luxury real estate for sale Stock Island, United States

This is a unique opportunity to own a 25 X 80 deep water slip in paradise. The slip comes with parking and all the amenities of Safe Harbor Marina.

Where the essence of the Florida Keys meets refined coastal luxury, 94 Driftwood Drive stands as a rare bayfront sanctuary in coveted Key Haven. Just minutes from the energy and culture of Key West, this residence offers a lifestyle defined by serenity, sophistication, and seamless access to world-class cuisine and adventure. Framed by spectacular water views from every room, the home's architecture embraces its setting with an effortless elegance. A mesmerizing infinity-edge pool and spa appear to merge with the open sea, creating a private resort experience at the water's edge. Inside, the striking chef's kitchen commands attention with state-of-the-art appliances and a dramatic solid-walnut entertainment island--an exquisite centerpiece for gatherings both intimate and grand. Offering 5 bedrooms and 5.5 baths, including primary suites on both levels, the residence is designed for comfort, privacy, and elevated living. Hardwood floors, impact-glass windows, and an oversized 2-car garage with direct dock access and room for a boat trailer reflect thoughtful craftsmanship throughout. Flexible spaces accommodate a gym, studio, or entertainment room, while a meticulously organized storage area supports both home and pool systems with precision. For the boating and water-sport enthusiast, a dedicated equipment room provides direct access to the oceanfront dock and boat lift, placing the Keys' endless waterways at your doorstep. A custom iron staircase rising from the first to the third floor serves as a sculptural showpiece, its ocean-inspired artistry echoing the home's coastal surroundings. 94 Driftwood Drive is more than a residence--it is a statement of lifestyle, where tranquility and sophistication meet the unmistakable allure of the Florida Keys.

Step inside your perfect Key West condo! This 2 bedroom and 2 full bathroom condo offers the best of Key West living! A split bedroom floor plan makes this ideal for guests or multi family living. The balcony offers peaceful views of the Salt Ponds and a great space to relax. The wonderfully maintained grounds offer a newly renovated swimming pool, a tennis court and BBQ area. Smathers Beach is just a short bike ride / walk away and the path offers a great spot for morning walks by the ocean. Your own private covered parking bay affords quick access to the elevator. Call for your private showing and make this your Key West home today!

3200 Harriet Avenue , Key West, FL Tucked away on a desirable corner lot, this spacious 2-bedroom, 1.5-bath townhouse offers 1,332 square feet of comfortable living and one of the largest floor plans in the community. Combining privacy, generous living space, and exceptional outdoor amenities, this home is a rare find in Key West. One of the property's most appealing features is the absence of HOA fees, allowing you to enjoy all the benefits of homeownership without monthly association dues or restrictive community fees. It's a rare opportunity to own a spacious townhouse with the freedom and flexibility typically associated with a single-family home. Step outside to your own private pool, creating the perfect setting for entertaining, relaxing, or enjoying the tropical island lifestyle year-round. The corner-lot location provides added privacy and outdoor space, making this home feel even more secluded. Inside, the well-designed floor plan offers bright, inviting living spaces with plenty of room to gather, work from home, or simply unwind after a day on the water. Conveniently located in New Town, 3200 Harriet Avenue is just minutes from shopping, dining, schools, beaches, and all that Old Town Key West has to offer. Whether you're looking for a primary residence, vacation home, or investment property, this home delivers an outstanding combination of space, privacy, and the quintessential Key West lifestyle.

This absolutely stunning 5-bedroom, 5-bathroom home, re-imagined and built brand new in 2023, offers 3,062 sq. ft. of luxurious living space on a 5,040 sq. ft. lot. Featuring 9' ceilings, custom wood cabinetry, porcelain wood-style and LVT flooring, a 17-foot island seating 8, the head chef's kitchen is equipped with professional-grade appliances, including a 36'' gas stove & vented hood, and wine fridge. The master suite boasts a walk-in closet and spa-like wet-room bathroom with dual shower-heads, claw-foot tub, and dual vanities. Additionally there are laundry spaces on each floor, ample storage, attic space and underneath the home. impact-resistant windows, spray foam insulation, aluminum standing seam double strapped roof, and a future-proof design that exceeds building codes, this home is built to last. The backyard includes a heated pool, thatched chickee hut, and privacy landscaping. Upon entry you will be in awe throughout of the linear symmetry, meticulous craftsmanship and no detail overlooked which makes this a true gem.

