Plantation Key Real Estate

Plantation Key Real Estate

Welcome to Plantation Key, a captivating gem nestled in the heart of the Florida Keys, within Monroe County. This idyllic island community is renowned for its stunning natural beauty, vibrant local culture, and laid-back lifestyle, making it an ideal destination for both residents and visitors alike.

Surrounded by the crystal-clear waters of the Atlantic Ocean, Plantation Key offers an array of outdoor activities that cater to nature lovers and adventure seekers. Whether you’re kayaking through the mangroves, snorkeling in the coral reefs, or fishing in the abundant waters, the opportunities for exploration are endless. The nearby John Pennekamp Coral Reef State Park, the first underwater park in the U.S., is a must-visit, showcasing the breathtaking marine life that thrives in these waters.

Plantation Key is not just about its scenic landscapes; it’s also a community that embraces a rich cultural heritage. With a blend of charming local shops, delightful restaurants, and vibrant art scenes, the area fosters a sense of belonging and warmth. The annual events and festivals celebrate the unique spirit of the Keys, bringing residents together and inviting newcomers to join in the fun.

For those considering a move, Plantation Key offers a variety of real estate options, from cozy waterfront homes to luxurious estates, ensuring there's something for everyone. With its welcoming atmosphere, stunning surroundings, and endless recreational opportunities, Plantation Key is more than just a place to live; it’s a lifestyle waiting to be embraced. Come experience the magic of island living in Plantation Key, where every day feels like a vacation!

Newest Listings in Plantation Key

226 Navajo Street, Plantation Key
$4,350,000
4 Beds ⋅ 4 Baths ⋅ A12100206 MLS
Truly turnkey and fully furnished, this newly completed coastal-modern residence delivers approximately 3,100 square feet of refined luxury, with four bedrooms and four bathrooms. Completed in 2025 and professionally curated by Wright Interiors, the home showcases custom millwork, designer finishes and integrated technology, with impact glass and a sleek metal roof, a quality build by CBT Construction. Seamless indoor-outdoor living unfolds across a summer kitchen, outdoor bar, heated and chilled pool, lush tropical landscaping, and two climate-controlled garages, with elevator shaft ready for install. Approximately 60 feet of concrete dockage beneath custom composite decking is expertly configured for both a center console and skiff, with direct Florida Bay access, a 20,000-pound boat lift, shore power and custom fish-cleaning station. Positioned within one of Islamorada's premier close-knit boating neighborhoods, with A-rated schools nearby, this exceptional residence offers an elevated Keys lifestyle for both weekend escapes and full-time living. Optional HOA membership extends access to a private bayfront park and boat ramp.

226 Navajo Street, Plantation Key
179 Plantation Avenue, Plantation Key
$2,195,000
2 Beds ⋅ 2 Baths ⋅ A12085702 MLS
A Truly Unique Florida Keys Property — Location, Lifestyle & Luxury!This may be the perfect location and the perfect home for those looking for the ultimate Florida Keys lifestyle. Ideally situated in the Upper Keys, and a few houses away from the bay. The ocean is at a short ten minutes boat ride. This unique property is just over an hour from Miami and offers everything you and your family need to live comfortably, relax, and enjoy one of Florida's premier fishing paradises. The spectacular views from the kitchen, living room, and terrace are truly one of a kind. Imagine starting your morning with a cup of coffee while watching boats cruise through the canal, relaxing in the afternoon with a drink in hand, or entertaining family and friends as you take in the beautiful waterfront surroundings. After a day of fishing or a boat ride to one of the nearby ocean sandbars, unwind in the pool and enjoy the incredible Florida Keys lifestyle. It is truly picture-perfect. The owners have invested substantially in top-of-the-line improvements and upgrades throughout the property. Some of the most notable improvements include:Completely remodeled interiorAdded downstairs bathroom20,000-lb. boat liftPVC side fenceAluminum fencing in the front and rearWi-Fi-controlled electric gateSmart pool and spa controlsNew paver drivewayNew landscaping with artificial grass and natural rock paversNew interior and exterior A/C unitsNew supports and screening for the upstairs patioLarge fish-cleaning table at the dockNatural stone-paved dockDock storage boxDock electrical and water systemsNew foam-insulated roofIf you have been seriously considering purchasing a home in the Florida Keys, this property deserves your attention. From the exceptional location and breathtaking canal views to the extensive upgrades, pool, dock, and boat lift, this home offers an incredible opportunity to embrace the Keys lifestyle.Come see it for yourself. It may be the one you've been searching for.

