This charming two-story Old Town cottage in Key West is ideally located just a half block off of Duval Street. The interior was beautifully renovated throughout with new floors, updated kitchen and impact windows & doors. The first floor includes a master bedroom with French doors leading out to an in-ground swimming pool. Upstairs, a loft provides a spacious guest bedroom. Overlooking the large pool and guest cottage which features vaulted ceilings and tiled flooring. A spacious wood deck covered by a large tiki hut connects the main house and guest cottage, creating a seamless indoor-outdoor living experience.The private pool, surrounded by lush landscaping, offers a tranquil retreat characteristic of Key West living. Additional amenities include an outdoor shower and covered off-street parking.

A Historic Masterpiece originally built prior to 1912 and completely updated to the highest quality in the legendary Meadows neighborhood of Key West. 1317 Olivia Street is a two-story designer home perfectly paired with exotic tropical landscaping, custom swimming pool and water feature, IPE Brazilian hardwood decking, and sophisticated outdoor shower. The spacious master bedroom offers privacy and comfort, complete with a walk-in closet and custom built-in dresser. At the heart of the home, the chefs kitchen features a natural quartzite island with a waterfall edge flowing effortlessly into the open dining and living area with hardwood floors throughout. Here youll find 12 foot saw-tooth vaulted ceilings and low hung floating cabinetry along the entire western wall, creating a striking visual anchor for the room. A full bathroom is conveniently located off the kitchen, adding ease for guests. The living space extends to a dramatic wall of accordion-style impact sliding doors, opening to the saltwater pool and lush gardens that softly illuminate at dusk. Thoughtfully designed outdoor areas include sunbathing spaces, outdoor dining, and multiple seating areas, making it an ideal island retreat. With off-street parking, an X-Flood zone location, a whole house generator, and a minimalist yet impeccable design, this home is a unique opportunity to experience the Key West lifestyle with privacy and elegance in one of its most desirable neighborhoods.

1212 Watson Street, aka Island Bliss, is a quintessential Old Town Key West home. This beautiful one-and-a-half-story home has been thoughtfully restored with a mix of modern touches and traditional Key West influences. From the stylish LVT flooring throughout to the stunning kitchen to the new mini split ACs, theres isnt a bit of this home that hasnt been updated. The primary suite occupies the entire second floor, with a spacious bathroom and closet, as well as direct access to the rooftop deck. The two guest bedrooms are located on the first floor and share a full bathroom. The outdoor space is just as impressive, featuring a saltwater heated pool, outdoor kitchen and grill, AZEK decking on the patio and on the upstairs sun deck, and turf yard. And dont forget about the outdoor shower, a Key West staple! Situated on one of the quieter blocks in Old Town, Island Bliss gives you the feeling of being away from it all yet is only a short stroll from everything that Old Town has to offer. The charming front porch with classic gingerbread is the perfect place to relax in the island sun and an off-street parking spot is waiting for you in the driveway.

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.

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!

Beautiful 3 bedroom 2.5 bath home being offered Turn-key, perfect walking location to restaurants, historic waterfront, shopping and all the nightlife on Duval St . Spacious open floor plan for easy living and entertaining friends and family includes the ever important first floor bedroom, half bath and laundry room. Just off the kitchen/ dining area sneak out to the hot tub to relax, or outdoor patio for dining with plenty of shade and privacy. Back inside, make your way up the gorgeous staircase to the second level to find an oversized master bedroom with walk in closet and ensuite bath. The second floor also includes the third bedroom and second full bathroom! 400 White St is a home you wont want to leave ! Call today to schedule your private tour.

Discover the essence of island living in this expansive 3,197sf, 6-bedroom, 3-bathroom home, perfectly positioned on a generous 9,500sf corner lot in the heart of Key West. This spacious 2 story CBS home features a gourmet kitchen, tile floors, 2 laundry areas, sundeck & a new roof. The sprawling yard, enclosed by a privacy wall, offers plenty of room for boat and trailer storage, RV parking, and a safe play area for kids and pets. An in-ground concrete pool with water feature adds to the outdoor appeal, while a storage shed provides extra convenience. Offering a rare combination of convenience and space, this residence is ideally located minutes from schools & grocery stores, while also being near the new Happy Landings Marina and the Key West Yacht Club, making boating a breeze! With a flexible layout and ample space, this property is brimming with possibilities, ready to be tailored to your vision of the perfect island retreat.

