A Rare Investment Opportunity in the Heart of Old Town Key West. NIGHTLY rentals allowed. Introducing The Watson House—one of the largest and most versatile TRANSIENTLY licensed estates in Key West. Situated just one block off Duval Street on iconic Simonton Street, this 11-bedroom, 11-bath compound spans two distinct residences: a stately 7-bedroom mansion and a sleek, modern 4-bedroom villa—each with its own private pool. Zoned with two transient licenses and off-street parking for 4+ vehicles, this exceptional property offers unmatched flexibility for luxury rentals or private use. The grand mansion was reimagined in July 2022 by a local designer, featuring fresh paint, stylish new furnishings, and 12-foot soaring ceilings. The main level includes two guest rooms with baths, formal living and dining rooms, a parlor, and a well-appointed kitchen that opens to the pool deck and outdoor dining area. Upstairs, four en suite bedrooms include two primary suites with private balconies—one overlooking Simonton Street, the other with views of the pool. A spacious third-floor suite, accessed via an interior or exterior staircase, offers a private living room, wet bar, and yet another balcony retreat. The villa, renovated to the studs in 2014, offers a clean, contemporary design with 4 bedrooms, 4 baths, full kitchen, living area, private pool, and outdoor bar—perfect for entertaining. Whether you choose to rent the estate in its entirety or as two separate homes, The Watson House is a rare asset in Key West's luxury rental market—highly sought-after and consistently booked well in advance.
Enjoy your tropical retreat in the heart of Old Town Key West with this stunning, fully remodeled, three-story corner lot island oasis. The first floor of this expansive attached home welcomes you with soaring vaulted ceilings, an open floor plan drenched in natural light, and seamless indoor-outdoor living. Throw open the French doors and lounge on your poolside veranda, or take a dip in the perfect pool that invites you to unwind, entertain, and soak in the sunshine. Inside, the custom-designed kitchen is a chef's dream: smart technology appliances, touch-operated faucets, dual ovens (one with an air fryer), a warming drawer, soft-close drawers, built-in wine rack, liquor dispenser, trash compactor with recycling system, and even an ice machine—all wrapped in a layout designed for convenience and elegance. The living room exudes charm with stunning glass doors salvaged from the historic Casa Marina Resort, flooding the space with warm Key West light. Belt-driven ceiling fans and a hand-crafted octopus sink in the half bath add an artistic, whimsical touch that sets this home apart. Upstairs, the second floor features two spacious bedrooms with private bathrooms, ample storage, and a breezy balcony that overlooks the sparkling pool and sun deck below. Travel via stairs or your private elevator. The third floor houses an ideal office ,bed room, artist's studio, complete with a half bath, and access to the spectacular Widow's Walk—where panoramic rooftop views showcase the very best of Key West's tropical beauty. With three bedrooms, 3 full bathrooms, (2 inside and 1 outside) 2 half bathrooms, off-street parking, and no renovation needed, and even all the furniture conveys this home is truly turn-key. Stylishly curated with comfort and character in mind, it's the dream escape you've been waiting for. Paradise found—schedule your private showing today!
Incredible chance to own a premier slip in the private/gated Sunset Marina. Located at the end of the Sailfish pier, this 50' by 20' slip allows stress free docking and direct open water access for a wide range of boats. The slip is equipped with its own metered water, electric, and a lockable dock box to store items. HOA fees cover access to parking, the heated pool, spa, and clubhouse. In the marina is a fuel dock and a convenience store for all your boating essentials. Located conveniently for quick access to the Gulf and the Atlantic with a short ride. No liveaboards permitted.
Unique opportunity for a creative buyer to own this 3 residential unit property. Would be a great for business owner looking for employee housing. Update all 3 homes for a family compound. Currently setup as roommate style living with a gross income of $15,000. a month. Don't miss this great location in Bahama Village steps from the Truman Waterfront, Ft. Zach beach, restaurants, galleries, shops and more!
