Plantation Key Homes with Ocean Front Waterfront features

Plantation Key Homes with Ocean Front Waterfront features

Welcome to Plantation Key, a hidden gem in the Florida Keys that perfectly embodies the laid-back island lifestyle. Nestled in Monroe County, this enchanting island offers a unique blend of natural beauty, vibrant culture, and a welcoming community. With its stunning oceanfront views and idyllic waterfront homes, Plantation Key is a paradise for those seeking a serene escape.

Imagine waking up every morning to the gentle sound of waves lapping against the shore, with the sun casting a golden glow across the turquoise waters. The homes here boast exceptional oceanfront features, allowing residents to immerse themselves in the breathtaking scenery that surrounds them. Whether you're sipping coffee on your private balcony or enjoying a sunset dinner on your patio, the ocean is always just a glance away.

Plantation Key is not just about beautiful homes; it’s a lifestyle. Residents enjoy a plethora of outdoor activities, from snorkeling and diving in the vibrant coral reefs to fishing in the abundant waters. The island is also home to charming boutiques, delightful eateries, and a rich tapestry of local culture that invites exploration and adventure.

With a strong sense of community and a commitment to preserving its natural beauty, Plantation Key is the perfect place to call home. Whether you’re searching for a vacation retreat or a permanent residence, the oceanfront properties here offer an unparalleled living experience, where every day feels like a vacation. Discover the beauty and tranquility of Plantation Key—your dream home awaits!

Newest Plantation Key Homes with Ocean Front Waterfront features

$999,988
3 Beds ⋅ 2 Baths ⋅ 621110 MLS
OCEANFRONT PENTHOUSE -- STRONG RENTAL INCOME. Welcome to PH701 at Sea Gulls, a rare and incredibly unique 3-bed, 2-bath oceanfront penthouse. With over 2,100 sq ft of living space and two expansive private balconies, this top-floor residence offers panoramic ocean views from every room. Offered FULLY FURNISHED and turnkey, this property has excellent rental income potential and is a high-performing investment. The open layout is light, breezy, and perfect for entertaining, complete with in-unit laundry. As one of just two penthouses in the building, PH701 provides exceptional privacy and prestige. Sea Gulls offers resort-style amenities including an oceanfront gym, heated seaside pool, kayak launch/storage, clubhouse, and secure access. Located in the heart of Tavernier near dining, shops, and schools, this penthouse combines luxury, income potential, and lifestyle flexibility. Don't miss your chance--schedule a private tour today!

200 Wrenn St Unit PH 701, Islamorada
$2,400,000
3 Beds ⋅ 4 Baths ⋅ 621073 MLS
Simply the best location, exclusive & extremely private. This is a rare find and a single-family home that's rarely available. It's tucked away in the prestigious ''Plantation Lake Estates,'' a highly sought-after gated community with an on-site boat ramp and park. This Coastal-Styled Beach Home is in a prime location at Mile Marker 87, across the street from Founders Park, which has a beach, tennis courts, a full-service marina, a dog park, sports fields, and Olympic-size lap pools. This home boasts a stunning great room with a gorgeous coral fireplace and soaring wood beam ceilings. They all overlook the glistening Atlantic Ocean, providing priceless views and sunrises. The home has a metal roof, a modern kitchen, updated baths, and impact windows and doors. The exterior has been reinforced with rebar and stucco. There are three inviting bedrooms, including a third-floor master en-suite with a private porch. A large ''rec room'' with a cabana kitchen is perfect for indoor-outdoor entertaining. You'll have world-class fishing and diving right in your own backyard.

316 North Dr, Islamorada
$1,300,000
2 Beds ⋅ 2 Baths ⋅ 621009 MLS
A New Standard of Paradise - Live with views of the Atlantic Ocean everyday. This home has been updated and beautified from top to bottom. Marble flooring throughout living areas. Eat in kitchen offers large island, snack counter and full size wine cooler. Dishwasher installed 12/25. There is also a hot water dispenser. Dining area and living area open to enclosed patio with private spiral staircase leading to resort styled amenities. Impact glass on all windows. Primary bedroom offers more spectacular views, built in furnishings and is 14x14. Modification in primary bathroom leads to large walk in closet. Washer replaced 2025, dryer 2024, AC 2021. Building inspections complete with no pending assessments. Private Marina dredged 2025. Outside storage cage included. RARE covered parking. Enjoy resort style pool, hot tub, tennis, pickleball, nature trails, gazebos, boat ramp, clubhouse with fitness, pavilion with ice machine, docks rentable for up to 30ft boat (almost always available), tiki huts, electric vehicle chargers, guest parking, open lot for boat storage, and private marina. Chandelier in dining area excluded. Beach area overlooks marina. Owner agent.

