Old Town ~ Unrecord Properties For Sale - Homes and Condos in Old Town ~ Unrecord Key West, Florida

LOCATION! LOCATION! LOCATION! You do not want to miss out on the opportunity to own one of the most sought after properties in Old Town Key West, a truly special home and lot that you MUST see in person. Permitted for transient license receivership HRCC1 (buyer to verify). The ONLY single family home on the market with DIRECT access to DUVAL Street via a walking lane. Remarkably secluded and completely hidden from view. The moment you step behind the gate, you will feel that you have entered your own tropical paradise. Add a pool and expand on this beautiful 4200 square foot lot. Zoned as a non contributing structure with HARC (buyer to verify), this is a restoration project. This is the first time the property has ever been on the market!

Freshly renovated throughout and nestled on one of Old Towns most coveted streets, youll discover this captivating home steeped in rich history. The kitchen has new granite counters, new stainless-steel appliances & has been opened up to completely transform the space creating a modern feel and functional room. The Richard Roberts home, originally transported from Green Turtle Cay, Bahamas in 1847, stands as a cherished Key West icon. With 4 or 5 bedrooms, 3 baths, plus an office space (or 5th bedroom), its versatile floor plan offers endless possibilities. Enjoy the outdoors with four inviting porches (two on each side), warm wood pine walls, and heart pine floors throughout, this residence has earned 2 stars through the years from the Historical Florida Keys foundation. A wonderful great room or downstairs primary suite effortlessly spills onto a side yard deck & jacuzzi. Access to the second floor is via an outdoor staircase and the third floor hosts a generous bedroom and bath suite or could also serve as two bedrooms. This historically significant home is a true Key West landmark. Just 3 blocks from Duval St. & the waterfront, its quiet neighborhood is walkable to all the shops, galleries & fine restaurants.

Located in the prestigious gated Truman Annex, this beautifully appointed 2-bedroom, 2.5-bath home offers refined coastal living just steps from Duval Street and Truman Waterfront. Thoughtfully designed with elegant finishes and an open, airy layout, this residence is perfect for those seeking a private sanctuary in Old Town.A private entrance welcomes you into a turn-key interior, where Serena & Lily accents and carefully curated decor create a sophisticated yet relaxed atmosphere. The kitchen features Bosch stainless steel appliances, an induction oven, a farmhouse sink, and a waterfall-edge peninsula with bar seating. The open-concept dining and living areas are designed for both comfort and style, with striking furnishings, a large wall-mounted TV, and plenty of space for entertaining. Two sets of French doors lead to a private, lushly landscaped patio, offering a peaceful retreat for outdoor dining and relaxation. A first-floor powder room adds convenience.Upstairs, 2 bedrooms each with a king size bed provide a luxurious escape. The primary suite boasts French doors opening to a covered balcony, perfect for enjoying the island breeze. The ensuite bath features dual sinks, waterfall faucets, and a beautifully tiled walk-in shower. Down the hall, the second bedroom is a tranquil retreat with ample closet space and access to a hall bath with a walk-in shower.The outdoor space is designed for year-round enjoyment, with a fully fenced paver patio, seating, and a grill. Just a short walk away, the heated community pool offers lounge chairs, shaded tables, and restroom facilities. A designated parking space is conveniently located just steps from the home.216 Fleming Street is just mere blocks away from world-class dining, shopping, and entertainment. This home presently has a transient license and future bookings through 2025 in place. Whether youre looking for a full-time residence, a vacation home, or an investment opportunity, this home offers it all.

This home has not been sold in over 100 years! The property sits on the corner of world famous Millionaire Row and one of the last not to be renovated. Do not buy someone elses overpriced flip. Bring your imagination, contractor and bring this home back to its original beauty. The lot is almost 5000 SF and runs from Fleming St. to Stickeny Lane, where there is ample off-street parking. The 1890 Sanborn maps show an additional house on the property, that may be able to be rebuilt with permission from the city (buyers to verify). The home has plenty of the original Dade County pine waiting for restoration. Also featuring historic windows and double balconies. Currently the home is a legal duplex, each a 2 bedroom, 1 bath apartment. Buyers could retain the duplex or transform it into a stunning single family residence in the most sought after neighborhood in all of Key West.

