Mile Marker 0 - 10 homes for Sale in the Florida Keys Real Estate

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.

Not a duplex! This beautiful property consists of two single family homes surrounded by tropical foliage. This one-of-a-kind compound blends island charm and character. Offering a 3 bedroom 4-bath Conch house with a large separate 1 bedroom 1 bath home with a full kitchen. The 3 bedrooms, 4 bath home has wall-to-wall Dade County pine with an open floor plan and a chefs kitchen. The open concept living space flows effortlessly into a sleek kitchen with quartz countertops, stainless steel appliances, and offers a tranquil escape just steps from the pool. The second, 1 bedroom, 1-bath home provides secluded privacy for visitors or a lucrative rental opportunity. Surrounded by lush, mature landscaping and brick pathways, the private courtyard creates a peaceful hideaway, perfect dip in the heated oversized pool. Steps from Key Wests vibrant restaurants, galleries, and historic landmark.

Beautiful Meadows Masterpiece located one of Key Wests idyllic neighborhoods. Built in 2020 using the finest materials and craftsmanship, this home combines the best of Key West Architecture with modern luxury finishes.Exquisite Nickel-grooved walls and stunning hardwood floors that create a warm and inviting atmosphere. The coffered ceilings, adorned with Dade County Pine add that extra touch of sophistication, while the impact windows and slider patio doors provide both beauty and peace of mind.The spectacular chefs kitchen is a culinary dream, showcasing quartz countertops and a premium viking appliance package. Overlooking the living and dining area, it opens up via two large pocket sliders to sun-kissed patio and heated pool and also features two electric awnings providing an element of shade.Each of the four bedrooms is en suite, with custom closets, custom Bahama shutters and stunning bathrooms, finished with luxurious marble, quartz and iridescent tile, ensuring comfort and style for everyone.Exterior package is equally impressive, featuring decorative shutters, full irrigation and lighting, mature tropical landscaping providing lots of privacy and light composite decking. Chicago brick walkway and off street parking add to the propertys charm and functionality.Located in an x-flood zone, this home was constructed using the highest level of building codes and standards with many luxurious features, resulting in an exceptional home in a beautiful neighborhood.

This is one of the very few waterfront homes in Old Town Key West that comes with a private boat slip and open water views. The house features a large living room and kitchen area and a gorgeous sunroom with floor to ceiling windows overlooking the water and leading out to a spacious deck. A private path from the deck gives access to a heated pool that is part of the HOA fees that also include use of the dock. The house comes fully furnished, PLUS includes the boat and boat trailer. The private boat slip features a custom floating boat lift and there is easy open water access from the Garrison Bight Marina for fun during the day. This Meadows house is also walking distance to Duval Street for night time dining and entertainment. Plus two private, dedicated parking spots.. A rare gem that will not last!

Welcome to The Chavez House, a beautiful 3-bedroom, 2 bath transient rental home proudly listed on the National Register of Historic Places. With a solid rental history, this property is a fantastic investment opportunity in the heart of the historic seaport neighborhood.Upon entering, youre greeted by a bright and inviting family room bathed in natural light--an ideal space for intimate conversations and gatherings. The main floor features a spacious primary en-suite bedroom with king-size accommodations, accentuated by Dade County pine walls and a thoughtfully designed bath with dual sinks, a tub/shower combination, and a separate pedestal sink room.The inviting dining area comfortably seats six and offers an option for outdoor dining on the lanai, creating an authentic island experience. The lanai, complete with a vaulted ceiling and tropical fan, serves as an excellent gathering spot for family and friends. The kitchen features a convenient breakfast bar for four, stainless steel appliances, white quartz countertops, and a vaulted shiplap-style ceiling. French doors lead to a private pool area where you can relax in the heated pool, surrounded by lush tropical landscaping.Ascend the beautiful wrap-around staircase to discover two additional queen bedrooms on the second floor, each featuring unique elements such as barn doors, vaulted ceilings, and ceiling fans. The shared bathroom includes a vanity sink and tub/shower combination, ensuring comfort for all guests.Located in vibrant Old Town, The Chavez House, is just a short stroll from the allure of Duval Street, the Key West Cemetery, and the Historic Seaport district. With its proven rental history, this Transient ensures the potential for lucrative income and offers a serene escape.Dont miss your chance to own The Chavez House--where historic charm meets modern living. Schedule your showing today!

