Plantation Key Homes with Gulf Waterfront features

Plantation Key Homes with Gulf Waterfront features

Welcome to Plantation Key, a stunning gem nestled in the heart of the Florida Keys, within Monroe County. This picturesque island offers a unique blend of tropical beauty, laid-back charm, and vibrant community spirit, making it an ideal destination for those seeking a slice of paradise. With its lush landscapes, crystal-clear waters, and breathtaking sunsets, Plantation Key is a haven for nature lovers and outdoor enthusiasts alike.

One of the most alluring features of Plantation Key is its exquisite Gulf waterfront properties. Imagine waking up each morning to the soothing sounds of the waves and the gentle sea breeze, all while enjoying panoramic views of the shimmering Gulf of Mexico. Homes with Gulf waterfront access here are designed to enhance your coastal living experience, offering private docks, spacious patios, and expansive windows that invite the beauty of the outdoors inside.

Whether you’re looking for a cozy beach cottage or an expansive estate, Plantation Key has something for everyone. The real estate market here is as diverse as the island itself, providing options that cater to various tastes and budgets. Embrace a lifestyle filled with boating, fishing, and sun-soaked days on the beach, all while being part of a close-knit community that values tranquility and natural beauty.

With its idyllic setting and exceptional waterfront homes, Plantation Key is more than just a place to live; it’s a lifestyle choice. Come and discover the magic of this island paradise, where your dream home awaits!

Newest Plantation Key Homes with Gulf 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
$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
$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
$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
$13,900,000
6 Beds ⋅ 9 Baths ⋅ 620077 MLS
Yes, you can have it all! This one-of-a-kind 3.2 acre Islamorada bayfront estate offers a new boat dock, more than 250 feet of sandy wade-in bayfront shoreline, two full residences, a separate garage/media house and a move-in ready package of extras unlike any other property in the Keys. This remarkable compound captures the spirit of the Keys with a level of scale and exclusivity seldom found on the islands. Arrive through a private gate to discover a secluded retreat where every detail has been curated for relaxed coastal living. For boaters, the new boat dock offers immediate access to Florida Bay and immediate Atlantic Ocean access through nearby Snake Creek. The welcome package also includes a newer 34' Edgewater with twin 400 hp Yahamas, a pair of Waverunners and UTV tow vehicle, plus fishing rods, kayaks, paddle boards, and bicycles to enjoy everything Islamorada has to offer. The 100 ft. long resort-style pool with large spa create the centerpiece of the property, surrounded by multiple lounging areas, outdoor kitchen with covered bar, shady terraces and intimate gathering spaces. The estate's flexible layout includes two full homes--a 2/2.5 with ground level living, and a 3/3.5 tri-level--plus a 1/1.5 media house with 2-car garage, all with classic island character. Both homes offer chef kitchens with high-end appliances including SubZero and La Cornue. Not only is this estate ready for fun, it's also ready to enjoy with furniture, decor, kitchenware and even linens included! This remarkable property encompasses 2 acres of upland, 1.2 acres of baybottom, a separate buildable lot, plus valuable development rights. It is also conveniently located next to Islamorada's crown jewel Founder's Park for near instant access to seasonal festivals, sports fields, dog park, playground, tennis and pickleball courts and much more. All of these features elevate the property into a true legacy holding--ideal as a luxury residence, family compound, or private retreat.

139 Gimpy Gulch Dr, Islamorada
$635,000
3 Beds ⋅ 3 Baths ⋅ 619364 MLS
Welcome to effortless coastal living in the desirable Executive Bay Club community--where comfort, style, and resort-style amenities come together in a relaxed Keys setting. This nicely updated 3-bedroom plus loft townhouse offers a spacious and versatile layout designed for easy everyday living and entertaining. Upstairs, you'll find three inviting bedrooms, two full baths, and a charming loft--perfect for additional guests, a home office, or a cozy retreat. Downstairs, thoughtful updates create a seamless flow, with a level floor plan that connects the living and dining areas--no step-down interruptions--enhancing both function and openness. The expanded kitchen is a standout feature, showcasing stainless steel appliances, generous counter space, and a peninsula with double-sided storage, ideal for both cooking and gathering with friends and family. A full bath on the main level adds convenience for guests. Beyond your front door, Executive Bay Club offers an array of amenities to complement the coastal lifestyle. Enjoy two tennis and pickleball courts, newly expanded first-come, first-serve dockage for your boating adventures, and a beautifully renovated pool area complete with updated pool deck and bath facilities. The refreshed clubhouse provides an inviting space to relax and connect with neighbors. Whether you're seeking a full-time residence or a weekend escape, this welcoming townhouse delivers the perfect blend of elegance, comfort, and laid-back island living.

87200 Overseas Hwy Unit S3, Islamorada
$3,800,000
5 Beds ⋅ 3 Baths ⋅ 618165 MLS
Tired of waiting on Uber or Freebee? Why not make this stunning bayfront estate your own private slice of paradise, right in the heart of Islamorada? Just a flip-flop stroll away from local favorites like MEAT Eatery, Shima, Marker 88, and City Hall Café, this property places you at the vibrant core of island living. Behind its private, fully fenced grounds, you'll discover sweeping bay views and a rare tiki hut at the end of the dock—your new go-to spot for toasting unforgettable sunsets. Upstairs, the open-concept living area spills out through sliding glass doors onto a spacious, screened-in terrace, perfect for laid-back evenings or lively gatherings. This level also features three bedrooms and two baths, providing plenty of space for guests or family. Step down from the terrace to your own tropical oasis, complete with a pool, backyard, beach, and dock. The ground floor adds even more flexibility with two additional bedrooms, a bath, and a relaxed living area—ideal for guests or extended family. Whether you're looking for your forever getaway in the Keys or a smart investment when you're not soaking it all in yourself, this property is a rare find. Come see why life really is better by the bay.

