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

INVESTOR ALERT! Great opportunity to own a 3 unit building centrally located in Key West with off Street parking and plenty of room for a pool. The downstairs front unit is a 2BD/1BA, has an open floor plan with lots of windows allowing for plenty of natural light and a cute front porch. The upstairs unit is a 1BD/1BA and the rear third unit is another 2BD/1BA. The multi unit building sits on a nearly 4,000sf corner lot, consists of 2 structures and has just over 2,000sf of total living space. Located only a few blocks to Duval Street, the beaches, wonderful restaurants and many more of Key West attractions! Tenant occupied, minimum 24 Hour notice to show.

Effortless style, prime location, and outdoor living at its best. Welcome to your dream coastal beach cottage, tucked away in a quiet midtown neighborhood. This completely updated one-level home offers the perfect combination of privacy, convenience, and island charm. Just minutes from the beach and walkable or bikeable to Key Wests best restaurants and cafes, 1619 Rose Street is perfectly situated to embrace the ultimate island lifestyle.Step into a thoughtfully designed home with an open floor plan that flows seamlessly from the living area to the dining room, kitchen, and out to the expansive lanai. The master suite is a true retreat, with sliding glass doors opening directly to the pool area, a walk-through shower, and a custom-fitted walk-in closet.The centerpiece of this home is the lushly landscaped backyard oasis. Surrounded by tropical greenery, it features a heated pool, multiple outdoor living spaces, and a serene ambiance perfect for relaxing or entertaining. Completing this outdoor paradise is a detached one-bedroom, one-bath guest cottage with its own private deck overlooking the heated and chilled pool--ideal for visitors or a private home office.Modern design, thoughtful details, and the very best of Key West living await you in this stunning island retreat. Being sold furnished excluding artwork.

A true Historic Gem, meticulously restored to its former glory with a complete, ground-up revitalization. Every detail has been thoughtfully preserved and reimagined, blending timeless character with modern craftsmanship to create a stunning masterpiece that honors the past while embracing the future.Experience the ease and elegance of one-level living in this Island Inspired Retreat. This tropical haven features two impeccably styled bedrooms, each with its own Spa-like en-suite and spacious closets for effortless organization. Accent wood wall finishes add warmth and character while the hand selected tropical wallpaper, infuses each space with a vibrant, vacation-like ambiance.The Charming finished half-story on the second floor is a dream hideaway designed for fun, comfort and unforgettable memories. This inviting space features four built-in bunks, creating a cozy camp-like retreat thats perfect for grandkids, visiting family or extra guests.Each bunk is adorned with luxurious hand-selected linens, making it as stylish as it is comfortable. Whether its laughter-filled sleepovers or quiet afternoon naps, this whimsical bunk room promises to be a favorite spots for guests of all ages. The Spacious, thoughtfully designed kitchen is a gathering place for making memories, perfect for hosting family, friends and special occasions. The oversized island offers plenty of space for meal prep, casual dining or simply enjoying a cup of coffee while chatting with loved ones. From the Kitchen, youll enjoy the picturesque views of the beautifully appointed tropical living and dining area, featuring elegant wallpaper, a Featured Wood Finished Wall, gorgeous window covering, custom blinds and a stunning coordinated furniture package. The open layout also connects to the private new pool and patio area, perfect for relaxed get-togethers, holiday celebrations or quiet evenings under the stars. Addn features inc, 3 OSP, Turnkey, Above Flood, Storage, privacy.

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.

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.

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.

Embrace the laid-back Key West lifestyle at this three-bedroom, three-bathroom coastal retreat, perfectly positioned near Higgs Beach, White Street Pier, and the vibrant Key West Artisan Market. Located on a quiet cul-de-sac, this home is just steps from the dog park, play grounds, tennis & pickleball courts, and bocce ball- the best of island living is right at your doorstep!1621 Sunshine Drive is a beautifully updated two-story home. As you step inside you will find bright, modern interiors with bamboo floors and three generous bedrooms, including two with en-suite baths. Each bathroom is tastefully renovated with white subway tile, glass-enclosed showers, and sleek finishes. The first floor has a bedroom with access to the hall bath. Upstairs you will be greeted by two additional bedrooms both with balcony access which overlooks the lush gardens and pool area. The rear primary suite is a luxurious retreat, featuring double sinks, a built-in soaking tub, and spa-like ambiance.The reimagined kitchen boasts stainless steel Cafe appliances, including a six-burner gas stove, French door refrigerator, and custom cabinetry, accented with black hardware, white subway tile backsplash, island seating for 3 and white quartz countertops.Relax in the spacious living room filled with natural light that flows into an open floor plan. The living room opens to one of four covered porches and overlooks the private heated pool surrounded by newly planted gardens and Brazilian teak wood decking. Outside your tropical oasis awaits, complete with an outdoor shower and lush greenery- perfect for soaking up the island sunshine or entertaining under the stars.This home is equipped with hurricane impact windows and doors, two off-street parking spaces ,a laundry closet, and all the modern updates you need for easy island living. Whether youre seeking a tranquil retreat or the perfect home to become a vacation rental, 1621 Sunshine Drive offers the best of island living!

