Florida Keys LUXURY Homes for Sale, Single Family Houses, Florida Keys Real Estate

Welcome to this charming Old Florida-style cottage, an ideal weekend retreat nestled on Lower Matecumbe Key in Islamorada! This property is set on nearly half an acre, boasting an impressive 100 ft of private beach frontage directly on the crystal-clear ocean. This cottage is a perfect fixer-upper opportunity, offering you the chance to renovate and personalize the existing structure or build your dream home on this stunning piece of prime real estate. Step inside to discover two spacious bedrooms and two full bathrooms. The interior features beautiful beamed and tongue-and-groove ceilings, adding a touch of character and warmth to the space. Imagine starting your mornings with a cup of coffee or unwinding in the evenings with a glass of wine, all while enjoying breathtaking views of the magnificent Atlantic Ocean. The gentle ocean breezes create a serene atmosphere, perfect for quiet contemplation and entertaining friends and family. With its prime location and charming features, this cottage is a rare find that invites you to embrace the laid-back Florida Keys lifestyle. Dont miss your chance to make this idyllic getaway your own!

What a great location! Discover Serenity at Manatee Crossing, nestled along the picturesque waterways of Islamorada, where over 200 feet of waterfront embrace you from two sides. Immerse yourself in an outdoor haven, boasting a captivating pool, charming Chickee-hut, and indulgent hot tub area - each offering front-row seats to the wonders of nature. From manatees to graceful migratory birds, the surrounding mangroves create a natural sanctuary for this remarkable property. Step inside this timeless CBS home, where modern comfort harmonizes with island charm. The lower level welcomes you with a living area and full bath, while three bedrooms and three baths await on the upper level. As the sun sets, ascend to the expansive concrete roof and toast to another day in paradise, with panoramic views painting the sky in hues of orange and pink. For boating enthusiasts, get ready to launch into your aquatic adventures, while nature lovers can explore the bay at their own pace, taking in the unique beauty of Tavernier Creek and beyond. Whether you seek thrilling ocean escapades or peaceful backcountry journeys, this property offers the perfect launchpad for all your Florida Keys dreams. Dont miss the chance to experience the magic of Manatee Crossing - schedule your private tour today and discover why this property is truly special.

Welcome to Ocean Drive! This exquisite waterfront property is in the charming enclave of Tropical Atlantic Shores, where paradise awaits you. Nestled along a deepwater canal, this solid concrete construction and freshly painted home boasts unparalleled direct ocean and bayside access through Tavernier Creek. Step inside and experience the allure of a modern residence that has been meticulously designed to blend contemporary comforts with timeless elegance. Built with two separate apartment-style spaces downstairs, this property could serve as an excellent investment opportunity or vacation home for avid water enthusiasts. The main living level upstairs offers two bedrooms and one bathroom with an interior staircase leading downstairs to a studio-style apartment with a private entrance. The fourth bedroom is a separate apartment accessed by a private entryway. Expansive screened porches on either side of this home offer even more space to take in the fresh ocean breezes. The 70 concrete dock is equipped with two boat lifts, one 15,000 pound lift for center consoles and a 3,000 pound lift for smaller vessels, plus davits. Mature fruit trees, turf on both sides of the house plus tropical landscaping fleck this oversized lot, complete with a tiki hut for entertaining, two storage sheds, and room for a pool. Enjoy peek-a-boo sunset views from the rooftop observation deck. Updates to this coastal contemporary include impact resistant windows and doors, travertine marble and porcelain tile flooring and exposed pine ceilings. An opportunity to own an exceptional waterfront property in Plantation Key with its remarkable features and prime location.

Easy Walk to Sombrero Beach in Marathon and Easy Ocean Access. Large Concrete Home with a Privacy Wall and roughly 50 of Concrete Dockage with a Boat Lift. Out back you will be greeted by a large wooden patio perfect for enjoying the Keys Weather, with a raised wooden deck outside with the Hot Tub. Inside you will see no detail has been spared. Beautiful tile floors, Quartz counters, Stainless Steel Appliances, Coffee Bar, Impact Windows and Doors, On Demand Water Heater, High Ceilings and more. House is a successful vacation rental and can be sold completely furnished. Walk to the Beach and less than 2 minutes out to Open Water. This is truly a must see with location and features that are hard to match.

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.

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.

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.

