Content Divider

Florida Keys Waterfront 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 Waterfront Florida Keys homes for sale below are on the gulf side / bay side.

Total Listings 148
Order By:

Lower Matecumbe
Safety Harbor   - MM: 74.00
3 Bed, 3 Baths, 3,805 SqFt Days Listed: 1350
-12.93% ($504,000) 18 Price Changes : Last Change 292 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin113ft.

Beyond compare, this Polynesian inspired exquisite keys waterfront Harum designed custom home is complete. 3 bedrooms 3 and a half baths with additional office that could be 4th bedroom, pool, exquisite landscaping, 110ft plus deep water dock w/shore power, Lutron system with Onos Sound throughout. Marvel at the vaulted beam tongue and groove cathedral ceilings throughout and custom designed kitchen and living area opening up to a massive covered pavilion for entertaining in addition to the enormous covered entertaining and living area on ground level where you will also find sports and storage rooms and 2 separate car garages for boats or vehicles. Located on Hurricane Creek this residence offers deep water draft up to 6 ft with unlimited beam with easy access to Gulf, Bay and Atlantic.

Shark Key
Shark Key   - MM: 11.00
7 Bed, 7 Baths, 6,800 SqFt Days Listed: 971
-23.26% ($1,500,000) 2 Price Changes : Last Change 499 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Sophisticated & understated Shark Key home spread over 3 open water lots, on 1.5 acres, is built in timeless style & beauty. Plantation style, one level design is elegantly minimal yet luxurious with a living area featuring vast frontages that make the most of the views of the water. An extensive restoration was just completed with a brand-new kitchen & all new bath rooms. Lime stone floors, mahogany doors through-out, reclaimed cypress and oiled bronze hardware are a few of the elegant materials used & all built 11 ft over grade. 6800 SF w/ beautifully scaled rooms, 12 ft ceilings, custom 8ft doors & an abundance of indoor & outdoor dining areas. This home makes the ideal setting for an unforgettable experience, offering a combination of privacy & relaxation. Walk the Key stone accented

Grassy Key   - MM: 58.00
9 Bed, 9 Baths, 7,006 SqFt Days Listed: 727
-7.55% ($200,000) 10 Price Changes : Last Change 216 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin,Davits

Gulf front estate located on exclusive Morton Street in Grassy Key, this 2.82 Acre property offers six individual living units plus a large storage garage. The main house has expansive open water Gulf views with three bedrooms, three bathrooms, soaring ceilings and granite kitchen. Private boat basin and salt water pond. Additional homes include a 2/1 separate living unit below main house, 2 bed/2 bath CBS cottage and separate 1/1CBS cottage with metal roofs. A 1600 sq ft apartment over the storage garage and a 1 bed, 1 bath efficiency

Plantation Key
Misc Plantation Key   - MM: 85.00
6 Bed, 6 Baths, 6,573 SqFt Days Listed: 703
-10.58% ($1,005,000) 2 Price Changes : Last Change 90 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin

Opulent, alluring and meticulously detailed, this Islamorada Estate is where perfection meets the Bay ~ welcome to The Fish Ranch. Located on Plantation Key, The Fish Ranch estate features two (2) single family residences plus a media house, and cabana with outdoor kitchen. World-class designs make this one of the more distinguished estates for the most discriminating buyer. Elevator shaft, 100 swimming pool with two beach entries, hot tub, 250 of sandy beach, putting green, dockage, architectural designed landscaping with fire pit and lighting throughout. Also included with this property is an additional 19,729sf lot.

Key Largo
Buccaneer Point   - MM: 98.00
4 Bed, 4 Baths, 5,038 SqFt Days Listed: 688
-10.84% ($450,001) 2 Price Changes : Last Change 435 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Upon walking through the artist-designed custom copper front door its obvious that the finishes and features of this property were done to a gold standard. The timeless and classic travertine marble floors throughout give the homes modern architecture a luxurious feel. The breathtaking views center on the coveted Florida Bay, and sweep 180 degrees to Key West. Setting a new benchmark for luxury in bayfront real estate, 31 North Bounty Lane showcases meticulous craftsmanship. The Neff-designed kitchen, while sophisticated and functional, is equipped with high-end Thermador appliances including an induction glass cooktop, double refrigerator, wine chiller, and double oven. Other features include a glass tile backsplash, exquisite green pebble granite, and a walk-in pantry.

