honda Rukus Scooter & a 2023 Honda Trail Scooter.

5 Beds ⋅ 6 Baths ⋅ 617517 MLS

Step into your stunning dream home with tropical light and refined elegance. 1217 Johnson Street is where luxury meets island soul. Situated on one of Key West's most serene streets, this newly built sanctuary rises safely above floodwaters, crafted with Category 5 hurricane resilience, impact windows and doors, a steadfast generator, and durable Hardie board siding. Set on a 6,160 sq ft lot in a peaceful neighborhood just steps from Higgs Beach and the White Street Pier, this 5 bedroom, 6 bath home seamlessly blends modern design and island charm. The conch-style architecture welcomes you with a classic front porch, leading inside to more than 3,600 sq ft of living space with beautiful wood floors. Inside, a dramatic two-story foyer with stacked glass frames views of the saltwater pool and waterfall. Glass doors open wide to merge the living area with the lushly landscaped outdoor space, perfect for entertaining. A gazebo offers a shady spot to relax, while the poolside cabana includes a bath for added convenience. The chef's kitchen, crafted by Hansen & Bringle, is a showpiece with quartz counters, shaker-style cabinets, a luxurious waterfall island, and professional grade Viking appliances. Upstairs are three bedrooms, including two primary suites with Juliet balconies that capture refreshing ocean breezes, plus a versatile room which could be an office, gym, or an enormous closet. Landscape lighting, irrigation and secure gated off-street parking for 2 adds peace of mind. Walk or bike to nearby beaches, savor sunset strolls, and let every day feel like a gentle escape. Your private oasis in Key West awaits. Offered fully furnished with a few exclusions, as well as a 2025 Icon Golf Cart, a 2023 Honda Rukus Scooter & a 2023 Honda Trail Scooter.

1217 Johnson 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

$4,225,000

Discover the charm of 515 Amelia St., a stunning TRANSIENT residence with a strong rental history. Nestled on a tranquil dead-end street, just one block from the vibrant Duval Street in Key West, this exceptional home offers off-street parking for two vehicles. Designed for entertaining, 515 Amelia St. features an expansive open floor plan that seamlessly connects the spacious living room to the kitchen, creating the perfect setting for gatherings. Step outside to enjoy one of the largest private pools on the island, surrounded by a beautifully landscaped backyard that includes a half bath and outdoor shower—ideal for lounging, dining, or barbecuing in complete privacy. Brand New Roof This remarkable home boasts five well-appointed bedrooms and six bathrooms. One suite includes a kitchenette and separate living area. You can walk or bike to local attractions, dining, shopping, and beaches. Don't miss out on this incredible opportunity to own a TRANSIENT RENTAL PROPERTY IN OLD TOWN KEY WEST!!

5 Beds ⋅ 6 Baths ⋅ 618222 MLS

Discover the charm of 515 Amelia St., a stunning TRANSIENT residence with a strong rental history. Nestled on a tranquil dead-end street, just one block from the vibrant Duval Street in Key West, this exceptional home offers off-street parking for two vehicles. Designed for entertaining, 515 Amelia St. features an expansive open floor plan that seamlessly connects the spacious living room to the kitchen, creating the perfect setting for gatherings. Step outside to enjoy one of the largest private pools on the island, surrounded by a beautifully landscaped backyard that includes a half bath and outdoor shower—ideal for lounging, dining, or barbecuing in complete privacy. Brand New Roof This remarkable home boasts five well-appointed bedrooms and six bathrooms. One suite includes a kitchenette and separate living area. You can walk or bike to local attractions, dining, shopping, and beaches. Don't miss out on this incredible opportunity to own a TRANSIENT RENTAL PROPERTY IN OLD TOWN KEY WEST!!

515 Amelia 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

$3,750,000

Welcome to 517 Elizabeth Street, located in one of the most prestigious neighborhoods on the island, and in the heart of Old Town Key West. This 4 bedroom, 4 bathroom home offers the perfect combination of Key West charm and tropical living. Just two blocks from the famous Duval Street, and three blocks from Historic Seaport, this home is in prime walking distance to endless opportunities. The first floor consists of a mixed-use office space accompanied by an expansive master bedroom equipped with a spacious walk-in closet and a newly renovated en suite, double vanity bathroom. The beautiful kitchen flows into an open floor plan with an additional ½ bath, living room, and dining room. Multiple sets of sliding glass doors lead out to an outdoor living area and pool complete with a waterfall. Completely redesigned by Craig Reynolds, the backyard lends a quiet escape with lush foliage providing 360° of privacy, and a secluded outdoor shower for rinsing off the salty Key West air. The second floor boasts 3 bedrooms, 1 ½ baths, and a large street- facing balcony, making it perfect to host family and friends. Other notable features: Off-street parking, large enough to fit both a car and golf cart. This home is located in X flood zone. Call for your private showing today!

4 Beds ⋅ 4 Baths ⋅ 616104 MLS

Welcome to 517 Elizabeth Street, located in one of the most prestigious neighborhoods on the island, and in the heart of Old Town Key West. This 4 bedroom, 4 bathroom home offers the perfect combination of Key West charm and tropical living. Just two blocks from the famous Duval Street, and three blocks from Historic Seaport, this home is in prime walking distance to endless opportunities. The first floor consists of a mixed-use office space accompanied by an expansive master bedroom equipped with a spacious walk-in closet and a newly renovated en suite, double vanity bathroom. The beautiful kitchen flows into an open floor plan with an additional ½ bath, living room, and dining room. Multiple sets of sliding glass doors lead out to an outdoor living area and pool complete with a waterfall. Completely redesigned by Craig Reynolds, the backyard lends a quiet escape with lush foliage providing 360° of privacy, and a secluded outdoor shower for rinsing off the salty Key West air. The second floor boasts 3 bedrooms, 1 ½ baths, and a large street- facing balcony, making it perfect to host family and friends. Other notable features: Off-street parking, large enough to fit both a car and golf cart. This home is located in X flood zone. Call for your private showing today!

517 Elizabeth St, 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