Divider
Content Divider

Florida Keys Waterfront Homes on the Bay / Gulf Side of the Island For Sale

Total Listings 265
Order By:

$1,200,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,152 SqFt Days Listed: 118
-4.00% ($50,000) 1 Price Change : Last Change 5 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Lift204f

This home has a lot to offer! Great home, great neighborhood, great lot! This home is situated on a 8,400 SF corner lot, with canal on two sides. Plenty of concrete seawall equipped with both a boat lift, and davits. There are no bridges to worry about getting under, and a short ride to the open water. The home has been recently updated, and there is plenty of room for people and fishing gear/water toys. Renters in the home until March 1, not available to show until then.

$1,225,000
Big Pine Key
Misc Big Pine Key   - MM: 33.00
3 Bed, 3 Baths, 1,654 SqFt Days Listed: 15
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift25ft.

Escape to quintessential No Name Key to find this waterfront sanctuary. No Name Key is a secluded paradise; free of commercial development with fewer than 50 homes nestled in a one-of-a-kind conservation setting. This location offers unmatched stargazing and serene surroundings--yet its just over 10 minutes from the amenities of Big Pine Key, 45 minutes from Marathon and 1 hour from Key West. Reminisce on the Old Florida Keys while driving down the private road to Bimini Lane--a tranquil street with just 6 homes, surrounded by County-owned land. This hidden gem offers privacy, peace, and a true sense of community. Situated on a 13,980 square foot double lot with 120 feet of waterfront, this property boasts deep water, immediate Gulf access, recently upgraded 25-foot dock with low-maintenance decking, 15,000 lb boat lift, and 8 x 10 foot floating dock--perfect for boating enthusiasts and nature lovers alike. Originally built in 1995 by a concrete contractor as his personal Keys escape, this three bedroom, two bathroom wood frame home features poured concrete columns and balcony, metal roof, and storm-conscious design. Inside, youll find nearly 1,700 square feet of living space plus generous screened and open-air porches ideal for catching island breezes. Recent upgrades include updated AC, and connection to the Countys electric, water and sewer systems, complementing the nearly 15,000-gallon cistern, solar panels, and propane for off-grid resilience. The main level welcomes you with an open-concept living, dining, and kitchen area, along with two bedrooms and a full bath. Upstairs, the primary suite offers a renovated bathroom, updated flooring, and a private balcony with picturesque views of the Gulf. Ample carport parking for 4 vehicles with expansive room to add a pool and tiki hut to complete your tropical oasis. Whether youre seeking a peaceful full-time residence or a secluded second home, this No Name Key retreat is your gateway to authentic Keys living.

$1,245,000
Big Pine Key
Whispering Pines   - MM: 30.50
4 Bed, 4 Baths, 2,176 SqFt Days Listed: 257
-10.75% ($150,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davit Pads,Boat Lift

Nestled in the heart of Big Pine Key, this fantastic property offers 4 bedrooms, 2 baths, and 2,176 sq ft of living space. The living room boasts a charming open beam ceiling and a split floor plan. The fourth bedroom is a delightful bunk room. The kitchen, updated in 2017, features white cabinets, granite countertops, and stainless-steel appliances. The home is adorned with tile floors, impact windows, and a new metal roof installed in 2018.Situated on a half-acre, fenced yard with lush grass, this property includes a large saline chlorinated pool, two tikis, and a 75-foot seawall dockage and boat lift perfect for multiple boats. Easy access to the ocean or the gulf is available via Bogie Channel. Additional amenities include a dockside fish cleaning station, an outdoor shower with hot and cold water, and wiring for a portable generator. A 10x20 detached workshop/shed with power provides extra storage or workspace. This property also could be used as a monthly vacation rental.

