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Plantation Key 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 Plantation Key homes for sale below are on the gulf side / bay side.

Total Listings 43
Order By:

$595,000
Plantation Key
Plantation Key Colony   - MM: 90.00
2 Bed, 2 Baths, 1,338 SqFt Days Listed: 53
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Charming Ground-Level Home in Plantation Key - Prime Corner Lot!Discover the potential in this 2-bedroom, 2-bath ground-level gem nestled on a spacious corner lot in highly desirable Plantation Key. This home features a large kitchen and a bright, open floor plan thats just waiting for someone to make it their own. With a little TLC, you can transform this property into the perfect Keys retreat or full-time residence. Located within walking distance to both the elementary and high school, its ideal for families or anyone seeking convenience and community in the Upper Keys. Dont miss your chance to own in one of the most sought-after neighborhoods--bring your vision and make it yours!

$780,000
Plantation Key
Lake Harbor   - MM: 89.50
4 Bed, 4 Baths, 1,540 SqFt Days Listed: 108
-9.30% ($80,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Boat Ramp

Discover your slice of paradise in Tavernier! This delightful 3-bedroom, 2-bathroom home features a bonus room and a fenced-in outdoor space shaded by beautiful, mature trees. Enjoy brand-new flooring and impact-resistant windows throughout. The open and spacious kitchen creates an ideal setting for entertaining. Youll also benefit from year-round shade provided by the large trees surrounding the property. Plus, youll have access to the Plantation Key Colony Boat Ramp, making it easy to launch your boat. Whether youre looking for a full-time home or a vacation retreat, this property offers the ultimate Florida living experience. Dont miss out on the opportunity to own a piece of paradise--call today!This single-family home was originally in the process of being converted into a commercial property within the Village of Islamorada. Due to the extended timeline for completion and the anticipated duration, the seller has decided to list the property. With the proper guidance and approval from the Village of Islamorada, this property can easily be transformed into a commercial space. It is located in the Highway Commercial (HC) zoning district.seller is a licensed real estate agent

$795,000
Plantation Key
High Point   - MM: 89.00
2 Bed, 2 Baths, 1,120 SqFt Days Listed: 58
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Basin

Islamorada Home - Move-In Ready!2 bed, 2 bath home on a spacious corner lot, fully fenced with an electric gate. Enjoy an amazing homeowners park featuring sunset views, a private beach area, and a boat ramp. Additional storage space downstairs, with washer and dryer conveniently located upstairs. Relax in your own sauna or on the beautiful porch overlooking the trees. Swinging gates allow easy access for a large boat or RV. Great location on Plantation Key near Founders Park. Call today!

$825,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,410 SqFt Days Listed: 44
-2.37% ($20,000) 1 Price Change : Last Change 1 Day Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

This stunning CBS, ground level home in an X Zone has been beautifully updated! With 1,410 sq. ft. under air, this 3-bedroom, 2-bath home is a gem located in one of Islamoradas most desirable and convenient neighborhoods--Plantation Key Colony. Situated on a fully fenced and gated lot youll be welcomed by an abundance of sunlight and lush greenery.The main living area boasts vaulted, insulated ceilings. The chefs kitchen is equipped with stainless steel appliances, an abundance of wood cabinetry, gorgeous granite countertops, and an oversized island perfect for entertaining. For just $250 annually, join Plantation Key Colonys voluntary HOA to access the private bay front homeowners park, beach, truck/trailer parking, and boat ramp located just down the street. Enjoy the best of Florida Keys living in one of Islamoradas most beloved neighborhoods! All information provided is deemed reliable but not guaranteed. Buyers are advised to conduct their own independent investigations and due diligence regarding the

$850,000
Plantation Key
Edenaire   - MM: 90.50
3 Bed, 3 Baths, 1,344 SqFt Days Listed: 103
-10.04% ($94,900) 3 Price Changes : Last Change 24 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Relax and Revitalize in this Stylish Island Home! Move-In Ready! Much larger inside than it appears from the outside. Live the Florida Keys lifestyle in this 3-bedroom 2-bath home in desirable Edenaire Subdivision. Nestled in a prime location on 1-1/2 lots located in the X-Zone (highest elevation in the Florida Keys), this home offers modern upgrades, a new roof 2022, open floor plan, and coastal charm. Includes a variety of fruit and tropical trees such as Starfruit, Bahamian Cherry, Keit Mango, Jamaican Dogwood, Bismark Palm and more. Durable concrete construction for peace of mind. Excellent location with private neighborhood park with boat ramp and 72-hour dockage, trailer parking and picnic tables. Easy access to Bay or Ocean through Tavernier Creek. Close to shopping, schools, restaurants, and hospital. Delight in all the Florida Keys has to offer. This is an excellent home for living and working in the Keys or as investment property. Not a Drive by!!!