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.

Tranquil Midtown Estate feels worlds away, while just minutes to delectable dining and nightlife in exciting Key West! Nestled on nearly a quarter-acre of gated, lush tropical gardens, this spacious 3/3 main house plus 1/1 guest house comes move-in ready; boasting elevated coastal design where modern finishes and amenities meet relaxed sophistication. Indulge in year-round temperate weather from a backyard oasis, masterfully outfitted for hosting memorable gatherings with a well-equipped outdoor kitchen with gas grill, gas burner, ample prep space and beverage cooler. Lounge poolside, cocktail in hand, in the shade of a large tiki hut and cool off in the stunning resort-style pool, complete with fountain waterfalls! Additional exterior features include brick paver pool deck and outdoor rain shower. Upon entry, the main house features an open-concept great room with walls of impact glass windows and doors, providing abundant natural light. The immaculate Chefs Kitchen, with quartz countertops, glass tile backsplash, premium stainless-steel appliances, and island with seating, allows for effortless entertaining. As a bonus, a Dutch door leads to a spacious butlers pantry with laundry. The primary suite enjoys privacy in its own wing, and comes equipped with luxurious en suite, walk-in closet, and access to a private garden. The separate guest wing offers two expansive bedrooms and two full bathrooms. The well-appointed guest house offers two floors, with living room and kitchenette on the main level, complete with serene pool views and impact glass doors leading out to a private, poolside composite deck. The upstairs guest bedroom offers loads of privacy and en suite bathroom. Enjoy an abundance of covered parking with two pergola carports and additional off-street parking. Located within a quiet, established neighborhood but in proximity to restaurants and convenience stores in town, this ideal location offers the best of both worlds!

PRICED TO SELL - This is a rare and exceptional opportunity!Land is at premium in Key West, and this expansive nearly 12,000 sq. ft. lot with not one but essentially 3 houses and room to grow, is an extraordinary find. Discover a balanced blend of Key West character, mid-century charm, and modern updates with this one-of-a-kind multi family compound. This property could not be more well designed for seclusion and private entertainment. Whether youre looking for a spacious primary residence, an income-producing property, a redevelopment opportunity, or a combination of all three, this is your drawing board.Once home to a beloved local artist, this award-winning property--recognized by the Old Island Restoration Foundation--is a nostalgic tribute to its time period. The current owner has preserved and enhanced its retro artistic flair, creating a truly unique ambiance that transports you back in time.Property Highlights:✅ Three Separate units- Each with its own private access and gated tropical yard✅ Main House (4 BD | 3.5 BA) - An open combo entertainment area overlooks a resort-style outdoor space featuring a stunning collection of mature and rare plant species, creating a lush, tropical sanctuary. At its heart, a luxurious heated pool basks in the sunshine by day and transforms into a glowing oasis by night, illuminated by soft ambient lighting.✅ Second Unit (3 BD | 2 BA) - Exposed beam ceilings, skylights, and a serene outdoor shower.✅ Third Unit (2 BD | 2 BA) - A cozy retreat with an expansive patio space✅ Concrete Block Construction, Impact windows and doors for added security✅ Off-Street Parking & Endless Storage - A rare convenience in Key West✅ Only three blocks from the beach/pier and a short stroll to Old Town. This property is an entertainers dream that must be seen in person to truly understand and appreciate all it has to offer.

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.