This home has not been sold in over 100 years! The property sits on the corner of world famous Millionaire Row and one of the last not to be renovated. Do not buy someone elses overpriced flip. Bring your imagination, contractor and bring this home back to its original beauty. The lot is almost 5000 SF and runs from Fleming St. to Stickeny Lane, where there is ample off-street parking. The 1890 Sanborn maps show an additional house on the property, that may be able to be rebuilt with permission from the city (buyers to verify). The home has plenty of the original Dade County pine waiting for restoration. Also featuring historic windows and double balconies. Currently the home is a legal duplex, each a 2 bedroom, 1 bath apartment. Buyers could retain the duplex or transform it into a stunning single family residence in the most sought after neighborhood in all of Key West.

Situated in the coveted Historic Seaport neighborhood, 1015 Eaton Street offers charm and convenience, creating the ultimate Key West lifestyle. This meticulously reimagined Historic Eyebrow home offers 4 bedrooms and 3 bathrooms thoughtfully designed for quintessential island life. As you enter through the white picket fence, the home welcomes you with an inviting front porch, ideal for soaking in the sights and energy of this sought-after neighborhood. Upon opening the front door adorned with a stained glass transom, you are greeted by Dade County pine floors and walls lined with elegant wallpaper. The airy open-concept kitchen and living space are highlighted by soaring ceilings and a waterfall island. Stainless steel appliances and a marble counter top complete this ideal chefs kitchen. Natural light cascades through expansive wall-to-wall sliding glass doors, seamlessly connecting the indoor and outdoor living areas.The main-level primary ensuite bedroom features a luxurious bath with a basalt accent wall, sleek natural finishes, and direct access to the pool area. A first-floor ensuite guest bedroom and two additional upstairs bedrooms ensure plenty of space for family and friends. Each bathroom features custom anti-fog mirrors, porcelain tiles, and exquisite accents, blending functionality with sophisticated design. IPE decking along with a dazzling saltwater pool and adjoining hot tub with a glass mosaic-tiled waterfall sets the stage for relaxation and entertaining. This fully fenced backyard oasis offers the ideal space for tanning and unwinding after a long day on the island.With its unbeatable location and close proximity to all Key West has to offer, from eclectic boutiques, waterfront dining, or the islands renowned attraction, 1015 Eaton Street offers a rare opportunity to embrace the vibrancy of island life. Schedule your private showing today and make this Historic Seaport home yours!

Triplex investment property! Prime location only 1 block from the historic Key West seaport and 2 blocks from Duval St. The downstairs offers 2 units which include a 1/1 with kitchenette and a 1/1 with full kitchen. Enjoy the front porch facing Caroline St. or spend a lazy afternoon lounging by the dip pool in the backyard. Ascend the gorgeous wooden staircase to the upstairs unit which includes the 2nd and 3rd floors and has many features reminiscent of an old ship accented by beautifully detailed wood trim. This 2/3 unit includes hardwood floors, stained glass details, a loft/office, a front porch for relaxing, a small back porch overlooking the pool, and a unique widows walk where you can enjoy a bit of privacy in the treetops. The kitchen includes a built-in water filtration system, the master bedroom is a generous size, and youll find storage galore throughout the home with built-ins, nooks, and crannies. This historic home has high ceilings throughout, and the windows (except skylights) are hurricane rated. The owners currently live in the upstairs unit and use the first-floor units as monthly vacation rentals. Any of the units could be used as long-term rentals, or the property could potentially be converted into an up/down duplex or returned to its original configuration as a single-family home. Enjoy the close proximity to all the amenities this great location offers in Old Town. This historic gem is awaiting your vision.

Welcome home to 531 Frances Street, located in the heart of old town Key West within walking distance to shops, restuarants, harbor walk and Duval. From the white picket fence to the wide front porch, this charming home is a classic. The first floor features an open floor plan with high ceilings and gorgeous natural light. The living room, dining and kitchen all open to the decked pool area. A covered loggia is perfect for outdoor dining, entertaining or relaxing rain or shine. The heated blue tiled pool is the focal point for the outdoor space. The primary bedroom with en-suite bathroom, den/third bedroom with walk-in closet and convenient half bath are also located on the first floor. Upstairs is a guest suite including a bedroom and a large bathroom that has plenty of storage space and access to the upstairs deck. The brick walkway, formerly used as parking, meanders around one side of the house and on the other side is a ramp which is one aspect of the full accessibility of the first floor of this home. The location on the corner of Frances and Stump Lane is ideal, tree lined and surrounded by beautiful homes. Features and amenities include Smart Home technology with cameras and thermostat, Rain Barrel water collection system, Azek and wood decking. This home is designated in the X zone and has been lovingly maintained. It will please the most discerning buyers.