87950 Overseas Hwy, Islamorada
$729,000
2 Beds ⋅ 2 Baths ⋅ 617897 MLS
Tropical Bayfront Condo - Futura Yacht Club, Islamorada. Welcome to your tropical getaway in the Florida Keys! This beautifully updated 2-bedroom, 2-bath condo is located in the highly sought-after, bayfront community of Futura Yacht Club in Islamorada. Perched on the 6th floor, the unit boasts panoramic views of both the Atlantic Ocean and Florida Bay--offering some of the most breathtaking sunsets in the Keys. Inside, you'll find a stylish, coastal-inspired interior featuring a modern kitchen with quartz countertops, stainless steel appliances, updated baths, and brand-new interior paint throughout. Hurricane shutters and tasteful furnishings make this residence both secure and turnkey. Step out onto your private balcony to enjoy the refreshing island breeze and sweeping water views. Futura Yacht Club is renowned for its resort-style amenities, including a heated pool, two tennis courts, pickleball, basketball, a sandy beach with lounge chairs, hammocks, a custom fire pit, kayak/paddleboard racks, and a clubhouse with an outdoor kitchen, bar, and TV--perfect for private gatherings. Boaters will love the onsite ramp, trailer storage, and available slip rentals with direct ocean access via Snake Creek. This pet-friendly, gated community also offers monthly rentals and has a strong history of repeat guests, making it ideal as a full-time residence, vacation home, or investment property. With a new roof in 2024, a passed milestone inspection, strong reserves, and low HOA fees that include many boating amenities, Futura truly delivers it all. Don't miss your opportunity to own a piece of paradise in one of the Keys' most versatile and well-equipped communities. Seller is licensed real estate agent with FKBOR.

88540 Overseas Highway Unit 605, Tavernier
$500,000
1 Beds ⋅ 1 Baths ⋅ 617483 MLS
Premier 1 bedroom unit a stunning open water and pool view off your private balcony. Fully updated with the open concept kitchen open to the dining and living room. Stunning white cabinets and modern bathroom, Tile floors and granite countertops throughout the apartment. Comfortable queen size bed with a pull-out couch in the living room. The perfect place to lounge and enjoy your days! The condominium is right on the bay with two pools (one heated), a beautiful beach area, Marina with a new composite Dock, Fish cleaning stations, Tiki huts with BBQ grills and picnic tables, Remodeled workout room and game room, community room, fabulous sunsets and friendly residential atmosphere. Safe and secure gated community with 2 brand new elevator. Summer Sea is a multi-story residential waterfront condominium with a friendly atmosphere with on-site management. The community has successfully completed its milestone inspection and continues to show pride of ownership with numerous recent improvements, including two new elevators, a new composite dock, newly remodeled poolside bathrooms, and storm rated windows -- all completed with no special assessments. This condominium is on Plantation Key, Tavernier at MM88.5, just north of the famous Marker 88 Restaurant, a 5-star gourmet restaurant with outside bar. Four restaurants within walking distance. Marina is first come, first serve, other restrictions apply. One pet per apartment with no size restriction. NOTE: The apartment is rented January, February and March 2027 so rental income is already in place!

88500 Overseas Highway Unit 320, Tavernier
$750,000
3 Beds ⋅ 2 Baths ⋅ 613083 MLS
All NEW NEXT TO MARINA & POOL Stunning Islamorada 3 full bedrooms 2 brand new bathrooms plus oversized loft with additional queen and three twin beds. This Townhouse has ALL NEW kitchen, new bar, new built-ins, new custom fishing closet & storage, brand new 4 ton AC unit, 2 brand new Bathrooms with showers, new extended loft area, new full size Washer/Dryer, new BBQ area with new patio chicago brick pavers plus private patio shaded area with beautiful palms trees, serena & lily furniture inside, new electric panel, new electric water heater, new 80' smart OLED TV, new area just for refreshments, coffee and bar, new 4 ton AC unit, high end hurricane impact windows and doors that are reflective and cannot see inside. New Electric car charging electric panel exclusive to this unit. Best area in the community next to pool and marina with two pickleball courts and basketball court in the rear. Sleeps easily over 10 people. King bed in the master bedroom, 2 queen mattress in additional bedroom and loft along with 5 twin mattresses. Rented in winter for over $6,500 a month! Call today! This community features a new private beach, marina, dock and clubhouse. Being SOLD fully furnished and fully equipped with high end appliances (FRIGIDAIRE), high end furniture (SERENA & LILY) and furnishings. See 3 Videos: https://youtu.be/P8cOME8P_kY; https://youtu.be/b6RmPMU8pvk; https://youtube.com/shorts/BEo0F_YzVFE;

87200 Overseas Hwy Unit V9, Islamorada
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