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Plantation Key Waterfront Homes on the Bay / Gulf Side For Sale

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

Total Listings 31
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$1,295,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,376 SqFt Days Listed: 5
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Enter the Islamorada waterfront game with this fantastic ground level 3-bedroom home, perfectly situated between Tavernier & Snake Creek with direct bay access. Equipped with a brand new metal roof and built above flood to help with insurance costs. Canal side has 50 feet of frontage with a 30-foot concrete dock in good condition and a permit in place to extend the last 20 feet. Perfect Keys weekend retreat or for those looking to make the jump up to waterfront living. Room for a pool. Close to schools and the neighborhood boat ramp. Lock it up just in time for summer!

$1,300,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 2,240 SqFt Days Listed: 36
-7.14% ($100,000) 1 Price Change : Last Change 8 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

Looking for a home to accommodate you and your guests? This concrete construction property features three bedrooms and two baths on the upper level. Lower level offers two bedrooms and one bath, plus a waterfront screen porch, open floor plan, legally permitted enclosure with a living area that includes a kitchenette, plus living room. Plenty of storage with attached workshop/garage. Located on a plugged canal in Venetian Shores, there is a marina available for lease dockage monthly depending on availability.

$1,369,000
Plantation Key
Indian Waterways   - MM: 89.00
2 Bed, 2 Baths, 1,148 SqFt Days Listed: 4
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Boat

Waterfront Canal Home located in the Best Islamorada Plantation key Location. Great Vacation Rental is being sold furnished . Turnkey with 5 star reviews ! Large bedrooms with King Beds. Metal Roof , Smart TVs, Quartz countertops , open kitchen , Modern bathrooms, Great living room with open kitchen, Washer & Dryer, Screened in wrap around porch overlooking the water. 60 of Canal Frontage. HUGE enclosed Garage area underneath that can be extra living space New AC, New appliances, large yard area plenty of parking , 60 Private Dock , Beautifully remodeled. Large enclosed garage under home , Close to Founders Park with access to pickleball. swimming Pool , Beach, tennis and more. Own your own slice of paradise

$1,449,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,360 SqFt Days Listed: 14
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Lift50ft

Welcome to the Keys Life Getaway! Located in the desirable Tavernier neighborhood of Plantation Key Colony, this fully furnished 3 bedroom, 3 bathroom concrete canal home is awaiting your arrival. Situated on a deepwater canal, youll enjoy quick access to Florida Bay or the ocean via Tavernier Creek. The property features low maintenance landscaping, a 15,000lb boat lift, jet ski davit and a storage shed. The neighborhood features a wonderful bayfront homeowners park where you can launch your boat or relax and watch the sunset! The boat ramp was recently renovated and features a new concrete ramp and dock. Optional membership to the homeowners park is $200/year. The home is conveniently located near Coral Shores High School, Plantation Key Elementary School, shopping, grocery, bars & restaurants. This home will make a great full-time residence, or 2nd home with the ability to generate vacation rental income.

$1,625,000
Plantation Key
Indian Waterways   - MM: 89.00
3 Bed, 3 Baths, 1,769 SqFt Days Listed: 2
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp

This is it!! Your Florida Key Oasis! Quintessentially Key-z, this home has it all ... and then some. Located in the very desirable Indian Waterways Community of Tavernier on Plantation Key. Stylish Two Bedroom / Two Bath Main house plus a super inviting 1/1 guest house that your guests will never want to leave! Relax and entertain in the canal front Tiki hut as you enjoy tropical breezes. Cool off on the Custom Outdoor Shower after you dock your boat. Composite Dock ensures longtime enjoyment. And an Outstanding Double-sided Garage + storage room is a major Bonus!!! As Well as the personal boat ramp, that is perfect for launching/storing a flats boat, skiff, Jet Ski, or Kayak. Both the Main House and Guest House boast gorgeous, exposed wood-beamed ceilings that are gleaming works of Art. Large Bedrooms and stylishly updated Bathrooms. Great privacy with a nature preserve across the Street CBS Construction and a White Picket Fence add to the irresistible charm of this property that personifies Tropical Chic. Super Close proximity to Tavernier Creek via the famous Toilet Set Cut. World Class deep water, reef, and backcountry fishing are mere minutes away as are incredible diving, snorkeling, Lobstering, and sandbar-ing! Come Grab a slice of Florida Keys Living!