Nestled on one of the most coveted blocks in Key West, this exceptional property in the Historic District is brimming with character and untapped potential. Currently configured as four distinct apartments - (A) 2BR/1BA, (B) 2BR/2BA, (C) Studio/1BA, and (D) 1BR/1BA - totaling 2,671 sq. ft., each unit features its own private outdoor space, a well-appointed kitchen, ample storage, and high ceilings that enhance the homes historic charm. Steeped in history, the home showcases classic Dade County pine walls, intricate crown molding, original spindles, and timeless Key West architecture. While not currently producing as a high-income property due to its setup for professional housing, it presents an incredible investment opportunity with the right vision. Whether reimagined as a high-yield rental, transformed into a grand single-family residence, or curated as a private compound, the possibilities are endless. With top-rated restaurants, vibrant amenities, and beaches just a stroll or bike ride away, this address delivers the quintessential Key West lifestyle - where history, elegance, and opportunity intersect. Seize this moment. The best of Key West awaits.

Nestled in the heart of Key Wests Historic Seaport District, this outstanding two-story residence is a true architectural gem. Tucked away on a tranquil lane with coveted off-street parking, the homes origins date back to the 1850s, showcasing timeless craftsmanship with stunning historic details, including rich Dade County Pine walls and flooring. Designed with both elegance and functionality in mind, the thoughtfully curated layout boasts a beautifully appointed kitchen that seamlessly flows into a vaulted living and dining area. A striking wall of French doors bathes the space in natural light and opens onto a spacious, newly renovated composite deck and covered porch--an idyllic setting overlooking the lushly landscaped pool area. The sparkling 23-foot heated saltwater pool, complete with a tranquil waterfall feature and swim jets, is the ultimate private oasis. Enhancing the outdoor experience, a wet bar and outdoor shower provide both luxury and convenience. The kitchen is equally impressive, featuring sleek stainless-steel appliances, gleaming granite countertops, and a built-in wine cooler--perfect for entertaining. The main level offers a well-appointed bedroom and a stylish full bathroom with a deep soaking tub and exquisite Brazilian slate flooring. A versatile den on this floor provides the flexibility to serve as an additional sleeping area, making it ideal for vacation rentals or accommodating guests. Upstairs, the primary suite is a private sanctuary, encompassing the entire second floor. This serene retreat features two generously sized closets and a beautifully designed en-suite bathroom adorned with Brazilian slate finishes. Recent updates include new AC systems and an energy-efficient on-demand water heater. For added peace of mind, storm shutters protect all windows and doors. Offering a rare blend of historic charm and modern luxuries, this exceptional Key West home is a true island treasure.

Welcome to 710 Ashe Street, a masterfully restored 1889 Eyebrow home, where historic charm and contemporary comfort converge in one of Key Wests most sought-after locations. This exceptional property, complete with a detached guest house, offers a versatile and elegant living experience--perfect for families, in-laws, or lucrative rental opportunities (rental figures available upon request). The main residence boasts three bedrooms, two bathrooms, and 1,282 square feet of refined living space. Step onto the inviting front porch, where classic island colors set the stage for the warmth and sophistication within. Inside, original hardwood floors, soaring 9-foot ceilings, and a beautifully preserved staircase pay homage to the homes rich history, while modern enhancements seamlessly elevate the experience. A thoughtfully designed brand-new gourmet kitchen showcases Cafe appliances, custom cabinetry, and French doors that open to a private backyard retreat--perfect for alfresco dining, relaxing in the lounge area, or unwinding in the spa after a day of island adventures. Upstairs, two additional bedrooms share a beautifully appointed bathroom that blends timeless elegance with contemporary finishes. Tucked behind the main home, the renovated guest house offers two bedrooms, one bathroom, and 1,021 square feet under roof. Accessible via a private walkway, this stunning retreat features an open-concept layout, where a stylish kitchen, sunlit living space, and designer finishes create an inviting atmosphere for guests or potential rental income. Located on one of Old Towns most exclusive and picturesque blocks, this remarkable property places you just moments from Key Wests finest dining, boutique shopping, and historic landmarks. Whether you seek a serene island escape or a savvy investment opportunity, 710 Ashe Street is a rare find in paradise.

