Plantation Key Homes with Bay Waterfront features

Plantation Key Homes with Bay Waterfront features

Welcome to Plantation Key, a hidden gem nestled in the heart of the Florida Keys, within Monroe County. This enchanting island offers a unique blend of tropical beauty, vibrant culture, and a laid-back lifestyle that captivates residents and visitors alike. With its stunning bay waterfront properties, Plantation Key is the perfect destination for those seeking a serene escape or a vibrant community to call home.

Imagine waking up each morning to the gentle sounds of waves lapping against the shore, surrounded by lush palm trees and the sparkling waters of the bay. Homes on Plantation Key with waterfront features offer not just a place to live, but a lifestyle filled with adventure and relaxation. Whether you’re interested in boating, fishing, or simply soaking up the sun on your private dock, these properties provide unparalleled access to the natural beauty that the Florida Keys are renowned for.

The island is also home to a vibrant community, with a variety of local shops, restaurants, and recreational activities. Enjoy fresh seafood at waterfront dining spots, explore the nearby state parks, or take a leisurely stroll along the picturesque beaches. With an array of homes available, from charming cottages to luxurious estates, Plantation Key caters to diverse tastes and lifestyles.

Embrace the island life in Plantation Key, where every day feels like a vacation. Discover your dream waterfront home and experience the magic of living in one of Florida’s most sought-after locations. Your paradise awaits!

Newest Plantation Key Homes with Bay Waterfront features

$1,800,000
2 Beds ⋅ 3 Baths ⋅ 621264 MLS
RARELY AVAILABLE AT FUTURA YACHT CLUB! This beautifully remodeled end-unit townhome offers an exceptional Florida Keys lifestyle, complete with two side-by-side deeded boat slips, accommodating vessels up to 39 feet, with the option to add lifts. One of only a select few residences in the community with coveted side windows, that capture expansive panoramic bay views and stunning sunsets. Two balconies provide the perfect setting to relax, entertain, and enjoy the spectacular waterfront surroundings. This fee-simple property has the feel of a single family home and features 2 spacious suites, 2.5 baths, a full-size washer and dryer, an outdoor kitchen and covered parking below. Futura Yacht Club is ideally close to everything while offering a wonderful waterfront lifestyle. Amenities include a private marina, boat ramp, swimming pool, tennis/pickle-ball, basketball courts, and boat and trailer parking. With immediate access to the bay and ocean, boating, fishing, and enjoying the beautiful Florida Keys are just steps away. Opportunities to own an end-unit townhome with two rare deeded boat slips, panoramic bay views, and this level of remodeling are rarely available. Don't miss your chance to own a truly special piece of paradise.

88540 Overseas Highway Unit 716, Tavernier
$487,500
2 Beds ⋅ 2 Baths ⋅ 621201 MLS
Welcome to your Florida Keys retreat at Summer Sea! Enjoy bay views from your private open deck area. This 2-bedroom, 1.5-bath condo offers updates throughout and coastal living in the highly sought-after, gated Summer Sea community. Bright, stylish, and filled with natural light, this home is your key to island paradise. Unwind while soaking in breathtaking sunsets from the private beach or the rooftop observation deck with panoramic views of the Florida Keys. Community resort-style amenities include a heated/chilled swimming pool, fully equipped fitness center, on-site storage, and a shared freezer/ice machine. Boaters take note: first-come, first-served dockage accommodates vessels up to 26 ft (tip-to-tip) with quick, easy access to the backcountry and open ocean. Spend your days fishing, kayaking, paddleboarding, or diving in crystal-clear waters. Located just minutes from dining, shops, and local favorites.