Coastal Living at Its Finest - 2-Bedroom Condo at La Brisa ! Wake up to ocean breezes in this beautifully appointed 2-bedroom, 2-bathroom condo located just steps from Smathers beach. Situated directly across the street from the shoreline, this bright and airy residence offers the perfect blend of comfort, convenience, and coastal charm. Inside, you'll find a spacious open-concept living and dining area filled with natural light, a modern kitchen , and two generously sized bedrooms with ample closet space. The primary suite features a private en-suite bathroom, while the second bedroom is ideal for guests or a home office. Relax on your private balcony with peaceful Salt Pond views, or take a short stroll across the street to sink your toes in the sand. This condo also offers amenities such as assigned parking, in-unit laundry, and access to a community pool, tennis courts and clubhouse. Perfect as a primary residence, weekend retreat, or investment property—this is beachside living made easy! Call for your private tour today !
Courtesy: Berkshire Hathaway Florida Realty
561-742-4700
LIVEABOARD Houseboat & Slip (Package) at Garrison Bight Marina (Houseboat Row). It's a Leasehold to the City of Key West and with the Transfer of Title to your name. NO RENTALS, VRBO/AIRBNB! This community is Historic. It's a TRUE KEY WEST LIFESTYLE... CASH ONLY! If your ready to enjoy life and have a crash pad in the Florida Keys, then come and see this one. Absolutely adorable. This community has no public pool.
BEST PRICE and LOCATION for a three bedroom home in the Sanctuary at the Key West Golf Club! New impact windows and doors! This charming single family home is ready for immediate occupancy. Featuring 3 bedrooms, 2.5 baths and gorgeous first floor open floor plan. Enjoy the large rear covered deck over looking the private pool and fully fenced in yard. Upstairs is the primary bedroom ensuite, two guest bedrooms and another full bath. All bedrooms feature vaulted ceilings and covered porches. Off-street parking for 2 vehicles in your own carport. Very easy to show! Owner is a Florida REALTOR. Easy to show!
Take a look at this picture perfect townhouse located in the prestigious Truman Annex . Nice end unit located just off Southard St is in excellent condition with many renovations throughout the house. Kitchen has been nicely updated with stainless steel appliances, custom cabinetry and granite countertops. Bamboo flooring throughout the first level leads to a cozy back brick patio and the convenient entrance to Southard St. Both bedrooms upstairs have bathrooms that are ensuite. There are porches (one covered) upstairs and downstairs front and back. Hard to beat this location with Truman Waterfront down one end of the street and Duval St and all it offers just two blocks away. Call for your private showing and make this your own 'Piece of Paradise'!!
Located in a gated community within the highly sought-after Truman Annex in Old Town Key West, 202 Admirals Lane exudes coastal charm and luxury living at its finest. Boasting 5 bedrooms and 4 full bathrooms, this meticulously maintained residence showcases beautifully renovated bathrooms and a private pool oasis, offering an idyllic retreat for residents and vacationers alike. Situated nearby the iconic Duval Street and the tranquil expanse of Fort Zachary Taylor State Park, this home epitomizes the quintessential Key West lifestyle. Upon entering, you're greeted by an inviting main living area, adorned with French doors that effortlessly blur the lines between indoor and outdoor living. A sun-drenched sunroom, encased in glass doors, is the perfect setting for relaxation or entertainment year-round. Additional living spaces abound, including a bright and airy sitting room. The main floor is thoughtfully appointed with a convenient full bathroom, ensuring comfort and convenience for guests. The 2nd level offers 4 bedrooms and 3 full baths and the ensuite 3rd floor is great for guest. 202 Admirals Lane presents a lucrative investment opportunity as a successful vacation rental. Rare for Key West, this home features a coveted 2-car garage, providing secure parking and storage, a coveted amenity for sure. Offered turnkey, for a seamless transition for discerning buyers or investors seeking the ultimate Key West retreat.
