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Florida Keys Homes on the Bay / Gulf Side of the Island For Sale

Total Listings 365
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$13,900,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
6 Bed, 6 Baths, 4,394 SqFt Days Listed: 31
-6.71% ($1,000,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift220ft.

Welcome to BAYVIEW HIDEAWAY. Situated on 2 SEPARATE LOTS --each with its own parcel ID--the buildable bayfront lot has endless potential. The price per square foot reflects this extraordinary opportunity.This mini estate is surrounded by water on three sides with 435+/- water-frontage and secured by a 6-foot gated entrance. BAYVIEW HIDEAWAY boasts 220+ of concrete dock, complete with three lifts, power, and water. Ideal for boating enthusiasts, the canal accommodates yachts over 80+ feet and offers convenient access to Channel 5 Bridge with 65-foot clearance for seamless bay-to-ocean access. The second lot even has the potential for a helicopter landing.Meticulously renovated by the original builder in 2020-2021, this home was stripped to the bare framework and reimagined with modern updates, including new electric, plumbing, and impact-rated PGT/WinDoor windows and doors, porcelain tile flooring and Level 5 drywall throughout. The property features smart, energy-efficient upgrades, such as 4 Trane AC units with variable-speed smart thermostats, two water heaters, and foam-filled block insulation. Inside, the home offers picturesque water views from every room and features luxurious details, including Turkish marble stairs, vaulted ceilings, Hunter Douglas window treatments, and Italian marble accents in the primary baths. The spacious layout includes six bedrooms, each with private balconies, two primary suites, 4 bathrooms, and a chefs kitchen with Viking appliances, custom cabinetry, and Vetrazzo countertops.The outdoor spaces feature a new saltwater pool built in 2021 with a heater/chiller surrounded by marble pavers, a bar, BBQ area, a gazebo, an orchid house, pergolas, a putting green, and hot tub.Located in Safety Harbor subdivision in Islamorada--BAYVIEW HIDEAWAY is more than just a home; its a lifestyle opportunity. Combining high-end finishes, unparalleled amenities, and a prime bayfront location, this estate is a true gem in the Keys.

$16,990,000
Ocean Reef
Misc Ocean Reef Subdivisiond   - MM: 905.00
7 Bed, 7 Baths, 5,417 SqFt Days Listed: 174
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

With delivery targeted for mid 2025, your dream home is underway at one of the premier locations at the Ocean Reef Club. This 5,417 square foot home will offer direct western exposure on 100 ft. of water frontage with planned 50 T dock.Enjoy beautiful Key Largo sunsets in a private serene setting on Sunrise Cay from this beautifully-appointed, modern coastal home featuring a main house, guest casita and garage, including seven total bedrooms and seven and a half baths. The wide open living space delivers a contemporary, fully-loaded kitchen, great room and dining area. Outside the home, your Ocean Reef Club oasis includes a sundeck with a pool and hot tub overlooking the canal, as well as a complete outdoor kitchen.

$21,900,000
Summerland Key
Niles Channel Subdivision   - MM: 25.00
5 Bed, 5 Baths, 3,392 SqFt Days Listed: 202
Off Shore Isl - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin,Other Dockage,

Welcome to Howell Key! This unique island oasis, purchased in 2010, was developed as an off-grid, private family retreat for a multi-generational remote getaway. Now, this breathtaking 9.69-acre turnkey opportunity is on the market, inviting you to live your offshore island dream or invest in a one-of-a-kind vacation rental experience. Situated off mile marker 25 in Summerland Key, Florida Keys, Howell Key is just a 5-minute boat ride from your private masterpiece. With direct access to both the Atlantic Ocean and the Gulf of Mexico, your watersport dreams can come true daily. Proximity by boat is close to Looe Key National Marine Sanctuary, many sand bars, and the famous 5-star Little Palm Island Resort and Spa. This inviting island sanctuary features dockage accommodating vessels up to 50 feet and an electric gate leading to the marina lagoon. The energy-efficient, immaculate five-bedroom, four-bath home boasts a saltwater pool, exposed beam ceilings, travertine tile throughout, and SIPS panel technology construction. Additional structures on Howell Key include a guest house, garage, animal pens, pickleball court, tiki hut with beach, helipad, and finger dock with a covered sitting area. Plus, a second ROGO-exempt permit allows for constructing another dream home. This is a completely turnkey, fully furnished property that provides a peaceful, tropical escape from the ordinary. This purchase includes a Shore Station Lot completely fenced in to leave vehicles and has a 58 seawall to accommodate your personal ferry. Full list of amenities included in the documents tab.

$22,500,000
Key Largo
Unplatted Lower K.l.   - MM: 92.00
8 Bed, 8 Baths, 8,949 SqFt Days Listed: 332
-10.00% ($2,500,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Boat

Experience Absolute Paradise! A Legacy Florida Keys Estate offering ultimate privacy & tranquility. The Orchid Cove Estate spans 14.5 Acres offering 1,000 ft. of waterfront & Private Beaches accessed through a grand entrance surrounded by a breathtaking canopy of exotic trees. Award winning Botanical gardens surround the property featuring impeccably curated nature trails leading to the main house, a boathouse, guest villas, & beach cove. Main residence rises 10 ft above the ground level, entered through a footbridge surrounded by coral rock waterfalls & koi ponds. Expansive water views, Library, Theater, Spa & Wellness room, Elevator & Chefs kitchen, private boat dockage,10+ car garage, catering facilities, generator & more. Daily spectacular sunsets. Arrive by seaplane, boat, or car.

$25,000,000
Upper Matecumbe Key Islamorada
Russell Estates   - MM: 83.20
7 Bed, 7 Baths, 6,935 SqFt Days Listed: 13
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Basin,Boat

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 homes 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, its an experience.

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 01-29-2025.
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