Divider
Content Divider

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

Total Listings 280
Order By:

$2,300,000
Big Pine Key
Doctors Arm   - MM: 30.50
4 Bed, 4 Baths, 2,400 SqFt Days Listed: 60
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges

FINISHED -- NEW CONSTRUCTION!!! Luxury water view home with an in-ground pool on a 14,680 sq ft lot with dock and boating access. Brand new single level elevated CBS home over parking. Impact windows and doors, metal roof, 10-foot interior ceilings, stainless appliances and much more. Construction is completed, ready for occupancy.The property has a beautiful view over the water and a magnificent bridge that is rarely used due to the fact that only a few homes are on the other side of the bridge.

$2,300,000
Lower Matecumbe
Port Antigua   - MM: 74.50
2 Bed, 2 Baths, 1,178 SqFt Days Listed: 169
-8.00% ($200,000) 1 Price Change : Last Change 94 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

This solid concrete home is located in one of Lower Matecumbes most sought-after subdivisions, offering 75 feet of prime waterfrontage on a peaceful canal with serene nature views--no neighboring homes across canal. The ground level features a permitted bath, a spacious workshop, and a carport with soaring high ceilings, providing ample storage.Enjoy your private slice of paradise with a dock complete with a Tiki hut for shade, and a 16,000 lb. 4-post boat lift, ideal for boating enthusiasts. The expansive backyard offers plenty of space to build your dream pool.With a little polish, this gem has endless potential to become your perfect waterfront oasis! Dont miss out on this unique opportunity!

$2,340,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
5 Bed, 5 Baths, 2,447 SqFt Days Listed: 165
-10.00% ($260,000) 1 Price Change : Last Change 26 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat RampConcrete

Escape to paradise! 5BR/3.5BA gated home in the Keys. Bamboo floors, fresh paint, screen patio. Elegant accents. Lush landscaping, private pool, hot tub. 2 levels, full bar, gourmet kitchen, walk-out patio. Master w/ walk-in closet. Stargaze from wrap-around porch. Must see this private oasis!

$2,349,000
Big Coppitt
Porpoise Point Sec 5   - MM: 10.00
4 Bed, 4 Baths, 2,523 SqFt Days Listed: 74
-6.00% ($150,000) 1 Price Change : Last Change 10 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat LiftConcrete

Waterfront Paradise for Anglers & Entertainers - Perfect for Family, Friends & Vacation Rentals.Welcome to the Ultimate Waterfront Luxury Retreat, Completely remodeled and redesigned for those who love to entertain. Excellent deep water access and yet just minutes to all the action downtown Key West has to offer.Seller will consider Owner Financing/Private Financing or even a full or partial trade. Elevated and storm resistant concrete construction, this home offers unmatched durability while embracing a modern coastal lifestyle.With four Spacious bedrooms and four beautifully appointed bathrooms, this home comfortably accommodates large groups with almost 2500 Sq Ft. interior Space. The newly finished open-concept dream kitchen is designed for socialising, featuring an oversized Island, seating up to 12 guests, making it the ideal host house for unforgettable gatherings and events.On the Second Floor, this dream home continues with a stunning custom built bar and lounge offering the ideal spot to start the party, watch a game or wind down after an exhilarating day on the water. The adjacent waterfront balcony sets the stage for relaxing and entertainment.The outdoor experience is just as impressive, featuring a large pool, hot tub, New Tiki Hut for those looking for shade, boatlift, concrete patio and game room - perfect for guests of all ages to enjoy. Excellent off Street parking for multiple vehicles, Boat Trailers or RV on over 9000 Sq. Ft. Lot.Whether you are heading out for world class fishing, or simply unwinding by the water, this Keys Home delivers the ultimate Florida Keys lifestyle.

$2,375,000
Key Largo
Lake Surprise Properties   - MM: 106.00
5 Bed, 5 Baths, 3,184 SqFt Days Listed: 113
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 60ft.

Experience the pinnacle of coastal luxury in this brand-new waterfront residence in Key Largo. Featuring five spacious bedrooms and three elegantly appointed bathrooms, this home is crafted with solid concrete construction, ensuring durability and peace of mind.Enjoy breathtaking bay views from the expansive rooftop deck--an ideal setting for entertaining or unwinding as the sun sets over the water. A modern, resort-style pool at the waters edge provides the perfect retreat after a day on the ocean, while the brand-new concrete dock offers a secure haven for your boat, with deepwater access to both the ocean and bay.Inside, this stunning home boasts impact windows and doors, elegant tiled floors throughout, and a chefs kitchen with a waterfall-edge sit-up island, premium appliances, and abundant natural light. A luxury elevator adds convenience, while the spacious covered understory--complete with a workshop and storage area--is perfect for housing all your fishing and boating gear.Located just one hour from Miami International Airport, this tropical paradise offers the perfect blend of exclusivity and accessibility.