Opportunity in the desirable Lime Grove neighborhood of New Town Key West! Situated on an oversized corner lot, this CBS home offers 1,242 sq. ft. of living area, an expansive yard and plenty of possibilities for its next owner. Owned by the same family for decades, the property has been lovingly maintained and is ready for its next chapter. Originally designed as a three-bedroom home, two of the bedrooms were opened into one another by removing the dividing wall, creating one oversized bedroom. The third bedroom remains separate, and the original three-bedroom configuration could potentially be restored by a new owner by adding the dividing wall. The generous corner lot provides abundant outdoor space with plenty of room to create a tropical outdoor living area and potential for a pool. The property also includes a detached 483 sq. ft. CBS garage/workshop in need of significant repair and rehabilitation, offering the potential to restore and repurpose the structure. Attached to the rear of the garage is a 228 sq. ft. utility/laundry/storage space. Inside, the home retains much of its original character with ample potential for updating and personalization. Whether envisioned as a primary residence, long-term rental investment or renovation project, the spacious lot, CBS construction, flexible layout and New Town location provide a great foundation for its next chapter. Just steps from Lake McKillip, take an evening stroll along the public wooden walkway over the water and enjoy beautiful Key West sunsets. Conveniently located in New Town near shopping centers, schools, the senior center, beaches and everything the island has to offer. Bring your vision and discover the possibilities at 2804 Harris Avenue.

Experience the quintessential island lifestyle in this stunning waterfront townhome at Flagler's Landing, where Gulf views meet the convenience of a central Key West location. This elevated residence offers approximately 1,387 sq ft of living space with open Gulf views from the main living areas, private balcony, and both upstairs bedrooms. The main level is designed for effortless entertaining, featuring an open-concept design with spacious living and dining areas. The gourmet kitchen is anchored by a custom coral stone island with seating for six, equipped with custom cabinetry, under-cabinet lighting, premium GE appliances, a six-burner range, and a brand-new refrigerator. Warm bamboo flooring, recessed lighting, and a wide waterfront balcony accessed through sliding glass doors create an inviting atmosphere for indoor-outdoor living, perfect for enjoying sunsets and ocean breezes. A powder bath completes this level. A spiral staircase leads to the second level, where the hallway features built-in bookshelves and access to an additional front-facing balcony. Both serene bedrooms enjoy expansive waterfront views and walk-in closets. The primary suite and guest bedroom provide a relaxing coastal setting for family or visitors, complemented by a full bath featuring a glass walk-in shower, a large vanity, and a jacuzzi-style tub. Additional features include central A/C, ground-level covered private parking, dedicated storage, a laundry area, and a charming ground-floor brick patio. For boating enthusiasts, the property includes a private shallow-draft boat slip suitable for an approximately 24 ft boat, enjoyable any season all year. Residents also enjoy community access to a heated concrete pool. Perfectly situated near beaches, restaurants, shopping, and marinas, this home provides a unique opportunity to own a premier piece of paradise in an exclusive enclave where properties rarely become available.

Embrace the laid-back lifestyle of the Florida Keys in this waterfront two-bedroom, two-bathroom condominium with beautiful water views. Soaring vaulted wood-beamed ceilings, a skylight, and expansive sliding glass doors fill the home with natural light while showcasing the sparkling water beyond. The open-concept living and dining areas flow seamlessly to a spacious wraparound balcony, creating the perfect setting to enjoy your morning coffee, entertain guests, or unwind with the island breeze. The functional kitchen opens to the main living area, making entertaining effortless. Located in Bay Villas, a boutique waterfront community of just nine residences, residents enjoy beautifully maintained grounds, a community pool, boat docks, and inviting waterfront gathering spaces. Whether you're looking for a full-time residence, a seasonal getaway, or an investment opportunity, this waterfront retreat offers the relaxed charm that makes the Florida Keys so special.