3731 Eagle Avenue is an exceptionally crafted two-story masterpiece on one of Key Wests most sought-after blocks in New Town. Built by a locally renowned contractor for their personal family home, this property stands out for its superior quality and attention to detail featuring pressure treated pine framing, hardie board siding, and double insulated windows. A grand tropical entrance reveals a secluded oasis complete with mature native landscaping surrounding a custom heated swimming pool, water feature, two outdoor showers, covered outdoor grill, and beautifully maintained IPE decking. Nestled at the rear of the property and elevated well above ground level, the home enjoys both privacy and stunning tropical views. The first floor boasts a spacious, open layout featuring a large living room with custom-built cabinetry, a formal dining area, and a gourmet kitchen fitted with elegant Poggenpohl cabinetry. Two guest bedrooms and two guest bathrooms complete this level, offering ample space for family or visitors. Upstairs, the primary bedroom offers a large covered porch overlooking the pool and gardens, walk in closet, and beautiful en suite bathroom. Additional features include covered parking with an electric impact rated garage door and exquisite design details throughout, making this tropical hideaway a rare find on one of the best blocks in Key West.

Magical in the Meadows! An exceptional opportunity to own this charming Conch cottage, originally built in 1892 and meticulously renovated to preserve its historic character while offering modern comforts.Currently configured as two bedrooms plus a versatile office/third bedroom and two bathrooms, this beautifully maintained home is nestled in a highly sought-after, quiet, and friendly neighborhood--just moments from everything Key West has to offer.This quintessential property showcases exquisite craftsmanship, including custom built-ins, crown molding, and trim handcrafted by a master shipbuilder. Architectural highlights include soaring ceilings, stunning Dade County Pine throughout, custom skylights. For exterior enhancements, welcoming front porch, privacy fencing, plus copper gutters and elegant outdoor lighting. The fully fenced property has been recently painted, enhancing its pristine curb appeal.Step into your private backyard oasis, where Ipe wood decking surrounds a sparkling pool with a brand-new heater and chiller. An outdoor shower completes the experience, perfect for embracing the laid-back luxury of island living.This one-of-a-kind home embodies the epitome of Key West charm and style--dont miss your chance to make it yours and enjoy the ultimate in Key West living!

Experience the epitome of Key West living in this exquisitely renovated 2-bedroom, single family home nestled within the exclusive gated community of Truman Annex. The first floor of this beautifully renovated Coastal designed home features a gourmet kitchen with top-of-the-line appliances, a spacious sun-filled Living Room and Dining Room made for hosting unforgettable gatherings. The private back patio offers outdoor entertaining space for dining, grilling, and soaking up the sun. Both elegantly appointed bedrooms are located on the second floor, each with their own dedicated bathroom. A truly unique feature of this home is the elevator, allowing for easy access and transport to the second floor. The prime location of this home makes it easy to take a quick Stroll to all that Key West has to offer - the nearby Truman Waterfront Park, first-class restaurants, art galleries, shopping, and the lively music scene. Additional benefits include one designated parking space, access to the community pool, a private outdoor shower, Impact Resistant Windows & Doors, and weekly transient rental license. Being offered turn-key, this home is ready to move right in and enjoy your slice of paradise!

Essentially a Brand-New Home at an Unbeatable Price Per Square Foot!Nestled in the coveted X flood zone, this historic Key West gem has been completely reimagined from the inside out. With all-new plumbing, electrical, roof, and impact-resistant windows, this property offers the charm of the past with the peace of mind of modern construction.Step beyond the charming Caribbean gate and into a private oasis designed for relaxation. Inside, a modern organic aesthetic blends effortlessly with coastal elegance. The original Dade County pine exposed beam ceiling adds warmth and character, while a natural palette of recycled glass lighting, oak floors, Calacatta marble baths, and European quartz countertops creates a serene, upscale ambiance.Perfect for intimate gatherings, the spacious kitchen bar overlooks a heated and chilled Zen pool with a tranquil waterfall feature. The entertainment space transitions seamlessly to an expansive patio framed by lush greenery, including a mature Ruby Red mango tree--a true tropical retreat.Designed for comfort and privacy, the oversized first-floor primary suite is a luxurious escape with a spa-like bath. Upstairs, two guest bedrooms feature ensuite baths, while a main-floor half bath adds convenience. The home also offers ample storage and dedicated office space for two desktops.With a monthly rental license, this property is an ideal investment or vacation retreat, positioned just moments from Key Wests top attractions. Parking is available right out front.Schedule your private showing today to fully appreciate the exceptional details and craftsmanship that make this home truly one of a kind.

Experience luxury living in this meticulously renovated historic residence nestled within the prestigious gated community of Grinell Gardens. Boasting all-new impact windows and doors, hardy board siding, and a new metal roof, this home exudes charm and durability. Delight in the serenity of two private side yards adorned with vibrant landscaping, creating a tranquil outdoor oasis. Inside, three spacious bedrooms each paired with a full bath offer a harmonious blend of comfort and elegance. Embrace the perfect fusion of historic appeal and modern convenience in this inviting and carefully crafted home. Enjoy convenient off-street parking and seamless access to the vibrant amenities of Old Town Key West. This prime location offers an array of bars and restaurants just a leisurely walk away, as well as nearby beaches for added leisure and relaxation.

