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Key West Homes for Sale, Single Family Houses, MLS Home Listings

Total Listings 236
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$3,295,000
Key West
Key West Investment Co Subdiv   - MM: 1.00
3 Bed, 3 Baths, 2,100 SqFt Days Listed: 185
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

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

$3,311,000
Key West
Investment Co Subdivision   - MM: 1.00
4 Bed, 4 Baths, 2,928 SqFt Days Listed: 348
-16.18% ($639,000) 3 Price Changes : Last Change 58 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Welcome to your dream oasis in the heart of Key West! This stunning 4-bedroom, 4-bathroom home embodies luxury and entertainment, offering an unparalleled lifestyle in a prime, central location on the island.Stepping through Brazilian-Walnut Entry doors into this exquisitely updated residence, you are captivated by the lush courtyard and lured over the Pond bridge to the sounds of cascading waterfalls. Massive Custom-made entry leads to an expansive grand foyer and open-concept living area, perfect for hosting gatherings or relaxing in style. The gourmet kitchen is a chefs delight, featuring top-of-the-line Viking gas-fueled appliances, custom cabinetry, and a large island with seating for casual dining. Adjacent to the kitchen, the elegant dining area features a unique white slate gas fireplace and flows seamlessly to the spacious living room, creating an ideal space for entertaining guests.Each of the four bedrooms is a private retreat, boasting generous proportions, and high-end finishes and furnishings. The primary suite is a true sanctuary, offering a spa-like bathroom with a soaking tub, walk-in shower, and dual vanities, as well as 2 walk-in closets.Outside, the home is a paradise for outdoor living. The meticulously landscaped backyard features a sparkling pool, joined by a spacious patio with plenty of room for lounging and alfresco dining. The covered terrace and outdoor kitchen are perfect for year-round entertaining, while the tropical lounging lawn provides a serene sunbathing escape.This luxurious home also includes modern amenities such as a state-of-the-art home automation system, new energy-efficient HVAC, and ample storage with TWO garages. With its unbeatable location in the heart of Key West, youll enjoy easy access to the islands vibrant nightlife, world-class dining, and stunning beaches.Offered completely furnished, you will experience the epitome of luxury living in this exceptional Key West home.

$3,395,000
Key West
Old Town Unlisted   - MM: 1.00
2 Bed, 2 Baths, 1,650 SqFt Days Listed: 48
-2.86% ($100,000) 1 Price Change : Last Change 10 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Welcome to your private oasis in the heart of Old Town Key West, where modern luxury meets historic charm. This beautifully renovated home perfectly blends timeless island architecture with sleek, contemporary comforts, offering an unparalleled living experience just steps from the Seaport and world-renowned Duval Street. Behind its classic facade, an airy, open floor plan awaits, thoughtfully designed for effortless indoor-outdoor living. Soaring vaulted ceilings crown the expansive living, dining, and kitchen space, where folding glass doors dissolve the boundaries between inside and out. The gourmet chefs kitchen features a premium Sub-Zero and Wolf appliance package, ideal for preparing island-inspired meals at home. Step outside to a lush backyard retreat anchored by a stunning saltwater pool--heated and chilled for year-round enjoyment--with a relaxing sun shelf, tranquil waterfall, and optional scupper cascades. A fully equipped poolside gazebo with a built-in grill, refrigerator, and ice maker invites unforgettable alfresco gatherings under the stars. The flexible layout includes two elegant bedroom suites and a versatile den with an adjacent full bath, perfect for guests or a home office. The first-floor primary suite offers a serene escape with a luxurious king bed and spa-inspired bath, while upstairs, a second bedroom shares a full bath and a convenient laundry area. Additional features enhance both comfort and value, including hurricane-rated windows and panels, roof certification, and a coveted X-flood zone location--offering significant savings on insurance costs. A private off-street parking space adds to the ease of island living. Tucked away on a quiet residential street yet just moments from the best of Key West, this exceptional home offers the rare opportunity to own a fully updated historic property in one of the islands most sought-after neighborhoods--where every day feels like a vacation, and every evening invites you to savor the sunset.

