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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 19
Order By:

$699,000
Key West
Key West Golf Club Dev   - MM: 4.00
2 Bed, 2 Baths, 810 SqFt Days Listed: 81
-1.27% ($9,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome to your tropical retreat at the Key West Golf Club! This updated 2-bedroom, 1.5-bathroom townhome offers a unique blend of comfort, style, and stunning views of the picturesque Hole #2.Property Highlights:Spacious Upstairs Bedrooms: Both bedrooms feature vaulted ceilings and access to private porches, creating serene outdoor spaces perfect for morning coffee or sunset relaxation.Fully Furnished & Turnkey: Move right in! This home is being sold as-is, fully furnished, providing a seamless and convenient transition for the new owners.Modern Upgrades: Enjoy brand-new HVAC, freshly painted interiors, new flooring, and sleek stainless steel appliances, offering a fresh and contemporary living experience.Outdoor Living: Expand your living space with multiple porches, including a downstairs tropical setting ideal for entertaining or unwinding in the Florida sunshine.Community & Amenities: Nestled within the Key West Golf Club Development, residents enjoy an array of first-class amenities, including:24-Hour Security: Feel secure with gated access and round-the-clock security services.Resort-Style Pools: Dive into relaxation with two heated pools, one featuring serene tropical waterfalls.Clubhouse & Fitness Center: Stay active and connected with an on-site fitness room and clubhouse facilities.Lush Landscaping: Stroll through beautifully tree-lined streets, surrounded by lush, mature landscaping that defines the islands charm.Additional Features:Customized Hurricane Fabric: Easy-to-install hurricane protection for all doors and windows ensures peace of mind during storm season.Dont miss this opportunity to become part of the vibrant Key West Golf Club community. Schedule your private tour today and experience the perfect blend of island living and modern convenience.The association fee is $510 per month--visit [KWGC HOA](https://www.kwgchoa.com/documents/) for detailed community association information.

$749,000
Key West
Key West Realty Cos Subdivisi   - MM: 3.00
2 Bed, 2 Baths, 1,450 SqFt Days Listed: 137
-10.73% ($90,000) 3 Price Changes : Last Change 21 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Nestled within the vibrant Mid Town neighborhood and offering a perfect blend of comfort, style, and island living. 2023 Staples Ave begins with a white picket fence framing the spacious front yard and a carport for convenient off street vehicle, golf cart or scooter parking. As you step inside you will discover a cozy and airy atmosphere, accentuated by the natural light, giving the space a warm and inviting ambiance. This charming 2-bedroom, 2-bathroom home has a bonus..., a huge multi purpose room located in the rear of the house with a separate entrance. Home office, additional bedroom, storage or a fun family room? The options are endless! Generous sized back yard could easily fit a swimming pool, and is completely fenced in with a covered patio, ready for outdoor dining, and lounging. 2023 Staples Avenue is centrally located in the desirable New Town neighborhood, and puts you within easy reach of Key Wests renowned attractions, including pristine beaches, eclectic shops, countless dining options, and vibrant nightlife. Dont miss your chance to experience the Key West lifestyle from the comfort of this delightful home!

$774,000
Key West
Key Cove   - MM: 2.00
2 Bed, 2 Baths, 1,120 SqFt Days Listed: 159
Townhouse - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Were pleased to present the opportunity to acquire a Rare gem property in a highly demanded Key West, FL. Including 2 bedrooms and 2 1/2 bathrooms, you are going to enjoy the 1120 sqft, built in 2002. 4 balconies with approx 486sq/ft of outdoor space. 700+ sq/ft garage. Updated floors, AC unit, appliances, bathrooms, garage door etc.. Nested in an enjoyable neighborhood, and minutes from local fun.