This exceptional home in the most desirable of Old Town locations is now on the market for the first time in over 40 years. Nestled at the very end of hidden Lowes Lane youll find, in addition to complete peace, tranquility and privacy, an immaculately maintained and renovated 3 bedroom and 3 bath historic Conch home with original Dade County pine, heated salt water pool, off street parking under a covered carport with room for other vehicles, bikes or scooters, and immaculate grounds designed for low maintenance. There is a separate storage shed, and additional storage above the carport. A well designed renovated kitchen with pass-through to the back deck is an invitation for outdoor al fresco dining enjoyment. There are 3 renovated full baths, with one conveniently adjacent to the pool. The primary bedroom is upstairs with an en-suite bath. 2 additional bedrooms are downstairs, creating privacy for owner and guests. One bedroom has been purposed as a comfortable tv room with built-ins.

New lower price! Gorgeous move in ready, 2,205 sq ft conch style home, where historic charm seamlessly blends with modern luxury situated in the best location in Old Town. Just steps from Duval St and one block from the ocean, beach and the Southernmost Point. Priced at $2,600,000 this exquisite property offers a turn- key experience that includes a fully furnished house, in addition with a Jeep Unlimited, making it easy to navigate the island and experience all that Key West has to offer. The ground floor has an inviting open floor plan with plenty of natural light filled rooms wrapped in Dade County pine and glorious flooring that allows for seamless flow between the living spaces, perfect for entertaining guests or simply unwinding after a day of adventure. With high ceilings and top-of-the-line finishes, every detail has been carefully curated to create a space the exudes elegance and comfort. The gourmet kitchen is a chefs dream with high end appliances generous countertops and custom cabinetry. Relax outside in the heated kidney shaped swimming pool surrounded by lush tropical landscaping or enjoy the covered pergola great for dining or shade. The 2nd floor has two double sized bedrooms with a spacious balcony with a glimpse of the ocean and Southernmost House. There is also a marvelous grand foyer with space for a small office. The 3rd floor master suite offers ultimate privacy encompassing the entire third floor which has a huge walk in closet with built in dressers drawers with quartz counters and lots of storage. The lavish master bathroom has a spa shower with a luxury rainfall shower head system. Double marble sink vanities, Vintage reclaimed wood walls and luxury vinyl flooring. While preserving its historic character, this home has been thoughtfully updated with modern amenities. Dont miss this opportunity to own a historic residence in Key Wests highly sought after neighborhood. Call today for your private showing

Experience timeless elegance & modern luxury in this stunning Old Town Key West residence, built in 1866 & perched atop prestigious Solares Hill. Meticulously renovated, this historic gem blends rich heritage with contemporary comforts.Step into the foyer at the corner of Southard & Love, where preserved architectural details meet modern sophistication. Dade County pine adds authentic charm throughout, complementing the open-concept living & dining areas. High ceilings, natural light, & original hardwood floors enhance the seamless blend of old & new.The gourmet kitchen features top-of-the-line appliances, custom cabinetry, and quartz countertops, perfect for both casual meals & entertaining. The spacious island connects the kitchen to the living areas, creating a cohesive flow.This home offers four bedrooms, three with their own ensuite bathrooms. The main floor primary bedroom is a luxurious retreat with a spa-like bathroom, walk-in closet, & French doors offering serene island views. An additional main floor ensuite bedroom provides comfort for family or guests.The alternate primary bedroom retreat on the second floor with walk-in closet, vaulted ceiling & new ensuite bathroom boasts Dade County pine, an office or sitting area with a surround of French doors. Escape from it all on the second story hammock porch where a perfect breeze anxiously awaits. A third level bedroom completes this 3-story conch revival home.Outside, enjoy a private tropical paradise with lush tropical landscaping, sunlit multi-level deck, & a refreshing, heated & jetted cocktail dipping pool. The rare off-street parking spot adds convenience in this prime Old Town location.Renovated with care, the home features modern amenities like a state-of-the-art HVAC system and energy-efficient updates, ensuring comfort and style. Steps from Old Towns vibrant culture, dining, and entertainment.Owner is a licensed real estate agent in Florida & the listing agent.

High Performing Monthly Vacation Rental Property! Gross Annual income for 2024 exceeded $110,000. 1017 Angela Street is a beautifully restored 3 bedroom, 3.5 bathroom home with a vibrant personality, nestled on one of the quietest streets in Old Town, just steps from Duval Street and the Historic Seaport. Over $350,000 in recent improvements, including newly remodeled first floor bathroom, new pool heater and pump, new hot water heater, new rear composite decking system, expanded dining room with impact rated French doors, new mini split AC units, and all new landscaping. Enjoy the convenience of modern amenities that this home offers, alongside playful, eclectic touches throughout. Relax and unwind in the private backyard oasis shaded by majestic mango trees, and featuring a heated pool and jacuzzi spa. The entire property is fenced and surrounded by lush tropical landscaping. Additional benefits include first floor primary bedroom, off-street parking in the driveway, and an outdoor shower. Home was tented for termites in 2022. This is Key West living at its finest!