$3,499,000
Key West
Old Town Unrecord   - MM: 1.00
5 Bed, 5 Baths, 2,349 SqFt Days Listed: 4
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Exquisite Old Town residence just completed!Rare opportunity to own your Key West dream home designed to satisfy both peace of mind and self-indulging luxuries. This historic structure has been rebuilt from the foundation up to create the perfect harmony of historic restoration, structural integrity and custom design. Luxurious 5 bed/ 4 bath including a detached poolside cabana and off-street parking. An exceptional floor plan perfectly combines open concept living and defined spaces with attention to both function and elegance. Practice your culinary skills in a luxury kitchen with a high end appliance package to include Viking and Subzero. Delight in the perfect combination of indoor/outdoor living with custom door wall and sliders off bedrooms that lead to vast covered porches both up and down that cater to space for both dining and lounging Relax around the custom pool with sun shelf and waterfall or on the sunny poolside patio surrounded with tropical vegetation. Located in the X flood zone plus new roof and new impact windows/doors throughout lend itself to energy saving, sound proofing, insurance discounts and ease of ownership. An ideal combination of historic character,a modern floor plan, sprawling spaces and designer finishes await you in this Key West dream home!

$3,600,000
Key West
Old Town Unrecord   - MM: 1.00
3 Bed, 3 Baths, 1,890 SqFt Days Listed: 158
-7.57% ($295,000) 2 Price Changes : Last Change 45 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Impeccably preserved historic residence located in the heart of Old Town Key West. Discover the enticing charm of Key West and stroll through the majestic tree lined streets from 715 Frances Street. A rare combination of Key West luxury and historic architecture, this beautiful eyebrow home is perfectly positioned on a large spacious lot on sought after X Flood zone keeping you high and dry.Three beautifully appointed bedrooms, all ensuite upgraded bathrooms with a master on the ground floor and two bedrooms on second Floor.Recently completed 360 sq. ft. gazebo completes the property adding a stunning entertainers dream with outdoor kitchen, dining and seating area overlooking large saltwater pool, jacuzzi, and private garden.Gourmet kitchen finished with custom cabinetry, large countertops, gas Viking stove, Subzero appliances and glass chandeliers.Property is being sold turn key and is beautifully appointed with a stunning designer furniture package and interior plantation shutters.Additional features include full house generator, outdoor storage, off street parking for car and golf cart, outdoor shower, 2 new AC units and dehumidifier, new pool heater and chiller, new landscape lighting, new Ipe decking, Oolite stepping stones and bench, 3 new on-demand tankless hot water heaters, kevlar shutter package for entire house & 5 Camera security system.

$3,650,000
Key West
Gg Watson Subdivision   - MM: 1.00
5 Bed, 5 Baths, 2,721 SqFt Days Listed: 157
-18.89% ($850,000) 4 Price Changes : Last Change 9 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

X FLOOD ZONE! Luxurious Old Town Key West Oasis with separate Guest House! Nestled in the heart of Key Wests historic district, this impeccably remodeled property redefines island elegance. Situated in the coveted X Flood Zone, this home boasts an unparalleled location just steps from iconic Duval Street, world-class dining, vibrant galleries, and pristine beaches. Step inside to discover a light-filled sanctuary where 14-foot cathedral ceilings crown an expansive open-plan living, dining, and chefs kitchen area. French doors seamlessly blend indoor and outdoor living, inviting you to a private paradise. The spacious kitchen features Caesarstone Quartz countertops, a Sub-Zero refrigerator, a Wolf gas range, Fisher & Paykel double-drawer dishwasher, beverage drawers, and a microwave drawer. Outdoors, indulge in Key West living at its finest with a sparkling heated swimming pool, a large deck for entertaining and sunbathing, a serene waterfall, and lush tropical landscaping. A covered sitting area offers the perfect spot to unwind. There is a Sonos sound with Focal low-profile speakers to fill the air with your favorite tunes throughout the main house. The main house,1908 SF, features two guest rooms, a shared bathroom and a washer and dryer conveniently located between them, and a luxurious primary suite upstairs with its own washer and dryer. Impact windows and doors ensure peace of mind, while privacy fencing and off-street parking for two cars provide unmatched convenience. A super cute, separate guest house, 813 SF, completes this property, offering two ensuite bedrooms, a kitchenette, a dining area, and a loft sitting space--perfectly positioned at the back for ultimate guest privacy. A storage shed for pool toys and tools ensures everything has its place. This Key West masterpiece is a rare gem, blending timeless charm with modern luxury. Dont miss the chance to own your own slice of paradise! Easy to show! Video https://n9.cl/1114packer