The Ultimate RV / Auto / Toy Vault. Happiness is having the space to enjoy your possessions, rain or shine! Heres an incredible chance to secure a solid and safe haven for your cherished possessions. Why leave your prized possessions behind when you migrate to Key West for the winter? This impeccably crafted structure is engineered to withstand winds of 180 mph and X flood levels. Featuring two expansive 12x14 overhead doors, it also boasts an inviting man cave with a full bath, along with a high quality 2-bedroom, 2-bathroom apartment on the second floor. If youve already acquired everything you desire, this building could be the missing puzzle piece to keep your possessions conveniently close at hand. Countless delightful surprises await the aficionado of toys. Perfect for boats, cars, RVs, or hobbies. This building offers endless possibilities. It is zoned as mixed-use land and is currently used as a residence with toys. Building is 2,730 sq. ft. total; Upstairs APT with 2 bd/2 ba is 805 sq. ft.; Garage with full bath is 1,925 sq. ft. Owners are licensed Real Estate agents.

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.

Welcome to this extraordinary property, a true gem completed in 2019, offering an unparalleled living experience with modern craftsmanship and exceptional features. Situated on an expansive double lot, this home blends beauty, durability, and functionality in every detail.Boasting solid Caribbean heart pine floors, pickled pine 20-foot ceilings, and custom-built kitchen cabinets, this home provides a warm and inviting atmosphere with a touch of elegance. Built to meet current Cat 5 hurricane codes, this home includes a foam-insulated roof, impact-resistant glass & doors, and an elevated foundation above base flood--ensuring peace of mind in extreme weather conditions.Featuring two large bathrooms and a convenient half bath, the home offers ample space for both comfort and privacy.Included on the property is a 1,548-square-foot commercial building, perfect for a business venture, workshop, or additional storage. This versatile space adds immense value to the property.Every inch of this home was built with attention to detail, ensuring a high standard of construction and design that stands the test of time. The oversized double lot provides plenty of outdoor space, allowing for a variety of possibilities from landscaping and entertaining. Plenty of room for a a large pool. Perfectly situated for privacy, yet close to essential amenities, this property offers the best of both worlds.This rare opportunity is a must-see for those seeking a one-of-a-kind home with added potential for business or personal use. Whether youre looking for a private sanctuary or a property with income-generating potential, this is the perfect fit. Schedule your tour today!

This beautifully renovated conch home is a proud recipient of the 2024 Historic Florida Keys Foundation Preservation Award. Originally built in 1906, it has been meticulously restored from the ground up, essentially making it a brand-new property. The home features off-street parking, a heated/chilled pool, and comes fully furnished, offering a turnkey experience. Situated within walking distance of restaurants, art galleries, and Duval Street, the location is ideal. A spacious porch with classic painted Cuban tiles provides a relaxing outdoor retreat, while reclaimed heart pine flooring extends throughout the interior. The open floor plan offers a seamless view from the living room to the pool deck, making it perfect for both relaxation and entertaining. The original tongue-and-groove Dade County Pine has been carefully removed, refinished, and reinstalled, creating a warm and inviting atmosphere.The L-shaped kitchen overlooks the heated dip pool and features custom craftsman shaker cabinets and quartz countertops. The master suite is conveniently located on the first floor, complete with an en-suite bathroom and walk-in shower. Two guest bedrooms, each with en-suite baths and vaulted ceilings, are located on the second floor.This home has been completely rewired, replumbed, and foam-insulated, ensuring compliance with modern building codes. A new foundation and a reinforced metal shingle roof have been added, along with fabric hurricane shutters for protection and insurance benefits. Smart switches, appliances, locks, and wired ethernet connectivity allow for remote home management via phone.The property is located in the X Flood Zone! The propertys historic charm makes it a remarkable piece of Key West history. Owner is a Lic. FL Real Estate Agent.

