Key West Homes with Metal Roof

New construction, Elevated 3BD/3.5BA with heated pool and gated off-street parking on coveted Olivia Street. The Twins on Olivia is a Key West landmark reborn. The original structures, known locally as 'Olivia's Twins' and documented on the 1892 Sanborn maps, were condemned by the city and demolished. In their place, Kanga Construction has built an all-new 2,421 sq ft home on a 2,773 sq ft lot, designed with extensive guidance from Key West's HARC to honor the original twins in form and spirit. That history lives on in two separate staircases, a nod to the original pair of homes that also gives guests or family their own side of the house. All three bedrooms have ensuite baths and built-in closets, and dual-zone A/C with two whole-house dehumidifiers keeps every room comfortable year-round. French oak floors run throughout bright, open living spaces. The kitchen pairs Viking appliances, including a gas range and ice maker, with custom Hansel & Bringle cabinetry and quartz countertops. Impact-rated windows and doors, among them a custom mahogany front door with matching mahogany entry and lattice details, combine island craftsmanship with hurricane protection. Outside, ipe decking surrounds a heated pool with waterfall, set within private tropical landscaping. Off-street parking sits behind an electric gate. The home is offered fully turnkey, with a curated furniture package by local designer David Smith valued at over $150,000 plus plantation shutters throughout, all steps from Old Town's best restaurants, galleries and landmarks. Historic Key West character, built new.

1010 Olivia St, Key West

$1,195,000

3 Beds ⋅ 2 Baths ⋅ 621482 MLS

Welcome to your dream home in the heart of Key West's MidTown! This beautifully updated 3-bedroom, 2-bathroom residence blends modern comfort with island charm. Step inside to a spacious, open-concept living area designed for both relaxing and entertaining. The true highlight is the private backyard oasis -- featuring a sparkling pool surrounded by fresh tropical landscaping, an expansive deck, and plenty of room for outdoor dining and lounging. Whether hosting guests or enjoying a quiet evening under the palms, this outdoor retreat feels like your own private paradise. Recent renovations provide peace of mind, including new impact windows and doors, Hardie board siding, and other thoughtful upgrades. Off-street parking adds everyday convenience. Perfectly located in the desirable MidTown neighborhood, this home keeps you close to shopping, dining, and all the best of Key West living. Don't miss this opportunity to own a beautifully updated slice of paradise in Key West -- schedule your private showing today!

2911 Seidenberg Ave, Key West

$1,695,000

4 Beds ⋅ 5 Baths ⋅ 621480 MLS

LOCATION! Situated on Garrison Bight, across the canal from the Key West Yacht Club, 5 Hilton Haven Dr. provides the best boating access on Key West. Tremendous opportunity for a buyer with a vision. The 4-bedroom, 4.5 bath, 2,027 sq. ft. home that is currently divided into 4 separate units in need of extensive repair. Or this home could be a good candidate for rebuilding as your single-family dream home with a pool, separate pool house, and 60' of dockage. Tucked away on one of Key West's few private drives, the home enjoys limited traffic and added privacy. Equipped with 2 electric meters and 9,058 sq. ft. lot, this property offers options and flexibility for bringing your vision to life.

5 Hilton Haven Dr, Key West

$1,169,000

2 Beds ⋅ 3 Baths ⋅ 621479 MLS

Your Old Town Key West dream can start now -- with income built in. This exceptional 2-bedroom, 2.5-bath, townhouse-style condo offers a rare combination of Old Town lifestyle, flexible living space, and income-producing potential. Currently configured with a lock-off 1-bedroom apartment, the property offers an ideal opportunity for the future Key West homeowner: enjoy the larger 1 Bedroom, 1.5 Bath unit with private garden/patio as your own Key West retreat while the lock-off apartment provides substantial annual rental income. When the time comes to make Key West your full-time home, the property can be easily converted back to its original spacious 2-bedroom townhouse-style layout. A private gated entry opens to your own generous outdoor oasis, complete with a waterfall pond, large patio, and charming ''she-shed'' -- perfect for storage, an art studio, or entertaining. Inside, you'll find high ceilings, abundant natural light, generous storage, in-unit washer/dryers, and newer stainless-steel appliances. Just two blocks from Duval Street in the heart of Old Town's vibrant Bahama Village, you're surrounded by restaurants, galleries, shops, nightlife, and countless Key West attractions -- all within easy walking distance. Whether you're ready for a Key West home now or envision making the island your full-time home in the future, this is a rare opportunity to own your piece of Old Town, enjoy income along the way, and ultimately create the spacious Key West home you've been dreaming of. Some seller financing considered. Seller is a Florida Licensed Realtor. Photos 10-17 show Original Layout, 18=FloorPlan, 19-37 show Back Unit, 38-49 show Front Lock-Off Apt.