$3,675,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 2,438 SqFt Days Listed: 104
-2.00% ($75,000) 1 Price Change : Last Change 3 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

This stunning Gingerbread-style home seamlessly blends historic charm with modern luxury right in the heart of Old Town . A covered wraparound porch welcomes you into a bright, window-lined foyer, leading to an elegant living and dining area. Throughout, gorgeous pine floors and walls highlight the homes timeless character.The open gourmet kitchen, featuring high-end appliances, flows into the living room and out to the covered loggia through vanishing pocket doors, creating seamless indoor-outdoor living. With 3 or 4 bedrooms, the main floor offers two en-suite bedrooms + a custom office, while upstairs, a spacious sitting room with a breakfast bar leads to the primary suite, complete with dual closets and a private balcony overlooking the heated pool and lush backyard.Designed for relaxation and entertaining, the large covered back porch offers serene views of the tropical landscaping and tranquil pool waterfall. A gazebo-style outdoor living space expands your backyard retreat and could easily convert back into a guest cottage as it once was.A rolling front gate, off-street parking, and a charming front porch perfect for people-watching complete this exceptional property.

$3,749,000
Key West
Tropical Bldt & Investment Co   - MM: 2.00
4 Bed, 4 Baths, 1,802 SqFt Days Listed: 609
-5.69% ($226,000) 2 Price Changes : Last Change 78 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

If you are looking for Key West Luxury Island living at its best, then here it is 1235 Washington St. Island modernization with ultra-luxury high end finishes. This newly renovated residence is built above the current base flood elevation and designed to the latest building codes. Home features 4bedrooms/4 bathrooms of unparalleled style & sophistication. Complete with designer kitchen, build in cabinetry from Italy, quartz counter tops, and high end appliances. Home is built with CBS construction, spray foam insulation, hurricane impact windows & doors, and V-crimp metal roof which will help lower insurances and provide low maintenance. Interior has 10 ft. ceilings throughout and a grand vaulted ceiling in the living room area. Brand new salt water pool with water feature and separate pool house/guest quarters designed with carefree life style adds to the exceptional value of this amazing home. Home is furnished with new modern furniture inside and out and is available for purchase but not included in purchase price. Sit on your super beautiful front porch with tiger wood finishes and enjoy all Key West has to offer. Home is located on a 5,348 S.F. corner lot in one of the most prestigious and desirable areas of Key West. Lush tropical landscaping, irrigation, outdoor lighting, and off St. Parking completes this very desirable luxury property. Just a short distance too many of Key West fine restaurants, galleries, museums, White St. pier, & beaches. Dont miss out on this excellent opportunity to own this impressive and newly renovated luxury residence at 1235 Washington St.

$3,750,000
Key West
Tropical Bldt & Investment Co   - MM: 2.00
4 Bed, 4 Baths, 2,585 SqFt Days Listed: 545
-5.06% ($200,000) 2 Price Changes : Last Change 117 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

BRAND NEW CONSTRUCTION. Four bedrooms, 4.5 bathrooms including guest quarters and pool. High end trim package includes Thermador appliances with wet bar, 58 bottle dual temperature wine cooler, beverage center, ice maker, induction stovetop. Upstairs and downstairs laundry. Riva European white oak wood flooring manufactured in Spain, white Thassos marble in primary first floor bath. Free standing bathtub in beautiful shower enclosure in second floor bath. Euro sliders that create a 16 foot opening to Ipe decking, oolite walking paths with crushed granite. Saltwater pool with all Pentair equipment, automation for heater/chiller, waterfall, LED lighting, 65K BTU multi speed pump. Remote controlled gate for secure off street parking and separate secure off street golf cart space. Lush landscaping with lighting and irrigation. Warranties still in place. Owner is Florida licensed real estate agent.

