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

Total Listings 169
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$8,999,000
Key Colony
Coury Subdivision   - MM: 53.50
4 Bed, 4 Baths, 4,888 SqFt Days Listed: 61
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Located within exclusive Key Colony Beach, nestled on a lushly landscaped, oversized lot, lies a stunning Oceanfront estate of unrivaled opulence. Boasting in-ground saltwater pool and spa, private sandy beach, firepit, built-in outdoor kitchen, and sprawling composite dock with 40K boat lift, this home caters to elevated Florida Keys living, and the 13,659 Sq. Ft. manicured lot across the street is also included in the sale! Enter through soaring glass doors into an elegant foyer, where turquoise Ocean Views are the focal point of the courtyard in the heart of the home. In the South wing, a gorgeous Great Room features access to both the courtyard and a covered veranda, boasting views of the grounds, pool, and Open Water. A well-appointed wet bar, complete with refrigerator and wine cooler, lends itself to entertaining. In the North wing, the showstopping Chefs Kitchen, with premium appliances, including gas range, and large island with storage and seating, is designed for hosting memorable gatherings. Visitors will enjoy superior accommodation in either the downstairs guest suite, or either of two upstairs en suite guest bedrooms. Retire to a palatial primary suite, with large walk-in closet with laundry, luxurious en suite, sitting area, and built-in wet bar, provided abundant privacy in the upstairs South wing. Wake up to magnificent Ocean Views and enjoy morning coffee on the private primary balcony. Outside, host memorable events in the lush backyard oasis. Lounge poolside on the sun deck or beachside in a shaded hammock. Grill up your fresh catch and enjoy sunset cocktails from the well-appointed, built-in outdoor kitchen, and cozy up by the firepit under a blanket of stars, to enjoy balmy ocean breezes. This spectacular property is designed for resort-style living, situated in sought-after Key Colony, boasting incomparable community amenities and with convenient proximity to delectable dining and stores in town!

$9,999,000
Marathon
Crains Subdivision   - MM: 58.00
4 Bed, 4 Baths, 5,168 SqFt Days Listed: 148
-4.77% ($501,000) 1 Price Change : Last Change 4 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

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.

$10,500,000
Key Colony
Coury Subdivision   - MM: 53.50
5 Bed, 5 Baths, 4,215 SqFt Days Listed: 635
-4.54% ($499,000) 1 Price Change : Last Change 334 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Other Dock

Over an acre on a private point in Key Colony Beach surrounded by water on 3 sides. Unparalleled location, relaxation and recreation-this house has it all. It doesnt get any better than this. A canal sits on one side with a dock for water toys. The back looks out onto Vaca Cut protecting your boat with 25k lb lift and quick access to the ocean. Swimming pool and waterfall spa glisten with iridescent blue tiles surrounded by views on all sides. The deck and and covered patio provide areas to lounge in the sun or shade, cook in your outdoor kitchen and dine while watching dolphins play. With room for over 100 people, entertaining is a joy here. The living room windows offer views of turquoise waters. Dining room and kitchen share the views as well. Chefs kitchen with double oven, granite counter tops and top of the line appliances. Italian marble floors throughout the house. On the main floor you will find a den or bedroom, a laundry room and several air conditioned garages. Garages are currently set up as an office, playroom and storage. A gorgeous half bath has a custom marble floor. Another full bath can be accessed from the den or from the outside for guests using the pool. Venture up the marble staircase with picture windows all the way up and custom wrought iron railings to the second floor landing with incredible views. Watch the sunset from the Master Bedroom right from your bed or from the balcony. The Master Bath has a spa tub, mosaic shower and honey onyx marble double vanity. A custom walk in closet finishes this suite. There are 3 additional bedrooms all with en suite bathrooms and walk in closets. This home was built to withstand 200mph wind. Steel and poured concrete along with Anderson Hurricane custom windows makes this house a fortress, along with security system, landscape lighting and so much more. Fully furnished - just bring your bathing suit!

$12,900,000
Key Colony
Coury Subdivision   - MM: 53.50
4 Bed, 4 Baths, 4,752 SqFt Days Listed: 329
-13.42% ($2,000,000) 1 Price Change : Last Change 55 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 62ft.

