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

Total Listings 185
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$12,900,000
Key Colony
Coury Subdivision   - MM: 53.50
4 Bed, 4 Baths, 4,752 SqFt Days Listed: 419
-13.42% ($2,000,000) 1 Price Change : Last Change 86 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: 169
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!

$21,000,000
Marathon
Sea Crest Heights   - MM: 52.00
5 Bed, 5 Baths, 8,573 SqFt Days Listed: 108
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.

$27,500,000
Marathon
Coco Plum Beach   - MM: 54.50
9 Bed, 9 Baths, 19,124 SqFt Days Listed: 14
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Slip50ft.

Discover the epitome of coastal luxury in this brand-new, beachfront estate, perfectly positioned just steps from the sandy shores. Boasting an impressive 200 feet of direct ocean frontage, this captivating masterpiece offers the ultimate in refined living and resort-style comfort. Inside the private, gated entry, the estate features nine beautifully appointed bedrooms, nine bathrooms, one half bath, an expansive kitchen with Sub-Zero & Wolf appliances, executive office, a state-of-the-art gym with its own full bath, and a stylish game room & media room designed for both relaxation and entertainment. The chef-inspired summer kitchen sets the stage for effortless outdoor dining, while the separate guest house, complete with three bedrooms and two full baths, offers a private retreat for visiting family and friends. The elevator services all three floors. The full bar off the main living area includes a large wine cooler, ice maker and refrigeration drawers. Laundry rooms are conveniently located on the first floor, second floor, and guest quarters. Four garage bays provide ample space to house eight vehicles, with nine automated garage doors, plus a tackle room and storage. The oversized 100 x 26 pool with a 16 x 16 beach entry delivers a resort-caliber experience right in your own backyard. Every inch of this home showcases impeccable craftsmanship and top-of-the-line finishes, creating a space that is as functional as it is breathtaking. As a rare and remarkable bonus, this property includes a coveted 50-foot boat slip at the prestigious Bonefish Marina (less than 1 mile on the same street), perfect for exploring the surrounding waters in style. The Marathon International Airport is only 4 miles away for those with private aircraft. Whether youre hosting grand events or seeking a tranquil escape, this estate offers it all. Seize the opportunity to own this extraordinary coastal sanctuary, where luxury knows no bounds and your dream lifestyle becomes reality.

$35,000,000
Marathon
Crains Subdivision   - MM: 58.00
9 Bed, 9 Baths, 9,530 SqFt Days Listed: 58
Multi-Units - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Basin,Boat

Zephyr Cove; the extravagant aquatically inspired retreat that you deserve. Located on the breathtaking waterfront nestled along the Gulf and designed and built by DAsign Source. This stunning estate invites you to experience the perfect balance of luxury, tranquility, and adventure. With both fresh and saltwater elements woven into its design, every detail has been thoughtfully crafted. At the heart of the property lies a lazy river loop infinity pool, complete with bridges, swim-up pool bar in gazebo, spa with table, lap pool, beach-style entries, and waterfall grotto plus gas fire pit, putting green, and tropical gardens. From floating under the sun, entertaining guests, or enjoying a peaceful evening by the water, this home was manifested for unforgettable moments.Grand main residence vaunts an impressive private primary wing and elegant open spaces designed for comfort and entertainment. Indoor amenities include a temperature-controlled wine room, game room, home theater, fitness center, and conference room; endless ways to unwind and enjoy life. Two additional charming two-bedroom villas and a separate two-bedroom guest house are perched next door, perfect for hosting family and friends with style and privacy.Designed for the ultimate coastal lifestyle with outdoor kitchen and dining areas set against breathtaking Gulf views, ideal for entertaining or simply soaking in the beauty of your surroundings. Ample dockage and multiple boat lifts for your toys, located right between Vaca cut and Toms Harbor Cut for easy Ocean access. Expansive garages and storage spaces provide ample room for vehicles, boats, and all essentials. Whole-home 130kw generator in its own private structure, ensuring peace of mind no matter the season. This is where everyday life feels like youre being pampered at a lavish resort. Step into a world where the beauty of nature meets unparalleled craftsmanship and let the magic of the Gulf welcome you home. 15 min to private airport.

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 04-24-2025.
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