$3,795,000
Key West
Monroe Investement Co Subdivi   - MM: 2.00
4 Bed, 4 Baths, 2,628 SqFt Days Listed: 122
-4.53% ($180,000) 1 Price Change : Last Change 25 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

This British designer has spent over twenty years crafting contemporary properties in a luxurious Caribbean setting. Well-known for attention to detail and a commitment to sourcing the finest materials, this builders constructions are exceptional. The spacious living room effortlessly merges with the outdoors upon opening the storm-proof sliding doors, creating a seamless transition between interior and exterior space. The house features elegant tile floors throughout the first floor, while the second level is distinguished by luxurious hickory wood flooring. The dining room is tailored to accommodate a bespoke layout, complete with ambient mood lighting and refined cove molding. A a generously proportioned bedroom and bathroom, complete with private access to the pool area, are nestled at the rear of the first floor. This stunning four-bedroom, five-bathroom residence boasts an impressive 2,628 square feet of living space, set amidst a meticulously landscaped 5,600 square-foot lot. The masterful landscaping is the work of a renowned expert, celebrated for work on the most exclusive properties in the Florida Keys. The main bedroom of this stunning residence boasts a robust layout and sliding doors that open onto the upstairs balcony. The expansive wrap-around balcony also provides access to the two additional bedrooms, each featuring its own bathroom. The propertys reflective metal cool roof is engineered to optimize energy efficiency and provide year-round comfort. Moreover, three independent air conditioning units ensure a consistently cool environment. There is also a 500 gallon underground gas tank and a 2.2kw house generator. Additional features include off-street parking for multiple vehicles, a private driveway, and secure electronic gates and security camera system, solidifying this propertys reputation as a masterpiece of timeless craftsmanship. Once you step inside, its allure will undoubtedly capture your heart.

$3,799,000
Key West
Old Town Unrecord   - MM: 1.00
6 Bed, 6 Baths, 3,171 SqFt Days Listed: 172
-10.61% ($451,000) 6 Price Changes : Last Change 40 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Median - Dockage: None

Situated directly across from the iconic Ernest Hemingway House, this exceptional family compound combines the rich history of Old Town Key West with modern luxury and island charm. From the famous six-toed cats that roam next door to the vibrant energy of Duval Street just steps away, this location is as legendary as it is convenient. Spanning two addresses at 407 and 415 Olivia Street, this versatile property is situated in the X flood zone and offers four off-street parking spaces. The main house, a meticulously renovated mid-century modern gem, welcomes you with a grand entrance foyer that flows into a spacious living, dining, and media area. Perfect for entertaining, the space features a working fireplace and a 76-inch TV. The gourmet kitchen boasts solid wood cabinetry, Bosch and Thermador appliances, an induction cooktop, column fridge/freezer, wine cooler, and an impressive 13-foot quartz waterfall island. Impact sliding doors open to a stunning saltwater pool complete with a sun ledge, slide, and waterfall. Surrounded by tropical landscaping, this backyard oasis also features an outdoor shower, fully equipped kitchen, and plenty of space for entertaining. The main house offers four bedrooms, each with generous closet space and outdoor access. The primary bedroom includes a new custom walk-in closet with solid maple built-ins. Another ensuite bedroom has been transformed into a stylish home office with a built-in Murphy bed. The two additional bedrooms share an elegant bathroom featuring a luxurious soaking tub and shower. Adjacent to the main house is a charming two bedroom, two bath Conch-style cottage that provides the perfect guest retreat or mother-in-law suite. This home features a fully equipped kitchen, Dade County pine accent walls, and a tranquil outdoor space to relax under the shade of swaying palm trees. Dont miss the chance to see this unique compound that provides the perfect blend of history, luxury, and the ultimate Key West lifestyle!!