Experience the charm of Old Town living at 923 Eaton St, a beautifully updated historic home featuring three bedrooms and two full bathrooms, ideally situated just steps from the Historic Seaport and a short stroll to Duval Street. Offered turn-key, this property combines classic Key West architecture with modern enhancements, making it perfect for enjoying the local lifestyle.Inside, youll find Dade County Pine walls, hardwood floors, and renovated kitchen and bathrooms. The second floor boasts two inviting bedrooms, while the first floor offers a charming bunk room. Step outside to discover a spacious 10x20 ft heated saltwater pool and a private tropical backyard oasis, perfect for outdoor relaxation. Additional features include a newer metal roof, an impact-rated sliding glass door leading to the rear deck, and efficient ductless AC units.This charming home is fully furnished and ready for you to move right in or to generate a reliable income as an investment property, allowing you to enjoy all that Key West living has to offer!

This property has been updated with two bedrooms and two full bath on the second floor. The first floor is an open floorplan with kitchen and breakfast bar, dining and living area. There is a guest cottage with bath overlooking the pool.

Welcome to this charming home, nestled in the highly sought after, Historic, Meadows neighborhood in Key West. It features 3 bedrooms, 2 full baths and one 1/2 bath. Relax or entertain in the open floor plan living area. 2 sets of french doors flow seamlessly to the wraparound porch, pool and guest cottage/studio. Access to the 1/2 bath from the back porch and guest cottage make spending time in the tropical pool area a pleasure. Dade county pine and a stunning cathedral ceiling add to the spacious and historic ambiance. The spiral staircase brings you to the 3rd bedroom and den/music room. The primary bath is beautifully updated. This home has been meticulously maintained to retain the historic ambiance. For your convenience this home offers off street parking for one vehicle. Flood ins. $795 Homeowners $3,310.95 Easy to show.

Welcome to this captivating historic Conch home, where the essence of Key West island luxury comes alive. This charming residence boasts a classic front porch that beckons you to sit back and enjoy the tropical breeze, making it an ideal space for leisurely mornings or cozy evenings. Upon entering, you are greeted by a sun-drenched interior adorned with exotic hardwood flooring and soaring high ceilings that create an inviting and spacious atmosphere, perfect for both relaxation and entertaining.The heart of this home lies in its kitchen, a culinary haven equipped with stainless steel appliances, ample pantry space, and a comfortable seating area. The open design allows for seamless flow from the kitchen to the back patio, making it effortless to host gatherings or enjoy quiet family meals. Step outside to discover a relaxing pool area, complete with an air-conditioned poolside guest cabana. This versatile space features a wet bar and a cozy seating area that easily transforms into a pull-out sofa bed, ideal for hosting friends and family or enjoying a peaceful afternoon by the pool. Ascend to the second floor to find a striking stained glass window that adds a touch of elegance to your arrival. Here, youll discover a generous master suite, boasting cathedral ceilings and an abundance of closet space, creating a serene retreat. Additionally, a bonus room is currently set up as a home office, providing flexibility for your lifestyle needs. A delightful guest bedroom completes this level, featuring access to a private rooftop terrace that overlooks the inviting pool, perfect for unwinding at sunset or enjoying morning coffee in solitude. This historic Conch home is not just a residence; it is a lifestyle, offering a harmonious blend of modern conveniences and timeless charm. With its ideal location, you are just moments away from all that Key West has to offer--vibrant nightlife, exquisite dining, and stunning beaches.

Total renovation in the highly desirable Meadows in Old Town. Legal duplex totally restored from the ground up in 2023 & 2024. 2 bedroom/ 1 bath downstairs has 788 sf. of living area, front porch, large backyard & rear deck.Upstairs is 1 bedroom & 1 bath 544 sf. with private tree top deck. Lush, tropical landscaped 2,225 sf. lot plus bonus 5 x 74 recorded hiatus on E. side of property. Private off street Parking. Interior details: Many Dade County Pine walls inside professionally restored New Mitsubishi ductless split AC systems w/remotes.New LED surface mount ceiling lights.New luxury vinyl plank flooring w/ rubber backing for softness and quietness.All windows are new, 2 over 2, impact resistant with window treatments.Professionally designed kitchen by Rosanne has gorgeous Quartz countertops & new custom, all wood cabinets.New stainless steel LG appliances including a new Refrigerator, Electric range & Microwave, dishwasher & garbage disposal.Upstairs has new kitchen, cabinets and countertop with new stainless steel Frigidaire refrigerator, range & garbage disposal.Both bathrooms are fully tiled &have glass enclosure, walk in showers. Downstairs has duel under counter sinks with Quartz countertop. Exterior:You dont hear this often, look under this house! 30 new concrete, steel reinforced, spread footers secured into cap rock & tied to the house with double 2x 10 rim joists & 2 x 8 floor joists, all pressure treated.Also, Front Porch, side deck & stairs & rear deck all rebuilt with new footers.General Contractor was Brian McKendry.All new V-crimp roofing by A-Plus Roofing, with new plywood subroof, hurricane straps & storm safety underlayment for Max. Wind Insurance credits. All new gutters as well.Entire house, inside & out professionally painted by Perrys Painting.All new plumbing & instant hot water heaters by Robert from Gary Moes.All new electric by Check Electric$1,500/sf reno priced at $1,400/sf!