$899,000
Key West
Key West Realty Cos Subdivisi   - MM: 3.00
3 Bed, 3 Baths, 1,760 SqFt Days Listed: 65
-14.38% ($151,000) 2 Price Changes : Last Change 16 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome to your dream home in the heart of Midtown, Key West! This stunning 3-bedroom, 3-bathroom residence offers the perfect blend of modern comfort and tropical charm.As you step inside, youll be greeted by beautiful tile floors that run throughout the entire home, adding both elegance and ease of maintenance. The spacious and open living area flows seamlessly into the gourmet kitchen, which boasts top-of-the-line stainless steel appliances and ample counter space for all your culinary adventures.Each bedroom is generously sized, providing a serene retreat with plenty of natural light. The three full bathrooms are tastefully designed, offering convenience and luxury for family and guests alike. The third bedroom offers its own separate entrance and living situation. One of the standout features of this property is its private lot, offering peace and tranquility right in the heart of the city. The outdoor space is perfect for entertaining, gardening, or simply relaxing in the Key West sunshine. Youll also appreciate the convenience of off-street parking, a rare find in this sought-after location.This home truly has it all - style, comfort, and an unbeatable location. Dont miss the opportunity to make this Midtown gem your own!

$999,000
Key West
Pearlman Estates   - MM: 4.00
3 Bed, 3 Baths, 1,820 SqFt Days Listed: 89
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

New Listing! Welcome to this fabulous three bedroom/ four-bath 1800+sq ft home in New Town Key West just steps from Cozumel Park. Home offers a perfect layout for roommates, multi-generational living or employee housing! Currently configured with a renovated owner space including a large living room, dining room, & upgraded kitchen with stainless steel appliances/ample cabinet space plus a breakfast bar. This space also offers a spacious primary suite with stunning en-suite renovated bath and a generously sized walk-in closet. Central AC and updated flooring. The second bedroom is set up as an in-law unit with full bath, kitchenette, & living space with private entrance. Third bedroom currently used for storage offers a full bath en-suite with private entrance. Fenced rear yard with deck spaces to entertain or relax in the shade. Outdoor shower and outdoor sink for cleaning your catch of the day. Plenty of outdoor storage space with built-in sheds. Carport for easy parking. Home could easily be converted back to an open floor plan with access to all bedrooms from main home. Dont miss the opportunity to make this wonderful property your own!

$999,000
Key West
D T Sweenys Dia   - MM: 1.00
1 Bed, 1 Baths, 575 SqFt Days Listed: 243
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Nestled within the charming and storied streets of Key Wests old town, this exquisite property presents an unparalleled opportunity to own a slice of paradise in one of the most coveted locations in the Florida Keys. Located in the heart of the historic district, mere steps away from the pristine beaches and the vibrant entertainment scene of Key West. Enjoy the convenience of living within walking distance to Duval Street, the famous Mallory Square, and all the captivating sights and sounds of this charming island. Whether youre looking for a full-time residence, a vacation getaway, or an investment property, this beautiful Key West home offers it all. Live the island dream in a historic setting where every day feels like a vacation. This property is a true gem!

$1,295,000
Key West
Key West Golf Club Dev   - MM: 4.00
3 Bed, 3 Baths, 1,600 SqFt Days Listed: 183
-10.69% ($155,000) 2 Price Changes : Last Change 114 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

PRICED TO SELL! Owners are relocating! Seize the moment! Lights, camera, action! Beautiful single-family home in Exclusive Sanctuary (the gated community w/in the gates), prime location, cozy 1-way lane! Sparking, complete renovation! Freshly painted, luxury vinyl plank flooring, Plantation shutters, divine outdoor entertaining space, customized features. Pamper yourself w/private driveway/carport/electrical charging station. Rear yard has exterior lighting coming, low voltage lighting in front yard/carport installed. Upgraded Rain Machine Smart irrigation is coming! SimpliSafe alarm system/camera(s) & August Smart lock system. Picturesque front entry, beautifully landscaped, colorful plantings/pavers/stones. You are already home!!! Lots of natural lighting/taller ceilings/crown molding/ combination great room, perfect for entertaining. Kitchen is equipped w/new stainless GE Profile appliances, gorgeous waterfalls quartz countertop, large farm-style sink, upgraded cabinets, abundant counterspace/storage! Upgraded front load stainless washing machine/dryer concealed in the double closet w/organized storage. There is a den off the liv. rm., terrific office/study/exercise room (not included in the bedroom count, but could function as such). Handy powder rm. downstairs. French doors off the liv. rm. lead to Tropical Oasis! Spacious open veranda w/new Trex decking/steps, brick surrounding private pool, sand between your tootsies in the beach (ready to be transformed into a putting green)! Expansive vista along #18 fairway, view of lake, taller rear fence for privacy, landscaping buffer between your quiet neighbors! Life in the Slow Lane from both delightful rear verandas. Large Primary suite, high vaulted ceiling, en-suite bathroom, breezy, private open veranda. 2 guest bdrms. w/French doors & veranda overlooking streetscape. Many lovely inherent features! 24-hr. security, 2 terrific community pools. Elegant in Key West casual style.