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 !

Discover the rare opportunity to own a premier developer's unit in one of Key West's most desirable waterfront communities. Perfectly positioned just across the street from world-famous Smathers Beach, this spacious 3-bedroom, 2-bath condo blends coastal luxury with unbeatable island convenience. Inside, expansive living spaces open to large windows and glass doors showcasing ocean views and endless natural light. The open-concept kitchen flows seamlessly into the dining and living areas—ideal for entertaining or relaxing after a day on the sand. Retreat to the ocean-view primary suite, complete with generous closet space and private bath. Two additional bedrooms offer the flexibility for guests, family, a home office, or rental income. Step outside and enjoy resort-style amenities—lush tropical grounds, shoreline paths, sparkling pool, and easy access to water sports, biking, and Key West's sunset scene. Whether you're seeking a primary residence, island getaway, or investment opportunity, this condo delivers everything that makes Key West living unforgettable. Highlights: *Rare developer's unit with expanded layout/premium features *Just steps to Smathers Beach, bike paths & sunrise walks *3 Bedrooms / 2 Bathrooms *Assigned covered parking bay and storage unit *Resort amenities & gated community *Minutes to Old Town, dining, airport & nightlife Your Key West waterfront life starts here—schedule your private showing today!

Investment Opportunity - Income-Producing Triplex! Don't miss this excellent income-producing triplex located in a convenient, high-demand area close to schools, shopping, dining, parks, and just minutes from downtown Key West. Whether you're looking to expand your investment portfolio or occupy one unit while generating rental income from the others, this property offers outstanding potential. A rare feature of this property is the ample off-street parking, with room for up to 7 vehicles--a highly desirable amenity for both tenants and owners. The flexible layout provides multiple rental opportunities and consistent income potential in a strong rental market. Unit A = 2/1 Unit B = 2/1 Unit C (upstairs) = 3/2 With its desirable location, generous parking, and proven income-producing capabilities, 1614 Dennis Street is an exceptional opportunity for investors or owner-occupants alike. Schedule your private showing today!

Multi-unit legal duplex! With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting one unit while living in the other. Set on a 5,000 sq ft lot, the property is surrounded by lush, mature tropical landscaping with a wide variety of plants and palms, creating a private, shaded, treehouse-like setting filled with natural light. Two large screened porches and additional open-air spaces provide ideal indoor-outdoor living, while an outdoor shower enhances the island lifestyle. The home has been thoughtfully updated and well cared for, featuring Mitsubishi mini-split A/C systems in both units, a new hot water heater, new ceiling fans, impact windows upstairs, new gutters, updated appliances, and soft-close cabinetry. Interior finishes include a mix of pine, vinyl, and concrete flooring, along with stainless, Formica, and butcher block countertops. Both units offer full bathrooms with tubs. Additional highlights include two off-street parking spaces, low-maintenance grounds, and multiple windows throughout for abundant natural light and airflow. Located in desirable Midtown East, just minutes from everything Key West has to offer, this is a versatile, income-producing property with strong upside potential.

Welcome to 1724 Rose Street, a spacious single-family home on a generous corner lot in a quiet Midtown neighborhood, close to Key West's beautiful beaches. The main level features an inviting open-concept kitchen, dining, and living area, along with three bedrooms and two baths. Freshly painted inside and out, the home is move-in ready while offering an opportunity to add your own personal touches and updates. The upstairs addition was done in 2016 offering two additional studio spaces. Both studios provide exceptional flexibility and could potentially be configured with a separate entrance, making them ideal for guests, extended family, a home office, or additional living accommodations. The large corner lot offers off-street parking for 2-3 vehicles, plus abundant on street parking. Out back, the spacious yard has plenty of room to create your own private oasis, with space for a large pool, outdoor lounging and entertaining areas, plus ample storage. With its flexible layout, generous lot, parking, and desirable Midtown location, this property offers numerous possibilities--from a comfortable home for a large family to monthly vacation rental use or employee housing. A rare opportunity to create a spacious Key West retreat with room to grow, customize, and enjoy the island lifestyle.