179 Plantation Avenue, Plantation Key
87200 Overseas Highway Unit O10, Plantation Key
$625,000
2 Beds ⋅ 2 Baths ⋅ A12080867 MLS
Welcome to Boater’s Paradise!!! BAY ACCESS AND DOCKAGE AVAILABLE FOR BOATS UP TO 35" ON A FIRST-COME, FIRST-SARVED BASES. "CORNER"AND VERY PRIVATE TOWNHOUSE IN ONE OF THE MOST DESIRABLE GATED WATER FRONT COMMUNITIES IN ISLAMORADA. EXECUTIVE BAY CLUB. RECENTLY RENOVATED COMMUNITY POOL AND CLUB HOUSE. ENJOY 2 TENNIS COURTS, BBQ AREA AND KAYAK STORAGE. SHORT TERM RENTALS ALLOWED FOR 28 DAYS OR MORE MAKING IDEAL AS AN INCOME PRODUCING VACATION HOME.

87200 Overseas Highway Unit O10, Plantation Key
148 Giardino Drive, Plantation Key
$3,952,000
5 Beds ⋅ 3 Baths ⋅ A12078624 MLS ⋅ Venetian Shores BLDG.
THIS UPDATED BEAUTY LOCATED IN RENOWED VENETIAN SHORES IS A TRUE MUST SEE!! (1) UPSTAIRS: THREE BEDROOMS AND TWO SPACIOUS BATHROOMS!! COMFORTABLE LIVING ROOM AND DINING ROOM AREA WITH ACCESS TO A LARGE SCREENED IN PORCH WITH BEAUTIFUL WATERFRONT VIEWS!! LARGE KITCHEN WITH BEAUTIFUL CONNECTED ISLAND AND STATE OF THE ART COUNTERTOPS; MODERN APPLIANCES !! WET BAR AND WINE CELLAR CABINET!! INDEPENDENT INDOOR LAUNDARY ROOM WITH PLENTY OF STORAGE ! CUSTOM CLOSETS THROUGHOUT. HIGH END CEILING FANS THROUGHOUT THE ENTIRE HOME!! NEW EFFICIENT A/C!! (2) INDEPENDENT DOWNSTAIRS: TWO SPACIOUS BEDROOMS AND ONE BATHROOM, CUSTOM CLOSETS!! KITCHENETTE WITH MICROWAVE, REFRIGERATOR, SINK AND FILTERED WATER WITH LOTS OF STORAGE SPACE. LARGE SCREENED IN PORCH WITH GREAT WATERFRONT VIEWS !! (3) OUTDOOR ENTERTAINMENT FEATURES: 100 FEET OF WATERFRONT WITH UPDATED FLOOR DECK AND LIGHTING. THREE DOORS DOWN FROM SNAKE CREEK WITH EASY ACCESS TO BAYSIDE AND ATLANTIC. TWO BOAT LIFTS 14,000 LBS. AND 10,000 LBS. FISH CLEANING STATION WITH WATER AND POWER ACCESS. LARGE HEATED POOL (NEW POOL PUMP) WITH FIRE WATERFALL AND GAS FIREPIT OVERLOOKING THE WATERFRONT. OUTDOOR POOL SHOWER. GAS TIKI TORCHES AROUND THE POOL AREA !! FIVE HOLE PUTTING GREEN IS PERFECT FOR FAMILY ENTERTAINMENT !! ROOFTOP DECK WITH BEAUTIFUL VIEWS. (4)MISC: IMPACT WINDOWS/DOORS. ELECTRIC ROLLER SHUTTERS. ELECTRIC TESLA BATTERIES AND CAR CHARGER. ELEVATOR !! ONE GARAGE AND 2 STORAGE AREAS. FOUNDERS PARK !! RUN DONT WALK !!

