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!
One of the largest LIVEABOARD slips in the Florida Keys.Perfect for large yachts and wide beam catamarans...Survey shows 100' long by 34' wide...but can accommodate up to 125' LOA boat.Safe Harbour Marina is a deep water (14' min.) protected port and recreational marina. Originally constructed in the late 1950's and located in the heart of the last vestiges of the commercial fishing and shrimping docks, it is a throwback to the old Key West, with a collection of locals, transplants, snowbirds, artists and craftsmen.One dockside assigned parking space, plus moped and bicycle parking.Private gated entrance, 3 phase electric, phone, cable and wireless internet. City water and pump-out. Unrestricted rental ability.Popular Restaurant / Bar on-site, secure bath, showers and laundry room. Small dip pool, dog park.Slip taxes included in the low quarterly $1,615.00 maintenance fee.3 miles to Key West Airport. 5 miles to downtown iconic Duval Street.Key West area the most convenient port in Florida to the Caribbean, Mexico, the Gulf States & South America.
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 !
LIVE IN PARADISE AFFORDABLE 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. City charges 4% or 5% transfer fee for the Lease transfer, plus 1st, last & Security. Closings are with Closing Agent Oropeza, Stones & Cardenas
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.
Investment opportunity! Weekly rentals are allowed! Nestled 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, the residence comes complete with all furnishings and future reservations, promising 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 OpportunityStep 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, decor, 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 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.
Spacious 4-Bedroom, 3-Bath Home on Expansive Lot with Fruit Trees!Welcome to this beautifully maintained 4-bedroom, 3-bathroom home nestled on a generous 9,375 sq ft fully fenced lot. Perfect for families and entertainers alike, this property offers the ideal blend of space, comfort, and outdoor living. Inside, you'll find a thoughtfully designed layout with ample natural light, spacious bedrooms. Step outside to your private oasis, complete with mature fruit trees and plenty of room for gardening, entertaining, or future additions. Whether you're dreaming of a backyard retreat, a play space for kids and pets, or simply enjoying your own slice of nature, this home has it all.
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. *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 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.
Charming Historic Gem in the Heart of Old Town Key West!Welcome to 729 Windsor Lane--a rare opportunity to own a piece of Key West history nestled in one of the island's most desirable residential neighborhoods. Set on an expansive nearly 3,000 sq.ft. lot, this classic home offers a generous footprint that's almost unheard of in Old Town, along with the luxury of coveted off-street parking.Step inside to discover a thoughtfully updated interior that blends historic charm with modern comfort. The remodeled bathroom features stylish tilework, updated fixtures, and a spa-like feel, while the upgraded kitchen boasts contemporary cabinetry, sleek countertops, and stainless steel appliances--perfect for preparing everything from a quiet Key West breakfast to tropical cocktails on the patio.Surrounded by lush native foliage, the property offers a serene, private setting just steps from Duval Street, world-class dining, art galleries, entertainment, and more--while maintaining the tranquility of a quiet residential neighborhood.For investors, the unbeatable location just a short stroll from Duval Street, renowned restaurants, nightlife, galleries, and cultural attractions makes this property ideal for monthly vacation rentals or long-term leasing to locals. For second-home buyers, it offers an effortless blend of privacy and proximity to the action, in a quiet residential neighborhood. Truly your home away from home. And for the historic home lover, this residence offers a chance to preserve and personalize a piece of Key West's architectural heritage with room to enhance over time and make it your own.With its historic architecture, upgraded amenities, and rare lot size, this home offers endless potential to create your tropical dream oasis. Whether you're looking for a charming island retreat, a vacation rental, or a full-time residence, 729 Windsor Lane delivers the perfect blend of location, lifestyle, and opportunity.
NEW AC ALL IN ONE HEATING AND AIR INSTALLED 12/25.Disscover your island oasis in this beautifully renovated 3-bedroom, 2-bath home. Situated on a larger lot, this property provides a serene escape just minutes from the heart of Key West (7 min drive) and the vibrant energy of Duval Street (17 min drive). Move right in and enjoy the ease of off-street parking, with plenty of space to create your dream backyard - picture a pool, jacuzzi, or lush landscaping! Located at the end of a quiet, dead-end street, you'll appreciate the peaceful setting and a lovely glimpse of water views. A truly prime location awaists!
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!
Location Location Location! Oceanview Condo Only 22 units nestled on an ocean front peninsula. Breathtaking views of flats, Mangrove estuary, and the Atlantic Ocean. Compare this property with the competition and you can for yourself. Unit 101 is an end unit with additional windows in the living area letting in natural light making this unit feel open and delightful. Unit faces East and enjoys afternoon shade and the fresh Easterly tradewinds making this balcony a breath of fresh air with spectacular views of the ocean and wildlife.
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!
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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 33040has a population of 26,776. Key West 33040 is more family-centric than the surrounding county with 24.54% 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 33040 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 33040 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.
