Key West Homes with Bay View

Welcome to your waterfront escape in Key West. Located within a gated community, Gulfview Pointe offers the perfect blend of island charm, comfort, and an exceptional waterfront lifestyle and just minutes from world-famous Duval Street and all that Key West has to offer. This move-in-ready 3-bedroom, 2.5-bath home welcomes you with classic Key West architecture, lush tropical surroundings, and inviting indoor and outdoor living spaces. The kitchen features granite countertops, stainless steel appliances, and ample cabinetry. Step outside to your own private tropical retreat, where a sparkling pool surrounded by composite decking creates the perfect setting for relaxing, entertaining, and enjoying the year-round Florida Keys sunshine. Beyond the pool, your private dock opens the door to endless adventures. Spend the afternoon fishing, set out on your personal watercraft, paddleboard or kayak, or simply unwind and watch another spectacular Key West sunset from your own backyard. A covered carport and the privacy of a gated community complete this island home. Whether you're searching for a full-time residence, your own Key West getaway, or investment opportunity with luxury vacation rental potential in this highly sought-after community, Gulfview Pointe offers an exceptional opportunity. Opportunities like this don't come around often--invest in your dream home and start living the Key West waterfront lifestyle you've been dreaming of. Call today to schedule your private showing!

2623 Gulfview Dr, Key West

$995,000

2 Beds ⋅ 2 Baths ⋅ 620697 MLS

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, 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.

32 Hilton Haven Rd Unit APT 5, Key West

$4,750,000

6 Beds ⋅ 5 Baths ⋅ 620662 MLS

TRANSIENT LICENSE TRANSFER RECEIVER ZONE!!!! A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the historic Trumbo Point waterfront, this remarkable estate has remained in the same family for generations and reflects a rich connection to one of the island's most significant maritime neighborhoods. Thought to have origins dating back to the early 20th century, the property showcases timeless Old Key West charm while offering the space and flexibility rarely found today. The main residence is complemented by a separate guest cottage on an oversized waterfront parcel, creating endless possibilities for multigenerational living, a private family compound, or an exceptional investment opportunity. Located in an area once shaped by the island's cigar industry, railroad expansion, and later the development of the Naval Air Station and Coast Guard facilities, this home sits within a neighborhood that tells the story of Key West's evolution through more than a century of history. From the moment you arrive, you'll appreciate the mature tropical landscape, water access, and the feeling of stepping into a piece of Old Key West. Whether you choose to preserve its historic character, thoughtfully enhance the existing structures, or create your own legacy estate, opportunities like this are exceptionally rare. Waterfront properties with this combination of history, location, size, and family ownership seldom become available. 901 Eisenhower Drive is more than a home--it's an opportunity to own a meaningful piece of Key West's past while creating its next chapter.

901 Eisenhower Dr, Key West

$4,750,000

7 Beds ⋅ 5 Baths ⋅ 620661 MLS

TRANSIENT LICENSE TRANSFER RECEIVER ZONE!!!! A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the historic Trumbo Point waterfront, this remarkable estate has remained in the same family for generations and reflects a rich connection to one of the island's most significant maritime neighborhoods. Thought to have origins dating back to the early 20th century, the property showcases timeless Old Key West charm while offering the space and flexibility rarely found today. The main residence is complemented by a separate guest cottage on an oversized waterfront parcel, creating endless possibilities for multigenerational living, a private family compound, or an exceptional investment opportunity. Located in an area once shaped by the island's cigar industry, railroad expansion, and later the development of the Naval Air Station and Coast Guard facilities, this home sits within a neighborhood that tells the story of Key West's evolution through more than a century of history. From the moment you arrive, you'll appreciate the mature tropical landscape, water access, and the feeling of stepping into a piece of Old Key West. Whether you choose to preserve its historic character, thoughtfully enhance the existing structures, or create your own legacy estate, opportunities like this are exceptionally rare. Waterfront properties with this combination of history, location, size, and family ownership seldom become available. 901 Eisenhower Drive is more than a home--it's an opportunity to own a meaningful piece of Key West's past while creating its next chapter.

901 Eisenhower Dr, Key West

$450,000

2 Beds ⋅ 2 Baths ⋅ 620647 MLS

2 BEDROOMS 2 BATHROOMS WITH BALCONY, GATED COMMUNITY, HUGE POOL, TENNIS COURT ,PLENTY OF PARKING AND WALKING DISTANCE OF SHOPPING, GROCERIES, RESTAURANTS AND MOVIE THEATRE.

