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

Total Listings 317
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$6,690,000
Key Largo
Tarpon Acres   - MM: 102.00
5 Bed, 5 Baths, 2,364 SqFt Days Listed: 104
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin,Boat Ramp

Welcome to the ultimate tropical sanctuary in Key Largo! An extraordinary waterfront estate spanning over 2.5 acres along Tarpon Basin. This breathtaking property offers unparalleled sunset vistas, a coral jetty framed by a lagoon, a boat ramp, lush mangroves, and a canopy of majestic mahogany trees.Green sloping land is elevated for privacy and optimal protection . The estate features two impeccably remodeled homes with high-end finishes. The main house includes three bedrooms, four elegantly appointed bathrooms, a full kitchen, and spacious living areas. The second home offers two beautifully crafted bedrooms, two luxurious bathrooms, and a full kitchen. Both homes are adorned with lavish spa-like bathrooms and hand-carved, imported Bali doors and casings.The Suburban/Commercial Zoning offers limitless investment possibilities, or a private sanctuary, a high-end vacation rental, an exclusive event venue, or a family compound. Imagine creating an oversized dream home surrounded by tropical splendor.Just 65 minutes from Miami International Airport, this one-of-a-kind estate is perfect as a peaceful hideaway, a lucrative income property, or a stunning family compound. Create your private sanctuary and embrace the essence of the Florida Keys lifestyle.

$6,699,000
Key Haven
Key Haven 10th Add   - MM: 5.00
6 Bed, 6 Baths, 6,611 SqFt Days Listed: 55
-4.29% ($300,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift200ft.

This Key Haven Estate rests on over 15,000 square feet of land with more than 260 linear feet of water access all while boasting over 6500 square feet of the finest living accommodations in the Florida Keys. The main Home has 5 Bedrooms and 4 and 1/2 bathrooms, the guest house has 3 bedrooms and 3 bathrooms. 39 Evergreen has the finest finishings all encased in 11 inches of solid concrete using insulated concrete forms and solid poured floors and stairs. Utilizing this type of Construction not only provides tremendous safety and privacy but allows for the impact glass windows and doors to be protected by hidden European style roll down shutters. The home has a vast 60 long pool with multiple levels, waterfalls and 6 seats to the swim up bar in the custom gazebo, perfect for entertaining, or when you are finished in the homes Private 400+ Square foot Gym. This home can accommodate over 9 vehicles in its 3800 Square Foot garage and has a Generator and Fire Suppression system for additional safety and security.

$6,900,000
Lower Matecumbe
Toll Gate Shores   - MM: 73.50
4 Bed, 4 Baths, 3,907 SqFt Days Listed: 9
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Slip7

Experience the perfect blend of elegance and tropical charm in this exquisite luxury home in Islamorada. This four-story residence offers breathtaking bay views from every level and features over 70 feet of protected dockage with immediate bay access and quick ride to oceanside via Chanel 2 or Channel 5 bridge, perfect for boating enthusiasts. With four bedrooms and four and a half baths, the spacious layout includes three laundry rooms and an elevator for convenience. The outdoor area boasts a heated and chilled pool with limestone decking, built in grill, custom wet bar, and a covered living space ideal for entertaining. The chefs kitchen features luxurious quartz countertops, top-of-the-line appliances, and a stylish glass tile backsplash. The expansive primary suite occupies the entire fourth floor, complete with a private sitting room, balcony, and a luxurious en-suite bath. Each bedroom also has its own balcony to enjoy stunning sunsets. Additional highlights include impact windows, a fully air-conditioned tackle room/workshop and garage, and can accommodate a 42 RV with sewer and 50 amp service. Beautifully landscaped with Royal Palms and tropical plantings, this home offers the unique opportunity to enjoy upscale Keys living with modern amenities and glorious water and sunset views. Perfect for those seeking a turnkey property in an idyllic location.

$6,900,000
Plantation Key
Sunshine Estates   - MM: 90.50
3 Bed, 3 Baths, 2,459 SqFt Days Listed: 20
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Ramp

Sunset Haven This absolutely delightful and serene Florida bayfront beauty will take your breath away the moment you walk in. Delightful double primary ensuite layout and open porches and patios galore adorn this fresh feeling home. 180 degree open water views complete nightly with painted sky sunsets and the best boating proximity; just a stones throw to the Intracoastal waterway and both Tavernier Creek and Snake Creek for easy Bay to Ocean access. 108 of protected dockage with ramp, boat lift and tiki, ample parking and plenty of room for a pool if you need one.

