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$6,450,000
Shark Key
Shark Key   - MM: 11.00
4 Bed, 4 Baths, 3,875 SqFt Days Listed: 149
-7.86% ($550,000) 3 Price Changes : Last Change 25 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Motivated Seller! Discover luxury living in this stunning 4BD/3.5BA custom home in the exclusive gated community of Shark Key. Featuring 3,875 SF of refined space, this residence offers soaring ceilings, designer finishes, a gourmet kitchen with Wolf & Miele appliances, and seamless indoor-outdoor living. Enjoy a heated infinity pool, spa, and breathtaking Gulf sunsets. Dual primary suites, office/flex room, EuroCave wine bar, and lush tropical surroundings complete this waterfront oasis. Private, secure, and built to impress.

$6,200,000
Shark Key
Shark Key   - MM: 11.00
4 Bed, 4 Baths, 5,180 SqFt Days Listed: 184
-11.43% ($800,000) 2 Price Changes : Last Change 23 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Timeless European Elegance! This custom 4BD/5BA Mediterranean villa in gated Shark Key offers 5,180 SF of luxurious living. Features include soaring ceilings, gourmet Viking kitchen, office, game room, and stunning open-water views. Enjoy indoor-outdoor living with expansive decks, pool, fireplace, and multiple entertaining areas. The spacious primary suite includes a sitting area, wet bar, dual walk-ins, and private terrace. Additional highlights: Borano mahogany doors, elevator-ready design, chair lift, impact windows/doors, dual garages, and first-floor guest suite. Amenities include private lagoon, beach, tennis, pickleball & clubhouse. Furnished with exclusions.

$5,700,000
Shark Key
Shark Key   - MM: 11.00
4 Bed, 4 Baths, 5,300 SqFt Days Listed: 115
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Welcome to one of Shark Keys landmark estates--a custom-built, beautiful Mediterranean-inspired home. This exclusive property offers timeless architecture, open water views, and an unparalleled island lifestyle.Nestled on the northern end of Shark Key and set back from the road for privacy, this 5,300-square-foot estate sits on a 21,075-square-foot lot with breathtaking open water views. Designed for comfort and entertaining, the home features 4 bedrooms, 4.5 bathrooms, a private office, a home theater, an elevator, a full bar, and expansive balconies and elegant terraces that invite you to take in stunning sunrises and peaceful water views.Each of the bedrooms has an ensuite bathroom and private balcony, while the primary suite boasts incredible water views. The outdoor living spaces are equally impressive, featuring a pool, hot tub and ample room for entertaining and lounging. Theres also space to add an observation dock for a flats boat.Enjoy the exclusive amenities of Shark Key, including pickleball, tennis courts and a private sandy beach. Located just minutes from Key West, yet offering a private retreat, this estate is truly one of a kind.This lovingly maintained home presents an exciting opportunity to update and make it your own while preserving its classic Mediterranean charm.Dont miss this rare offering--schedule your private showing today!

$5,195,000
Shark Key
Shark Key   - MM: 11.00
5 Bed, 5 Baths, 4,176 SqFt Days Listed: 69
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Tucked behind swaying palms and lush tropical landscaping, this elegant and timeless waterfront estate captures the essence of Florida Keys living--from breathtaking sunset views to exceptional outdoor spaces. Whether youre lounging on your private beach or entertaining by the pool, every moment here is a reminder of why you chose island life.Inside, sun-drenched living areas showcase wide-open Gulf views and an abundance of natural light. The gourmet kitchen is thoughtfully designed with custom cabinetry, high-end appliances, and a spacious island--ideal for both everyday living and entertaining. Upstairs, the master suite features panoramic water views and a generous walk-in closet. Three additional bedrooms are located on the upper level, with a fifth bedroom and full bath on the main level offering added flexibility.Designed for seamless indoor-outdoor living, the home opens to a private deck, sparkling pool, and an observation dock--perfect for catching every sunset. Additional features include a copper patina roof, a 3-car covered carport, full generator, ample storage and a wave runner lift.Located in the prestigious, gated community of Shark Key, just minutes from Key West, this estate offers access to resort-style amenities including a clubhouse, inland swimming lagoon and beach, plus pickleball and tennis courts.24 Cannon Royal Drive is everything you love about the Keys--all wrapped into one exceptional waterfront property.

$4,695,000
Shark Key
Shark Key   - MM: 11.00
4 Bed, 4 Baths, 3,750 SqFt Days Listed: 40
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

Hidden away in the exclusive enclave of Shark Key, 37 Cannon Royal Drive offers a rare balance of architectural elegance and coastal tranquility. This four-bedroom, four-and-a-half-bath home is perfectly positioned on over third an acre of waterfront property, where walls of glass frame sweeping views of the Gulf and fill the interiors with natural light.Inside, a series of exquisite arches adds a touch of old-world charm and craftsmanship, softening transitions between spaces and lending the home a sense of timeless character. Each bedroom is a private retreat with its own en suite bath, offering comfort and privacy for both residents and guests.The open-concept layout features soaring ceilings and expansive living areas that flow effortlessly to the outdoors. A lush tropical landscape surrounds a serene pool and spa, ideal for relaxing or entertaining. Beyond, an elevated observation deck and private dock extend your living space over the water--perfect for sunset views, paddleboarding, or simply taking in the stillness of the sea.Just minutes from Key West, yet worlds away in atmosphere--this is island living, redefined.

$2,950,000
Shark Key
Shark Key   - MM: 11.00
3 Bed, 3 Baths, 3,329 SqFt Days Listed: 273
-17.94% ($645,000) 4 Price Changes : Last Change 51 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

If island living is your dream, 39 Cannon Royal Drive in Shark Key is the perfect place to make it a reality. Located in one of the most exclusive and sought-after gated communities in the Florida Keys, this Caribbean-inspired estate offers a tropical escape like no other.Set within this private community, the home boasts stunning, panoramic waterfront views of the Gulf of Mexico, all while being just minutes from the vibrant energy of Key West. The moment you step inside, youre greeted by soaring ceilings and a grand staircase, offering a dramatic entry to the open-concept living spaces. Every corner of this home is designed to maximize its breathtaking surroundings, with the primary bedroom, kitchen, and living areas all enjoying expansive water views.This tropical retreat offers 3 spacious bedrooms, a dedicated office, and the rare convenience of a garage--blending luxury and practicality seamlessly. Outside, the inviting pool serves as your personal oasis, while the prime waterfront location opens the door to endless adventures. Boating, paddleboarding, and kayaking are just steps away, with space to keep a flats boat for easy access to sandbars and world-class fishing.Whether youre searching for a winter retreat or a year-round sanctuary, 39 Cannon Royal Drive is the ultimate escape to island paradise.Shark Key amenities include tennis courts, pickleball courts, swimming lagoon, clubhouse and a private beach.

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 06-15-2025.
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