Zip codes 33036 listings for sale

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$42,000,000 - Plantation Key, FL
88041 Old Highway Plantation Key, FL - 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 Robin's 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 collector's 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; it's an unparalleled legacy of luxury and privacy waiting to be claimed.
2017 | 6 | 8 | 9,843 sqft.
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$31,200,000 - Lower Matecumbe, FL
76180 Overseas Highway Lower Matecumbe, FL - 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, 6 full 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 tap, 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 media-ready living room with blackout shades 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, 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.
2024 | 8 | 10 | 10,228 sqft.
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$29,500,000 - Islamorada, FL
82719 Old Hwy Islamorada, FL - An oasis of coastal elegance and timeless design, this exceptional estate offers over 40,000 square feet of stunning indoor and outdoor living. Blending Hamptons sophistication with Florida Keys charm, every detail has been artfully curated—from shimmering mosaic fountains and sweeping staircases to floor-to-ceiling windows and bespoke stained-glass elevator doors. Intricate wrought-iron balconies, glowing chandeliers, and a luminous fireplace add glamour throughout. Perfectly suited for both refined living and elegant entertaining. This Exquisite home boasts versatile spaces including a half basketball court that transforms into a ballroom, pickle-ball or volleyball court, and a massive rooftop deck ideal for entertaining large crowds.
1995 | 7 | 10 | 10,112 sqft.
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$25,000,000 - Upper Matecumbe Key Islamorada, FL
82768 Overseas Highway Upper Matecumbe Key Islamorada, FL - 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 home's 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, it's an experience.
2017 | 7 | 10 | 6,935 sqft.
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$23,000,000 - Upper Matecumbe Key Islamorada, FL
96 Madeira Road Upper Matecumbe Key Islamorada, FL - ''The Pulse of Islamorada'' ... Iconic Islamorada Restaurant & Cabana Bar available for Sale, Real Estate and Business included. Spanning over 1,000 feet of bayfront and 500 ft of Highway frontage, where the locals & visitors come from near & far to watch nightly sunsets over the bay, enjoy food & libations, and listen to live bands daily. This property includes over 5 acres of real estate (survey available), full service bar with 5 Cop liquor license, 250 seat outdoor restaurant, private party & tournament hosting area. New parking lot, lighting, & drainage completed in 2020 with plenty of parking to expand the business. Concrete building built in 2015/2016 for gift shop, bathrooms, laundry, prep kitchen, storage, and more. In addition, property includes main kitchen, special event tiki bar, dockage, beach, boat ramp, and more. Sale includes 4 on site building rights & 2 boat slips in the Islamorada Yacht Basin located adjacent to property. Room for expansion.Voted Best Sunset year after year. Additional information and financials available upon request. NDA and POF required. Contact Listing Agent .All information to be verified by Buyer/Buyer's Agent.
2011 | 0 | 1 | 0 sqft.
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$20,995,000 - Plantation Key, FL
88351 Old Highway Plantation Key, FL - LUXURY PROPERTY AUCTION: BID June 11th - June 20th, 2025. 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 chef's 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.
2025 | 6 | 9 | 7,738 sqft.
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$20,000,000 - Lower Matecumbe, FL
141 Cortez Drive Lower Matecumbe, FL - 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. 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; 4 bedroom main house, separate 4 bedroom guest house and 2 bedroom caretaker's 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 $15m see listing #613236.
2002 | 10 | 10 | 6,302 sqft.
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$17,000,000 - Lower Matecumbe, FL
75840 Overseas Highway Lower Matecumbe, FL - Welcome to Paradise Islamorada. New construction. 7 bedroom. 7 bathroom. Ready to move in. Make your dream a reality. Mile marker #75. Land 2 acres beachfront lot.
2025 | 7 | 7 | 5,900 sqft.
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$15,000,000 - Lower Matecumbe, FL
141 Cortez Drive Lower Matecumbe, FL - 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. 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; 4 bedroom main house plus 4 bedroom guest house and 2 bedroom caretaker's 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.
2000 | 10 | 10 | 6,302 sqft.
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$11,000,000 - Plantation Key, FL
180 Galleon Road Plantation Key, FL - Modern luxury meets barefoot elegance in this oceanfront masterpiece in Islamorada! Stunning ocean views can be seen from almost every room in this spectacular home. Designed for casual living and entertaining, indoor and outdoor living is seamless and allows for year round enjoyment of the Florida Keys lifestyle. Open ocean views, 380 ft. of dockage with power and water and a cut in boatslip with a 25,000 lb. boatlift will accommodate your boats and water toys. Boasting 6 bedrooms, each with ensuite baths, a 3 story elevator whisks you from the ground level to the main living level on the second floor. Here you will find an open floor plan accented with high coffered ceilings and tall windows and doors opening to ocean views. The kitchen has a large island with quartzite counters and a waterfall edge, GE Monogram appliances and walk in pantry. The primary suite offers ocean views, his and hers closets and a magnificent bath with a double vanity, free standing tub and ingenious double shower. There is a junior primary suite on this level with its own breakfast bar and refrigerator. The game room is on the 3rd floor with exceptional ocean views, service bar and 600 bottle wine vault! Also on this floor are 4 guest bedrooms with ensuite baths. This oceanfront oasis is gated for privacy and features a 3 car garage plus an additional single car garage! The pavered driveway leads to the front door and entrance foyer where you see the pool and oceanfront beauty shining through. To the left is the gym to work off last night's dinner and the pool deck and dock are straight ahead ready for some fun today. There is plenty of shade by the outdoor kitchen or you can relax on the oceanfront chaises. The pool with sun shelf and spa are ready for your friends and family to enjoy. Need a little extra shade? An oceanfront tiki sits beside a fire pit for the perfect transition from day to night! Tiki torches along the waterfront are the perfect evening accent!
2023 | 6 | 8 | 7,160 sqft.