$2,395,000
Lower Matecumbe
Port Antigua   - MM: 74.50
2 Bed, 2 Baths, 1,228 SqFt Days Listed: 89
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift70ft.Concre

What does everyone want? The smallest house in the best neighborhood! This is the one! This home has been beautifully updated and is being sold furnished including kitchen wares, dishes and linens. Dont worry about the weather, impact windows and doors have been installed throughout including the 3 skylights in the concrete roof! The pleasing open floor plan will easily accommodate your friends and family and triple sliding glass doors open to the second floor terrace. A separate laundry room is conveniently located by the kitchen. Both bedrooms have sliding glass doors to an open terrace that let in lots of natural light. Downstairs youll find ample storage and a 70 ft. concrete dock with fishcleaning stand and boat lift. The yard is very low maintenance with river rock in the front with a nice concrete driveway and artificial turf in the back. This is the one youve been waiting for, easy Keysy living in Port Antigua!

$2,399,000
Marathon
Key Colony Subdivision   - MM: 53.00
4 Bed, 4 Baths, 2,304 SqFt Days Listed: 57
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Other Dock

Waterfront Pool Home with Deep-Water Dockage & Direct Gulf Access!Welcome to 10980 3rd Avenue Gulf -- a true boaters paradise tucked away on an oversized private lot along a wide and deep canal. With multiple dockage options for large boats, a boat lift, and instant Gulf access (plus ocean access just minutes away via Vaca Cut), this property is ideal for serious anglers and water enthusiasts alike.This well-maintained home offers spacious living areas, a nicely updated kitchen with granite countertops, and a tranquil screened-in porch perfect for relaxing after a day on the water. The layout is open and inviting, providing plenty of room to entertain and unwind.Step outside to enjoy the screened-in pool, covered patio, summer kitchen, and generous yard space. With ample parking, a detached garage, and all the must-have outdoor features -- including a boat dock, lift, and fish cleaning station -- this home offers everything you need for effortless Keys living.

$2,450,000
Key Largo
Tarpon Acres   - MM: 102.00
2 Bed, 2 Baths, 828 SqFt Days Listed: 81
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Basin

Awe-Inspiring Sunsets at this Quaint Bayfront Estate with Old World Charm! Peaceful and tranquil grounds overlooking the shimmering bay. Zoning is Suburban Commercial offering limitless investment possibilities. The main home has Dade County Pine throughout, Cuban tile and cathedral ceilings. Just steps away is a spacious two-car garage. Dock your boat and fish off the jetty or sunbath at your private lagoon along Tarpon Basin. This estate offers 1 acre of land with 100 of bay front and lagoon. Premier location in the heart of Key Largo. Close to shopping, restaurants, and easy commute to Miami. Delight in all the Florida Keys has to offer: Boating, swimming, snorkeling, world class fishing, and scuba diving. This estate is shown by appointment only. 24 hours notice for showings. Rogo letter in file. Sale of Property Subject to Court Approval.

$2,450,000
Key Largo
Twin Lakes   - MM: 103.00
3 Bed, 3 Baths, 2,153 SqFt Days Listed: 122
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift75ft.

Exquisite Canal Front Pool Home with 75 Concrete Dock!Experience the pinnacle of modern island luxury in this stunning 3-bedroom, 2.5-bathroom residence, perfectly situated on an expansive 9,750 sq. ft. lot. Designed with precision and elegance, this concrete home offers a metal roof, and impact windows & doors.Step inside to a spacious open-concept floor plan, where 10 ceilings and 8 doors create an airy, grand ambiance. A custom trim package enhances the space, adding a refined touch of sophistication. The gourmet kitchen is a chefs dream, featuring custom cabinetry, quartz countertops, making culinary creativity effortless.The expansive, tiled terrace overlooks a sparkling pool surrounded by lush tropical landscaping, creating a private oasis for relaxation and entertaining. Boating enthusiasts will appreciate the 75 concrete dock, offering direct access to both the Florida Bay and Atlantic Ocean, ensuring endless water adventures at your doorstep.A paver driveway enhances the homes curb appeal, further showcasing the meticulous attention to detail in every aspect of this exceptional property.Dont miss this opportunity to own a piece of island paradise and discover the perfect blend of luxury, comfort, and waterfront living.

