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

Total Listings 260
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$6,895,000
Key West
Sunset Key   - MM: 0.00
4 Bed, 4 Baths, 2,558 SqFt Days Listed: 105
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Experience unparalleled island living on Sunset Key, an exclusive island community located in the heart of Key West Harbor. Accessible 24 hours a day via a dedicated island ferry, this extraordinary home offers the ultimate blend of privacy, luxury, and convenience. All this just a four minute boat ride from the vibrant streets of Key West.This bright and airy 4-bedroom residence is designed to capture breathtaking open ocean views. Large windows bathe the home in natural light, creating an inviting and serene atmosphere. The heart of the home is a fabulous chefs kitchen equipped with top-of-the-line appliances, perfect for creating culinary masterpieces while taking in the views of the sparkling water.Step outside to your beach-front oasis, where you can unwind and enjoy the gentle sea breeze or take in a spectacular sunset over the Gulf of Mexico. On the island, a wealth of world-class amenities awaits, including a gourmet restaurant, a rejuvenating spa, tennis courts, and more, ensuring your every need is met in this tropical paradise.With unparalleled luxury, exceptional views, and exclusive island living, this property offers the perfect retreat in one of the most sought-after destinations in the world.

$6,900,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
3 Bed, 3 Baths, 3,019 SqFt Days Listed: 111
-7.94% ($595,000) 1 Price Change : Last Change 30 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift100ft.

Built in 2014, Bahia Bonita is an ultra-private bayfront estate in the heart of downtown Islamorada designed to offer the ultimate combination of location, deep-water dockage, storm resiliency and open water views from every room. If you have been wishing for an exceptional piece of Florida Keys paradise where natural beauty and luxury living meet modern, solid concrete construction, this thoughtfully designed home may exceed your expectations. Begin your day by stepping out of your primary suite to your bayfront terrace and into a second floor Infinity Edge pool. In the evening, slide open the wall of glass on the top floor to experience the brilliance of Islamoradas sunsets from your great room, gourmet kitchen or outdoor decks. Feel like grilling? Just one step away is an outdoor kitchen with adjacent bay view dining. For stargazing, venture up the spiral stairs to the rooftop deck for a breathtaking front row seat. Built to withstand sustained 200 mph winds, this home also includes accordion shutters over impact glass for the ultimate defense. Outside, enjoy 250+ linear feet of open water frontage and a 100 dock with two boat lifts fitted with hurricane and storm surge protection. This unparalleled storm resiliency is combined with modern sustainability features including a large cistern with state-of-the-art water purification system, a grid-tied solar array and integrated batteries eliminating the need for a generator. Other functional luxuries include an elevator, professional camera/security system, central wet-dry vacuum system, mature landscaping and an enormous three-car, 2,200 sf garage, complete with workshop and storage. This home also boasts marble floors throughout and a spectacular floating staircase. Plus, a fourth bedroom and bathroom can be easily added without modifying the structure or footprint at minimal expense. All within walking distance of Islamoradas favorite dining spots. Call today!

$6,950,000
Shark Key
Shark Key   - MM: 11.00
5 Bed, 5 Baths, 3,875 SqFt Days Listed: 75
-0.71% ($50,000) 1 Price Change : Last Change 11 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Step into Luxury Living at Its Finest..Welcome to this magnificent custom-built home nestled within the prestigious gated community of Shark Key, one of the Florida Keys most coveted waterfront enclaves. Offering unparalleled security with 24-hour surveillance, Shark Key provides a serene and secure haven for discerning homeowners.This elegant residence spans 3,875 square feet of meticulously crafted living space and features five bedrooms and three & half baths that exude sophistication and style at every turn. Experience a bright, open floor plan adorned with exquisite finishes and architectural details, seamlessly blending indoor and outdoor living.Automated window treatments and a Euro-Wall that folds inviting the outdoors in, transforming the spacious living area into an extension of the lush outdoor oasis. The covered lanai is an entertainers dream, showcasing a luxurious heated infinity pool and spa with a waterfall, all overlooking the breathtaking blue waters of the Gulf of Mexico.The gourmet kitchen is a culinary masterpiece, equipped with top-of-the-line Wolf and Miele appliances. A large island with seating for four serves as the centerpiece, perfect for hosting family and friends. Adjacent to the kitchen, the dining area offers stunning open water views, while the nearby bar room features a wine EuroCave, ice drawer & refrigerator drawer, and convenient access to the lanai and pool area.Primary Suite Retreat..
Escape to the second-floor with two master suites the primary master suite, a private sanctuary with a spa-like ensuite bath, expansive walk-in closet, and a tranquil sitting area ideal for watching sunsets over the Gulf. The thoughtfully placed laundry room is conveniently nearby.Additional Features
..This home also includes parking beneath the residence and ample storage space, ensuring both functionality and convenience. Elevator to three floors.

$7,164,000
Marathon
Woodburns Subdivision   - MM: 49.50
4 Bed, 4 Baths, 3,212 SqFt Days Listed: 37
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage92ft.

Two Waterfront Homes on Four Open Water Gulf-Front Lots - A Rare Opportunity1401 51st St & 1235 51st Gulf St, Marathon, FL 33050, are being sold together as a unique waterfront compound offering breathtaking open water views, privacy, and endless possibilities. This package includes two stilted homes totaling four bedrooms, four bathrooms, and a guest suite and more, along with a newly built three-bay garage featuring two hydraulic car lifts and a 42-foot-long bay within a 1,211 sq. ft. concrete bunker constructed in 2015.Situated on over 55,000 square feet of uplands, the property provides ample space for a private estate, rental investment, or development opportunity. It is not on SFA, and building rights are available for purchase if expansion is desired. A deep-water dock is already in place, with approximately 575 feet of shoreline offering additional dockage potential.This gated and fully fenced compound is surrounded by lush, mature tropical landscaping, creating an unparalleled sense of seclusion. Motorized drive-through gates on both ends provide access to a beautifully maintained property featuring meandering pathways, a coral-cut shoreline, and a firepit at the waters edge. Two small uninhabited islands just offshore add to the unique charm of this exceptional retreat.Located in the heart of Marathon, this property combines privacy, convenience, and direct boating access. Whether you are looking for a private family compound, an income-producing investment, or a coastal sanctuary, this offering is truly one of a kind. See properties listed separately in mls#613880 and mls#613879

$8,300,000
Key Largo
Sunrise Point   - MM: 95.00
10 Bed, 10 Baths, 5,392 SqFt Days Listed: 254
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.

$8,499,000
Marathon
Crains Subdivision   - MM: 58.00
4 Bed, 4 Baths, 5,168 SqFt Days Listed: 27
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin

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.

$8,999,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
6 Bed, 6 Baths, 4,394 SqFt Days Listed: 28
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift220ft.

Youre not just buying a home--youre embracing an unparalleled waterfront lifestyle! This exquisite six-bedroom, four-bathroom residence, featuring two primary suites, is situated on a highly sought-after corner lot with breathtaking water views from every room. Boating enthusiasts will love the 220+/- feet of concrete dock, offering ample space to park yachts and welcome guests arriving by boat, complete with three boat lifts for ultimate convenience.Completely gut-renovated down to the studs in 2020, this home feels brand new, boasting a cool, neutral color palette that mirrors the surrounding turquoise waters while maintaining a warm and inviting ambiance. Owners have meticulously kept the property in pristine condition. A local realtor recently said it was the cleanest house shes been in in decades! Energy efficiency and low maintenance further accentuates effortless luxury living.Step outside to enjoy a custom saltwater pool, built in 2021, featuring both a heater and chiller for year-round relaxation. With direct Bay-to-Ocean access via Channel 5 Bridge, this location is a dream for boaters. Inside, Viking appliances and countless upgrades and custom touches elevate this homes elegance and functionality.Opportunities like this are rare in the Florida Keys. Start living the dream in the most desirable area in the Florida Keys! Dont wait - schedule a showing today!

$9,950,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
6 Bed, 6 Baths, 6,866 SqFt Days Listed: 254
-7.44% ($800,000) 2 Price Changes : Last Change 19 Days Ago
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.

$10,400,000
Key Largo
Coral Coast Corrected Plat   - MM: 96.00
5 Bed, 5 Baths, 6,083 SqFt Days Listed: 83
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift200ft.

The Ultimate Bayfront OasisStep into a world of timeless sophistication and coastal warmth with this commanding, yet inviting, custom-built Bayfront Estate. This remarkable 5-bedroom, 6-full-bath, and 2-half-bath home spans over 6,000 square feet of meticulously designed living space across three levels. Nestled within the exclusive, gated community of Coral Coast--home to only 15 private estates--this residence offers unmatched privacy and breathtaking views of Florida Bay and the Everglades National Park. As you enter, youre immediately greeted by stunning vistas of the Bay and the warmth of Brazilian walnut hardwood floors, complemented by the grandeur of soaring ceilings in the great room. Culinary enthusiasts will delight in the spacious gourmet kitchen, thoughtfully designed with Monogram appliances, a gas stove, a Mystic River sink, and an oversized island perfect for gathering. Ample cabinetry, a breakfast bar, and a cozy nook overlooking the Bay complete this dream space. Exceptional layout for luxurious Upper Keys living; The main level features two spacious bedrooms with en-suite baths, as well as a Bay-facing office/den with a private bath, easily convertible into another bedroom. This level also includes a walk-in laundry room and a half bath for added convenience. Ascend the grand staircase to the top floor, or take the elevator that services all three levels. The third floor houses the Owners suite, which spans an entire wing of the home. This sanctuary boasts a spa-like bathroom with double vanities, a jet tub offering sweeping Bay views, and a private balcony. A third guest bedroom with an en-suite bath completes this level. On the ground floor, discover a guest suite with a private living area and kitchenette--perfect for self-contained accommodations. This level also features a large family recreation room with a fireplace and a full bar, plus a second walk-in laundry room to complement the one on the main floor.

$10,900,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
8 Bed, 8 Baths, 5,392 SqFt Days Listed: 51
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat LiftConcrete

Nestled in the exclusive Safety Harbor enclave of Islamorada, this stunning Gulfside estate offers an unparalleled blend of luxury and tranquility. Situated on a prime point, the property boasts breathtaking open water views and the added advantage of protected dockage, making it a boaters paradise. With a concrete seawall, two boat lifts equipped with power and water, and a fish cleaning station, this home is perfectly appointed for waterfront living. Easy ocean access through the nearby Channel 5 Bridge adds to its appeal for avid anglers and adventure seekers alike. Inside, the home features eight spacious bedrooms, each with its own ensuite bath, plus two additional half baths for convenience. The master suite is a private sanctuary with a spa-inspired bath, while the open layout showcases spectacular water views through impact windows and sliding glass doors. An elevator ensures effortless access to all levels, and the wraparound balcony invites you to savor unobstructed panoramas. The gourmet kitchen, complete with high-end stainless steel appliances and gas cooktop, is a chefs delight, complemented by an outdoor kitchen for alfresco entertaining. With its seamless indoor-outdoor design and unmatched location, this property is the epitome of luxurious Keys living. Owner/Agent

$10,900,000
Lower Matecumbe
Mat Sandy Beach   - MM: 75.00
4 Bed, 4 Baths, 4,512 SqFt Days Listed: 78
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Slip,

Discover the unparalleled beauty and tranquility of this Bayfront Estate, nestled on the pristine shores of Lower Matecumbe in the Florida Keys. Surrounded by lush, meticulously landscaped grounds, this exceptional property offers direct waterfront on the crystal clear waters of the Gulf. Experience breathtaking sunsets over the horizon, world-class tarpon fishing just steps away, and private dockage with ample space for multiple boats.Unwind in the stunning infinity pool, blending seamlessly with the serene surroundings. This is a rare opportunity where every moment feels like a dream!Developed with two buildings, splitting the living between the two making this unique design quite special. Embrace this exciting design or modify and create your own design. Blending the two buildings brings all living together. Other treasures of this estate property include a 2 car garage, separate guest suite, expansive indoor outdoor entertaining overlooking the bay, separate concrete building for versatile use, boat lift, boat ramp, German inspired fireplace, electric gate, sprawling green space, and so much more.Owner is ready to sell. What an opportunity!

$11,975,000
Key Largo
Coral Coast Corrected Plat   - MM: 96.00
7 Bed, 7 Baths, 7,567 SqFt Days Listed: 221
-0.21% ($25,000) 1 Price Change : Last Change 2 Days Ago
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.

$12,499,000
Key Largo
Buccaneer Point   - MM: 98.00
4 Bed, 4 Baths, 5,100 SqFt Days Listed: 31
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Defined by its architectural prowess and unique style, this home stands as a rare and exceptional creation, unlike anything else in the Florida Keys. Ascending the staircase flanking a grand pivot door, you enter a sheltered vestibule offering sweeping views of the Florida Bay, bridging indoor and outdoor living. Every detail, from form to function, has been meticulously crafted to provide both visual drama and refined comfort. The thoughtful design fosters a seamless transition from the grandeur of nature to the luxury of the interior. Bali-inspired architecture combines warm, earthy tones, natural stone, and the finest finishes, creating an inviting and sophisticated ambiance. Designed and fully furnished by Steven G. Interiors and spanning 5,100 square feet, the estate offers four bedrooms, including separate guest quarters, five bathrooms, and a bonus room ideal for a private office or gym. The additional 5,000 square feet of ground-level space offers endless potential for customization. Floor-to-ceiling windows flood the interior with natural light, enhancing the open-concept designed for both private moments and grand entertaining. The gourmet kitchen features Wolf and SubZero appliances, double-drawer refrigerators, a striking waterfall island with Taj Mahal quartz, a butlers pantry, and a pass-through to the outdoor kitchen and bar. Two-toned cabinetry with a bronze finish complements the modern elegance throughout the home. A custom wine storage feature wall adds a luxurious touch, while recessed built-ins enhance bedroom spaces. The primary suite features a steam shower with surround sound, heated Toto toilets, separate vanities and closets, and a disappearing TV lift. Located in the Buccaneer Point Estates, this property offers deepwater dockage, ideal for boating and fishing. This home is a statement of refined living, blending unparalleled craftsmanship, cutting-edge technology, and a seamless connection to nature where elegance and luxury converge.

$12,500,000
Marathon
Casa Manana Shores   - MM: 50.50
6 Bed, 6 Baths, 10,852 SqFt Days Listed: 275
-13.79% ($2,000,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip,Basin218ft

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!

$13,400,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
6 Bed, 6 Baths, 4,394 SqFt Days Listed: 94
-10.07% ($1,500,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift220ft.

Welcome to BAYVIEW HIDEAWAY. Situated on 2 SEPARATE LOTS --each with its own parcel ID--the buildable bayfront lot has endless potential. The price per square foot reflects this extraordinary opportunity.This mini estate is surrounded by water on three sides with 435+/- water-frontage and secured by a 6-foot gated entrance. BAYVIEW HIDEAWAY boasts 220+ of concrete dock, complete with three lifts, power, and water. Ideal for boating enthusiasts, the canal accommodates yachts over 80+ feet and offers convenient access to Channel 5 Bridge with 65-foot clearance for seamless bay-to-ocean access. The second lot even has the potential for a helicopter landing.Meticulously renovated by the original builder in 2020-2021, this home was stripped to the bare framework and reimagined with modern updates, including new electric, plumbing, and impact-rated PGT/WinDoor windows and doors, porcelain tile flooring and Level 5 drywall throughout. The property features smart, energy-efficient upgrades, such as 4 Trane AC units with variable-speed smart thermostats, two water heaters, and foam-filled block insulation. Inside, the home offers picturesque water views from every room and features luxurious details, including Turkish marble stairs, vaulted ceilings, Hunter Douglas window treatments, and Italian marble accents in the primary baths. The spacious layout includes six bedrooms, each with private balconies, two primary suites, 4 bathrooms, and a chefs kitchen with Viking appliances, custom cabinetry, and Vetrazzo countertops.The outdoor spaces feature a new saltwater pool built in 2021 with a heater/chiller surrounded by marble pavers, a bar, BBQ area, a gazebo, an orchid house, pergolas, a putting green, and hot tub.Located in Safety Harbor subdivision in Islamorada--BAYVIEW HIDEAWAY is more than just a home; its a lifestyle opportunity. Combining high-end finishes, unparalleled amenities, and a prime bayfront location, this estate is a true gem in the Keys.

$16,990,000
Ocean Reef
Misc Ocean Reef Subdivisiond   - MM: 905.00
8 Bed, 8 Baths, 5,417 SqFt Days Listed: 237
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

A Rare Opportunity to Own One of Ocean Reefs Finest EstatesSet on one of the largest and most prestigious lots in Ocean Reef Club, this newly constructed waterfront masterpiece is designed to be a legacy estate--a home to be cherished by generations to come. With 8 bedrooms, 7.5 baths, a private guest casita, and a full elevator system, this is a resort-style sanctuary that balances elegance, comfort, and enduring quality. Move in this summer and experience unobstructed long Ocean Reef sunset views from this exceptional Sunrise Cay residence.Unparalleled Design & Versatility:-5,417 SF of Interior Space + 1,633 SF of Outdoor Living-Main House: 4,657 SF | Casita: 760 SF (2 Beds, 1 Bath, Living Room, Full Laundry)-Two Expansive Primary Suites (One on Each Level)-Flexible Spaces: 8 bedrooms can sleep 14 guests, or be transformed into home offices, a fitness studio, or media lounge-Second-Floor Coffee Bar & Dual Laundry RoomsResort-Style Outdoor Living:-100 of Direct Waterfront with a 50 Private T-Dock-632 SF Pool + 63 SF Spa with a cabana bath-Outdoor Gas Fireplace, Wolf Outdoor Kitchen, and Al Fresco Dining-Lush Mature Landscaping for Privacy & TranquilityWorld-Class Chefs Kitchen:-72 LaCanche French Range & Sub-Zero Refrigeration-Custom Mouser Cabinetry & Dual Kitchen Islands-Quartz Countertops & Wolf Stainless Steel Outdoor KitchenBuilt for Longevity, Security & Comfort:-774 SF Garage + Motor Court for Multiple Vehicles & Golf Cart Parking-Impact-Resistant Sliding Glass Doors & Windows-Two-Story Concrete Shell Construction + Metal RoofThe Best of Ocean Reef ClubLocated in the exclusive Sunrise Cay neighborhood, this private waterfront sanctuary offers rare unobstructed sunset views, direct boating access, and is just moments from the clubs championship golf courses, private airstrip, marina, and elite dining.This rare opportunity to own a generational Ocean Reef estate wont last

$21,900,000
Summerland Key
Niles Channel Subdivision   - MM: 25.00
5 Bed, 5 Baths, 3,392 SqFt Days Listed: 265
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.

$22,500,000
Key Largo
Unplatted Lower K.l.   - MM: 92.00
8 Bed, 8 Baths, 8,949 SqFt Days Listed: 395
-10.00% ($2,500,000) 1 Price Change : Last Change 63 Days Ago
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.

