Extraordinary home in the historic district! Enjoy Key West living in the prized Old Town neighborhood with the perfect combination of all the top sought after attributes requested by buyers: walkable location, swimming pool, & private parking without compromise.Offered entirely furnished, the 3 bedroom and 3 bath home is absolutely move-in ready, prepared for your immediate occupancy. With over

Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

1420 Whalton Street is a masterfully engineered luxury residence where elevated construction, refined design, and resort-style amenities converge in one of Key West's most desirable residential neighborhoods.Built by Shaw Construction in 2023 with Insulated Concrete Form (ICF) construction and reinforced rebar, the home offers exceptional structural integrity, energy efficiency, and prepped for

Scott Forman Royal Palms Realty (KW)

Tucked behind a new privacy fence, 1706 Seminary Street is a fully renovated home where thoughtful design meets laid back Key West living. Set on a generous 7,480 square foot lot, this 3 bedroom, 3 bathroom home, with 2 en suite bedrooms, offers nearly 2,000 square feet of interior space that has been completely reimagined for easy island living with all the modern updates already done for you.

Ted Stewart Truman & Co. (KW)

Welcome to your dream coastal retreat! Perched on concrete stilts with sweeping views, this newer 4-bedroom, 3-bath luxury home offers the perfect blend of island elegance and modern comfort. Two spacious master suites provide privacy and flexibility, while the open-concept living space is framed by wide, breezy balconies -- ideal for soaking in the sunrise or entertaining guests in true Keys

Alejandro Perez Amerifirst Realty

Centrally located in flood X zone of Old Town, this 2-bed, 2-bath townhouse is classic Key West charm at its best. The galley kitchen offers abundant cabinetry, granite countertops, and stainless-steel appliances. High ceilings with wood-finished crown molding add warmth and character throughout. The spacious primary suite showcases beautiful Dade County pine and a private en-suite bath. Central

Brenda Donnelly Brenda Donnelly Real Estate LLC

Nestled in the heart of Key West's historic district, 616 Eaton Street is a testament to quality, timeless beauty, and refined living. This single-family residence was constructed in 1911 and painstakingly renovated and reimagined over the last few years culminating in 2024 with the spectacular like new home. Most hidden from the Street, it exudes classic Key West architecture blended with modern

Terri Spottswood Truman & Co. (KW)

''A turnkey retreat designed for comfort, connection, and carefree living just minutes from the beach.''Discover serenity in this elevated 3-bedroom, 3-bath Key West retreat, built in 2013, including modern impact doors and windows. The thoughtful two-story design features a convenient first-floor bedroom and two upstairs en suite bedrooms, each opening to private balconies for morning coffee or

Elizabeth Chamberlain Truman & Co. (KW)

A Tropical Sanctuary just 15 miles from Key West, 77 Bay Drive is where open water, flawless design, and island soul come together in perfect harmony. Perched along the edge of the Atlantic, this reimagined residence offers panoramic sunrise views, direct boating access, and a lifestyle most only dream about. Step through the door and into a home that's been transformed from top to bottom, with

Leigh Ann Roach Berkshire Hathaway HomeServices Knight & Gardner Realty

Looking for a gorgeous, lock and go, 2-bedroom condo in a perfect downtown Key West location? Just 1 1/2 blocks from Duval, on iconic Fleming Street, sits your dream Key West escape in the historic Campbell Building. This condo is gorgeous and its location can't be beat! A stone's throw from the action and the historic Seaport District, unit 4 is fully remodeled and looks directly down onto

Dawn Gonet Berkshire Hathaway HomeServices Knight & Gardner Realty

This elevated above flood 4/3 is renovated throughout and move in ready. Located on one of the most desirable streets in the luxury Key Haven community just minutes from Key West. The home is solid concrete and has 10' ceilings on both floors. There are large dual master suites on the second floor, one with freestanding tub. The home has a metal roof and two central AC's. There is plenty of off

Deborah Batty Location 3 Real Estate of KW Inc (KW)

The wait for perfection has concluded at 1314 Johnson Street. Brand new and never lived in, this pristine masterpiece is where architectural integrity meets the effortless spirit of the Key West lifestyle. Situated just two blocks from the iconic Casa Marina Resort and the beautiful sands of Higgs Beach, this residence offers a rare combination of 3,400 square feet of sophisticated interior