Vacation rental Ocean and Harbor view unit in Truman Annex. Beautiful sunset vistas of the Atlantic and the Gulf while also overlooking the the tropical and lush grounds of Truman Waterfront Park and Truman Harbor. This residence features a large covered balcony right off the main living area with living room, dining room and kitchen. The second storys primary bedroom and bath opens out to its own private balcony. Highly desirable Old Town location in Mills Place condominiums in Truman Annex.

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.

Experience the true essence of Tropical living in Key West with this exquisite mid-century estate, the perfect blend of a private sanctuary and a highly coveted transient license, making it a lucrative income-producing asset. Located on an expansive corner lot, this property is enveloped by lush foliage, ensuring the utmost privacy and a serene ambiance that feels worlds away yet remains just moments from the vibrant heart of Key West. As you enter through the winding brick pathways, you are greeted by mature landscaped gardens and multiple outdoor spaces designed for both relaxation and entertaining. The heart of this oasis is a stunning 35-foot heated pool accompanied by a covered pavilion, offering the ideal setting for leisurely afternoons or elegant gatherings. The main residence showcases nearly 2,000 square feet of thoughtfully designed living space, featuring a primary bedroom suite with a glass enclosure sitting area that invites natural light to cascade throughout. Two additional guest bedrooms and a spacious living/dining area open through multiple sets of French doors, seamlessly blending indoor and outdoor living. Adding to the propertys allure is a separate studio guest cottage. This flexibility allows you to enjoy a tropical getaway during your visits while maximizing rental potential from the main house offering the best of both worlds. Ideally situated just a short stroll from pristine beaches, the iconic White Street Pier, and premier tennis and pickleball courts, this estate provides an unmatched opportunity to own a private oasis in one of the most sought-after destinations.

This is the ultimate living experience. You get all Historic Key West has to offer, but are tucked away on your own private island paradise. Access to Sunset Key is by the island ferry which runs 24 hours a day, but is only a 4 minute boat ride. Have all the fun you can stand in Key West, but then come home to absolute peace and quiet. Have your own Sunset Party from your covered roof top observation deck. The island has all the conveniences of a world class luxury resort, including three beaches within a minutes walk, a full service spa, golf cart parking, gourmet restaurant, tennis courts, and much more. Ample covered parking is available at discounted rates in the Opal Resort parking garage. For a truly unique and eye opening experience, call now and make an appointment for a private grand tour of the island. You will be glad you did!

Located in the highly regarded Casa Marina neighborhood, this exceptional property offers a unique opportunity to own a piece of Key West history. Ernest Hemingway the iconic literary figure once called this house his Winter retreat during 1928 -1929, where he penned the timeless classic, A FAREWELL TO ARMS. This sprawling single story property spans an impressive 8100 square feet, occupying a prominent corner lot, with a reimagined interior floor-plan. Constructed with white-painted Savannah brick over a wood frame, this residence exudes classic charm with a modern twist. Tall ceilings and a welcoming fireplace create an inviting atmosphere. Sliding glass doors seamlessly connect the interior to the outdoor patio, allowing for a harmonious blend of indoor and outdoor living spaces. The outdoor space is a tropical paradise, complete with a heated pool and soothing water feature. The main house features 3 bedrooms, 2 bathrooms, and a laundry area. Two of the bedrooms share a bathroom, while the primary suite offers a generously sized bathroom with a bath tub, double sinks, and an indoor and an outdoor shower. Enjoy the airy ambiance of the open floor plan, with a spacious living room and dining area that together span over approximately 1200 square feet. The modern kitchen is well-appointed, with easy access to the pool area and the charming conch-style 1/1 guesthouse. The main house has a semi-circular driveway and can accommodate 3-4 cars. The guesthouse also includes its own entrance on Walton Street and an off-street parking space.

