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Florida Keys 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 Florida Keys homes for sale below are on the gulf side / bay side.

Total Listings 385
Order By:

$419,000
Big Pine Key
Sands Subdivision   - MM: 31.00
1 Bed, 1 Baths, 441 SqFt Days Listed: 151
-16.03% ($80,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Concrete

Per Seller: Boaters Paradise! 3 minutes to open water with the ability to dock almost any big boat or multiple boats here! 50 of sea wall and there is 25x50 feet of owned sea bed so the potential to moor boats here is amazing. Huge catamaran sail boat or multiple center consoles backed in. Would be a great base for a fishing charter. This is a cozy, solid built home, not a manufactured or mobile home. No HOAs and save on insurance! Many parks and trails nearby. Wonderful, very quiet community and great neighbors. Come see what Big Pine has to offer: fishing, lobstering, kayak 10 minutes to sand bar from your house and watch turtles and dolphins! See manatees, endangered key deer and a variety of bird species. Amazing place to live! Make the most of Keys living! There is plenty of space for storage with a shed and place to park for a RV, boat trailer or multiple vehicles. Charming outdoor area for lounging and entertaining. Relax with a line in the water. Efficient and well equipped kitchen. Bathroom with shower and washer/dryer, on-demand water heater. Everything you need and nothing that you dont. Buy now with the ability to build in the future.

$425,000
Big Pine Key
Tropical Bay   - MM: 30.50
2 Bed, 2 Baths, 654 SqFt Days Listed: 217
-5.56% ($25,000) 1 Price Change : Last Change 2 Days Ago
Half Duplex - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 37ft.Concrete

Nestled at the end of a peaceful dead-end street, this well maintained 2-bedroom, 1-bath home offers both privacy and serene water views. The property backs onto a picturesque canal that is fully maintained by the HOA, ensuring a low-maintenance outdoor lifestyle.Outside, enjoy the tranquil canal from your backyard, ideal for morning coffee or evening sunsets. Located in a family-friendly community, this home offers easy access to Bogie Channel, local amenities, parks, and the loveable Key Deer. This is a rare opportunity to own a piece of paradise and quiet waterfront living.

$439,000
Marathon
Key Colony Subdivision   - MM: 53.00
2 Bed, 2 Baths, 728 SqFt Days Listed: 37
Half Duplex - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Charming 2/1 Half Duplex in Marathon, FL - Prime Location! 🌴 Florida Keys!This nicely remodeled 2-bedroom, 1-bath half duplex is the perfect long-term rental investment, or personal retreat. Located in a 7-night rental zone, it offers strong income potential and is one of the most affordable 2-bedroom homes in Marathon. Built with concrete block construction, a metal roof, and impact windows, this home is built to last. The tropical yard is filled with fruit trees and has plenty of space for a garden, plus a storage shed for all your outdoor gear. With ample parking, theres room for cars, boats, or a small RV.This home is in a prime location, just a short walk to restaurants, shopping, a pharmacy, and other conveniences. The Gulf of America is only steps away, offering serene waterfront views. For boating and fishing enthusiasts, the city boat ramp is just minutes away, providing easy access to both the Atlantic and the Gulf. Whether youre into world-class fishing, diving, or snorkeling, this home puts it all within reach. Dont miss this chance to own a turnkey Keys retreat at an unbeatable price--call today for a showing!

$450,000
Cudjoe Key
Cutthroat Harbor Estates   - MM: 23.00
2 Bed, 2 Baths, 980 SqFt Days Listed: 19
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

This sale is for three 5000 square foot lots. Two are undeveloped (bilders points TBD) One lot has an abandoned house so it is ROGO exempt.

$455,000
Marathon
Key Colony Subdivision   - MM: 53.00
1 Bed, 1 Baths, 690 SqFt Days Listed: 329
-9.00% ($45,000) 4 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Fully remodeled 1/1 CBS home in the Florida Keys. Tile flooring throughout, SS appliances, washer/dryer, impact windows and doors, tankless water heater. Marathon allows rentals as little as 7 days. Fenced backyard with screened porch for privacy and entertainment, BBQ area and plenty of parking in front and on side of property with a pull through front and rear gate to facilitate boat and trailer parking. Close to shopping, restaurants and boat ramps. No Association. Come enjoy the Keys lifestyle!!

