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

Total Listings 265
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$3,100,000
Key West
Monroe Investement Co Subdivi   - MM: 2.00
5 Bed, 5 Baths, 2,711 SqFt Days Listed: 196
-6.06% ($200,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Stately Key West home has undergone a stunning renovation but maintains classic Keys charm with a beautiful wood staircase, stained glass window and transom, Dade County pine walls, and wraparound porches on both levels. Centrally located in Key West this home is the perfect island residence with POOL! The main level offers plenty of room for entertaining with large spaces for conversation, dining, games, cooking, and more. Spacious chefs kitchen with breakfast bar and natural design elements throughout. Kitchen flows to the sitting area with designer bar space and wall of sliding glass doors opening to the pool and a pass-through window to covered porch area. Main level offers one bedroom with outdoor access and a full bath. The upper level boasts four additional bedrooms including primary suite. The primary bedroom is a resort like retreat with elegant spa tub, large walk-in shower with multi-jets, rain forest shower, linear drain and walk-in closet. The primary also features access to deck space perfect for morning coffee. Bedroom with en suite bath and deck access. The other upstairs two bedrooms share an en suite full bath. Perfect tree top views from upstairs on the wraparound porch. The third level is currently a music room and offers access to the widows walk for top of the island views! Lovely private outdoor areas with mature tropical landscape. Pool area with tiki hut offers covered space for reading or relaxing. Garage has room for parking or storing your island water toys. Laundry room on second floor and bonus washer & dryer in garage. Elevator to each floor. Central AC. This is the perfect island home!

$3,141,000
Key West
Riviera Shores   - MM: 3.00
3 Bed, 3 Baths, 2,386 SqFt Days Listed: 69
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 58ft.Concrete

Your Dream Waterfront Oasis Awaits! Immerse yourself in refined elegance in this 3-bedroom, 4-bathroom sanctuary. The crown jewel of this residence is the unparalleled canal frontage, complete with a new 24k lb boat lift and ~58 of new seawall, offering seamless ocean access. Step inside to experience the spacious living areas, illuminated by tons of natural light, with tile flooring throughout. Marvel at the attention to detail in the updated kitchen featuring a waterfall island and all new stainless steel appliances. Outside, a heated salt pool, equipped with automation and a water feature, invites you to unwind amidst the lush turf and enchanting landscape lighting. Relish in unparalleled privacy with a comprehensive privacy wall and fencing, enhanced by a Mosquito Nix system for a pleasant outdoor experience. Enjoy the added conveniences of a whole-house automatic generator and on-demand gas water heater. Nestled in an environment that offers the best waterfront living, your lifestyle is enhanced by limitless opportunities for boating and fishing--right from your backyard: automatic front gates, circular driveway, and awning-covered parking round out this unparalleled offering. Elevate your life with this matchless blend of luxury and oceanic freedom!

$3,150,000
Key West
New Town Unrecord   - MM: 3.00
5 Bed, 5 Baths, 3,105 SqFt Days Listed: 84
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Expect the unexpected at 1400 1st Street, an exquisite retreat where unmatched craftsmanship meets island luxury. This custom-built 5-bedroom, 4-bathroom home offers a perfect balance of sophistication and quality. From the moment you step inside, the rich Brazilian cherry floors guide you through this elegant home, exuding warmth and elegance The chefs kitchen is a culinary dream, featuring polished granite countertops and top-of-the-line stainless steel appliances, including a Sub-Zero refrigerator and a six-burner Viking gas range. Custom tile work adorns each bathroom, elevating every space with exceptional detail.Soaring ceilings enhance the open-concept design, filling the home with natural light. Every poolside bedroom boasts its own private balcony, offering stunning views of the tropical surroundings. The expansive primary suite is a true retreat, featuring a private beverage center for added luxury and convenience. The spa-inspired primary bath includes a soaking tub and rain shower, creating an intimate oasis within your own home.Designed for effortless entertaining, the custom bar area is a true highlight. Equipped with a wine cooler, sink, and ice maker, its ideal for hosting memorable gatherings. Step outside into your private tropical oasis, where mature trees create a sense of serenity and two cascading waterfalls frame the serene swimming lagoon. A beautiful dining gazebo spans the water, perfect for outdoor dining and entertaining. Lush landscaping surrounds the entire property, providing privacy and an idyllic backdrop for relaxation.This home also includes a rare two-car garage, with secure parking for up to three additional vehicles or watercraft, offering unparalleled convenience. With its seamless blend of design, luxury, and functionality, this home is a true Key West gem.Just moments from the islands beaches, marinas, dining, and shopping, this property offers both tranquility and access to all that Key West has to offer!

