luxury real estate for sale Stock Island, United States

Welcome to 60 Golf Club Drive a fully furnished tropical retreat with private pool and turnkey rental opportunity. Step into island living at its finest in this beautifully appointed three bedroom, two and one half 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 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 is a unique opportunity to own 1200 sq feet of beautifully renovated condo space along with a 40nft deep water slip. The unit comes with one assigned off street parking space. Taxes, water, insurance, building and common area maintenance are covered under the dues.Weekly vacation rentals allowed for the condo.

Introducing Enchanted Island, an unparalleled private island located 1.5 miles from Key West accessible via its own private highway exit from US 1. This rare real estate jewel offers an exclusive escape like no other. Presently zoned for sub urban residential use, the island permits the construction of up to two homes. Elevated 15 feet to meet construction codes and with building permits already secured, Enchanted Island is posed for your development aspirations. Additionally, the seller has completed engineered architectural plans for a 7,437 SF home. For those with a vision grander in scale, the option of rezoning and securing permits for up to ten homes exists, providing endless possibilities for your imagination. Enchanted Island boasts all essential utilities, including a new 1000A 120/240V power service, underwater sewer and power lines, and AT&T fiber connectivity. With building permits in hand, your journey from blueprint to building can commence without delay. Spanning an impressive 4 acres, Enchanted Island offers both tranquility and unique features, such as a private ocean reef and partial dredging, ideal for potential boat dock installation. In addition to its private highway access, the island has a history with helicopter use, hinting at the potential for establishing a heliport to further enhance its exclusivity and convenience for the distinguished few who will call it home or their luxury getaway. Enchanted Island seamlessly combines isolation with connectivity, offering a lifestyle statement for the discerning few. This exotic haven envisioned for the elite seeking not just a residence but a statement of lifestyle, stands ready to fulfill visions of grandeur against the breathtaking backdrop of the Florida Keys. Seize the unparalleled opportunity to turn your dream of island living into your reality with Enchanted Island.

Welcome to 3841 North Roosevelt Blvd, Unit 121, the epitome of beachfront living at the Key West Beachside Resort and Residences. This stunning waterfront corner suite invites you to live like you are on vacation every day. This is a rare to come on the market opportunity, as there are only three one-bedroom units on the entire property, and this beachfront location remains the most desired. Inside, designer-grade finishes and furnishings create an atmosphere of refined elegance. Travertine flooring flows throughout the spacious living areas, complemented by an open gourmet kitchen featuring granite countertops, stainless steel appliances, and custom cabinetry. The well-appointed bedroom and two bathrooms provide ample space and privacy, while a sleeper sofa offers additional sleeping accommodations for guests. An oversized balcony provides a private retreat to enjoy the tropical breeze and breathtaking Gulf sunsets. Beyond your door, the resort's world-class amenities await, including a restaurant, bar, pool, spa, and fitness center. The on-site parking garage includes one deeded parking space, and there is a property shuttle for added convenience. This superb property offers incredible flexibility: use it as your private getaway, generate income through the onsite professionally managed rental program with no maximum stay restriction for owners, or both. The property boasts a proven track record of strong rental performance throughout 2025, demonstrating its appeal as a high-performing investment. Don't miss this prime opportunity to own a piece of paradise that is perfect for part-time residency and robust passive income. Reach out to learn more about how to make this your 2026 lifestyle.

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 residence offers 4 bedrooms + office, 4 bathrooms, and 2,458 Sq.Ft. of interior living space. Positioned on the coveted final canal in the exclusive Key Haven community, the home is designed for privacy, entertaining, and exceptional boating access. The layout offers rare flexibility. The entire top level functions as a private guest quarters, ideal as an elevated primary suite, luxury guest retreat, or in-law residence with some of the best water views in the home. This level also features a large covered porch spanning the entire floor, creating an additional private entertaining space. Inside, the architecture emphasizes volume, light, and clean modern lines. Tall ceilings, expansive glass, and large polished porcelain tile flooring create a refined coastal aesthetic. The open living area centers around a gourmet kitchen with Thermador appliances designed for entertaining. Stackable glass doors open the entire main living space onto a wide covered waterfront porch, for seamless indoor-outdoor living. A private elevator with access from ground level.Outdoor spaces include four decks, a rooftop deck with sweeping water views, a pool with swim-up bar, and a private putting green. The rooftop deck is ideal for spectacular sunsets and stargazing.For boating enthusiasts, the property features a 15,000 lb boat lift and davit with quick access to both the Gulf and Atlantic. Additional highlights include solid concrete construction, standing seam metal roof, elevator access, high-end finishes, and a large air-conditioned storage room. Photos include virtually staged furniture.