Welcome to Casa Lanka in Key West! This unique property consists of a 4 bedroom 3.5 bath CBS home on a double lot with an abundance of mature tropical plants creating a private oasis. Tucked away from the main home, a separate cottage makes an ideal space for guests, extended family, or a private office. A sparkling pool anchors the outdoor living space, surrounded by mature tropical landscaping and a peaceful walking path that winds through the property. Additional features include a spacious carport accommodating up to four vehicles, a large airconditioned utility room and a large shed. This unique offering blends indoor and outdoor living, creating a peaceful island hideaway close to everything Key West has to offer. Seller is open to reviewing all offers!

Designed for relaxed island living, this modern home blends privacy, comfort, and convenience in Midtown, just minutes from dining, beaches, and nightlife. Clean lines, tall ceilings, and an abundance of natural light define the open-concept living spaces, while retractable impact glass doors invite seamless indoor-outdoor living. The updated kitchen pairs style with function, featuring quartz countertops, a tile backsplash, premium stainless-steel appliances, and open sightlines to the dining and living areasperfect for entertaining. The living space extends outdoors to a backyard retreat with a pool, generous lounge areas, and room for both sun-soaked afternoons and relaxed evening gatherings. The covered pool bar and adjacent half bath add thoughtful convenience for hosting. The primary suite is elevated and positioned in its own wing, offering a calm retreat with en suite bath, walk-in closet, and access to a private deck overlooking the pool. Two additional bedrooms are equally well-appointed, providing comfortable accommodations for family or guests. Built with durability and ease of maintenance in mind, the concrete construction includes a metal roof, impact doors and windows, security system, and a private gated driveway with two keypad entry gatesideal for full-time residents or seasonal use. For buyers seeking investment potential, the property already offers a strong rental history, with January through March secured at $41,500 and returning tenants eager to continue year after year. Bright, airy, and thoughtfully designed, this home captures the essence of relaxed modern living in one of Key West's premier neighborhoods.

Excellent investment opportunity. This condo unit comes with a 25 X 60 deep water slip. The unit has been divide into three separate rental spaces. one bedroom, full bathroom with a kitchenette and two separate sleeping rooms with full bathrooms. Minutes from Key West.

Welcome to an extraordinary oceanfront residence in the exclusive Casa Caselles community, where two townhomes have been masterfully combined into one spectacular 4,224 sq. ft. luxury retreat. Completely reimagined, this one-of-a-kind home features a private interior elevator with automatic doors accessing all floors, exceptional craftsmanship, and effortless oceanfront and poolside living. Offering 4 en-suite bedrooms, 4.5 baths, 2 expansive living rooms divided by a wall insulated with commercial soundproofing, an exercise room, and a hidden office seamlessly integrated into the custom kitchen, the residence is designed for everyday comfort and grand-scale entertaining. The chef's kitchen centers around an oversized island with custom European-style cabinetry, premium quartz countertops, a BlueStar gas range, paneled Sub-Zero refrigerator, Cove dishwasher, U-Line ice maker, wine refrigerator, and Perlick refrigerator/freezer drawers. The family room includes an electric fireplace and custom wet bar with refrigerator drawers, dishwasher, and built-in cabinetry. Travertine flooring, custom built-ins, hidden storage, recessed lighting, remote-controlled window coverings, and in-wall TV wiring reflect meticulous attention to detail. Every major system has been replaced, including electrical, plumbing, insulation, and HVAC. Twelve balconies and hurricane-rated sliding glass doors provide beautiful light in every room, while a whole-house generator provides peace of mind. The luxurious primary suite offers a custom walk-in closet, and every bedroom has private balcony access. A guest suite includes a zero-entry shower for added comfort and accessibility. Tiled courtyards, expanded entertaining terraces, covered parking for four vehicles, an outdoor shower, and multiple laundry areas enhance daily living. Residents also enjoy an oceanfront pool overlooking the Atlantic, completing one of Key West's most distinctive waterfront residences.

