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Key West Waterfront Condos on the Bay / Gulf Side For Sale

Most of the properties in the Florida Keys peninsula are either on the bay / gulf side or on the ocean side of the island. The following Waterfront Key West condos for sale below are on the gulf side / bay side.

Total Listings 13
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$749,000
Key West
New Town Unlisted   - MM: 2.00
2 Bed, 2 Baths, 1,357 SqFt Days Listed: 134
-6.26% ($50,000) 1 Price Change : Last Change 35 Days Ago
Condotel - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

Experience Ultimate Elegance at Key Wests Marriott Beachside Resort. This offering includes two luxurious, fully furnished units--a Signature King Room and a Resort View Suite--each designed to deliver an exceptional blend of comfort and sophistication. Together, they provide flexibility as a full-time residence, vacation retreat, or income-producing rental property with two coveted TRANSIENT RENTAL LICENSES and a strong rental history.The Signature King Room, spanning 283 sq.ft. is an intimate retreat ideal for accommodating up to two guests. It features elegant finishes, high-end furnishings, and stunning attention to detail, making it a perfect haven for relaxation. The Resort View Suite, generously sized at 1074 sq. ft, can comfortably accommodate up to four guests. Its open floor plan includes a designer kitchen with a Subzero refrigerator, KitchenAid stove, GE microwave, range hood, Bosch dishwasher, dual stainless-steel sinks, and garbage disposal, all accented by crown molding and baseboards. The dining area is illuminated with dimmable lighting, creating the perfect ambiance for gatherings. The primary suite is a sanctuary with a sunken jetted tub, tiled shower stall, and dual vanities, while 16-inch tile flooring extends throughout, adding a refined aesthetic. Resort living is elevated with access to a private beach, a heated waterfront pool and spa, and a poolside bar and grill. On-site gourmet dining, valet parking, and concierge services are available to meet your every need, with optional on-site rental management providing a seamless investment opportunity. The secured building includes a garage and assigned parking for convenience and peace of mind. Positioned on open Gulf waters, the propertys private sundeck provides panoramic views, offering the perfect backdrop for serene mornings or captivating sunsets. This property is an extraordinary opportunity to embrace the best of Key West living.

$834,000
Key West
New Town Unlisted   - MM: 2.00
1 Bed, 1 Baths, 814 SqFt Days Listed: 49
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Experience the epitome of beachfront living at the Key West Beachside Resort and Residences! This stunning corner suite invites you to live like youre on vacation every day. 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--perfect for creating culinary masterpieces. 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 resorts world-class amenities await, including a restaurant, bar, pool, spa, and fitness center. The on site parking garage includes one deeded parking space. This superb property offers incredible flexibility: use it as your private getaway, generate income through the onsite rental program (no maximum stay restriction for owners!), or both! Dont miss this prime opportunity to own a piece of paradise!

$845,000
Key West
The Halyard   - MM: 2.00
2 Bed, 2 Baths, 1,136 SqFt Days Listed: 134
-13.33% ($130,000) 7 Price Changes : Last Change 37 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Boat

Attention Watercraft Lovers: Escape to Paradise with this beautiful TURNKEY condo with its exclusively DEEDED BOAT SLIP, perfectly situated on the Gulf of Mexico just minutes to your favorite fishing hole or sand bar! Each dock has its own water, and there is a fish cleaning station ready for your fresh catch. Why pay dockage feees when you can own one?The modern open-concept living space features abundant natural light with three sets of French Doors leading to your private balconies. There is plenty of closet space, for each of the two bedrooms, with an additional storage area and a bonus turret room just off the great room that can suffice as a third bedroom or office or exercise room. And new central A/C, new hurricane shutters and brand new roof!Relax and unwind in the sparkling community pool overlooking the water, or enjoy your private sandy beach for picnics and gatherings with neighbors and friends. Whether youre seeking a vacation getaway or a permanent slice of paradise, this condo has everything you need to live the coastal lifestyle. Dont miss out on this rare opportunity!

$875,000
Key West
New Town Unlisted   - MM: 2.00
2 Bed, 2 Baths, 1,357 SqFt Days Listed: 14
Condotel - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges

Step into the world of luxury living at Beachside Key West, where you can own a piece of paradise that functions as both a high-end resort and a private retreat. This exceptional condotel unit offers the rare flexibility of full-time residency or a lucrative vacation rental opportunity.Designed for ultimate convenience, the unit features a versatile two-part layout. The main suite is a spacious one-bedroom, one-bath residence with a fully appointed kitchen, a generous open-concept living area, and a welcoming foyer. The lockout suite, accessible from the foyer, is a private one-bedroom, one-bathroom retreat, allowing for independent rentals or expanded personal space. Unlock the connecting door, and the unit transforms into a seamless two-bedroom, two-bath home, perfect for family vacations or maximizing rental potential. Perfectly positioned within the resort, the unit boasts tropical views of the pool and spa area right from your private balcony. A charming spiral staircase provides direct access to the pool and spa, placing relaxation just steps away from your door--an unmatched convenience for you or your guests.Fully furnished with elegant decor, high-end appliances, and resort-style amenities, this turnkey investment ensures both comfort and profitability.Located at the entrance to Key West, Beachside offers unparalleled access to world-class dining, shopping, and entertainment. The property features on-site restaurants, a marina with rentable boat slips, and premium resort amenities, ensuring an effortless coastal lifestyle. Whether youre dreaming of living in a luxury hotel year-round or securing a high-yield investment, this condotel unit offers the best of both worlds. Your Key West escape starts here!

$899,000
Key West
New Town Unlisted   - MM: 2.00
2 Bed, 2 Baths, 1,357 SqFt Days Listed: 156
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

Discover the ultimate fusion of luxury and part time usage with this transient-licensed, 2-bedroom, 2.5-bath condo in Key West. Perfectly suited for vacation rentals, it offers the flexibility of a personal coastal retreat and a robust source of passive income. Fully furnished with sleek, modern decor, high-end appliances, and refined details throughout, this turnkey property is ready to impress guests and owners alike from day one. Situated in the entrance to Key West, the condo provides easy access to a lively array of shops, restaurants, entertainment, and the beautiful waterfront and beaches just moments away. Designed for seamless rental management, this property maximizes returns with minimal effort, making it ideal for buyers seeking consistent income or anyone desiring an elegant island escape. Two onsite restaurants as well as a small marina where slips can be rented while you are in town. The beauty of this particular unit is that is is setup with 1BR/1BA as a lockout unit so you can rent one side for the other while still being able to use your vacation home yourself. Embrace the best of Key West living--your island getaway awaits!

$995,000
Key West
Hilton Haven Sec 2 A   - MM: 2.00
2 Bed, 2 Baths, 1,114 SqFt Days Listed: 77
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Great location to all Key West has to offer on this waterfront 2 bedroom, 2.5 Bath Condo townhouse in Bay Villas. Great sunrise views from both first floor and second floor decks. Quiet, private location at the end of Hilton Haven Road. Enjoy the waterfront community pool and assigned parking just outside your front door. The first floor features the kitchen, half-bath and living area with wide open views of the water. Upstairs are the primary and guest bedrooms, each with private bathrooms. Impact windows and sliding doors.

$999,000
Key West
New Town Unlisted   - MM: 2.00
3 Bed, 3 Baths, 1,586 SqFt Days Listed: 156
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

Enjoy unparalleled flexibility and luxury with this transient-licensed 3-bedroom, 3-bathroom condo, an exceptional opportunity for a personal coastal escape or a versatile vacation rental. Fully furnished with modern decor, high-end appliances, and meticulous craftsmanship, this turnkey property is poised to impress from the moment you step in. Conveniently located at the entrance to the island of Key West, it offers seamless access to a wealth of shops, dining, entertainment, and recreation options, delivering convenience and enjoyment at every turn. With its streamlined rental setup, this condo is perfect for buyers seeking potential income or for those desiring an upscale island retreat all to themselves with all the amenities one could possibly ask for. Property has two restaurants, a bar, covered parking, mini marina dockage for boating while visiting and a fitness center all on site. Experience the best of refined island living!

$999,900
Key West
The Halyard   - MM: 2.00
2 Bed, 2 Baths, 1,045 SqFt Days Listed: 73
-9.02% ($99,100) 2 Price Changes : Last Change 26 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip24ft.

KEY WEST mid town open water 2/2 gem boasting an open floor plan offered turnkey with new furnishings and a deeded 12 X 24 gulf side boat dock. Hilton Haven is a unique neighborhood located mid island on a strip of land that offers a mixed use of waterfront properties on each side. This 8 unit condominium complex is at the end enjoying peace and quiet and also has its own private white sand beach and waterfront pool. Many extras to be enjoyed including tile floors throughout, 2 balconies offer both waterfront and sunset views and an abundance of closet space plus a designated generous storage room for all of your beach/water toys. Property was recently enrolled in a professional monthly vacation rental program. All of this within the city limits of Key West where you will find both nightlife, easy airport access and all of your shopping needs a bike ride or short drive away.