Welcome to 60 Golf Club Drive, Key West, FL - A Fully Furnished Tropical Retreat with Private Pool and Turnkey Rental Opportunity SELLER CREDIT NOW OFFERED WITH QUALIFIED OFFER FOR NEW DOORS AND WINDOWS Step into island living at its finest in this beautifully appointed 3-bedroom, 2.5-bath home with well appointed den / office (could function as 4th bedroom) located in the sought-after Key West Golf Club community. This charming residence offers the perfect blend of comfort, style, and convenience, and is being sold fully furnished, including all furniture, décor, and household essentials--just bring your flip-flops. Enjoy your own private pool surrounded by lush tropical landscaping, creating a serene outdoor oasis perfect for lounging, entertaining, or a refreshing dip after a day in the sun. Whether you're seeking a vacation getaway or a lucrative investment, this home delivers. All future bookings (if any) will convey with the sale, offering immediate income potential and a seamless transition into ownership. Located in a gated community with 24-hour security, two resort-style pools, a fitness center, and close proximity to world-class dining, beaches, and downtown Key West, this property truly has it all. Don't miss your chance to own a turnkey slice of paradise in the Florida Keys.
This large home on an extra large 6300 sf corner lot is an excellent opportunity for a renovation project. The main home is just under 1600 sf and consists of 4 bedrooms and 2 bathrooms and there is also a good sized detached structure of almost 200 sf that could be turned in to, among other ideas, an extra bedroom, artist's studio or pool cabana. The home had the roof replaced in 2014 and has storm shutters. There are terrazzo floors. The extra large lot has sour orange, Spanish lime and banana trees, off street parking and plenty of room for a pool.
Fully renovated and redefined mid-century home, perfectly tailored for modern island living. Located on one of the most desirable streets in Key West, this turnkey property sits on an oversized 9,500 square foot lot in the heart of the island. Offering over 3,600 square feet of thoughtfully designed living space, the home features four bedrooms, four full bathrooms and a bonus room ideal for guests or a home office. The layout offers privacy and flexibility, with main-level guest rooms and an upstairs suite featuring cathedral ceilings, a spa-like bath and a spacious closet. The open-concept design is made for entertaining, with a sleek chef's kitchen featuring custom cabinetry, double ovens, an induction range and a walk-in pantry. Two laundry rooms and a second kitchen area upstairs add extra convenience and flexibility. Slide open the expansive glass doors and step into your own private resort. The living space transitions effortlessly to the outdoors, where you'll find tropical landscaping, multiple lounge areas, a covered porch for dining or relaxing and a heated lap pool with a stunning 28-foot custom waterfall. There's also an outdoor shower and a dedicated poolside half bath. Additional upgrades include new electrical and plumbing systems, three new central AC units, an irrigation system and a full furnishings package. The home also includes garage and driveway parking. Modern, stylish, and centrally located—this is Key West living at its finest.
This bright and well-maintained condo offers the perfect blend of comfort and convenience in one of Key West's most desirable neighborhoods. Just a straight shot down the road to White Street Pier, you're also minutes from both Higgs Beach and Smathers Beach for swimming, sunbathing, and seaside strolls. Head the other direction and you'll reach Bayview Park, with tennis courts, green space, and a community center. Inside, the condo features two comfortable bedrooms, a full bathroom, and the convenience of an in-unit washer and dryer. The living area is efficiently laid out, with natural light and a relaxed flow that makes the space feel open and inviting--ideal for year-round living or as a low-maintenance vacation home. The monthly condo fee for this unit is $355.60 and includes windstorm and liability insurance. *Seller is a licensed Florida realtor. Tenant in place until July 31, 2025.
Charming 1-bedroom, 1-bathroom condo offering 454 square feet of living space. The condo boasts an open floor plan with hurricanes rated windows, one assigned parking spot and also located in the X Flood Zone. The monthly condo fee for this unit is $238.96 and includes windstorm and liability insurance. The property is just few a few blocks from vibrant Duval Street, known for entertainment and dining options and additionally, it's within walking distance to the dog park, beaches, wildlife center, art galleries and much more! Tenant in place until July 31, 2026. *Seller is a Licensed Florida realtor.
