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

Total Listings 75
Order By:

$439,000
Big Pine Key
Sands Subdivision   - MM: 31.00
1 Bed, 1 Baths, 441 SqFt Days Listed: 60
-12.02% ($60,000) 2 Price Changes : Last Change 1 Day 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.

$450,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,232 SqFt Days Listed: 48
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 195ft.Concrete

Fix and flip or buy/fix and hold. So much potential with this spacious 3 bedroom waterfront home. Offers about 195ft of dockage for your boat and sits on a large corner lot. Located in a lovely neighborhood with a boat ramp a couple minutes away. Dont miss this opportunity, call today!

$450,000
Big Pine Key
Tropical Bay   - MM: 30.50
2 Bed, 2 Baths, 654 SqFt Days Listed: 126
-14.29% ($75,000) 2 Price Changes : Last Change 27 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.

$479,999
Big Pine Key
Sands Subdivision   - MM: 31.00
2 Bed, 2 Baths, 1,253 SqFt Days Listed: 147
-12.57% ($69,001) 9 Price Changes : Last Change 7 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome to this Key West-style home located on Big Pine Key! Situated on a generous 7500 square-foot fully fenced lot, this property offers ample space for parking and storage, making it a perfect island retreat for those looking to escape the hustle and bustle. As you step inside, youll be greeted by the cozy charm of two bedrooms and a well-appointed bathroom, providing a comfortable living space. The highlight of this home is the spacious upstairs loft, complete with three built-in twin size beds, ideal for accommodating guests or creating a relaxing sanctuary for yourself. For added convenience, the property features an outdoor shower, perfect for rinsing off after a day of island activities, and a storage area to keep your belongings organized. The loft also offers a unique feature--an exit leading to the rooftop that provides stunning views of the open water, perfect for enjoying the island breeze and picturesque sunrises. Conveniently located approximately 30 miles from Key West and 25 miles from Marathon.

$550,000
Big Pine Key
Sands Subdivision   - MM: 31.00
2 Bed, 2 Baths, 816 SqFt Days Listed: 247
-5.17% ($30,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Florida Keys simple living can be yours in this Big Pine Key pool home. Nestled in the neighborhood, yet conveniently located to shopping and other amenities. An open concept with cathedral ceiling in Living, Dining and Kitchen areas. A laundry closet sits at one end of the kitchen and houses the washer and dryer. Off main living area there is a nice porch on the front side of this home, and is a great spot to relax. Exterior of property is encompassed by tropical fruit plants and a full fence. In your back yard you can enjoy a gorgeous pool, 365 days a year. Pool is concrete and equipped with both heater and chiller. The adjacent lot and lots behind home are county owned so no future building. Within walking distance is the Big Pine Community Park, and boat ramp is only a few minutes away. Have the this Florida Home be yours, where you can enjoy both indoor and outdoor living.

$559,000
Big Pine Key
Sands Subdivision   - MM: 31.00
3 Bed, 3 Baths, 1,431 SqFt Days Listed: 47
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.

$574,000
Big Pine Key
Palm Villa   - MM: 30.50
2 Bed, 2 Baths, 816 SqFt Days Listed: 39
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

NEW PRICE! Owner occupied 2 bedroom CBS home boasts a NEW Roof, New Control Panel, tile floors throughout and freshly painted walls, creating a clean and modern ambiance. The kitchen features brand new appliances, including a fridge, microwave, & oven. A spacious 10 x 20 screened porch offers the perfect spot to enjoy the outdoors, whether youre sipping your morning coffee or relaxing in the evening breeze. The property sits on a nearly 7,000 sq. ft. lot, complete with a permitted fence and a 10 x 12 storage shed for all your storage needs.Local amenities enhance the appeal of this home, with world-class fishing and diving spots just minutes away. You can enjoy a meal at the famous No Name Pub, and find everything you need at nearby supermarkets and local stores. The area also offers beautiful walking and biking paths, making it easy to explore the natural beauty of Big Pine Key. This home provides a perfect blend of tranquility and convenience, making it an ideal choice for both weekend retreats and year-round living. Dont miss out on the opportunity to make this delightful property your own! Plenty of parking for autos, boat or RV!

$575,000
Big Pine Key
Sands Subdivision   - MM: 31.00
3 Bed, 3 Baths, 988 SqFt Days Listed: 129
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

OPEN HOUSEMon. 12/23/24 830am-1030amWhether youre looking for a place to call HOME or a GET AWAY to retreat to. Charming 3-bedroom home with open floor plan on a double lot 50 X 200 (10,000 sq. ft.) in Big Pine Key. Front lot is fenced, back lot is not. Storage shed. Home is move in ready and can close quickly. New appliances in the home. Led lighting and tankless water heater. Home is Conveniently located, with nearby community park on Bogie Channel offering water views. Tennis courts, basketball court, baseball field, bocce, skateboard park, racquetball, walking/exercise trail. Easy bike ride to get around town if you like. Public bus transportation offered. Nearby Boat ramp at Spanish Harbor off US1 with quick Gulf and Atlantic access. Bahia Honda State park 10 minutes away. Key West approx. 30 miles. Marathon approx. 20 miles. Miami International approx. 2.5 hours. Ins quote for primary residence approx. $9418.K flood, wind and homeowners. Has openings discounts and some roof discounts. Could be less with higher deductibles. Easy to show. No Homeowners association, Not leased land. Has been connected to central sewer. NO TRESPASSING!