$995,000
Plantation Key
Key Heights   - MM: 88.50
3 Bed, 3 Baths, 1,358 SqFt Days Listed: 38
-7.93% ($85,750) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Discover old Florida charm with this enchanting 1960s Florida Keys bungalow, featuring on a rare double with easy access to neighborhood boat ramp to the Florida Bay.This single level home is conveniently located on Plantation Key in Islamorada. Features included stunning Dade County Pine ceilings and classic Saltillo tile floors. The kitchen and bathrooms have been remodeled and updated with new appliances including an induction range and oven, quartz counter tops and tile backsplash, pairing classic architecture with modern style and convenience. The primary bedroom includes an en suite bathroom and walk in closet. Off the kitchen you will find an entertaining space with bar area which leads to your backyard paradise, complete with a lush turf lawn and 100 sqf Tiki hut perfect for entertaining, complete with ambient lighting and fans. The entire property is surrounded by professional, mature landscaping, which offers both privacy and a tropical oasis.Additional features include a versatile storage outbuilding for extra flex space. The double lot has plenty of room for parking your boat, vehicle, toys or transforming into your own personal retreat .The neighborhood incudes an optional owners park ($100/yr for vehicle gate access) just a block away with a boat ramp, kayak,, dock, fish cleaning station or enjoy the breathtaking sunsets over the bay. This home is in a quiet residential neighborhood on Plantation Key and only a mile and half from Founders Park where you can enjoy pickleball, tennis, swimming, dog park and marina or many of Islamoradas local events. Dont miss this unique opportunity to own a slice of paradise.Agent is property owner.

$1,100,000
Plantation Key
Bay Ridge   - MM: 87.50
3 Bed, 3 Baths, 1,682 SqFt Days Listed: 279
-4.26% ($49,000) 1 Price Change : Last Change 112 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Othe

Welcome to your charming ground-level concrete home nestled in the highly sought-after Bay Ridge subdivision in Islamorada! This property, situated on a corner lot, boasts a prime location within the coveted X flood zone. Step into this spacious abode offering 3 bedrooms, 2 bathrooms, and bonus room with a built-in bar, ideal for accommodating family gatherings and entertaining guests. The layout provides ample flexibility to tailor the space to your unique lifestyle preferences. Outside, you will enjoy the spacious corner lot offering mature landscaping and lush green lawn along with a brick-paved circular driveway. Immerse yourself in the incredible community amenities, including a beautiful marina, inviting pool, and convenient boat ramp, perfect for enjoying the lifestyle at your leisure. For outdoor enthusiasts, nearby Founders Park offers a sandy beach, olympic-size pool, boat ramp, ball fields, tennis/pickleball courts, and a dedicated dog park. Whether you choose to enjoy the property in its current state or embark on a journey of customization to fulfill your vision, the options are boundless.

$1,145,000
Plantation Key
Key Heights   - MM: 88.50
3 Bed, 3 Baths, 1,288 SqFt Days Listed: 129
-3.78% ($45,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Tropical Paradise in Islamorada - 4BR/3BA Home Just 100 Yards from the Water!Welcome to your dream home in the heart of the Florida Keys! This charming single-family residence offers 1,767 sq ft of coastal comfort, perfectly situated just 100 yards from the crystal-clear waters of Islamorada.4 spacious bedrooms & 3 full bathroomsBright, open-concept living area with tropical vibesGenerous storage throughout - perfect for all your Keys gearPrivate park access with exclusive boat rampIdeal location for boating, fishing, kayaking & paddleboardingWhether youre looking for a full-time oasis or a weekend getaway, this home has it all -- space, convenience, and a touch of paradise.Dont miss out on this slice of island life!

$1,199,000
Plantation Key
Plantation Tropical Park   - MM: 91.00
5 Bed, 5 Baths, 2,754 SqFt Days Listed: 37
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Live the Keys Lifestyle in Your Dream Home! This Florida Keys-style home blends elegance, functionality, and the relaxed tropical vibe of your dreams. Open floor plan offers a seamless transition between the spacious living, dining, kitchen, and versatile loft areas. Spacious primary bedroom features a custom ensuite bath. Have your own private spa day or refresh under the ample rain shower. Thoughtfully designed layout with generously sized bedrooms provides ample space for family or visiting guests. Three full bathrooms provides for no waiting in line during busy mornings or vacation stays. An open concept design delivers the heart of the home an abundance of workspace to prepare anything from large meals to quick snacks, perfect for any culinary creation all while continuing to socialize with family or guests. Multipurpose loft area adds design flair and openness to the living areas below, use as an office, music room ... the possibilities are endless. Separate laundry room for added convenience and organization. Detached garage offers roomy and easy access attic space for storage. Park your prized auto or boat inside or convert it to living space for guests. Street-to-street access offers ease of parking and access. Attached storage shed to the garage provides extra space for tools to toys or convert to additional bed/bath. Room for a pool this tropical property has plenty of space to create your outdoor sanctuary. Located in an X-flood zone for lower insurance rates. Insulated glass windows and French doors bestows natural light and energy efficiency flow beautifully throughout the estate. The unique outdoor oasis and niches provide perfect spots for BBQs, sipping cocktails, or enjoying quiet conversations under the stars. Conveniently located close to shopping, schools, restaurants, hospital+. Easy access to Bay or Ocean through Tavernier Creek. Neighborhood boat ramp. Easy access to Bay or Ocean through Tavernier Creek. Welcome to your slice of paradise!

