Divider
Content Divider

Key West Homes 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 Key West homes for sale below are on the gulf side / bay side.

Total Listings 23
Order By:

$579,000
Key West
Key West Golf Club Dev   - MM: 4.00
2 Bed, 2 Baths, 780 SqFt Days Listed: 36
Townhouse - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

The 10 Best Priced Homes in Key West list welcomes a new addition! Competitively priced for only $579,000, dont miss out on this tremendous value located in the popular Key West Golf Club. This perfect move in ready townhome offers 2 bedrooms and 1.5 baths on 2 floors with a balcony off a bedroom and covered rear screened porch off the main living area, to take in the wide scenic view of the 1st and 9th fairways. Furnishings and most accessories are included in the sale, along with a complete suite of appliances. Notable features include beautiful hardwood flooring, crown molding, and storm shutters for windows and doors. A delightful fountain graces the front entrance with a decorative brick walkway and rear patio that complements the outdoor space. Just a few miles from Smathers Beach & Old Town, the KWGC is a private gated community on a public 18 Hole championship golf course, with no membership obligations. Affordable $510 mo. HOA fees cover 2 heated swimming pools, a fitness center, professional management of the community, security and internet/cable TV. Pets are welcome, making the KWGC a top choice for dog owners. Compare to other homes in the neighborhood to see why 133 Golf Club Dr. is such an incredible value!

$923,500
Key West
Key West Golf Club Dev   - MM: 4.00
2 Bed, 2 Baths, 1,120 SqFt Days Listed: 61
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Set in the coveted Sanctuary in the Key West Golf Club, this well-maintained, multi-level spa home is the retreat youve been searching for. The second floor includes two en-suite bedrooms and laundry, while the first floor features a convenient half bath and open concept kitchen, dining & living room, creating an ideal space for entertaining and everyday living. French doors open to a private, covered patio and spa, perfect for relaxing. This turnkey home is furnished with coastal-inspired decor and includes a convenient carport. Key West Golf Club residents have access to the large lagoon pool, a separate lap pool, clubhouse, fitness center, and gated security. Dont miss out on this move-in-ready home!

$1,140,000
Key West
Sunset Marina   - MM: 4.00
2 Bed, 2 Baths, 1,171 SqFt Days Listed: 39
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Scenic view of Sunset Marina, Key West, and the Gulf of America! Imagine retreating to the tranquility of this spectacular waterfront haven from the bustle of the tourist district of Key West, while still having all the excitement of our fun little island at your convenience. All this with boating possibilities at your doorstep and a nearby 18 hole golf course. The modernly constructed, open-concept 2 BR and 2 BA condominium offers volume ceilings, a large kitchen with a premium suite of appliances, and functionality rare to most Key West communities. Overlooking the picturesque marina, a private balcony serves as the centerpiece of the main living area, with additional access from the spacious master suite. In ideal condition, the home is ready for your immediate occupancy, allowing you to enjoy our famous winter weather without any delays posed by seller continued use or existing leases common during this high demand time of year. The manicured tropical setting of Sunset Marina features a private entrance, scenic boardwalk to enjoy leisurely sunset strolls, heated pool, hot tub, and clubhouse complete with a kitchen to cook your catch. With easy unit access to the elevator and stairs, covered parking and enclosed storage are assigned to the unit, with common areas handy for kayaks, scooters, and bicycles. Sunset Marina is a full-service marina with an ultra-modern concrete floating dock system offering direct open water access. Boat slips of all sizes are readily available for an additional purchase in the mid $200s. Whether you are an avid boater or simply enjoy the waterfront lifestyle, Sunset Marina provides the perfect gateway to the pristine waters of Key West.

$1,150,000
Key West
Old Town Unlisted   - MM: 1.00
2 Bed, 2 Baths, 1,700 SqFt Days Listed: 82
-26.98% ($425,000) 4 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

OLD TOWN CONCH HOUSE on a lovely Lane tucked away but close to all of your favorite shops, cafes and Key West attractions! First time on the market in over 45 years! This historic home built by the Roberts Family is located on a quiet cul-de-sac lane in Old Town Key West. Tucked away and just off Frances St, 608 Roberts Lane (formerly known as Cates Lane as well as Darwin Court dates back to the late 1800s. This is a classic Conch home with light filled rooms, Dade County Pine, and hard wood flooring is true Key West architecture. The main level with spacious foyer opens to the living room and separate kitchen with table space. There is a main level bedroom and full bath. The second floor boasts an expansive home office, art studio, possible 3rd bedroom, or lounge space along with primary bedroom and full bath. There is ample storage space with custom built-in closets throughout the upper floor. Low maintenance yard with tropical landscape, deck area is perfect for dining el fresco or relaxing in paradise. The shed has a full size washer & dryer along with room for tools. Absolutely charming home that has been owner-occupied and never used as a rental. This lovely gem of a home hidden in Old Town near fine dining, shopping and just blocks to famous Duval Street. Dade county pine, ductless central AC, tall ceilings, and a classic front porch & yard with picket fence all make this home the perfect island residence. Desirable X Flood Zone and low assumable flood insurance $809/yr! (Tax record shows year built 1933, home is shown on older Sanborn maps Circa 1899)