Discover your dream Transient Vacation Rental in the heart of mid-town Key West! This beautifully refreshed home boasts a light and airy atmosphere and is sold fully furnished with rentals on the books and ready to go. Featuring three bedroooms, including a spacious primary suite and three baths, this property offers an inviting open living and kitchen area, highlighted by soft hues and vibrant tropical accents. Dine al fresco in the charming attached pavilion, perfect for enjoying the lush surroundings.Each bedroom provides direct access to different areas of the yard, enhancing the privacy and outdoor experience for every guest. The luxurious primary suite opens to the pool area through stunning French doors, while the primary bath features a spacious, tiled walk-in shower. The second bedroom, painted in serene green tones and decorated with inspiring Key West art, offers a tranquil retreat with two twins that may be turned into a king. The versatile third bedroom is on the opposite side of the house with remodeled bath ensuite.Nestled in a quiet residential neighborhood, this home is just a short bike ride from the beautiful beaches on the south side of the island and the vibrant Duval Street, with the Casa Marina area even closer. This home is the ultimate vacation getaway!

Expect the unexpected at 1400 1st Street, an exquisite retreat where unmatched craftsmanship meets island luxury. This custom-built 5-bedroom, 4-bathroom home offers a perfect balance of sophistication and quality. From the moment you step inside, the rich Brazilian cherry floors guide you through this elegant home, exuding warmth and elegance The chefs kitchen is a culinary dream, featuring polished granite countertops and top-of-the-line stainless steel appliances, including a Sub-Zero refrigerator and a six-burner Viking gas range. Custom tile work adorns each bathroom, elevating every space with exceptional detail.Soaring ceilings enhance the open-concept design, filling the home with natural light. Every poolside bedroom boasts its own private balcony, offering stunning views of the tropical surroundings. The expansive primary suite is a true retreat, featuring a private beverage center for added luxury and convenience. The spa-inspired primary bath includes a soaking tub and rain shower, creating an intimate oasis within your own home.Designed for effortless entertaining, the custom bar area is a true highlight. Equipped with a wine cooler, sink, and ice maker, its ideal for hosting memorable gatherings. Step outside into your private tropical oasis, where mature trees create a sense of serenity and two cascading waterfalls frame the serene swimming lagoon. A beautiful dining gazebo spans the water, perfect for outdoor dining and entertaining. Lush landscaping surrounds the entire property, providing privacy and an idyllic backdrop for relaxation.This home also includes a rare two-car garage, with secure parking for up to three additional vehicles or watercraft, offering unparalleled convenience. With its seamless blend of design, luxury, and functionality, this home is a true Key West gem.Just moments from the islands beaches, marinas, dining, and shopping, this property offers both tranquility and access to all that Key West has to offer!

Stately Key West home has undergone a stunning renovation but maintains classic Keys charm with a beautiful wood staircase, stained glass window and transom, Dade County pine walls, and wraparound porches on both levels. Centrally located in Key West this home is the perfect island residence with POOL! The main level offers plenty of room for entertaining with large spaces for conversation, dining, games, cooking, and more. Spacious chefs kitchen with breakfast bar and natural design elements throughout. Kitchen flows to the sitting area with designer bar space and wall of sliding glass doors opening to the pool and a pass-through window to covered porch area. Main level offers one bedroom with outdoor access and a full bath. The upper level boasts four additional bedrooms including primary suite. The primary bedroom is a resort like retreat with elegant spa tub, large walk-in shower with multi-jets, rain forest shower, linear drain and walk-in closet. The primary also features access to deck space perfect for morning coffee. Bedroom with en suite bath and deck access. The other upstairs two bedrooms share an en suite full bath. Perfect tree top views from upstairs on the wraparound porch. The third level is currently a music room and offers access to the widows walk for top of the island views! Lovely private outdoor areas with mature tropical landscape. Pool area with tiki hut offers covered space for reading or relaxing. Garage has room for parking or storing your island water toys. Laundry room on second floor and bonus washer & dryer in garage. Elevator to each floor. Central AC. This is the perfect island home!