Brenda Donnelly Brenda Donnelly Real Estate LLC

Stunning open water views from this fabulous waterfront home! A truly rare and highly coveted 37,139 sqft lot point lot with A massive 362 FT OF WATERFRONTAGE on prestigious Sugarloaf Key, offering breathtaking panoramic open water views, exceptional privacy, and unmatched boating access. (24,662 sqft Upland & 12,477 submerged). These point lots are extremely limited and among the most

Lisa Swanson The Agency Florida Keys

Tucked discreetly behind one of Old Town's most storied addresses, 419 Simonton Street C is a hidden gem insiders hope no one else discovers. Completed in 2026 as a brand-new, ground-up construction, this private 2BD/2.5BA residence delivers modern island luxury within a lush, secluded enclave, featuring soaring cathedral ceilings in the bedrooms, impact-rated windows and doors, and a streamlined

Team Kaufelt Truman & Co. (KW)

Remarks - Consumer:Located in the highly regarded Casa Marina neighborhood, this exceptional property offers a unique opportunity to own a piece of Key West history. Ernest Hemingway the iconic literary figure once called this house his Winter retreat during 1928 -1929, where he penned the timeless classic, 'A FAREWELL TO ARMS.'' This sprawling single story property spans an impressive 8100

Key West Luxury Finders Preferred Properties (KW)

Rare Direct Oceanview 3BD/2BA Condominium located in The La Brisa community. This condo offers stunning ocean views just steps away from Smathers Beach. This spacious 3-bedroom, 2-bath condo offers sweeping views of the Atlantic Ocean and the sparkling turquoise waters that Key West is known for! Perfect as a full-time residence, winter home, or high-demand vacation rental, Unit 208E combines

Ruth Herdan Truman & Co. (KW)

New 2025 waterfront construction on the final canal in Key Haven--an architectural entertainer designed for seamless indoor-outdoor living just 5 minutes from Key West. Unlike typical Keys homes, this residence was designed around outdoor living, offering over 2,400 Sq.Ft. of covered entertaining space seamlessly connected to the interior. Completed in 2025, this striking modern waterfront

Lisa Swanson The Agency Florida Keys

Charming Home in the Meadows, Old Town, Key West. This beautiful completely renovated one bedroom cottage on Pearl Street is move in ready, and is being sold furnished. Stepping into the home through the custom built Dutch-door, the interior is bright, the walls are shadow-gap wood, there is new flooring, and recessed LED lighting throughout. The Bedroom has a murphy bed, and built in bedroom

Elaine Coyle Keller Williams Key West Compass Realty

Island Life, unequalled waterfront sunsets, ocean breezes and crystal clear waters. And you can drive to your Caribbean Island Escape! This location is exceptional on all fronts, more than 2X the avg lot size, a craftsman remodeled 3/2 converted to a 2/2 with a spacious convertible home office, gorgeous high quality materials throughout, including Walnut Engineered Flooring, Brazilian Quartzite

Stephanie Wise Keller Williams Key West Compass Realty

Tucked along the edge of the enchanting Butterfly Garden, this charming townhouse offers the perfect blend of privacy, tropical beauty, and resort-style amenities. Located within the gated community surrounding the Rees-Jones 18-hole Championship Golf Course, this home is a serene slice of paradise.Inside, you'll find thoughtfully designed living space featuring two upstairs bedrooms and 1.5

Stephanie Wise Keller Williams Key West Compass Realty

Welcome to 3446 Riviera Drive, a TRIPLE LOT, canal front estate w/ 104 ft of water frontage. Exceptional opportunity to buy into the coveted Riviera community w/ a 3124 sf pool home & almost 14,000 sf land. 4 bed/ 3 full bath main house, one level living (2536 SF) w/ rare 350 sf garage. Covered porch overlooks the peaceful canal. Living areas have magnificent light as sun moves across the back

Dawn Gonet Berkshire Hathaway HomeServices Knight & Gardner Realty

Updated home with a bright floor plan featuring quartz counter tops, stainless steel appliances, luxury vinyl flooring, and wraparound windows with remote control blinds. Spacious primary suite with walk-in closet, ductless zoned A/C, and French doors to wraparound screened patio that's 612 sq. ft. Heated 13x7 swim spa with outdoor seating. Concrete, elevated for lower insurance, insulated

Shirley Carey Berkshire Hathaway HomeServices Knight & Gardner Realty

Excellent opportunity to purchase a luxurious, modern, and refined single family home in one of the best neighborhoods in Key West. This 4bed/3bath completely renovated and modern home is being offered completely furnished with all new furniture and ready for new owners. Just over 1930 S.F. of beautiful living spaceand situated on a 5,896 S. F. corner lot. This CBS home has all hurricane impact

