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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 280
Order By:

$419,000
Big Pine Key
Sands Subdivision   - MM: 31.00
1 Bed, 1 Baths, 441 SqFt Days Listed: 204
-16.03% ($80,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Concrete

Per Seller: Boaters Paradise! 3 minutes to open water with the ability to dock almost any big boat or multiple boats here! 50 of sea wall and there is 25x50 feet of owned sea bed so the potential to moor boats here is amazing. Huge catamaran sail boat or multiple center consoles backed in. Would be a great base for a fishing charter. This is a cozy, solid built home, not a manufactured or mobile home. No HOAs and save on insurance! Many parks and trails nearby. Wonderful, very quiet community and great neighbors. Come see what Big Pine has to offer: fishing, lobstering, kayak 10 minutes to sand bar from your house and watch turtles and dolphins! See manatees, endangered key deer and a variety of bird species. Amazing place to live! Make the most of Keys living! There is plenty of space for storage with a shed and place to park for a RV, boat trailer or multiple vehicles. Charming outdoor area for lounging and entertaining. Relax with a line in the water. Efficient and well equipped kitchen. Bathroom with shower and washer/dryer, on-demand water heater. Everything you need and nothing that you dont. Buy now with the ability to build in the future.

$425,000
Big Pine Key
Tropical Bay   - MM: 30.50
2 Bed, 2 Baths, 654 SqFt Days Listed: 270
-5.56% ($25,000) 1 Price Change : Last Change 2 Days Ago
Half Duplex - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 37ft.Concrete

Nestled at the end of a peaceful dead-end street, this well maintained 2-bedroom, 1-bath home offers both privacy and serene water views. The property backs onto a picturesque canal that is fully maintained by the HOA, ensuring a low-maintenance outdoor lifestyle.Outside, enjoy the tranquil canal from your backyard, ideal for morning coffee or evening sunsets. Located in a family-friendly community, this home offers easy access to Bogie Channel, local amenities, parks, and the loveable Key Deer. This is a rare opportunity to own a piece of paradise and quiet waterfront living.

$475,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
5 Bed, 5 Baths, 2,900 SqFt Days Listed: 52
Fractional Ow - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 55ft.Cut/Natural

New co-ownership opportunity: Own one-eighth of this professionally managed, turnkey home by Pacaso. Tucked within the coveted White Marlin Beach enclave, this canal-front retreat captures the essence of refined Florida Keys living. Framed by swaying palms and a gracious front entry, the 5-bedroom, 3.5-bathroom residence offers a seamless blend of comfort and coastal elegance.The open-concept main level is bathed in natural light, with soaring ceilings, oversized windows, and glass doors that connect the living area to the private pool and tranquil canal beyond. A bright, gourmet kitchen anchors the space with JennAir appliances, dual sinks, and generous cabinetry--ideal for effortless entertaining. A bay window in the dining area frames serene views of the pool.The main-floor primary suite features a custom walk-in closet and direct access to the patio and pool. Upstairs, a second spacious bedroom offers a large closet and a Jack-and-Jill bath shared with an adjoining guest room. Two additional bedrooms provide ample accommodations for family and guests. The home comes fully furnished and professionally decorated.

$489,000
Little Torch Key
Coral Shores Estates   - MM: 28.00
2 Bed, 2 Baths, 1,056 SqFt Days Listed: 21
Mobile Home - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Welcome to your dream retreat by the sea! This beautifully renovated 2/2 offers the perfect blend of classic coastal charm and modern upgrades. Recently renovated with a new roof (2021), new doors and windows (2000), new AC units and updated paint throughout. This home is located in a serene waterfront community with an unlimited free-access boat launch located only minutes from the house. Enjoy scenic views and sea breezes from the covered porch, dock or large landscaped yard. Enjoy the peaceful surroundings without the upkeep of boat traffic. Step inside to discover a light-filled open-concept living space complete with an open kitchen and living area that is perfect for entertaining. The spacious master bedroom offers a private ensuite bath. The second bedroom is perfect for guests or could be used as a home office. This home is move-in ready and ideal as a year-round residence , weekend getaway, or income-producing vacation rental. Dont miss your chance to own a slice of coastal paradise. Priced to sell!