88500 Overseas Highway Unit 407, Tavernier
$14,000,000
5 Beds ⋅ 4 Baths ⋅ 621096 MLS
The most sought-after bay in all the Florida Keys, and one of the largest properties on it. This true double lot spans 1.3 acres with more than 250' of bayfront facing due west for the perfect nightly sunset. A white sand beach transitions into the clear bay waters, while a protected basin offers a 20,000 lb. lift accommodating up to a 40' boat and a 3,000 lb. skiff lift. Ultra-private, with no neighbors in sight and expansive green lawns throughout. The home is sophisticated yet inviting, with an incredible attention to detail throughout and a distinctive blend of Tuscan Mediterranean architecture and classic Keys styling. Enter through the gates into a private courtyard and open-air atrium with freshwater ponds and fountains. An elevator provides access to the second floor, where a one-of-a-kind living room overlooks the bay with exposed wood beams and tongue-and-groove ceilings. Updated throughout while preserving its original ornate finishes, this level flows from the living and dining rooms into the kitchen with a gas range and dumbwaiter. The bayfront primary suite features an impressive bath with dual vanity areas. Two additional bedrooms share a Jack-and-Jill bath, plus a half bath finishes off the second floor. Halfway down the main staircase is the entrance to one of the favorite rooms in the home: the library. With vaulted ceilings and a fireplace, it is the ultimate setting to work, relax with a good book, or serve as a fifth bedroom. The ground floor offers a separate ensuite guest bedroom, garage with front and rear doors, laundry room with double washers and dryers, and an outdoor kitchen. Outside, a massive 40' x 22' pool features a hot tub and beach-entry shelf. Extensive uplighting and downlighting illuminate the property at night. An additional front lot includes a detached structure currently used as a gym and storage. A once-in-a-lifetime opportunity to own one of Islamorada's most prized bayfront estates.

350 Buttonwood Bight Ln, Tavernier
$999,000
3 Beds ⋅ 2 Baths ⋅ 621074 MLS
Discover easy bayfront living in this beautifully updated townhome at Executive Bay Club, where breathtaking views of Florida Bay take center stage. The open living area and kitchen enjoy beautiful, unobstructed bay views, while the upstairs primary bedroom offers its own spectacular waterfront perspective. The main living level features level tile flooring and a comfortable, inviting layout designed to take full advantage of the setting. Upstairs, you'll find three bedrooms plus a versatile loft and a spacious bath with a jetted tub and separate shower. Executive Bay Club has recently completed significant community improvements, including a replaced and expanded dock, an updated clubhouse, pool, pool deck and pool bathrooms, all completed within the past two years. With these improvements already made, there are no pending assessments. Move-in ready and ideally positioned on Florida Bay, this is a wonderful opportunity to own a waterfront townhome in one of the Keys' most desirable communities. Don't miss your chance to enjoy bayfront living, beautiful sunsets and the relaxed Florida Keys lifestyle at Executive Bay Club.

87200 Overseas Hwy Unit J 6, Islamorada
$15,000,000
621011 MLS
Discover an extraordinary opportunity on Florida Bay in Plantation Key, offering a rare combination of privacy, natural beauty and approximately 1,250 feet of waterfront with sweeping open-water views and spectacular sunsets. The property encompasses 21+ acres, with approximately 5 acres already cleared for the homesite and improvements. The remaining acreage creates an exceptional natural backdrop and sense of seclusion rarely found in the Florida Keys. A private drive winds through the tropical surroundings to the homesite, while a completed observation dock offers a beautiful setting to enjoy Florida Bay. Designed for this remarkable property is an exceptional 8-bedroom luxury residence created for sophisticated Keys living. Plans feature eight bedroom suites, expansive living and entertaining spaces, a chef-inspired kitchen with oversized island, private office, game room, elevator, extensive garage and storage areas, covered balconies and terraces, plus a pool and spa with generous outdoor living areas. For a buyer who purchases prior to completion, a unique opportunity awaits. The seller will pay the building costs for the planned residence, subject to the terms, specifications and allowances of the purchase agreement. Depending on the stage of construction, the buyer may also have the opportunity to personalize available finishes, selections and certain design elements. Ideally positioned near Snake Creek, enjoy convenient Bay-to-Ocean access with no fixed-bridge restriction and proximity to Founders Park. A remarkable opportunity to create a private Florida Bay retreat where luxury, privacy and the natural beauty of the Keys come together in one exceptional setting.

