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

Total Listings 379
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$2,299,000
Key Largo
Key Largo Trailer Village   - MM: 101.50
3 Bed, 3 Baths, 1,250 SqFt Days Listed: 37
+2.68% ($60,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift175ft.Concr

Welcome to CASA DEL BOTE an Oasis at Tarpon Basin, Your Dream Waterfront Retreat!Step into a world of tranquility with this exceptional bay-front property, where breathtaking sunsets and the soothing sounds of the water are a daily delight. Nestled behind a custom gate, this stunning home is a hidden gem that promises privacy and serenity, all while offering over 175 feet of pristine waterfront, complete with your very own sandy beach. As you approach, the pavered driveway guides you to this beautifully remodeled 3-bedroom, 2-bath haven, designed for both comfort and style. The thoughtfully crafted split floor plan allows for seamless living, with ample space for both relaxation and entertaining. Beautiful water views frame your experience from almost every room, inviting the outside in and creating a serene ambiance throughout the home. The spacious master suite is a true sanctuary, featuring expansive windows that showcase the shimmering waters of the basin. Imagine waking up to the gentle lapping of waves and stepping onto your private balcony with your morning coffee in hand. The second bedroom also boasts enchanting water views, making it a perfect guest room or a cozy retreat for family. The heart of this home lies in its open living and dining areas, where the natural light pours in, and the inviting atmosphere beckons. The modern kitchen is equipped with stainless appliances and ample counter space, perfect for both intimate gatherings and grand celebrations. Step outside into your own private paradise, where outdoor living takes center stage. The recently resurfaced pool sparkles under the sun, inviting you to take a refreshing dip or lounge poolside with a good book. The property features a convenient boat lift and PWC lift, making it easy to embrace the coastal lifestyle and explore the crystal-clear waters at your leisure. Safety and efficiency are paramount, with impact windows/doors throughout the home and a newer metal roof. Its a lifestyle.

$2,300,000
Lower Matecumbe
Fantasy Harbor   - MM: 77.00
3 Bed, 3 Baths, 2,000 SqFt Days Listed: 207
-4.17% ($100,000) 1 Price Change : Last Change 40 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Basin99ft.

Make all of your Florida Keys fantasies come true at Fantasy Harbor! Were willing to bet you never even knew this gated community on Islamoradas Lower Matecumbe existed. This concrete harborfront home is being offered for the very first time. Upstairs 2 bedroom 2 bathrooms suites with open and spacious harborview living areas plus downstairs bedroom and bathroom with a bonus party hut reminiscent of relaxing Bahamian nights after a day on the water. Quiet & private living situated just off the Florida Bay in a protected harbor with 99 concrete seawall on cap rock plus boat lift. This one is a winner!

$2,300,000
Big Pine Key
Doctors Arm   - MM: 30.50
4 Bed, 4 Baths, 2,400 SqFt Days Listed: 23
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: 132
-8.00% ($200,000) 1 Price Change : Last Change 66 Days Ago
Single Family - Active - 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: 128
-10.00% ($260,000) 1 Price Change : Last Change 3 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!

$2,375,000
Key Largo
Lake Surprise Properties   - MM: 106.00
5 Bed, 5 Baths, 3,184 SqFt Days Listed: 76
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: 52
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!

$2,395,000
Lower Matecumbe
Port Antigua   - MM: 74.50
4 Bed, 4 Baths, 2,082 SqFt Days Listed: 200
-2.24% ($55,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 60ft.

GREAT LOCATION WITH PRIVATE COMMUNITY BEACH!!! STUNNING 4 BED 3 BATH WELL-BEAUTIFULLY MAINTAINED PORT ANTIGUA POOL HOME WITH 3 BEDROOMS 2 BATHS UPSTAIRS AND AN ADDITIONAL LIVING AREA, KITCHENETTE, 1 BEDROOM, AND 1 BATH DOWNSTAIRS IN THE HIGHLY SOUGHT AFTER PORT ANTIGUA NEIGHBORHOOD* SPACIOUS OPEN LAYOUT WITH TONS OF NATURAL LIGHT* ENJOY POOL AND CANAL WATERVIEWS FROM MOST OF THE HOME* LUSHLY LANDSCAPED LOT ADDS PRIVACY - PERFECT FOR ENTERTAINING & FAMILY GATHERINGS OR JUST RELAXING IN YOUR OWN TROPICAL OASIS WITH OUTDOOR SHOWER* ENJOY THE BREEZE FROM THE LARGE COVERED BALCONY UPSTAIRS OVERLOOKING CLEAR BLUE WATER OF THE POOL AND CANAL OR DOWNSTAIRS COVERED ENTERTAINMENT AREA* PAVER DRIVEWAY EXTENDS FROM STREET TO DOCK* T-DOCK HAS WATER AND FISH FILET STATION. PORT ANTIGUA OFFERS ACCESS TO PRIVATE BAYFRONT HOMEOWNERS PARK WITH FABULOUS SUNSET VIEWS FROM A GLORIOUS WHITE SAND PORT ANTIGUA BEACH, TIKI HUTS FOR ENTERTAINING, AND A PRIVATE BOAT RAMP* THIS TURN-KEY HOME IS PERFECT AS A PRIMARY RESIDENCE OR THE BEST VACATION SPOT* BRING YOUR OFFERS AND OWN A PIECE OF PARADISE IN THE FLORIDA KEYS