Renovated and Elevated Key West Townhome - Move-in Ready at Exceptional Value. Discover this beautifully updated and elevated 2 bedroom, 2 bath townhome, conveniently located near schools, shopping, dining and all the attractions that make Key West such a vibrant place to live. With off-street parking for 2/3 vehicles and no detail overlooked, this home is offers a excellent combination of comfort, style and security. Enjoy hurricane-rated impact windows, new metal roof, marble powder finished walls & stunning Brazilian Cherrywood floors throughout. First Floor features Beautifully upgraded Kitchen, with granite countertops, tile backsplash, custom cabinets and a stainless steel appliance package, large spacious living room with built-in entertainment center and opens out to a covered porch where you can relax and unwind and enjoy the Florida Keys balmy breezes. Both Bedrooms located on the Second Floor with stunning renovated baths and a steam shower in Primary Suite. Spacious attic offers the potential to add a third bedroom, home office or playroom - great for growing families or your out of town guests. Low Annual HOA fee of $1500 and the elevated structure and impact windows will keep the insurance costs affordable. Property is a must-see and offers unbeatable value and an easy Island Lifestyle.
Welcome to this charming 1-bedroom, 1-bathroom apartment nestled in the heart of Key West. Located on desirable Seminary Street, this cozy yet functional home offers a perfect mix of comfort, character, and convenience. Step inside to find an open living space with hard flooring throughout the living room, office nook, and bedroom, complemented by easy-to-clean tile in the kitchen and bath. Natural light floods the interior through multiple windows and dual French doors that lead to a spacious private balcony — ideal for enjoying the tropical breeze. The thoughtfully designed layout includes a built-in desk and custom storage in the hallway, making great use of every inch of space. The bedroom features an airy open ceiling design that enhances the flow of light and air, creating a sense of openness rarely found in one-bedroom apartments. Additional highlights include in-unit washer and dryer, efficient window A/C units, and a location just minutes from the island's best dining, shopping, and beaches. Don't miss this unique opportunity to live in one of Key West's most charming neighborhoods. Schedule your private showing today!
Step outside to your own slice of paradise - a private oasis that beckons you to unwind and rejuvenate. The sparkling pool, adorned with stunning blue mosaic tiles, creates a mesmerizing focal point, while the soothing sound of its waterfall feature transports you to a world of tranquility. Surrounding the pool, a spacious deck provides the perfect setting for sunbathing, alfresco dining, or simply savoring the tropical ambiance. Lush, verdant landscaping envelops the property, creating a sense of privacy and serenity. Towering palms, vibrant foliage, and colorful flora paint a picture of tropical bliss, making every day feel like a vacation. The covered patio area, complete with comfortable seating, offers a shaded retreat for enjoying your morning coffee or evening cocktails. This property at 1118 Eaton Street isn't just a home; it's a lifestyle. Immerse yourself in the laid-back Key West atmosphere, where every day feels like an escape. Whether you're seeking a permanent residence or a dreamy vacation getaway, this charming oasis offers the perfect blend of comfort, style, and island living. Your Key West adventure starts here - seize this opportunity to make your tropical dreams a reality.
