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Upper Keys Homes for Sale, Single Family Houses, MLS Home Listings

Total Listings 367
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$16,000,000
Key Largo
Anglers Park   - MM: 103.00
4 Bed, 4 Baths, 4,000 SqFt Days Listed: 138
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 75ft.Concrete

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.

$16,990,000
Key Largo
Ocean Reef Club   - MM: 905.00
9 Bed, 9 Baths, 6,243 SqFt Days Listed: 24
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift50ft.

�� Experience Elevated Living at Ocean Reef Club!Welcome to one of the most prestigious estates in all of Ocean Reef Club, where elegance,privacy, and world-class amenities converge. Set on over an acre of prime land in this ultra-exclusive gated community, this expansive compound is a rare opportunity to own a truesanctuary within one of Floridas most coveted enclaves.*The Property* Main Residence: 5,425 SF of refined living space Guest House: 818 SF | 2 bedrooms, 1 bathroom, private living area, and full laundry Total Living Area: 6,243 SF | 9 Bedrooms | 9.5 Bathrooms Garage: Oversized 3-car (1,020 SF) Lot Size: 49,607 SF / 1.12 Acres Outdoor Living Area: 1,636 SF of covered alfresco enjoyment Dock: 50 private dock with immediate access to world-class fishing and boatingCrafted with the highest standards of construction, this two-story concrete shell home featuresstucco and stone finishes complemented by a standing seam metal roof--built for both luxuryand resilience. Inside, you will find metal and wood-framed interiors, highlighted by finematerials and meticulous craftsmanship throughout.✨ Luxury Interiors & Amenities Chef-inspired kitchen with 72 Lacanche gas range and Sub-Zero refrigeration Two gas fireplaces for cozy ambiance and elegance Two second-floor primary suites, offering flexibility and privacy Complete elevator system for seamless access across levels High-end finishes including Kohler & Toto plumbing fixtures throughout�� Ocean Reef Club LifestyleAs an owner in Ocean Reef, you gain access to an unparalleled private community experience,including:-Private Airport & Helipad for seamless travel- 175-slip Deep Water Marina and yacht concierge services- 2 Championship Golf Courses & Racquet Club- World-Class Fishing, Diving, and Water Sports-On-Site Private Sc

$20,995,000
Plantation Key
Pearl City   - MM: 88.00
6 Bed, 6 Baths, 7,738 SqFt Days Listed: 102
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 230ft.

LUXURY PROPERTY AUCTION: BID 20-30 MAY. Listed for $20.995M. Starting Bids Expected Between $8M-$11M.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 7,738 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 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, tranquil Summer nights.

$22,500,000
Key Largo
Unplatted Lower K.l.   - MM: 92.00
8 Bed, 8 Baths, 8,949 SqFt Days Listed: 432
-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: 113
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.

$29,500,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
5 Bed, 5 Baths, 8,680 SqFt Days Listed: 31
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 100ft.

$42,000,000
Plantation Key
Plantation Beach   - MM: 87.50
6 Bed, 6 Baths, 9,843 SqFt Days Listed: 88
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Other Dock

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.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 05-09-2025.
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