86600 Overseas Hwy, Islamorada
$6,195,000
4 Beds ⋅ 5 Baths ⋅ 620986 MLS
Experience the ultimate Islamorada waterfront lifestyle in an exceptional contemporary custom bayfront residence, designed by its current owners, with sophisticated architecture, exceptional construction, and premier boating amenities. Perfectly positioned on a cul-de-sac to capture spectacular year-round sunsets across Florida Bay, the tri-level residence offers approx. 3,200 Sqft of living space, an additional 800 Sqft of covered, tiled balconies, four bedrooms, each with an en suite bathroom, plus a convenient half bath. Natural stone flooring, custom cabinetry, quality finishes, and an elevator serving all interior living levels. Built for lasting durability, the home features reinforced concrete construction, galvanized reinforcing steel, a solid concrete roof, impact windows & doors plus automatic hurricane curtains protecting the main waterfront terrace. The spectacular 1,400 Sqft rooftop sun deck crowns the residence, showcasing panoramic views across Florida Bay, unforgettable year-round sunsets, & a fire pit for entertaining or relaxing under the stars. Designed for the boating enthusiast, the property offers immediate deep-water access, two boat lifts at +/- 25,000 and 12,000 pounds, and an enclosed tackle room/workshop for fishing gear and marine equipment. Low-maintenance grounds feature artificial turf, coral rock hardscaping, and irrigated tropical landscaping. The spacious backyard offers ample room for a future resort-style pool overlooking Florida Bay adjacent to the existing chickee hut. A spacious double covered carport with 9.5-foot ceilings provides generous parking for multiple vehicles, trailers, golf carts & recreational equipment. Combining contemporary custom design, exceptional concrete construction, expansive indoor/outdoor living, premier boating amenities, breathtaking sunset views, and endless opportunities for waterfront entertaining, the residence represents luxurious bayfront living at its finest in the Florida Keys.

144 N Rolling Hill Rd, Islamorada
$499,900
2 Beds ⋅ 2 Baths ⋅ 620763 MLS
Welcome to Summer Seas, a desirable waterfront community in the heart of the Florida Keys! This beautifully maintained 2-bedroom, 1.5-bath condominium offers the perfect blend of comfort, convenience, and island living. Enjoy a bright and inviting layout with an open living area, comfortable bedrooms, and a private balcony to relax and take in the tropical surroundings. The community features waterfront amenities, including a marina, pool, and easy access to the beautiful waters of the Florida Keys. Conveniently located near restaurants, shopping, boating, and everything Islamorada and Tavernier have to offer. Whether you are looking for a full-time residence, vacation getaway, or investment opportunity, this charming Keys retreat is ready to welcome you home.

88500 Overseas Highway Unit 208, Tavernier
$3,450,000
4 Beds ⋅ 3 Baths ⋅ 620762 MLS
This exceptional waterfront estate situated on two lots and on a deep water canal with a 50ft dock is situated in the heart of Plantation Key. The property features a grand three story residence framed by established palm trees and a striking, patterned paver driveway. The expansive grounds are clean but unplanted, offering a clear blank canvas for you to design your ultimate custom tropical landscaping and privacy screening. The backyard focuses entirely on the water, featuring a lagoon style pool with cascading waterfalls, rock formations, and elevated sun decks. A private waterfront dock provides instant access to boating, fishing, or cruising to the open waters of Florida Bay. Inside, this well maintained home is incredibly clean and move in ready. The living spaces are generous and bright, with large windows that seamlessly connect to outdoor terraces overlooking the canal. Enjoy breathtaking, panoramic sunset views from the spacious rooftop observation deck, which provides vistas over the mangrove preserve and surrounding waterways. This property is perfect for someone looking for an immaculate, turnkey home with significant upside potential to add value and personality through their own landscaping vision. It offers the true keys lifestyle just minutes from world class fishing and attractions. This is more than a home; it is a true island destination.

168 Indian Mound Trl, Tavernier
$619,995
2 Beds ⋅ 2 Baths ⋅ 620555 MLS
Welcome to Futura Yacht Club! Your island getaway awaits in this highly desirable Plantation Key community. Unit 304 is a 2 bed, 2 bath, beautifully maintained condo. Florida Bay views make this third floor perch heavenly. A hideaway murphy bed is an additional feature adding to the desirability of this coastal condo as an ideal second home or rental. Owners and renters benefit from extensive community amenities, including a boat ramp, on-site boat and trailer storage, a large pool with adjacent club area, kayak storage, paddleball and basketball courts, and well-maintained grounds with shaded picnic spots. The on-site management team maintains the serenity of this community. This immaculate condo is being sold fully furnished. Futura is the place to be for boating, with short run times to the Ocean and Florida Bay. Easy boating and spectacular Florida Bay sunsets make for a beautiful investment in island living.