$8,300,000
Key Largo
Sunrise Point   - MM: 95.00
10 Bed, 10 Baths, 5,392 SqFt Days Listed: 127
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Other Dock

Magnificent bayfront estate with 2 homes plus a Keys Cottage. Enjoy year round sunsets from this 2 acre estate on Florida Bay! This is perfect for an extended family or group of friends to enjoy. 3 dwellings on 2 separate parcels plus deeded baybottom make this a truly unique property. Gated for privacy, the driveway passes the Coral House, which is used as a licensed vacation rental. Continue towards the bay where the Cottage and Florida Bay House are nestled into the mature tropical landscaping. Florida Bay is straight ahead with a jetty into the Bay which is the perfect spot for sunning or stargazing. The boatramp next to the jetty is handy for launching kayaks and paddleboards to explore Florida Bay. Originally built in 1961, the Florida Bay House was expanded in the early 70s and has 3 bedrooms and 3 baths with the master suite upstairs. The Cottage was built in 1956 and is a quaint guest house. The Coral House has 4 bedrooms and 3 baths, was built in 1992 and is in the X flood zone. Come and take a look and fall in love with this beautiful bayfront property.

$9,850,000
Key Largo
Buccaneer Point   - MM: 98.00
6 Bed, 6 Baths, 4,592 SqFt Days Listed: 91
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Welcome to this stunning bay-front contemporary single-family home located at 39 Mutiny Pl, Key Largo, FL. This exquisite residence spans 4592 square feet and offers 6 bedrooms, 5.5 bathrooms, and a wealth of luxurious amenities.As you step inside, youll be captivated by the architectural elements, including the developers signature spiral staircase and floor-to-ceiling windows that bathe the space in natural light. The home boasts a state-of-the-art Kef sound system, IP Smart Camera System, 20-foot bi fold accordion windows in entertainment area to completely immerse yourself with an outdoor/indoor experience creating an ideal setting for both relaxation and entertainment.The kitchen is a chefs dream, featuring top-of-the-line Miele appliances, porcelain countertops, cabinets finished with a stunning Caracalla Naturale Wood and beige Ovatta doors imported from Italy by Pedini Kitchens. The primary bedroom features a morning bar with refrigerator beverage center, LED Linear lights in the ceiling, dreamy views of the Bay, custom millwork decorative paneling and an oversized Italian master closet. The ensuite bathroom is a sanctuary of indulgence, with separate vanities, TOTO washlet smart toilet system, a soaking tub, dual shower system, finished in a porcelain tile imported from Spain.Outside, the property offers a below-ground saltwater pool, a private dock, and a fully turfed rooftop terrace, all showcasing breathtaking water views and perfect for entertaining. The outdoor space also includes an Al fresco appliances summer kitchen, a wet bar and golf putting green. The dock includes a 20,000-pound boat lift with space to add your own jet ski dock, another boat lift or a floating dock.

$9,995,000
Plantation Key
Key Heights   - MM: 88.50
5 Bed, 5 Baths, 3,389 SqFt Days Listed: 27
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Basin,Boat Li

The literal meaning of paradise comes alive here at Elysian Bay. Enter this stunning and incredibly reimagined bayfront residence exuding luxury living with the natural beauty of its coastal surroundings. Open-concept design showcases the panoramic Florida Bay views of the coveted high elevation Plantation Key location. The spacious living area features chefs kitchen, high ceilings, extra large Eurowall impact doors and windows highlighted by elegantly simplistic finishes. The primary suite overlooks the resort inspired gardens, enhancing your outdoor experience on the Bay. Additional guest bedrooms both upstairs and downstairs are beautifully designed, ensuring comfort and privacy for family and friends. Ample, multi boat protected dockage with lift, lounging beach, tiki torches, outdoor shower, jacuzzi, tackle house and lagoon waterfall pool outfit this property the perfect playground for all. Step outside and soak up the breathtaking sunsets where Elysian Bay offers quiet seclusion and the heavenly Islamorada lifestyle youve been waiting to embrace.