$1,249,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,056 SqFt Days Listed: 14
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Other Dock

Welcome to your private tropical paradise in Big Pine Key! This fully remodeled corner canal home offers 180 ft. of waterfront with ocean access, only one neighbor, and no HOA! Plenty of room to park your RV & all your toys. Inside, enjoy new tile flooring, zebra blinds, updated bathrooms, and a brand-new kitchen with quartz counters, new cabinets, and appliances. The oversized fenced yard features a patio & new outdoor kitchen with a BBQ, hibachi, gas range, & sink. Boaters will love the 15,000 lb boat lift & 10,000 lb triple jet ski lift. With impact windows & doors, a metal roof, fresh paint, irrigation system, & mosquito misting system, this home is built for comfort and style. Dont miss this rare waterfront gem!

$1,250,000
Marathon
Venice   - MM: 52.00
2 Bed, 2 Baths, 1,200 SqFt Days Listed: 41
-3.77% ($49,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Welcome to your dream waterfront retreat! This newly renovated 2 bedroom, 2 bathroom CBS home is perfectly positioned in the heart of Marathon, offering a seamless blend of coastal modern design and island charm. Nestled in a peaceful neighborhood across from a tranquil nature preserve, this home is the perfect escape for those seeking serenity with easy access to all the Florida Keys have to offer. Step inside and be captivated by the open-concept great room, where a wall of impact glass floods the space with natural light while framing stunning canal views. The beautifully designed kitchen is a chefs delight, featuring sleek stainless steel appliances, quartz countertops, and ample prep space, perfect for preparing your fresh catch of the day. The spacious guest bedroom ensures comfort for visitors, while the primary suite offers a private oasis, complete with a luxurious ensuite bath featuring a dual vanity and custom tile shower.Outside, the possibilities are endless! The expansive yard has ample space for a pool or tiki hut, while 900 sq ft permitted lower enclosure provides endless opportunity and plenty of additional space and storage. Boaters will love the full-length concrete dock with deep-draft access, offering quick navigation to both the Atlantic and the Gulf. Conveniently located just minutes from Marathons best beaches, state parks, waterfront restaurants, and bars, as well as The Marathon Airport and the Millionaire FBO.

$1,250,000
Key Largo
Pirates Cove   - MM: 98.50
2 Bed, 2 Baths, 1,040 SqFt Days Listed: 174
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 40ft.

Dont miss this CHARMING ground level CBS Home that sits on a large corner lot with 40 of concrete dockage and a very wide canal basin. Featuring 2 bedrooms, 2 bathrooms, tongue and groove ceilings, Luxury vinyl flooring, impact windows, metal roof , and modern fencing surrounding the property. This home is offered Turn-Key, furniture and furnishings included. Come sit and relax on the back patio while watching the Manatees play in the basin. Desirable neighborhood with private boat ramp, clubhouse, and beach area only 30 minutes from the mainland. Easy to show!

$1,250,000
Key Largo
Pirates Cove   - MM: 98.50
2 Bed, 2 Baths, 1,120 SqFt Days Listed: 115
-2.72% ($35,000) 1 Price Change : Last Change 37 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift50ft.Concre

Charming Key Largo Bungalow with Bay Views and Boating Access! Discover the essence of Florida Keys living in this meticulously maintained 2-bedroom, 2-bathroom bungalow. Situated on a wide canal with immediate bay access, this home is a boaters dream come true. Spacious open-concept living area with vaulted wood beam ceiling is perfect for entertainment and relaxation. The primary bedroom features an en suite bathroom for added privacy and convenience. Step outside to enjoy a 50-foot concrete dock with a 14,000-pound boat lift, perfectly equipped for all your water adventures. Relax in the screened lanai, offering serene canal views, or entertain with ease in the built-in outdoor kitchen, ideal for grilling and cocktails under the Florida sun. After a long day of fishing, unwind in the hot tub or refresh yourself in the convenient outdoor shower. Tasteful details throughout make this home truly a tranquil Florida Keys paradise. Located in a vibrant community with a clubhouse and boat ramp nearby, this property blends charm and convenience. Just over an hour from Miami International Airport, its your gateway to the ultimate Keys lifestyle!

