Divider
Content Divider

Plantation Key Waterfront Homes For Sale on the Ocean Side

Most of the properties in the Florida Keys peninsula are either on the ocean side or on the bay / gulf side of the island. The following Waterfront Plantation Key homes for sale below are on the ocean side.

Total Listings 16
Order By:

$1,690,000
Plantation Key
Venetian Shores   - MM: 86.00
3 Bed, 3 Baths, 1,568 SqFt Days Listed: 132
-13.33% ($260,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 70ft.

Venetian Shores location for under $2M! This spacious and solid concrete house has an excellent location right off Snake Creek for fast access to both Ocean & Bay, fuel, bait and provisions. Enjoy 70 of commercially zoned dockage in the best Islamorada location available! Upstairs features an open floor plan with gourmet kitchen and breakfast bar, office area, bonus room, roomy bedrooms and two full bathrooms. Downstairs guest suite with bathroom & kitchen plus screened patio to access the outside tiki hut and nice outdoor living on the canal.

$1,800,000
Plantation Key
Tropical Atlantic Shores   - MM: 90.00
4 Bed, 4 Baths, 2,422 SqFt Days Listed: 88
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Boat Lift70ft

A boaters dream location in Tavernier! Tropical Atlantic Shores ~Solid concrete including the roof, this residence offers unparalleled direct access to the Atlantic Ocean, with immediate entry to Tavernier Creek and Florida Bay--a dream location for boating enthusiasts. Within minutes, reach Islamoradas pristine waters, renowned coral reefs, and legendary fishing grounds.This beautifully remodeled and updated residence features four bedrooms and three baths, thoughtfully arranged with a 2BD/2BA up on main level and a 2BD/1BA lower level is permitted and pre-firm.Designed for both comfort and functionality, 70 concrete dock with 14,000 lb boat lift and davits for seamless boatingScreened-in canal-side porch, perfect for relaxing and soaking in the waterfront viewsGorgeous tongue-and-groove ceilings and pristine polished terrazzo flooringImpact-resistant doors and windows for safety and energy efficiencyGourmet kitchen with custom cabinetry, quartz countertops, soft-close drawers, built-in microwave/oven, and stainless-steel appliances, including a panel-covered dishwasherTumbled marble backsplash, adding a refined touch to the kitchens sophisticated aestheticDining area with a custom butcher block bench, offering ample built-in storageSet on an expensive 8,050 sq. ft. lot, this home offers space to add a pool or create your backyard oasis. Whether youre a boating enthusiast or seeking the tranquility of island living, this extraordinary property is a rare opportunity to own a piece of paradise.Beyond the water, indulge in the best of onshore living with an array of fine dining options, a nearby grocery store, a movie theater, and a hospital--all within close reach. This home embodies the essence of Florida Keys, Tavernier, and Islamorada lifestyle.Dont miss out--schedule your private tour today!

$1,950,000
Plantation Key
Tropical Atlantic Shores 1st   - MM: 90.00
3 Bed, 3 Baths, 2,364 SqFt Days Listed: 143
-7.14% ($150,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 70ft.

Fishermans Delight! This concrete fortress is nestled in a lush tropical setting, located on the Oceanside on a deep, clean, wide canal. 70 concrete dock accommodates larger boats. Solidly built CBS construction with reinforced concrete roof. Spacious rooms and living areas throughout. The first floor features a guest quarter with separate entrances, seller has set up as two apartments. Take the stair lift upstairs to the generous sized rooms and a large balcony overlooking a custom built zero entry inground pool and spa surrounded by custom murals. Newly thatched Tiki entertainment area. Direct ocean access and easy bay access through Tavernier Creek. Completely fenced for privacy. Close to schools grades K-12, shopping, restaurants, and easy commute to Miami or Marathon. Potential for adding bedroom and bath. Shown by appointment. Best boating in the Upper Keys.

