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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 224
Order By:

$439,000
Big Pine Key
Sands Subdivision   - MM: 31.00
1 Bed, 1 Baths, 441 SqFt Days Listed: 35
-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: 101
-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.

$450,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,232 SqFt Days Listed: 23
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 195ft.Concrete

Fix and flip or buy/fix and hold. So much potential with this spacious 3 bedroom waterfront home. Offers about 195ft of dockage for your boat and sits on a large corner lot. Located in a lovely neighborhood with a boat ramp a couple minutes away. Dont miss this opportunity, call today!

$475,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
5 Bed, 5 Baths, 2,900 SqFt Days Listed: 66
-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.

$639,900
Big Pine Key
Doctors Arm   - MM: 30.50
3 Bed, 3 Baths, 1,080 SqFt Days Listed: 82
-4.49% ($30,100) 2 Price Changes : Last Change 24 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.

$650,000
Big Pine Key
Tropical Bay   - MM: 30.50
3 Bed, 3 Baths, 1,200 SqFt Days Listed: 12
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 AE9This 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

$675,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,020 SqFt Days Listed: 62
-3.43% ($24,000) 1 Price Change : 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.

$675,000
Big Pine Key
Doctors Arm   - MM: 30.50
2 Bed, 2 Baths, 1,080 SqFt Days Listed: 17
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat LiftConcrete

Stunning two bedroom two Full bath CBS Canal front home located in the coveted Drs Arm neighborhood. Home of the famous Key Deer. Located with deepwater access to both the Atlantic Ocean as well as the Bayside. This spacious home offers an open concept as well as a large kitchen featuring Stainless appliances and granite countertops. This house shows an oversized master bath, as well as a laundry room.

$679,000
Big Pine Key
Tropical Bay   - MM: 30.50
2 Bed, 2 Baths, 888 SqFt Days Listed: 316
-9.35% ($70,000) 3 Price Changes : Last Change 12 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits124ft.

*** MOTIVATED SELLER NEW METAL ROOF, NEW CENTRAL A/C ***Welcome to this waterfront paradise on Big Pine Key! Charming 2 bedroom, one-and-a half-bath, corner canal CBS home is a boaters dream, featuring two concrete docks, a generous 70 and an additional 54 complete with two davit sets for all your watercraft needs. A total of 270 of canal front, situated on a fenced 15,045 square foot lot. This fully furnished property offers the perfect blend of privacy and convenience. Kitchen credit offered. Close to shopping and dining yet a very private location. The nearby bridge has a clearance of 7 feet. Excellent boating to Bogie Channel. Lot can be subdivided. Owner financing considered with a large down payment. Big Pine Key where time truly moves slower.

$699,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 936 SqFt Days Listed: 41
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 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.

$699,000
Little Torch Key
Coral Shores Estates   - MM: 28.00
3 Bed, 3 Baths, 1,176 SqFt Days Listed: 159
-6.79% ($50,900) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

Little Torch Key Retreat with a spacious floor plan, on a serene plugged canal, just minutes to neighborhood boat ramp and excellent boating access! Upon entry, this 2022 home boasts loads of natural light and soaring ceilings. The well-equipped kitchen offers abundant, all-white cabinetry, stainless appliances, granite countertops and pantry, making entertaining a breeze. Impact sliding glass doors lead out to a screened-in balcony, overlooking the well-maintained back yard and crystal clear swimming canal. Boasting two large guest bedrooms, and an expansive primary suite with en suite bathroom and large closet, this slice of paradise comes complete with loads of space for a family or visitors. Additional features include a tankless water heater, large upstairs laundry closet, hardi board siding, and impact doors and windows throughout. Downstairs, enjoy fresh tropical fruit on this lushly landscaped lot, offering both banana and papaya trees! Composite decking provides an ideal waterside dining space for grilling up your fresh catch, or hosting memorable al fresco meals. Take advantage of year-round temperate weather via kayak or paddle board from the backyard swimming canal! Keep tools and equipment dry and secure in a sizable storage shed or custom fishing locker. Plenty of covered parking with a large covered carport, and additional open parking and trailer storage on this well-maintained lot. Located within a quiet, established neighborhood but just minutes to dining and convenience stores in town, this prime location has it all! The coveted Florida Keys lifestyle awaits!

$719,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,353 SqFt Days Listed: 40
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: 232
-9.09% ($75,000) 3 Price Changes : Last Change 43 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.