927 Thomas St Unit 1, Key West

$3,400,000

5 Beds ⋅ 4 Baths ⋅ 621477 MLS

Discover the perfect blend of transient investment potential and coastal charm on Atlantic Boulevard. Just steps from the beach, this exceptional property offers a truly enchanting lifestyle with a distinctive boho-coastal aesthetic. The Atlantis House featuring five bedrooms and four bathrooms across three thoughtfully curated living spaces, this one-of-a-kind compound combines character, comfort, and style with an exciting opportunity for transient rental income. The primary residence is an exquisite 3-BR/2-BA monthly rental boasting a light-filled, open-concept floor plan for effortless island entertaining. You are welcomed into a mosaic-tiled foyer featuring whimsical swinging hammock chairs and a charming custom scooter coffee bar, flowing into spacious living areas adorned with timeless terrazzo floors. The heart of the home is a true gourmet kitchen, featuring a large island, pristine white quartz countertops, and separate Sub-Zero refrigerator and freezer. The main level offers two luxurious bedrooms opening to a beautifully landscaped fenced yard with a bistro patio. A spiral staircase leads upstairs to a third bedroom--a spectacular oasis with open water views. This level features dual sliding doors opening onto a magical, Trex rooftop terrace with a dining pergola and views of the Atlantic. It is the perfect perch to watch the sunrise with coffee in hand and return for the sunset. Around the corner are two detached, transient-licensed 1BR/1BA guest suites with dedicated parking. Both offer tasteful decor and private access to a backyard oasis with a large shared deck shaded by towering palms. Live the ultimate Key West lifestyle, a stone's throw from launching your kayak at the beach and a one-minute walk from the iconic White Street Pier. The Atlantis House conveys with its own house-made Atlantis Key Lime Pie recipe, passed from the former owner to the new owner, a tradition carried for more than 30 years. A one-of-a-kind treasure!

1401 Atlantic Blvd, Key West

$3,400,000

5 Beds ⋅ 4 Baths ⋅ 621476 MLS

Discover the perfect blend of transient investment potential and coastal charm on Atlantic Boulevard. Just steps from the beach, this exceptional property offers a truly enchanting lifestyle with a distinctive boho-coastal aesthetic. The Atlantis House featuring five bedrooms and four bathrooms across three thoughtfully curated living spaces, this one-of-a-kind compound combines character, comfort, and style with an exciting opportunity for transient rental income. The primary residence is an exquisite 3-BR/2-BA monthly rental boasting a light-filled, open-concept floor plan for effortless island entertaining. You are welcomed into a mosaic-tiled foyer featuring whimsical swinging hammock chairs and a charming custom scooter coffee bar, flowing into spacious living areas adorned with timeless terrazzo floors. The heart of the home is a true gourmet kitchen, featuring a large island, pristine white quartz countertops, and separate Sub-Zero refrigerator and freezer. The main level offers two luxurious bedrooms opening to a beautifully landscaped fenced yard with a bistro patio. A spiral staircase leads upstairs to a third bedroom--a spectacular oasis with open water views. This level features dual sliding doors opening onto a magical, Trex rooftop terrace with a dining pergola and views of the Atlantic. It is the perfect perch to watch the sunrise with coffee in hand and return for the sunset. Around the corner are two detached, transient-licensed 1BR/1BA guest suites with dedicated parking. Both offer tasteful decor and private access to a backyard oasis with a large shared deck shaded by towering palms. Live the ultimate Key West lifestyle, a stone's throw from launching your kayak at the beach and a one-minute walk from the iconic White Street Pier. The Atlantis House conveys with its own house-made Atlantis Key Lime Pie recipe, passed from the former owner to the new owner, a tradition carried for more than 30 years. A one-of-a-kind treasure!