$3,799,000
Key West
Gwynn Subdivision   - MM: 1.00
5 Bed, 5 Baths, 2,960 SqFt Days Listed: 244
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Introducing Blu on White one of Key Wests most stunning historic single level residences in desirable Old Town Key West. Exceptional location scoring a full 10 on the walkability scale with easy access to the beaches, White St. Pier, an array of galleries, restaurants and cafes.Taking full advantage of the generous 5800 sq ft. lot, this 5BD/4BA home offers so much space and versatility with almost 3000 sq ft. of interior living space. Currently configured as a 4BD/3BA main house with a separate 1/1 apartment with private entrance. The apartment is perfect for a nanny, mother in law and also offers an excellent source of income as it comes with a transient license which will permit nightly rentals. Current owner operates the apartment as a nightly vacation rental and numbers can be provided upon request. The main house is currently being operated as a monthly vacation rental with a strong rental history and excellent future bookings, which will convey with the sale.Originally two historic shotgun homes, this home has been expertly merged to create a breathtaking great room addition that overlooks the stunning saltwater pool and garden. Featuring a high vaulted ceiling with post and beam design, wide plank wood floors, skylights for additional natural lighting, built-in bookshelves and large impressive impact sliders creating an enviable ambiance you will never want to leave.Prepare to be captivated by the heart of the home, the luxuriously appointed kitchen, crafted with the finest materials & unparalleled design, this culinary haven is perfect for any aspiring chef and those who love family gatherings, with gas Viking stove & appliances, European style open shelving, excellent prep space and large interior dining area. Additional features include oversized saltwater pool, private tropical landscaped garden and cozy shaded Gazebo, storage shed and so much more.The epitome of a fine Key West Historic Home combining luxury and versatility

$3,899,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 2,532 SqFt Days Listed: 17
-2.50% ($100,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Located in the heart of Old Town Key West, 316 Southard Street is a meticulously renovated single-family home that pairs modern comfort with classic Conch-style architecture. Originally built in 1938, the home has undergone a comprehensive renovation, blending timeless character with thoughtful, high-quality upgrades. Offering over 2,500 square feet of finished living space on a 6,165-square-foot lot, the residence features three bedrooms and three and a half bathrooms--well-proportioned for relaxed daily living and effortless entertaining. The ground-up renovation includes a new metal roof, all impact windows and doors, sound proofing in the walls, upgraded plumbing and electrical systems, a premium two zone HVAC installation, integrated indoor and outdoor sound system, and the addition of a custom-designed pool with integrated lighting and heating. The jaw dropping kitchen has a blend of the very best, from Wolf there is a gas stove, induction stove, steam oven, convection oven & microwave. Bertazzoni integrated refrigerator, freezer and wine fridge. Finally a top of the line Miele dishwasher rounds out the appliances. A thoughtfully designed rear addition, approved by the HARC, enhances both the function and flow of the home. Inside, historic elements are complemented by premium finishes, while outside, a partial wraparound porch, ample off-street parking, and color-adjustable smart lighting add both charm and convenience. The 12 x 24 pool and private yard create a quiet retreat, just steps from the vibrant energy of town. Positioned just blocks from the waterfront, restaurants, and cultural landmarks, this turnkey residence offers a rare opportunity to own a refined island home in one of Key Wests most coveted locations. *Seller is a licensed Florida realtor.

$3,995,000
Key West
Monroe Investement Co Subdivi   - MM: 2.00
4 Bed, 4 Baths, 2,806 SqFt Days Listed: 76
-10.10% ($449,000) 2 Price Changes : Last Change 14 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Rarely does a property captivate with environmental consciousness and uncompromising luxury, but 1614 Washington boldly achieves both. Now available at $3,995,000, this brand-new construction never-lived-in home in Key Wests sought-after luxury market, with 2,806 square feet of sustainable living that feels effortlessly sophisticated. The two-tiered cascading pool with splash deck is the centerpiece of your private tropical oasis, a sanctuary that redefines island living through thoughtful integration with nature. The heart of this home shines through its remarkable energy independence: solar infrastructure paired with Tesla battery storage ensures uninterrupted clean power even when grid systems fail. This isnt just a home; its a forward-thinking framework wrapped in architectural elegance. Inside, the owner-focused floor plan creates distinct zones for both entertaining and retreat. The open-concept main living area flows seamlessly from gourmet kitchen to dining to living spaces, while the private primary suite offers a peaceful escape. For guests, three additional en suite bedrooms connect to a versatile den and sophisticated coffee bar, perfect for multigenerational living or hosting visitors in style. Meticulous craftsmanship permeates every detail: custom cabinetry from local artisans Hansen and Bringle, hand-blown glass fixtures that cast mesmerizing light patterns, and a show-stopping backlit blue agate backsplash that serves as functional artwork. Environmentally friendly porcelain tile and premium quartz surfaces complement the homes sustainable spirit without sacrificing luxury. The comprehensive smart home system consolidates all electronics into one user-friendly hub, giving you fingertip control over your environment. Mature tropical landscaping creates privacy while enhancing the allure of outdoor living spaces. Schedule a private showing. This opportunity wont last, call for a private showing.

