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luxury houses for sale Key West, United States (page 2)

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House with pool and terrace Key West (United States)

Built in 2008, this stunning 3-bedroom, 3.5-bath pool home perfectly blends the timeless character of classic Key West architecture with the comfort and convenience of modern construction. Ideally located just a short stroll from shops, restaurants, bars, and the world-famous Duval Street, this home offers the best of island living. Step inside to a bright, open-concept main living space with a wall of stackable impact glass doors that seamlessly connect the indoors with the private outdoor oasis. Just beyond the doors, you'll find a custom heated pool with tranquil water fountains, surrounded by lush tropical landscaping that offers both beauty and privacy, all complemented by a brand-new travertine pool deck that enhances the space with both elegance and durability. Each bedroom features its own en suite bath and walk-in closet, offering comfort and convenience for you and your guests. Storage is abundant throughout the home--a rare find in Key West. For added peace of mind, the property is outfitted with full impact-rated windows and doors. The modern kitchen is equipped with sleek stainless steel appliances, perfect for entertaining or everyday living. The home features two-zone central AC (one unit per floor), and the third-floor primary suite offers a loft-like retreat with both central air and a mini-split system for personalized comfort. Currently operating as a successful vacation rental, this property offers excellent income potential. The home can be sold turnkey with furnishings included, giving buyers the option to move right in or start generating rental income immediately.

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$2,859,000
212
3bedrooms
3bathrooms
land 0ha

By Annonceur International

30

House with pool and terrace Key West (United States)

The ultimate lock-and-leave Key West retreat awaits in the heart of Old Town! Perfect for those seeking a low-maintenance getaway this residence offers effortless luxury living and the convenience of a fly-in, fly-out lifestyle.Located on exclusive Admirals Lane within the award-winning TRUMAN ANNEX. The home features soaring 10-foot ceilings on all three levels, a bright open floor plan, and a stunning modern kitchen with quartz countertops and stainless-steel appliances.With 4 bedrooms and 3.5 bathrooms, the layout provides flexibility and comfort for family and guests. The first floor offers spacious living and dining areas that open through impact French doors to a private tiled patio surrounded by tropical landscaping--ideal for entertaining. The second floor includes a spacious primary suite with ensuite bathroom and a guest room with a separate bathroom. The stacked washer and dryer is located on the 2nd level. The third floor provides a private guest area with two bedrooms and a shared bath, each featuring tall ceilings and two queen beds per room.Impact windows and doors throughout, assigned covered parking, and access to the Truman Annex community pool add to the ease of ownership. Just steps from Duval Street, fine dining, and the waterfront, this home delivers the best of Key West living--lock it, leave it, and love it.

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$2,975,000
231
4bedrooms
4bathrooms
land 147

By Annonceur International

30

House with pool and terrace Key West (United States)

Charming Multifamily Compound in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional multifamily compound, perfectly situated in a vibrant neighborhood. This property offers a unique blend of charm and modern comfort, making it an ideal investment or family retreat. The compound consists of 4 units, each exuding the distinctive character of Key West architecture, featuring high ceilings, large windows that invite natural light. The main house has its own private heated pool, hot tub and outdoor shower perfect for relaxation and entertainment. The main house also has 2 guest cottages off the pool. The next building has an upstairs unit with 2 bedrooms and a bath with it's own private deck. Below is a one bedroom one bath unit and up front is the 3rd unit with one bedroom and one bath. Benefit from plenty of parking spaces, accommodating residents and guests with ease a rare find in this bustling area. Nestled in one of Key West's most historic districts, this property is just minutes away from famous landmarks, restaurants, and local shops. Take advantage of nearby beaches, water sports, and lush parks, offering a vibrant lifestyle for outdoor enthusiasts. This multifamily compound not only serves as a wonderful family home but also presents a lucrative rental opportunity in one of the most sought-after destinations in Florida. Don't miss your chance to own a piece of Key West history. Schedule a viewing today. Owner financing is available.