Traditional key West home impeccably maintained, boasts three bedrooms, three full baths with plenty of closets throughout the home. Large private lot with a heated pool featuring a waterfall. Nice size cabana room that has a/c and heat with ample closet space can be a fourth bedroom. This home has large rooms for entertaining, quaint front porch and off street parking. A true treasure.

Discover your dream home at the prestigious Truman Annex Community, situated on the serene Admirals Lane. This two-story detached single-family residence offers a perfect blend of comfort and elegance with 3 bedrooms and 3 full bathrooms. Enhanced by impact windows and doors, the house also features a private carport for added convenience. Adjacent to the property lies a shared community pool, ideal for relaxation and enjoyment. Inside, the main living area boasts exquisite travertine floors, creating a luxurious ambiance. Open the French doors to the composite wood back deck, where outdoor dining, barbecues, and lounging become a daily indulgence. The fully equipped kitchen is a culinary haven, catering to every chefs desires. With one bedroom on the first floor and two bedrooms on the second floor, each with a private bathroom, this home is designed for utmost comfort and privacy. Emphasizing its prime location, this property is just a stones throw from Duval Street, the Key West White House, and the Key West Harbor, all while being nestled within the security of a gated community. Live out your Key West dreams in this exceptional property that epitomizes the essence of island living.

Tucked away on a quiet lane in the heart of Old Town Key West, this one-of-a-kind compound blends island charm and character. Offering three distinct dwellings wrapped around a serene brick courtyard and heated cocktail pool, this property is a rare gem providing ultimate privacy while just steps from world-class dining, shopping, and entertainment.The main house is a light-filled updated 2-bedroom, 2-bath home featuring vaulted ceilings, hardwood floors, and French doors that open onto spacious porches. The open-concept living space flows effortlessly into a sleek kitchen with quartz countertops, stainless steel appliances, and an island with seating perfect for gathering with friends. The primary suite includes an en-suite bath and an outdoor shower tucked away for a private island experience. The second bedroom opens directly to the courtyard, offering a tranquil escape just steps from the pool.A detached 1-bedroom, 1-bath guest cottage provides secluded privacy for visitors or a lucrative rental opportunity. The third structure, set amongst the tropical landscaping, is a flexible bonus space ideal as an art studio, office, or additional sleeping quarters.Surrounded by lush, mature landscaping and brick pathways, the private courtyard creates a peaceful hideaway, perfect for al fresco dining or a dip in the heated cocktail pool. With off-street parking, a whole-house generator, and a fully fenced perimeter, this property checks every box for island living at its finest.Moments from Key Wests vibrant restaurants, galleries, and historic landmarks, these cozy cottages offer a welcoming slice of paradise in one of the most sought-after areas of Key West.Schedule your private tour today and make this hidden paradise your own.

High style in a highly desirable location. Amidst the quaint lanes and the best restaurants on the island you will find this completely renovated, incredibly designed and decorated 1,620 square foot, three bedroom and three and one-half bathroom delightful Conch home. In arguably the best location in Old Town you are close enough to walk or bike to everywhere you want to go yet tucked away behind your white picket fence and in your own private sanctuary. The property is being sold turnkey-the renovations have been done, the furniture has been purchased and the closets are ready for your clothes! Finished in 2020 the home was completely rebuilt including the foundation and roof. A gorgeous pool with waterfall, impact windows, impact doors, air conditioning, Plantation shutters, Dade county pine, frosted interior doors and more were added. This thoughtfully restored home has a guest room with bath ensuite on the main living level as well as another bedroom/den/office and full bath in the hallway. The kitchen, dining and great room have a vaulted ceiling and open to a covered outdoor patio with dining area, heated pool, and the perfect place to lounge. Up the floating staircase you will find the primary bedroom with bath en-suite as well as an additional bonus space that can be used as an office, gym, or overflow sleeping quarters. There is also a laundry room with a half bath. You will love the generous rooms with vaulted ceilings, open kitchen with designer cabinets, stainless steel appliances, tile flooring, and Impact disappearing glass doors that bring the outside in. At the rear of the property on Griffin Lane is an area for parking a golf cart and bicycles. When you are not cooking in your gourmet kitchen you have Cafe Sole, Five Brothers, Bobs on Margaret, Azur, Mangia Mangia, and Date and Thyme right outside your door. As a full-time residence, vacation getaway, or investment property this one really does tick all the boxes.