$3,999,000
Key West
Old Town Unlisted   - MM: 1.00
7 Bed, 7 Baths, 3,015 SqFt Days Listed: 161
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

This property has a glamourous three bedroom, three and a half bath owners unit with private pool and hot tub, plus three lucrative long-term rentals. It is the entire Lighthouse View Condominium Association, currently inactive. Enter thru the electric gate to a bricked courtyard with parking for several cars and many bicycles and access to a covered carport. The main residence with its heated pool and hot tub is secluded in the rear with a pretty garden and brick terrace. A free-standing two story building contains a great room, splendid kitchen and half bath downstairs. Above is a bright and breezy master suite with cathedral ceilings and skylight. In addition, there are two guest cottages, each with one bedroom, one bath and a pretty front porch. On the deck between the cottages is an outdoor wet bar and there is an outdoor shower by the pool. The other apartments are in a building at the front of the property. Downstairs are two one bedroom-one bath units. Upstairs is a glamorous two bedroom-one bath with a big, wonderful deck under the trees.

$4,200,000
Key West
Benj Alburys Subdivisiond   - MM: 2.00
4 Bed, 4 Baths, 2,177 SqFt Days Listed: 87
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Hidden behind a lush, tropical paradise on a coveted corner lot, 810 Eisenhower Drive is an extraordinary Victorian Estate built prior to 1912, seamlessly blending Old Towns rich history with modern luxury. This meticulously restored home showcases timeless Dade County Pine, original windows, a grand front door, and a striking newel post that echo the craftsmanship of a bygone era. Beyond the home itself, prepare to be captivated by the most breathtaking private garden in Key West, a botanical wonderland with meandering secret walkways, intimate lounging areas, and an array of exotic flora and towering palms, all nurtured by a full irrigation system. Inside, 2,177 square feet of impeccably designed living space awaits, featuring four spacious bedrooms, three full bathrooms, and two half bathrooms. The gourmet kitchen is a chefs paradise, boasting a BlueStar oven, Viking refrigerator, and custom cabinetry, while the expansive 27 x 12.5 loggia with soaring 15 ceilings and composite decking provides the ultimate shaded retreat. The backyard is a private oasis, complete with a Viking BBQ grill, Subzero ice maker, a stunning 30 x 15 saltwater heated pool, and elegant coral stone hardscaping. Thoughtfully designed for both luxury and convenience, this property features a full-house generator, a Lift Master electric carport with built-in storage, and zoned landscape lighting that transforms the grounds into a glowing paradise after sunset. Artful details abound, from copper exterior light fixtures to a Rick Worth-painted primary suite and a climate-controlled, 900-bottle wine room, while an outdoor shower adds the ultimate island-living touch. Sitting on an expansive 8,800-square-foot lot, this home offers an unparalleled level of privacy--a true world of its own in the heart of Key West. More than just a home, this is a once-in-a-lifetime opportunity to own a piece of Key West history, wrapped in the islands most awe-inspiring tropical garden.

$4,250,000
Key West
Webb Realty Co Subdivision   - MM: 1.00
5 Bed, 5 Baths, 2,681 SqFt Days Listed: 169
-9.57% ($449,999) 2 Price Changes : Last Change 5 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

This stunning home in Casa Marina is a complete restoration of the original historic structure. Just 5 blocks from Higgs Beach and 6 blocks from Duval Street this property has a large master bedroom and two guest bedrooms on the main floor all with private baths and their own entrances opening to over 900 square feet of wraparound porches. The wide entrance hallway has an additional 1/2 bath and opens up into the great room showcasing living, dining and kitchen space with soaring 20 foot ceiling and skylights. The hallway, kitchen and dining room walls are finished with Shiplap and all the floors throughout the home are a stunning custom stained Heart Pine reminiscent of the historic floors of Key West homes. The kitchen boasts a large island with sink & electrical connections as well as seating for 6; a wet bar, two pantries and a full Viking professional package round out the space. There is also a laundry room with a 1/2 bath that opens onto the back deck right next to the 15X8 pool with water feature. The Shiplap continues up the stairs to the interior balcony overlooking the great room and there are 2 additional bedrooms each with their own private baths and walk-in closets as well as a massive storage area that wraps an entire half of the second floor and is a finished and fully air conditioned space. All exterior doors are Mahogany impact with impact transoms and all windows are impact as well. Also, a 250 gallon propane tank is buried, hooked up to the gas stove & on demand water heater and is generator ready. There is 1 off street parking spot with electric gate. The home has been professionally landscaped and professionally furnished.