Welcome to 3300 Riviera Drive—an exceptional, turn-key, waterfront, residential estate featuring 4 bedrooms and 4.5 bathrooms. Nestled on three lots in a serene enclave just minutes from Old Town, this meticulously maintained property features 3,577 Sq. Ft. of living space and redefines Key West luxury, comfort and convenience. Step inside to discover an expansive open-concept living space bathed in natural light, with elegant finishes that include custom cabinetry, granite counters and hardwood floors. The gourmet remodeled kitchen, complete with high-end appliances including two dishwashers and a generous island, flows effortlessly into a spacious great room—ideal for entertaining. Wall to wall impact-rated sliders lend to an indoor/outdoor feel throughout the space, and lead to an expansive outdoor living area that overlooks the pristinely landscaped, resort-like grounds. Retreat to the primary suite, a private sanctuary featuring serene water views, wrap-around balcony, a spa-inspired bath with a steam shower and ample, two walk-in, closet space. Additional bedrooms, all with ensuite bathrooms, offer flexibility for guests, home office, or fitness needs. A gracious guest house, one bedroom and one bathroom, is located above the two car garage which gives your guests total privacy. Outdoors, lush tropical landscaping surrounds a stunning pool and patio, creating a peaceful ambiance with sunset views over the canal. A private sea-wall with boat lift offers direct access to open water — perfect for boating enthusiasts. Additionally, an electric gate leads to a climate-controlled two-car garage, ideal for storing vehicles. A two car carport is also located just out side of the garage, you can park four vehicles that will be covered from the elements, you just can't find this in Key West. Built with security and peace of mind in mind, the concrete property is elevated and includes impact-rated windows and doors throughout. Call today!
Courtesy: EXP Realty LLC
888-883-8509
Tropical elegance meets island living! Heart of Key West's New Town. Built 1953 but Effective year 2012 per tax assessor. Beautifully designed 3-bedroom, 2-bath Spanish Revival-style home offers 1,528 sq ft of interior space on an oversized 6,600 sq ft lot. Soaring cathedral ceilings, a split-bedroom layout, and a chef's kitchen with solid mahogany cabinetry, natural stone tile, and custom details. Step into your own private oasis with a large heated pool, raised spa, and lush landscaping. Renovated in 2019 with impact windows and doors, metal roof, and covered carport. Enjoy a peaceful residential setting minutes from beaches, shopping, and Old Town. Great full-time residence, a retirement retreat, or an income-producing vacation home, this Key West gem blends charm, comfort, and style
Fabulous Find on the Atlantic Side of Key West! Welcome to a truly unique opportunity in the heart of Key West. As the last and only remaining undeveloped property in the Historic Commercial Tourist District (HCT zone), this listing presents a rare and final chance to create something extraordinary. Imagine waking up to breathtaking, unobstructed ocean and beach views every day. Seabirds passing overhead, gentle breezes arriving at your lanai—it's an experience like nowhere else. This is island living at its finest! Permitted HCT uses include: Single-family and two-family residential dwellings, Multiple-family residential dwellings, Restaurant, Business and professional offices, Hotels, Motels, transient lodging, and more. This two-story home comes equipped with two separate electric meters. This exceptional property is truly one of a kind, with no identical or closely similar listings anywhere in Key West. The ideal circumstances are here and now— an unparalleled combination of an oversized ocean-view lot, located just three blocks from Duval Street, the gateway to downtown. Spanning 8,700 square feet, this property offers ample space for your creative vision, whether you dream of building a luxurious residence, alongside a commercial venture boutique hotel, or restaurant, — this and more are supported by HCT zoning. This property is all about the excitement of shaping a new vision for a future in paradise. Let your imagination run wild and transform this blank canvas into something extraordinary. Don't miss out on this once-in-lifetime opportunity—call today for your private tour and start envisioning your future in Key West!
Lovely 3 bedroom 2 bath home in the midst of Old Town just off Duval St. Central AC with nice room sizes and great lot size. Flood Zone Z500. Ready to sell As-Is. Seller motivated but firm on price.
Courtesy: Coldwell Banker Schmitt RE Co
305-743-5181
Seller is offering an assumable VA loan, buyer does not have to be a Veteran, please call for details. Updated 3-bedroom, 3-bath concrete block home with a spacious open floor plan, featuring a private marble pool area with a coral waterfall, mature trees, off-street parking, and more. Schedule your private tour today and discover your perfect, spacious, low-maintenance Key West home. Furnishings may be negotiable too.