Introducing this beautifully renovated Eyebrow home, Winner of the Ceramic Star Award from the Historic FL Keys Foundation. An Old Town treasure that carries an inviting ambiance, instantly making you feel at ease. Lush landscaping and exterior lighting enhance the homes charming exterior. Step inside the foyer, where youll find the library on your right - A private and adaptable space with pocket doors, which could make for a productive office or an additional bedroom. To the left, the primary suite offers a walk-in closet and en-suite bath. Down the hall, youll find an additional full bath, a laundry room, and an open-concept living area that flows into a thoughtfully curated kitchen with high-end finishes - Six-burner propane stove, an expansive island, custom cabinetry (including glass-front accent lighting), a separate pantry, and french doors and pass-through windows that make for airy indoor-outdoor living. Upstairs, two guest bedrooms share a naturally lit bathroom. The expansive outdoor area features two levels--an upper terrace with a sitting area and dining space, and a lower level surrounding the pool, complete with a pool bath. Additional highlights include two off-street parking spaces with access from Canfield Lane and a whole-house generator.

Exquisite Key West Retreat in Truman Annex! Experience the best of Key West with this luxurious retreat in the exclusive gated community of Truman Annex. This Caribbean and British Colonial-inspired home blends sophistication and comfort, making it ideal as an upscale vacation home or investment with rental potential. The transient license allows weekly rentals. The residence spans three levels with 4 bedrooms, 3.5 baths, and high-end features, offering an oasis of elegance in the heart of Key WestStep inside and be in awe with the light-filled open floor plan where tall ceilings and plantation shutters highlight the living, dining and updated kitchen with quartz countertops, a breakfast bar, and premium finishes. The dining area features a stunning shell chandelier, and French doors open to a private back patio with lush landscaping, perfect for entertaining or unwinding under the stars. On the second floor, the primary suite exudes luxury with reeded wallpaper, seagrass wall-to-wall carpet, and a spa-like ensuite bath with gold fixtures, double vanities, and abundant natural light. A 2nd bedroom offers style and comfort, with a picturesque window in the separate bath. A stacked washer and dryer are located on the 2nd floor. The upper level provides privacy for guests with two additional bedrooms and a full shared bath. Throughout, the home showcases coastal sophistication with wood plank vinyl flooring, seagrass carpet in the bedrooms, reeded colonial-style wallpaper, and tasteful touches like gold bathroom fixtures and glass shower doors, embodying refined Key West charm. Enjoy a shared community pool, assigned covered parking, and walkable access to Duval Street, Mallory Squares sunset celebrations, Fort Zachary Taylor State Park, and Truman Waterfront Park. Whether a personal retreat or a smart investment, this property combines historic allure with modern luxury, providing an unparalleled Key West lifestyle. Video tour https://tinyurl.com/102-Admirals

Old Town Villas at Key West is a luxurious gated development just 1 block off of Duval Street. This townhome has 3 bedrooms, 3.5 baths on 4 floors. A private elevator in each unit takes you from the 2 car garage to the rooftop terrace. Just under 2,700 SF of solid concrete construction accompanied with high end appliances, a large community pool & cabana area.

Impeccably preserved historic residence located in the heart of Old Town Key West. Discover the enticing charm of Key West and stroll through the majestic tree lined streets from 715 Frances Street. A rare combination of Key West luxury and historic architecture, this beautiful eyebrow home is perfectly positioned on a large spacious lot on sought after X Flood zone keeping you high and dry.Three beautifully appointed bedrooms, all ensuite upgraded bathrooms with a master on the ground floor and two bedrooms on second Floor.Recently completed 360 sq. ft. gazebo completes the property adding a stunning entertainers dream with outdoor kitchen, dining and seating area overlooking large saltwater pool, jacuzzi, and private garden.Gourmet kitchen finished with custom cabinetry, large countertops, gas Viking stove, Subzero appliances and glass chandeliers.Property is being sold turn key and is beautifully appointed with a stunning designer furniture package and interior plantation shutters.Additional features include full house generator, outdoor storage, off street parking for car and golf cart, outdoor shower, 2 new AC units and dehumidifier, new pool heater and chiller, new landscape lighting, new Ipe decking, Oolite stepping stones and bench, 3 new on-demand tankless hot water heaters, kevlar shutter package for entire house & 5 Camera security system.