148 Giardino Drive, Plantation Key
87200 Overseas Highway Unit E4, Plantation Key
$634,000
2 Beds ⋅ 2 Baths ⋅ A12054415 MLS
Discover Unit EBC-E4 at Excecutive Bay Club, a beautifully updated turnkey townhouse in the heart of Islamorada. Set in one of the community's most desirable locations, this private residence offers no parking directly in front, a quiet patio with lush tropical landscaping, and easy access to the bayfront sandy beach and pier for unforgettable sunsets. With 1.344 square feet of living space, the home features 2 bedrooms, 2 full bathrooms, and a flexible loft with room for two additional beds - Ideal for guests, family, or work -from-paradise setup. Fully furnished and equipped, it is ready to enjoy as a primary residence, vacation retreat, seasonal escape, or income-producing investment. Executive Bay Club offers resort-style amenities including a newly renovated heated bayfront pool, private sandy beach, upgrated clubhouse, tennis and pickleball courts,gated security, owner dock access, and a new community roof for added peace of mind.Adjacent to Founders Park and close to marinas, restaurants, beaches, nightlife, fishing,diving,kayaking, and snorkeling, Unit EBC-E4 places the best of the Florida Keys at your doorstep. Wheter you're seeking and island retreat, family getaway, or rental-friendly investment with monthly rental potential, this is a rare opportunity to own in one of Islamorada's most sought-after communities.

87200 Overseas Highway Unit E4, Plantation Key
251 Azalea Street, Plantation Key
$1,390,000
2 Beds ⋅ 2 Baths ⋅ A12020648 MLS
Located on a tranquil canal-front setting in the desirable Plantation Key Colony, this impeccably updated, turnkey ground-level residence offers two bedrooms, two baths, 50 ft of coveted dockage, and boat slip with immediate bay access. Meticulously maintained and ready for carefree island living. The home's concrete, ground-level construction enhances both durability and ease of maintenance, while a fresh, clean aesthetic unfolds inside and out. Recent upgrades and improvements include brand new metal roof, impact windows and doors, new interior and exterior paint, new interior doors, energy efficient appliances, new sewer line, and re-thatched tiki hut. Updates to the attached pull through garage includes new door rollers, lock hardware, and upgraded flooring and wall finishes, all designed to keep the property in turnkey condition. This home is for those who embrace water-based recreation with easy bay and ocean access via Tavernier Creek, a boat slip with ramp through the garage, and new fish cleaning station with electric and water hookup. The voluntary homeowners association offers a bayfront HOA park with a new boat ramp, beach, and picnic area. With its ideal location and exceptional features, this canal home presents a unique opportunity to embrace the vibrant lifestyle of the Upper Keys.

251 Azalea Street, Plantation Key
200 Wrenn Unit 502, Plantation Key
$399,000
1 Beds ⋅ 1 Baths ⋅ A11995992 MLS ⋅ The Sea Gulls BLDG.
Beautiful 1-bedroom, 1-bath condo at Seagulls Condominium in Tavernier with stunning ocean views. Fully furnished and ready to move in or rent. Enjoy resort-style living with pool, clubhouse, and game room. Convenient location close to local dining, shops, and all the beauty the Florida Keys have to offer. Perfect for vacation getaways or long-term rental investment.