Set on the highly desirable upper end of Eagle Avenue, this four bedroom, three bath home blends timeless charm with a breezy indoor outdoor lifestyle. Arched doorways, plantation shutters, and warm wood floors set the tone, while natural light fills the expansive living spaces. The main living area is centered around a working gas fireplace, creating a welcoming focal point for both everyday living and entertaining. On the main level, you will find three bedrooms, two bathrooms, a formal dining room, and a separate cooks kitchen featuring custom cabinetry, quartz countertops, premium appliances, and a center island. Glass fold back doors open to a covered outdoor living area, pool, and spa, extending the living space outdoors and creating a relaxed courtyard style setting ideal for entertaining or unwinding. Upstairs, the fourth bedroom with ensuite bath offers a private retreat, along with an additional living space and a large finished attic providing exceptional storage. This home provides the perfect opportunity to personalize every space and make it your own. Additional highlights include gated, covered off street parking, tiled walkways, and a fully fenced property for added privacy. Some photos have been virtually enhanced to illustrate potential.

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 moments from the vibrancy of Key West, this residence offers a lifestyle defined by serenity, sophistication, and seamless access to world-class culture, 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.

Situated on one of Key West's most desirable streets, this private compound on Eagle Avenue offers a rare combination of space, privacy, and refined island living. Set on a double corner lot totaling 12,000 sq ft, the property is fully enclosed, offering enhanced privacy and a tranquil, resort-like setting. The main residence features 3 bedrooms, 2.5 baths, and approximately 1,765 sq ft of thoughtfully designed living space with a comfortable open floor plan ideal for entertaining. The spacious primary suite serves as a private retreat, complete with a large en suite bath featuring a walk-in shower and oversized Jacuzzi tub. A separate guest cottage offers 1 bedroom, 1 bath, and approximately 625 sq ft, providing excellent flexibility for guests, extended family, or additional living space. The professionally landscaped grounds are a standout feature, enhanced by landscape lighting and irrigation, and centered around a large pool set within an exceptionally private backyard. Outdoor amenities include a hammock and swing area, outdoor shower, and multiple areas for entertaining or quiet relaxation beneath the palms. Additional highlights include a whole-house generator, as security system, one-car garage, and generous off-street parking. Surrounded by notable luxury homes, Eagle Avenue is known for its quiet atmosphere, large lots, and enduring desirability. A rare opportunity to own a private Key West compound offering privacy, flexibility, and presence on one of the island's most sought-after streets. Seller is a licensed real estate agent.

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!

Welcome to 1510 18th Street in the highly desirable Sunrise Shores neighborhood of Key West! This 3-bedroom, 2-bathroom home offers the perfect combination of island living, convenience, and outdoor lifestyle, just minutes from shopping, dining, beaches, the boat ramp, and all that Key West has to offer. Set on an oversized lot, this property provides ample off-street parking with plenty of space for boat storage, RV parking, or additional vehicles—a rare find in Key West. The private backyard oasis features lush tropical landscaping, a beautiful swimming pool, and a large outdoor entertaining deck, ideal for relaxing, hosting guests, or enjoying the Florida sunshine. Inside, the home offers a spacious primary suite with an en-suite bathroom, two additional generously sized bedrooms, and a large open kitchen that flows seamlessly into the dining area and den. The layout is perfect for full-time living, a vacation home, or an investment property. Located in a quiet, established neighborhood, this Key West home delivers outdoor living, parking flexibility, and prime location—don't miss this opportunity to own a piece of paradise.

Welcome to your dream home in the heart of Key West's MidTown! This beautifully updated 3-bedroom, 2-bathroom residence blends modern comfort with island charm. Step inside to a spacious, open-concept living area designed for both relaxing and entertaining. The true highlight is the private backyard oasis — featuring a sparkling pool surrounded by fresh tropical landscaping, an expansive deck, and plenty of room for outdoor dining and lounging. Whether hosting guests or enjoying a quiet evening under the palms, this outdoor retreat feels like your own private paradise. Recent renovations provide peace of mind, including new impact windows and doors, Hardie board siding, and other thoughtful upgrades. Off-street parking adds everyday convenience. Perfectly located in the desirable MidTown neighborhood, this home keeps you close to shopping, dining, and all the best of Key West living.