$460,000
Big Pine Key
Tropical Key Colony   - MM: 30.00
2 Bed, 2 Baths, 1,187 SqFt Days Listed: 72
-16.36% ($90,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Nestled in the highly sought-after Pine Channel Estates neighborhood, this 2-bedroom, 2-bath home offers incredible potential for those looking to put their personal touch on a Florida Keys retreat. Though its a fixer-upper, the property boasts a spacious layout and plenty of room for improvement, making it the perfect opportunity to create your dream home in paradise.The large lot offers ample space for outdoor activities, gardening, giving you endless possibilities to enhance the property. In addition, theres plenty of storage to accommodate all your needs.Situated in a peaceful, serene location, the home provides canal views that will make every day feel like a vacation. Youll be just a stones throw away from the water, perfect for those who enjoy boating or simply relaxing by the shore. The famous Key Deer, a unique and rare sight in the Keys, can often be spotted wandering nearby.Whether youre looking for a vacation getaway, a rental investment, or a personal sanctuary, this property is a blank canvas waiting for the right buyer to unlock its full potential. Dont miss out on the chance to own a piece of paradise in the Florida Keys!

$475,000
Big Pine Key
Sands Subdivision   - MM: 31.00
4 Bed, 4 Baths, 1,620 SqFt Days Listed: 9
Mobile Home - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Investment opportunity on 10,000 sq. ft. double lot near the Big Pine Community Park; the location offers easy access to US1, local shopping and more; Marathon and Key West are within easy reach. **DO NOT WALK THE PROPERTY WITHOUT APPOINTMENT** 2 units, 2 tenants; pets on premises. 1,060 sq. ft. mobile home has 3BD/2BA, exterior wood siding; interior has been updated. CBS garage has 560 sq. ft. 1BD/1BA frame unit above it; needs updating. Both units are tenant-occupied. 2 electric meters, 1 water meter; taxed as a duplex with double Solid Waste and Cudjoe Wastewater on property tax bill. Hooked up to sewer. Shown by advance appointment only to accommodate tenants schedules; proof of funds required. No sign on property.

$475,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
5 Bed, 5 Baths, 2,900 SqFt Days Listed: 182
-4.81% ($24,000) 1 Price Change : Last Change 2 Days Ago
Fractional Ow - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 55ft.

New CO-OWNERSHIP opportunity: Own 1/8 of this professionally managed, turnkey home. Swaying palms and a gracious front entry leave no doubt that relaxation awaits in this new construction Florida Keys home. The 5-bedroom, 3.5-bathroom home is along a canal in sought-after White Marlin Beach. The open-concept main floor has soaring ceilings, oversized windows and glass doors connecting the living space to the pool and waterway beyond. The bright gourmet kitchen features JennAir appliances, two sinks and spacious cabinets. A bay window in the dining area serves up a pool view. The main floor primary bedroom includes a custom closet and opens to the pool and patio. The main bedroom upstairs has a large closet and a Jack & Jill bath leading to another guest bedroom. With two additional bedrooms, the home easily accommodates family and friends. The home comes fully furnished and professionally decorated. There will be six 1/8 shares and one 1/4 share sold.

$479,000
Key Largo
Key Largo Trailer Village   - MM: 101.50
2 Bed, 2 Baths, 1,453 SqFt Days Listed: 50
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Boat Ramp

Rare opportunity in Key Largo! This 5,300 sqft lot is ROGO-exempt, offering a hassle-free path to building your dream home in the Keys. The existing manufactured home needs TLC--renovate or remove and build new! Zoned for single-family, mobile, or manufactured homes, giving you endless possibilities. Seller is open to negotiate providing plans to fast-track your project. Act now--prime lots like this move fast!