Tucked away on one of Key Wests most private and secluded streets--seriously, if youve never been to 913 Watson Street, youve probably never been on this block--this meticulously reimagined historic home, built prior to 1912, is the epitome of island living. Located in the coveted Old Town neighborhood and Key Wests highest elevation (X-500 Flood Zone), this property seamlessly blends historic charm with modern conveniences. Every inch of this residence, completed in April 2025, has been thoughtfully revitalized with no expense spared. Were talking historic-approved impact-rated windows and sliding doors, a brand-new roof, plumbing, electrical, HVAC, and foundation piers, plus gleaming hardwood floors. Step inside the main house, where youll find a bright and airy one-bedroom, 1.5-bath layout featuring a stylish kitchen with all-new appliances, a dedicated laundry room, and tranquil garden and pool views. Oversized sliding doors blur the lines between indoor and outdoor living, leading you to a serene outdoor space complete with a saltwater cocktail pool, water feature, and composite decking--ideal for al fresco dining, lounging, or simply enjoying the tropical ambiance. Directly across from the main home is the separate guest house, which could serve as a second full bedroom or a spacious living room. This versatile space includes a large walk-in closet, en-suite bathroom, and tranquil pool views, offering both comfort and privacy. The property also features a large carport, offering ample space for parking. And lets talk location--walking and biking distance to Key Wests top restaurants, nightlife, and beaches, yet nestled on a street so private, it feels like a secret.

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.

**Waterfront Paradise: Solid Concrete Home on Deep Water Canal**Nestled along a serene deep water canal, this exquisite solid concrete home awaits its new owner. Embark on a brick paver driveway that leads to a turn-key residence designed to impress.As a boaters paradise, this property boasts a private boat lift, davit, clean out station, and outdoor shower. Access to the communitys boat ramp allows for effortless excursions.Step inside and be captivated by the beautifully furnished interior with breathtaking canal views. The open floor plan seamlessly blends the gourmet kitchen, dining area, and living room, offering an inviting space for entertaining and relaxation. Top-of-the-line appliances and entertainment areas elevate the living experience.The spacious master bedroom and bathroom provide a luxurious oasis with access to a large screened balcony. The master bathroom features a soaking tub, separate shower, and double vanity.The downstairs level offers an enclosed garage with two bay doors and ample storage. A custom-made bar, full bathroom, and additional storage space create a versatile flex room perfect for various uses.The propertys tranquil exterior features lush landscaping, gardens, and a charming front porch. The rear stairs provide convenient access to the waterfront.With a straight shot to the bay and just around the corner from the ocean via Tavernier Creek, this home offers unparalleled access to the water. The neighborhood community offers a boat ramp for members.This dream home is a rare find. Dont miss this opportunity to own a piece of paradise. Call today to schedule a private showing and experience the beauty of this solid concrete waterfront residence. Call Today!

Exclusive opportunity to own this canal-front duplex and the adjacent vacant lot in Indian Waterways subdivision of Islamorada, FL. Each unit features two bedrooms, one bathroom, original custom kitchen cabinetry, and terrazzo floors. A connecting interior door allows the property to function easily as one expansive home or continue to be used as two separate living spaces. Boating enthusiasts will appreciate the 33-foot dock on a wide canal with direct access to the Florida Bay. The combined lots span 0.40 acres and are adorned with mature native plants and trees including Short Leaf Fig, Pigeon Plum, Mahogany, Locust Berry, and Crabwood -- creating a haven for birds and butterflies. Conveniently located near schools, Mariners hospital, grocery stores, shopping, entertainment, and Founders Park, which offers a swimming pool, bayfront beach, playground, pickle ball, tennis, and dog park. Whether youre seeking a primary residence, vacation home, investment, or redevelopment opportunity, this property invites you to live, work, and enjoy the tropical Florida Keys lifestyle.

RARE double ocean front lot featuring 120 ft seawall with amazing views. Potential to build large new home and lot size allows for a separate building for mother-in-law apartment right on the ocean! Existing double wide trailer is livable or rentable-occupies 1/2 of property leaving plenty of space for boats, trailers, parking, even a pool!!Close to downtown and airport.

Renovated, highest quality. New heated pool, ipe deck, new metal shingle roof, entire two bedroom is brand new.6,254 square feet of land, corner lot, park your RV, add guest house, etc. Two on site parking spaces. Home was renovated to convert to single family, currently set up as two units, one two bedroom, two bath with large sleeping loft and a one bedroom, one bath, (two legal units). Both floor plans attached, as is and the proposed conversion to single family. Tennis courts across the street. Keep as is and rent one side or easily finish conversion to single family. Room for your RV on the very large fenced lot. Current owners are licensed Florida Realtors.