$1,275,000
Key Largo
Cross Key Waterways   - MM: 103.00
3 Bed, 3 Baths, 1,296 SqFt Days Listed: 81
-1.92% ($25,000) 1 Price Change : Last Change 18 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift40ft.Concre

Stunning Stilted 3-Bedroom Home with Bay Access & ElevatorDiscover this beautiful stilted 3-bedroom, 2-bathroom home, perfectly designed for comfort and convenience. Featuring spacious bedrooms with incredible closet space, this home also boasts a large storage room on the ground floor and an elevator for easy access.Located just two canals from the open bay, youll enjoy quick ocean access via Adams Cut--ideal for boating and water enthusiasts. The property offers a fantastic entertaining area, covered parking, and ample space to store your toys and trailer. 40 of seawall with a 20,000LB boat lift in the process of being installed.Dont miss this opportunity to own a waterfront gem in a prime location!

$1,275,000
Key Largo
Lake Surprise Properties   - MM: 106.00
3 Bed, 3 Baths, 1,248 SqFt Days Listed: 338
-3.77% ($50,000) 1 Price Change : Last Change 126 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Lift60ft

Location, location, location... ideally situated in North Key Largo for boating, fishing, diving, dining, shopping & more. Convenient for commuting. Whether you are seeking a primary residence, vacation getaway, or an investment property, dont miss your opportunity to own this piece of paradise. Lovely 3/2 waterfront pool home located in desirable Lake Surprise Estates. Elevated by concrete columns w/ a spacious ground floor storage room. 60 concrete dock w/ lifts & an addl concrete pad. Easy access to the bay & ocean. Spacious floorplan, vaulted ceilings & tile throughout. Kitchen w/ granite countertops, stainless appliances & an expansive island. Completely fenced, electric gate & lots of room for all your water toys. Simple to maintain salt-water pool, accordion shutters up-stairs & newer metal roof. Large, covered wrap-around patio & 2nd floor porch, perfect for gorgeous sunset views. Plenty of space to enjoy w/ your loved ones.

$1,290,000
Little Torch Key
Mates Beach   - MM: 28.50
3 Bed, 3 Baths, 1,500 SqFt Days Listed: 94
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 35ft.

Discover the perfect balance of comfort, tranquility, and outdoor living with this spacious 1,500 sqft home located on a boating canal in the Lower Florida Keys. Nestled in a quiet neighborhood, this property offers a peaceful retreat while still being just minutes away from all the natural beauty and attractions the Keys have to offer, and 30 minutes from Key West!Inside, youll find generous living space, providing plenty of room to stretch out and make this house your own. Step outside to your very own swimming pool, the perfect spot to unwind after a day on the water or to enjoy sunny Florida afternoons. The propertys canal location offers easy access for boaters, and the ability to lift your boat out of the water with a 10,000 pound boat lift. Allowing you to dock with ease after you take your boat and set out for a day of fishing, exploring, or simply enjoying the stunning waterfront views.The lower enclosure provides plenty of room to store all your tools, pool toys, and outdoor gear, keeping your living spaces organized and clutter-free.With a brand new home, you will enjoy the low insurance rates, as this home is built to the newest building code - minimizing your risk to tropical weathers!COMING SUMMER 2025 - photos of listing do not fully represent dwelling unit, subject to change. Construction process underway. Some build selections may be considered. Seller is licensed FL real estate agent.

$1,295,000
Big Pine Key
Sea View   - MM: 28.00
4 Bed, 4 Baths, 1,940 SqFt Days Listed: 84
-34.43% ($680,000) 1 Price Change : Last Change 44 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

