Divider
Content Divider

Key West Condos on the Bay / Gulf Side of the Island For Sale

Total Listings 25
Order By:

$999,999
Key West
Hilton Haven Sec 2 A   - MM: 2.00
2 Bed, 2 Baths, 1,108 SqFt Days Listed: 33
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: 837
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: 26
-5.35% ($96,000) 1 Price Change : Last Change 4 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: 11
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: 11
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 04-17-2025.
Back To TopMore Info
Terms / Privacy / Accessibility ADA