Luxury Waterfront Living in a Highly Desirable Boating Community.Discover unparalleled elegance in this fully renovated 3-bedroom, 3-bathroom en-suites concrete home, designed for the ultimate in modern coastal living. Every detail of this residence has been meticulously updated, including ALL NEW 2025 plumbing, electrical, and HVAC systems, ensuring worry-free ownership. Step inside to a completely reimagined interior, featuring high-end luxury finishes throughout. The open-concept design is bathed in natural light, enhanced by hurricane-impact windows and doors offering both beauty and peace of mind. The chefs kitchen is a masterpiece, boasting premium appliances, custom cabinetry, and exquisite countertops, seamlessly flowing into the spacious living and dining areas and bonus coffee/wine bar feature--perfect for entertaining. Each bedroom is a private retreat with spa-inspired en-suite bathrooms. The thoughtfully designed layout allows for guest access to one of the en-suite bathrooms, ensuring convenience without compromising privacy. An additional outdoor terrace bathroom access provides seamless functionality for those enjoying the exterior living spaces--perfect for rinsing off after a day on the water.The primary suite is a true sanctuary, opening through a set of sliding glass doors to a private covered terrace retreat. This serene outdoor space is ideal for morning coffee or unwinding in the evening, offering a peaceful connection to the surrounding coastal environment.All of this beneath a durable metal roof adding to the homes longevity and appeal. Located in an elite boating community, this property offers excellent water access, making it a dream for boaters and water enthusiasts alike. Experience luxury, security, and an unbeatable lifestyle in one of the areas most sought-after family neighborhoods. Select finishes by April 4 to add your own touch. Dont miss this opportunity--schedule your private tour today

PRICE IMPROVEMENT! Now being offered at under $575/sq ft! At 3,924 square feet, 2718 Harris Ave is one of the larger private residences in Key West. This impressive home offers an open and airy layout that is perfect for entertaining indoors and out. Entering through the majestic front door, youll immediately notice the high-end finishes and just how spacious the home is--marvel at the soaring ceilings and high windows in the main living area with ample natural light. The chefs kitchen is open to the living room, featuring top-of-the-line appliances (Viking, Bosch, Kitchenaid), and includes a coffee bar and built-in ice maker. The left wing of the house consists of 3 bedrooms and 3 bathrooms, including the oversized primary bedroom with a breathtaking bathroom and massive walk-in closet. The right wing of the house is ideal for guest quarters with a second-floor bedroom, en-suite bathroom, and private balcony. A concrete privacy wall surrounds the backyard and features lush tropical landscaping. The heated saltwater pool is perfect for relaxing in after a long day at work or out exploring the island; theres plenty of room to relax poolside or BBQ using the deluxe propane grill. Additional benefits include a whole house generator, two new air conditioning units, a rare large 9,165 sq ft lot, professional landscaping with turf, and plenty of off-street parking in the circular driveway and under the portico covered entrance. This home is being offered fully furnished. Whether youre looking for your forever home or investing in Key Wests thriving vacation rental market, this home is a must-see! Schedule your private showing today.

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!

Invest in Key West with this legal Duplex! Step into a piece of Key West history with this fully renovated, light-filled historic home in the heart of Old Town. Blending old-world charm with modern updates, this property offers easy living and generates income. Whether youre looking for a smart investment, a vacation getaway, or a new primary residence, this property is ready for you. Live in one unit and rent the other, or enjoy the entire home for yourself! There is an interior staircase to enter the upstairs unit.Each spacious level features 2 bedrooms, 1 bathroom, a full kitchen with stainless steel appliances, laundry, and an open-concept living/kitchen/dining area. The lower unit opens to a deck and pool--perfect for relaxing and entertaining. The upper unit boasts abundant natural light and a large wraparound porch, ideal for enjoying the tropical surroundings. Both units come fully furnished, and the upstairs unit has a long-term tenant in place, ensuring immediate rental income.Located in a prime spot close to the Old Seaport, top restaurants, and bars, but in a quieter neighborhood, this home is your ticket to island living in paradise!

Over 100k price reduction!Invest in Key West with this legal Duplex! Step into a piece of Key West history with this fully renovated, light-filled historic home in the heart of Old Town. Blending old-world charm with modern updates, this property offers easy living and generates income. Whether youre looking for a smart investment, a vacation getaway, or a new primary residence, this property is ready for you. Live in one unit and rent the other, or enjoy the entire home for yourself! There is an interior staircase to enter the upstairs unit.Each spacious level features 2 bedrooms, 1 bathroom, a full kitchen with stainless steel appliances, laundry, and an open-concept living/kitchen/dining area. The lower unit opens to a deck and pool--perfect for relaxing and entertaining. The upper unit boasts abundant natural light and a large wraparound porch, ideal for enjoying the tropical surroundings. Both units come fully furnished, and the upstairs unit has a long-term tenant in place, ensuring immediate rental income.Located in a prime spot close to the Old Seaport, top restaurants, and bars, but in a quieter neighborhood, this home is your ticket to island living in paradise!