$539,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,020 SqFt Days Listed: 231
-22.89% ($160,000) 5 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip

Nestled within the peaceful surroundings of the Key Deer Refuge, this charming 2 bedroom, 1 bathroom canal-front home offers a unique blend of nature, privacy, and easy access to water adventures. The homes inviting, light-filled interior embraces the essence of a classic Keys residence, with spacious, well-designed rooms. The open living area, filled with natural light from large windows, seamlessly connects to the kitchen, creating a warm, welcoming space perfect for both entertaining and quiet relaxation. Tropical light filters through every corner, framing serene canal and garden views that enhance the homes tranquil ambiance. Each bedroom offers ample space for rest and rejuvenation, while a bonus room provides flexible options as a cozy home office, additional storage, or hobby space. For those who love the water, this property is a true paradise. A private on-site boat ramp allows for convenient small-vessel access, while a larger neighborhood boat ramp around the corner provides even more options for boaters. Just minutes from open water, the home is ideally situated for enjoying the Keys renowned fishing, snorkeling, and diving. The neighborhood is equally appealing, combining a quiet setting with access to all essential conveniences. Nearby, youll find local shopping, popular restaurants, and vibrant bars, plus the Big Pine Community Park for outdoor recreation. The Key Deer Refuge across the street creates a natural buffer, adding privacy, preserving the local beauty, and offering occasional sightings of the charming Key Deer.This home perfectly balances a tranquil, island lifestyle with modern comforts, making it an ideal place for anyone seeking the best of Florida Keys living.

$599,999
Big Pine Key
Doctors Arm   - MM: 30.50
3 Bed, 3 Baths, 1,080 SqFt Days Listed: 75
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Other Dockage

Updated adorable 3 bedroom, 1 bath canal-front home situated in the desirable Doctors Arm neighborhood of Big Pine Key. Enjoy direct, bridge-free access to open water. The property includes approval for a boat lift by the Dept of the Army Corp of Engineers, which can be transferred to the new owner.This home has been tastefully updated, featuring stainless steel appliances, newer electric service, an on-demand hot water heater, impact-resistant windows and doors, and a durable metal roof. The interior is bright and welcoming. Just inside the front door is a nice sized area that would be a perfect TV room along with one bedroom. Just up a few steps to the upper level is more living space with room for a dining table. Just down the hall are two bedrooms and a full updated bathroom.The spacious backyard boasts a spacious deck with an outdoor shower, offering ample space for a pool and plenty of room to relax or entertain.

$699,000
Marathon
J. G. Estates   - MM: 59.50
2 Bed, 2 Baths, 1,496 SqFt Days Listed: 17
Mobile Home - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 60ft.

Looking for a no-frills Florida Keys escape with unbeatable dockage? Welcome to your ultimate fish camp in Grassy Key! This standalone home with no HOA offers instant bay access and quick ocean access from a 60-foot deep-water dock. A large exterior storage building is perfect for all your gear. Inside, the home is spacious and has been updated with new electrical, a new water heater, brand-new doors and windows, and a newer metal roof (2020). Tucked away in the quieter part of Marathon yet easily accessible off US-1, its the ideal weekend retreat for boaters and anglers.

$699,000
Big Pine Key
Port Pine Heights   - MM: 29.00
2 Bed, 2 Baths, 912 SqFt Days Listed: 17
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Enjoy canal-front living in peaceful Port Pine Heights, where youre sure to see the diminutive key deer roaming daily. This 2BD/2BA home on a 7,963 sq. ft. corner lot is just two canals away from open water leading to calm, backcountry waters and the Content Keys, as well as the Atlantic for offshore activities. The interior is light and bright with a slight cathedral ceiling; the kitchen and bathrooms are updated, new impact-resistant windows and doors have been installed, and the staircase and entry porch were recently replaced. The large, covered porch is a wonderful spot for relaxing and marveling at the evening sky. The wood dock needs attention, which is reflected in the list price. Located on the open water and offering ever-changing sunsets is the Port Pine Heights Park on Joyce Rd. for owners and residents, a short walk away. Whether youre looking for a 2nd home or planning to become a Keys local, this is an excellent opportunity to purchase a canal-front home under $700,000.