$1,650,000
Plantation Key
Plantation Key Colony   - MM: 90.00
2 Bed, 2 Baths, 1,205 SqFt Days Listed: 29
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Ramp

Nestled on a quiet street in the heart of Plantation Key, this one-of-a-kind canal-front home offers a picturesque retreat. As you pass through the electric gate, youll be greeted by lush foliage, vibrant blue skies, and breathtaking sunsets.This turn-key property has been thoughtfully renovated, allowing you to start enjoying your Keys lifestyle immediately. The upstairs features an inviting open-concept living area with a modern kitchen, highlighted by tongue-and-groove wood ceilings, a gas range, and a fresh renovation complete with new backsplash, cabinets, and appliances. Youll also find two bedrooms, one bathroom, and an oversized porch that provides stunning canal views.The downstairs area boasts a fully equipped 1-bedroom, 1-bathroom apartment, ideal for guests or rental income, along with a convenient garage. Enjoy outdoor meals on the covered porch or relax by the pool in the shade. For sun-seekers, the pool deck offers ample space for lounging.The private pool area is a true retreat, featuring a hammock and hot tub nestled among lush landscaping--perfect for afternoon naps or stargazing. Additional updates include a new roof, interior remodel, and AC in 2019, a new gas tank and line for the kitchen range in 2022, and a new 12 x 24 pool in 2022. The property also includes a 10,000 lb boat lift and a boat ramp that can double as storage for your flats boat.Quick trip to the Atlantic Ocean through nearby Tavernier Creek where you can enjoy world class fishing and diving, as well as the Gulf of Mexico out your back door to enjoy backcountry fishing, kayaking and paddle boarding. Enjoy cruising to several local restaurants by boat. Conveniently located to restaurants, groceries stories, fantastic schools, and hospital. Your tropical paradise awaits--come experience it today! ***BUYER TO VERIFY ALL INFORMATION.***

$1,750,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,740 SqFt Days Listed: 13
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift875ft.

Plantation Key Colony - Completely UPDATED-Like New - 2/1 up and 1/1 down, Plus -2- more Bonus Room- Great to Live in or Great for Renting out Half and using the other half or making it a Double rental income. Large Concrete Dock 75 Ft. w/ 20,000lb Boat Lift. This Big Lot is 125x75 with a Tiki Hut & Hot Tub. Quick Direct access to Bay & Ocean. Beautiful Homeowners Park on the Bay with a Beach & Boat Ramp. Plenty of room for a new pool. Centrally located near Shopping, Schools, Restaurants and more.

$1,800,000
Plantation Key
Lake Harbor   - MM: 89.50
5 Bed, 5 Baths, 2,779 SqFt Days Listed: 118
-18.18% ($400,000) 2 Price Changes : Last Change 9 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits50ft.

Welcome to your slice of paradise in Islamorada! This stunning canal-front property offers direct bay access and quick, convenient ocean access, making it a boaters dream. Concrete home boasts 5 bedrooms, 3.5 baths - 2,779 sq of elegant living. Upstairs features 3 spacious bedrooms, 2baths plus powder room,. Two separate living areas upstairs provide ample space for relaxation and entertaining. The designer kitchen with generous chefs pantry is perfect for culinary enthusiasts, while the Chicago brick pavers add timeless charm.The ground level features a permitted, private 2-bedroom, 1-bath mother-in-law suite, ideal for guests or extended family. Outside, the private, lushly landscaped yard is adorned with fruit trees, creating a serene oasis. With its unbeatable location, abundant storage, and exceptional features, this home is a rare gem in the heart of the Florida Keys.Dont miss this opportunity to enjoy the best of waterfront living in Islamorada!

$1,885,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,464 SqFt Days Listed: 13
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift70ft.

Fishermans Paradise Found just minutes to Tavernier Creek. This tastefully updated 3/2 comes complete with an expansive 70ft Dock, a newer 27 K boat lift,a sweet in ground pool complimented by a large Tiki Hut for pool side entertainment and accented with an attractive outside lighting system. Inside you will find a lovely updated kitchen with Quartz Countertops, newer cabinets, stainless steel appliances, as well as vinyl plank flooring throughout, impact windows and doors, and a large third floor master bedroom with a balcony looking east over water.Outside the living and dining area you have a large covered, waterfront patio, perfect for dining or morning coffee, or entertaining.Downstairs,a high ceiling, climate controlled garage is paired beside a covered slot for your car or boat.And outside, youll meet a paved permeable driveway, a fenced in yard, attractive landscape and and impressive sprinkler system.This wont last.Call for appointments. Showings can be scheduled for either Wednesdays or Saturdays.See you there!Interior photos soon.

