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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 253
Order By:

$439,000
Big Pine Key
Sands Subdivision   - MM: 31.00
1 Bed, 1 Baths, 441 SqFt Days Listed: 96
-12.02% ($60,000) 2 Price Changes : Last Change 1 Day 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.

$450,000
Big Pine Key
Tropical Bay   - MM: 30.50
2 Bed, 2 Baths, 654 SqFt Days Listed: 162
-14.29% ($75,000) 2 Price Changes : Last Change 27 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: 127
-4.81% ($24,000) 1 Price Change : Last Change 2 Days Ago
Fractional Ow - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 55ft.

New CO-OWNERSHIP opportunity: Own 1/8 of this professionally managed, turnkey home. Swaying palms and a gracious front entry leave no doubt that relaxation awaits in this new construction Florida Keys home. The 5-bedroom, 3.5-bathroom home is along a canal in sought-after White Marlin Beach. The open-concept main floor has soaring ceilings, oversized windows and glass doors connecting the living space to the pool and waterway beyond. The bright gourmet kitchen features JennAir appliances, two sinks and spacious cabinets. A bay window in the dining area serves up a pool view. The main floor primary bedroom includes a custom closet and opens to the pool and patio. The main bedroom upstairs has a large closet and a Jack & Jill bath leading to another guest bedroom. With two additional bedrooms, the home easily accommodates family and friends. The home comes fully furnished and professionally decorated. There will be six 1/8 shares and one 1/4 share sold.

$610,000
Big Pine Key
Tropical Bay   - MM: 30.50
3 Bed, 3 Baths, 1,200 SqFt Days Listed: 73
-6.15% ($40,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Fixed Bridge7

Large corner lot canal home opportunity in Big Pine Key.Discover the possibilities with this waterfront property at 30368 Killdeer Ln, Big Pine Key! This 3-bedroom, 2-bathroom home offers a fantastic opportunity to create your dream retreat in the heart of the Florida Keys.Situated on a canal with access to open water. The home features an open layout with plenty of potential to reimagine the space to suit your vision. While the property does require TLC, it provides endless opportunities for customization. elevation is AE9. There is an yearly HOA fee of $250.This property is ideal for vacation home seekers, or anyone looking to bring their vision to life in a prime location. Close to local amenities, dining, and nature trails, this home is your chance to create a true Keys gem.2021 New heat pump AC 3 ton system2012 New 5V crimp roof installed.2008 New windows and accordion shutters

$625,777
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,506 SqFt Days Listed: 21
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Fixed Bridge

Charming 2-Bedroom Cottage with Serene Privacy in Big Pine Key. County owned lots to the North, South, and West ensures privacy.Nestled in the heart of Big Pine Key, this 2-bedroom, 1.5-bathroom cottage offers the perfect combination of tranquility, privacy, and natural beauty. With no development allowed to the west, youll enjoy an extra layer of seclusion, allowing you to fully embrace the surrounding wildlife and peaceful atmosphere.A short walk from the renowned Blue Hole, one of the areas most sought-after natural attractions, this home is ideal for nature lovers and those seeking a relaxed lifestyle in the Florida Keys. Whether youre an avid boater or just love the water, this property boasts convenient access for boats with up to a 3ft draft and 9ft bridge clearance, giving you easy access to the vibrant waters of the Keys.Inside, youll find a cozy, cottage-like space full of potential. The home offers the opportunity to add your personal touch and TLC, transforming it into the perfect retreat. The peaceful surroundings, coupled with the warm, inviting vibe of the home, make this the ideal spot to relax and unwind.If youre seeking a slice of paradise where you can create your dream home, this is the perfect opportunity. Come and see for yourself why Big Pine Key is one of the best-kept secrets in the Keys!

$627,900
Big Pine Key
Doctors Arm   - MM: 30.50
3 Bed, 3 Baths, 1,080 SqFt Days Listed: 143
-6.28% ($42,100) 4 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Davit Pads50f

Updated CBS 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 CBS home has been tastefully updated, featuring stainless steel appliances, new 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.