$699,000
Summerland Key
S Summerland Key Yac   - MM: 25.00
3 Bed, 3 Baths, 1,144 SqFt Days Listed: 12
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 60ft.Concrete

So many opportunities at this 3 Bedroom 2 Bath canal front home located in the Special Fishing District on Summerland Key where home businesses including commercial fishing and boat mechanics are allowed. Boasting 60 of road frontage with excellent highway visibility and 60 of concrete canal dockage with quick and easy access to the gulf and ocean. The newly remodeled coastal style home offers impact windows, metal roof, vinyl plank flooring, open kitchen with white shaker cabinetry and quartz counters, new baths and a split floor plan. Need more space? 3 Adjacent canal front lots each with 60 of concrete dockage are also for sale for $350,000 a piece.

$699,000
Big Pine Key
Doctors Arm   - MM: 30.50
2 Bed, 2 Baths, 672 SqFt Days Listed: 51
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Updated cottage with all the necessities you need with minimal maintenance. This CBS home has a newer metal roof, mini split A/c, updated kitchen on 3 lots only a very short ride to Boggie Channel, the only market channel to the Atlantic and Gulf. This is a great opportunity for boaters and naturalist as this is only a short walk or kayak to No Name Key and surrounding waters and nature trails. Large 280 square foot utility building with workshop. A short walk to the No Name Pub, a Keys historic watering hole. Dont miss your opportunity for this 15000 square foot, 3 lot parcel with a lovely concrete home.

$699,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,039 SqFt Days Listed: 152
-10.72% ($83,900) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Fixed BridgeCut/Natu

SITUATED ON A 50 FT. WIDE CANAL, this updated 3 bedroom / 2 bath home offers very good boat access to Pine Channel, the Atlantic and back country. The great room is bright and airy with a cathedral ceiling, south facing picture window and French doors that lead to the covered porch overlooking the canal. Updates include impact-resistant windows and doors, new stainless steel kitchen appliances, recent vinyl plank flooring and vanities; 2018 metal roof; the water heater is less than a year old. The 5,000 sq. ft. lot offers 50 ft. of canal-frontage and the nearby public boat ramp couldnt be more convenient! Eden Pines Colony is a friendly neighborhood where the Key deer roam and bike paths, shopping, parks, banks and more are within easy reach on the island.

$715,000
Key Largo
Calusa Campground   - MM: 101.50
2 Bed, 2 Baths, 500 SqFt Days Listed: 49
Mobile Home - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift35ft.

Stunning canal front Calusa property includes a 2022 Elevation RV with less than 2 years of use. Easy bay access.15K boat lift. Master bedroom with a king-size bed and a full-size bathroom with shower, split loft. 3 a/cs, ceiling fans, large kitchen with plenty of cabinets, electric full size stove w/ oven and refrigerator. Fully furnished and ready for you to move in. The lot has a covered outdoor terrace. It includes the 10 x 8 aluminum storage shed. Use it as a weekend get-a-way or rental income. Calusa is one of the few communities in the Florida Keys that allow short term rentals. Just an hours drive south from Miami and you are in paradise. Calusa has many amenities like a marina/boat ramp, temporary dockage, boat storage, 24-hour security, tennis and basketball court, playground, laundry rooms, pool and recreational hall. Additionally, the property is located close to several restaurants, shopping, entertainment, and health care. Come see it and you will love it!