$1,940,000
Plantation Key
Venetian Shores   - MM: 86.00
3 Bed, 3 Baths, 2,055 SqFt Days Listed: 151
-7.62% ($160,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Slip4

Welcome to your dream home in the heart of the Florida Keys! This exquisite two-story waterfront residence in prestigious Venetian Shores offers the perfect blend of luxury, coastal charm, and unparalleled boating access to the Atlantic Ocean and Florida Bay with a 40 ft. boat slip steps away. Offered furnished so just bring your toothbrush, or your renters! Brilliant investment in the Florida Keys.With 3 bedrooms and 3 full baths, this home is move-in ready to start living the Keys lifestyle. As you step inside, youll be captivated by the bright, airy spaces adorned with designer furnishings that exude elegance. The open-concept living area seamlessly flows into a gourmet kitchen with all KitchenAid(r) stainless appliances, perfect for entertaining. Porcelain tiles add modern warm appeal. Expansive windows provide stunning canal, peekaboo bay, and marina views. Plus, open water vistas of Snake Creek invite natural light, the beauty of the outdoors and magnificent sunsets in. Downstairs, enjoy a separate apartment for guests, a private office, inlaw suite or teen sanctuary. This home is also equipped with eco-friendly features such as a tankless water heater, solar landscape lighting, whole home Sonos system, security, and whole home water purification system.Step outside to your private paradise! With near instant ocean and bay access, your 39 ft. boat slip can accommodate the perfect boat for exploring the nearby reefs, fishing, or cruising the gorgeous waters of Islamorada, the Sport Fishing Capital of the World.Located in one of the Keys most sought-after Plantation Key neighborhoods, youll be just moments from world-class dining, shopping, vibrant local culture and Founders Park with beach, sports fields, amphitheater and pool complex. Whether youre seeking the serenity of a full-time residence, vacation getaway, or income generator, this home is your ticket to paradise. Call now, this gem wont last!

$1,949,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 2,100 SqFt Days Listed: 23
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits50ft.

Experience the lifestyle of waterfront living in this quintessential Islamorada home. Featuring 3 bedrooms and 2 bathrooms on the second floor, this residence includes an interior staircase leading to the legal, above-flood downstairs living space. The first floor offers a second living room--easily convertible into a fourth bedroom--along with a full bathroom, making it ideal for separate guest quarters or expanded living. The property is encompassed by a stunning front coral wall and offers 50 feet of dockage with direct bay access. Conveniently located near schools, this home sits in the last neighborhood along the four-lane highway. Discover why The Colony is a beloved community among locals--schedule your visit today!

$1,950,000
Plantation Key
Indian Waterways   - MM: 89.00
2 Bed, 2 Baths, 1,858 SqFt Days Listed: 125
-6.92% ($145,000) 2 Price Changes : Last Change 33 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift60ft.Concre

This charming Keys home strikes the perfect balance - not too big, not too small, and super easy to maintain. There are plenty of outdoor living spaces that add to the comfortable and active indoor/outdoor lifestyle. Fully fenced for privacy, it boasts solid CBS construction with a pitched concrete roof, plus impact windows and doors for peace of mind. Dive into the fun with a jetted pool and a 10,000 lb. boatlift on a 60 ft. concrete dock. This home is fully fenced and a sliding gate welcomes you to a spacious pavered parking area and breezeway. Inside, the open-concept kitchen and living room flow seamlessly to the huge canalside terrace through two sets of triple-pocket sliders. Upstairs, youll find two cozy bedrooms and two bathrooms. Downstairs, theres a permitted enclosure with a permitted full bath, plus a big covered outdoor entertaining space in the breezeway - perfect for those laid-back Keys nights. The good times continue as you step out to the pool deck, where you can relax in the jetted pool, complete with seating all around. The pool also features a heater and chiller, plus a changing color underwater light - its the ultimate spot to unwind after a day on the water, and the kids will love it too! Out on the dock, youll find the 10,000 lb. boatlift, a fish cleaning table, and a dock ladder. Water and power are available, and theres plenty of extra dock space for friends who drop by. This is the perfect home to live the Keys lifestyle and create memories with loved ones!