$640,000
Key Largo
Key Largo Trailer Village   - MM: 101.50
2 Bed, 2 Baths, 864 SqFt Days Listed: 23
Mobile Home - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 20ft.Rip Rap

This updated waterfront home is nestled on a spacious corner lot with plenty of room for a 20-foot boat! Recent improvements include fresh paint, a new central AC unit, laminate flooring, artificial grass, a brand-new 6x12 storage shed, and renovated bathrooms. The outdoor space is truly exceptional, featuring a sundeck and a screened-in porch, both ideal for enjoying the beautiful surroundings. The jacuzzi has been perfectly placed to provide stunning canal views as you unwind in the evenings. The fully fenced yard offers ample parking for all your water toys! The highly desirable Key Largo Village neighborhood boasts a private beach and two boat ramps right on Florida Bay--one so close, you could practically throw a rock to it! Conveniently located in the heart of Key Largo, its just a short ride to local restaurants and grocery stores.

$649,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 936 SqFt Days Listed: 102
-7.15% ($50,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip

CBS home on two lots with a county owned lot to the west which means there is a vacant lot on each side of the home. Located on a 50-foot-wide canal with a cut in boat slip. Only a short ride out to open water. Quiet street with lots of privacy, new roof in 2023, fenced yard. Close to shopping, Bahia Honda state park and beach and a short ride to Key West. Neighborhood boat ramp, lots of wildlife as this home is in the National Key Deer Refuge and boarders on the Great White Heron Refuge.

$665,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,020 SqFt Days Listed: 123
-4.86% ($34,000) 2 Price Changes : Last Change 20 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.

$675,000
Summerland Key
Snug Harbor Subdivision   - MM: 25.00
1 Bed, 1 Baths, 1,024 SqFt Days Listed: 28
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp38ft.Concre

Back-up Offers Welcome ~ ITS ALL ABOUT THE LOCATION! Cash offers only for this old-Keys, fish camp bungalow that was built in 1958 and needs repair or replacement. Just imagine the wonderful fish stories this home could tell! Heres your opportunity to enjoy amazing open water views and deepwater boating in the Lower Keys. Niles Channel provides excellent access to the ocean and back country - one can even see the Niles Channel Bridge from the location which is within walking distance of Tonios Seafood Shack & Tiki Bar. The fenced, 46 x 74 property has a concrete seawall and concrete boat ramp. One bedroom, a full bath and bonus living area are on the ground level; an open living room / kitchen and half bath are in the upper level; An interior spiral staircase connects the two levels, and an exterior staircase leads to the upper level. 512 sq. ft. concrete block ground level is LLF on property record card; 512 sq. ft. frame upstairs is FLA on property record card; metal roof; impact resistant windows upper level; no shutters; no range/oven. Although it has been loved through the years, the house needs lots of TLC. Theres a separate shed for storing fishing and dive gear. Hooked up the municipal sewer. Cash offers only. Just imagine what the future holds! ***DO NOT WALK PROPERTY without listing agent. ***

$719,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,353 SqFt Days Listed: 101
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.

$750,000
Big Pine Key
Tropical Bay   - MM: 30.50
2 Bed, 2 Baths, 1,008 SqFt Days Listed: 293
-9.09% ($75,000) 3 Price Changes : Last Change 99 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits188ft.

Welcome to our cozy retreat nestled on Big Pine Key. This charming one bedroom one bath cottage offers a tranquil escape on a DOUBLE LOT fenced in yard, 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. Easy, to make the house a 2 bedroom home. 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.

$770,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,056 SqFt Days Listed: 147
-3.63% ($29,000) 1 Price Change : Last Change 34 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!

$782,900
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,039 SqFt Days Listed: 44
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.

$789,000
Big Coppitt
Gulfrest Park #2   - MM: 10.00
2 Bed, 2 Baths, 1,166 SqFt Days Listed: 92
-4.36% ($36,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 150ft.

