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

Total Listings 385
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$650,000
Big Pine Key
Pine Key Acres   - MM: 30.50
2 Bed, 2 Baths, 1,120 SqFt Days Listed: 47
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Secluded Oasis in Big Pine Key - Surrounded by Preserve Land!Discover unparalleled privacy and serenity in the heart of a pristine pine wood preserve. This unique 2-bedroom, 1-bathroom home is nestled on a sprawling 38,768 sq. ft. lot, completely surrounded by protected land--ensuring no future development and an uninterrupted natural setting.Wildlife lovers will delight in frequent visits from Key deer, while outdoor enthusiasts will appreciate the expansive space, offering plenty of room for a pool or a lush tropical retreat.Inside, the home features bamboo kitchen cabinets paired with stunning granite countertops, and an updated bathroom for modern comfort. Step outside onto the IPE decking, a durable and elegant touch perfect for enjoying the peaceful surroundings. Multiple fruit trees in the yard add to the charm of this private oasis.Located in the heart of Big Pine Key, youre just minutes from shopping, dining, and all the conveniences you need--while still feeling worlds away from the hustle and bustle. With some TLC, this home presents an incredible opportunity to build equity in one of the most tranquil settings in the Florida Keys.Priced to sell! Vacation rentals allowed, must apply for permit. Some of the fruit trees on site include, hog plum, guava, Barbados cherry, sour Sop tree, custard apple, and mirranga, as well as mature coconut trees and dogwoods.

$655,000
Sugarloaf Key
Indian Mound Estates   - MM: 19.50
2 Bed, 2 Baths, 1,129 SqFt Days Listed: 126
-6.29% ($44,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Nestled in a quiet and charming neighborhood on Sugarloaf Key, this beautifully remodeled 2-bedroom, 2-bathroom home offers a perfect blend of modern updates and coastal charm. With plenty of natural light throughout and crown molding accenting every room, this home feels both elegant and welcoming. The kitchen features newer, stainless steel appliances and stylish finishes, making it ideal for both everyday meals and entertaining. The spacious primary bedroom boasts a large, updated en suite bathroom. The second bedroom and additional bath are equally well-appointed, making this home perfect for both family living and hosting guests. Located just down the street from a private neighborhood boat ramp that can only be accessed with a resident key, this home offers easy access to the crystal-clear waters of the Florida Keys. The large yard provides plenty of room for trailer storage, so you can easily store your boat, RV, or other toys. Theres also ample space to add a pool, creating your oasis in the heart of the Keys. Built with durability in mind, the home features impact windows, a metal roof, insulation in the attic, and hurricane shutters for added peace of mind and protection from the elements. This combination of energy efficiency and storm preparedness ensures that you can enjoy both comfort and security in your new home. Whether youre relaxing in the cozy interior or spending time outside, this home offers the perfect spot to unwind and enjoy the laid-back Keys lifestyle. Dont miss the opportunity to own this turnkey gem in a prime location!

$674,888
Key Largo
Buttonwood Shores   - MM: 100.00
3 Bed, 3 Baths, 1,699 SqFt Days Listed: 142
-3.57% ($25,012) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Immaculately maintained 3-bedroom, 2-bath concrete home on a beautifully landscaped oversized lot. This home boasts an open floor plan, ideal for entertaining, with spacious rooms and tasteful updates throughout. Ample parking and storage for your water toys add convenience, while the fenced backyard is perfect for BBQs with family and friends. Nestled in a fantastic neighborhood, this home offers both charm and accessibility to everything you need.**Home has assumable flood policy. **Property is covered by a premium American Home Shield warranty

$675,000
Big Pine Key
Sands Subdivision   - MM: 31.00
3 Bed, 3 Baths, 1,272 SqFt Days Listed: 145
-2.88% ($20,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

This property is a true delight. This turn key 3-bedroom, 2-bath home in a nice neighborhood. Main bathroom offers a relaxing Jacuzzi tub, while the kitchen features elegant granite countertops and modern stainless steel appliances. This home offers the luxury of marble tile flooring and carpet throughout the bedrooms. Fenced in backyard is the perfect place to unwind, entertain or simply enjoy the Florida Keys lifestyle. Room to add a refreshing pool to complete your tropical retreat. 336 square foot enclosure downstairs and lots of room in the attic space. The home is a few blocks from the local boat ramp and community park. Dont miss the chance to make this your very own home in paradise.