HUGE PRICE REDUCTION- Seller is ready to move!There are only 2 houses in the over 40 acre Seaview Subdivision and both of them are for sale!Exclusive Open Water Retreat - A Secluded Slice of Paradise -Harken back to what The Florida Keys used to be like when Jimmy first discovered them. Escape to your own private sanctuary with this open-water oasis, perfect for those who cherish solitude and natural beauty. Set on over an acre of pristine land, this property boasts an open water point lot complete with a direct entrance into the ocean ideal for swimming, kayaking, and all your favorite water activities. With your very own canal and lush native vegetation, this property offers an unparalleled connection to nature.At the heart of this idyllic haven lies a 1,940 sq. ft. multi-level home thats both unique and inviting. Featuring 4 bedrooms, 2 baths, and multiple expansive decks, the home seamlessly blends modern comfort with outdoor living. Thoughtful updates include 4 ductless A/C units for tailored climate control and an on-demand water heater for convenience.Indulge in the beauty of nature from sunrise to sunset, with breathtaking sunset views from the point as your daily meditation. For boating and fishing enthusiasts, the property provides direct access to both the ocean and backcountry, making it an adventurers dream. Endless space to store your RVs, trailers and boats.This is an opportunity you wont find again. Whether youre looking for a peaceful retreat, a waterfront playground, or a private residence, this secluded property offers a rare opportunity to live the life Jimmy Buffett sings about and that youve always dreamed of.

$1,295,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,376 SqFt Days Listed: 24
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!

$1,295,000
Summerland Key
S Summerland Key Yac   - MM: 25.00
1 Bed, 1 Baths, 1,965 SqFt Days Listed: 23
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat RampOther

Seize this rare opportunity to own a prime working waterfront property with exceptional Highway visibility. This unique offering includes two waterfront buildings located at 24931 & 24933 Overseas Highway in Summerland Key, each with separate water, electric, and sewer connections for added flexibility. Situated on a 10,673 SF lot, the property features a 813 SF building, a 1,152 SF building, and a 192 SF utility/storage building for additional space. Additionally, the property includes a private boat ramp, providing convenient water access. Whether youre looking to expand or open a business or invest in a high-exposure location located on the water, this property offers incredible potential. Buyer to verify property rights.

$1,299,000
Big Pine Key
Kyle Dyre   - MM: 28.00
3 Bed, 3 Baths, 1,440 SqFt Days Listed: 40
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Concrete

Enjoy your morning coffee taking in views of the Bay, and watching the boat traffic go by on your large covered deck. In the evening, enjoy a cocktail while watching the sunset. There is approximately 210 feet of concrete seawall to park your boats and water toys. This meticulously maintained home has a metal roof, impact doors and windows, newer A/C, and many updates. Low flood insurance premium. Sellers prefer afternoon showing appointments. No pets allowed in the house on showings.

$1,300,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 2,240 SqFt Days Listed: 55
-7.14% ($100,000) 1 Price Change : Last Change 30 Days Ago
Single Family - Contingent - 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.

$1,300,000
Key Largo
Cross Key Waterways   - MM: 103.00
4 Bed, 4 Baths, 2,568 SqFt Days Listed: 49
-6.81% ($95,000) 1 Price Change : Last Change 23 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits

MULTI FAMILY OPPORTUNITY! Water view from every floor! Prime waterfront location for fishing, diving, and boating enthusiasts. Featuring a concrete block home with incredible potential, it provides immediate access to both ocean and bay-side adventures via a concrete dock. Whether youre finishing your day with a sunset on the water or hosting friends, the Sound views from nearly every corner of the property create a stunning backdrop for any occasion. Unbeatable waterfront access, perfect for ocean and bay-side boating. Expansive two-story layout with 2,304 sqft of living space (1,152 sqft per floor). 3 Bedrooms, 2 Bathrooms--ideal for families or a lucrative investment. with a BONUS Building serving as as a Cozy 1 bed/1bath guest quarters for visitors. Opportunities for single family, a MULTI family, a peaceful vacation retreat, or a smart investment, this property offers endless possibilities. Enjoy breathtaking views, a tranquil environment, and the ultimate waterfront lifestyle. Dont let this extraordinary opportunity pass by!

$1,325,000
Key Largo
Pirates Cove   - MM: 98.50
3 Bed, 3 Baths, 1,350 SqFt Days Listed: 204
-9.68% ($142,000) 2 Price Changes : Last Change 60 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Ramp6

Prestigious Pirates Cove - Secluded Lake/Front Basin Home - Direct Ocean & Bay access in just minutes - 3Bed/2 Baths - The Upper Level is a 2 Bedroom/ 1 Bathroom & Lower Unit is a **Grandfathered in designated 1Bedroom/1 Bathroom with a Full Kitchen. Solid Concrete Dock equipped with a 15000 LB boat lift & Separate Jet Ski lift -Also property is Secured by an Electric Gate & Fenced in Yard complete with Shaded Patio area with Pavers and Tropical Landscaping - fish cleaning station & storage. Centrally located near Shopping, Schools & Restaurants.