$1,159,000
Key West
Key West Realty Cos Subdivisi   - MM: 3.00
3 Bed, 3 Baths, 1,356 SqFt Days Listed: 144
+5.46% ($60,000) 2 Price Changes : Last Change 40 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Discover the ultimate in low-maintenance living with this charming, move-in ready single-level home, ideally located just a short stroll from the prestigious Key West Yacht Club, vibrant shops, top-tier restaurants, marinas, and the shimmering waters of the Gulf of Mexico. Enjoy the quintessential Key West lifestyle with easy access to beaches, downtown, and the islands endless attractions--all just a leisurely bike ride away.This rare gem boasts a spacious master suite with three closets, including a generous walk-in closet and two additional single closets for all your storage needs. A set of elegant French doors opens directly onto a serene back patio, creating a peaceful retreat that seamlessly blends with the private backyard, offering ample space for future enhancements like a pool.Built with durability in mind, this solid concrete block home features a metal roof that has withstood high winds with no damage, providing peace of mind for years to come. A tall privacy fence encircles the property, ensuring seclusion while still offering large side yard space for RV parking--a true rarity in this prime location.Dont miss this exceptional opportunity to own a slice of paradise in Key West!

$1,169,000
Key West
Pearlman Estates   - MM: 4.00
3 Bed, 3 Baths, 1,424 SqFt Days Listed: 50
-2.18% ($26,000) 1 Price Change : Last Change 5 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Price reduction!!! Welcome to your dream home in the heart of New Town! This bright and beautifully maintained CBS constructed residence offers a perfect blend of comfort and style. Step inside to find a generously sized renovated kitchen, featuring sleek stainless steel appliances, stunning granite countertops, and modern recessed lighting that creates an inviting atmosphere. The spacious living room boasts new impact-resistant glass doors that seamlessly lead you to your personal outdoor oasis. Dive into your heated or chilled pool, adorned with exquisite new tile, or relax in the beautifully landscaped, low-maintenance paver backyard, which offers plenty of seating options for entertaining friends and family. Additional storage is available with a large shed on the property. Nestled on a quiet street with ample parking, including a convenient circular driveway, this move-in ready gem is perfect for anyone seeking tranquility and elegance. Dont miss your chance to make this stunning home yours--schedule a viewing today!

$1,199,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 1,188 SqFt Days Listed: 162
-7.70% ($100,000) 2 Price Changes : Last Change 37 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Step into this bright and airy two-story single-family move in ready home nestled in the heart of Historic Old Town Key West. Boasting 3 inviting bedrooms, 2 baths, and an open floor plan with a spacious kitchen and dining or bonus room, this residence offers the perfect blend of comfort and entertainment space. With the added convenience of off-street parking for 2 vehicles and its prime location within walking distance to an array of restaurants, clubs, and the waterfront, this home presents a wealth of flexibility for your ideal living experience.

$1,345,000
Key West
Key West Golf Club Dev   - MM: 4.00
3 Bed, 3 Baths, 1,600 SqFt Days Listed: 35
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Discover your dream home in the prestigious Sanctuary at the Key West Golf Club. This 3-bedroom, 2.5-bath single-family residence overlooks the 18th fairway with a spacious private backyard.Inside, the open-concept floor plan offers bright and airy living spaces, including a flexible downstairs bedroom--ideal as a sitting area or office. The large kitchen includes a convenient half bath, while the generous living area opens through French doors to a large covered porch and private pool--perfect for entertaining and unwinding in a serene setting.Upstairs, two bedrooms share a covered balcony and full bath, while the expansive primary suite features a private en suite bath and its own large porch. Additional highlights include off-street parking for two vehicles and a carport.Located in a gated, private community, residents enjoy access to two resort-style pools, a fitness center, and 24-hour security.Dont miss this rare opportunity--schedule your private showing today!