$675,000
Summerland Key
Snug Harbor Subdivision   - MM: 25.00
1 Bed, 1 Baths, 1,024 SqFt Days Listed: 83
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp38ft.Concre

BRING A BACK-UP OFFER ~ ITS ALL ABOUT THE LOCATION! CASH ONLY for this old-Keys, fish camp bungalow that was built in 1958 and needs repair or replacement. Just imagine the wonderful fish stories this home could tell! Heres your opportunity to enjoy amazing open water views and deepwater boating in the Lower Keys. Niles Channel provides excellent access to the ocean and back country - one can even see the Niles Channel Bridge from the location which is within walking distance of Tonios Seafood Shack & Tiki Bar. The fenced, 46 x 74 property has a concrete seawall and concrete boat ramp. One bedroom, a full bath and bonus living area are on the ground level; an open living room / kitchen and half bath are in the upper level; An interior spiral staircase connects the two levels, and an exterior staircase leads to the upper level. 512 sq. ft. concrete block ground level is LLF on property record card; 512 sq. ft. frame upstairs is FLA on property record card; metal roof; impact resistant windows upper level; no shutters; no range/oven. Although it has been loved through the years, the house needs lots of TLC. Theres a separate shed for storing fishing and dive gear. Hooked up the municipal sewer. Cash offers only. Just imagine what the future holds! ***DO NOT WALK PROPERTY without listing agent. ***

$675,000
Marathon
N Marathon Shores   - MM: 51.50
3 Bed, 3 Baths, 1,277 SqFt Days Listed: 247
-12.22% ($94,000) 3 Price Changes : Last Change 12 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

CHARMING SINGLE FAMILY HOME ON A HUGE FENCED LOT in a wonderful residential neighborhood. Very close to the boat ramp on Dodge Lake so launching your boat is very accessible. This 3 bedroom 2 bath home has a nice kitchen, updated bathrooms, and convenient laundry. There is a storage shed on the rear fence in the back yard. Plenty of play space for the kids and dogs to run around.

$678,000
Marathon
Sunset Bay   - MM: 56.00
3 Bed, 3 Baths, 1,152 SqFt Days Listed: 42
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome home to this gently used and meticulously maintained home in Sunset Bay on Grassy Key. Lucky for you, your impact windows and doors (2019) and your metal roof have already been installed. Enjoy relaxing on the generous, covered front porch enjoy natures bounty of birds and wildlife on the lake/salt pond. This stilted GEM has 3 bedrooms for you and your family to enjoy home in the Keys. The primary suite has private deck and nice walk-in closet. The larger guest bedroom also has walk-in closet with build-ins for extra storage. TONS of parking for multiple vehicles, RV, Boat / Jetski trailer and more. Located in Sunset Bay, a wonderful, friendly community and only a brief 3 block walk takes you to Sunset Bay Park, where friends and neighbors enjoy the nightly sunsets and fishing or just relaxing on the community dock. Now, is the time to come Home to 220 Kyle in Sunset Bay on Grassy Key!

$699,000
Key Largo
Key Largo Park   - MM: 101.00
3 Bed, 3 Baths, 1,366 SqFt Days Listed: 57
-3.59% ($26,000) 1 Price Change : Last Change 3 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Boat Ramp,None

NEW CONSTRUCTION ...soon to be completed. Combine tranquility with convenience in a vibrant community within close proximity to downtown Key Largo. Private bayfront homeowners park with boat ramp, beach and picnic area is optional to join.This 2 story home offers 3 bedroom 3 bath, possibly a 4th bedroom. Great layout with 1st floor entry with Living area, kitchen & 1 Bedroom 1 Bath down. Internal stairs offers 2/2 plus den. Contemporary finishes, quartz counters, beautiful large porcelain floor tiles. All impact glass, metal roof, stainless steel appliances. Be the first to live here!