$3,195,000
Key West
Martello Towers   - MM: 1.00
4 Bed, 4 Baths, 2,147 SqFt Days Listed: 123
-5.89% ($200,000) 2 Price Changes : Last Change 59 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

1522 Georgia St., a stunning retreat that captures the iconic charm of Key West with a modern twist, offering a lifestyle of unparalleled luxury. Located one block from the islands beaches and Casa Marina District, this newly built residence is a perfect combination of timeless island elegance & contemporary sophistication.Four exceptional bedrooms, each a private sanctuary of comfort and style, boast spa-like en-suite bathrooms and spacious walk-in closets. Wrapped in a palette of serene, calming hues, these retreats are adorned with elegant Eastern Accent Linens, gorgeous window treatments and handcrafted wood shutters that invite the Island breeze. Stunning wallpaper, worthy of an Architectural Digest spread, adds a touch of artistry to every space, creating bedrooms that feel less like rooms and more like luxurious personal havens.Open floor plan where indoor and outdoor living blend effortlessly, creating a space for relaxation and entertaining alike. The gourmet kitchen, elegant dining area and inviting living rooms flow together with ease, all offering panoramic views of the majestic saltwater pool. Outside a serene waterfall cascades into the crystal-clear waters, while the sun drenched patio, glass railing and mature landscaping provide a private, resort-like escape - a true oasis where every days feels like a vacation.The Kitchen is nothing short of breathtaking, a masterpiece of design and function where every details has been meticulously curated. The designers eye for perfection is evident in the harmonious blend of colors, textures and finishes, all layered with stunning precision. At its heart, a spacious, statement-making Island invites both conversation and culinary creativity. Overhead, brass-covered light fixtures cast a warm inviting glow, perfectly complementing the gorgeous artful backsplash that adds that final touch.Additional features include, impact windows/patio doors, & off street parking.

$3,249,999
Key West
Benj Alburys Subdivisiond   - MM: 2.00
3 Bed, 3 Baths, 2,033 SqFt Days Listed: 12
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Behind the gates of this nearly 5,000 sq ft lot in The Meadows awaits a refined Key West retreat offering comfort, privacy, and seamless indoor-outdoor living. This charming residence features 3 bedrooms, 2.5 baths, and just over 2,000 sq ft of living space, surrounded by lush tropical landscaping.The main living area impresses with vaulted ceilings and three sets of French doors that open onto a covered outdoor dining area beside a 300 sq ft pool--ideal for entertaining or quiet relaxation. The kitchen is well-appointed with quartz countertops, custom cabinetry, a butlers pantry, and a full wet bar. Premium appliances include a Viking and Wolf stainless steel appliances.The spacious primary suite, located on the first floor, is filled with natural light and offers double French doors, crown molding, custom built-ins, a walk-in closet, and an adjoining office. Upstairs are two guest bedrooms, each with in-room vanity basins and a shared full bath.IPE decking wraps around the home, providing approximately 2,000 sq ft of outdoor space for lounging and gatherings. Located just blocks from Duval Street and the Historic Seaport, with convenient access to New Town, this property blends classic Key West character with modern livability.

$3,250,000
Key West
Monroe Investement Co Subdivi   - MM: 2.00
5 Bed, 5 Baths, 2,500 SqFt Days Listed: 112
-2.99% ($100,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Discover an incredible opportunity in the heart of Key West! This 7,500 sq. ft. lot is cleared, ready for the new construction of this single-family home. Planned for a 5 bed, 5 1/2 bath, pool home. Buyer still has time to choose design materials and possible floor plan changes . Soaring ceilings on both levels, crown molding, and a full ensuite bath in every bedroom. The open-concept first floor is perfect for entertaining, with a spacious kitchen boasting a large island, white 42 cabinetry, and high-end appliances. The living area flows seamlessly into the kitchen and beautifully landscaped backyard with a pool w/hot tub. The second-floor laundry room includes ample cabinet storage, and the home is raised on piers above flood zone, with several private parking spaces. The first-floor primary suite features a walk-in closet and an ensuite with a 5 shower, double sinks, and a separate whirlpool tub. Built to the highest wind load and flood standards, this home is both a sanctuary and a fortress. Contact agent about this New Build home! Photos are not exact and just an estimated of the new build.

$3,275,000
Key West
Webb Realty Co Subdivision   - MM: 1.00
3 Bed, 3 Baths, 3,049 SqFt Days Listed: 432
-9.00% ($324,000) 1 Price Change : Last Change 101 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Wonderful 3BD/3.5BA home with just over 3,000 sf of living space situated in the desirable Casa Marina neighborhood. Centrally located & just a short walk to Duval Street, the beaches, museums, galleries & many of Key West fine dining that it has to offer. With a spacious open floor plan & lots of windows & French doors throughout allow for plenty of natural light to fill this spectacular home. The master bathroom was recently renovated, a whole home generator was installed, a commercial on demand hot water heater was installed, new copper gutters and downspouts, newer Central A/C systems, downstairs interior was re-painted, composite decking on the exterior & a new carport canopy are all just some of the many great features this property has to offer. The kitchen has stainless appliances and the flooring throughout the downstairs & patio was replaced. Located just off the kitchen through the French doors you will find a large loggia which is an incredible space for your outdoor living & dining room where you can host family or friends comfortably. Upstairs you will find the master bedroom w/ ensuite bath and the 2 additional guest bedrooms. Off the master bedroom is a gorgeous & private sundeck which also has access to the pool deck via a spiral staircase. Additionally you can find stained glass throughout the home and cathedral ceilings. Property is located in the X Flood Zone and is completely fenced adding for that extra privacy. Potential for a great monthly vacation rental!

$3,295,000
Key West
Key West Investment Co Subdiv   - MM: 1.00
3 Bed, 3 Baths, 2,100 SqFt Days Listed: 186
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: 349
-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: 49
-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: 5
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: 159
-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: 158
-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: 105
-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: 610
-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: 546
-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: 123
-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: 173
-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: 245
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

$3,850,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 2,532 SqFt Days Listed: 18
-3.73% ($149,000) 2 Price Changes : Last Change 1 Day 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.

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 06-16-2025.
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