$1,369,000
Plantation Key
Indian Waterways   - MM: 89.00
2 Bed, 2 Baths, 1,148 SqFt Days Listed: 23
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

$1,389,000
Marathon
Sea Air Estates   - MM: 52.00
2 Bed, 2 Baths, 1,232 SqFt Days Listed: 347
+2.97% ($40,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 75ft.Cut/Natural

New photos coming soon! Welcome to your waterfront oasis in the heart of Marathon, Florida!This beautifully maintained home offers the perfect blend of comfort, convenience, and coastal charm. Recent updates include renovated bathrooms, new bedroom closet doors, all-new bedroom doors with updated hardware, and new impact sliding glass doors and front door--enhancing both style and functionality throughout the property.The circular driveway offers ample parking, while the CBS construction, fully fenced yard, and tropical landscaping create a private island retreat. Inside, the home is sold fully furnished (with a few exclusions) and boasts large bedrooms with custom closets. The spacious master suite includes a renovated en-suite bath, offering a peaceful space to unwind.Enjoy boating and water access from your 75-foot concrete seawall with a step-down, solid cap rock foundation. The dock includes power, water, a swim ladder, and a fish cleaning station--perfect for boating enthusiasts and anglers alike.Relax beneath the homes shaded underneath patio, ideal for outdoor dining or entertaining. A downstairs storage enclosure offers convenient space for water gear and tools.Out back, youll find your private concrete pool surrounded by a sun-drenched deck and a balcony with serene canal views, perfect for morning coffee or sunset cocktails. A metal roof and assumable flood insurance policy provide peace of mind and lasting durability.Inside, enjoy stainless steel appliances, a pool table, and an ice machine, ensuring fun and functionality for both personal use or vacation rental guests. Currently operating as a successful Airbnb, this home is turn-key ready--whether youre looking for a permanent residence, seasonal escape, or investment opportunity.Dont miss your chance to own a slice of paradise in Marathon.

$1,394,000
Big Pine Key
Sands Subdivision   - MM: 31.00
3 Bed, 3 Baths, 1,600 SqFt Days Listed: 126
-0.36% ($5,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 45ft.Concrete

Experience the ultimate Florida Keys lifestyle in this beautiful brand new waterfront home in Big Pine Key! With 45 feet of canalfront concrete seawall, a fish cleaning station, and only four lots in from Florida Bay, this property offers stunning bay and sunset views and easy access to the Atlantic Ocean, perfect for offshore fishing or Florida Bay adventures. Located in a prime area, this home is just minutes away from popular spots like Looe Key Coral Reef, Picnic Island, and Content Keys - offering some of the best boating experiences in the Keys. You can also enjoy often sights of manatees in the canal and catch tarpon right out your back door!The spacious interior features an open-concept layout to treasure the stunning views of the Atlantic Ocean through the oversized windows in the living room/kitchen and dining area with 3 bedrooms and 3 bathrooms. Impact windows and doors throughout provide both security and natural light, creating a bright and airy atmosphere. The kitchen features custom rift-sawn white oak cabinetry, Ocean Blue quartzite island countertop and quartz perimeter countertops, including all bathrooms featuring custom cabinetry and quartz tops, as well as all bedrooms have custom California-style closets.Step outside to the brand new swim spa for relaxation or exercise, and enjoy the added convenience of an outdoor shower. The rooftop deck is the perfect spot to take in even more breathtaking water views and great for entertaining. In addition there is a large storage area downstairs, perfect for all the toys!This home is ideally situated close to local restaurants, parks, and the natural beauty of Big Pine Key, making it a true gem for those seeking the ultimate Florida Keys experience. Dont miss out on this incredible opportunity!

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 04-22-2025.
Back To TopMore Info
Terms / Privacy / Accessibility ADA