Big Torch Key
Misc Big Torch Key   - MM: 28.00
3 Bed, 3 Baths, 4,166 SqFt Days Listed: 589
-3.13% ($50,000) 1 Price Change : Last Change 450 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 400ft.

Great privacy,spectacular sunsets and stellar boating are waiting for your enjoyment! Please come visit this gated, estate quality, open water home boasting 3.5 acres with over 450 of shoreline. It abuts 60 acres of protected land and is off from the roadway for peace and quiet, no road noise. It is truly a home to get away from it all!The main house consists of 3 bed/2.5 bath upstairs with 2 screened porches overlooking the open water of Niles Channel and western skies above Little Knockem Down. Below is additional living space with terrazzo flooring throughout. There is a detached 4 car garage with workshop and additional living space above.

Palm Island   - MM: 48.00
7 Bed, 7 Baths, 6,432 SqFt Days Listed: 570
-17.74% ($2,750,000) 1 Price Change : Last Change 321 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Slip

Private bayfront island situated in the heart of the Florida Keys. Nestled behind gates and lush tropical landscaping are a magnificent main house and two private guest houses, a swimming pool, and deep water protected dockage for multiple boats. The island-style two-story main home offers two inviting bedrooms, a spacious living and dining area, a showcase kitchen, and French doors that open to lovely first and second floor porches overlooking the bay. The impressive guest quarters provide comfort and privacy with four bedrooms, four bathrooms, and a private patio with bay views. An additional one-bedroom guest cottage offers open bay views and a sandy beach area. The swimming pool with sundeck is surrounded by swaying palm trees and tropical gardens

Big Torch Key
Dorns Subdivision   - MM: 28.00
2 Bed, 2 Baths, 1,296 SqFt Days Listed: 531
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 200ft.

Stunning views abound from this waterfront estate on serene Big Torch Key. Enjoy living the Keys lifestyle with world-class fishing, boating, and snorkeling right outside your home. Designed to embrace the natural beauty of the surroundings, this two bedroom, two bathroom home has ocean views from the open living area. The split floor plan allows for privacy and also includes a convenient laundry room. Downstairs, there is a two-car garage and a utility room to easily store an abundance of water toys. Situated on over one acre, the sale will also include the vacant lot next door giving the new owner over two acres of waterfront property. Currently registered as a legal vacation rental, a new owner may apply for a license to rent as well. Truly an extraordinary opportunity.

Lower Matecumbe
Port Antigua   - MM: 74.50
10 Bed, 10 Baths, 4,264 SqFt Days Listed: 502
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip100ft.

Stunning ocean views, protected dockage, quick ocean and bay access for virtually any size boats, and room for all of your family and friends, as well as rental income... what more could you ask for? This stunning property is perfect for large families, corporate retreats, and investors looking for return on investment. With over 100 feet of brand new Ipe wood dock for your offshore yacht, large center console, bay boat, skiff, and all of your water toys, this newly renovated property totals 10 bedrooms and 6 bath in two sides separated into four living areas, with 4 kitchens and 2 laundry rooms. The options are limitless. The hurricane impact windows and doors and new metal roof make this property perfect for carefree living. A must see to truly appreciate.

Stirrup Key Subdivision   - MM: 52.50
4 Bed, 4 Baths, 2,800 SqFt Days Listed: 495
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp

Keys coastal living with unobstructed open water views and spectacular sunsets. Located in exclusive, gated Community of Stirrup Key. This home was completely rebuilt in 2015! Brand new pool with tropical landscaping, workshop area with cabana off the pool area with legal downstairs bathroom. Chef grade kitchen with stainless steel appliances, granite countertops, large central island, custom cabinetry, and an A/C walk in pantry. Private office with its own private exterior entry. The master suite is an oasis with cathedral ceilings, large walk in closet, plantation shutters, spa bathroom, and separate air conditioning system. 3 guest beds all on the 2nd story, 2 have access to the lanai w/ open water views. The 2nd story owns A/C system along with with spa inspired bathroom.

