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Middle Keys Real Estate for Sale, Homes and Condos in the Florida Keys

Total Listings 425
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$13,400,000
Duck Key
Plantation Island   - MM: 61.00
3 Bed, 3 Baths, 4,065 SqFt Days Listed: 110
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Other Dock

Nestled within the confines of exclusive Plantation Island, at the end of a quiet cul-de-sac, lies a monumental Oceanfront estate of unparalleled proportion. Enveloped in lush tropical landscaping, and sprawling across an oversized 17,900 Sq. Ft. Point Lot, boasting stunning Open Water Views, every detail has been considered at this coastal retreat in coveted Hawks Cay! Enjoy Direct Ocean Access with approximately 200 of concrete seawall, with additional dock featuring jetski and boat lifts, this exceptional property allows for frequent boating with ease. Cool off in the resort-style, saltwater infinity pool, or sink into a luxurious hot tub at days end while taking in stunning Sunset Views. Venture inside this colossal masterpiece through a sleek, glass elevator. The show-stopping Great Room features soaring ceilings, well-appointed wet bar, and walls of impact-resistant doors and windows which open to unobstructed Ocean Views. Ideal for entertaining, the open-concept main living space flows seamlessly into an expertly-equipped Chefs Kitchen, complete with premium JennAir appliances, ample prep- and storage space, and generous peninsula with counter seating. Guests will enjoy elevated accommodations in a separate wing, with elegant en suite bathrooms, and access to a spacious veranda overlooking the well-manicured yard and Open Ocean beyond. The primary suite epitomizes luxury, boasting an expansive walk-in closet with custom built-in storage, opulent en suite bathroom, with Ocean Views, deep soaking tub, walk-in shower adorned with walls of onyx stone, and veranda access. The primary bedroom features impact-resistant, pocket sliding glass along two walls, which open entirely for enjoying sublime sunsets and ocean breezes; relax and unwind in this exceptional retreat. The property offers a plethora of parking and storage with detached garage, open- and street parking. Peace and tranquility abound at this extraordinary property!

$13,500,000
Marathon
Casa Manana Shores   - MM: 50.50
6 Bed, 6 Baths, 10,852 SqFt Days Listed: 238
-6.90% ($1,000,000) 1 Price Change : 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!

$13,895,000
Marathon
Seawatch   - MM: 53.50
5 Bed, 5 Baths, 4,187 SqFt Days Listed: 714
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip560ft.Rip R

If you are looking for a beautiful place to call home, your very own paradise awaits! Located in the heart of the Florida Keys, Marathon is a tranquil and serene place to live, surrounded by the crystal clear waters of the Gulf of Mexico. This modern beachfront property has it all. Its one of a kind, unique and breathtaking! Enjoy island living in this stunning 5 bedroom home with views from every room. Come experience the beauty of the Florida Keys and make Marathon your new home. If privacy is important to you, this is the home for you. Your private beach awaits along with a boat dock which has a 25,000 lbs boat lift attached, dock has room for a yacht and jet skis. Property also includes an additional boat slip within the Seawatch marina. Also enjoy entertaining at your very own tiki bar and custom outdoor kitchen. Want a drink but dont want to get out of the pool? No problem. Swim up to the pool bar and enjoy a refreshing drink while still soaking up the sun. Once youre here, you have no reason to leave!

$14,999,000
Key Colony
Coury Subdivision   - MM: 53.50
9 Bed, 9 Baths, 7,270 SqFt Days Listed: 433
-17.59% ($3,201,000) 4 Price Changes : Last Change 13 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Nestled along the sun-kissed shores of exclusive 15th Circle on prestigious Key Colony Beach is the iconic Lighthouse. This expansive and recently updated home offers the epitome of luxury coastal living. With its private beachfront, youll wake up to the gentle lull of the waves and breathtaking views of the Atlantic Ocean. Relaxation meets sophistication. This spacious residence boasts:Generously sized living spaces designed for comfort and coastal elegance married with an open concept capsulating the tranquil Atlantic Ocean views.Upgraded kitchen equipped with modern appliances, perfect for culinary enthusiasts and entertainers alike.9 stylish bedrooms, each offering serene views and ample natural lightImpeccably renovated bathrooms with premium fixtures and finishesOwners quarters for unparalleled privacy and comfort boasting an Owners Suite that coastal living dreams are made of, complete with a generous walk-in closet, steam shower, tub, double vanity with storage galore, a separate living space with wet bar, pilates and music studio overlooking the ocean, beautiful home office and so much more. Private beachfront, one of a kind sparkling oceanfront pool for refreshing dips and lazy afternoons under the sun20k lb boat lift and private mooring ball granting seamless access to the crystal-clear watersOutdoor spaces ideal for entertaining, from intimate gatherings to lavish partiesWhether you seek a serene retreat or an entertainers dream, this Key Colony Beach gem offers the ideal canvas to live your coastal dream. Experience the allure of Florida living in this luxurious waterfront haven. Embrace the serenity of oceanfront luxury living.

$21,000,000
Marathon
Sea Crest Heights   - MM: 52.00
5 Bed, 5 Baths, 8,573 SqFt Days Listed: 49
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp,Other Dock

Discover the crown jewel of the Florida Keys.This extraordinary five-acre oceanfront estate redefines luxury, offering 244 feet of private ocean frontage and unmatched tropical serenity. From the moment you pass through the gated entrance, youll be immersed in a world of elegance, privacy, and unparalleled amenities.A timeless Chicago brick-paved driveway winds gracefully along the lush rain forest and fruit orchard, leading through the grand Palm Alley to the heart of the estate, setting the tone for the tropical oasis that awaits.The custom-designed 5,600+/- sq. ft. main residence by DAsign Source showcases architectural brilliance and exquisite craftsmanship. A separate 2,999 sq. ft. guest house includes its own kitchen, multiple bathrooms, workshop, and spacious living areas, making it ideal for hosting guests or staff.The resort-style pool features waterfalls, waterslide, a Tahitian-style river, an expansive spa, a swim-up tiki bar, and a tiki village. Private bedroom balconies provide direct access to this stunning pool, making it perfect for tranquil escapes and lavish entertaining.Boating enthusiasts will love the private marina, boat ramp, and charming bait shack, offering instant access to the world-famous waters of the Keys for fishing, diving, and boating adventures.Inside, the estate is designed to impress, featuring a gourmet kitchen, opulent guest suites with private balconies to the pool, and a luxurious movie theater. The primary en-suite dazzles with a spa-like sanctuary, ensuring every moment here is extraordinary.Beyond the elegance, this estate is built for durability, with impact-resistant windows and doors, generator, and cistern. Outside, enjoy expansive porches, multiple garages, a barn, and a tortoise habitat . With potential for a private hangar, this property offers unmatched exclusivity.Experience the pinnacle of Florida Keys living--where luxury, tranquility, warmth and prestige come together in perfect harmony.

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 02-24-2025.
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