$1,299,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 1,188 SqFt Days Listed: 7
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 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.

$1,500,000
Key West
Old Town Unrecord   - MM: 0.00
3 Bed, 3 Baths, 1,344 SqFt Days Listed: 225
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

This a real slice of Old Town charm, in a prime location in downtown Key West, located right off of Key Wests world-famous Duval Street. This mid-century home, built in 1969, was built by hand, according to the seller, and has been family owned since construction. Its perfect for vacation rental and in need of a little TLC. Comes with Off Street Parking. Dont miss the opportunity to own a piece paradise in heart of Old Town. Please text or call listing agent for showings and questions.

$1,550,000
Key West
Bay Manor   - MM: 3.00
4 Bed, 4 Baths, 1,778 SqFt Days Listed: 167
-7.46% ($125,000) 2 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.

$1,550,000
Key West
Bay Manor   - MM: 3.00
4 Bed, 4 Baths, 1,778 SqFt Days Listed: 167
-7.46% ($125,000) 2 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.

$1,799,000
Key West
Key West Golf Club Dev   - MM: 4.00
4 Bed, 4 Baths, 1,600 SqFt Days Listed: 195
-5.27% ($100,000) 1 Price Change : Last Change 128 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Beautiful home located in the Sanctuary at the coveted gate community of Key West Golf Club. This unique property with views of the 17th fairway boasts with an oversized lot with a private pool, with new equipment and has been recently resurfaced. The pool and side yard are surrounded by an enormous deck offering ample outdoor space for relaxing or entertaining complete with sunshades. Lush tropical landscaping makes you feel that you are in an oasis while offering plenty of privacy. Upon entering you will see this home is ready to move in complete with furnishings. The upgrades are plentiful, complete with new luxury vinyl flooring, quartz countertops, fresh painting complete, stainless steel appliances and more. Screened porches off the living room and master bedroom offer additional outdoor living space with views of the lake and the golf course. 3 bedrooms are located upstairs, and a bonus room/den or office on the first floor. Convenient half bath downstairs leads to a private outdoor shower. Off street parking for two vehicles, one covered, additional parking spot prefect for golf cart, moped, bicycles. The community offers 24 hour manned gate, additional gates at the entry to the Sanctuary, two community pools and gym for residents. Security system in place for your convenience. Come and take a look at this home you wont want to miss this one.

$2,189,000
Key West
Old Town Unlisted   - MM: 1.00
4 Bed, 4 Baths, 1,494 SqFt Days Listed: 96
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Discover this hidden gem in Key Wests vibrant Historic Seaport area. This beautiful and rare home stretches from Eaton Street to Thompson Lane, offering multiple off-street parking spots through the large gates on the Lane. As you step inside, the very high ceilings immediately catch your eye--a unique feature in these traditional homes. Large custom barn doors provide privacy and add a touch of design to the front receiving room.The chefs kitchen boasts all the comforts within arms reach, with an open layout perfect for social meals and gatherings. Upstairs, three bedrooms (two en suite) offer ample space for family or guests. The ground floor features a charming one-bedroom attached studio--ideal for guests or a home office. An additional air-conditioned work/craft room adds to the homes uniqueness.French doors open from both the main house and the studio to a spacious backyard. Theres even room to add a pool, if desired, near the roomy back deck (the seller has already provided a quote). The wrap-around porches (1500 sq. ft.) are a dream, surrounded by lush landscaping in a serene setting. Impact windows and doors provide peace of mind and energy efficiency.This thoughtfully updated traditional Key West home combines comfort with old-town charm. Plus, its just steps away from great restaurants, shops, and amenities. A must-see!

