Divider
Content Divider

Florida Keys Waterfront Homes on the Bay / Gulf Side of the Island For Sale

Total Listings 274
Order By:

$1,199,000
Little Torch Key
Mates Beach   - MM: 28.50
3 Bed, 3 Baths, 1,440 SqFt Days Listed: 30
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 20ft.

Experience the Ultimate Florida Keys Lifestyle in This One-of-a-Kind Coastal Retreat!Step into coastal elegance with this stunning 3-bedroom, 2-bathroom home offering 1,440 square feet of thoughtfully designed living space. The expansive great room showcases soaring 20-foot ceilings--a rare gem in the Keys--creating an airy, open feel.Stylish wide-plank luxury vinyl flooring runs throughout the home, complementing a modern kitchen featuring sleek quartz countertops and a spacious prep island, ideal for entertaining. Enjoy everyday convenience with a Samsung all-in-one washer/dryer combo.Stay comfortable and energy-efficient with four ductless A/C units and a tankless water heater. Outside, your backyard deep water canal offers a 3-foot control depth--perfect for swimming and boating right from your private dock. Durable Trex composite decking on the back deck and dock ensures low-maintenance living year-round.Wake up to breathtaking sunrises from the primary bedrooms private balcony. Owner is a licensed realtor.

$1,199,000
Big Pine Key
Big Pine Cove   - MM: 31.50
4 Bed, 4 Baths, 1,896 SqFt Days Listed: 42
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Welcome to your Florida Keys fortress! This newly constructed 4-bedroom, 3-bath concrete home offers unmatched durability, modern finishes, and gorgeous open water views from porches on both levels. Just a few hundred feet from deep water boating, this property provides the closest boat access to the world-famous Bahia Honda Bridge of any neighborhood in the Lower Keys, navigating to the ocean or backcountry is a breeze! Inside feels bright yet sleek with tile flooring throughout, hurricane impact windows and doors, all stainless steel appliances, and beautiful quartz countertops. The home is built for both functionality and peace of mind.Enjoy a concrete dock, boat lift, and water access that makes this a true boaters paradise. Located within walking distance to Big Pine Key Park and minutes to groceries and essentials, this location blends convenience with adventure.

$1,199,999
Key Largo
Calusa Campground   - MM: 101.50
2 Bed, 2 Baths, 350 SqFt Days Listed: 135
Mobile Home - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift80ft.Concre

Bay views and a rare double lot! This 3,165 sq. ft. corner RV lot is buildable and offers ample space to park your boat, jet skis, cars, trailer, and more. Included in the sale is a 2005 North Point Jayco Fifth Wheel.Enjoy stunning Bay views and breathtaking sunsets from your 80 ft. concrete dock with a boat lift. The community features resort-style amenities, including a pool, tennis and basketball courts, playground, community boat ramp and dock, two laundry facilities, and bathhouses with showers. Plus, theres a scenic bayside area perfect for sunset watching. Dont miss this incredible opportunity to own a slice of paradise in Key Largo!

$1,225,000
Big Pine Key
Misc Big Pine Key   - MM: 33.00
3 Bed, 3 Baths, 1,654 SqFt Days Listed: 74
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift25ft.