Waterfront Retreat in Sugarloaf Key - A Boaters Dream!Located on prestigious Sugarloaf Key, only 20 minutes from Key West, this meticulously maintained 4-bedroom, 3-bathroom home offers seamless indoor-outdoor living with breathtaking water views and boating access to world-class fishing and diving. The 12,500 sqft lot is situated in a prime location only one in from open water on a crystal-clear, wide canal with a 100-foot concrete seawall, davits, and ample dockage. Surrounded by lush tropical landscaping, it feels like a private sanctuary, where swaying palms and rare bird sightings create a peaceful retreat. The open-concept living space features a well-appointed kitchen with stainless steel appliances, an island, and generous storage. A split-bedroom floor plan ensures privacy, with two primary suites on opposite ends of the home. The 2 guest rooms are separate with a shared bathroom which makes this home ideal for ultimate privacy for guests. Additional highlights include a home theater room and an expansive covered entertaining area beneath the home, complete with a custom-built bar and a cozy fire pit. Outdoor spaces include spacious decks, a screened in covered porch, a private rooftop terrace for sunset views and stargazing, and a one-of-a-kind outdoor shower, crafted from an original Key West ticket booth. A separate enclosed room on the ground level offers flexibility as a massage space or additional storage. A large garage, covered parking, and a circular driveway provide ample space for vehicles and guests. With plenty of room to add a pool, this home offers endless possibilities to enhance your outdoor living experience. Whether youre hosting a gathering or unwinding after a day on the water, this exceptional property captures the best of the Florida Keys lifestyle. Dont miss this rare opportunity to own a prime waterfront home in Sugarloaf Key! Check out the 3D floorplan to view the sprawling layout and video here https://tinyurl.com/4c46fzsm

ANGLERS REEF OCEANFRONT HOME WITH DEEDED DOCK. RARE OPPORTUNITY to own an oceanfront home in the prestigious Anglers Reef development in Islamorada. Deeded boat slip accommodating up to a 31 ft boat included in offering. A beautiful 2-bedroom, 2.5-bath, 2-story home with 2 porches and a balcony overlooking the Atlantic Ocean. Located in the gated community of Anglers Reef on Windley Key approximately half way between Miami and Key West. This property contains 2 large bedroom suites with bathrooms on the 2nd floor. A living room, kitchen, dining room and powder room on the main level. Looks out on the community pool and marina (see included video). Upgrades include impact windows/doors, metal roof, composite decks/railings, granite counter tops with wood cabinets, tile floors downstairs and bamboo floors upstairs, shutters/blinds, brand new dishwasher and refrigerator. The community features 2 sandy beaches, pool, gated entry, marina, kayaks and paddle boards. Perfect home for primary residence, vacation family home or investment property. Call today for a showing

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!

Exceptional waterfront pool home in Summerland Key! This beautifully updated 2156sqft concrete home is located in the desirable neighborhood of Summerland Cove, known for its incredible boating access, deep-water flow through canals and close location to Key West (just 24 miles). Enjoy the ocean and lagoon views from the kitchen, living room, dining room, loft and screened patio, or from the 64 long concrete dock! Dock comes equipped with boat davits, fish cleaning station with water and swim ladder. With no rear neighbors there is plenty of privacy to lounge by the pool (has a pool heater/chiller), throw in a paddle board or kayak and cruise the lagoon or take advantage of the incredible boating/ fishing that Summerland has to offer with quick access to the Atlantic Ocean and the Gulf! This newly updated home includes 2 bedrooms on the main level, 600 sqft loft upstairs used for a 3rd bedroom and 2 bathrooms, brand new kitchen with quartz counters and stainless appliances, impact windows and new impact sliders, 2016 metal roof, newer 263 sqft garage/storage and plenty of room for parking with a higher than usual 12 clearance under the house, able to park boats, trailers and/or RV (and yes there are RV hook ups!)

This 2,000 sq ft concrete fortress was designed and built by the current owner and sprawls over 3 waterfront lots boasting 325 of canal frontage. Enjoy fantastic fishing and diving just minutes away from the the 180 deep draft concrete dock complete with boat basin, private boat ramp and davits. Upon entering this 3 Bedroom, 3 Bath home, you are greeted with an oversized Great Room which opens to the Chefs Kitchen enhanced with sleek white cabinetry, stainless steel appliances, gas range, wall oven, walk-in pantry and center island for friends and family to gather around. The first floor is also home to a Guest Bedroom and Bath and the Primary Suite featuring a large bathroom, walk-in closet and direct access to the large screened veranda overlooking the water. The 2nd story offers an ensuite Guest Bedroom and Office/Den plus a Porch with amazing 360 degree sunrise to sunset views. Plenty of room for all off your toys with 1,450 sq. ft. of Garage and storage. The 2 additional adjoining lots is the perfect place for a pool, RV and accessories and ensures complete privacy. Storm ready with impact doors and windows and metal roof. Jolly Roger Estates is a small coastal community of waterfront homes just minutes to dining and shopping and the magic of Key West less than 30 minutes away.