$1,250,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,376 SqFt Days Listed: 77
-3.47% ($45,000) 1 Price Change : Last Change 37 Days Ago
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
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,360 SqFt Days Listed: 86
-10.28% ($149,000) 3 Price Changes : Last Change 2 Days Ago
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. Relax under the lanai and watch the manatees play and the tarpon roll right off of your 50ft dock. Situated on a deep water canal, youll enjoy quick access to Florida Bay or the ocean via Tavernier Creek and convenient boat fuel at the end of your canal. Inside, the home features a great floorplan for entertaining, tile floors throughout, a well appointed kitchen with plenty of storage, stainless steel appliances and a separate wine fridge. The exterior 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 $250/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.

$1,369,000
Plantation Key
Indian Waterways   - MM: 89.00
2 Bed, 2 Baths, 1,148 SqFt Days Listed: 76
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

$1,574,900
Plantation Key
Indian Waterways   - MM: 89.00
3 Bed, 3 Baths, 1,769 SqFt Days Listed: 74
-3.08% ($50,100) 2 Price Changes : Last Change 2 Days Ago
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!

$1,590,000
Plantation Key
Plantation Beach   - MM: 87.50
3 Bed, 3 Baths, 2,117 SqFt Days Listed: 27
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Nestled on a generous half-acre lot in one of Plantation Keys most sought-after neighborhoods, this stunning 3-bedroom, 2.5-bath home with a dedicated office offers the perfect blend of comfort, style, and island living. Boasting 2,117 sq ft of interior space, this property also includes a small guest quarters--ideal for extended family or visiting friends.Step inside to discover a bright, open-concept layout with tasteful finishes and an easy flow from the living room to the dining area and kitchen. The dedicated office provides the flexibility to work from home in peace, while the spacious primary suite offers a private sanctuary complete with an en-suite bath. Step outside and youll find an entertainers paradise. The heated swimming pool with a waterfall is perfect for year-round enjoyment, while the covered outdoor entertainment area and cozy fire pit create the ideal setting for gatherings under the stars. The oversized two-car garage offers ample room for vehicles, tools, and toys--plus extra space for your boating or fishing gear. Lush tropical landscaping surrounds the home, offering privacy and a true sense of tranquility just minutes from schools, marinas, restaurants, and all that the Florida Keys lifestyle has to offer. The community offers one of the most premier homeowner parks in the Upper Keys with an exceptional blend of amenities and natural beauty. Enjoy a private beach, boat ramp, and temporary dockage--perfect for boating enthusiasts. Soak in breathtaking sunsets over the water and take advantage of a tranquil setting that captures the best of Florida Keys living.Whether youre looking for a full-time residence, vacation home, or investment opportunity, this rare gem on Plantation Key has it all.

$1,590,000
Plantation Key
Plantation Key Colony   - MM: 90.00
2 Bed, 2 Baths, 978 SqFt Days Listed: 23
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

FUNKY KEYS PRIVATE WATERFRONT HIDEOUT to hold or rebuild on TWO LOTS with expansive 12,500 sq ft on an impressive 100 feet of DEEP WATER canal-frontage, in peaceful and very desirable PLANTATION KEY COLONY. Enjoy the home while building your Dream Home next door! This inviting home offers a blend of character, comfort, and potential. Experience the relaxed rhythm of life in the Florida Keys. The homes solid CONCRETE STRUCTURE, with impact-resistant windows and doors throughout, allows you to enjoy both security and serenity. This two-bedroom retreat is Ideally located in the heart of Islamorada, making this property more than just a place to live--its a lifestyle. Families will love the convenience of having highly rated schools like Plantation Key School (K-8) and Coral Shores High School (9-12) nearby. Dont miss your chance to shape your dream waterfront escape in one of the Keys MOST DESIRABLE communities. Voluntary HOA provides access to the private bayfront homeowners park, beach, truck/trailer parking, and boat ramp! Close and EASY ACCESS TO BAYSIDE AND OCEAN. Enjoy the getaway as is, remodel, or BONUS you can build your dream home on the vacant lot next door that is included...! Inquire about house on lot and vacant lot for sale separately!

$1,700,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,464 SqFt Days Listed: 85
Single Family - Contingent - 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 primary 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 carport for your car or boat protection.And outside, youll meet a paved permeable driveway, a fenced in yard, attractive landscape and an impressive sprinkler system.Call now for an appointment. See you there!

$1,750,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,740 SqFt Days Listed: 85
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift875ft.

OWNER FINANCING-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.

$1,750,000
Plantation Key
Lake Harbor   - MM: 89.50
5 Bed, 5 Baths, 2,779 SqFt Days Listed: 190
-20.45% ($450,000) 3 Price Changes : Last Change 35 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!

$1,850,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 2,100 SqFt Days Listed: 95
-5.08% ($99,000) 1 Price Change : Last Change 30 Days Ago
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!

$1,870,000
Plantation Key
Indian Waterways   - MM: 89.00
3 Bed, 3 Baths, 1,230 SqFt Days Listed: 122
-21.72% ($519,000) 3 Price Changes : Last Change 4 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, paddleboarding 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.

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.
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