1401 Atlantic Blvd, Key West

1901 S Roosevelt Blvd Unit 208E, Key West

$1,349,000

3 Beds ⋅ 2 Baths ⋅ 621474 MLS

Direct ocean views await at this rarely available 3-bedroom, 2-bath condominium in Key West's gated La Brisa community, directly across from Smathers Beach. Whether you're seeking a full-time residence or a seasonal escape, Unit 208E offers bright living spaces, an updated kitchen, and resort-style amenities. The open floor plan connects the kitchen, dining, and living areas, creating an inviting space for everyday living and entertaining. Sliding glass doors open to a private balcony overlooking the ocean--an ideal setting for morning coffee and enjoying the sea breeze. The updated kitchen features modern cabinetry and ample counter space. The primary suite features ocean views through a large picture window, direct balcony access, generous closet space, and an en-suite bath. Two additional bedrooms offer comfortable accommodations for family and guests or space for a home office. La Brisa's amenities include a heated pool, hot tub, tennis and pickleball court, clubhouse, BBQ area, EV charging stations, and gated entry. Enjoy convenient access to the beach, bike paths, airport, and Key West's dining and attractions. Seller is a family member of the listing agent.

1901 S Roosevelt Blvd Unit 208E, Key West

$1,725,000

4 Beds ⋅ 4 Baths ⋅ 621472 MLS

Tucked behind the gates of Seaside Residences, this exceptional 4-floor Townhome delivers the kind of Atlantic views most people only dream about. With four generous bedrooms and four beautifully appointed bathrooms, this home blends comfort with effortless style. A private four-stop elevator glides you between floors, while six separate balconies give you endless options for your morning coffee or evening cocktail: some framed by open ocean, others overlooking lush, tranquil surroundings. The chef's kitchen doesn't disappoint: high-end appliances, a trash compactor, in-unit trash chutes, and a pantry large enough to keep everything organized. First-floor laundry adds everyday convenience, and storage is never an issue thanks to closets tucked throughout the home. Step outside to your own private, garden lined patio and outdoor shower makes rinsing off after beach days effortless. Inside, granite counters and hardwood floors run throughout, and the attached garage comes with an automatic opener. Climb the indoor ladder up to your rooftop deck for unbeatable stargazing or sunbathing with a bird's eye view of the coastline. Residents also enjoy access to the community's shared pool, perfect for a relaxed swim without the upkeep of a private one. Fully furnished with high end furnishings throughout, this Townhome is a rare find in one of the area's most prestigious gated communities where luxury truly meets the ocean.

37 Seaside South Ct, Key West

$799,000

3 Beds ⋅ 3 Baths ⋅ 621467 MLS

Welcome to 2506 Seidenberg Avenue, a spacious 3-bedroom, 3-bath home offering 1,922 square feet of living space in the heart of Midtown Key West. Framed by tropical landscaping and a classic white picket fence, this home offers plenty of space and a flexible layout for comfortable island living. The main living area flows into a large eat-in kitchen featuring abundant cabinetry, stainless steel appliances, generous counter space, and plenty of room for dining and entertaining. Three bedrooms and three full baths provide ample accommodations, while additional living space at the rear of the property offers added flexibility for guests, a home office, den, or private retreat. A garage provides valuable parking and storage. Centrally located just minutes from Old Town, beaches, shopping, dining, and all that Key West has to offer. With nearly 2,000 square feet, versatile additional living space, a garage, and a convenient Midtown location, 2506 Seidenberg Avenue presents a unique opportunity to make a Key West home your own. Owner financing may be available.