Jason Barroso Century 21 All Keys Inc (KW)

Open House March 15 1-3pm. Look no further! Beautiful Key Haven home! Spacious 4 bedroom, 3.5 bathroom canal front home located only 4 miles from Key West. This property offers a flexible floor plan, multiple gathering areas, and a comfortable layout for family living or entertaining. Enjoy direct boating access from your backyard canal and the convenience of a 60 ft dock. Recent updates include

Maria Wilson Berkshire Hathaway HomeServices Knight & Gardner Realty

Welcome to your perfect Island Escape! Nestled in the heart of old town, this beautiful home is one you're sure to fall in love with. Featuring two off-street parking spaces and a private pool, it blends luxury, comfort, and convenience, perfect for both vacation getaways and year-round living. Inside, you'll find three spacious bedrooms and three modern bathrooms, designed to provide everything

Andy Birrell Berkshire Hathaway HomeServices Knight & Gardner Realty

Excellent Family Home or Investment Opportunity! Step into your new life in this beautifully elevated three-bedroom, two-bathroom home featuring new impact doors and windows, a for-year-old AC system, new kitchen, and a newer roof (only three years old with two years of warranty remaining). Bright and airy, the main floor is filled with natural light and positive energy, offering a spacious

Yulia Vakhtenko Keys Top Realty LLC

Welcome to your slice of Lower Keys paradise--just 17 miles from Key West yet worlds away from the hustle. This elevated 2-bedroom, 2-bath home sits on a generous lot in a fantastic neighborhood, offering the perfect blend of comfort, style, and island living.Inside, vaulted ceilings and impact windows fill the home with natural light and breezy tropical charm. An elevator makes access

Stephanie Wise Keller Williams Key West Compass Realty

Welcome to your ideal island escape at 1607 Sunshine Drive in vibrant Key West, FL! This newer-construction 2014 single-family home offers the modern coastal lifestyle you want - built to the latest building codes for improved insurance options- featuring impact glass windows and doors, metal roof, concrete siding, and an elevated structure above base flood for added peace of mind.Step inside to

Jimmy Lane Island Life Realty Experts

The ultimate lock-and-leave Key West retreat awaits in the heart of Old Town! Perfect for those seeking a low-maintenance getaway this residence offers effortless luxury living and the convenience of a fly-in, fly-out lifestyle.Located on exclusive Admirals Lane within the award-winning TRUMAN ANNEX, this is the LARGEST townhouse in the annex. The home features soaring 10-foot ceilings on all

Lisa Swanson The Agency Florida Keys

The rare kind of antiquity that comes with all the comforts of today. Built before 1889 and reimagined for modern living, 419 Simonton Street A captures the true spirit of Old Town Key West--authentic, refined, and timeless. Once a mixed-use landmark with a flower shop below and a residence above, the home has been meticulously restored and reimagined from the ground up, with construction

Team Kaufelt Truman & Co. (KW)

BRAND NEW CONSTRUCTION! PLUS - Location, Location, Location! This 4-bedroom, 2-bathroom home is just two blocks from Old Town's vibrant center, Duval Street, the Southernmost Point and the beaches. Plenty of off-street parking with room for FIVE cars PLUS an oversized pool. With these amenities, location and BRAND NEW construction, this house should not be missed!

Danny Sanchez Century 21 All Keys Inc (KW)

There are streets in Old Town that everyone knows, and then there are streets like Elgin Lane that most people never even realize exist. Quiet, tucked away, and remarkably private, this hidden lane offers what buyers search for endlessly in Old Town privacy, off street parking, and a pool, all in one of the most desirable locations in Key West. 1116 Elgin Lane is a 3 bedroom, 2 bath home located

The Spottswood Team Truman & Co. (KW)

Meticulously renovated 1866 Conch Revival perched atop Solaris Hill in the heart of Old Town and Steps from Old Town's vibrant culture, dining, and entertainment. This historic gem blends rich heritage with contemporary comforts offering an open Floor plan, 2 primary bedroom options (one on first level), X Flood Zone, cocktail pool, hammock porch and more! Step into the foyer at the corner of

Kimberley Haley Brenda Donnelly Real Estate LLC

MOTIVATED SELLERS! Exceptional Old Town estate with pool, gardens, and 2 guest houses in the heart of Key West. This impeccable property blends timeless architecture with modern updates across three beautifully appointed structures. Behind a privacy wall & gate, the estate includes a grand main residence and two guest houses (both with kitchenettes), offering a total of four bedrooms and

Terri Spottswood Truman & Co. (KW)