$2,285,000
Plantation Key
Fontaine Lake   - MM: 90.00
3 Bed, 3 Baths, 2,669 SqFt Days Listed: 53
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Custom Waterfront Pool Home! Offering teak wood floors and doors, 16 vaulted ceilings, custom crown and baseboard molding, chefs kitchen with 6 burner Viking gas range and stainless steel appliances.The home is situated on 2 mature landscaped lots with new irrigation system, free form pool with spill-over spa and resurfaced with Diamond Brite coating, new pool heater, chiller and pump including system control for wifi app, expansive patio with stone decking, fire pit and outdoor shower.The home has been well maintained with new tankless water heater, extensive water sealer and barrier to the crawl space under the house, 22 kw Generac generator enables the entire house to function. Concrete dock with permit in place for extended dockage (please see documents for current permit) The harbor provides immediate ocean access.Truly a beautiful traditional family home!

$2,995,000
Plantation Key
Plantation Shores   - MM: 90.00
4 Bed, 4 Baths, 2,970 SqFt Days Listed: 59
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

EXQUISITE OCEAN VIEW POOL HOME! Welcome to Tuts Cay, a luxurious 4 bedroom, 5 bathroom, a sanctuary in The Village of Islamorada, Florida Keys. This property spans on two lots, offering stunning ocean views and privacy. The resort-style pool area includes an outdoor kitchen and golf putting green, perfect for relaxation and entertaining. Boating enthusiasts will appreciate the ample dockage and nearby community boat ramp. Inside, enjoy sophisticated living areas with en-suite bathrooms for each bedroom plus a pool bath. The residence features televisions in every room, large balconies, dual kitchens, and a wet bar. Exterior amenities include a rooftop lounge, private pool and hot tub, sun loungers, hammock, outdoor bar, mini fridge, built-in grill, and firepit. Tuts Cay blends luxury, convenience, and natural beauty for an unforgettable vacation or full time home. Located in the Sports Fishing Capital of World!

$3,225,000
Plantation Key
Venetian Shores   - MM: 86.00
4 Bed, 4 Baths, 2,478 SqFt Days Listed: 40
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Boat Lift70ft

LOOKING FOR THE PREMIER DEEP WATER OCEAN/BAY ACCESS COMMUNITY? Discover the epitome of waterfront living in the exclusive community of Venetian Shores in Islamorada. Renowned for its expansive 100-foot-wide canals, this neighborhood provides unparalleled access to both the Atlantic Ocean and Florida Bay via Snake Creek--ideal for boating enthusiasts. This meticulously updated residence boasts 4 spacious bedrooms and 4 bathrooms. The upper level features three en-suite bedrooms, ensuring privacy and comfort for all occupants. The main living area is highlighted by soaring tongue-and-groove vaulted ceilings and 8-foot impact-resistant French doors that open to a screened lanai overlooking the saltwater pool and canal. The gourmet kitchen is equipped with stainless steel appliances and a gas stove, catering to culinary enthusiasts.The ground floor offers a legal apartment complete with a bedroom and full bath, perfect for guests. Entertain effortlessly on the expansive covered porch, which provides a serene setting to enjoy the outdoors.The saltwater pool is designed for year-round enjoyment, featuring both heating and cooling capabilities, along with a retractable cover for added convenience. A dedicated, air-conditioned mancave offers ample space for storing boating, fishing, and diving equipment. For boating aficionados, a 20,000-pound boat lift was installed, and the property is fully fenced with a sliding gate, ensuring privacy and security.With nearly $80,000 invested in recent improvements, this home is move-in ready. Embrace the Florida Keys lifestyle with world-class fishing and diving just minutes away. Dont miss the opportunity to own this exceptional waterfront property-- Your Florida Keys Dream Home Awaits!

$3,249,000
Plantation Key
Plantation Tropical Park   - MM: 91.00
3 Bed, 3 Baths, 2,938 SqFt Days Listed: 107
-9.49% ($340,800) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Assigned Dock60ft.

This brand-new tri-level home in the FL Keys perfectly captures the essence of sophisticated luxury & relaxed island living. With both bay & ocean access, 60 ft. of canal frontage + private concrete dock, its ideal for saltwater enthusiasts. The home flows seamlessly from the rec room & summer kitchen to pool area, all set in a fenced yard - perfect for kids & pets. The 2nd level offers open living & dining, kitchen island, sleek wet bar & laundry room. An expansive balcony is perfect for family dinners & unwinding. Upstairs, elegant finishes & water views offer a peaceful master retreat. Just blocks from Tavernier Marina & fuel station, close to the top dining spots in Islamorada & only 90 mins. from Miami, this home is an ideal vacation retreat w/no HOA & great rental income potential.