Escape to quintessential No Name Key to find this waterfront sanctuary. No Name Key is a secluded paradise; free of commercial development with fewer than 50 homes nestled in a one-of-a-kind conservation setting. This location offers unmatched stargazing and serene surroundings--yet its just over 10 minutes from the amenities of Big Pine Key, 45 minutes from Marathon and 1 hour from Key West. Reminisce on the Old Florida Keys while driving down the private road to Bimini Lane--a tranquil street with just 6 homes, surrounded by County-owned land. This hidden gem offers privacy, peace, and a true sense of community. Situated on a 13,980 square foot double lot with 120 feet of waterfront, this property boasts deep water, immediate Gulf access, recently upgraded 25-foot dock with low-maintenance decking, 15,000 lb boat lift, and 8 x 10 foot floating dock--perfect for boating enthusiasts and nature lovers alike. Originally built in 1995 by a concrete contractor as his personal Keys escape, this three bedroom, two bathroom wood frame home features poured concrete columns and balcony, metal roof, and storm-conscious design. Inside, youll find nearly 1,700 square feet of living space plus generous screened and open-air porches ideal for catching island breezes. Recent upgrades include updated AC, and connection to the Countys electric, water and sewer systems, complementing the nearly 15,000-gallon cistern, solar panels, and propane for off-grid resilience. The main level welcomes you with an open-concept living, dining, and kitchen area, along with two bedrooms and a full bath. Upstairs, the primary suite offers a renovated bathroom, updated flooring, and a private balcony with picturesque views of the Gulf. Ample carport parking for 4 vehicles with expansive room to add a pool and tiki hut to complete your tropical oasis. Whether youre seeking a peaceful full-time residence or a secluded second home, this No Name Key retreat is your gateway to authentic Keys living.

$1,245,000
Big Pine Key
Whispering Pines   - MM: 30.50
4 Bed, 4 Baths, 2,176 SqFt Days Listed: 316
-10.75% ($150,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davit Pads,Boat Lift

Nestled in the heart of Big Pine Key, this fantastic property offers 4 bedrooms, 2 baths, and 2,176 sq ft of living space. The living room boasts a charming open beam ceiling and a split floor plan. The fourth bedroom is a delightful bunk room. The kitchen, updated in 2017, features white cabinets, granite countertops, and stainless-steel appliances. The home is adorned with tile floors, impact windows, and a new metal roof installed in 2018.Situated on a half-acre, fenced yard with lush grass, this property includes a large saline chlorinated pool, two tikis, and a 75-foot seawall dockage and boat lift perfect for multiple boats. Easy access to the ocean or the gulf is available via Bogie Channel. Additional amenities include a dockside fish cleaning station, an outdoor shower with hot and cold water, and wiring for a portable generator. A 10x20 detached workshop/shed with power provides extra storage or workspace. This property also could be used as a monthly vacation rental.

$1,250,000
Marathon
Venice   - MM: 52.00
2 Bed, 2 Baths, 1,200 SqFt Days Listed: 100
-3.77% ($49,000) 1 Price Change : Last Change 51 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Welcome to your dream waterfront retreat! This newly renovated 2 bedroom, 2 bathroom CBS home is perfectly positioned in the heart of Marathon, offering a seamless blend of coastal modern design and island charm. Nestled in a peaceful neighborhood across from a tranquil nature preserve, this home is the perfect escape for those seeking serenity with easy access to all the Florida Keys have to offer. Step inside and be captivated by the open-concept great room, where a wall of impact glass floods the space with natural light while framing stunning canal views. The beautifully designed kitchen is a chefs delight, featuring sleek stainless steel appliances, quartz countertops, and ample prep space, perfect for preparing your fresh catch of the day. The spacious guest bedroom ensures comfort for visitors, while the primary suite offers a private oasis, complete with a luxurious ensuite bath featuring a dual vanity and custom tile shower.Outside, the possibilities are endless! The expansive yard has ample space for a pool or tiki hut, while 900 sq ft permitted lower enclosure provides endless opportunity and plenty of additional space and storage. Boaters will love the full-length concrete dock with deep-draft access, offering quick navigation to both the Atlantic and the Gulf. Conveniently located just minutes from Marathons best beaches, state parks, waterfront restaurants, and bars, as well as The Marathon Airport and the Millionaire FBO.

$1,250,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,376 SqFt Days Listed: 83
-3.47% ($45,000) 1 Price Change : Last Change 37 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Enter the Islamorada waterfront game with this fantastic ground level 3-bedroom home, perfectly situated between Tavernier & Snake Creek with direct bay access. Equipped with a brand new metal roof and built above flood to help with insurance costs. Canal side has 50 feet of frontage with a 30-foot concrete dock in good condition and a permit in place to extend the last 20 feet. Perfect Keys weekend retreat or for those looking to make the jump up to waterfront living. Room for a pool. Close to schools and the neighborhood boat ramp. Lock it up just in time for summer!