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.

Rare Opportunity: Three Charming Homes on Adjacent Lots - Unlimited Potential! Discover the perfect investment opportunity with these three vintage 2-bedroom, 1-bathroom homes, nestled on separate adjoining lots and being sold together as a single package. Situated in a desirable location, this unique offering provides incredible flexibility for visionary buyers. Each home offers cozy layouts that are ripe for restoration or redevelopment. The true value lies in the combined potential of these properties-create a sprawling family estate, build a modern multi-home compound, or explore other construction options to maximize value. With their combined potential and prime location, these homes are a once-in-a-lifetime opportunity for developers, investors, or those looking to build their dream family retreat. Don't miss out, bring your imagination and start planning the possibilities today! Contact me to schedule a showing and envision the future of this incredible property package!

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.

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!

***BRAND NEW ROOF JUST INSTALLED *** 1614 Dennis St is a rare income-producing triplex offering strong cash flow and flexible use in the heart of Key West. Generating over $125,000 annually in rental income, this well-configured property features three separate units, each with its own washer and dryer, making it highly desirable for long-term tenants and employee housing. The layout includes two spacious 2-bedroom / 1-bath units and an upstairs 3-bedroom / 2-bath residence, providing multiple rental strategies and value-add potential. A standout feature is parking for up to 7 vehicles--a true luxury in Key West and a major draw for tenants. Large Shed on property with two dedicated spaces that could be converted into a workspace. Ideal for investors seeking steady returns or employers looking for quality workforce housing, this triplex combines strong income, practical design, and exceptional parking in one compelling opportunity. Please note some photos were digitally staged and or altered to protect tenant privacy.

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.

Located in the heart of Key West, 1712 Laird Street offers a rare blend of central convenience and residential tranquility. Positioned within a short stroll of Smathers Beach, Higgs Beach Park, the Key West Nature Preserve, White Street Pier, and the island's beloved Garden Club and dog park, this home places the best of the island lifestyle quite literally at your doorstep. Duval Street and the Old Town Historic District lie just 1.5 miles away, while Mallory Square and the waterfront—famed for their sunsets, dining, and culture—are approximately 2 miles from the property, allowing effortless access without sacrificing peace and privacy . Designed by an architect with a discerning eye for light and space, the residence showcases a modern open-concept floor plan enhanced by expansive glass elements that invite the outdoors in. Cathedral ceilings soaring from 12 to 15 feet throughout every room create a sense of volume and airiness seldom found in Key West homes, delivering a bright, refined interior that feels both contemporary and timeless . Set on a 5,000-square-foot parcel, the grounds are thoughtfully landscaped with low-maintenance native flora, including seven mature palm trees, a striking gumbo limbo, and established orchids. The result is a private tropical sanctuary—lush, authentic, and effortlessly elegant—perfectly suited for island living without pretense . Large back yard offers plenty of space to add a pool!

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.

Architect-designed and purpose-built for modern island living, 1614 Washington Street delivers a rare combination of durability, intelligence, and refined restraint. This is a luxury home defined not by excess, but by performance, longevity, and thoughtful design. Constructed with solid masonry, impact-rated windows and doors, and positioned above flood elevation, the home offers a level of resilience and peace of mind increasingly sought in today's coastal market. Materials and systems were selected for low maintenance and long-term reliability, creating a residence that is as practical as it is elegant. The home reflects the work of award-winning local architect Matthew Stratton, whose projects have been featured in Architectural Digest and Coastal Living. It is designed with a philosophy centered on efficiency, foresight, and long-term coastal performance. Energy independence is integral to the design. A solar infrastructure paired with Tesla battery storage supports uninterrupted power, and a quieter, more secure lifestyle-an elevated approach to sustainability that enhances daily living rather than complicating it. The interior floor plan is owner-forward and highly livable. The primary suite is located on the main level, offering privacy and ease. At the same time, three additional en-suite guest bedrooms are intentionally arranged around a den/lounge space on the second level, ideal for extended stays or visiting guests. Finishes include porcelain tile flooring, quartz surfaces, custom cabinetry, and high ceilings that bring light and volume throughout. Outdoor living is private and well-defined. A two-tiered pool with a splash deck and water features anchors the backyard, surrounded by mature tropical landscaping that creates a true island retreat. At its core, 1614 Washington is not about excess; it's about intelligence. A fortress when needed, a retreat when desired, and a design-forward home whose value is revealed in daily living, not just on paper.