$2,450,000
Key Largo
Lake Surprise Estates   - MM: 106.00
4 Bed, 4 Baths, 2,262 SqFt Days Listed: 88
-9.26% ($250,000) 1 Price Change : Last Change 28 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 60ft.

Stunning Brand-New Waterfront Home - 4 Bed / 3 Bath with 60 Dock and Pool. Luxury waterfront living in this elevated home. Step inside to a modern, open concept design with gorgeous white tile floors throughout, creating a sleek airy feel. The spacious living and dining areas flow seamlessly to the outdoor oasis where you will find your private pool perfect for relaxation and entertaining. With the elevated construction and impact windows, youll have a peace of mind. The canal opens up on to Blackwater Sound with easy access to the Ocean thru Adams Cut. Just 45 minutes from Miami, this weekend Oasis is waiting for you. **SELLER FINANCING AVAILABLE**

$2,450,000
Key Largo
Twin Lakes   - MM: 103.00
4 Bed, 4 Baths, 2,929 SqFt Days Listed: 20
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp

The dream home youve been waiting for has finally hit the market! This stunning Key Largo retreat sits on an oversized lot with 75 feet of waterfront, offering the perfect blend of space, style, and functionality. With four bedrooms, three baths, and soaring ceilings, this nearly 3,000-square-foot residence is designed for both comfort and entertaining.Step outside to enjoy the sparkling 13x30 pool featuring a sun shelf and cascading water features--just one of many outdoor entertainment areas. Whether youre launching a kayak or paddleboard from your private dock or utilizing the 15,000-pound boat lift, youre set for endless days on the water. Have a larger boat? No worries--just south of the property, a spacious turning basin makes maneuvering a breeze.Inside, the upper level boasts three bedrooms, two of which serve as primary suites. The open-concept living and kitchen area, flooded with natural light, leads to a large balcony overlooking the pool and canal--perfect for outdoor dining and sunset views. Ocean and bay access couldnt be easier, with Adams Cut just to the north, ensuring quick passage for all your nautical adventures.This move-in-ready home is packed with valuable upgrades, including a new AC unit, newer roof, modern appliances, updated electrical and plumbing, plus impact windows and doors for peace of mind. Additional perks include washer/dryer sets upstairs and downstairs, solar panels to offset electric costs, a paved driveway, abundant storage, a covered bar area by the pool, and lush, mature landscaping for added privacy.A rare waterfront gem--dont miss the chance to make it yours!

$2,490,000
Key Largo
Buccaneer Point   - MM: 98.00
4 Bed, 4 Baths, 3,317 SqFt Days Listed: 197
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

Welcome Home this is the MasterPiece On Mutiny. New Swimming Pool, Perfectly positioned near the tip of Buccaneer Point, this secluded estate, on its large lot with over 160 ft of waterfront, offers privacy and extended open water views. Designed and developed to his specifications, by a local builder for his family, no expense was spared. The 3,450 sq. ft. , with 5 bedrooms and 4 baths POOL home boasts expansive open and covered terraces to take full advantage of the scenic surroundings. The 11.3 KW photovoltaic array provides approximately 90% of the homes energy usage. This property brandishes so many details, that they are best appreciated in person. Truly a one of a kind Florida Keys retreat.

$2,499,000
Key Haven
Key Haven 7th Add   - MM: 6.00
3 Bed, 3 Baths, 2,090 SqFt Days Listed: 186
-13.68% ($396,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 72ft.

Open Water, Elevated, Concrete Home in best Waterfront community with easy proximity to Key West. 117 Key Haven Road was built to stand the test of time. With its Elevated concrete construction, metal roof and impact windows and doors, this home offers excellent protection of your investment and safety for your family and high quality comfort.Its combination of large 9300 sq ft. lot, excellent deep water access and stunning open water views of the bay and Gulf of Mexico make this an amazing opportunity for the buyer looking for a waterfront home.Configured as a 3BD/2BA, all on one elevated level with master suite and wrap around balcony overlooking the open water.Renovated kitchen with stainless steel appliances and beautiful granite countertops provides excellent space to prepare and enjoy a dining experience.Two separate single car garages offer ample storage, additional off-street parking and boat trailer parking also available.Large concrete deck in the rear offers many options to those who love to entertain and enjoy the outdoors. Plenty of room for a pool and property can accommodate multiple boats.