$10,500,000
Marathon
Crains Subdivision   - MM: 58.00
4 Bed, 4 Baths, 5,168 SqFt Days Listed: 89
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Morton Manor is a timeless estate nestled along the Gulfs bay waters, evoking a sense of simpler times. This boat basin is truly unique, offering not just protection from wind and waves with its jetties, but also accommodating 4 to 5 large vessels, from spacious center consoles to sportfish boats, thanks to its 8 depth. The home offers a resort-like experience reminiscent of the Caribbean, complete with amenities such as a sauna, a stunning bar and game room, a heated pool, and a private beach. This expansive, ground-level residence boasts 4 bedrooms, 4 bathrooms, a two-car garage, exposed wood beam ceilings, and a workshop. For those passionate about boating and seeking relaxation, Morton Manor is the ideal retreat.

$10,750,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
6 Bed, 6 Baths, 6,866 SqFt Days Listed: 127
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,BasinConcr

This exquisite bayfront Islamorada property features a main home with four bedrooms, four full bathrooms, and two half bathrooms, along with a guest house offering two bedrooms and one bathroom. The kitchen features marble countertops, a gas range, and counter seating. With a separate dining area and 30 ft high ceilings in the great room, floor-to-ceiling windows offer breathtaking views of the bay waters and dynamic sunset skies. The infinity edge pool with a spa offers reflections of beautiful palms and exquisite landscaping. The outdoor cabana kitchen is perfect for al fresco dining, and the boat basin with dockage allows for easy access to the waters of Florida Bay. A whole-house generator ensures uninterrupted comfort and tiki torches light the backyard terraces. Dont miss the waterfalls cascading into the boat basin, creating a truly serene retreat.

$10,900,000
Lower Matecumbe
Mat Sandy Beach   - MM: 75.00
4 Bed, 4 Baths, 4,512 SqFt Days Listed: 317
-5.22% ($600,000) 1 Price Change : Last Change 73 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Slip,

Unravel your dreams through this gated Estate Residence encompassing entire peninsula with over 500feet of bayfront and protected crystal clear waters. This pristine private luxury resort style property and residence includes designs by DAsign Source and provides ultimate privacy while exposing the surrounding majestic waters. Avid boaters will appreciate this dockage for multiple large boats, plus onsite boat ramp Y private boat lift. Marked features of this Estate include professionally designed infinity pool & waterfalls, jacuzzi, and salt water pond overlooking the bay, manicured lawns with 28 zone irrigation, extensive tropical landscaping, paver brick driveway, detached 2 car garage plus additional undercover parking, separate multipurpose CBS building, expansive outdoor porches and entertainment areas, German inspired indoor & outdoor fireplace, stand alone carport with car washing facilities, full home generator, home security system, advanced stereo system for interior & exterior of home. This custom designed concrete Residence consists of two buildings attached by large open covered breezeway. Enter into the foyer leading to a grand interior living and entertaining area offering views in every direction, all of which lead out to expansive wrap around porches. Custom gourmet kitchen with dual refrigerator, dual dishwashers, dual ranges, all Viking appliances, wet bar with wine cooler, & multiple sinks. Private office, walkin pantry, & guest bath. The sleeping quarters located in separate building offers private third floor master suite & bath with steam shower, jacuzzi tub, dual sinks, & a dream walkin closet. Two additional guests rooms, bathroom & living area on main level. Additional ground level cabana bar, plus private guest suite. This grand Estate home was completely rebuilt in 2006 and 2009 with two separate buildings attached by exceptional breezeway and all overlooking the beautiful gulf front waters. So much more...call for full details.

$12,000,000
Key Largo
Coral Coast Corrected Plat   - MM: 96.00
7 Bed, 7 Baths, 7,567 SqFt Days Listed: 94
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift220ft.