$1,995,000
Plantation Key
Plantation Key Colony   - MM: 90.00
2 Bed, 2 Baths, 1,022 SqFt Days Listed: 30
-2.68% ($55,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift100ft.Concr

Welcome to 240 S Coconut Palm Drive, Islamorada!Get ready to fall in love with this amazing Florida Keys home. Located in the heart of Islamorada, this beautiful canal front property has everything you need for the perfect island life. The brand-new 100-foot dock is a boaters dream, with a 13,000lb boat lift, utilities for a new Fish Cleaning Station with the Atlantic and Gulf only minutes away. Take a dip in your brand new private swimming pool, or unwind in the oversized hot tub after a day of adventure. The outdoor space with the newly enlarged Tiki Hut is perfect for chilling out, hosting friends, or just enjoying some peaceful moments by yourself. The oversized, fenced in, 12,000 sq ft. lot is ready for custom landscaping or additional storage--plenty of room to bring your own vision to life!Inside, the house is spacious and stylish, with gorgeous waterfront views that make every day feel like a vacation. New metal roof in 2019 and the interior totally renovated in 2016. Located in a desirable neighborhood with access to a community homeowners park with a boat ramp. Close to Plantation Key School and Coral Shores High School as well as grocery stores, many new restaurants and shopping options. Whether youre looking for a sweet vacation spot or a permanent home, 240 S Coconut Palm Drive has it all.Dont miss out on this slice of paradise!

$2,000,000
Plantation Key
Indian Waterways   - MM: 89.00
4 Bed, 4 Baths, 1,500 SqFt Days Listed: 28
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 33ft.

Exclusive opportunity to own this canal-front duplex and the adjacent vacant lot in Indian Waterways subdivision of Islamorada, FL. Each unit features two bedrooms, one bathroom, original custom kitchen cabinetry, and terrazzo floors. A connecting interior door allows the property to function easily as one expansive home or continue to be used as two separate living spaces. Boating enthusiasts will appreciate the 33-foot dock on a wide canal with direct access to the Florida Bay. The combined lots span 0.40 acres and are adorned with mature native plants and trees including Short Leaf Fig, Pigeon Plum, Mahogany, Locust Berry, and Crabwood -- creating a haven for birds and butterflies. Conveniently located near schools, Mariners hospital, grocery stores, shopping, entertainment, and Founders Park, which offers a swimming pool, bayfront beach, playground, pickle ball, tennis, and dog park. Whether youre seeking a primary residence, vacation home, investment, or redevelopment opportunity, this property invites you to live, work, and enjoy the tropical Florida Keys lifestyle.

$2,049,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,295 SqFt Days Listed: 257
-1.91% ($40,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Lift,Dav

**Waterfront Paradise: Solid Concrete Home on Deep Water Canal**Nestled along a serene deep water canal, this exquisite solid concrete home awaits its new owner. Embark on a brick paver driveway that leads to a turn-key residence designed to impress.As a boaters paradise, this property boasts a private boat lift, davit, clean out station, and outdoor shower. Access to the communitys boat ramp allows for effortless excursions.Step inside and be captivated by the beautifully furnished interior with breathtaking canal views. The open floor plan seamlessly blends the gourmet kitchen, dining area, and living room, offering an inviting space for entertaining and relaxation. Top-of-the-line appliances and entertainment areas elevate the living experience.The spacious master bedroom and bathroom provide a luxurious oasis with access to a large screened balcony. The master bathroom features a soaking tub, separate shower, and double vanity.The downstairs level offers an enclosed garage with two bay doors and ample storage. A custom-made bar, full bathroom, and additional storage space create a versatile flex room perfect for various uses.The propertys tranquil exterior features lush landscaping, gardens, and a charming front porch. The rear stairs provide convenient access to the waterfront.With a straight shot to the bay and just around the corner from the ocean via Tavernier Creek, this home offers unparalleled access to the water. The neighborhood community offers a boat ramp for members.This dream home is a rare find. Dont miss this opportunity to own a piece of paradise. Call today to schedule a private showing and experience the beauty of this solid concrete waterfront residence. Call Today!

$2,099,000
Plantation Key
Sunshine Estates   - MM: 90.50
3 Bed, 3 Baths, 2,154 SqFt Days Listed: 21
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits70ft.