88540 Overseas Hwy Unit APT 304, Islamorada
$3,750,000
4 Beds ⋅ 5 Baths ⋅ 620543 MLS
Experience the ultimate Florida Keys waterfront lifestyle in this exceptional BayFront retreat located in the prestigious Sunshine Estates community on Plantation Key. Situated on a private 12,565 sq. ft. lot with 100 feet of pristine bay frontage and 50 feet of deep-water dockage, this contemporary CBS home offers breathtaking open bay views and quick ocean access via Tavernier Creek. Thoughtfully designed in a distinctive V-shaped layout to maximize privacy and showcase water views from nearly every room, the home features 4 bedrooms and 4 bathrooms, including 3 en-suite bedrooms. The spacious open-concept living area boasts soaring vaulted ceilings with exposed wood beams, recessed lighting, rich oakwood flooring, and elegant marble finishes throughout the bedrooms and bathrooms. Built-in shelving adds both style and functionality, while the oversized laundry room and pantry include a convenient dumbwaiter. The ground level is designed for entertaining, offering parking for up to four vehicles, a spacious recreation room, cabana bath, and summer kitchen that seamlessly blend indoor and outdoor living. Enjoy world-class boating, fishing, lobstering, paddleboarding, and water sports right from your backyard. Ideally located just minutes from restaurants, shopping, and schools, this home is approximately 40 minutes from the Florida Turnpike and perfectly positioned at Mile Marker 91. Whether you're seeking a full-time residence or a luxury Keys getaway, this remarkable waterfront property delivers the best of island living.

154 Redwing Rd, Tavernier
$599,000
2 Beds ⋅ 2 Baths ⋅ 620393 MLS
Welcome to coastal living in the heart of Islamorada! This beautifully appointed townhouse in the desirable Executive Bay Club offers comfort and resort-style amenities. The main level features an open-concept floor plan with a spacious living area and kitchen, plus full bath, creating an inviting space for entertaining and everyday living. Upstairs, you'll find an expansive primary suite, a generously sized guest bedroom and full bathroom, and a thoughtfully finished loft accessed from the hallway that serves as an ideal bonus sleeping area or home office. Step outside and enjoy the exceptional amenities that make Executive Bay Club one of Islamorada's most sought-after waterfront communities. Residents have access to the newly expanded first-come, first-serve dockage, a bayfront beach area, unforgettable sunsets, and a new heated swimming pool complete with an updated pool deck, clubhouse and bath facilities, pickleball and tennis courts, kayak storage and 24/7 staffed gated entry. Whether you're searching for a full-time residence, vacation retreat, or investment opportunity, this welcoming townhouse offers the ideal blend of island charm to enjoy the Florida Keys lifestyle.

87200 Overseas Hwy Unit D3, Islamorada
$609,900
2 Beds ⋅ 2 Baths ⋅ 620243 MLS
Experience the ultimate Florida Keys lifestyle in this bright and spacious townhouse-style condo located in sought-after Executive Bay Club in Islamorada. Ideally situated next to Founders Park, this gated bayfront community offers an unbeatable combination of location, lifestyle, and investment potential. One of the standout features of this residence is the rare open kitchen layout, creating a more spacious and inviting main living area ideal for everyday living or entertaining. EBC is highly desirable for boaters and investors alike, with first-come, first-served dockage available for boats, immediate bay access, and quick ocean access via Snake Creek and Tavernier Creek. Residents and guests enjoy a private sandy beach with beautiful sunset views, plus community amenities that include a renovated pool and clubhouse, tennis courts, pickleball courts, BBQ area, kayak launch, kayak storage, trailer parking, and secure gated entry. Short-term rentals are allowed with a 28-day minimum, making this an excellent opportunity for full-time living, a vacation getaway, or an income-producing property. Located in the heart of Islamorada and within walking distance to Founders Park events, recreation, and nearby dining, this property offers the ideal blend of waterfront enjoyment, boating convenience, and rental flexibility in one of the Florida Keys' most desirable communities.

87200 Overseas Hwy Unit APT A 7, Islamorada
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