Zen Villa represents a rare opportunity in the heart of Old Town, Key West, comprised of three homes on a spacious 5,891 SF lot. The main residence at 400 Aronovitz Lane is a luxurious 3-bedroom, 4-bathroom contemporary island estate and an active vacation rental, while 621 and 623 Whitehead Street offer two charming 1-bedroom, 1-bathroom cottages, currently rented long-term.The main home redefines island elegance, welcoming you with an airy lounge boasting 18-foot cathedral ceilings, a chic wet bar with granite countertops, a beverage cooler, and an ice maker. The open-concept living and dining areas flow effortlessly into multiple outdoor spaces, creating the ultimate indoor-outdoor lifestyle. Expansive sliding glass doors open to a tropical poolside oasis designed by Craig Reynolds, featuring a heated pool with a tranquil water feature, lush landscaping, ambient lighting, and a refreshing outdoor shower.The first-floor primary suite is a serene retreat with a spa-like bathroom, marble finishes, and a steam shower. The chefs kitchen is a showstopper, equipped with a large granite island, Sub-Zero and Thermador appliances, and custom lighting. Upstairs, the second primary suite opens to a private covered porch with an outdoor shower. A cozy guest bedroom with a soaking tub provides direct access to a covered patio.Zoned Historic Residential Office (HRO) with an ADA-compliant entrance, this flexible property offers endless possibilities for live-work or investment use. Just steps from Duval Street, Truman Waterfront Park, and Fort Zachary Taylor Beach, the property is located in the coveted X-Flood Zone and features 3+ off-street parking spaces. Dont miss the chance to own a piece of paradise--schedule your private tour today!

Situated directly across from the iconic Ernest Hemingway House, this exceptional family compound combines the rich history of Old Town Key West with modern luxury and island charm. From the famous six-toed cats that roam next door to the vibrant energy of Duval Street just steps away, this location is as legendary as it is convenient. Spanning two addresses at 407 and 415 Olivia Street, this versatile property is situated in the X flood zone and offers four off-street parking spaces. The main house, a meticulously renovated mid-century modern gem, welcomes you with a grand entrance foyer that flows into a spacious living, dining, and media area. Perfect for entertaining, the space features a working fireplace and a 76-inch TV. The gourmet kitchen boasts solid wood cabinetry, Bosch and Thermador appliances, an induction cooktop, column fridge/freezer, wine cooler, and an impressive 13-foot quartz waterfall island. Impact sliding doors open to a stunning saltwater pool complete with a sun ledge, slide, and waterfall. Surrounded by tropical landscaping, this backyard oasis also features an outdoor shower, fully equipped kitchen, and plenty of space for entertaining. The main house offers four bedrooms, each with generous closet space and outdoor access. The primary bedroom includes a new custom walk-in closet with solid maple built-ins. Another ensuite bedroom has been transformed into a stylish home office with a built-in Murphy bed. The two additional bedrooms share an elegant bathroom featuring a luxurious soaking tub and shower. Adjacent to the main house is a charming two bedroom, two bath Conch-style cottage that provides the perfect guest retreat or mother-in-law suite. This home features a fully equipped kitchen, Dade County pine accent walls, and a tranquil outdoor space to relax under the shade of swaying palm trees. Dont miss the chance to see this unique compound that provides the perfect blend of history, luxury, and the ultimate Key West lifestyle!!

Investment opportunity! Weekly rentals are allowed! Nestled within the highly sought-after Truman Annex in Old Town Key West, 202 Admirals Lane exudes coastal charm and luxury living at its finest. Boasting 5 bedrooms and 4 full bathrooms, this meticulously maintained residence showcases beautifully renovated bathrooms and a private pool oasis, offering an idyllic retreat for residents and vacationers alike. Situated nearby the iconic Duval Street and the tranquil expanse of Fort Zachary Taylor State Park, this home epitomizes the quintessential Key West lifestyle. Upon entering, youre greeted by an inviting main living area, adorned with French doors that effortlessly blur the lines between indoor and outdoor living. A sun-drenched sunroom, encased in glass doors, is the perfect setting for relaxation or entertainment year-round. Additional living spaces abound, including a bright and airy sitting room. The main floor is thoughtfully appointed with a convenient full bathroom, ensuring comfort and convenience for guests. The 2nd level offers 4 bedrooms and 3 full baths and the ensuite 3rd floor is great for guest . Included is a Truman Annex transient rental license allowing for weekly rentals, 202 Admirals Lane presents a lucrative investment opportunity as a successful vacation rental. Rare for Key West, this home features a coveted 2-car garage, providing secure parking and storage, a coveted amenity for sure. Offered turnkey, the residence comes complete with all furnishings and future reservations, promising a seamless transition for discerning buyers or investors seeking the ultimate Key West retreat.