What a great location! Discover Serenity at Manatee Crossing, nestled along the picturesque waterways of Islamorada, where over 200 feet of waterfront embrace you from two sides. Immerse yourself in an outdoor haven, boasting a captivating pool, charming Chickee-hut, and indulgent hot tub area - each offering front-row seats to the wonders of nature. From manatees to graceful migratory birds, the surrounding mangroves create a natural sanctuary for this remarkable property. Step inside this timeless CBS home, where modern comfort harmonizes with island charm. The lower level welcomes you with a living area and full bath, while three bedrooms and three baths await on the upper level. As the sun sets, ascend to the expansive concrete roof and toast to another day in paradise, with panoramic views painting the sky in hues of orange and pink. For boating enthusiasts, get ready to launch into your aquatic adventures, while nature lovers can explore the bay at their own pace, taking in the unique beauty of Tavernier Creek and beyond. Whether you seek thrilling ocean escapades or peaceful backcountry journeys, this property offers the perfect launchpad for all your Florida Keys dreams. Dont miss the chance to experience the magic of Manatee Crossing - schedule your private tour today and discover why this property is truly special.

$2,200,000
Plantation Key
Kahiki Harbor   - MM: 91.00
4 Bed, 4 Baths, 1,708 SqFt Days Listed: 35
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Other Dockage

Now Available! One-of-a-kind Opportunity in the desirable Kahiki Harbor neighborhood. 165 waterfront Corner Lot. Vintage 4 bedroom / 3 bath Custom built Keys home. 2/2 upstairs and a Great Room with all doors opening to the walk-around porch. Downstairs has 700 of additional enclosed storage, laundry, bathroom and two bedrooms. The home sits in the peaceful Kahiki Harbor neighborhood with deep water dockage all the way around the property. Davits and a concrete dock at one end, with additional dockage areas, a Gazebo and a Sailboat Launch Ramp following the corner of the 8,760 oversized lot. The large yard offers potential for a pool and outside entertaining areas. Endless possibilities await!- Build your Dream Home on this Unique and One-of-a-Kind Property, just off Tavernier Creek and minutes from the Ocean or Bay.

$2,200,000
Plantation Key
Indian Waterways   - MM: 89.00
3 Bed, 3 Baths, 2,241 SqFt Days Listed: 182
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp

Are you looking for that PERFECT FIXER UPPER? Well look no further. Welcome to 200 Pueblo St. This house has great bones! One Story home ABOVE FLOOD, Concrete Roof, AND is situated on 2 WATER FRONT LOTS that total 13,200 +/- SqFt. 120 ft of canal frontage! Short idle down the canal to the Bay and quick Ocean access via Tavernier Creek. Two car garage with a workshop and extra storage area. Mother in Law Suite. Nice oversized screened porch overlooking canal. Plenty of room for RVs , boat trailers, water toys. Working boat ramp and multiple sheds. Lots of room to expand or redevelop. Get the Afternoon Shade and eastern exposure on this side of the canal. Concrete dock. Very private & quiet street. This property is conveniently located close to great schools, grocery stores, restaurants, churches and a hospital. OWNER FINANCING. ***BUYER TO VERIFY ALL INFORMATION***

$2,200,000
Plantation Key
Indian Waterways   - MM: 89.00
3 Bed, 3 Baths, 1,230 SqFt Days Listed: 50
-7.91% ($189,000) 1 Price Change : Last Change 10 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift78ft.Concre

Located on the main free flowing canal just off the Bay of America and a short ride to the Ocean thru Tavernier Creek or Snake Creek. Fishing diving, paddleboading is right here!! 254 Navajo Street offers two bedrooms two bathrooms upstairs and one bedroom and one bathroom downstairs and an open concept living area upstairs. With a stainless-steel kitchen, granite countertops, and a private backyard oasis featuring a sparkling pool with water and fire features, this property is perfect for entertaining. Its close proximity to the ocean and local amenities makes it a slice of paradise waiting for you to call home. This canal front home has 78 of dockage with a boat lift. There is a shaft ready for elevator installation. Owner is a licensed Real Estate Agent.Come see this little gem...great for your pets as well.

$2,295,000
Plantation Key
Misc Plantation Key   - MM: 85.00
5 Bed, 5 Baths, 2,450 SqFt Days Listed: 77
-8.20% ($204,999) 1 Price Change : Last Change 3 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 40ft.

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 04-03-2025.
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