Magnificent custom built Bay Front mansion located in Coral Coast. A distinctive gated enclave of only 15 luxury estates. This marvelous Beachfront home is set in the natural beauty of native hardwood hammocks. The home enjoys the rare combination of a private pristine white sandy beach combined with the benefit of a 220-foot dock, multiple boat lifts, ample dockage, and 5 feet of depth. The satisfaction of owning this home, meticulously designed to provide the ultimate in comfort and luxury, goes far beyond the beauty of its surroundings.No expense was spared in Design, Construction, and Materials. State of the art construction techniques such as Post Tensioned concrete slabs, Brazilian Oak hardwood floors, long lasting 1000-gallon buried propane gas tank, high end Elite solid wood cabinetry, Classic elegant Crema Marfil marble on all interior & exterior ground floors, driveways, staircases, terraces, and an elevator serving all levels are just the beginning of a long list of special features too numerous to mention here.This property is strategically located just 40 minutes from the mainland for convenient access when arriving to or leaving from paradise. Beyond a retreat for personal relaxation, this Beachfront estate offers ample space for the entire family and guests. Watching the sunset, playing beach volleyball, Kayaking, paddle boarding, or hosting beachside barbecues at this exquisite home will be part of cherished memories with family and friends for years to come.

$13,895,000
Marathon
Seawatch   - MM: 53.50
5 Bed, 5 Baths, 4,187 SqFt Days Listed: 624
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip560ft.Rip R

If you are looking for a beautiful place to call home, your very own paradise awaits! Located in the heart of the Florida Keys, Marathon is a tranquil and serene place to live, surrounded by the crystal clear waters of the Gulf of Mexico. This modern beachfront property has it all. Its one of a kind, unique and breathtaking! Enjoy island living in this stunning 5 bedroom home with views from every room. Come experience the beauty of the Florida Keys and make Marathon your new home. If privacy is important to you, this is the home for you. Your private beach awaits along with a boat dock which has a 25,000 lbs boat lift attached, dock has room for a yacht and jet skis. Property also includes an additional boat slip within the Seawatch marina. Also enjoy entertaining at your very own tiki bar and custom outdoor kitchen. Want a drink but dont want to get out of the pool? No problem. Swim up to the pool bar and enjoy a refreshing drink while still soaking up the sun. Once youre here, you have no reason to leave!

$14,500,000
Marathon
Casa Manana Shores   - MM: 50.50
6 Bed, 6 Baths, 10,852 SqFt Days Listed: 148
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin,Boat Slip218ft

Casa Manana Shores, located in the heart of Marathon, is a developers dream or a private owners potential paradise. This secured gulf front estate offers 3.86 acres of land and is surrounded by an eight foot concrete wall with three gated entrances. The property boasts approximately 540 linear feet of Highway frontage and 695 linear feet of water frontage. It offers 218 feet of concrete seawall, including a cut-in protected boat slip. There is even room for a helicopter landing pad to be installed. This unique property is zoned mixed-use commercial and comes with one commercial transferable building right. It is currently a private residence with a separate garage and workshop. The 10,852 square foot mansion is solid concrete construction. It has ten bedrooms, six and a half bathrooms, a sauna, game room and great room. Repairs are needed, and the interior needs significant updating. An attached partially screened enclosure holds an impressive 12 ft deep swimming pool that measures 25 x 50 ft. The garage/workshop is a separate structure with two rooms with a mini split air conditioner. The existing structures could be demolished for those with a vision, leaving you with a 3.86 acre blank canvas in the center of town. Its versatile zoning designation offers multiple possibilities for residential and/or commercial use. Over the years it has previously housed a motel with a marina, a 19-unit trailer park, and a restaurant. This property presents the opportunity to create the ultimate secluded retreat of your dreams!

$16,990,000
Ocean Reef
Misc Ocean Reef Subdivisiond   - MM: 905.00
7 Bed, 7 Baths, 5,417 SqFt Days Listed: 110
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

With delivery targeted for mid 2025, your dream home is underway at one of the premier locations at the Ocean Reef Club. This 5,417 square foot home will offer direct western exposure on 100 ft. of water frontage with planned 50 T dock.Enjoy beautiful Key Largo sunsets in a private serene setting on Sunrise Cay from this beautifully-appointed, modern coastal home featuring a main house, guest casita and garage, including seven total bedrooms and seven and a half baths. The wide open living space delivers a contemporary, fully-loaded kitchen, great room and dining area. Outside the home, your Ocean Reef Club oasis includes a sundeck with a pool and hot tub overlooking the canal, as well as a complete outdoor kitchen.