87851 Old Hwy Unit APT M5, Islamorada
$427,000
2 Beds ⋅ 2 Baths ⋅ 620997 MLS
BEAUTIFUL CONDO WITH OCEAN VIEWS FOR LESS THAN $430,000! LIVE THE DREAM IN THIS OCEANFRONT RESORT STYLE PROPERTY IN THE HIGHLY DESIRABLE PLANTATION BY THE SEA ON THE OCEAN IN THE BEAUTIFUL FLORIDA KEYS! LOCATED ON HIGHLY SOUGHT AFTER MILLIONAIRES ROW! UPON ENTERING THIS GATED COMMUNITY, THE OCEAN GREETS YOU AS YOU PARK IN YOUR DESIGNATED COVERED PARKING SPACE. UPON ENTERING YOUR CONDO, THIS PARTIALLY UPDATED CONDO WITH OPEN CONCEPT KITCHEN, WELCOMES YOUR HOME TO A CHEF'S DREAM KITCHEN WITH PLENTY OF CABINET SPACE. NEW WATER HEATER, SCREENED IN PATIO ON THE FIRST FLOOR AND GORGEOUS OCEAN VIEWS FROM THE SECOND FLOOR. CLUBHOUSE/COMMUNITY ROOM, FITNESS ROOM, SAUNA, KAYAK STORAGE, LONG AND WIDE FISHING PIER/DOCK ALLOWS YOU TO TIE UP YOUR BOAT FOR LOADING AND UNLOADING WALK TO WORLD CLASS RESTAURANTS, SHOPPING, AND FOUNDER'S PARK. ALL ARE CLOSE! TAKE ADVANTAGE OF THIS AMAZING OPPORTUNITY TO LIVE FULL TIME WHERE OTHERS VACATION, OR START A VACATION RENTAL BUSINESS HERE IN THE BEAUTIFUL FLORIDA KEYS!

87455 Old Hwy Unit 248, Islamorada
$795,000
2 Beds ⋅ 3 Baths ⋅ 620945 MLS
Island Opportunity is knocking! Enjoy your own Islamorada vacation home...with the option to generate excellent rental income when you're not using it. Set in a private, peaceful oceanfront community of just 10 townhomes, you'll have a beach, pool and your own slip for boat up to 30'. Spend the day on the water, relax by the pool or head up to the rooftop deck for ocean breezes & a peekaboo water view. There are four balconies - so you can enjoy some shade at any time of day. Although this seller never rented, the home is eligible for a coveted weekly rental license, giving a new owner the flexibility to enjoy it personally while also taking advantage of the strong Keys vacation rental market. The 2 bedroom, 2.5 bath townhome has a comfortable layout, with a private bath for each bedroom, a half bath on the main living level, and *straight interior* stairs rather than a spiral staircase. It's also refreshingly low maintenance, with concrete construction, a concrete roof, impact windows and doors, and an HOA that takes care of the grounds. Because this is a townhome rather than a condo, owners choose how much insurance to carry, and current insurance costs are surprisingly low. It's even in an X flood zone, so no flood insurance is required. Covered parking and an entry from underneath the home are two more practical touches that make coming and going easy, rain or shine. Trailer/boat storage is allowed under the home. The location works just as well by water as it does by land, with fantastic fishing and diving just steps from home and a great Old Highway location close to Founders Park, restaurants and everything you come to Islamorada to enjoy. Breezy and relaxed when you're here, with the ability to generate income when you're not. It's a rare and excellent combination.. good for your heart and your wallet.