Lower Matecumbe
Lower Mat Harbor   - MM: 75.00
4 Bed, 4 Baths, 4,610 SqFt Days Listed: 469
-5.66% ($450,000) 1 Price Change : Last Change 11 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Ramp,

Sea Garden is located on an impressive landscaped 1.5 acre bayfront parcel sprinkled with orchids and boasts a highly unique bayside coral reef right behind the docks. This completely solar powered home has been built to last and offers over 120 of deep water dockage with 13k boat lift plus kayak/paddleboard ramp and floating dock. Three car garage with upstairs guest house is an added bonus to this already impeccable estate. Watch the bald eagles fly by, the painted sky sunsets and enjoy the natural surrounding beauty of the Florida Keys right from your back porch!

Key Largo
Baywood   - MM: 104.00
5 Bed, 5 Baths, 4,099 SqFt Days Listed: 454
-8.18% ($245,000) 1 Price Change : Last Change 33 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 100ft.

Keys styling and modern layout on this new construction home with 180 endless bay views and sunsets right down the pike! Custom in every way, this home checks all the boxes with a grand entertaining area, 100 of dockage ready for 2 boatlifts and deep enough to accommodate larger boats, huge heated and chilled pool, double garage, elevator, rooftop deck, natural sandy beach, and more privacy than youll ever need. The main level features a spacious living room opening into the kitchen and 2 bedrooms and 1 1/2 baths. The 3rd floor stuns with a must-see master suite, and 2 more bedrooms with a Jack and Jill bathroom. The third floor balcony leads to a private staircase to the rooftop deck where you can view most of Key Largo. Have a front row seat to the boat parades and fireworks displays!

Sunset Key
Sunset Key   - MM: 0.00
4 Bed, 4 Baths, 2,480 SqFt Days Listed: 400
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Firs

Centered on idyllic Crescent Beach on world famous Sunset Key Island, the location of this four-bedroom, three-and-a-half bathroom home is the best of the best. The tastefully done interior features crown moldings throughout. Abundant windows and French doors with transoms bring in ample natural light and provide beach and water views. An additional office completes the homes spacious living areas. From the backyard, get a front row seat for the jaw-dropping Key West sunsets and relax around the beachfront pool. Come see this incredible home priced at an equally incredible value.

Little Torch Key
Mates Beach   - MM: 28.50
3 Bed, 3 Baths, 1,423 SqFt Days Listed: 398
-1.49% ($10,900) 1 Price Change : Last Change 122 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Bring all of your toys & admire gorgeous sunset views over the salt ponds from this 3 BR, 2 BA waterfront home boasting a colossal 1,500 sq. ft. attached 3-Car Garage on Little Torch Key. As you enter the home through the interior Foyer & stairway from the Garage you arrive to the Great Room featuring soaring ceilings, open Kitchen w/large bar for entertaining & a screened wrap-around Porch, all w/picturesque views of the water. Enjoy Easy & Quick Ocean & Gulf access from the composite Dock w/Boat Lift that is just minutes to world-class fishing & diving and the public boat ramp. The 7,754 sq. ft. property offers pretty paved pathways & driveways & lots of lush tropical landscaping. Easy to maintain with a new metal roof, Hardiboard siding, & accordion shutters. Furnishings negotiable.

Big Coppitt
Similar Sound Subdivision   - MM: 10.00
5 Bed, 5 Baths, 1,830 SqFt Days Listed: 362
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Concrete

Dont miss this opportunity for a large waterfront home awaiting your renovation ideas. Expansive living area, oversized canal lot, covered parking, and concrete seawall. Get your slice of paradise!

Big Pine Key
Port Pine Heights   - MM: 29.00
2 Bed, 2 Baths, 1,123 SqFt Days Listed: 360
-8.60% ($40,000) 3 Price Changes : Last Change 55 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 50ft.