$4,250,000
Key West
Old Town Unrecord   - MM: 1.00
4 Bed, 4 Baths, 2,249 SqFt Days Listed: 74
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

An extraordinary opportunity to own a luxurious retreat in the heart of vibrant Old Town Key West. This exquisitely renovated 4BD/3BA estate masterfully blends island-contemporary elegance with timeless sophistication. Nestled on a rare double lot, it features soaring ceilings, a gracious open layout, and a private primary suite spanning the entire second floor. The chefs kitchen is a showpiece with custom cabinetry, quartz waterfall island, premium Thermador appliances, and hurricane-rated nano door opening to a lush tropical sanctuary. Outdoor living is elevated with alfresco kitchen, motorized pergola, resort-style pool with water feature, and a spacious new guest cottage. Designer finishes, hardwood floors, new bathrooms, HVAC, outdoor shower, and off-street parking complete this unparalleled offering.

$4,295,000
Key West
W C Maloney Diagram   - MM: 2.00
5 Bed, 5 Baths, 3,300 SqFt Days Listed: 195
-21.84% ($1,200,000) 4 Price Changes : Last Change 60 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Built in 1943, and Originally owned within the Singleton Estate, 1319 Olivia St. is more than just a home, its a legacy, embodying beauty, elegance and history at every turn.Ideally located within the heart of the meadows, this Historic Grand Dame is one of the most impressive homes in Key West today, known for its stunning architecture and superb craftsmanship.Both kitchen and living rooms flow out to an abundant outdoor area, featuring a large covered Gazebo, saltwater pool, deck and impressive garden allowing a wonderful setting for large scale entertaining or intimate gatherings. Meandering gardens with mature fruit trees and dozens of blooming orchids with wrap around porches and roof-top decks offer many ways to enjoy the home.With 5 bedrooms and three full Bathrooms, three floors and a new master suite with stunning marble bathroom, Olivia has room for a large family with 3300 Sq Ft. interior space and situated on an enviable sizable 7800 sq ft. lot.Dade County Pine floors and walls throughout, wrap-around porches, french doors, marble bathrooms, elevated and built to last, this home is sure to leave a lasting impression with a longing for more.Permanent carport offers covered off street parking with additional street parking available. A must see for any buyer looking for the ultimate Key West home.

$4,400,000
Key West
Key West Fwdn Subdivision   - MM: 4.00
3 Bed, 3 Baths, 2,744 SqFt Days Listed: 195
-2.22% ($100,000) 1 Price Change : Last Change 80 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

3741 Eagle Avenue - A Masterpiece of Coastal Luxury This stunning 3 bedroom, 3.5 bath fully furnished residence on a generous 10,800 SF lot offers unparalleled coastal elegance at an impressive elevation of 10.5ft. The new concrete construction features an open concept with cathedral ceilings and large impact sliding doors throughout. Premium materials, high-end appliances, and thoughtful layout create both functionality and sophistication.Two en-suite primary bedrooms, both upstairs and downstairs, open to the outdoors. The property includes a fully equipped guest cottage featuring sliding doors that offer stunning views. The grounds, masterfully designed by Craig Reynolds, showcase lush tropical landscaping, covered patios all surrounding a heated/chilled pool with shelf seating and a distinctive coral rock outdoor shower which adds a luxurious touch. The garage provides 481 square foot for parking and ample storage.Security and comfort are ensured with a whole-house Generac generator, standing seam metal roof, impact windows and doors. Every detail of this turnkey residence has been executed to perfection, creating an extraordinary Keys retreat.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 06-15-2025.
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