200 Wrenn Unit 502, Plantation Key
87200 Overseas Highway Unit N2, Plantation Key
$630,000
2 Beds ⋅ 2 Baths ⋅ A11936246 MLS
Private location for your pleasure at this roomy townhouse offering an abundance of space to enjoy. Spiral stairs leading to the primary suites with an additional loft for your guests. Soft carpet on the living area floors with tile in the remodeled kitchen and beautiful bathrooms. Two pets allowed, with first come first serve the waterfront area. Pool and club house for your recreation along with a nice, landscaped community for your pleasure. 28-day rentals permitted. Garden setting from you extended living room to enjoy the outdoors at your back yard.

87200 Overseas Highway Unit N2, Plantation Key
125 Gardenia Street, Plantation Key
$1,750,000
4 Beds ⋅ 2 Baths ⋅ A11951326 MLS
Experience luxury waterfront living in the heart of the Florida Keys! 4 bedrooms and 2 bathrooms. This stunning modern home offers sleek finishes, breathtaking canal views, and direct boating access. Enjoy the spacious outdoor entertainment area, complete with a private dock, lush synthetic turf, and a large jacuzzi—perfect for relaxing under the stars. The upper-level terrace provides an ideal setting for lounging or hosting guests while enjoying the coastal breeze.

125 Gardenia Street, Plantation Key
87200 Overseas Highway Unit A7, Plantation Key
$609,900
2 Beds ⋅ 2 Baths ⋅ A12006598 MLS ⋅ A BLDG.
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 Highway Unit A7, Plantation Key
124 Orchid Street, Plantation Key
$2,849,000
4 Beds ⋅ 5 Baths ⋅ A11959736 MLS
Brand-new contemporary waterfront home in premier Plantation Key with 60 ft of protected deep-water dockage and seawall, offering direct canal access to Tavernier Creek, the Atlantic Ocean, and Florida Bay. Ground level features an open-air two-car garage and spacious covered area. First living level offers a large recreation room opening to the poolside patio with full cabana bath, perfect for entertaining and relaxed island living. Second level boasts a bright open-concept living and dining area and a gourmet chef’s kitchen with Italian cabinetry, premium finishes, and adjacent laundry room with sink and built-ins, all flowing to a covered waterfront terrace for seamless indoor-outdoor living. Third level showcases a luxurious primary suite with walk-in closet, spa-style bath with two-person shower, and private balcony overlooking the water, plus three guest bedrooms and a well-appointed guest bath. Outdoor amenities include a pool, covered terrace, and professional outdoor kitchen for year-round enjoyment. Ideally located in the Upper Florida Keys, close proximity to restaurants, a short boat ride to Tavernier Creek Marina for fuel, ice, and snacks, and minutes to boutiques, breweries, and 5-star dining in Islamorada—a rare blend of modern luxury and the ultimate Florida Keys waterfront lifestyle. SELLER WILL ENTERTAIN DESIRED REVISIONS OR OFFER CREDIT FOR UPGRADES.

124 Orchid Street, Plantation Key
87455 Old Hwy 229 Highway Unit 229, Plantation Key
$549,000
2 Beds ⋅ 2 Baths ⋅ A11928539 MLS
Beautifully maintained 2-bedroom, 2 bath townhouse condo located oceanside in the heart of Islamorada. This turn-key residence offers effortless island living with no updates needed—simply move in and enjoy. The home features a new A/C system installed in 2022, new appliances added in 2024, and fully replaced air ducts completed in 2024 for improved comfort and efficiency. Impact windows throughout provide security and storm protection, while electric blackout blinds add convenience and privacy.The interior is bright, clean, and exceptionally well cared for, making it ideal as a primary residence, vacation home, or weekend retreat. Situated in one of the most desirable areas of the Florida Keys, this property offers the perfect blend of comfort, style, and coastal living.Don’t miss the opportunity to own a truly turn-key condo in beautiful Islamorada. Schedule your showing today.

87455 Old Hwy 229 Highway Unit 229, Plantation Key
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