2506 Seidenberg Ave, Key West

$6,895,000

6 Beds ⋅ 7 Baths ⋅ 621466 MLS

The Autograph House is a newly built, architect-designed luxury property in the heart of Old Town Key West, ideally positioned just one block from Duval Street and the island's most celebrated attractions. Blending refined modern design with the relaxed elegance of Key West, this exceptional property offers a rare combination of sophistication, privacy and walkable convenience. The home encompasses a stunning two-story Main Residence with four private bedroom suites, each featuring an en-suite bath with custom millwork, along with a beautifully appointed two-bedroom, two-bath Guest Cottage. Together, the residences create an exceptional six-bedroom, six-bathroom estate ideal for multi-generational living, extended stays, or entertaining. The Main Residence features an expansive open-concept living, dining, and chef's kitchen with premium Miele appliances, Fisher & Paykel column refrigeration, custom cabinetry, and a generous island. Floor-to-ceiling impact-rated sliding glass doors open seamlessly to a covered outdoor living and entertaining area, complete with lounge seating, a fully equipped outdoor kitchen, grill, beverage refrigerator, and dining space. Lush tropical landscaping surrounds a private heated pool and separate hot tub. The Main Residence pool features a waterfall and built-in bench seating, while the Guest Cottage offers its own private spa hot tub. An outdoor shower and secluded garden spaces further enhance the resort-like setting. Throughout the property, custom finishes, beautiful furnishings, Sonos audio, and full-size laundry facilities reflect an exceptional level of comfort and attention to detail. Perfectly situated in Old Town's X-Flood Zone, this home places Duval Street, Mallory Square, world-class dining, galleries, shopping, beaches, and iconic Key West landmarks just moments away. A rare opportunity to own a turnkey luxury compound in one of Key West's most coveted locations. Call today for a showing!

317 Whitehead St, Key West

$4,300,000

4 Beds ⋅ 5 Baths ⋅ 621463 MLS

There is a certain rhythm to life in Key West. Mornings begin outside, friends have a way of staying longer than planned, and some of the best evenings never make it past the backyard. 1614 Washington Street was designed for exactly that kind of life. Natural light, high ceilings, and an easy connection to the outdoors give the home an immediate sense of openness. The main living spaces flow naturally toward the pool and tropical garden, creating a setting that works just as well for a quiet morning at home as it does for dinner with friends that stretches late into the evening. The heated and chilled pool features two distinct levels--a shallow splash deck and a deeper swimming area--connected by cascading water features and surrounded by mature tropical landscaping that feels remarkably private. The floor plan understands that guests are part of island life, but privacy still matters. The first-floor primary suite creates a comfortable retreat for the owners, while upstairs, three en-suite bedrooms surround their own den and lounge. Family and friends can settle in, unpack, and have a space of their own rather than simply occupying yours. Behind that relaxed lifestyle is a house designed to make living here easier. Award-winning local architect Matthew Stratton brought together solid masonry construction, impact-rated windows and doors, solar power with Tesla battery storage, an EV charger, custom cabinetry, quartz surfaces, and thoughtful systems chosen for the realities of coastal living. The technology is there when you need it and nearly invisible when you don't. Morning walks, bike rides, the beach, neighborhood restaurants, galleries, and everything that makes Key West unlike anywhere else are simply part of the day. 1614 Washington invites you to open the doors, gather the people you love, jump in the pool, stay for dinner, and make yourself at home. Because ultimately, the best luxury isn't about having more. It's having a home that lets you live well.

1614 Washington St, Key West

$2,195,000

3 Beds ⋅ 2 Baths ⋅ 621461 MLS

Completed in 2025, this brand-new, elevated two-story home rises above the surrounding homes and is built above flood level. Excellent location close to the beach. Category 5 hurricane-rated construction, impact windows and doors, and Hardie board siding combine coastal style with storm protection. The home offers 3 bedrooms and 3 bathrooms, plus an office currently set up with bunk beds as a fourth sleeping space. Separate laundry room. The backyard is a gorgeous tropical retreat. A large heated pool and spa are surrounded by a gorgeous stone deck, lush landscaping and dramatic evening lighting. A huge poolside Tiki hut creates a spectacular setting for shaded dining, lounging and entertaining, while a putting green adds to the fun. Generous gathering areas and a completely fenced yard make this outdoor oasis perfect for sunny afternoons and unforgettable evenings beneath the palms. Inside, bright, open living and dining spaces flow into a beautiful kitchen with white cabinetry, stainless steel appliances, a blue tile backsplash and a generous island with seating. Balconies extend the living space outdoors. Beneath the home, a large covered area offers room to watch sports, relax and entertain, or serve as a carport. A permitted downstairs enclosure provides valuable storage and pool cabana. New construction, an elevated setting and an exceptional backyard come together in one remarkable property. Don't miss your opportunity to make this tropical escape your own!

1716 Laird St, Key West

Key West Homes with Metal Roof

Newest Key West Homes with Metal Roof