Visualize yourself at this peaceful tropical residence, situated on a sprawling corner lot, enveloped by lush mature foliage. As you approach the front door, you'll be greeted with a variety of native and exotic plants including a glorious frangipani tree at your front door. Step through the doors of the single level home to discover three bedrooms and two bathrooms, a large kitchen, open-concept living spaces, and a large den that can easily be converted into a fourth bedroom, or home office. The home features a ceramic microbead roof overlay for energy efficiency, central air, and hurricane shutters. The expansive backyard contains an off-street parking space suitable for an RV, as well as ample space for a pool along with an abundance of mature landscaping. Ideally located just minutes from the beaches, vibrant entertainment district, and all the iconic attractions Key West has to offer, this corner-lot property combines convenience with potential. With generous parking and a prime location, it's perfect whether you're looking to elevate the existing home or reimagine the space entirely. Versatile, full of character, and brimming with opportunity—this is a rare find in the heart of Key West.
Experience the pinnacle of island sophistication with these beautifully appointed courtyard residences at the sought-after Beachside Condominiums in Key West. With two TRANSIENT RENTAL LICENSES, this turnkey property offers exceptional flexibility as a personal retreat, full-time residence, or lucrative vacation rental. WITH 50% SELLER FINANCING OFFERED = AN EXCEPTIONAL OPPORTUNITY! Thoughtfully designed as two separate, fully furnished units, this condo offers incredible versatility. Live in the spacious main condo (1074 sq.ft.) while renting out the second studio (282 sq.ft.) through the resort rental program—doing so could even offset your condo fees! Each unit has its private entrance, giving both owner and guest complete independence, privacy, and ease. Its premier lower-level location offers direct access to the pool and is in close proximity to parking, ensuring seamless convenience for both owners and guests. The interiors showcase refined finishes, designer furnishings, and a coastal aesthetic that perfectly captures the Key West lifestyle. Living here means enjoying a full suite of resort-style experiences right at your doorstep. Begin your day with a yoga class by the water or a workout in the fitness studio overlooking the Gulf. Lounge by the expansive waterfront pool or stroll to the private beach and marina, where you can relax in shaded loungers or embark on a sandbar or sunset cruise with on-site excursions. When it's time to dine, enjoy fresh island flavors and elevated cuisine at the resort's acclaimed restaurants. The complimentary downtown shuttle makes exploring Key West effortless, while covered parking, concierge services, and on-site rental management ease every stay or investment. Whether you're soaking in the sun on your private terrace, enjoying the vibrant resort atmosphere, or maximizing income potential through nightly rentals, this property offers a rare chance to own a piece of paradise with all the benefits of a world-class reso
Two Transient Homes Now Available For Sale. Just one block off world-famous Duval Street, this rare property offers two homes - each 3 bedrooms, 3.5 baths and private pools. These have strong rental histories. These well-appointed residences blend island charm with modern comfort, featuring open-concept living areas, updated kitchens and private ensuite bedrooms. Thoughtfully designed for guest privacy and relaxation, each home includes its own outdoor lounging space and pool—perfect for cooling off after a day in the sun or enjoying a quiet evening under the palms. Whether you're looking for a investment opportunity, a vacation retreat with rental flexibility, or a mix of both, this unique setup delivers unmatched versatility just steps from the vibrant restaurants, galleries, and nightlife of Duval Street.
The data relating to the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Florida Keys Board of Realtors® Florida Keys MLS, Inc. Real Estate listings held by brokerage firms other than the owner of this site are marked with the MLS logo and detailed information about them includes the name of the listing broker's office. Information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate.
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All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2026 BeachesMLS, Inc.
Key West is located in Florida. Key West, Florida has a population of 26,776. Key West is more family-centric than the surrounding county with 23.73% of the households containing married families with children. The county average for households married with children is 20.65%.
The median household income in Key West, Florida is $75,638. The median household income for the surrounding county is $73,153 compared to the national median of $69,021. The median age of people living in Key West is 44.2 years.
The average high temperature in July is 89.4 degrees, with an average low temperature in January of 63.6 degrees. The average rainfall is approximately 43.8 inches per year, with 0 inches of snow per year.