2 Bedroom, 2 Full Bathroom canal home in quiet neighborhood. Front foyer entry with interior stairs to upstairs. Irma repairs: New carpeting, new shingle roof, AC, vinyl siding. Sewer hookup complete, fenced yard, concrete dockage, garage, 421 sq ft downstairs enclosed storage.

Big Pine Key
J R Matthews Properties   - MM: 30.50
2 Bed, 2 Baths, 2,579 SqFt Days Listed: 354
-1.92% ($24,000) 1 Price Change : Last Change 107 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits

This custom built home, designed by the current owners, sprawls over a 15,525 sq. ft. Gulf Front lot boasting gorgeous endless views of the open water. Perfect for entertaining with over 2,500 sq. ft. including a colossal Great Room featuring high ceilings, oak hardwood floors and an open chefs Kitchen with center island & stainless appliances. Cocktails or relaxation are a must on the 1,100 sq. ft. wrap-around Porch overlooking the water. The 2nd Story is all Master Suite and includes a large Bath, his/her walk-in closets & Porch for enjoying morning coffee with a view. Room for all of your toys at the concrete Dock w/Davits or in the large detached 2-Car Garage. Easily maintained pearock yard with lots of tropical landscaping complete this magnificent home.

Plantation Key
Venetian Shores   - MM: 86.00
3 Bed, 3 Baths, 2,254 SqFt Days Listed: 353
-6.60% ($99,000) 2 Price Changes : Last Change 80 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davit Pads,Davits70f

Premier Waterfront Neighborhood, Venetian Shores! Custom built, solid concrete construction home with newer metal roof, featuring 2254 sq. ft. of living area, offering 3 bedrooms, 3 baths, there are 2 bedrooms and 2 baths on the upper level plus a separate entry very spacious guest quarters on the lower level with large living room area, spacious bedroom, full bathroom, kitchenette, separate A/C with sliding doors that lead to the inviting patio and dock. Upper level features a beautiful custom cabinetry kitchen high end stainless appliances & solid granite counters. Master suite boasts water views, beautiful marble shower, & dual custom closets. Other features include new hurricane impact windows and sliding doors (upper level) recessed lighting, travertine tile, crown moldings

Big Pine Key
Grieser Subdivision   - MM: 31.00
2 Bed, 2 Baths, 952 SqFt Days Listed: 347
-2.75% ($10,700) 3 Price Changes : Last Change 22 Days Ago
Mobile Home - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits70ft.Concrete

Quick boat access! If you love to fish and get out on the water, it doesnt get much better than this for the price. A mobile home replacement in 1991, this 952 sq. ft., 2BD/2BA manufactured home was updated with Hardie-plank siding, metal roof and new windows. Abundant built-in cabinets provide always-needed storage space. The CBS detached garage is a bonus! The 70 x 75 ft. lot offers 70 ft. of canal-frontage and concrete seawall. Boat davits need new motors, As-Is. Canal was cleaned as part of Monroe Countys Canal Restoration project. Check out the walk-through video.

Plantation Key
Venetian Shores   - MM: 86.00
3 Bed, 3 Baths, 2,047 SqFt Days Listed: 328
-5.02% ($70,000) 1 Price Change : Last Change 83 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Davits70ft

Boating Dream! Canalfront home in Islamoradas premier boating neighborhood, Venetian Shores. Enjoy immediate ocean AND bay access from this move-in ready, all concrete updated 3/3 home with a 70 ft. concrete dock, 14,000 lb boat lift, 30 amp electric service at the dock, and davits for your second boat! The Snake Creek drawbridge opens oceanside for tall fishing towers and the canals in Venetian Shores also offer 100 ft. of width to allow for docking wide-beam vessels. Upstairs is a spacious 2/2 with updated kitchen and baths plus wide screen porch overlooking the water. Downstairs is a separate 1/1 guest suite (well above flood and permitted) plus an air conditioned storage/workshop/tackle room. Spacious back yard with room for a pool! Must see to appreciate.. call today!

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 09-28-2020.

Broker's Edge Realty
92300 Overseas Hwy Suite 303
Key Largo, Florida 33070

1(800) 692-3605
Contact Us

Back To TopMore Info
Terms / Privacy / Accessibility ADA