$999,999
Key West
Hilton Haven Sec 2 A   - MM: 2.00
2 Bed, 2 Baths, 1,108 SqFt Days Listed: 31
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Remarkable Waterfront Retreat- 32 Hilton Haven #9, Key West, FLWelcome to an exclusive waterfront sanctuary in the private community of Bay Villas in Hilton Haven. This beautiful 2 bedroom, 2.5 bath residence offers direct water views making it a rare gem in Key West.The primary suite boasts panoramic water views and balcony. The peaceful setting is just minutes from Old Town Key West, This home is ideal for those seeking the ultimate island lifestyle, Whether as a full-time residence, vacation getaway or investment opportunity, 32 Hilton Haven #9 is a rare find . Schedule your private showing today...

$1,300,000
Key West
Harbour Lodge   - MM: 2.00
2 Bed, 2 Baths, 1,351 SqFt Days Listed: 835
Condo - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock26ft.

Closest living to OLD TOWN with a boat slip!! Peace and quiet and a boaters delight! This small condo complex located in the beautiful Meadows neighborhood has an ordinance against vacation rentals which ensures consistent tranquility with a virtually private pool. One of the only properties close to Old Town where you can keep your boat in the water with an assigned boat slip. With the rising cost of boat slips and marina rates, the slip can save you upwards of a $1000 per month. This third floor 2BR/2BA unit allows for panoramic views of the marina and Key West. The property has had many upgrades during this ownership including new decorative floors with a coastal feel, an upgraded bathroom, new AC, washer and dryer, and some appliances. Enjoy entering a cool car with the covered parking, a rare find in The Meadows. Large private exterior storage space is included. The views are a must see!

$1,699,000
Key West
Roosevelt Annex   - MM: 2.00
3 Bed, 3 Baths, 1,320 SqFt Days Listed: 24
-5.35% ($96,000) 1 Price Change : Last Change 2 Days Ago
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Key West Waterfront Paradise - Private Dock & Pool!Welcome to one of the most exclusive waterfront homes in Key West, located in the prestigious gated community of Gulfview Pointe. This rare gem is one of the few properties in Key West offering both a private dock and private pool, making it the ultimate island retreat!Step inside to an open concept living and dining space, where ocean views of the Gulf from your living room create a breathtaking backdrop. The gourmet kitchen is a chefs dream, featuring granite countertops, stainless steel appliances, and coastal wood cabinetry.Through French doors off the living room, step out onto your expansive back patio--a private oasis with a covered seating area, grill, sparkling pool, and direct access to your private dock. Whether youre hosting sunset dinners, enjoying a swim, or casting a line off your dock and reeling in a fish, kayaking, or paddleboarding, this outdoor space is designed for effortless island living.With 3 bedrooms and 3 full baths, this home offers ultimate comfort. Both upstairs bedrooms feature en suite baths and private balconies, perfect for enjoying morning coffee with Gulf breezes.Located just a 15-minute bike ride to Duval Street, youll enjoy the best of Key West: secluded waterfront serenity with quick access to the islands top dining, nightlife, and attractions.Investment Highlights:*Prime vacation rental potential in a sought-after waterfront community*High demand for luxury Key West rentals* Move-in ready with high-end finishes and modern amenities*Low-maintenance tropical landscapingAdditional Perks:*Covered parking + guest parking*Gated community for privacy & security*Launch pad for kayaks & paddleboards*Fish off your private dock and soak in the island lifestyleThis is a rare opportunity to own a true Key West waterfront treasure! Contact us today to schedule your private showing today!

$1,949,000
Key West
New Town Unlisted   - MM: 2.00
2 Bed, 2 Baths, 1,357 SqFt Days Listed: 9
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

Condo living with hotel caliber amenities, this first floor Beachside Condominium unit has it all. 2BD/2.5BA, w/ lockout & 2 transient licenses for optimal rental potential. Owners can live in this magnificent condo year round or part of the year & rent it when not in town. Beautifully appointed w/ gourmet kitchen, marble floors, fully furnished & stylishly decorated. All doors & windows are designed to exceed building codes & rated for 175 mph winds. On-site resort amenities include private beach, heated waterfront pool, spa, poolside bar/grill, valet parking, concierge, on-site management company, gourmet restaurant & the islands largest conference center.

$1,949,000
Key West
New Town Unlisted   - MM: 2.00
2 Bed, 2 Baths, 1,357 SqFt Days Listed: 9
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage,None

Condo living with hotel caliber amenities, this 3rd floor Beachside Condominium unit has it all. 2BD/2.5BA, w/ lockout & 2 transient licenses for optimal rental potential. Owners can live in this magnificent condo year round or part of the year & rent it when not in town. Beautifully appointed w/gourmet kitchen, marble floors, fully furnished & stylishly decorated. All doors/windows are designed to exceed building codes & rated for 175 mph winds. On-site resort amenities include private beach, heated waterfront pool, spa, poolside bar/grill, valet parking, concierge, on-site management company, gourmet restaurant & the islands largest conference center.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 04-15-2025.
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