$3,275,000
Plantation Key
Plantation Lake Estates   - MM: 87.00
4 Bed, 4 Baths, 2,782 SqFt Days Listed: 55
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Located in a private, gated community in the heart of Islamorada, 109 South Drive is a rare waterfront retreat that perfectly blends luxury, comfort, and the ultimate Florida Keys lifestyle. The main home features 4 spacious bedrooms and 3.5 beautifully designed bathrooms upstairs, while a separate 1-bedroom, 1-bath apartment downstairs offers privacy for guests or rental potential. Enjoy a custom resort-style pool surrounded by lush, tropical landscaping and a brand-new designer kitchen by Allabastro Designs. Boaters will appreciate the protected dockage with an ipe dock and direct ocean access -- no bridges, no long idle canals. Relax on the rooftop balcony with panoramic ocean views or entertain on expansive outdoor patios. With its unmatched access, thoughtful upgrades, and serene island ambiance, this property is a true Islamorada gem.

$4,995,000
Plantation Key
Plantation Beach   - MM: 87.50
5 Bed, 5 Baths, 4,014 SqFt Days Listed: 225
-20.65% ($1,300,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

This stunning property spans 1.82 acres and is ideally located on the ocean in the heart of Islamorada, Florida Keys. A gated entry welcomes you leading to a Royal Palm-lined circular driveway up to a portico providing a grand entrance. Upon entering the foyer, the wrought iron staircase sets the stage for the impressive interior.With five spacious bedrooms and four well-appointed bathrooms, this residence offers ample space for family and guests. Enjoy stunning ocean views from various vantage points within the home, enhancing the comfort and breathtaking natural beauty. The observation dock provides a perfect spot for relaxation, while the saltwater pool equipped with heater/chiller, ensures year-round enjoyment. Added features are quartz countertops, top-of-the-line appliances and the Residential Estate zoning allows weekly vacation rentals with a high-income stream.This combination of amenities creates an inviting atmosphere that reflects the privacy and charm of the Florida Keys lifestyle.

$6,950,000
Plantation Key
Treasure Harbor   - MM: 86.50
4 Bed, 4 Baths, 3,790 SqFt Days Listed: 117
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Southern Shore - A Modern Coastal Masterpiece Nestled in an exclusive oceanfront setting, Southern Shore is a premier coastal residence offering an unobstructed, 180-degree panorama of the Atlantic Ocean. This exceptional, all-concrete estate spans 3,790 square feet of meticulously designed indoor living space, complemented by 2,580 square feet of expansive terraces for seamless outdoor living. Inside, the home features four luxurious en-suite bedrooms, offering breathtaking ocean views. The chef-inspired kitchen is outfitted with custom floor-to-ceiling cabinetry, sleek quartz countertops, and top-of-the-line appliances. State-of-the-art smart home technology, custom-built closets, and the convenience of an elevator elevate both form and function in this sophisticated residence. The interior spaces reflect a perfect balance of elegance and comfort. With floor-to-ceiling windows throughout, the home captures the essence of the tropical lifestyle, offering stunning vistas of the ocean from nearly every room--living areas, kitchen, and bedrooms alike. The outdoor spaces of this estate are designed to host gatherings in style, featuring a rooftop deck, multiple terraces, and a luxurious pool and spa area with an outdoor shower. For boat enthusiasts there is a 12K lift boat and letter from the Village Planning and Building Department allowing a 24K 4 post lift. All protected by a gated entry. Located within the serene Plantation Key community, this property also includes a misting system and occupies an expansive lot with direct ocean access. This is the ultimate tropical sanctuary for those seeking a premier location with unparalleled views, superior construction, and a full suite of luxurious amenities. Note: The owner is a licensed Florida real estate agent. For additional details, please refer to the full property description available in the document tab.

$7,000,000
Plantation Key
Key Heights   - MM: 88.50
3 Bed, 3 Baths, 1,728 SqFt Days Listed: 229
+4.48% ($300,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Boat Lift

Discover your dream retreat in this beautiful oceanfront home, set on 1.5 acres of prime beachfront property with 150 feet of pristine white sandy beach, this is the ultimate getaway for relaxation and adventure.Unwind in the oversized heated pool or customized hot tub after a day of sun and fun. The Tiki Hut provides convenient storage for all your water toys, making your boating and beach days effortless. Enjoy practicing your swing on the private putting golf course, all while surrounded by breathtaking ocean scenery.With a lucrative 7-day rental option and an easily obtainable license, this gem is perfect for both personal enjoyment and investment. Dont miss your chance to own this slice of paradise--schedule a viewing today!