Welcome to The Sandcastle, nestled in exclusive Key Colony Beach, this custom DAsign Source home epitomizes luxury and boasts open water views! Situated on a gated double lot, with a private sandy beach and lush tropical landscaping, this property offers unparalleled resort-style amenities! Upon entry into a grand foyer, wrought iron staircases lead to an opulent great room, highlighting the view of the saltwater infinity pool and spa with breathtaking views of the Atlantic Ocean beyond. Pool refinished October 24 with all new equipment and water features! Retire to a private primary wing with splendid views from the bedroom, access to the pool deck, en suite bathroom, walk-in closet, and attached study. A masterfully appointed Chefs kitchen is equipped with custom cabinetry, generous island, and high-end appliances. The gorgeous banquette offers stunning open ocean views while the formal dining room is nearby for larger gatherings. Relax on one of several porches such as the covered veranda just off the kitchen which is tailor-made for poolside entertaining with a well-equipped Summer Kitchen. After youve enjoyed the front row seat of stunning sunset views, host memorable movie nights in the exquisite home theater! Family and visitors will enjoy elevated accommodation in any of three upstairs guest suites, each with en suite bathrooms, and one with its own private balcony offering panoramic ocean views! The intuitive floor plan design has added bonuses such as two laundries, a pool accessible bath, a loft, an elegant elevator accessing all floors, and a first-floor garage with secure parking for 4+ vehicles with added storage. Built to withstand the elements with impact doors and windows. Included in the sale is an additional manicured lot, just across the street with a deep-draft canal, complete with a 62 dock to enjoy frequent boating and fishing with ease. In an established neighborhood, but in proximity to town, this spectacular property wont last long!

$13,400,000
Duck Key
Plantation Island   - MM: 61.00
3 Bed, 3 Baths, 4,065 SqFt Days Listed: 79
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!

$13,895,000
Marathon
Seawatch   - MM: 53.50
5 Bed, 5 Baths, 4,187 SqFt Days Listed: 683
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!

$14,500,000
Marathon
Casa Manana Shores   - MM: 50.50
6 Bed, 6 Baths, 10,852 SqFt Days Listed: 207
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin,Boat Slip218ft

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!

$14,999,000
Key Colony
Coury Subdivision   - MM: 53.50
9 Bed, 9 Baths, 7,270 SqFt Days Listed: 402
-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: 18
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp,Other Dock

Immerse yourself in a tropical paradise where luxury knows no bounds. This breathtaking five-acre oceanfront estate, with 244 feet of private ocean frontage, is the crown jewel of the Florida Keys. From the moment you pass through the gates, youll be captivated by a world of elegance, privacy, and unparalleled amenities.At the heart of this premier estate lies a resort-style pool oasis, complete with waterfalls, a waterslide, and a Tahitian-style river with private bedroom balconies offering entrance to the pool and leading to a swim-up tiki bar--perfect for lavish entertaining or tranquil escapes. The custom-designed 5,600+/- square foot main residence by DAsign Source showcases exquisite craftsmanship and architectural brilliance. A separate 2,999 sq.ft. guest house offers a private retreat with its own kitchen, multiple bathrooms, and spacious living areas, ideal for hosting guests or staff. A private marina and boat ramp provide direct access to the world-famous waters of the Keys, with the bait shack nestled alongside for all things fishing and boating. Inside, every corner of this estate is designed to impress. A gourmet kitchen, opulent guest suites with private balconies offering entrance to the the lush poolscape, and a luxurious movie theater ensure every moment here is extraordinary. The primary en-suite dazzles with a stunning bathroom offering a retreat style sanctuary. Beyond the elegance, the estate is built with durability and functionality in mind, featuring impact-resistant windows and doors, generator, and cistern. Outside, explore expansive porches, a rain forest and fruit orchard, multiple garages, a carriage house, a tortoise habitat and even the potential for a private hangar. This estate isnt just a home; its a lifestyle--your personal resort blending tropical serenity, architectural excellence, and unmatched prestige. Discover the ultimate in coastal living, where every day feels like an extraordinary getaway.

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 01-24-2025.
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