$2,499,999
Lower Matecumbe
Port Antigua   - MM: 74.50
3 Bed, 3 Baths, 2,432 SqFt Days Listed: 491
-13.79% ($400,001) 3 Price Changes : Last Change 36 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits65ft.

Welcome to this exquisitely designed home located in beautiful Port Antigua. This is an entertainers delight featuring marble flooring throughout the home. It boasts 2 full kitchens, one of which is outdoors so you can bring your fresh catch in from the boat and start cooking immediately while the smell of night blooming jasmine envelops you.There is a fully fenced in yard for your furry friends. Youll have a 65 foot dock for your boat to spend days on the crystal clear blue waters that surround our beautiful islands.This home has 3 bedrooms and 3 1/2 baths, a beautiful indoor bar with the ability to add another shower in the downstairs half bathroom.Youll be proud to call this house home.

$2,500,000
Key Haven
Key Haven 10th Add   - MM: 5.00
3 Bed, 3 Baths, 2,685 SqFt Days Listed: 60
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 20ft.

Stunning Waterfront Oasis in Key Haven - Elevated 3BR/3BA Home with Boating AccessWelcome to 37 Evergreen Ave. in Key Haven, Key West! Nestled at the end of a peaceful cul-de-sac, this beautifully updated 3-bedroom, 3-bathroom waterfront home offers the perfect blend of elegance and comfort. With 2,685 square feet of elevated living space on a generous 10,290 sq ft lot, every detail of this residence has been thoughtfully designed.Step inside to a light-filled large living room open to the waterfront balcony and an adjoining dining area--perfect for entertaining or simply relaxing with family and friends. The first floor also features a spacious updated kitchen with granite countertops, hardwood cabinetry, and stainless steel appliances. Upstairs, the expansive master suite serves as a true sanctuary, complete with a spa-style ensuite bathroom, large closets, and multiple French doors that open to a private balcony. The two additional bedrooms also offer balcony access.The home is elevated and equipped with hurricane-impact windows and doors and a full house generator providing peace of mind year-round. Enjoy the fresh coastal breeze from balconies off every room, or head downstairs to your private waterfront yard with direct boating access to open water offering access to the Gulf or Atlantic for fishing, diving, or sunset cruising.Additional highlights include a freshly painted interior and exterior, an enclosed air conditioned garage, and a paved driveway offering ample parking.

$2,500,000
Key Largo
Twin Lakes   - MM: 103.00
3 Bed, 3 Baths, 1,830 SqFt Days Listed: 15
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits50ft.Concrete

INVESTORS PARADISE!Situated on nearly 14,000 sq ft lot, this property offers premium access on a wide and deep canal, perfect for the ultimate boaters and savvy investors.Solidly built concrete construction and a concrete roof, the existing home features a 2-bedroom, 1-bathroom, and main living area upstairs, plus a Permitted 1-bedroom, 1-bath guest suite downstairs--ideal for guests or extended family.With ample space to expand, redesign, or completely reimagine, the oversized lot offers room for a luxury pool, extensive outdoor living areas, and additional square footage. This is a blank canvas and one of the most desirable Investment opportunities in the heart of Key Largo. Whether youre looking to renovate for personal enjoyment or unlock the propertys full investment potential, this is your chance to capitalize on size, structure, and location --bring your vision and create your slice of paradise.

$2,575,000
Key Largo
Hammer Point   - MM: 93.00
4 Bed, 4 Baths, 2,508 SqFt Days Listed: 75
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Boat R

ANCHOR in PARADISE! Breathtaking bay views from every corner of this stunning home in Hammer Point! Centrally located at MM93 in Tavernier, this incredible 4-bedroom, 3-bath retreat is just one house away from the open bay, offering a lifestyle of sun-soaked bliss. The second floor has 1/1 and the third floor 3/2 having the Master Suite with 2 additional guest bedrooms.Step outside to your private 37-foot dock, complete with a JetSki platform lift, perfect for all your water adventures! The property is gated and adorned with lush, meticulous landscaping & low-maintenance artificial turf, ensuring you spend more time enjoying the outdoors.Selling this fully furnished. This gem boasts spacious open rooms, high ceilings, & expansive balconies overlooking the Open Bay. The chef-style kitchen is a dream w/a massive island & newer appliances, perfect for entertaining family & friends. In the evenings, enjoy the outside underwater lights at the dock & view your personal aquarium!Throughout this elegant home, youll find beautiful tile flooring, a large laundry room, two new central AC systems, & Category five impact windows & doors. The Huge Private Master Suite offers a beautiful tropical clear glass edged in the master bath Shower and step up Tub for your ultimate relaxation. For Bonus we have, security cameras thru-out the property to keep an eye on your oasis while youre away.Freshly painted inside & out, this home radiates an Island vibe that perfectly complements its tropical setting. Whether youre seeking a family retreat, an upscale vacation rental, or both, this property has incredible potential, offering the opportunity to generate $100K or more with permissible 28-day rentals in the community.Dont miss out on this opportunity to ANCHOR in PARADISE!