$719,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,353 SqFt Days Listed: 209
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 50ft.Concrete

This 3BR spacious canal front home with quick open water access is nestled at the end of a quiet dead-end street. Amidst lush vegetation, this property offers the ultimate sanctuary for those seeking privacy and a connection to the Keys lifestyle. 50ft concrete seawall with 10,000lb boat lift. This home boasts an inviting shaded deck creating the perfect outdoor space for relaxation and entertainment. The homes interior layout boasts almost 1400sqft, including 3 spacious bedrooms, 2 bathrooms, and a bonus room that could be used as an office, workout area, or Florida room. 30AMP hook up.

$725,000
Big Pine Key
Tropical Bay   - MM: 30.50
2 Bed, 2 Baths, 1,008 SqFt Days Listed: 401
-12.12% ($100,000) 4 Price Changes : Last Change 27 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits188ft.

Welcome to our cozy retreat nestled on Big Pine Key. This charming two bedroom one bath cottage offers a tranquil escape on a DOUBLE LOT fenced, providing privacy and security. Enjoy the picturesque waterfront views from your own back yard. Florida room with large impact windows to capture the water views. Impact windows through out. Approximately 273 feet of concrete seawall with davits, Small garage for extra storage. Property is also 100 % handicap accessible. This home is your gateway to laidback island living. Make offer!!

$735,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,056 SqFt Days Listed: 255
-8.01% ($64,000) 2 Price Changes : Last Change 95 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Freshly remodeled waterfront home! Located in a lovely neighborhood with a boat ramp right around the corner! Exterior of property has open parking as well as covered parking for multiple vehicles. Below home is surrounded by lattice to give additional shade and privacy. So much potential downstairs for outdoor entertainment.The main living area has gone through a full renovation. Kitchen boast sleek quartz countertops and newly installed cabinets and backsplash. Both bathrooms have been upgraded. Gorgeous high end tiling in shower and floor, accompanied by new vanities. Throughout the house is luxury plank vinyl flooring and crown molding to make this home shine even more. Off main living area is an expansive back deck for relaxation. Local grocery store, dog park, and food/beverage only minutes away! Like what you see? Call today!

$769,000
Ramrod Key
Ramrod Shores   - MM: 27.00
3 Bed, 3 Baths, 1,488 SqFt Days Listed: 45
-2.53% ($20,000) 2 Price Changes : Last Change 1 Day Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Welcome to your slice of paradise in Ramrod Key! This newer built (2018) beautifully maintained single-family home offers 1,488 square feet of comfortable living space, perfectly situated on a spacious 6,000 square foot lot. Featuring 3 bedrooms and 2 bathrooms, this property is ideal for full-time residents, vacationers, or investors seeking a rental opportunity in the Florida Keys.Enjoy the tropical lifestyle with ample outdoor space, including designated RV and boat storage--perfect for all your island adventures. Whether youre relaxing on the porch, heading out on the water, or entertaining guests, this home is designed for easy, breezy coastal living.Dont miss your chance to own a piece of the Keys. Schedule your private showing today!

$772,500
Ramrod Key
Ramrod Shores   - MM: 27.00
3 Bed, 3 Baths, 1,440 SqFt Days Listed: 97
-7.21% ($60,000) 3 Price Changes : Last Change 19 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 16ft.Cut/Natural

Experience the tranquility of the Florida Keys in this meticulously maintained home, completed in 2019 and ready for your immediate enjoyment. This stunning property showcases thoughtful upgrades totaling over $50,000 by the current owner, designed to elevate your comfort and convenience. The interior offers a seamless blend of modern living and coastal charm, while the impressive NEW 299 sq. ft. storage area--equipped with impact-rated windows and a slider--presents breathtaking views of the swimming canal. This versatile space is perfect for all your storage needs or as a workshop-its a must see! Situated just a short distance from the vibrant locales of Marathon and Key West, youll enjoy the best of both worlds. Outdoor enthusiasts will appreciate the added 30-amp RV hookup and yard space for a 30-foot boat, with a public boat ramp located just a few miles away. Dont miss the opportunity to make this move-in ready gem your new home!