$7,500,000
Plantation Key
Key Heights   - MM: 88.50
4 Bed, 4 Baths, 4,103 SqFt Days Listed: 334
+15.38% ($1,000,000) 1 Price Change : Last Change 13 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift400ft.Concr

Open Oceanfront Estate with Deep Water Dockage on 1.5 Acres on Millionaires Row... Islamoradas premier address. New dock with two boat lifts (16,000 lb. and 10,000 lb.) to enjoy one of the best boating locations in the Keys, plus a 4,103 s.f. home with 4 bedrooms, 3 full baths, a large heated pool, winding private driveway, and a soaring central atrium surrounded by walls of windows to frame the ocean view. Open ocean views from the living room, Florida room, porches, master bedroom and upstairs loft. Living room with wet bar and pass-through window to the gourmet kitchen and separate dining room, all with Saturnia stone floors. Direct boating access to the best offshore fishing and diving, plus quick Florida Bay access. RE Zoning allows weekly rentals for great income potential. The sandy backyard is shaded by palms and the large pool is fenced for privacy. The winding drive from the gate to the home is dotted with seating spots for enjoying the wildlife and tropical foliage. There is also a separate storage room and workshop downstairs, a gardening shed and landscape lighting along the driveway. Call today!

$11,000,000
Plantation Key
Treasure Harbor   - MM: 86.50
6 Bed, 6 Baths, 7,160 SqFt Days Listed: 163
-7.56% ($900,000) 1 Price Change : Last Change 24 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Boat Slip3

Modern luxury meets barefoot elegance in this oceanfront masterpiece in Islamorada! Stunning ocean views can be seen from almost every room in this spectacular home. Designed for casual living and entertaining, indoor and outdoor living is seamless and allows for year round enjoyment of the Florida Keys lifestyle. Open ocean views, 380 ft. of dockage with power and water and a cut in boatslip with a 25,000 lb. boatlift will accommodate your boats and water toys. Boasting 6 bedrooms, each with ensuite baths, a 3 story elevator whisks you from the ground level to the main living level on the second floor. Here you will find an open floor plan accented with high coffered ceilings and tall windows and doors opening to ocean views. The kitchen has a large island with quartzite counters and a waterfall edge, GE Monogram appliances and walk in pantry. The primary suite offers ocean views, his and hers closets and a magnificent bath with a double vanity, free standing tub and ingenious double shower. There is a junior primary suite on this level with its own breakfast bar and refrigerator. The game room is on the 3rd floor with exceptional ocean views, service bar and 600 bottle wine vault! Also on this floor are 4 guest bedrooms with ensuite baths. This oceanfront oasis is gated for privacy and features a 3 car garage plus an additional single car garage! The pavered driveway leads to the front door and entrance foyer where you see the pool and oceanfront beauty shining through. To the left is the gym to work off last nights dinner and the pool deck and dock are straight ahead ready for some fun today. There is plenty of shade by the outdoor kitchen or you can relax on the oceanfront chaises. The pool with sun shelf and spa are ready for your friends and family to enjoy. Need a little extra shade? An oceanfront tiki sits beside a fire pit for the perfect transition from day to night! Tiki torches along the waterfront are the perfect evening accent!

$12,500,000
Plantation Key
Trop Coral Reef   - MM: 89.00
3 Bed, 3 Baths, 1,243 SqFt Days Listed: 16
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 200ft.