$1,440,000
Key West
Old Town Unrecord   - MM: 1.00
3 Bed, 3 Baths, 1,296 SqFt Days Listed: 94
-3.36% ($50,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Now priced to sell with this $50,000 price improvement! Enjoy Key West living on one of our most picturesque Old Town lanes. Located in the heart of the historic district and near the seaport, everything you want in Key West is right out your door. Built in the early 1900s, over the years the home was converted into a legal 2-unit property with separate water & electric accounts, however easily returned to a single family residence. The current configuration is upstairs (large 1 BR & 1 BA with a sleeping loft) and downstairs (2 BR & 1.5 BA) units, with an exterior staircase. Both units have a front & rear porch, balcony, or deck. For your parking convenience, an off-street spot is in front of the property. Lease information available upon request. Competitively priced for just $1,440,000.

$1,450,000
Key West
Bay Manor   - MM: 3.00
4 Bed, 4 Baths, 1,778 SqFt Days Listed: 322
-13.43% ($225,000) 4 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

This is the perfect secluded island compound in Key West with POOL! Two detached homes make this ideal for an owner occupier to have rental income, employee housing, multi-generational living or as an income property. The main home is spacious and offers three bedrooms, two updated baths, central AC, laundry room, and kitchen is equipped with with stainless steel appliances. The primary bedroom suite offers large closet plus a walk-in closet and room opens to the lovely pool area. Additional bedroom has sliding glass doors opening to the expansive side fenced yard with tropical landscape. All three bedrooms are generously sized. Bonus screened in porch area for relaxing or entertaining. Surrounded by a privacy fence, the large pool area features plenty of outdoor space for poolside lounging, dining and hosting guests. The detached 1 bedroom/1 bath two story cottage makes the perfect guest space or rental unit with full kitchen, ductless AC units, and private gated entrance. Oversized lot allows for plenty of parking for your autos, boat, or RV. Shed and lots of storage space. Low maintenance artificial turf yard. Impacted rated windows and doors.

$1,450,000
Key West
Bay Manor   - MM: 3.00
4 Bed, 4 Baths, 1,778 SqFt Days Listed: 322
-13.43% ($225,000) 4 Price Changes : Last Change 2 Days Ago
Duplex - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

KEY WEST DUPLEX! This is the perfect secluded island compound in Key West with POOL! Two detached homes make this ideal for an owner occupier to have rental income, employee housing, multi-generational living or as an income property. The main home is spacious and offers three bedrooms, two updated baths, central AC, laundry room, and kitchen is equipped with with stainless steel appliances. The primary bedroom suite offers large closet plus a walk-in closet and room opens to the lovely pool area. Additional bedroom has sliding glass doors opening to the expansive side fenced yard with tropical landscape. All three bedrooms are generously sized. Bonus screened in porch area for relaxing or entertaining. Surrounded by a privacy fence, the large pool area features plenty of outdoor space for poolside lounging, dining and hosting guests. The detached 1 bedroom/1 bath two story cottage makes the perfect guest space or rental unit with full kitchen, ductless AC units, and private gated entrance. Oversized lot allows for plenty of parking for your autos, boat, or RV. Shed and lots of storage space. Low maintenance artificial turf yard. Impacted rated windows and doors.

$1,595,000
Key West
Old Town Unrecord   - MM: 1.00
2 Bed, 2 Baths, 1,260 SqFt Days Listed: 66
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Step back in time with this enchanting Key West cottage, built in 1899 and lovingly preserved through the years. This 2-bedroom, 2-bathroom home offers the perfect blend of historic charm and modern comfort. Both bedrooms are en-suite, with one conveniently located on the main level and the master suite spanning the entire second floor.The homes rich history is evident in the abundance of Dade County Pine, a hallmark of classic Key West architecture. Having only had five owners in its lifetime, this property has been carefully maintained and was honored with the prestigious Ceramic Star for restoration and preservation in 1996. Its also proudly listed on the National Register of Historic Places.The outdoor spaces are nothing short of magical. The lanai, overlooking a heated saltwater pool, is the centerpiece of relaxation and entertaining. Enjoy the soothing sounds of the pools water feature, surrounded by backlit palm trees and lush orchids and bromeliads; all kept vibrant with a drip irrigation system. A covered grill area and hammock invite you to savor lazy afternoons or festive gatherings.For additional versatility, the carport doubles as a cozy spot for lounging or entertaining. Inside, modern conveniences abound, including a new full-sized washer and dryer. Offered fully furnished, this home is truly move-in ready.Located in a highly walkable neighborhood, youll enjoy easy access to the best of Key Wests shops, restaurants, and attractions. Dont miss the chance to own a piece of Key West history with this unique and charming cottage. Schedule your private showing today and discover the magic for yourself!