$775,000
Big Pine Key
Ross Haven   - MM: 31.00
2 Bed, 2 Baths, 912 SqFt Days Listed: 83
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: DavitsConcrete

Welcome to your slice of paradise in the beautiful Florida Keys! This 2-bedroom, 2-bathroom canal-front home is perfectly situated in Big Pine Key, offering direct access to the renowned Bogie Channel and some of the best boating in the area. Enjoy nice views of the open water.Enjoy 50 feet of concrete seawall, complete with boat davits, making it easy to launch and dock your vessel. The screened porch provides the perfect spot to relax and take in the partial open water views, while gentle sea breezes flow through. A cargo lift makes transporting supplies effortless, and additional storage ensures plenty of room for all your gear.Surrounded by the natural beauty of Key Deer Refuge and just minutes from Bahia Honda State Park, this home offers a serene yet adventure-filled lifestyle. Whether youre fishing, diving, or simply soaking up the laid-back Keys atmosphere, this is the ideal waterfront retreat.Dont miss this rare opportunity--schedule your private showing today!

$775,000
Little Torch Key
Mates Beach   - MM: 28.50
2 Bed, 2 Baths, 848 SqFt Days Listed: 23
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

640 Carolyn Avenue is a modern coastal retreat designed for comfort, privacy, and effortless outdoor living. Built-in 2021, this 4-year-old Affinity modular home blends high-quality construction with thoughtful design for the carefree lifestyle that defines island living.Set on an oversized canal-front lot with a 320 sq ft composite dock and fish cleaning station, this 2BD/2BA home invites you to enjoy the best of the Florida Keys with ease and peace of mind.Step inside to a light-filled interior featuring vinyl plank flooring, modern lighting, and an open-concept layout ideal for relaxed living or entertaining. The kitchen showcases granite countertops, a distressed wooden bar counter, and a Whirlpool stainless steel appliance suite. Impact-rated windows and doors enhance natural light while providing superior hurricane protection.The private primary suite includes a large walk-in closet with built-ins and a spa-like bath with a glass-enclosed shower and ample storage. The second bedroom is ideal for guests or a home office and is served by a stylish second bath with a tub-shower combo.Step out onto the composite deck overlooking the canal, surrounded by native landscaping and mature trees--perfect for morning coffee or sunset cocktails.With Hardie board siding, a metal roof, elevated construction, and a dedicated laundry room, this home is designed for durability and ease. Ample off-street parking and low-maintenance finishes complete the package.Whether youre launching a boat or unwinding under the stars, this turnkey property offers the best of Florida Keys living.

$799,000
Big Pine Key
Port Pine Heights   - MM: 29.00
2 Bed, 2 Baths, 1,008 SqFt Days Listed: 4
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Canal-Front Paradise in the Heart of the National Key Deer RefugeBig Pine Key, FloridaWelcome to your serene island escape! Nestled in the heart of the National Key Deer Refuge, this beautifully renovated two-bedroom, two-bath stilt home offers the perfect blend of modern comfort and natural beauty.Property Highlights:Canal-Front Property with ample space for a dock -- ideal for boating enthusiasts and water lovers.Fully renovated with tasteful, high-end updates throughout.Fully tiled home, including the spacious outdoor patio -- perfect for seamless indoor/outdoor living in the Keys.Gourmet kitchen featuring high-end appliances and thoughtful, modern finishes.Cozy fireplace to complement your evening gatherings.Fully furnished, including all televisions -- simply bring your suitcase and start living the Keys lifestyle.Bonus storage shed underneath for all your tools, gear, and water toys.Surrounded by miles of nature trails, right outside your door -- a paradise for hikers, birdwatchers, and wildlife enthusiasts. The famous Key Deer are plentiful in this area.Whether youre looking for a full-time residence, a seasonal escape, or a lucrative rental property, this property offers it all in one of the most unique and tranquil settings in the Florida Keys.Dont miss the chance to own a piece of paradise where nature meets luxury.

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 06-14-2025.
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