$2,999,999
Key West
Old Town Unrecord   - MM: 1.00
6 Bed, 6 Baths, 2,294 SqFt Days Listed: 58
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome to 329 William Street, where timeless island charm meets modern comfort in the heart of Old Town Key West. With six luxurious bedrooms, each boasting en suite bathrooms and kitchen facilities, this historic gem offers unparalleled convenience and privacy. Whether you seek a tranquil retreat or an investment opportunity, this property beckons with its unique features. Prime Location: Situated just one block from the iconic Historic Seaport boardwalk and a mere three blocks from the vibrant energy of Duval Street. Rental Opportunities: Excellent opportunity for long term and/or employee rental possibilities. Expansive Lot & Outdoor Oasis: Spanning over 5000 square feet, 329 William Street boasts ample space for relaxation and entertainment. Take a refreshing dip in the large pool, sip cocktails at the inviting tiki bar, or bask in the serenity of lush tropical landscaping. The part of the property where the pool currently sits appears to have had a structure previously and would likely be considered a ROGO lot with development potential (buyer to verify). Historic Charm: Steeped in history and architectural beauty, the property exudes timeless charm and character. Immerse yourself in the rich heritage of Key West while enjoying modern amenities and comforts.Perfect for savvy investors or those simply seeking a slice of paradise to call their own, 329 William Street offers a rare opportunity to own a piece of Key Wests storied past while embracing its vibrant present. Dont miss your chance to experience the quintessential island lifestyle at the Seaport Inn.Transient licenses currently associated with the property do not convey with the sale.Duplicate listing MLS #609512 w/transient licenses.

$3,275,000
Key West
Benj Alburys Subdivisiond   - MM: 2.00
3 Bed, 3 Baths, 2,064 SqFt Days Listed: 13
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Indulge in the allure of Coastal living with this honored 2023 Historic Preservation Award winning home. Meticulously restored and updated in 2022, this residence epitomizes timeless elegance and relaxed sophistication. Situated on an expansive 5800 sq ft private corner lot.Step onto the welcoming front porch, complete with a classic Porch Swing and charming Bahama Shutters, epitomizing quintessential Key West charm. Inside, the living spaces blend traditional elements with tropical flair, featuring crisp white walls, Dade County Pine, and tall windows framing lush views of the Tropical landscape.The main floor boasts a thoughtfully designed layout, with a Primary Bedroom featuring a new Bath addition and spacious Walk-in closet, ensuring accessibility and privacy.An exceptional highlight of this home is its soaring dining room ceiling, creating an unmatched ambiance for dining experiences. Additionally, the Bonus Room serves as a versatile space, doubling as a Library and potential Fourth Bedroom, complete with a cozy Loft reading nook.The kitchen seamlessly merges Historic charm with modern convenience, showcasing custom Thomasville Nouveau cabinetry, a Nantucket Fireclay Sink, Calcutta quartz countertops, and premium Cafe and Miele appliances.Upstairs, two spacious Guest Bedrooms and full bath offer a tranquil retreat, providing luxury, comfort, and privacy for visitors. Outside, discover a Resort styled lush tropical oasis that seamlessly extends the homes inviting interior. Relax on the covered deck or by the 30x10 Saltwater pool, accompanied by a charming resident mermaid.A unique historic Decorative Roof metal trim, newly installed Carport with dropdown storage, Electric car charger, and Shower elevate the outdoor experience, offering an unparalleled Key West atmosphere. You will be drawn to exploring the charming courtyard with brick pathways, indigenous plants, fruit trees, and Peaceful moments at this beautiful Key West home.