Discover your ideal Keys retreat in this delightful 2 bedroom, 2 bathroom home, perfectly situated just a short 15-minute drive from Key West. Step inside to experience an inviting open floor plan accentuated by vaulted ceilings and a generously sized kitchen, ideal for both relaxing and entertaining.The master bedroom offers a private ensuite bathroom and opens onto a covered porch overlooking the serene canal. Outside, a fenced yard ensures privacy, making it a haven for pets and peace of mind.Enhancing this propertys allure are its coveted amenities: a covered back porch for al fresco dining, a sturdy concrete dock for your boat, a convenient workshop space, and seamless boating access to both the Gulf and Atlantic waters. Whether youre seeking a tranquil escape or an active waterfront lifestyle, this home embodies the essence of Keys living. Dont miss the opportunity to make it yours - schedule your showing today and let the beauty of the Keys captivate you.

$794,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 884 SqFt Days Listed: 76
-3.75% ($30,900) 2 Price Changes : Last Change 8 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: BasinConcrete

Beautifully remodeled, canal front home with cut in boat basin! Located in family friendly, quiet neighborhood, with a view straight down the canal, tropical landscaping, open living/kitchen, 2 bedrooms and one and the downstairs has lots of storage. All new plumbing, electrical, metal roof and impact doors and windows installed after 2017. Completely fenced. Easy to see. Buyer to verify

$795,000
Big Pine Key
Hollerich Subdivision   - MM: 31.00
2 Bed, 2 Baths, 960 SqFt Days Listed: 13
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Concrete

Paradise in Big Pine Key!Bring your boat and embrace the Florida Keys lifestyle in this beautiful canal-front home, complete with a concrete dock and easy access to open water. This turnkey 2-bedroom, 2-bathroom home has been thoughtfully updated with a custom kitchen featuring granite countertops, upgraded dark stainless steel appliances, a built-in oven, and a spacious kitchen island.Enjoy ceramic tile flooring throughout, impact-resistant windows, and a newer roof (2018). The bathrooms boast tiled showers with a rainhead, and modern comforts include a Nest thermostat, Hardie board siding, and a tankless water heater.Downstairs, a large permitted storage space is perfect for a man cave or she-shed. Located just one street away from Big Pine Park, this home offers both relaxation and adventure.Dont miss out on this gem--schedule your showing today!

$799,000
Big Pine Key
Port Pine Heights   - MM: 29.00
2 Bed, 2 Baths, 1,176 SqFt Days Listed: 3
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Ramp50ft

*** Open House, Saturday, 3/1/2025, 11 AM to 2 PM *** Bring your boat and your ideas-this canal-front home is primed for its next chapter, with the space, features, and water access to make it your own. Situated in a large, fenced corner lot within the National Key Deer Refuge, this home offers space for extra vehicles, or even a future pool. A private boat ramp and a concrete dock with davits make it easy to launch into the Backcountry or Atlantic for a day on the water. Inside, the open floorplan is complemented by crown molding and newer stainless-steel appliances. Impact windows, a metal roof, and Hardie Board siding add peace of mind, while a screened porch provides a shaded spot to enjoy peaceful canal views. With no direct neighbors and plenty of green space, the setting feels private yet open.This property offers both immediate enjoyment and future potential. Dont miss the chance to make it your own--schedule a showing today.

$815,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,048 SqFt Days Listed: 37
-1.21% ($10,000) 1 Price Change : Last Change 17 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat SlipC

This home is in a great location, the desirable Eden Pines neighborhood on Big Pine Key. The main living area has two bedrooms and two baths with a large living room and open kitchen area. There is an added additional room that can be used for an office or guest space. The home is perfect for the avid fisherman or water enthusiast with A 14K lb. boat lift and ample concrete dockage. Easy canal access to Pine Channel and then open water!

$820,000
Big Torch Key
Torchwood West   - MM: 25.50
2 Bed, 2 Baths, 1,040 SqFt Days Listed: 583
-3.53% ($30,000) 2 Price Changes : Last Change 11 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 42ft.

Excellent Investment Opportunity! Classic waterfront home in quiet Big Torch Key. This home features 2 bedrooms, two bathrooms and a spacious open living/dining/kitchen area. Water from a 12k gallon cistern with a reverse osmosis system. City water is available and the home is connected to sewer. This home is being sold as a life estate. The homeowner will remain in place after purchase of the home. Details will be negotiated with the right buyer. Great boating from the 50 foot wide canal with little traffic. Come enjoy the peacefulness and privacy you are looking for in the Keys.

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 02-26-2025.
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