$2,399,000
Big Pine Key
Tropical Bay   - MM: 30.50
3 Bed, 3 Baths, 2,134 SqFt Days Listed: 123
-3.85% ($96,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip75ft.Concre

Discover the epitome of waterfront living at Tropical Bay Estates. This fully furnished, 2023 new construction home offers an unparalleled paradise for your family and friends. Begin your days with stunning sunrises, engage in world-class fishing, and soak in breathtaking water views from nearly every part of the house. Encounter the charming key deer in this serene neighborhood.Built with full CBS construction, this residence stands on 10-foot-high stilts and features 10-foot-high ceilings with 8-foot-high doors, ensuring both luxury and durability for tropical storms. The backyard is a haven for boating enthusiasts, featuring an 8-foot-deep boat slip and a 75-foot concrete seawall, complemented by a heated saltwater pool. Inside, the home spans over 2,000 square feet, showcasing an open floor plan that accentuates water views from almost every corner. Additionally, a versatile bonus room on the lower level can serve as an entertainment space or be converted into an extra bedroom.With impact windows, a durable metal roof, and all furnishings and appliances included, this residence is truly move-in ready--ideal for a family home or a high-end rental property. Contact us today for a private showing and experience the luxurious lifestyle that awaits you at Tropical Bay Estates.

$2,399,000
Marathon
Key Colony Subdivision   - MM: 53.00
4 Bed, 4 Baths, 2,304 SqFt Days Listed: 20
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
Twin Lakes   - MM: 103.00
3 Bed, 3 Baths, 2,153 SqFt Days Listed: 85
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
Tarpon Acres   - MM: 102.00
2 Bed, 2 Baths, 828 SqFt Days Listed: 44
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
Lake Surprise Estates   - MM: 106.00
4 Bed, 4 Baths, 2,262 SqFt Days Listed: 51
-9.26% ($250,000) 1 Price Change : Last Change 1 Day 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.

$2,475,000
Key Largo
Hammer Point   - MM: 93.00
4 Bed, 4 Baths, 3,140 SqFt Days Listed: 331
-23.85% ($775,000) 3 Price Changes : Last Change 163 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 57ft.

This three level, 4 bed/ 4 bath home has a private third-floor master suite with a large den and balcony. The great room, bathed in natural light, offers stunning bay views, and the expansive rooftop deck is perfect for enjoying splendid sunset vistas.The ground level is an entertainers dream, featuring a large media room, inside laundry, kitchenette/wet bar, full bathroom, and a fourth bedroom or den that opens directly onto the pool deck. Outside, enjoy the pool with a paver deck and covered patio, or relax on the concrete dock with direct bay access and convenient ocean access via Tavernier Creek.Custom features such as elevator, tongue and groove ceilings throughout the great room, built-in closets, and tall doors opening to porches on all levels add to the homes charm and style. This is a fantastic opportunity to customize a spacious waterfront home to your tastes.

$2,490,000
Key Largo
Buccaneer Point   - MM: 98.00
4 Bed, 4 Baths, 3,317 SqFt Days Listed: 160
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.

$2,495,000
Lower Matecumbe
Port Antigua   - MM: 74.50
3 Bed, 3 Baths, 1,560 SqFt Days Listed: 57
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits60ft.Concrete

This is the one you have been waiting for! This home has been UPDATED beautifully and has 3 bedrooms and 2 baths on the main living level. It is just waiting for a new family to begin living their best Port Antigua life! The downstairs breezeway affords a large shady area for entertaining or relaxing. Upstairs you will be greeted by an open expansive floor plan. All the windows and doors are now impact resistant and the CBS construction and concrete roof will give you peace of mind if there is a storm on the horizon. The main living level features an open floor plan with the kitchen, dining and living areas spanning the canalside of the home. All the bedrooms have ample closet space and the laundry room provides additional storage. On the ground level there is a very large storage enclosure for all of your boating paraphernalia that needs to be kept out of the weather and a large open entertaining area. Dont delay, this could be your dream home in Port Antigua!!

$2,499,000
Big Coppitt
Porpoise Point Sec 5   - MM: 10.00
4 Bed, 4 Baths, 2,523 SqFt Days Listed: 37
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.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.

$2,499,999
Lower Matecumbe
Port Antigua   - MM: 74.50
3 Bed, 3 Baths, 2,432 SqFt Days Listed: 454
-13.79% ($400,001) 3 Price Changes : Last Change 2 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: 23
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.

$2,575,000
Key Largo
Hammer Point   - MM: 93.00
4 Bed, 4 Baths, 2,508 SqFt Days Listed: 38
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!

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 05-10-2025.
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