$1,275,000
Key Largo
Lake Surprise Properties   - MM: 106.00
3 Bed, 3 Baths, 1,248 SqFt Days Listed: 397
-3.77% ($50,000) 1 Price Change : Last Change 126 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Lift60ft

Location, location, location... ideally situated in North Key Largo for boating, fishing, diving, dining, shopping & more. Convenient for commuting. Whether you are seeking a primary residence, vacation getaway, or an investment property, dont miss your opportunity to own this piece of paradise. Lovely 3/2 waterfront pool home located in desirable Lake Surprise Estates. Elevated by concrete columns w/ a spacious ground floor storage room. 60 concrete dock w/ lifts & an addl concrete pad. Easy access to the bay & ocean. Spacious floorplan, vaulted ceilings & tile throughout. Kitchen w/ granite countertops, stainless appliances & an expansive island. Completely fenced, electric gate & lots of room for all your water toys. Simple to maintain salt-water pool, accordion shutters up-stairs & newer metal roof. Large, covered wrap-around patio & 2nd floor porch, perfect for gorgeous sunset views. Plenty of space to enjoy w/ your loved ones.

$1,275,000
Key Largo
Cross Key Waterways   - MM: 103.00
3 Bed, 3 Baths, 1,296 SqFt Days Listed: 140
-1.92% ($25,000) 1 Price Change : Last Change 58 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift40ft.Concre

Stunning Stilted 3-Bedroom Home with Bay Access & ElevatorDiscover this beautiful stilted 3-bedroom, 2-bathroom home, perfectly designed for comfort and convenience. Featuring spacious bedrooms with incredible closet space, this home also boasts a large storage room on the ground floor and an elevator for easy access.Located just two canals from the open bay, youll enjoy quick ocean access via Adams Cut--ideal for boating and water enthusiasts. The property offers a fantastic entertaining area, covered parking, and ample space to store your toys and trailer. 40 of seawall with a 20,000LB boat lift in the process of being installed.Dont miss this opportunity to own a waterfront gem in a prime location!

$1,295,000
Summerland Key
S Summerland Key Yac   - MM: 25.00
1 Bed, 1 Baths, 1,965 SqFt Days Listed: 82
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat RampOther

Seize this rare opportunity to own a prime working waterfront property with exceptional Highway visibility. This unique offering includes two waterfront buildings located at 24931 & 24933 Overseas Highway in Summerland Key, each with separate water, electric, and sewer connections for added flexibility. Situated on a 10,673 SF lot, the property features a 813 SF building, a 1,152 SF building, and a 192 SF utility/storage building for additional space. Additionally, the property includes a private boat ramp, providing convenient water access. Whether youre looking to expand or open a business or invest in a high-exposure location located on the water, this property offers incredible potential. Buyer to verify property rights.

$1,299,000
Big Pine Key
Whispering Pines   - MM: 30.50
3 Bed, 3 Baths, 1,043 SqFt Days Listed: 57
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

This newly remodeled 2-bedroom, 1-bathroom home is perfectly positioned on two spacious lots in the heart of Big Pine Key, offering over 20,000 sq ft of land and an incredible 297 feet of waterfront. With 75 feet of concrete dockage and quick access to the ocean via Spanish Harbor Channel, this is a boaters dream come true.Inside, enjoy peace of mind with impact-rated windows and doors, a sturdy metal roof, and stylish modern finishes throughout. Outside, theres plenty of room to expand, entertain, or simply relax and soak in the serene Keys lifestyle.Located just minutes from shopping, dining, and Big Pine Community Park, this home combines privacy and convenience in one of the Lower Keys most desirable neighborhoods.