$485,000
Key Largo
Lake Surprise Estates   - MM: 106.00
4 Bed, 4 Baths, 1,344 SqFt Days Listed: 181
-11.82% ($65,000) 2 Price Changes : Last Change 2 Days Ago
Mobile Home - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Charming 4-Bedroom Home - Perfect for Families or Investors! Discover this clean and welcoming 4-bedroom, 1-bath manufactured home on a spacious 5,000 square-foot lot in a family-friendly neighborhood. Large Fenced-in and Shady Yard! Whether youre a first-time homebuyer, an investor looking for workforce or student housing, or simply seeking a cozy place to call home, this property offers endless potential. Families will love the proximity to schools, parks, local shopping, and restaurants, while investors will appreciate the high rental demand with the CFK campus just minutes away. The homes location is ideal for commuters or weekend trips, a quick trip from Miami and close to popular tourist attractions. With its affordable price and versatile use, this home is a perfect starter home, the chance to build your Florida Keys dream home, or an income-generating opportunity. Dont miss out on this gem! This wont last long at this price!!

$490,000
Key Largo
Pirates Cove   - MM: 98.50
1 Bed, 1 Baths, 584 SqFt Days Listed: 13
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Boat Ramp

Relaxing Old Keys living in the heart of Key Largo! Ready to live the island life without the paradise price tag? The neighborhood boat ramp with bay, intercoastal waterway and ocean access is just across the street, and theres also a clubhouse and a quaint neighborhood beach to wade directly into the bay. The area all around the neighborhood on the bayside also offers great kayaking, paddleboarding and back country fishing. The highlights of this Keys classic concrete block home are the warm and inviting tongue and groove wood ceilings plus the new metal roof. Outside is plenty of room in the yard for your boat and water toys. The Pirates Cove neighborhood is also close to all the most popular restaurants and bars by land or sea, and it also offers plenty of nearby shopping opportunities and an easy one hour drive to the mainland (if you must!) Call today... this one wont last!

$499,000
Big Pine Key
Sands Subdivision   - MM: 31.00
2 Bed, 2 Baths, 754 SqFt Days Listed: 40
-4.95% ($26,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Boat Ramp

Make this Charming Keys cottage your little piece of paradise today. Complete Remodel 2 Bedroom 1 bathroom with a bonus office/guest room opening to a large screened patio and spacious back yard. This Home is a true Conch home Constructed with Miami Dade Pine originally built in Key West then moved to Big Pine to join the first few homes built on. the Island. Impact doors, new shutters, new roof, Tankless water heater, ample off street parking for all your toys! Bring your RV, Boat and jet skis and enjoy the tranquil privacy this home has to offer. Minutes to the Big Pine Shopping center and dining. Short Trip to Bahia Honda, the reef for incredible snorkeling or go South to Enjoy Everything Key West has to offer. Seller Motivated and open to all reasonable offers.

$524,777
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,506 SqFt Days Listed: 76
-16.14% ($101,000) 2 Price Changes : Last Change 16 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Fixed Bridge

Charming 2-Bedroom Cottage with Serene Privacy in Big Pine Key. County owned lots to the North, South, and West ensures privacy.Nestled in the heart of Big Pine Key, this 2-bedroom, 1.5-bathroom cottage offers the perfect combination of tranquility, privacy, and natural beauty. With no development allowed to the west, youll enjoy an extra layer of seclusion, allowing you to fully embrace the surrounding wildlife and peaceful atmosphere.A short walk from the renowned Blue Hole, one of the areas most sought-after natural attractions, this home is ideal for nature lovers and those seeking a relaxed lifestyle in the Florida Keys. Whether youre an avid boater or just love the water, this property boasts convenient access for boats with up to a 3ft draft and 9ft bridge clearance, giving you easy access to the vibrant waters of the Keys.Inside, youll find a cozy, cottage-like space full of potential. The home offers the opportunity to add your personal touch and TLC, transforming it into the perfect retreat. The peaceful surroundings, coupled with the warm, inviting vibe of the home, make this the ideal spot to relax and unwind.If youre seeking a slice of paradise where you can create your dream home, this is the perfect opportunity. Come and see for yourself why Big Pine Key is one of the best-kept secrets in the Keys!