Welcome to Casa Bella Petite le Bleu., an architectural gem in the heart of Old Town Key West, honored with a prestigious Ceramic Star for historic preservation. Nestled in the desirable X-Flood Zone, this home blends timeless charm with contemporary upgrades, off street parking and a private pool making it the perfect tropical retreat. From the moment you arrive, the classic front porch invites you in. Inside, open concept living awaits, highlighted by rich Dade County Pine, a chefs kitchen featuring Viking appliances and custom cherry cabinets. Making it the perfect space to entertain as the indoors flow seamlessly into the outdoors. Double sets of french doors open up to a tropical wonderland featuring a heated pool with a tranquil water feature, surrounded by lush landscaping. The expansive deck offers a covered lounge area, outdoor dining space, outdoor shower, and a charming historic accessory structure--perfect for a small guest suite, art studio, or office.Located on the quiet end of Elizabeth Street in the sought-after Solares Hill neighborhood, one of the highest points on the island. This property is just two blocks from Duval Street and centrally located. Walking distance to Key Wests best restaurants, beaches, and galleries, all while savoring the peace of a quiet, picturesque Old Town neighborhood.Whether youre seeking a luxurious island getaway or a full-time residence with historic charm, 819 Elizabeth Street offers the best of Old Town living. Dont miss this rare opportunity to own the perfect Key West home.

Enjoy the perfect Key West location - Old Town bordering the Casa Marina neighborhood - in this 3 bedroom, 2.5 bath pool home. Youll have peace of mind knowing that the home was completely renovated from the ground up in 2019 while keeping with the historic style of the homes origins - tongue in groove ceilings, wood floors, pecky Cypress wall accent - but adding modern amenities such as impact windows, stainless steel appliances, granite countertops, tankless water heater, in-home laundry. The Main Home has an en suite Primary Bedroom; Guest Bath accessible from the hallway and Guest Bedroom; open concept Kitchen and Family Room with vaulted ceiling and a wall of accordian glass panels overlooking the pool courtyard. Opposite the pool is the Guest Cabana with Half Bath and Outdoor Shower. The property has been offered as a vacation rental and also kept part time for the owners use. Close to everything you could want in Key West - around the corner from world famous El Siboney Cuban Restaurant, 2 blocks from Truman, 4 blocks from Duval St., a quick walk to Higgs Beach and the White Street Pier. Home is being offered turnkey furnished.

Tucked away in one of Key Wests most desirable neighborhoods, this beautiful newly renovated home offers an unbeatable location, within walking and biking distance of iconic spots like White Street Pier, Bay View Park, and Higgs Beach.Originally built in 1948, this property seamlessly combines traditional Key West charm with a fresh, modern coastal design. With approximately 1,260 sq. ft. of living space, the main home features two spacious bedrooms and two bathrooms, while the mother in law detached unit provides an additional bedroom and bath, perfect for visitors or extended family.The master suite is a true retreat, featuring a stunning new ensuite bathroom with double vanities and a large walk-in closet. The living and dining areas, with their soaring 15-foot ceilings, create an open, airy atmosphere thats perfect for both everyday living and entertaining.The kitchen is a chefs dream, featuring custom cabinetry, sleek quartz countertops, and an all-new suite of appliances. Throughout the home, youll find tile flooring, central air, and a washer/dryer.Step outside to experience the homes impressive outdoor living space, designed to embrace Key Wests tropical climate. A brand-new heated salt water pool with a waterfall feature, paired with a spacious composite deck, offers plenty of room to relax or entertain family and friends. The fully fenced backyard ensures privacy and security for both you and your pets. There is off-street parking with ample space for additional vehicles.This home strikes the perfect balance between elegance and comfort, offering a rare opportunity to enjoy the best of Key West living. With its thoughtful design, exceptional location, and luxurious finishes, this property is the ideal place to call home. Dont miss your chance to make it yours!