$1,299,000
Big Pine Key
Kyle Dyre   - MM: 28.00
3 Bed, 3 Baths, 1,440 SqFt Days Listed: 99
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Concrete

Enjoy your morning coffee taking in views of the Bay, and watching the boat traffic go by on your large covered deck. In the evening, enjoy a cocktail while watching the sunset. There is approximately 210 feet of concrete seawall to park your boats and water toys. This meticulously maintained home has a metal roof, impact doors and windows, newer A/C, and many updates. Low flood insurance premium. Sellers prefer afternoon showing appointments. No pets allowed in the house on showings.

$1,299,000
Marathon
Woodburns Subdivision   - MM: 49.50
1 Bed, 1 Baths, 784 SqFt Days Listed: 116
-18.76% ($300,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Waterfront Retreat with Expansive Garage, Workshop & Open Water ViewsNestled in a private, tropical setting, this stilted concrete home offers breathtaking open water views, stunning sunsets, and ultimate seclusion.Car enthusiasts and hobbyists will love the massive 3-bay garage, built in 2015, featuring 1,211 sq ft, two hydraulic car lifts, a loft, and a commercial-grade stainless steel workshop sink. This fully insulated man cave/workshop is ideal for anyone in need of a high-functioning at-home workspace or serious storage. Spray foam insulation and an on-demand hot water heater complete the setup.Room for a dock - buyer to verify. The waterfront setting offers the potential to add a dock, making it even more ideal for boating enthusiasts. Buyer to confirm and manage permitting. Fully fenced and gated for privacy, with a bonus lower-level space for guest overflow or flexible use. A rare blend of functionality and Florida Keys charm.

$1,299,999
Key Largo
Lake Surprise Properties   - MM: 106.00
2 Bed, 2 Baths, 960 SqFt Days Listed: 4
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Lift

Bring Your Boat and Start enjoying Keysliving at this Beautiful Bayside Home in Key Largo! 60 foot Concrete Dock with 10,000 lb Lift, completely Fenced in with Top of the Line Synthetic Grass and a Wonderful Tiki Hut for Outdoor Entertaining! Just Move in and bring your Clothes as this Home is fully furnished and Equipped to Enjoy right away or take over Monthly Rental Reservations. Less than an hour drive from Miami and Near all the best Restaurants and nearby Activities the Keys has to offer both on Land and by Water!

$1,300,000
Key Largo
Cross Key Waterways   - MM: 103.00
4 Bed, 4 Baths, 2,568 SqFt Days Listed: 108
-6.81% ($95,000) 1 Price Change : Last Change 83 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits

MULTI GENERATION OPPORTUNITY! Water view from every floor! Prime waterfront location for fishing, diving, and boating enthusiasts. Featuring a concrete block home with incredible potential, it provides immediate access to both ocean and bay-side adventures via a concrete dock. Whether youre finishing your day with a sunset on the water or hosting friends, the Sound views from nearly every corner of the property create a stunning backdrop for any occasion. Unbeatable waterfront access, perfect for ocean and bay-side boating. Expansive two-story layout with 2,304 sqft of living space (1,152 sqft per floor). 3 Bedrooms, 2 Bathrooms--ideal for families or a lucrative investment. with a BONUS Building serving as as a Cozy 1 bed/1bath guest quarters for visitors. Opportunities for single family, a MULTI family, a peaceful vacation retreat, or a smart investment, this property offers endless possibilities. Enjoy breathtaking views, a tranquil environment, and the ultimate waterfront lifestyle. Dont let this extraordinary opportunity pass by!.. Seller Finance considered, call for details!