$760,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,039 SqFt Days Listed: 366
-4.88% ($39,000) 2 Price Changes : Last Change 21 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Price Reduction!!! Pleasant 3 bedroom waterfront home located in Eden Pines Colony. Such a lovely family neighborhood where you can experience the natural beauty and wildlife. This home truly shows well and has gone through recent upgrades such as new flooring, bathroom vanities, new kitchen appliances, and hot water heater. For storm protection and lower insurance rates, house is outfitted with impact windows/doors and has a metal roof (2018). Main living area and kitchen is open concept, which is great for entertainment/family gatherings. Off main the living area you have french doors that lead to your private deck where you can relax and enjoy the island breeze. Exterior of property offers dockage to accommodate a boat and the downstairs unit is a bonus space for workshop and storage. Within minutes away is a neighborhood boat ramp, dog park, grocery store, and restaurants. Do not miss your chance to get this delightful property, located in a relaxed yet festive neighborhood!

$775,000
Ramrod Key
Ramrod Shores   - MM: 27.00
3 Bed, 3 Baths, 1,242 SqFt Days Listed: 57
-1.90% ($15,000) 1 Price Change : Last Change 21 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Discover your peaceful retreat on this rare double lot with scenic water views. This comfortable 3BD/2BA home features expansive covered patios, carport, and generous legal storage. With a 200-amp service for additional RV hookup and abundant parking, theres ample space to expand, add a pool, or both. Canal is plugged (no boating) but great for kayaking and paddle-boarding. Plenty of space for boat trailers and quick access to the public boat ramp just across US1 at Looe Key Reef Resort. Enjoy living the laidback Keys-lifestyle while still being just 30 miles to downtown Key West. Truly the best of both worlds!

$799,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,056 SqFt Days Listed: 86
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!

$799,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 816 SqFt Days Listed: 22
-3.62% ($30,000) 1 Price Change : Last Change 7 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Fixed Brid

Experience Paradise Living in Eden PinesWelcome to your dream home, nestled in the serene Key Deer Preserve on Big Pine Key. This updated 2-bedroom, 2-bath home is perfectly situated in the sought-after Eden Pines neighborhood, offering a private and tranquil retreat surrounded by nature.Step inside to find a warm and inviting space featuring a mix of tile and laminate flooring, stainless steel appliances, and professionally tinted windows with a porch sunshade for added comfort. Modern upgrades include impact windows and doors, a durable metal roof (installed in 2018), and Hardie Board siding, all designed to keep insurance costs low. A weather station adds convenience, while recent termite tenting (August 2024) ensures peace of mind--buyers can assume the warranty in August 2025.The large screened-in porch, equipped with no-see-um screening, offers stunning views of the canal and a fully fenced backyard. The yard is pet-friendly and thoughtfully designed to keep Key Deer at bay, protecting your fruit trees, including Meyer lemon, Persian lime, and grapefruit varieties.Boating enthusiasts will love the 40 dock, complete with water, electric, a fish cleaning station, and room for a boat lift. With excellent boating access via Pine Channel and a 3 draft, its ideal for larger vessels, while the fixed bridge (11 clearance) makes navigating out to the backcountry a breeze.Additional features include 552 sq. ft. of legal storage, currently utilized as a workshop and assumable flood insurance at an attractive rate of $828/year.This home is easy to show, even on short notice--schedule your private tour today and discover the best of Big Pine Key living!

$819,900
Big Coppitt
Gulfrest Park #2   - MM: 10.00
2 Bed, 2 Baths, 1,200 SqFt Days Listed: 92
-3.53% ($30,000) 1 Price Change : Last Change 18 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 50ft.Concrete

Welcome to your dream waterfront home in the beautiful Florida Keys! Located just 15 minutes from Key West, this home offers both tranquility and convenience. This charming 2-bedroom, 2-bathroom residence offers direct access to the water, perfect for boating, fishing, and enjoying tropical sunsets. With an open-concept living area and modern kitchen with stainless steel appliances, this home is ideal for both relaxation and entertaining. This home has a durable metal roof that ensures peace of mind and the master bathroom is a luxurious retreat, featuring a jacuzzi tub, double vanities and ample space for relaxation. The spacious outdoor composite deck allows you to soak up the coastal breeze, while the private dock makes it easy to embrace the island lifestyle. Located close to shopping, dining, and local attractions, this Florida Keys gem is the perfect escape for year-round living or a vacation retreat.

$820,000
Big Torch Key
Torchwood West   - MM: 25.50
2 Bed, 2 Baths, 1,040 SqFt Days Listed: 522
-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.

$824,900
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 884 SqFt Days Listed: 15
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 a full bath upstairs and the downstairs has lots of storage, one full bath, and a half bath. All new plumbing, electrical, metal roof and impact doors and windows installed after 2017. Completely fenced. Easy to see. Buyer to verify

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 12-27-2024.
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