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$3,750,000
280
7bedrooms
7bathrooms
land 0.1ha

By Annonceur International

30

House with pool and garden Key West (United States)

This super cute historic Old Town Key West 2,205 sq. ft. Conch-style home is perfectly positioned just steps from famous Duval Street and one block from the ocean, South Beach, and the Southernmost Point. If you're seeking the best location in Key West--walkable, vibrant, and effortless--this property is unmatched. The sun-filled first floor showcases timeless Dade County pine, cherry floors, and an open layout designed for easy island living. The spacious living and dining areas flow naturally into the chef's kitchen, complete with Silestone countertops, stainless-steel appliances and custom wood cabinetry. A cozy sitting room offers a quiet retreat, while a half bath with stackable washer/dryer adds convenience.Step outside to your private backyard oasis--lush landscaping, a covered pergola perfect for dining or lounging, and a sparkling pool create the ideal setting for relaxing or entertaining after a day exploring Old Town.The second floor offers two guest bedrooms with a shared full bath, plus a beautiful front balcony with peek-a-boo ocean views and the iconic Southernmost House--an ideal spot to unwind at sunset.The entire third floor is a luxurious primary suite, offering maximum privacy with reclaimed wood finishes, spray foam insulation, a spacious walk-in closet, and a spa-inspired bath featuring double Kohler body jets and a ceiling-mounted rain shower.Homes in this location--quiet, charming, and mere steps from Key West's best restaurants, galleries, beaches, and nightlife--are incredibly rare. This is the perfect retreat for buyers who want to enjoy the island on foot and live in the heart of everything.Come experience the best of Key West living. You will love this Old Town gem!

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$1,795,000
204
3bedrooms
3bathrooms
land 205

By Annonceur International

7 listings near Key West

Nearby
50
Video

House Key Haven (United States)

Where the essence of the Florida Keys meets refined coastal luxury, 94 Driftwood Drive stands as a rare bayfront sanctuary in coveted Key Haven. Just minutes from the energy and culture of Key West, this residence offers a lifestyle defined by serenity, sophistication, and seamless access to world-class cuisine and adventure. Framed by spectacular water views from every room, the home's architecture embraces its setting with an effortless elegance. A mesmerizing infinity-edge pool and spa appear to merge with the open sea, creating a private resort experience at the water's edge. Inside, the striking chef's kitchen commands attention with state-of-the-art appliances and a dramatic solid-walnut entertainment island--an exquisite centerpiece for gatherings both intimate and grand. Offering 5 bedrooms and 5.5 baths, including primary suites on both levels, the residence is designed for comfort, privacy, and elevated living. Hardwood floors, impact-glass windows, and an oversized 2-car garage with direct dock access and room for a boat trailer reflect thoughtful craftsmanship throughout. Flexible spaces accommodate a gym, studio, or entertainment room, while a meticulously organized storage area supports both home and pool systems with precision. For the boating and water-sport enthusiast, a dedicated equipment room provides direct access to the oceanfront dock and boat lift, placing the Keys' endless waterways at your doorstep. A custom iron staircase rising from the first to the third floor serves as a sculptural showpiece, its ocean-inspired artistry echoing the home's coastal surroundings. 94 Driftwood Drive is more than a residence--it is a statement of lifestyle, where tranquility and sophistication meet the unmistakable allure of the Florida Keys.

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$12,500,000
510
5bedrooms
6bathrooms
land 1,335

By Ocean Sotheby's International Realty

Nearby
30

Seaside house with pool and terrace Summerland Key (United States)