$699,000
Key Largo
Riviera Village, Rec Amd   - MM: 104.00
2 Bed, 2 Baths, 1,080 SqFt Days Listed: 117
-10.27% ($80,000) 2 Price Changes : Last Change 5 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome to this recently renovated, charming Keys cottage situated on 3 spacious lots, offering incredible potential for investors or families seeking a tranquil slice of paradise. Located just a few blocks from Key Largo School and within minutes of local amenities, this property is ideally positioned for both convenience and seclusion.This property boasts a private waterfront homeowners park complete with a boat ramp, a serene cove, and 72-hour dockage--perfect for boating enthusiasts. The newer white metal roof provides peace of mind, while the homes interiors have been thoughtfully updated to blend modern comforts with island charm.Step inside to find a bright, airy space with wood-look porcelain tile throughout. The brand-new kitchen is a chefs dream, featuring sleek white Shaker cabinets and stunning quartz countertops. Each bedroom offers a private en suite bathroom, providing ultimate privacy and convenience. Large closets and a generous laundry room ensure plenty of storage space.The property has been brought to full compliance and offers excellent investment potential. Once the lots are no longer combined for tax purposes, you could build up to three homes on the property, making this an outstanding opportunity for development. Whether youre looking for a family retreat or an investment with future growth potential, this property is the perfect canvas.Just two minutes from the iconic Key Largo Stretch and an easy hours drive to Miami, this is an unbeatable opportunity to own a piece of paradise with endless possibilities.

$699,900
Key Largo
Buttonwood Shores   - MM: 100.00
2 Bed, 2 Baths, 1,493 SqFt Days Listed: 111
-11.35% ($89,600) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Hard to find oversized lot - nearly 22,000 sq ft - in Buttonwood Shores in the middle of Key Largo! Unique home with several living/storage areas, each with private entrances opening up lots of possibilities for renovations, or start over with your dream home compound on this .50 acre +/- lot! Plenty of mature, native trees, palms and vegetation onsite. Upstairs offers 2 bedrooms, Den, 2 baths, kitchen, 2 screened porches plus an open air deck. ( seller took out a wall upstairs, currently 1 bedroom and a den). Downstairs youll find a 576 sq ft efficiency apartment with full kitchen and bath; a one car garage/laundry room at 495 sq ft; plus a utility room with 415 sq ft. Each area has a private entrance. This home offers a metal roof and hurricane impact windows.

$699,900
Big Pine Key
Tropical Key Colony   - MM: 30.00
2 Bed, 2 Baths, 1,232 SqFt Days Listed: 38
-3.99% ($29,100) 1 Price Change : Last Change 9 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

This quintessential home is surrounded by 17 parcels of pristine environmental and conservation land, offering nature, privacy, wildlife, and the best tropical living the Keys has to offer. The full-size screened rear porch faces vacant land with swaying palms, tropical vegetation, with key deer grazing below. Enjoy morning coffee or evening cocktails while tropical breezes provide refreshing ocean fragrances. The fully fenced yard offers a spacious area ready for a large pool and tiki hut, with plenty of room for gardening and outdoor living. Covered under-the-house parking for several vehicles and storage and ample space for boats, trailers, or an RV. The house boasts a full wrap-around porch with dual entrances to the screened porch. Enter the open-concept home to the living room, kitchen, and dining area showcased by vaulted ceilings and double sets of French doors offering an abundance of light and greenery. The master suite provides a large walk-in closet and spacious living area with room for a king size bed. The upstairs laundry room offers convenience and additional storage options. Located in a sought-after area of Big Pine, this home is well-built and has low assumable flood insurance and is conveniently situated for easy drivability between Key West and Marathon. Two community boat ramps are within minutes for some of the best boating in the lower Keys. This home is well maintained and ready for you and your friends and family to come experience real Keys living.

$699,999
Big Pine Key
Tropical Key Colony   - MM: 30.00
3 Bed, 3 Baths, 1,184 SqFt Days Listed: 40
-3.45% ($25,001) 2 Price Changes : Last Change 4 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Private & Secluded Home in Coveted Big Pine Key. Discover this beautifully maintained 3-bedroom, 2-bath home tucked away on a quiet street in one of Big Pine Keys most desirable neighborhoods. Designed for comfort and entertaining, this home features an open-concept kitchen with stunning Quartz countertops, a spacious island--perfect for hosting or casual family meals. The expansive living room and formal dining area provide a welcoming atmosphere, while the large master suite offers dual closets and an en suite bath with modern finishes. Both bathrooms boast upgraded fixtures and sleek glass-enclosed showers. Downstairs, youll find a large enclosed space with garage doors, offering covered parking and plenty of room for a workshop, storage, or recreational gear. The oversized, fully fenced lot ensures privacy and provides ample space for an in-ground pool, boat, or RV. Enjoy the best of Florida Keys living in this serene retreat--just minutes from beaches, state park, world-class fishing, and local conveniences of shopping and dining. Dont miss this rare opportunity--schedule your private showing today!