Pure magic. Every step on this property is like a step back in time. Once you pass through the gated coral rock entrance you are instantly transported back to the Old Keys as you wind down the driveway through the shady tropical hammock and meander your way to the settlers beach home circa 1934. The charming 3/3 fishing cabin was meticulously updated to add modern comforts but still maintain its relaxing Old Florida appeal. The kitchen, living room and primary bedroom all enjoy open ocean views and all three bedrooms are ensuite. Just sitting on the shady back porch, enjoying the hush of the palms, you could mistake this breathtaking oceanfront for a postcard of yesterdays Florida Keys a century ago. This one-of-a-kind oceanfront estate property includes 4.3 acres of upland plus another 2.65 acres of baybottom and approximately 400 feet along the water! There is also a deep water dock (going into permitting for repair) and a unique collection of rare mature palms. The Native Residential (NR) Zoning allows for many different options for future development and also allows for weekly rentals. This is one of the rare, truly private large parcels on Plantation Key in Islamorada. Dont miss the opportunity to make this unspoiled piece of the past part of your future in the Keys! Call today for more details and to request a private showing.

$20,995,000
Plantation Key
Pearl City   - MM: 88.00
6 Bed, 6 Baths, 7,738 SqFt Days Listed: 138
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 230ft.

Tranquility Haven features the newest construction in Islamorada... completed January 2025! As you enter the gated and fenced sanctuary a long winding driveway leads up to an elevated entrance and convenient 1st floor living access. The 6 bedrooms and 9 bathrooms provide the epitome of coastal living with uninterrupted views of the turquoise waters on the Atlantic Ocean, with serene sunrises, and the gentle symphony of waves as your daily backdrop. Nestled on 210 of private sandy beach, this 2.04ac +/- serene oasis invites you to indulge in 7,738 sf of air-conditioned elegance and 1,800 sf of covered outdoor living designed for relaxation and entertaining. At its heart, a stunning 65 blue lagoon pool with swim-up bar stools, propane fire pit and spacious lounging patio promises unforgettable moments with family and friends.Inside, every detail reflects the designers mastery, from the chefs kitchen with SubZero, Thermador, and Wolf appliances to the grand living spaces that blend sophistication with comfort. The residence boasts 2 master suites that include double bathrooms and closets! A luxurious feature of the 1st floor master suite is a unique orchid garden and immediate access to the spa and pool patio. The 2nd floor master suite ensures more privacy and the ultimate sunrise horizon view! Much more is revealed as you walk from room to room - a flex room provides for possibilities of fitness, office or guests. A family room designed with home theater technology, a 2 car garage together with a beach-access garage and professionally landscaped grounds is complete with a tropical fruit orchard! Begin each day with golden sunrises and end with starlit skies, all within the embrace of an ocean breeze. Encounter warm Winter days and cool, tranquil Summer nights.

$42,000,000
Plantation Key
Plantation Beach   - MM: 87.50
6 Bed, 6 Baths, 9,843 SqFt Days Listed: 124
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Other Dock

An exquisite masterpiece of coastal luxury crafted by visionaries to create the ultimate secluded paradise. This architectural gem, designed by the renowned Siskind architects Bruce Carlson and Steve Siskind, offers an extraordinary lifestyle in an over five-acre waterfront oasis. Raymond Jungles landscape mastery frames the canvas, while Sam Robins interior magic awaits within. Experience approximately 11,000 sq ft of air-conditioned, carefully curated living space that is meticulously crafted with attention to detail. The gross square footage exceeds 17,895 sq ft, including covered outdoor verandas that seamlessly blend indoor and outdoor living. A four-bay air-conditioned collectors car garage awaits your prized vehicles. Additional covered parking porticos and a crushed shell driveway bordered by cut coral provide ample space for guests. Step into a world of tranquility with a private saltwater pond teeming with native sea life. Wander along the stone-through path for an intimate encounter with nature and carefully curated specimens. Situated on a peninsula, this estate offers complete privacy and security. A secluded beach area invites you to dip your toes into the ocean without prying eyes. Hosting soirees on the peninsula grassy area could serve as a helipad with a tiki lounge. Resort-style amenities include a gas-heated oasis pool, hot tub, and waterfall grotto to create a tropical paradise. Built-in swim-jet therapy and a beach entrance enhance your relaxation. Gas-powered tiki torches illuminate the evenings. Thoughtful details throughout, with an air-conditioned equipment room and cabana bathroom, add convenience. The elevated, fully equipped summer kitchen features a push-button elevated TV and a pizza oven, all with unobstructed views. A 450-foot dock with two boat lifts and a private protected boat basin awaits your vessels. This is more than a home; its an unparalleled legacy of luxury and privacy waiting to be claimed.

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 06-14-2025.
Back To TopMore Info
Terms / Privacy / Accessibility ADA