Wonderful 3BD/3.5BA home with just over 3,000 sf of living space situated in the desirable Casa Marina neighborhood. Centrally located & just a short walk to Duval Street, the beaches, museums, galleries & many of Key West fine dining that it has to offer. With a spacious open floor plan & lots of windows & French doors throughout allow for plenty of natural light to fill this spectacular home. The master bathroom was recently renovated, a whole home generator was installed, a commercial on demand hot water heater was installed, new copper gutters and downspouts, newer Central A/C systems, downstairs interior was re-painted, composite decking on the exterior & a new carport canopy are all just some of the many great features this property has to offer. The kitchen has stainless appliances and the flooring throughout the downstairs & patio was replaced. Located just off the kitchen through the French doors you will find a large loggia which is an incredible space for your outdoor living & dining room where you can host family or friends comfortably. Upstairs you will find the master bedroom w/ ensuite bath and the 2 additional guest bedrooms. Off the master bedroom is a gorgeous & private sundeck which also has access to the pool deck via a spiral staircase. Additionally you can find stained glass throughout the home and cathedral ceilings. Property is located in the X Flood Zone and is completely fenced adding for that extra privacy. Potential for a great monthly vacation rental!

Located in Old Town Key West, and on one of the most sought after tranquil lanes, sits this perfectly updated home in the X zone. Upon entering, the foyer seamlessly flows into an open-concept living room and kitchen. Youre welcomed by a breathtaking cathedral ceiling that enhances the sense of space, while large pocket doors draw your gaze to the outdoors. An expansive lanai extends the living space, featuring a dedicated dining area and alfresco kitchen. This home offers three spacious en suite bedrooms, each thoughtfully designed for comfort and privacy. The Sea Grass green kitchen features a glass backsplash, quartz countertops, and top of the line appliances including a Wolf Range. The open loft space, currently furnished with twin beds, can easily be transformed into a home office. Tucked away in the loft is a hidden, generously sized closet, perfect for additional storage. The master suite, located just off the pool, boasts elegant built-in cabinetry. A hallway leads to the laundry facility, and two additional en suite bedrooms, one of which has its own private porch. The exterior of this home is truly exceptional, featuring IPE decking that surrounds a stunning 20 x 10 pool with a sleek tiled water feature, an outdoor shower, and tropical landscaping with a privacy fence. Most importantly, there is an antique, bricked driveway enough for two cars.

Welcome to this newly renovated architectural gem in Old Town Key West. This historic home has been meticulously renovated to blend timeless charm with modern sophistication. The main house offers three bedrooms, 3.5 luxurious baths, all illuminated by natural light pouring through impact-resistant doors and windows. Throughout, the warmth of oak floors complements the clean, contemporary lines of the space. The gourmet kitchen, fitted with Bosch stainless steel appliances, is a dream for culinary enthusiasts, while the open-concept design makes it perfect for entertaining. Step outside to your private oasis, where a stunning waterfall pool is the centerpiece of a lushly landscaped garden. The outdoor kitchen and spacious dining area are perfect for hosting al fresco dinners, making the most of the tropical Key West climate. For guests, a separate one-bedroom, one-bath guest house ensures privacy and comfort. Additional features include off-street parking and an electric vehicle charging station. Just two blocks away, the iconic Duval Street invites you to explore world-class dining, art galleries, and nightlife, with historic stops like Sloppy Joes. A two-block stroll west brings you to the literary haven of the Ernest Hemingway Home and Museum, while the Key West Lighthouse, just one block farther, offers panoramic island views.For beachgoers, the tranquil shores of Fort Zachary Taylor Historic State Park await, only five blocks away. History lovers will appreciate being just*five blocks from the Truman Little White House, a symbol of presidential retreat. Each evening, Mallory Square, also five block away, offers a festive sunset celebration, a must-see experience. For waterfront dining and sailing excursions, the Key West Historic Seaport is within the same easy reach. 907 Whitehead Street isnt just a home--its a luxurious retreat in the heart of Key Wests most coveted neighborhood, offering a blend of history, elegance, and walkable island living.