Charming Key West living in a fantastic central location! This inviting end-unit condo offers an easy, low-maintenance opportunity to own a piece of the island, whether you're looking for a full-time residence, Key West getaway, or investment property. The bright interior features tile floors, granite countertops, central A/C and a functional kitchen, while the fenced outdoor space adds a rare touch of private outdoor living. Surrounded by tropical landscaping and just a short bike ride from Old Town, beaches, restaurants, shopping and everything Key West has to offer. A great opportunity to enjoy the Key West lifestyle or add an island property to your investment portfolio.

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 space and situated on a 5,896 S. F. corner lot. This CBS home has all hurricane impact rated windows & doors, flood panels for all doors, and 25 KW Generac stand by whole house generator. There is an abundance of windows & doors allowing for plenty of natural light throughout the home. True chefs kitchen features gorgeous cabinets & counter tops with all stainless steel appliances. Dual ovens, gas stove top range, and wine cooler make your kitchen complete. The kitchen opens up to your amazing living & dining room areas. From there you will find this opens up to a super nice covered outdoor patio area, in ground, salt water, and heated 27L X 9W Jacuzzi & pool with water fall. Ready to kick back and relax. Outdoor areas have travertine tiles throughout and have lush native tropical landscaping with lighting & irrigation systems. Property has a 1 car covered carport and CBS privacy fencing around entire property. This home is located within walking distance to Higgs Beach, White St. Pier, and a short distance to Key West Best restaurants, beaches, museums, and art galleries. This is truly a home where modern luxury meets Key West paradise. Listing agents are related to the sellers.

Timeless Old Town Charm! Discover the timeless appeal of this beautifully remodeled historic home located in the heart of Old Town, Key West. Offered fully furnished, this stunning 3-bedroom, 2.5-bath residence showcases lovingly restored Dade County Pine and blends classic craftsmanship with today's most desirable upgrades. 1211 Knowles Lane features a versatile 300 sq. ft. loft currently utilized as a third bedroom, office, and additional storage, perfect for flexible island living. Inviting front and side porches set the tone for relaxed Key West living, offering peaceful spaces to unwind and enjoy the tranquil neighborhood. Inside, you're welcomed by bright, spacious living areas highlighted by soaring ceilings and gorgeous flooring throughout the living and dining rooms. The thoughtfully updated kitchen boasts stainless steel appliances, custom cabinetry, and a generous pantry designed for both everyday living and entertaining.The bedrooms are comfortably sized, offering charm and privacy. Bathrooms have been tastefully renovated with contemporary fixtures while preserving the home's historic character. Step outside onto beautiful teak decking into your own private tropical oasis. The backyard retreat features an outdoor shower, hot tub, rooftop deck, and brick-paved driveways creating the ultimate indoor-outdoor island lifestyle. Located in a prime Old Town setting, you're just a leisurely walk or bike ride to Key West's beautiful beaches, renowned restaurants, and vibrant nightlife. *Bonus features: off street parking and located in the x-flood zone.

Stunning possibilities abound for this home on a double lot on the best street in the much sought after Casa Marina neighborhood in Key West. 1017 Washington Street is a renovation away from being your trophy property. The existing house has lots of room with 2,604 square feet of finished space with 4 bedrooms and 2.5 bathrooms. The oversized lot has even more room with 10, 724 square feet, a large swimming pool and an outdoor shed perfect for outdoor kitchen and living space. The property has never flooded and sits above flood. The possibilities are endless. Come see it today.