3312 N Northside Dr Unit 607, Key West

$1,375,000

2 Beds ⋅ 2 Baths ⋅ 620045 MLS

Experience quintessential island living in this stunning waterfront townhome at Flagler's Landing, where sweeping Gulf views meet a central Key West location with private boat dockage. This elevated residence offers ~1,387 sq ft of living space with open water views from the main living areas, private balcony, and both upstairs bedrooms. Designed for effortless entertaining, the main level features an open-concept layout with spacious living and dining areas. The gourmet kitchen anchors the space with a custom coral stone island (seating for six), custom cabinetry, under-cabinet lighting, premium GE appliances, a six-burner range, and a new refrigerator. Warm bamboo flooring, recessed lighting, and a wide waterfront balcony create an ideal indoor-outdoor flow for sunsets and ocean breezes. A powder bath completes this level. A spiral staircase leads to the second level, where the hallway offers built-in bookshelves and a front-facing balcony. Both serene bedrooms feature walk-in closets and expansive water views. The primary and guest suites share a full bath with a glass walk-in shower, large vanity, and jacuzzi-style tub. Additional features include central A/C, ground-level covered parking, dedicated storage, a laundry area, and a ground-floor brick patio. For boating enthusiasts, the property includes a private shallow-draft slip suitable for a ~24 ft boat. Residents also enjoy community access to a heated concrete pool. Situated near beaches, dining, shopping, and marinas, this home is a rare opportunity to own a piece of paradise in an exclusive Key West enclave.

9 Mccoy Cir Unit 9, Key West

$850,000

2 Baths ⋅ 619620 MLS

FOR SALE: Mellow Ventures LLC - Premier Eco-Tour & Luxury Houseboat Rental Company in the Florida Keys Step into one of the most unique lifestyle and income-producing businesses in the Florida Keys. Mellow Ventures LLC is a turnkey, multi-stream eco-tour and hospitality operation with a proven track record, established brand presence, and rare waterfront assets perfectly positioned for continued growth. Operating out of Key West, this boutique adventure company has built a reputation for intimate, sustainable experiences on the water—guided eco tours, private charters, island excursions, and custom adventures designed to showcase the natural beauty of the Lower Keys. In addition to its successful charter business, the sale includes two custom-built luxury houseboats, currently operating as high-demand short-term rentals. These floating suites offer a one-of-a-kind Airbnb experience that consistently generates strong occupancy and premium nightly rates. Each vessel blends modern comfort with an immersive waterfront setting, providing an unforgettable stay for guests seeking something truly special. Highlights Include: -Well-established eco-tour & charter business with brand recognition in Key West -24' Twin Vee -Two fully custom houseboats designed for nightly rentals -Strong Airbnb track record with exceptional occupancy -Multiple revenue streams: eco tours, private charters, overnight rentals -Turnkey operation with booking systems, media assets, furnishings & equipment -Excellent online reviews and repeat clientele -Ideal opportunity for owner-operator or investor seeking passive/managed income -Rare waterfront lifestyle business in a world-renowned destination This is a unique chance to acquire a thriving, experiential Keys business blending adventure tourism with boutique hospitality—a lifestyle investment that generates real returns.

Rat, Key West

$3,100,000

3 Beds ⋅ 2 Baths ⋅ 619319 MLS

A rare opportunity to own a stunning waterfront penthouse in the exclusive, gated Sunset Marina community--where luxury meets the effortless charm of Key West living. This exceptional 3-bedroom residence has been thoughtfully positioned to capture breathtaking panoramic views of the Gulf and marina, offering both sunrise and sunset vistas from multiple private balconies. On the Fourth of July, enjoy a spectacular fireworks display right from your own outdoor space--an experience few properties can offer. Inside, the home blends timeless elegance with modern upgrades. Rich white oak flooring runs throughout, complemented by fully finished doors and recessed lighting that create a warm, sophisticated ambiance. Expansive new impact-resistant windows invite natural light to pour in, enhancing the bright, open layout. The chef's kitchen is a true showpiece, designed by Hansen & Bringle of Key West, featuring sleek quartz countertops, premium Viking appliances, and refined custom finishes--perfect for both entertaining and everyday living. A wet bar with refrigerator adds an extra touch of convenience and style. The spacious primary suite offers a serene retreat, complete with luxurious details including onyx sinks, custom built-ins, and direct access to a private balcony. Every bedroom enjoys its own balcony, providing seamless indoor-outdoor living throughout. Additional high-end features include a whole-house water purification system with a double filtration system for drinking water, power shades on the porch, and thoughtfully curated furnishings for a move-in-ready experience. Residents of Sunset Marina enjoy resort-style amenities including a heated waterfront pool, clubhouse, elevator access, deeded parking, garage and guest parking, and private storage. Boat slips are available, offering quick access to world-class fishing and the pristine sandbars of both the Gulf and Atlantic.This residence offers the ultimate in island lifestyle.

