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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.

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Total Listings 88
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$419,000
Big Pine Key
Sands Subdivision   - MM: 31.00
1 Bed, 1 Baths, 441 SqFt Days Listed: 191
-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: 257
-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.

$475,000
Big Pine Key
Sands Subdivision   - MM: 31.00
2 Bed, 2 Baths, 754 SqFt Days Listed: 80
-9.52% ($50,000) 2 Price Changes : 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.

$475,000
Big Pine Key
Sands Subdivision   - MM: 31.00
4 Bed, 4 Baths, 1,620 SqFt Days Listed: 49
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.

$515,000
Big Pine Key
Sands Subdivision   - MM: 31.00
3 Bed, 3 Baths, 988 SqFt Days Listed: 34
-1.90% ($10,000) 1 Price Change : Last Change 9 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Whether 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, no neighbor on one side. Has a front covered porch. Back patio deck. Back lot has no neighbor on either side. Home is move in ready and can close quickly. New appliances in the home. Ductless ac. Led lighting and tankless water heater. Storage shed. 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. $9168. for primary home of flood, wind and homeowners. Could be less with higher deductibles. