Upper Keys Waterfront Homes for Sale, Single Family Houses, Open Water, Ocean and Bay / Gulf Views

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.

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.

Aptly named The Sanctuary Islet, this rare, secluded peninsula is a hidden gem within a protected 25-acre private preserve of native trees and mangroves in scenic Key Largo-- the first island of the Florida Keys. Privacy is a key feature of this property, offering breathtaking views, lush tropical vegetation and daily visits from exotic birds. Enjoy year-round sunrises over the Atlantic from this truly unique retreat.Surrounded by pristine ocean yet walking distance to restaurants, bars, etc. this resort-like estate provides an experience comparable to a private island--but with all the conveniences of mainland living. Behind two private entry gates, this estate offers what is likely the most secluded and private setting in all of the Florida Keys.The 4,000 sq. ft. main home features 2,000 sq. ft. of balconies plus 4,000 sq. ft. of additional space downstairs. With four spacious bedrooms, including luxurious ensuite bathrooms, this home is designed for ultimate comfort and convenience. The indoor-outdoor tropical bathrooms add a touch of luxury, blending sophistication with nature. The seamless integration of indoor and outdoor living spaces immerses you in the lush surroundings, with ample space for al fresco dining, lounging, and entertaining.Pre-approved plans for a 3-bedroom, 3-bath guest house are included. As featured in The Wall Street Journals Global Mansions, this estate was designed by a world-renowned architect-engineer team and built to withstand direct-impact Category 5 storms.For boating enthusiasts, navigate your vessel into your own protected boat slip, accommodating a 45 boat on a 24,000-pound lift, with an expansive turning radius and direct access to a wide-open turning basin--no fairway maneuvers required.Whether you plan to make this your primary residence or an investment property, this turnkey home comes with a great management team in place. Opportunity to unite with an adjacent property, creating your won compound.

Garden Coves Southern Diversion is a peaceful and private North Key Largo escape, conveniently located right off John Pennekamp State Park and just a stones throw from Ocean Reef and quick ride to South Miami. Gorgeous open water view throughout the spacious home, plus over 350 of waterfront; excellent boating location just south of Jewfish Creek Bridge for fast Ocean to Bay access. Multiple nearby fishing and dining destinations make this property all the more desirable. Protected 30 and 70 docks on the inside canal for your island living toys. The home is being offered together with additional back lot and plans for guest home, both mixed use zoned parcels allow for wedding venue and vacation rentals or to host an abundance of events and guests. Current rental income available upon request.

Nestled in the panoramic setting of Islamorada, Florida, the brand new construction at 87895 Old Hwy offers a premium blend of luxury, privacy, and elegant island living. Sprawled over two acres on the azure Atlantic, this opulent abode stretches a massive 9,011 sq ft under air, extending to over 15,000 sq ft under roof. The expansive property includes five spacious bedrooms, five state-of-the-art baths, along with three additional half baths. The home features Thermador /Uline appliances including ice makers & upgraded eco-insulated commercial CGI windows and doors, an additional investment of $200k over the original allowance, that enhance the comfort and luxury of the interiors. Experience unmatched waterfront vistas with the houses 160 ft concrete jetty wrapped in a retaining wall and an 80 ft dock with electric and water facilities. Preserve your luxury vessels on the 20k 4 post elevator lift, adding convenience to lifestyle. The residence also includes an exercise room w/ possible conversion to 6th bedroom, theater room w/ possible conversion to 7th bedroom , office/den, & a laundry room on each level. An elevator ensures smooth movement across the floors. Indulge in outdoor living with the private pool, jacuzzi & around 1735 sqft of porches for lavish entertainment & serene lounging.The property comes protected by a concrete retention wall along the entire perimeter of the shoreline, ensuring complete tranquility. A private gated entrance exudes grandeur while providing security. This estate is zoned (Residential Estate), allowing the owner to apply for vacation rentals, if desired. Currently under construction, the property is perfect for those seeking a custom luxury experience. Enjoy a world-class island living experience in this architecturally significant estate filled with premium luxuries nestled right on the turquoise-blue waters of the Atlantic. Agents please check agent remarks

Welcome to 16 Seaside. This is your opportunity to have it all at your truly rare, ocean front, protected lagoon, new construction, Key Largo dream entertainment and relaxation haven. Imagine looking out past your outdoor pool and entertainment suite, across your private lagoon, past your tiki hut on your private beach to your view of the Atlantic Ocean. Outside you have 7 balconies, resort quality pool and covered entertainment oasis, private lagoon with parking for up to six boats each with their own shore power and water, private beach with tiki hut, privacy fences, automatic gate and approximately 2,500 square feet of covered parking. Inside you have all the amenities of a modern, newly constructed luxury home. You will have 6,585 square feet under air with state-of-the-art, comprehensive, fully integrated smart home which include full home lighting, climate control, audio and security, as well as outdoor control of the pool and outdoor lighting, multilevel entertainment options, stunning ocean views, 7 bedrooms with a primary on each floor, 7 full in-suite bathrooms, 2 half baths, multi floor laundry rooms, walk in and climate-controlled showpiece wine cellar, exquisitely appointed custom made kitchen, three level elevator, 4 zone cooling, and a whole home back-up generator. Located in Key Largo, this spectacular home is only an hour drive to Miami offering easy travel, big city entertainment and dining while allowing a quick escape back to the tranquility of your seaside oasis. Enjoy world class fishing and boating with room for all your friends, their boats and all the water toys. Suburban/commercial zoning is investor and 1031 exchange friendly. 16 Seaside is currently under construction and delivery is scheduled for end of April, 2025. Call today to make sure delivery is to you.***Note: This is a double lot with total lot size of 21,250 sq ft.

Experience the ultimate in luxury and design at this custom-built masterpiece on a private peninsula along the coveted Adams Cut Waterway. This 4-bedroom, 7-bathroom estate spans 4,000 square feet and offers breathtaking open water views, unmatched privacy, and world-class amenities. From the triple-poured concrete roof to La Finesta impact windows, every detail of this fortress is built to the highest standards. Enter through the curved travertine staircase with underlighting and custom water feature. The main living area features floor-to-ceiling windows, a Nexus TV that descends from the ceiling by remote, and a wet bar with an ice maker and storage. The chefs kitchen is an artistic showpiece, complete with a backlit quartzite waterfall island, soft-close cabinets, a built-in wine cooler, and high-end appliances. The private top-floor primary suite offers a spa-like atmosphere with panoramic views. A bonus room on the same level adds versatility, perfect as an office, gym, or library. And a rooftop infinity pool featuring a swim-up bar, ambient lighting, and water features, creating a resort-style oasis. The ground level is designed for entertaining with a summer kitchen, Lynx grill, salt-chlorinated pool, and teak-clad ceilings. A turf yard and paver driveway adds style and functionality. This home is fully equipped with a whole-house generator, elevator, custom closets, remote controlled shades, and an advanced security system with remote access. A stocked 100-bottle wine cellar, ample dockage, a 20x8-foot swimming platform, and so much more. This estate is more than a home--its a lifestyle. Dont miss the opportunity to experience this extraordinary Key Largo retreat.

3 HOMES, OVER 100 PROTECTED DOCKAGE & OVER 550 NATURAL OCEANFRONT BEACH ~Fall in love at first sight as you step into this natural beauty with over a quarter mile of pristine white sand beach that kisses the edge of the Atlantic Ocean. Now being offered for the very first time, this one of a kind legacy property beckons you to bask in original elements of the Florida Keys way of life at Kids Cay. Three charming homes; a timeless 4 bedroom main house plus 4 bedroom guest house and a lovely 2 bedroom caretakers cottage. This tropical and tranquil estate offers ample and protected concrete dockage (104 feet and 34 feet) and oceanfront observation pier. Extra wide and spacious porches adorn every corner of the classic homes and are a seamless blend of indoor and outdoor living maximizing the infinite open water views and constant ocean breezes. Enjoy complete privacy lounging by the resort-style pool or stroll barefoot along your private beach, and nature preserve; a sanctuary for plethoras of beautiful native birds. This estate is the epitome of true island living and serenity and beautifully lends itself to photo shoots, movies, weddings and luxury weekly rentals. This offering is for the south side (over 4 acres upland plus ocean bottom parcel) of property and over 550 of beachfront. See MLS#604054 for entire offering.

Tranquility Haven features the newest construction in Islamorada... completed January 2025! As you enter the gated and fenced sanctuary a long winding driveway leads up to an elevated entrance and convenient 1st floor living access. The 6 bedrooms and 9 bathrooms provide the epitome of coastal living with uninterrupted views of the turquoise waters on the Atlantic Ocean, with serene sunrises, and the gentle symphony of waves as your daily backdrop. Nestled on 210 of private sandy beach, this 2.04ac +/- serene oasis invites you to indulge in 6,946 sf of air-conditioned elegance and 1,800 sf of covered outdoor living designed for relaxation and entertaining. At its heart, a stunning 65 blue lagoon pool with swim-up bar stools, propane fire pit and spacious lounging patio promises unforgettable moments with family and friends.Inside, every detail reflects the designers mastery, from the chefs kitchen with SubZero, Thermador, and Wolf appliances to the grand living spaces that blend sophistication with comfort. The residence boasts 2 master suites that include double bathrooms and closets! A luxurious feature of the 1st floor master suite is a shower al fresco surrounded by a unique orchid garden and immediate access to the spa and pool patio. The 2nd floor master suite ensures more privacy and the ultimate sunrise horizon view! Much more is revealed as you walk from room to room - a flex room provides for possibilities of fitness, office or guests. A family room designed with home theater technology, a 2 car garage together with a beach-access garage and professionally landscaped grounds is complete with a tropical fruit orchard! Begin each day with golden sunrises and end with starlit skies, all within the embrace of an ocean breeze. Encounter warm Winter days and cool Summer nights. Whether hosting lavish gatherings or seeking peaceful solitude, this estate can be your haven - a perpetual island vacation in the Florida Keys!

Fall in love at first sight as you step into this natural beauty with over a quarter mile of pristine white sand beach that kisses the edge of the Atlantic Ocean. Now being offered for the very first time, this one of a kind legacy property beckons you to bask in original elements of the Florida Keys way of life at Kids Cay. Three charming homes; a timeless 4 bedroom main house, separate 4 bedroom guest house and a lovely 2 bedroom caretakers cottage. This tropical and tranquil estate has nearly 8.5 acres of upland plus 7.98 acres of ocean bottom plus ample and protected concrete dockage (104 feet and 34 feet) and oceanfront observation pier. Extra wide and spacious porches adorn every corner of the classic homes and are a seamless blend of indoor and outdoor living maximizing the infinite open water views and constant ocean breezes. Enjoy complete privacy lounging by the resort-style pool or stroll barefoot along your private beach, and nature preserve; a sanctuary for plethoras of beautiful native birds. This estate is the epitome of true island living and serenity and beautifully lends itself to photo shoots, movies, weddings and luxury weekly rentals. Also being offered with south side only for $17m see listing #613236.

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.

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.

An exquisite masterpiece of coastal luxury crafted by visionaries to create the ultimate secluded paradise. This architectural gem, designed by the renowned Siskind architects Bruce Carlson and Steve Siskind, offers an extraordinary lifestyle in an over five-acre waterfront oasis. Raymond Jungles landscape mastery frames the canvas, while Sam Robins interior magic awaits within. Experience approximately 11,000 sq ft of air-conditioned, carefully curated living space that is meticulously crafted with attention to detail. The gross square footage exceeds 17,895 sq ft, including covered outdoor verandas that seamlessly blend indoor and outdoor living. A four-bay air-conditioned collectors car garage awaits your prized vehicles. Additional covered parking porticos and a crushed shell driveway bordered by cut coral provide ample space for guests. Step into a world of tranquility with a private saltwater pond teeming with native sea life. Wander along the stone-through path for an intimate encounter with nature and carefully curated specimens. Situated on a peninsula, this estate offers complete privacy and security. A secluded beach area invites you to dip your toes into the ocean without prying eyes. Hosting soirees on the peninsula grassy area could serve as a helipad with a tiki lounge. Resort-style amenities include a gas-heated oasis pool, hot tub, and waterfall grotto to create a tropical paradise. Built-in swim-jet therapy and a beach entrance enhance your relaxation. Gas-powered tiki torches illuminate the evenings. Thoughtful details throughout, with an air-conditioned equipment room and cabana bathroom, add convenience. The elevated, fully equipped summer kitchen features a push-button elevated TV and a pizza oven, all with unobstructed views. A 450-foot dock with two boat lifts and a private protected boat basin awaits your vessels. This is more than a home; its an unparalleled legacy of luxury and privacy waiting to be claimed.