RARE Solar-Powered Waterfront Tropical Gem with TESLA Solar Storage Banks on Prestigious Sugarloaf Key! A rare opportunity to own a fully solar-powered waterfront residence featuring 26 solar panels and two Tesla Solar Powerwall storage banks, offering exceptionally low energy costs, backup power, and the potential to earn credits by supplying excess energy back to the grid. This elevated 3 BD, 2 BA, 1,764 SF home sits on exclusive Southpoint--only three homes from open water and just 20 minutes to Key West.Step inside to a breathtaking cathedral Cupola, soaring above the open living, dining, and great room. Impact-glass windows fill the space with natural light, highlighting the home's tropical architecture and warm coastal finishes. The kitchen is designed for effortless entertaining with a double island, stainless steel appliances, and new quartz countertops. The split floor plan creates exceptional privacy. The primary suite features a large walk-in shower, jacuzzi tub, double vanity, and a spacious walk-in closet that connects to a versatile laundry/fitness/office room--also home to the Tesla storage banks. The opposite wing offers two guest bedrooms and a dual-access bathroom with two private vanities. Enhance your waterfront lifestyle with an impressive concrete boat ramp for jet skis, boats, kayaks, and paddleboards, plus a newly installed 10,000 lb boat lift on a deep, wide, crystal-clear canal providing fast access to both the Gullf and Atlantic. The oversized 15,000 SF lot bursts with vibrant tropical landscaping and includes a newly completed tropical pool with natural rock feature. Enjoy sunset views and star-filled nights from the rooftop observation deck. Additional features include Andersen impact windows and sliding glass doors, low insurance costs, covered parking, and excellent storage below the home.A rare Keys offering combining sustainable energy, modern resilience, and luxurious waterfront living--an exceptional opportunity in today's market

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$1,595,000
163
3bedrooms
2bathrooms
land 1,393

By Annonceur International

Nearby
25

Seaside contemporary house with terrace Summerland Key (United States)

Contemporary coastal living meets premier boating access in this elevated 2BD/2BA waterfront home on a 12,500 sq ft canal-front lot with 100 ft of waterfront and coveted SW exposure. Ideally positioned on one of the only flow-through, crystal-clear canals in desirable Sugarloaf Shores, offering exceptional access to both the ocean and backcountry.Light-filled interiors showcase impact windows and doors, wood-look porcelain flooring, and an open-concept chef's kitchen with porcelain countertops, custom cabinetry, stainless steel appliances, and an entertainer's bar. The spacious great room and dining area flow seamlessly to a covered, screened porch--perfect for alfresco dining, sunset views, and watching dolphins pass through to Sugarloaf Sound.A full wraparound composite deck with marine-grade stainless steel railings enhances outdoor living. The expansive, landscaped yard offers ample room for a pool and includes two RV hookups. A rare opportunity for boaters seeking clear water, prime location, and effortless Keys living.

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$1,249,000
98
2bedrooms
2bathrooms
land 1,161

By Annonceur International

Nearby
30

Seaside house with pool and terrace Summerland Key (United States)

Introducing Blue Sky Pointe - the crown jewel of Sugarloaf Key. Perched on a gated 33,750 sq. ft. peninsula with approximately 730 feet of waterfront, this spectacular 4 Bed, 3.5 Bath modern coastal showpiece is surrounded by glistening water and enjoys Keys famous sunset views over Sugarloaf Sound. Fully renovated with premium craftsmanship, the home features a standing seam metal roof, PGT impact windows/doors, and Hardi board siding. Inside, enjoy a sunlit open-concept floor plan with soaring ceilings, a gourmet kitchen with quartz counters, premium stainless appliances, gas stove, a hidden butler's pantry, and a waterfront Bedroom wing, all oriented to frame the water from every room. Step outside and immerse yourself in resort-style living with a heated and chilled waterfront pool, soothing spa, hot tub, invigorating cold plunge, and a fire pit encircled by flickering tiki torches to gather with friends and family while sipping cocktails as the sun melts into the horizon. Lounge on the expansive covered porch while enjoying views of the peaceful nature preserve for incredible bird watching, and a setting that offers total privacy and serenity. Boaters will love the protected canal access with 2 boat lifts (8K & 12K lbs), just minutes from open water. Additional features include a 4-car garage with EV charger, covered RV Tiki with 50 amp service, whole-house 35kW generator (750-gal tank), whole house water softening system and Sonos throughout, including garage and outdoor zones. Whether you're seeking a private sanctuary, a trophy lot, or the ultimate Florida Keys lifestyle, Blue Sky Pointe delivers. This is the most premiere lot on Sugarloaf Key a once-in-a-lifetime opportunity.