$700,000
Upper Matecumbe Key Islamorada
Coral View   - MM: 81.00
3 Bed, 3 Baths, 2,016 SqFt Days Listed: 195
-26.32% ($250,000) 6 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

This lovely home is classic Keys on the outside, with modern elegance on the inside. Secluded on high ground in the heart of downtown Islamorada, this accommodating three-bedroom, two-bath residence offers abundant space for relaxation and entertainment, including an inviting back porch, surrounded by lush landscaping that enhances the serene atmosphere. The expansive front and back yards provide ample room for outdoor activities and gatherings. Ideally situated, you are within easy walking distance to the beaches, great restaurants, and grocery shopping. Experience the perfect blend of comfort and convenience in this idyllic retreat.

$715,000
Key Largo
Pirates Cove   - MM: 98.50
2 Bed, 2 Baths, 1,292 SqFt Days Listed: 80
-2.72% ($20,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Boat Ramp

Coastal Charm in Key Largo - Modern CBS Home in Pirates Cove Welcome to your dream getaway in the heart of the Florida Keys! Built in 2017, this elevated 2-bedroom, 3-bath CBS home in the desirable Pirates Cove neighborhood offers the perfect combination of modern construction and coastal charm. With 1,292 sq. ft. of living space on two levels, this home features impact windows and doors, a durable metal roof, and an elevated design for peace of mind.Step inside to find a bright and airy open-concept layout, with stylish finishes throughout. The well-appointed kitchen boasts stainless steel appliances, granite countertops, and ample storage, flowing seamlessly into the living and dining areas. Upstairs, the primary and secondary bedrooms each offer ensuite baths, creating private retreats for residents and guests alike. A third full bathroom on the main level adds extra convenience.Nestled on a 2,500 sq. ft. lot, this home is ideal for low-maintenance island living. The Pirates Cove community features a private boat ramp and clubhouse, with a voluntary HOA of just $250 per year. Enjoy the convenience of being just minutes from bayside and ocean access, perfect for boating, fishing, and watersports enthusiasts.Located at Mile Marker 98.5, this home is ideally situated near top dining, shopping, and entertainment options. Savor fresh seafood at The Fish House, Hobos Cafe, or the iconic Alabama Jacks. Pick up local provisions at Key Largo Fisheries or explore boutique shops at nearby Pink Plaza. For outdoor adventures, visit John Pennekamp Coral Reef State Park, Florida Keys Overseas Heritage Trail, or enjoy a sunset cruise from one of the local marinas.With easy access to Miami and Fort Lauderdale International Airports, and the option of Marathon Airport for private travel, this home makes the perfect full-time residence, weekend escape, or investment property. Dont miss your chance to own a slice of paradise in Key Largo! Schedule your pr

$719,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,353 SqFt Days Listed: 156
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 50ft.Concrete

This 3BR spacious canal front home with quick open water access is nestled at the end of a quiet dead-end street. Amidst lush vegetation, this property offers the ultimate sanctuary for those seeking privacy and a connection to the Keys lifestyle. 50ft concrete seawall with 10,000lb boat lift. This home boasts an inviting shaded deck creating the perfect outdoor space for relaxation and entertainment. The homes interior layout boasts almost 1400sqft, including 3 spacious bedrooms, 2 bathrooms, and a bonus room that could be used as an office, workout area, or Florida room. 30AMP hook up.

$719,000
Marathon
N Marathon Shores   - MM: 51.50
3 Bed, 3 Baths, 1,538 SqFt Days Listed: 152
-12.85% ($106,000) 4 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Nestled in a beautiful Marathon Florida neighborhood, this concrete-built gem offers a peekaboo view of the Gulf of Mexico and an unbeatable location. The freshly painted interior and exterior, coupled with recent remodeling, give this home a modern, move-in-ready appeal. The expansive fenced yard is perfect for outdoor activities and offers ample space for future expansion, such as a pool or home addition. A freestanding concrete storage building in the backyard provides additional utility. Enjoy peace of mind with impact windows and doors, as well as PVC plumbing under the home, eliminating concerns about outdated cast iron pipes. Parking is a breeze with plenty of space for cars, trucks, RVs, or trailers. Boating enthusiasts will love the neighborhoods public boat ramp, just around the corner, offering easy access to world-class fishing and diving in the Gulf of Mexico. Conveniently located near Publix, Winn Dixie, Home Depot, Sombrero Beach, Marathon Airport, and an array of restaurants and shops, this home combines comfort, practicality, and Florida Keys charm. Your slice of paradise awaits!