Step into the enchanting world of Key West history at 709 Eaton Street, a meticulously preserved gem built circa 1847 in the iconic Seaport neighborhood. Historic charm and modern comfort, this home delivers 4 bedrooms, 4.5 baths, with 3 bedrooms, 3.5 baths conveniently located on the first level. The upstairs consists of the primary bedroom suite with an additional private study as well as a wonderful, covered porch.Discover the timeless elegance of its living room, dining room, and a fantastic den with an open kitchen floorplan complete with Viking appliances. Step outside to enjoy your covered patio, private pool, and inviting outdoor living areas surrounded by lush tropical foliage. Driveway for two cars with one covered parking space.Perfectly situated for exploring Key Wests vibrant attractions, this home offers a rare opportunity to own a piece of island history while indulging in the ultimate Key West luxury lifestyle.

Perched on the prestigious Millionaires Row and enveloped by lush tropical greenery, this extraordinary estate boasts two spectacular homes on one expansive lot, offering a rare blend of luxury and exclusivity in Old Town Key West. With six lavish ensuite bedrooms and a serene pool, this property is a true masterpiece.The main residence, meticulously restored, exudes timeless charm while seamlessly integrating modern opulence. Off-street parking for two and a newly constructed guest house elevate this homes grandeur. Upon entry, youll be greeted by an airy living space featuring rich Dade County pine walls that lead to a 12-person dining room, perfect for hosting elegant gatherings.The kitchen is a chefs delight, adorned with bespoke cabinetry, sculpted marble countertops, and state-of-the-art Sub-Zero & Wolf appliances, including a wine cooler and coffee center. Elegant French doors open to a wrap-around porch that blends indoor and outdoor living.On the main floor, a versatile ensuite bedroom can double as a welcoming den. Upstairs, three additional ensuite bedrooms offer breathtaking views of the lush foliage, each adorned with vaulted ceilings and luxurious finishes. The primary suite is a haven of comfort, featuring a retractable window, custom closets, and a lavish bath with timeless marble, dual sinks, and a walk-in shower.The guest house is a marvel of design, with soaring vaulted ceilings, exposed cross beams, and a charming sleeping loft. It includes two ensuite bedrooms, a full kitchen fitted with Miele appliances, custom tiling, and a stylish island for casual dining. Every detail, from the reclaimed river wood floors to the impact windows and doors, exudes luxury. Separating the two homes is a Craig Reynolds-designed tropical paradise, complete with a saline pool and cascading waterfall. The outdoor space is thoughtfully finished with an outdoor shower and private half bath. 1109 Fleming Street is the epitome of refined island living.

With its special transient license, The Royal Compound is currently generating $500,000 a year from first-class guests who will accept only the best in vacation homes. Whats 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!

Nestled in the heart of Key Wests historic district, 616 Eaton Street is a testament to quality, timeless beauty, and refined living. This single-family residence was constructed in 1911 and painstakingly renovated and reimagined over the last few years culminating in 2024 with the spectacular like new home. Most hidden from the Street, it exudes classic Key West architecture blended with modern elegant designs. With 5 bedrooms, 5 full baths & 2 half baths, the home spans 4,000sf on a large 12,478sf lot. The 2-story primary home contains the living room, dining room, kitchen, 2 office spaces/dens, one of which could be a bedroom if desired, 2 half baths on the living level & a spectacular 2nd floor primary suite with office/ laundry & an enormous outside covered deck for private lounging. Thoughtful renovations include a stunning glass wall that opens between the outdoor dining pavilion & the top of the line kitchen w/ functional pass-through windows from the kitchen to the pool area. Reclaimed hardwood floors & tall ceilings ensure a perfect balance of historical character & contemporary functionality. The substantial living area, accented by natural light, offers a warm & inviting atmosphere & the gorgeous central pool w/ a water feature creates a stunning outdoor oasis & is perfect for entertaining. Surrounding the pool & outdoor dining pavilion are 2 phenomenal guest houses, housing a total of 4BD/4BA plus a full 1,512sf attic w/ staircase that is built for storage. Lots of off-street parking is offered along w/ a carport & small garage. Everything is new, from the hard wood floors & bathrooms to the salt generated heated pool & generator. This property is a rare offering that combines historical significance, luxurious living & an unbeatable location in one of Key Wests most coveted neighborhoods. Located in the X flood zone just 2 blocks from both Duval St. & the Historic Seaport, it is walkable to all the wonderful restaurants, galleries & shops.