$25,000,000
Upper Matecumbe Key Islamorada
Russell Estates   - MM: 83.20
7 Bed, 7 Baths, 6,935 SqFt Days Listed: 76
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Basin,Boat

Welcome to Serenity Cay, an exquisite Balinese-inspired estate where tranquility and luxury meet the endless beauty on the Florida Bay. A true masterpiece of engineering and design, this sprawling waterfront residence on nearly 4 acres offers an unparalleled blend of tropical elegance, sophisticated craftsmanship, and modern luxury. An expansive infinity-edge pool blends seamlessly into the sparkling waters of the bay while lush gardens create a serene oasis. The homes architecture showcases graceful, custom finishes and rich hardwoods, all hallmarks designs that evoke the spirit of the Islands. Spanning over 6,900 square feet, the interior is a seamless fusion of open-concept living spaces and private retreats. Soaring vaulted ceilings and vast windows invite abundant natural light and spectacular views of the bay, creating an indoor-outdoor flow. The primary suite serves as your personal sanctuary, complete with private terrace, spa-inspired bathroom, and walk-in closets fit for a connoisseur of fine living. Each guest has direct access to outdoor spaces and views. A bonus, versatile bunk room/media center sits just off the west wing of the home. The charming guest house is the perfect complement to the main home, nestled in its own secluded on site location this delightful addition exudes a warm, welcoming ambiance ideal for hosting guests, or as a private office or creative studio. This downtown Islamorada estate in an incomparable location; walking distance to shopping, dining, and local culture, also has appeal that extends to those with a passion for the great outdoors. Two protected docking basins and boat lift, sandy lounging beach, expansive outdoor lanai and outdoor kitchen offers the ideal space for entertaining or enjoying a quiet evening watching the sunset. Fly the seaplane in or land the helicopter. Premier boating access just moments away from the Intracoastal waterway and Ocean channels. Serenity Cay is not just a home, its an experience.

$35,000,000
Marathon
Crains Subdivision   - MM: 58.00
9 Bed, 9 Baths, 9,530 SqFt Days Listed: 36
Multi-Units - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Basin,Boat

Zephyr Cove; the extravagant aquatically inspired retreat that you deserve. Located on the breathtaking waterfront nestled along the Gulf and designed and built by DAsign Source. This stunning estate invites you to experience the perfect balance of luxury, tranquility, and adventure. With both fresh and saltwater elements woven into its design, every detail has been thoughtfully crafted. At the heart of the property lies a lazy river loop infinity pool, complete with bridges, swim-up pool bar in gazebo, spa with table, lap pool, beach-style entries, and waterfall grotto plus gas fire pit, putting green, and tropical gardens. From floating under the sun, entertaining guests, or enjoying a peaceful evening by the water, this home was manifested for unforgettable moments.Grand main residence vaunts an impressive private primary wing and elegant open spaces designed for comfort and entertainment. Indoor amenities include a temperature-controlled wine room, game room, home theater, fitness center, and conference room; endless ways to unwind and enjoy life. Two additional charming two-bedroom villas and a separate two-bedroom guest house are perched next door, perfect for hosting family and friends with style and privacy.Designed for the ultimate coastal lifestyle with outdoor kitchen and dining areas set against breathtaking Gulf views, ideal for entertaining or simply soaking in the beauty of your surroundings. Ample dockage and multiple boat lifts for your toys, located right between Vaca cut and Toms Harbor Cut for easy Ocean access. Expansive garages and storage spaces provide ample room for vehicles, boats, and all essentials. Whole-home 130kw generator in its own private structure, ensuring peace of mind no matter the season. This is where everyday life feels like youre being pampered at a lavish resort. Step into a world where the beauty of nature meets unparalleled craftsmanship and let the magic of the Gulf welcome you home. 15 min to private airport.

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 04-02-2025.
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