$525,000
Key Largo
Sunset Acres   - MM: 93.00
3 Bed, 3 Baths, 1,584 SqFt Days Listed: 87
-7.73% ($44,000) 2 Price Changes : Last Change 2 Days Ago
Mobile Home - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome to this spacious 3-bedroom, 2-bathroom home offering 1,584 sq ft of living space on a DOUBLE LOT. Situated in the desirable Sunset Acres community. This home features a versatile bonus office and a workshop, perfect for hobbies or additional storage.The heart of the home is the open-concept kitchen with a chefs gas range, seamlessly flowing into the living and dining areas. Relax and unwind in the screened-in patio. Take advantage of the under-roof carport on rainy days.Recent updates include a 2020 roof with a transferable warranty and a 2023 AC unit. Outside, youll find a private, fenced backyard with an additional shed, providing plenty of storage. Theres ample parking for your boat or other water toys. As part of the Sunset Acres community, youll enjoy a lighthouse and a beautiful beach area, where neighbors gather to watch breathtaking sunsets together.Dont miss out on this opportunity to live in a peaceful, welcoming community!

$529,000
Marathon
Grassy Key   - MM: 58.90
2 Bed, 2 Baths, 874 SqFt Days Listed: 17
Half Duplex - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome to 57538 Bailey St! This tastefully decorated 2-bedroom home is a gem. The modern kitchen features stainless steel appliances, including a dishwasher, microwave, and range. Upstairs, enjoy the convenience of central A/C and an in-unit washer/dryer. The downstairs area is a tropical oasis, complete with a fenced yard, tiki hut, hot tub, and cozy sitting area--perfect for entertaining. Nestled just a short drive from Marathons vibrant offerings: Shopping, aquatic adventures, and dining options. To explore this inviting property in person, call today!

$535,000
Key Largo
Key Largo Park   - MM: 101.00
2 Bed, 2 Baths, 704 SqFt Days Listed: 15
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Boat Ramp

Tastefully updated 2 bed, 2 bath concrete home on a double lot! All above flood and located in an X-zone. Situated in the highly desirable neighborhood of Key Largo Park, this home offers access to the private Buttonwood Sound Club, featuring a bayfront beach and boat ramp-perfect for catching sunsets, getting out on the water, and enjoying the salt life.Set on a spacious double lot, this home features a newer metal roof, all impact windows and doors, and a large, fully fenced yard that offers both privacy and space. Inside, youll find a beautifully updated interior thats totally move-in ready, with new flooring, a modern kitchen featuring a stylish backsplash, brand-new stainless-steel appliances, and granite countertops. Both bathrooms have been tastefully renovated, and the home also includes a new A/C, hot water heater, and updated electrical, plumbing, and more.The expansive backyard deck and patio are ideal for outdoor entertaining, and the detached concrete workshop provides the perfect space for hobbies or extra storage. Enjoy street-to-street access with double swinging gates, offering plenty of room to park an RV or large boat trailer. Theres even a poured foundation in the backyard, ready for a potential addition if more space is needed in the future.Whether youre looking for a primary home, a weekend getaway, or a low-maintenance downsizing option, this home checks all the boxes. Affordable, turnkey, and full of charm. Come live the island life in the heart of Key Largo! Call today.

$539,000
Big Pine Key
Sands Subdivision   - MM: 31.00
3 Bed, 3 Baths, 1,431 SqFt Days Listed: 138
-3.58% ($20,000) 2 Price Changes : Last Change 22 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Situated on Big Pine Key, this house offers a blend of functionality and charm in a serene environment. Located minutes from shops, stores, and local conveniences, it provides an excellent balance of practicality and tranquility. Featuring a large living space that serves as the central hub for daily living. Its open design allows natural light to flow through, creating a bright and inviting atmosphere. The layout includes two guest bedrooms, each offering generous closet space for storage. These rooms are perfect for accommodating visitors or repurposing as a home office or creative space. The primary bedroom serves as a peaceful retreat, offering privacy and comfort. Its spacious design provides plenty of room for a personalized setup to suit your needs complete with an en suite bathroom. The kitchen is equipped with ample cabinetry, ensuring plenty of room for storage and organization. The outdoor space is a highlight of the property, featuring a well-kept yard that adds to the homes overall charm. This house is a blank canvas waiting for someone to transform it into a dream home. With its solid structure, practical features, and excellent location, it provides a foundation for endless possibilities. Embrace the opportunity to design a space that reflects your style and enjoy the unmatched charm of Big Pine Key.