5605 College Rd Unit # E305, Key West

$7,000,000

3 Beds ⋅ 3 Baths ⋅ 619242 MLS

Escape to Sunset Key, a private island sanctuary where refined elegance meets effortless tranquility. Just a four-minute ferry ride--operating 24 hours a day--from the vibrant charm in the heart of downtown Key West, this serene enclave offers the rare balance of seclusion and accessibility, keeping the energy of Old Town within effortless reach at any hour. This exquisite three-bedroom, three-bath beachfront home is thoughtfully designed to capture the essence of elevated island living. Wake to sweeping water views from the primary suite, and enjoy the same serene vistas from the main living area, where natural light and coastal beauty take center stage. Step outside to your private pool and spa, where you can unwind to the rhythm of waves lapping along the shoreline, all while enjoying gentle sea breezes and breathtaking sunsets over the Gulf of Mexico. The expansive main-level primary suite provides a tranquil retreat, while two beautifully appointed guest suites upstairs ensure comfort and privacy for all. Rich hardwood floors and natural stone finishes flow seamlessly throughout, complemented by a warm, sophisticated island aesthetic. Set within a private island enclave, Sunset Key offers access to exceptional amenities, including a gourmet waterfront restaurant, full-service spa, state-of-the-art fitness center, private beaches, tennis courts, and convenient ferry service. Perfectly positioned within minutes of Old Town Key West yet blissfully removed from the crowds, this secluded setting delivers a truly elevated lifestyle--where every detail is designed for quiet luxury and effortless escape.

5 Sunset, Key West

$1,949,000

2 Beds ⋅ 3 Baths ⋅ 616792 MLS

Experience ultimate elegance at Key West's Beachside Resort & Residences! This first-floor Condominium offers the perfect blend of luxury, flexibility, and investment potential. Featuring two transient licenses and a lockout configuration, this property includes both a Signature King Room and a Resort View Suite, which can be used together or separately for optimal rental income. The Signature King Room (283 sq. ft.) is an intimate, elegantly furnished retreat ideal for up to two guests. The Resort View Suite (1,074 sq. ft.) features an open floor plan with a designer kitchen equipped with Sub-Zero, KitchenAid, GE, and Bosch appliances, dual stainless-steel sinks, and custom cabinetry. The primary suite offers a spa-inspired bath with a sunken jetted tub, tiled shower, and dual vanities. Throughout the unit, you'll find 16-inch marble tile flooring, crown molding, and high-end finishes that elevate every detail. Fully furnished and beautifully decorated, this residence is designed for year-round living or part-time ownership—with the convenience of optional on-site rental management when you're away. All doors and windows are engineered to exceed building codes, rated for up to 175 mph winds, ensuring both safety and peace of mind. Resort-style amenities include a private beach, heated waterfront pool and spa, poolside bar & grill, gourmet restaurant, fitness center, valet parking, concierge services, on-site management, and the island's largest conference center. Positioned on open Gulf waters, this condo presents an extraordinary opportunity to enjoy the best of Key West luxury living—a perfect combination of personal enjoyment and investment performance.

3841 N Roosevelt Blvd Unit 315, Key West

$343,500

1 Beds ⋅ 1 Baths ⋅ 616493 MLS

IMPORTANT UPDATE TO NOTE: SELLER WILL PROVIDE A $5,000 CREDIT THAT CAN BE USED FOR CLOSING COSTS OR CONDO FEES!! Excellent as an investment, primary residence, second home, or rental property. This condo is conveniently located in a shopping area with easy access to Duval and US 1. It is one of the few gated communities in Key West with secure entry. You have ample parking, storage, pool, tennis court, laundry, on site management, etc. The unit has newer flooring, newer AC unit, updated electrical panel, updated kitchen, newer appliances, even impact rated hurricane windows & doors. Don't miss this opportunity.

3312 Northside Dr Unit 405, Key West

$1,949,000

2 Beds ⋅ 3 Baths ⋅ 616791 MLS

Experience ultimate elegance at Key West's Beachside Resort & Residences! This third-floor Condominium offers the perfect blend of luxury, flexibility, and investment potential. Featuring two transient licenses and a lockout configuration, this property includes both a Signature King Room and a Resort View Suite, which can be used together or separately for optimal rental income. The Signature King Room (283 sq. ft.) is an intimate, elegantly furnished retreat ideal for up to two guests. The Resort View Suite (1,074 sq. ft.) features an open floor plan with a designer kitchen equipped with Sub-Zero, KitchenAid, GE, and Bosch appliances, dual stainless-steel sinks, and custom cabinetry. The primary suite offers a spa-inspired bath with a sunken jetted tub, tiled shower, and dual vanities. Positioned on open Gulf waters, the Suites private rooftop sundeck provides a front-row seat to Key West's spectacular sunsets. Throughout both units, you'll find 16-inch marble tile flooring, crown molding, and high-end finishes that elevate every detail. Fully furnished and beautifully decorated, this residence is designed for year-round living or part-time ownership—with the convenience of optional on-site rental management when you're away. All doors and windows are engineered to exceed building codes, rated for up to 175 mph winds, ensuring both safety and peace of mind. Resort-style amenities include a private beach, heated waterfront pool and spa, poolside bar & grill, gourmet restaurant, fitness center, valet parking, concierge services, on-site management, and the island's largest conference center. This property presents an extraordinary opportunity to enjoy the best of Key West luxury living—a perfect combination of personal enjoyment and investment performance.

3841 N Roosevelt Blvd Unit 332, Key West

Key West Homes with Bay View

Newest Key West Homes with Bay View