$1,645,000
Key West
Old Town Unrecord   - MM: 1.00
2 Bed, 2 Baths, 1,421 SqFt Days Listed: 87
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Nestled in a quiet lane in Old Town Key West, this elevated 2-bedroom, 2-bathroom Conch house offers the perfect blend of historic charm and modern security. Perched high to protect against flooding, this home features a fully rebuilt foundation and substructure, providing both peace of mind and lower insurance costs.The house was meticulously renovated in 2006, adhering to FEMA standards and Historic Architectural Review Commn. guidelines. This award-winning transformation preserved the homes 1892 footprint while integrating modern upgrades for reliability and comfort.Inside, youll find warm Dade County Pine walls and vintage Bakelite doorknobs, paired with sleek, updated appliances and custom cabinetry. Practical upgrades include central air, new plumbing, and electrical systems. With off-street parking and a prime location near the Historic Seaport, Duval Street, and vibrant galleries, this home offers an unparalleled combination of Key West history and modern convenience.Dont miss the chance to own a piece of Key Wests rich history, with the added benefits of modern upgrades and elevated peace of mind. Schedule your private showing today to see how this charming home can be your perfect retreat or investment in one of the islands most sought-after locations.

$1,750,000
Key West
Old Town Unrecord   - MM: 1.00
2 Bed, 2 Baths, 759 SqFt Days Listed: 70
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Discover your dream surfers cottage on a tropical island! Built in 1918, this charming home still showcases elements of its historic architecture, blending timeless character with a unique coastal vibe. Located at 1020 Fleming Street in the Historic Seaport area of Old Town Key West, youll be just a short walk from amazing restaurants, great bars, and some of the best fishing and diving charters in the world.This rare gem has not been available on the market for nearly two decades and appears on the Key West map of 1848--dont miss the opportunity to make it yours. Start living your dream today. Call now!

$1,925,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 1,440 SqFt Days Listed: 143
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Experience the charm of Old Town living at 923 Eaton St, a beautifully updated historic home featuring three bedrooms and two full bathrooms, ideally situated just steps from the Historic Seaport and a short stroll to Duval Street. Offered turn-key, this property combines classic Key West architecture with modern enhancements, making it perfect for enjoying the local lifestyle.Inside, youll find Dade County Pine walls, hardwood floors, and renovated kitchen and bathrooms. The second floor boasts two inviting bedrooms, while the first floor offers a charming bunk room. Step outside to discover a spacious 10x20 ft heated saltwater pool and a private tropical backyard oasis, perfect for outdoor relaxation. Additional features include a newer metal roof, an impact-rated sliding glass door leading to the rear deck, and efficient ductless AC units.This charming home is fully furnished and ready for you to move right in or to generate a reliable income as an investment property, allowing you to enjoy all that Key West living has to offer!

$1,995,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 1,845 SqFt Days Listed: 115
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Beautiful 3 bedroom 2.5 bath home being offered Turn-key, perfect walking location to restaurants, historic waterfront, shopping and all the nightlife on Duval St . Spacious open floor plan for easy living and entertaining friends and family includes the ever important first floor bedroom, half bath and laundry room. Just off the kitchen/ dining area sneak out to the hot tub to relax, or outdoor patio for dining with plenty of shade and privacy. Back inside, make your way up the gorgeous staircase to the second level to find an oversized master bedroom with walk in closet and ensuite bath. The second floor also includes the third bedroom and second full bathroom! 400 White St is a home you wont want to leave ! Call today to schedule your private tour.