$599,000
Big Pine Key
Palm Villa   - MM: 30.50
3 Bed, 3 Baths, 1,288 SqFt Days Listed: 7
Single Family - Active - 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!

$634,900
Big Pine Key
Doctors Arm   - MM: 30.50
3 Bed, 3 Baths, 1,080 SqFt Days Listed: 107
-5.24% ($35,100) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Davit Pads50f

Updated CBS 3 bedroom, 1 bath canal-front home situated in the desirable Doctors Arm neighborhood of Big Pine Key. Enjoy direct, bridge-free access to open water. The property includes approval for a boat lift by the Dept of the Army Corp of Engineers, which can be transferred to the new owner.This CBS home has been tastefully updated, featuring stainless steel appliances, new electric service, an on-demand hot water heater, impact-resistant windows and doors, and a durable metal roof. The interior is bright and welcoming. Just inside the front door is a nice sized area that would be a perfect TV room along with one bedroom. Just up a few steps to the upper level is more living space with room for a dining table. Just down the hall are two bedrooms and a full updated bathroom.The spacious backyard boasts a spacious deck with an outdoor shower, offering ample space for a pool and plenty of room to relax or entertain.

$650,000
Big Pine Key
Wickfield Acres   - MM: 30.50
3 Bed, 3 Baths, 976 SqFt Days Listed: 73
-3.70% ($25,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Imagine driving down a winding dirt road in the Florida Keys! Are you on the lookout for a peaceful and serene slice of paradise in Big Pine? This could be just the place for you! Nestled on a quiet dirt road with only four homes around, youll be surrounded by beautiful conservation land. Picture this: Key Deer wandering through your yard now and then, and the night sky full of stars without any light pollution--how lovely! Situated on just about an acre of lush & tropical grounds, properties like this are a rare find in Big Pine, and its perfectly located! Youre close enough to Key West to enjoy all that it offers, yet far enough away to relish in your own little oasis. Interior and exterior could use a fresh coat of paint.The 3BR/3BA home is ready for you to make it your own! A brand-new metal roof was installed in 2018, and the air conditioning unit was replaced in 2020. The kitchen comes with shiny stainless steel appliances, including a new side-by-side refrigerator, dishwasher, and gas stove. Youll have all the necessities like water and sewer from FKAA and power from Keys Energy. With cathedral ceilings and sliding glass doors, youll love the amount of natural light that fills the space. While the home could use a little refreshing or remodeling, its the perfect canvas for you to create your dream country living getaway. Come and check it out the winding road, your tranquil retreat awaits!

$675,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,131 SqFt Days Listed: 137
-3.43% ($24,000) 2 Price Changes : Last Change 47 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

PRICE REDUCTION!! Priced below $600 per sq ft, this elevated home on Eden Pines is sited on an expansive double lot. Perfect for boaters with the community boat ramp just steps away. This well distributed floor plan home has many desirable features such as open and spacious living area with 11 vaulted ceilings, walk in closet in primary bedroom, jacuzzi tub in primary bath, Stiebel Entron tankless water heater, metal roof, shutters for all windows and doors and windows. In addition, this home comes with a 500 lb jib winch to lift bulky or heavy items upstairs, all porches are IPE wood and have aluminum railings, a downstairs enclosure provides ample storage.Relax on the covered porch surrounded by the tranquil outdoors with mature trees including two producing mango trees. Enjoy convenient covered parking on concrete slab. The additional parcel offers plenty of room for an RV, boat and other storage needs. Lot size total is 10,000 sqft. LOW INSURANCES including flood $512 assumable annual policy! Perfect island oasis with potential to expand with the adjacent lot.Dont miss this opportunity and schedule your private showing today!

$675,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,020 SqFt Days Listed: 87
-3.43% ($24,000) 1 Price Change : Last Change 48 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.

$685,000
Big Pine Key
Sands Subdivision   - MM: 31.00
3 Bed, 3 Baths, 1,272 SqFt Days Listed: 54
-1.44% ($10,000) 1 Price Change : 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.

