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

Total Listings 280
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$6,500,000
Plantation Key
Sunshine Estates   - MM: 90.50
3 Bed, 3 Baths, 2,459 SqFt Days Listed: 221
-5.80% ($400,000) 1 Price Change : Last Change 71 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Ramp1

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.

$6,750,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
6 Bed, 6 Baths, 5,100 SqFt Days Listed: 10
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 100ft.Concrete

Introducing 194 Buttonwood Lane, a rare waterfront sanctuary nestled in the prestigious Safety Harbor enclave. This meticulously designed 6-bedroom, 7-bathroom residence seamlessly blends architectural elegance with modern comfort. The heart of the home features a chefs kitchen outfitted with top-of-the-line appliances, custom cabinetry, and breathtaking stone finishes on the countertops and backsplash. A thoughtfully placed custom steam shower adds a spa-like element to the homes exceptional amenities. This home is perfect for everyday living and elevated entertaining. Expansive living spaces flow effortlessly to the outdoors, where covered lounge areas, low-maintenance artificial turf, and tropical landscaping create the ultimate indoor-outdoor lifestyle. A full laundry room and spacious garage add practicality to the propertys thoughtful design. Boating enthusiasts will appreciate 100 feet of prime dockage plus an additional 20 feet of canal frontage, offering unmatched access and flexibility for multiple watercraft. A true statement of coastal luxury--this is Florida living at its finest.

$6,950,000
Big Pine Key
Port Pine Heights   - MM: 29.00
3 Bed, 3 Baths, 4,687 SqFt Days Listed: 10
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Basin,Boat

Breathe in serenity during your escape to the The Castle, a luxurious gated Gulf-front estate gracefully spanning 1.14 acres on Big Pine Key. This extraordinary retreat is a rare blend of architectural grandeur and coastal charm, thoughtfully designed for both relaxation and recreation. Boaters will delight in an unparalleled offering of 235 feet of dockage total: 140 feet of protected canal-front dockage featuring a 15,000 lb lift, cut-in slip, boat ramp, PLUS a 95-foot open water pier-style dock with additional 15,000 lb lift and cut-in slip - set against a 130-foot concrete seawall for secure, convenient access. Crafted in 2014 with solid poured concrete, impact-rated windows and doors, whole home generator and elevator, the home is built for enduring elegance. With over 4,600 square feet of refined interior space, this 3-bedroom, 3-bathroom estate is an architects masterpiece with its stately presence, curved openings, and striking double staircase. Step inside to a breathtaking panorama of endless open Gulf waters and nightly sunset performances. The chefs kitchen is a dream for entertaining, featuring 10.5-foot island with seating for 8, dual sinks, refrigerators, and ovens, plus Jenn-Air 6-burner gas cooktop with pot filler, and rich wood cabinetry. Enjoy the grand family room with Gulf views, host movie nights in the private theater, or dine al-fresco under the stars. Nearby, find the full-size laundry room and storage. The top-floor primary suite is a sanctuary, offering sweeping water views, home office, private lounge with kitchenette, spa-like bath with clawfoot tub, tiled shower and generous walk-in closet with additional laundry. Outside, the resort-style pool beckons with a spa, water features, LED lighting, plus heater and chiller. Rooftop deck with 180-degree views, and unrivaled sunsets await. Offered fully furnished, including a 2023 Sea Cat, 14.5 skiff, and 2015 Chevrolet Silverado - this is ultimate Keys living without compromise!

$6,995,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 5,195 SqFt Days Listed: 26
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Slip,Boa

Experience the pinnacle of luxury waterfront living in this extraordinary custom contemporary estate, ideally positioned in the heart of Islamoradas premier community of Venetian Shores. Newly constructed, the residence radiates modern coastal elegance and features impeccable attention to detail. A total of five spacious bedrooms and five en-suite bathrooms are thoughtfully laid out, complemented by a half bath and separate cabana-style guest quarters, creating an ideal retreat for family and visitors.Located on the bayside, the estate offers 100 feet of deep-water dockage, complete with a cut-in boat slip, 2 boat lifts & a float-on double jet ski lift. With direct access to the Gulf and Atlantic through world-famous Snake Creek, the location is a dream for avid boaters and luxury seekers.Inside, soaring tray ceilings, marble tiled floors, a private elevator, and a grand staircase elevate the living experience. The open-concept layout seamlessly connects the kitchen, dining, and living areas for effortless flow. The chefs kitchen features premium appliances including a Dacor gas cooktop, a walk-in pantry w/custom shelving, a prep island, and an expansive bar-height island for gathering. A private, elevated two-story guest wing includes a spacious bedroom & bath, as well as a billiard/game room w/full bath. The third-floor owners suite offers a sanctuary, highlighted by dual walk-in closets, a circular soaking tub, oversized shower, and separate water closet. Finally, there is a 3 car garage for all your cars & water toys.Outdoor living is just as impressive with multiple balconies overlooking tropical landscaping & wide canal. A heated pool/spa anchors the expansive outdoor area with outdoor kitchen, covered dining & lounging areas, a fire pit, hammock, sandy yard, palms, plume grass & lemon trees. This estate is a rare offering that perfectly blends refined style, tropical comfort, and unparalleled boating access, the very essence of luxury Keys living.

$7,900,000
Key Largo
Sunrise Point   - MM: 95.00
10 Bed, 10 Baths, 5,392 SqFt Days Listed: 72
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Other Dock

This unique property combines privacy, comfort, and the beauty of coastal living. With ample space for gatherings and adventures on the bay, youll fall in love with the charm and tranquility of this magnificent bayfront estate. 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. Dont miss the opportunity to own this slice of paradise! Contact us today to schedule your private tour and experience the magic of this beautiful bayfront property.

$7,999,000
Key Largo
Buccaneer Point   - MM: 98.00
6 Bed, 6 Baths, 4,592 SqFt Days Listed: 70
-11.11% ($1,000,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Nestled in the heart of Key Largo at Mile Marker 98, this luxurious modern estate offers 4,592 square feet of impeccably designed living space, featuring 6 bedrooms and 5.5 bathrooms. With stunning architectural elements and sweeping bay views, this home is a masterpiece of indoor-outdoor living and elevated coastal design.Step inside to soaring ceilings, a striking spiral staircase, and floor-to-ceiling windows that flood the space with natural light. A private elevator provides effortless access to all levels of the home, adding both convenience and sophistication. The open-concept layout is anchored by a chefs kitchen, fully outfitted with premium Miele appliances, sleek porcelain countertops, and custom Italian cabinetry--designed for both beauty and functionality. The main living area seamlessly opens to the outdoors through 20-foot bi-fold accordion doors, blurring the line between inside and out.Sophisticated technology enhances everyday living, including a state-of-the-art KEF sound system and a full IP smart camera system for security and convenience.The primary suite is a private retreat with panoramic bay views, a morning bar, and an expansive Italian-designed walk-in closet. The ensuite bathroom rivals a luxury spa, featuring a soaking tub, dual rainfall shower system, and premium finishes imported from Spain.Outdoor living reaches new heights with multiple curated spaces: a fully turfed rooftop terrace with ocean views, a main-level saltwater pool with an oversized spa, and a third-floor alfresco kitchen complete with a wet bar--ideal for entertaining. The property also includes a private golf putting green and a custom dock equipped with a 20,000-pound boat lift and room for additional watercraft.Every inch of this residence has been thoughtfully crafted to maximize its breathtaking waterfront location while delivering an unparalleled lifestyle of comfort, elegance, and leisure.

$7,999,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
6 Bed, 6 Baths, 4,394 SqFt Days Listed: 102
-11.11% ($1,000,000) 1 Price Change : Last Change 2 Days Ago
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+/- ft. 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 custom 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 a 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 creating a wow factor throughout the stunning home.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!

$8,499,000
Marathon
Crains Subdivision   - MM: 58.00
4 Bed, 4 Baths, 5,168 SqFt Days Listed: 101
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.

$9,650,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
6 Bed, 6 Baths, 6,866 SqFt Days Listed: 328
-10.23% ($1,100,000) 3 Price Changes : Last Change 2 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.

$9,985,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
8 Bed, 8 Baths, 5,392 SqFt Days Listed: 125
-8.39% ($915,000) 2 Price Changes : Last Change 2 Days Ago
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

$10,400,000
Key Largo
Coral Coast Corrected Plat   - MM: 96.00
5 Bed, 5 Baths, 6,083 SqFt Days Listed: 157
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
Mat Sandy Beach   - MM: 75.00
4 Bed, 4 Baths, 4,512 SqFt Days Listed: 152
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!

$12,499,000
Key Largo
Buccaneer Point   - MM: 98.00
4 Bed, 4 Baths, 5,100 SqFt Days Listed: 105
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 100ft.

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, creating an inviting and sophisticated ambiance. Designed and fully furnished by Steven G. Interiors spanning over 9,000 sq. ft. of indoor and outdoor living space. This estate offering has four ensuite king bedrooms, including separate guest quarters, five bathrooms, three half baths and 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 butlers pantry, and a pass-through to the outdoor bar area. 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: 349
-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!

$12,900,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
6 Bed, 6 Baths, 4,394 SqFt Days Listed: 168
-13.42% ($2,000,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift220ft.

Welcome to BAYVIEW HIDEAWAY a generously sized, COMPLETELY RENOVATED home with top-tier finishes showcasing stunning Florida bay views of calm waters and vibrant nightly sunsets, combining tropical charm with modern luxury--ideal for those in search of a tranquil getaway in an unforgettable PRIVATE setting. Situated on TWO SEPARATE LOTS-each with its own parcel ID--the buildable bayfront lot has endless potential. The price per square foot reflects this extraordinary opportunity. The property features 220+/- FT. OF CONCRETE DOCK, an additional 200+/-ft. of water frontage, THREE BOAT LIFTS, helicopter access, a NEW PRIVATE POOL, and SIX BEDROOMS EACH WITH WATER VIEWS. Ideally located in Islamorada just north of the Channel 5 Bridge with its 65 clearance and 30 minutes from Marathon executive airport, it offers nearly IMMEDIATE ACCESS to the ocean or Intracoastal Waterway, world-class offshore and backcountry fishing, reef diving, and an array of nearby attractions, outdoor activities, and dining--striking a perfect balance of seclusion and accessibility ideal for any boater, angler or water enthusiast!

$15,990,000
Ocean Reef
Misc Ocean Reef Subdivisiond   - MM: 905.00
8 Bed, 8 Baths, 5,417 SqFt Days Listed: 311
-5.89% ($1,000,000) 1 Price Change : Last Change 2 Days Ago
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

$22,500,000
Key Largo
Unplatted Lower K.l.   - MM: 92.00
8 Bed, 8 Baths, 8,949 SqFt Days Listed: 469
-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: 150
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.

$31,200,000
Lower Matecumbe
Misc Lower Matacumbe   - MM: 76.00
8 Bed, 8 Baths, 10,228 SqFt Days Listed: 15
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Ramp1

Spectacular 1.65-Acre Bayfront Estate in Islamorada, Florida Keys |
8 Bedrooms | 9.5 Bathrooms | 10,228 Total Sq Ft | 150 Waterfront | Dockage | Pool | BeachWelcome to a rare offering in the heart of the Florida Keys--this 1.65-acre gated bayfront compound in Islamorada combines timeless island luxury with modern amenities and endless water views. With 150 feet of private waterfront, dockage, boat ramp, private beach, two pools, and lush, mature tropical landscaping, this estate is a true Keys sanctuary.The 7,562 sq ft main residence boasts 5 spacious bedrooms, 5.5 bathrooms, an office, and exquisite finishes throughout. The gourmet kitchen features marble and dolomite countertops, a custom mosaic tile backsplash, built-in Miele coffee system, wine dispenser, 36 Wolf gas cooktop, four Sub-Zero refrigerators, and two laundry rooms. A stunning 180-bottle glass wine cellar, handmade wood bar with wood sink, Sonos sound system, and living room with blackout shades to enhance the entertaining potential.Additional highlights include an elevator, Lutron lighting system, Toto toilets, expansive covered porches with panoramic open bay views, an outdoor kitchen complete with Italian brick pizza oven, Evo flat grill, and smoker, as well as a tackle room and 4-car garage.The 2,666 sq ft guest house offers a private gated drive, 3 bedrooms, 4 bathrooms, a private pool, and a fully equipped kitchen with JennAir appliances, making it ideal for hosting guests or extended family in complete privacy.With two gated driveways, serene lawns, and a high-end tropical ambiance, this estate seamlessly blends privacy, prestige, and paradise.A one-of-a-kind legacy property - experience the ultimate Florida Keys lifestyle.

$35,000,000
Marathon
Crains Subdivision   - MM: 58.00
9 Bed, 9 Baths, 9,530 SqFt Days Listed: 110
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 06-15-2025.
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