$2,375,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 1,444 SqFt Days Listed: 110
-3.06% ($75,000) 1 Price Change : Last Change 26 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Experience the quintessential Key West lifestyle in this beautifully transformed gem in the heart of Old Towns Solaris Hill. Restored and reimagined in 2022, this unique home seamlessly blends modern comfort with the historic charm of an 1889 cigar makers factory, as noted in Key West Sanborn maps. Enter through an inviting white picket fence to a spacious front porch, perfect for enjoying lazy afternoons with a cool drink or chatting with neighbors under swaying palms.Inside, a refreshing breeze welcomes you into an airy foyer with exquisite hickory hardwood floors, custom lighting, and a stunning locally crafted floating staircase that serves as a stylish focal point. The chef-inspired kitchen is the heart of the home, equipped with top-of-the-line Wolf appliances and a Sub-Zero refrigerator, all nestled in custom cabinetry with gorgeous soapstone countertops. An eye-catching iron and marble island takes center stage, surrounded by a handcrafted Cle tile wall that sets the scene for culinary adventures.Bright and inviting, the spacious living area features two sets of impact-rated French doors, enhancing the essence of indoor-outdoor living, where you can bask in the gentle sea breeze. Original Dade County pine adds warmth and character throughout. The retreat-like primary bedroom and two thoughtfully designed guest bedrooms offer ample relaxation space, each with beautifully upgraded bathrooms featuring custom tiles and Kohler fixtures.Step outside to your personal oasis, complete with a brand-new saltwater pool surrounded by tropical landscaping and a travertine deck, ideal for sun-soaked gatherings or starlit evenings. An outdoor shower adds a refreshing touch, while a custom-built privacy fence ensures your sanctuary from the outside world.Enjoy the convenience of private off-street parking and proximity to the vibrant culture, dining, and entertainment that Key West offers. Duval Street is just two blocks away, with nightlife and fabulous restaurants..

$2,895,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 1,916 SqFt Days Listed: 54
-3.34% ($100,000) 2 Price Changes : Last Change 4 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

In the heart of it all, here is a home you are sure to fall in love with. This luxury home offers the perfect blend of comfort and convenience, ideal for both vacationers and full-time residents. Boasting 3 spacious bedrooms and 3 modern bathrooms, it provides everything you need for a relaxing and enjoyable stay. The inviting front porch is perfect for people-watching, while the private pool offers a refreshing escape. With two off-street parking spaces, youll never have to worry about finding a spot.Its prime location means youre just a short walk from a variety of attractions, including restaurants, the harbor front, shopping, and exciting water activities. The home underwent complete reconstruction in 2018, ensuring it has all the modern amenities and style youre looking for. Whether youre here to relax or explore, this home offers it all.

$3,395,000
Key West
Martello Towers   - MM: 1.00
4 Bed, 4 Baths, 2,147 SqFt Days Listed: 24
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

1522 Georgia St., a stunning retreat that captures the iconic charm of Key West with a modern twist, offering a lifestyle of unparalleled luxury. Located one block from the islands beaches and Casa Marina District, this newly built residence is a perfect combination of timeless island elegance & contemporary sophistication.Four exceptional bedrooms, each a private sanctuary of comfort and style, boast spa-like en-suite bathrooms and spacious walk-in closets. Wrapped in a palette of serene, calming hues, these retreats are adorned with elegant Eastern Accent Linens, gorgeous window treatments and handcrafted wood shutters that invite the Island breeze. Stunning wallpaper, worthy of an Architectural Digest spread, adds a touch of artistry to every space, creating bedrooms that feel less like rooms and more like luxurious personal havens.Open floor plan where indoor and outdoor living blend effortlessly, creating a space for relaxation and entertaining alike. The gourmet kitchen, elegant dining area and inviting living rooms flow together with ease, all offering panoramic views of the majestic saltwater pool. Outside a serene waterfall cascades into the crystal-clear waters, while the sun drenched patio, glass railing and mature landscaping provide a private, resort-like escape - a true oasis where every days feels like a vacation.The Kitchen is nothing short of breathtaking, a masterpiece of design and function where every details has been meticulously curated. The designers eye for perfection is evident in the harmonious blend of colors, textures and finishes, all layered with stunning precision. At its heart, a spacious, statement-making Island invites both conversation and culinary creativity. Overhead, brass-covered light fixtures cast a warm inviting glow, perfectly complementing the gorgeous artful backsplash that adds that final touch.Additional features include, impact windows/patio doors, & off street parking.

$5,495,000
Key West
Sunset Key   - MM: 0.00
3 Bed, 3 Baths, 1,912 SqFt Days Listed: 12
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Here is the perfect Sunset Key island getaway home with stunning panoramic Key West Harbor and Gulf views. Lounge by your pool and spa or on your four covered porches with IPE decking while you enjoy the sites of open water where the Gulf meets the Atlantic. This home is in absolute mint condition with an open flow throughout. This 3 bedroom, 3 bath quality home needs nothing more. Elegant and comfortable finishes throughout, hardwood and tile flooring, whole house sound system, central alarm, impact windows and doors, luxurious built in cabinets and plantation shutters provide luxury, security and safety. Bonus features include a detached garage AND an electric cart. Accessible by a 24 hour dedicated ferry this island retreat has it all including a fabulous restaurant in Latitudes, relaxing Spa, private beaches, tennis courts and a fitness 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 03-09-2025.
Back To TopMore Info
Terms / Privacy / Accessibility ADA