$549,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,020 SqFt Days Listed: 178
-21.46% ($150,000) 4 Price Changes : Last Change 17 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip

Nestled within the peaceful surroundings of the Key Deer Refuge, this charming 2 bedroom, 1 bathroom canal-front home offers a unique blend of nature, privacy, and easy access to water adventures. The homes inviting, light-filled interior embraces the essence of a classic Keys residence, with spacious, well-designed rooms. The open living area, filled with natural light from large windows, seamlessly connects to the kitchen, creating a warm, welcoming space perfect for both entertaining and quiet relaxation. Tropical light filters through every corner, framing serene canal and garden views that enhance the homes tranquil ambiance. Each bedroom offers ample space for rest and rejuvenation, while a bonus room provides flexible options as a cozy home office, additional storage, or hobby space. For those who love the water, this property is a true paradise. A private on-site boat ramp allows for convenient small-vessel access, while a larger neighborhood boat ramp around the corner provides even more options for boaters. Just minutes from open water, the home is ideally situated for enjoying the Keys renowned fishing, snorkeling, and diving. The neighborhood is equally appealing, combining a quiet setting with access to all essential conveniences. Nearby, youll find local shopping, popular restaurants, and vibrant bars, plus the Big Pine Community Park for outdoor recreation. The Key Deer Refuge across the street creates a natural buffer, adding privacy, preserving the local beauty, and offering occasional sightings of the charming Key Deer.This home perfectly balances a tranquil, island lifestyle with modern comforts, making it an ideal place for anyone seeking the best of Florida Keys living.

$549,000
Big Pine Key
Palm Villa   - MM: 30.50
3 Bed, 3 Baths, 1,288 SqFt Days Listed: 98
-8.35% ($50,000) 1 Price Change : Last Change 23 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome to your dream retreat nestled in the heart of Big Pine Key, where tranquility and sophistication meet. This stunning 3-bedroom, 2-bathroom residence is an ideal sanctuary for those seeking a blend of modern convenience and the relaxed charm of the Florida Keys. From its lush landscaping to its thoughtfully designed interiors, every detail of this home exudes comfort and style, promising a lifestyle of ease. As you approach the property, youre greeted by an immaculately landscaped yard, featuring a mix of native tropical plants and vibrant greenery. The lush surroundings not only enhance the homes curb appeal but also create a private oasis that perfectly complements the natural beauty of Big Pine Key. Whether youre relaxing on the front porch or exploring the backyard, the outdoor spaces invite you to immerse yourself in the serenity of island living. Step through the front door and into the main living area, where stained wood ceilings are an instant highlight, adding warmth and character to the space. The kitchen features stainless steel appliances and ample cabinetry. The primary bedroom serves as a private retreat, offering backyard access, generous closet space, and an en suite bathroom for added convenience. Two additional bedrooms provide flexibility for guests, family, or hobbies, while cozy study ensures a quiet workspace. Outside, the backyard is a tropical paradise, perfect for relaxing, gardening, or entertaining. The propertys lush landscaping offers both beauty and privacy, creating your own serene getaway. Located in the heart of Big Pine Key, this home provides easy access to local parks, beaches, and the unique charm of the Florida Keys. Dont miss your chance to make this island retreat your own!

$549,000
Key Largo
Pirates Cove   - MM: 98.50
2 Bed, 2 Baths, 840 SqFt Days Listed: 20
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Key Largo ground level CBS home in an X flood zone! This charming residence features two bedrooms, one bathroom, and includes a garage! The metal roof was installed in 2018, along with impact windows and a door in 2012, and granite countertops in the kitchen. The cozy yard requires minimal upkeep and offers space for a trailer. Conveniently located near the clubhouse, boat ramp, and private community beach, perfect for launching kayaks or paddle boards, as well as providing a spot for your furry friend to enjoy a swim!

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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