136 Aregood Ln, Islamorada
$6,000,000
4 Beds ⋅ 6 Baths ⋅ 620708 MLS
Coastal Luxury. Endless Lifestyle. A rare opportunity to own an extraordinary Plantation Key waterfront estate where captivating ocean views, 140 feet of protected dockage, direct Atlantic access, and exceptional craftsmanship come together in perfect harmony. Privately tucked away on a quiet cul-de-sac, this stunning coastal residence was thoughtfully designed for those who appreciate effortless luxury both on and off the water. Filled with natural light, the open-concept floor plan showcases soaring ceilings, walls of glass, and seamless indoor-outdoor living that frames beautiful water views throughout the home. At the heart of the residence, the gourmet chef's kitchen is beautifully appointed with premium appliances, including dual ovens, two dishwashers, generous preparation space, and an oversized island that effortlessly connects the living and dining areas, creating the perfect setting for entertaining family and friends. Step outside to an expansive covered terrace complete with a built-in barbecue, outdoor refrigerator, and multiple gathering spaces overlooking the resort-style saltwater pool and spa, lush tropical landscaping, and tranquil waterfront. Whether hosting sunset cocktails or enjoying a quiet morning coffee, every space has been designed to embrace the relaxed elegance of the Florida Keys. The thoughtfully designed floor plan offers four spacious bedrooms, four full baths, two half baths, a private elevator, and a luxurious primary suite featuring separate his-and-her walk-in closets. A spacious secondary living area, currently enjoyed as a waterfront fitness studio, offers endless possibilities as a media room, family room, home office, or guest retreat. For boating enthusiasts, this property is truly exceptional. Boasting 140 feet of protected dockage, a boat lift, five garages with direct canal-side access, and quick, easy access to the Atlantic Ocean, it is perfectly suited for everything from offshore fishing adventures to leisurely days on the water. Surrounded by beautifully established tropical gardens with irrigation and meticulously maintained grounds, this remarkable waterfront estate offers the perfect balance of privacy, sophistication, and relaxed coastal living

202 Plantation Shores Dr, Tavernier
$8,500,000
620668 MLS
BUSINESS INCLUDED: Very Profitable Marina & Unique Resort in Islamorada, FL. 2025 NET Income reported over $800,000/yr. !! Offered at over 9.5% Cap rate at Asking Price. Manager on site handles responsibilities with oversight from the absentee owner. Rare 1+ Acre Oceanside Lot with many uses possible. Deep water protected harbor with 18 large boat slips that can accommodate 50+ ft. yachts. Approach depth approximately 6 ft.+ at high tide with a clearly marked channel. Successful Boat Rental Business with 17 boats included in the sale. Lucrative Vacation Rental Business with (10) Aqua Lodges and 1 houseboat also included. Features include water, new 30 Amp and 50 Amp electric at each slip, fuel dock, concrete building with office, ship store, workshop, and garage/storage. 2 outdoor showers, 2 bath houses with indoor showers, stalls, and dressing area. New waste/pump-out station and fuel station. An additional separate concrete building used for storage on the North side of the property. New Concrete In-ground Pool, Deck and Fence just completed. Brand new floating docks. Private marina, must call for an appointment and sign an NDA/CA for more information.

200 Treasure Harbor Dr, Islamorada
$1,950,000
4 Beds ⋅ 3 Baths ⋅ 620649 MLS
Welcome to Ocean Harbour, one of Islamorada's premier communities! This unique 4 Bedroom, 3 Bathroom expansive 2668sqft condominium offers a desirable split floor plan with an open kitchen, dining room and living area, impact windows and doors, new a/c and water heater along with an enclosed air-conditioned porch, all overlooking breathtaking views of the Atlantic Ocean. Enjoy the convenience of a private rear entry staircase leading directly to your 50' boat slip (#27), nestled in the expansive marina. Additional perks include storage room and covered parking. Set on 12 acres of lush tropical grounds, Ocean Harbour offers endless amenities including a heated swimming pool, hot tub, sandy beach, boat ramp, trailer storage, tennis and pickleball courts, clubhouse, and a fitness center with ocean views. Enjoy nearby Florida Bay access through Snake Creek offering offshore or backcountry fishing and numerous delicious waterfront restaurants. This property truly offers the best of Keys living!

87851 Old Hwy Unit P3, Islamorada
$3,995,000
5 Beds ⋅ 4 Baths ⋅ 620430 MLS
Discover a rare opportunity to own an exceptional oceanfront estate in the heart of Islamorada that seamlessly combines luxury living with an established, successful vacation rental history. Situated on 1.82 private acres with approximately 225 feet of ocean frontage, this Residential Estate-zoned property is currently licensed for legal 7-day vacation rentals, making it one of the limited number of properties within the Village of Islamorada offering this highly sought-after privilege. With a documented history as a successful income-producing vacation rental, this property offers the opportunity to enjoy an extraordinary Florida Keys lifestyle while rental income may help offset the costs of ownership. A gated entrance welcomes you through a majestic Royal Palm-lined circular driveway to an impressive, covered portico. Inside, a dramatic foyer and elegant wrought-iron staircase set the tone for a home featuring five spacious bedrooms, four beautifully appointed bathrooms, and breathtaking ocean views throughout. Enjoy spectacular sunrises from the observation pier or relax year-round in the heated and chilled saltwater pool. The home is beautifully appointed with quartz countertops, premium appliances, impact-resistant windows, and exceptional craftsmanship throughout. Whether you're seeking a luxurious private residence or a proven income-producing property to help offset costs, this ideal combination of both is a remarkable Islamorada estate that offers an exceptional blend of privacy, oceanfront beauty, and one of the most desirable licensed weekly vacation rental opportunities in the Florida Keys.