$21,900,000
Summerland Key
Niles Channel Subdivision   - MM: 25.00
5 Bed, 5 Baths, 3,392 SqFt Days Listed: 138
Off Shore Isl - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin,Other Dockage,

Welcome to Howell Key! This unique island oasis, purchased in 2010, was developed as an off-grid, private family retreat for a multi-generational remote getaway. Now, this breathtaking 9.69-acre turnkey opportunity is on the market, inviting you to live your offshore island dream or invest in a one-of-a-kind vacation rental experience. Situated off mile marker 25 in Summerland Key, Florida Keys, Howell Key is just a 5-minute boat ride from your private masterpiece. With direct access to both the Atlantic Ocean and the Gulf of Mexico, your watersport dreams can come true daily. Proximity by boat is close to Looe Key National Marine Sanctuary, many sand bars, and the famous 5-star Little Palm Island Resort and Spa. This inviting island sanctuary features dockage accommodating vessels up to 50 feet and an electric gate leading to the marina lagoon. The energy-efficient, immaculate five-bedroom, four-bath home boasts a saltwater pool, exposed beam ceilings, travertine tile throughout, and SIPS panel technology construction. Additional structures on Howell Key include a guest house, garage, animal pens, pickleball court, tiki hut with beach, helipad, and finger dock with a covered sitting area. Plus, a second ROGO-exempt permit allows for constructing another dream home. This is a completely turnkey, fully furnished property that provides a peaceful, tropical escape from the ordinary. This purchase includes a Shore Station Lot completely fenced in to leave vehicles and has a 58 seawall to accommodate your personal ferry. Full list of amenities included in the documents tab.

$25,000,000
Upper Matecumbe Key Islamorada
Russell Estates   - MM: 82.80
7 Bed, 7 Baths, 8,288 SqFt Days Listed: 336
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin,Boat Slip,Boat

SERENITY CAY is an unparalleled and extraordinary estate nestled in the heart of Islamorada. This exclusive 3.37-acre compound offers utmost privacy with its gated and fenced entrance. As you enter the property, a picturesque driveway winds through lush tropical landscaping, setting the stage for the opulence that awaits. The gardens host raised beds, lemon, lime and avocado trees, banyan and native trees and a coral rock stone fire circle. The main house, spanning an impressive 6,935 sq. ft. (5B/6.5B), and the charming 1,353 sq. ft. cottage (2B/2B) both exude elegance and sophistication. Expansive shaded verandas extend from both residences, providing a seamless transition between indoor and outdoor living and providing expansive lounging enjoyment around the private, heated and chilled infinity edge pool and spa. With a total of 6,830 sq. ft. of shaded decking adorned with exquisite travertine stone flooring, youll have ample space to relax and entertain while enjoying the breathtaking views. Situated on the Florida Bay, this tropical retreat boasts an array of exceptional features. Two protected boat basins, complete with jetties, a waterfall, boat ramp, and a boat lift in the second protected boat basin, ensure that your boating desires are met. The 230 of water frontage on the bay allows for unforgettable sunsets and rare, but easy access to the oceanside, just one mile away. Additionally, the property extends 150 into the Florida Bay, further enhancing its value. The main residence is truly grand, featuring 5 luxurious ensuites, including 2 master suites and a bunk room with 6 bunks, each with its own expansive balcony. With 7 full baths, 1 air-conditioned pool bath, and 1 half bath, every convenience is catered to. The house also boasts 5 surround-sound media rooms, including a soundproof office/critical listening room. Attached 2-car garage, workshop and a 2,500 sq. ft. full boat house, which can also accommodate 2 cars or 1 car and 1 boat on a trailer.

$25,000,000
Key Largo
Unplatted Lower K.l.   - MM: 92.00
8 Bed, 8 Baths, 8,949 SqFt Days Listed: 268
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Boat

Experience Absolute Paradise! A Legacy Florida Keys Estate offering ultimate privacy & tranquility. The Orchid Cove Estate spans 14.5 Acres offering 1,000 ft. of waterfront & Private Beaches accessed through a grand entrance surrounded by a breathtaking canopy of exotic trees. Award winning Botanical gardens surround the property featuring impeccably curated nature trails leading to the main house, a boathouse, guest villas, & beach cove. Main residence rises 10 ft above the ground level, entered through a footbridge surrounded by coral rock waterfalls & koi ponds. Expansive water views, Library, Theater, Spa & Wellness room, Elevator & Chefs kitchen, private boat dockage,10+ car garage, catering facilities, generator & more. Daily spectacular sunsets. Arrive by seaplane, boat, or car.

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 11-26-2024.
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