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$5,200,000
247
4bedrooms
3bathrooms
land 0.3ha

By Annonceur International

Nearby
50

House with pool Sugarloaf Shores (United States)

Welcome to this spacious canal-front retreat set on an oversized half-acre lot with endless potential. This four-bedroom, 2,605 sq ft home offers a rare combination of water access, outdoor living, and privacy. Enjoy genuine Florida Keys living with a private concrete boat ramp, a dock, and direct canal access leading to mangrove-lined creeks and open water just minutes away. Whether you're exploring by paddleboard or kayak, or heading out on your boat to world-class fishing and diving, this location makes it effortless. The backyard is designed for relaxation and connection, featuring a pool, spa, and multiple outdoor patio areas, all surrounded by lush, mature tropical landscaping. Inside, the home features a renovated kitchen, bright open living spaces, and a large enclosed back porch that extends your living area and overlooks the pool, spa, and canal. With four bedrooms, generous square footage, and seamless indoor-outdoor flow, the home is ideal as a primary residence, seasonal getaway, or investment property with tremendous upside. Located just minutes from Key West yet surrounded by the peace and natural beauty of Sugarloaf, this property offers the best of both worlds: space, privacy, and direct water access that's hard to find, along with the freedom to create your ideal island retreat.

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$1,710,000
242
4bedrooms
2bathrooms
land 2,575

By Ocean Sotheby's International Realty

Nearby
30

Seaside house with pool Summerland Key (United States)

Welcome to Morning Glory - The Dolphin House, a rare direct oceanfront retreat in the Florida Keys. Situated on an oversized oceanfront lot, this 4BR/3.5BA home offers 2,478 SqFt of coastal elegance, breathtaking Atlantic views, and the peaceful lifestyle buyers dream about. Wake up to stunning sunrises, relax by the pool beneath swaying palms, enjoy waterfront dining with guests and friends, or unwind by the fire pit under the stars. Every space was designed to feel warm, inviting, and effortlessly luxurious. More than a home, this is a private sanctuary where memories are made and life slows down.

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$3,750,000
224
4bedrooms
3bathrooms
land 0.2ha

By Annonceur International

Nearby
30

Seaside house with pool and garden Summerland Key (United States)

Introducing Blue Water Lagoon Estate! Experience unmatched privacy and exceptional waterfront living at this gated 2.33-acre oceanfront estate in exclusive Sugarloaf Beach -- a location famously featured in the film ''True Lies''. Designed for the avid boater and those seeking a resort-style lifestyle, this 5,208 sq. ft. residence offers rare amenities and direct access to world-class fishing and diving.A protected 6-boat basin with room for extra boats is the centerpiece of the waterfront, complete with 25K and 16K lifts, a boat ramp, sandy beach, lookout point, and composite observation deck. After a day on the water, unwind in the lagoon-style saltwater pool with heater, chiller, and custom water features. The expansive tiki bar includes TVs, True refrigerator/freezer drawers, and an ice machine--perfect for effortless outdoor entertaining. Additional features include a firepit, private sandy beach, and a full outdoor kitchen equipped with built-in BBQ, Viking appliances, and True refrigeration.The upper level offers a bright and open Great Room with sweeping ocean views, a spacious dining area, and a chef's kitchen with stainless appliances. Two covered verandas provide ideal spaces for taking in the breezes and panoramic vistas. The primary suite features an office, en suite bath, walk-in closet with laundry, sunroom, and loft. Two additional upstairs guest rooms comfortably accommodate visitors, while the separate downstairs living area offers three more guest bedrooms for privacy and flexibility.Designed for hosting and convenience, the home is equipped with a Sonos sound system, property-wide Wi-Fi, abundant storage, a two-car garage with fishing lockers, and generous parking along a winding paver driveway. Lush, mature landscaping surrounds the property, creating a serene and secluded Sugarloaf Key retreat.Call for more information today!

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$8,995,000
483
6bedrooms
5bathrooms
land 9,432

By Annonceur International

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