$2,599,000
Lower Matecumbe
Port Antigua   - MM: 74.50
3 Bed, 3 Baths, 2,010 SqFt Days Listed: 85
-3.74% ($101,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift45ft.

Welcome to Port Antigua!This beautiful Key West-style home in Port Antigua boasts an open floor plan with a spacious kitchen featuring a large center island. The main living area on the second floor includes three bedrooms and two bathrooms, while the first floor offers an entertainment room that could serve as a fourth bedroom.Two sets of sliding glass doors lead to a screened-in porch overlooking the canal, perfect for enjoying the waterfront views. The home is equipped with high-impact-resistant windows and doors for added security and energy efficiency.Boaters will appreciate the 45-foot concrete dock with a 15,000 lb-rated boat lift, making it easy to enjoy life on the water. As part of Port Antiguas Homeowners Association, residents have exclusive access to a private beach with breathtaking year-round sunsets.This is a fantastic opportunity to embrace the Keys lifestyle--dont miss out!

$2,600,000
Key Largo
Hammer Point   - MM: 93.00
5 Bed, 5 Baths, 2,586 SqFt Days Listed: 103
-10.19% ($295,000) 1 Price Change : Last Change 30 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift58ft.

Motivated Seller has made a significant price adjustment to this stunning home. Enjoy Bay Views from this custom waterfront residence. Home of crystal clear canals and nightly sunsets, Hammer Point is located on the south end of Key Largo and provides excellent boating access for both ocean & bay enthusiasts. Built in 2008, this masterpiece offers five bedrooms & three bathrooms, coastal design, light and classic decor, a private elevator with access to each level, chefs kitchen, large open living with soaring ceilings, generous outdoor living, concrete construction & a metal roof. Relax & unwind as you take in the breathtaking views offered from this private sanctuary. The outdoors provides wonderful space for entertaining, outdoor kitchen, turf grass, chiki, and full concrete dock & boat lift. To complete this package, this home is being offered furnished, and owner financing is offered to qualified buyer.Dont let this opportunity pass you by.

$2,650,000
Key Largo
Hammer Point   - MM: 93.00
3 Bed, 3 Baths, 2,156 SqFt Days Listed: 111
-17.16% ($549,000) 3 Price Changes : Last Change 26 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Immerse yourself in the ultimate Florida Keys lifestyle with this stunning waterfront retreat, offering breathtaking bay views, unparalleled boating access and fully furnished. Newly remodeled in 2024, this exceptional home is a dream for boating enthusiasts, featuring immediate bay access and just minutes from Tavernier Creek. Nestled in the highly sought-after Hammer Point subdivision of Tavernier, this exquisite two-story residence sits on a pristine, gin-clear canal and boasts a 72-foot concrete dock with a 15,000lb boat lift. The exterior is crafted from PECKY CYPRESS WOOD, known for its distinctive natural grooves and outstanding durability. The pecked areas add visual character without affecting the woods strength, making it as sturdy and decay-resistant as standard cypress. Inside, the three-bedroom, two-bath home showcases soaring ceilings, rich wood finishes, and an abundance of natural light streaming through skylights and sliding glass doors. The inviting layout seamlessly blends indoor and outdoor living, with bay views visible from the living room, kitchen, covered balcony, and first-floor entertainment area. The enclosed lower level provides a versatile space perfect for guests, a playroom, or a home gym, while the spacious attached garage offers ample storage and a dedicated area for hobbies. The crown jewel of the property is the rooftop deck, where you can take in breathtaking, unobstructed views of Florida Bay and its mesmerizing sunsets--turning every evening into a work of art. Ideally located just minutes from Tavernier Creek, this waterfront paradise provides effortless access to both the Bay and the Ocean, allowing you to explore the enchanting waters and vibrant reefs of the Florida Keys. Whether youre looking for a permanent residence or a vacation escape, this extraordinary home is ready to welcome you--schedule your showing today and step into the lifestyle youve always dreamed of!

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 06-16-2025.
Back To TopMore Info
Terms / Privacy / Accessibility ADA