$689,000
Big Pine Key
Tropical Key Colony   - MM: 30.00
2 Bed, 2 Baths, 1,040 SqFt Days Listed: 13
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Located in the sought-after Tropical Key Colony neighborhood, this 2-bedroom, 2-bathroom home features modern updates with spacious living and exceptional privacy, with two sides of the property protected from future development. The updated kitchen includes stainless steel appliances, quartzite countertops, and generous cabinetry, while vaulted ceilings in the kitchen, living, and dining areas create an airy, open feel. The primary bedroom includes a large walk-in closet and an en-suite bathroom of comfortable proportions, while the stylishly updated guest bathroom enhances the homes appeal. One of the standout features is the expansive 10x26 screened balcony with ceiling fans, offering an ideal space to relax, entertain, and enjoy the tropical breeze. Additional highlights include a downstairs patio, carport, and an oversized 13x14 enclosed storage area. The fenced yard appeals to pet lovers, and the property provides ample space for boat and RV parking. A metal roof installed in 2018 and low, assumable flood insurance further enhance its desirability. Conveniently located just 40 minutes from Key West and 30 minutes from Marathon, this home is a rare gem that must be experienced in person to be fully appreciated. Dont miss your chance to call it home!

$694,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 936 SqFt Days Listed: 66
-0.72% ($5,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip

CBS home on two lots with a county owned lot to the west which means there is a vacant lot on each side of the home. Located on a 50-foot-wide canal with a cut in boat slip. Only a short ride out to open water. Quiet street with lots of privacy, new roof in 2023, fenced yard. Close to shopping, Bahia Honda state park and beach and a short ride to Key West. Neighborhood boat ramp, lots of wildlife as this home is in the National Key Deer Refuge and boarders on the Great White Heron Refuge.

$719,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,353 SqFt Days Listed: 65
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.

$740,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,204 SqFt Days Listed: 183
-7.38% ($59,000) 6 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Motivated Seller! Dont miss this gem in Big Pine Key! Eden Pines neighborhood! This stunning 3-bedroom, 2-bathroom residence offers the perfect blend of modern amenities and island charm. Situated on a spacious 10,000 sq. ft. lot that has ample parking for boat, trailers and a RV. This home boasts an impressive 275 sq. ft. screened-in porch, perfect for enjoying the serene surroundings. The open-concept floor plan ensures a seamless flow between the living, dining, and kitchen areas, making it ideal for both relaxation and entertaining. The kitchen is a chefs delight, featuring stainless steel appliances, gas range, quartz countertops, a mosaic tile backsplash, newer cabinets, pantry, and a farmhouse sink. Whether youre preparing a casual meal or hosting a dinner party, this kitchen has everything you need. The two guest bedrooms are generously sized and share a beautifully updated full bathroom. The primary bedroom is a true retreat with an ensuite bath for added privacy and convenience. Newly painted decking all around the house! Additional highlights of this home include an above ground pool, tankless water heater, rain gutters and generator. Ample storage areas downstairs provide plenty of space for all your belongings. Around the corner a community boat ramp for easy accessibility to launch your boat. Dont miss the opportunity to own this exceptional property in Big Pine Key. Schedule your private showing today and experience the best of island living!

$749,000
Big Pine Key
Sands Subdivision   - MM: 31.00
3 Bed, 3 Baths, 1,400 SqFt Days Listed: 16
Under Constru - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

BRAND NEW UNDER CONST.FOR SALE $749,000.00 WE OFFER OWNER FINANCING! 1400 SQFT 180 MPH RATED 3/2 HOME. ELEVATED ON 10- 6 TALL CONCRETE COLUMNS WITH TONS OF ROOM FOR BOATS, CARS, OR R/V AND ALL THE TOYS. 9 CEILINGS, CROWN MOLDING AND CENTRAL AC. FULLY PEA ROCKED YARD FOR LOW MAINTENANCE. METAL ROOF, HURRICANE WINDOWS AND DOORS, NO SHUTTERS NEEDED. ,STAINLESS STEEL APPLIANCES..$749,000 / $10,000 DOWN PAYMENT. 30 YEAR AMORTIZATION. 8% INTEREST. 5 YEAR TERM. BUYER PAYS ALL CLOSING COSTS INCLUDING PRO RATED TAXES. LETS TALK. OPPORTUNITIES LIKE THIS DONT COME AROUND VERY OFTEN. CALL FOR PRIVATE SHOWING OWNER REALTOR. RIDE BY FIRST AND IF YOU LIKE IT. NO WIND OR FLOOD INSURANCE REQUIRED. ONLY LIABILITY / FIRE INSURANCE. AVAILABLE ON OR BEFORE 4/1/2025

$750,000
Big Pine Key
Tropical Bay   - MM: 30.50
2 Bed, 2 Baths, 1,008 SqFt Days Listed: 257
-9.09% ($75,000) 3 Price Changes : Last Change 72 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 one bedroom one bath cottage offers a tranquil escape on a DOUBLE LOT fenced in yard, 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. Easy, to make the house a 2 bedroom home. 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.

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 01-21-2025.
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