$719,000
Cudjoe Key
Cudjoe Acres   - MM: 21.50
2 Bed, 2 Baths, 855 SqFt Days Listed: 212
-9.56% ($76,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

New Price! PRIME OPPORTUNITY IN CUDJOE KEY! Elevated home boasts 2 spacious bedrooms and 2 recently renovated baths. Just off famous US1 this property is sited on a spacious lot with plenty of versatility! Zoning is Suburban Commercial (SC) which may allow for a Special Vacation Rental Permit. Perfect property for an owner occupier or investor. Wraparound porch offers sunrise and sunset views with a deck off kitchen/primary suite and another deck off living room along with two sets of stairs with access to yard and parking. Bonus non-confirming space is ideal for a home office or commercial use. Property offers ample off-street parking for your RV, autos, and boat. The large lot is fenced and private with room for a pool or perfect as is with the tropical landscape and low maintenance ground covering. Owner occupied and well maintained, this property is move in ready. Hurricane shutters, metal roof, secluded private lot, & custom outdoor shower make this a perfect Keys oasis. Building up or adding a rooftop deck would give you amazing water views. Property has a tankless water heater and sheds for extra storage. Great location in the Florida Keys with nearby community boat ramp, dining and beaches. Bahia Honda State Park just 17 miles and Key West 19 miles.

$725,000
Big Pine Key
Tropical Bay   - MM: 30.50
2 Bed, 2 Baths, 1,008 SqFt Days Listed: 348
-12.12% ($100,000) 4 Price Changes : Last Change 6 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits188ft.

Welcome to our cozy retreat nestled on Big Pine Key. This charming two bedroom one bath cottage offers a tranquil escape on a DOUBLE LOT fenced, providing privacy and security. Enjoy the picturesque waterfront views from your own back yard. Florida room with large impact windows to capture the water views. Impact windows through out. Approximately 273 feet of concrete seawall with davits, Small garage for extra storage. Property is also 100 % handicap accessible. This home is your gateway to laidback island living. Make offer!!

$725,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 884 SqFt Days Listed: 131
-12.11% ($99,900) 4 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: BasinConcrete

DIRECT ACCESS to the beautiful FLORIDA KEYS - Eden Pines in Big Pine Key. This delightful waterfront home with New hardy plank siding features two bedrooms and one bath upstairs with an open concept layout. Theres also a bonus room that offers flexible options, like working from home or pursuing hobbies, while enjoying many comforts! Priced below appraisal.Some highlights include gracious water views, tropical landscaping, serene lighting, and a canal with ocean access. concrete seawall, and a personal boat basin for safety and security. Youll also find impact windows with a 145 mph wind load capacity. This sweet bungalow features a remodeled- redesigned specialty chefs kitchen with a gas stove, quartz counters, farm sink and sensational, tropical views.This captivating retreat home can sleep six.. Did someone say...Perfect Airbnb!Perfect Keys Home or investment Vacation Rental. Location-Location! On the water! Buyer to verify

$725,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,039 SqFt Days Listed: 99
-7.40% ($57,900) 1 Price Change : Last Change 49 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Fixed BridgeCut/Natu

SITUATED ON A 50 FT. WIDE CANAL, this updated 3 bedroom / 2 bath home offers very good boat access to Pine Channel, the Atlantic and back country. The great room is bright and airy with a cathedral ceiling, south facing picture window and French doors that lead to the covered porch overlooking the canal. Updates include impact-resistant windows and doors, new stainless steel kitchen appliances, recent vinyl plank flooring and vanities; 2018 metal roof; the water heater is less than a year old. The 5,000 sq. ft. lot offers 50 ft. of canal-frontage and the nearby public boat ramp couldnt be more convenient! Eden Pines Colony is a friendly neighborhood where the Key deer roam and bike paths, shopping, parks, banks and more are within easy reach on the island.

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.
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