$3,999,999
Key West
Old Town Unrecord   - MM: 1.00
6 Bed, 6 Baths, 2,294 SqFt Days Listed: 180
-4.74% ($199,001) 1 Price Change : Last Change 77 Days Ago
Multi-Units - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome to the Seaport Inn, where timeless island charm meets modern comfort in the heart of Old Town Key West. With six luxurious bedrooms, each boasting en suite bathrooms and kitchen facilities, this historic gem offers unparalleled convenience and privacy. Whether you seek a tranquil retreat or an investment opportunity, the Seaport Inn beckons with its unique features. Prime Location: Situated just one block from the iconic Historic Seaport boardwalk and a mere three blocks from the vibrant energy of Duval Street. Flexible Rental Options: With two transient rental licenses and four non-transient rental licenses, this property presents a myriad of rental possibilities. Excellent opportunity for vacation rentals or consider the long term and/or employee rental possibilities. Expansive Lot & Outdoor Oasis: Spanning over 5000 square feet, the Seaport Inn boasts ample space for relaxation and entertainment. Take a refreshing dip in the large pool, sip cocktails at the inviting tiki bar, or bask in the serenity of lush tropical landscaping. Historic Charm: Steeped in history and architectural beauty, the Seaport Inn exudes timeless charm and character. Immerse yourself in the rich heritage of Key West while enjoying modern amenities and comforts.Perfect for savvy investors, hospitality entrepreneurs, or those seeking a slice of paradise to call their own, the Seaport Inn offers a rare opportunity to own a piece of Key Wests storied past while embracing its vibrant present. Dont miss your chance to experience the quintessential island lifestyle at the Seaport Inn.

$4,995,000
Key West
Sunset Key   - MM: 0.00
3 Bed, 3 Baths, 1,916 SqFt Days Listed: 282
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Othe

Talk about views! This three-bedroom, three-bathroom waterfront home has incredible panoramic views of Key West Harbour and the historic waterfront. No expense was spared on this elegant Sunset Key residence. This house has it all, from hardwood and tile floors throughout, to a chefs kitchen with granite counter-tops, comfortable living and dining area, a covered outdoor patio, and an in-ground pool. Sunset Key Island is only three minutes from historic downtown Key west by an island ferry which runs 24 hours a day and leaves from the Opal Key Resort & Marina. Walk to one of the islands three beaches. Even though it is an off-shore island, Sunset Key Island has full city utilities and services, and amenities such as tennis, a full-service spa, and a gourmet restaurant.

$5,550,000
Key West
Sunset Key   - MM: 0.00
3 Bed, 3 Baths, 1,927 SqFt Days Listed: 223
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Othe

Talk about views! This waterfront property offers breathtaking panoramic vistas of Key West Harbor and the historic waterfront area. Additionally, it boasts beachfront and water panoramas from every room within the house. This dramatic and sophisticated residence spared no expense. The seller is a licensed Real Estate Agent.

$6,105,000
Key West
Old Town Unlisted   - MM: 1.00
5 Bed, 5 Baths, 3,342 SqFt Days Listed: 340
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

One of Key Wests most iconic historic homes, this property has an amazing story to tell. Built in 1869 in the classical Bahama-House style by noted carpenter Robert Watson. It was extensively remodeled in1902. More recently, and over a five-plus year period, it was painstakingly resurrected with a fanatical drive to recapture and display its historical attributes and seamlessly incorporate the latest modern technology and features. The result is a property embodying Old Key West with an understated elegance while providing the most advanced amenities demanded by a discerning buyer.A magnificent house in an incredibly special location, it affords a unique way to experience Key West.You are mere steps from our finest restaurants, world renown music venues, theaters and shopping.Yet, once you pass through the gates, you enter your own private oasis.This expansive property has a generous 3,342 square feet of living space. The stunning Great Room offers a seamless flow between the large living space, the gourmet kitchen, a spacious dining room and is open to the pool area through 18 doors. There are five ensuite bedrooms including first and second floor primary suites. Adjacent to the feature-rich pool is a luxurious self-contained guest cottage. To the front of the property is gated parking for three vehicles and a charging station for electric cars, golf carts and scooters. If you are looking for the best location to experience Key West coupled with the best in tropical livingthat Key West can offer, you must experience Key West from this property.

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 10-05-2024.
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