87445 Old Hwy, Islamorada
$1,595,000
620208 MLS
DIRECT OCEANFRONT LOT IN ISLAMORADA WITH ACTIVE BUILDING PERMIT! A rare opportunity to own a beautifully situated direct oceanfront parcel in the heart of Islamorada, offering breathtaking panoramic views of the Atlantic Ocean. An active building permit is already in place, allowing you to begin construction of your dream waterfront estate immediately, or take advantage of the Village of Islamorada's available two-year permit extension. This spacious homesite includes a mangrove height reduction permit, allowing the mangroves to be trimmed to six feet. Upon completion, the property will enjoy unobstructed ocean views at ground level, creating an exceptional setting for luxury coastal living. Enjoy direct ocean access with convenient nearby Florida Bay access via Snake Creek, as well as close proximity to dry-dock marina facilities. Potential exists for an observation deck and/or dock, further enhancing the property's appeal and maximizing the spectacular waterfront setting. The elevation rendering is conceptual and provided for illustrative purposes. Utilize the approved plans currently in place or modify them to create a custom residence tailored to your vision. Opportunities like this are increasingly rare--build your dream home and experience the unparalleled beauty, boating, fishing, and island lifestyle that make the Florida Keys so desirable.

229 Coral Rd, Islamorada
$13,500,000
8 Beds ⋅ 8 Baths ⋅ 620067 MLS
Private Helicopter Estate in the Florida Keys. Behind private gates on prestigious Million Air Row, this exceptional oceanfront estate spans nearly 2.5 acres and offers a rare blend of luxury, privacy, and future potential. The recently renovated residence features 8 bedrooms, 7.5 bathrooms, double-height ceilings, spacious bedroom suites, abundant storage throughout, solid CBS construction, impact windows and doors, and a new concrete roof. Designed for the ultimate Florida Keys lifestyle, the property boasts protected basin dockage with a 24,000 lb boat lift, a private helicopter pad, hot yoga studio, resort-style pool with waterslides, waterfall, and spa, plus two covered carports and a large garage. Expansive grounds provide endless opportunities to add additional amenities such as pickleball, volleyball, guest accommodations, or a private beach retreat. A truly unique waterfront compound offering the space and exclusivity rarely found in the Florida Keys.

89401 Old Hwy, Tavernier
$26,400,000
7 Beds ⋅ 10 Baths ⋅ 620022 MLS
Escape to Palm Paradise, a breathtaking oceanfront estate on 7.64 private acres in Islamorada, offering 369 feet of shoreline and sweeping Atlantic views. Tucked behind gates on Plantation Key, this secluded retreat combines lush tropical landscaping with unmatched privacy for the ultimate island escape. The 8,988-square-foot main residence showcases exceptional craftsmanship and thoughtful design. One wing features a dramatic two-story primary suite with a private office, while the opposite wing includes four additional bedrooms and four bathrooms across two levels. A separate two-bedroom guest house provides extra space for visitors, and a whole-house generator adds convenience and peace of mind. Inside, custom woodwork, coffered ceilings, built-ins, and high-end finishes create a warm yet refined atmosphere. Amenities include a chef's kitchen, wine cellar, private gym, elevator, and seamless indoor-outdoor living spaces ideal for entertaining or relaxing by the water. Resort-style outdoor features include a custom pool, tiki bar, outdoor kitchen, beachside fire pit, putting green, observation pier, and a lighted tennis court with cabana. Convenient access by seaplane, helicopter, or a 90-minute drive from Miami makes travel effortless. Perfect for boating enthusiasts, the estate is near dockage and concierge dry storage options. Located in the heart of Islamorada, Palm Paradise offers easy access to world-class fishing, boating, dining, and the laid-back luxury of the Florida Keys. Offered at $26.4M, Palm Paradise is a rare opportunity to own a private waterfront compound ideal for luxury living, family retreats, or executive escapes.

89505 Old Hwy, Tavernier
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