Indulge in the essence of luxury island living at 1309 Royal Street, a meticulously reimagined Conch-style masterpiece nestled in the prestigious Casa Marina enclave. Rebuilt in 2024 with an unwavering commitment to craftsmanship and design, this elegant single-level residence offers 1,600 square feet of impeccably curated living space on a 4,350-square-foot lot in the highly coveted X Flood Zone.Perfectly positioned just moments from Key Wests pristine beaches, dog parks, tennis & pickleball courts, and the vibrant energy of Duval Street, this home is a sanctuary of sophistication and comfort.Step inside to an expansive great room and dining area, where white wood walls and ceilings exude coastal elegance, bathed in natural light. The gourmet kitchen, adorned with custom white shaker cabinetry, hand-crafted Zellige Moroccan tile backsplash, and top-tier Sub-Zero, Wolf, and Bosch appliances. Wide-plank washed oak flooring and white travertine accents elevate the ambiance creating a warm and inviting retreat.Designed for effortless living, the home is equipped with state-of-the-art zoned central heating and air, eliminating the need for mini-splits, while impact-rated windows and doors with aluminum shutters provide both style and security. An on-demand LP gas water heater ensures energy efficiency, complemented by an all-new electrical and plumbing system featuring high-end Kohler fixtures.Outside, a private tropical oasis awaits. A brand new pool with a tranquil water feature invites you to unwind, framed by lush landscaping and premium Trex decking. A private outdoor shower enhances the island lifestyle, while a dedicated dog run adds convenience for pet owners. The property is fully enclosed with new custom picket fencing and stainless steel hardware, offering the utmost privacy and exclusivity. Off-street parking for two vehicles completes this rare offering.Schedule your private showing today and experience this exquisite, turn-key retreat

Discover the perfect blend of modern elegance and island charm in this updated 5-bedroom, 4-bathroom Key West retreat. Just blocks from the beach and moments from the vibrant energy of Duval Street, this fully furnished home is ideal for full-time residency or a high-performing investment property.Step inside to an inviting open floor plan featuring gorgeous gray-blue tile flooring and a stylish kitchen with premium finishes. The main level boasts spacious living and dining areas, while the upper level offers two additional rooms--perfect for guests, a home office, or a cozy den. With accommodations for up to 14 guests, this home is designed for both comfort and convenience.Outside, escape to your private oasis featuring a large deck, lush landscaping, and an expansive pool--perfect for relaxing or entertaining. A detached pool house adds incredible value, offering a 1-bedroom, 1-bathroom studio with a kitchenette.With new exterior paint and thoughtful updates throughout, this home is a rare opportunity to own a slice of paradise in Key West. Dont miss your chance to experience the best of island living!

This Key West resort-style home sounds like an absolute dream! It combines the perfect blend of luxury, functionality, and tropical charm. With almost 2,800 sq ft of living space, 5 bedrooms, and 3 baths, its designed for both comfort and elegance. The fact that its just steps from White Street Pier and the beach makes it an ideal location for those who love coastal living. Some standout features includes an expansive lot at 7,775 sq ft, theres plenty of space for the lush tropical landscaping and custom amenities like the grilling area, electric gate, and the stunning 20x40 pool with a spillover spa (one of the largest pools in Key West). The heated and chilled pool makes it suitable for year-round enjoyment. Enjoy your own tropical Oasis with the daybed swing under the lanai next to a custom water feature is the perfect spot for relaxation. The tiki bar also sounds like a great place to unwind after a swim or a day out exploring Key West. The 12ft elevation and oversized windows let in tons of natural light, making the home feel airy and bright. The 20-foot cathedral ceilings add grandeur to the living areas, and the built-in bookshelves give the space a cozy, welcoming vibe. The High-end Kitchen with sleek countertops, stainless steel appliances, and top-notch finishes, the gourmet kitchen is both stylish and functional--perfect for entertaining guests or cooking up a family feast. This home seems to be a perfect blend of relaxation and luxury with a variety of features to enjoy both inside and out. It truly is a must-see for anyone looking to live in or invest in Key West!Separate Apartment: The one-bedroom, one-bath apartment is an added bonus--whether for a caretaker or potential extra income, it adds flexibility to the property.