$1,300,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,360 SqFt Days Listed: 92
-10.28% ($149,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Lift50ft

Welcome to the Keys Life Getaway! Located in the desirable Tavernier neighborhood of Plantation Key Colony, this fully furnished 3 bedroom, 3 bathroom concrete canal home is awaiting your arrival. Relax under the lanai and watch the manatees play and the tarpon roll right off of your 50ft dock. Situated on a deep water canal, youll enjoy quick access to Florida Bay or the ocean via Tavernier Creek and convenient boat fuel at the end of your canal. Inside, the home features a great floorplan for entertaining, tile floors throughout, a well appointed kitchen with plenty of storage, stainless steel appliances and a separate wine fridge. The exterior features low maintenance landscaping, a 15,000lb boat lift, jet ski davit and a storage shed. The neighborhood features a wonderful bayfront homeowners park where you can launch your boat or relax and watch the sunset! The boat ramp was recently renovated and features a new concrete ramp and dock. Optional membership to the homeowners park is $250/year. The home is conveniently located near Coral Shores High School, Plantation Key Elementary School, shopping, grocery, bars & restaurants. This home will make a great full-time residence, or 2nd home with the ability to generate vacation rental income.

$1,325,000
Key Largo
Pirates Cove   - MM: 98.50
3 Bed, 3 Baths, 1,350 SqFt Days Listed: 263
-9.68% ($142,000) 2 Price Changes : Last Change 126 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Ramp6

Prestigious Pirates Cove - Secluded Lake/Front Basin Home - Direct Ocean & Bay access in just minutes - 3Bed/2 Baths - The Upper Level is a 2 Bedroom/ 1 Bathroom & Lower Unit is a **Grandfathered in designated 1Bedroom/1 Bathroom with a Full Kitchen. Solid Concrete Dock equipped with a 15000 LB boat lift & Separate Jet Ski lift -Also property is Secured by an Electric Gate & Fenced in Yard complete with Shaded Patio area with Pavers and Tropical Landscaping - fish cleaning station & storage. Centrally located near Shopping, Schools & Restaurants.

$1,369,000
Plantation Key
Indian Waterways   - MM: 89.00
2 Bed, 2 Baths, 1,148 SqFt Days Listed: 82
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Boat

Waterfront Canal Home located in the Best Islamorada Plantation key Location. Great Vacation Rental is being sold furnished . Turnkey with 5 star reviews ! Large bedrooms with King Beds. Metal Roof , Smart TVs, Quartz countertops , open kitchen , Modern bathrooms, Great living room with open kitchen, Washer & Dryer, Screened in wrap around porch overlooking the water. 60 of Canal Frontage. HUGE enclosed Garage area underneath that can be extra living space New AC, New appliances, large yard area plenty of parking , 60 Private Dock , Beautifully remodeled. Large enclosed garage under home , Close to Founders Park with access to pickleball. swimming Pool , Beach, tennis and more. Own your own slice of paradise

$1,375,000
Key Haven
Key Haven 3rd Add   - MM: 5.00
2 Bed, 2 Baths, 1,080 SqFt Days Listed: 117
-9.84% ($150,000) 3 Price Changes : Last Change 31 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 60ft.Concrete

This fully upgraded 2 bedroom 1 bathroom canal front home offers open water views and deep water access. Completely renovated, plumbing, electrical, impact doors and windows, custom cabinetry in kitchen and bath, porcelain countertops and backsplash, built in closets and electric water heater. A brand-new 60 x 8 concrete seawall adds durability and value. Enjoy coastal living and island life just minutes from Key West!

$1,375,000
Key Largo
Cross Key Waterways   - MM: 103.00
5 Bed, 5 Baths, 2,027 SqFt Days Listed: 109
-11.29% ($175,000) 3 Price Changes : Last Change 1 Day Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat LiftConcrete

Amazing Three-Story Waterfront Haven in Cross Key Waterways, KEY LARGO! Embrace the allure of coastal living in this impressive 5-bedroom, 4-bathroom Key Largo retreat. This waterfront charm provides abundant living space for you and your loved ones with large open balconies off each floor. This property have a 40-foot dock, and a 15,000-pound lift that effortlessly hoists your vessel. The loft space awaits--a canvas of possibilities for a home office, entertainment area, or even a tranquil retreat with captivating views. This property can be rented for a mininum of 28 days. Only one hour away from Miami. 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 06-20-2025.
Back To TopMore Info
Terms / Privacy / Accessibility ADA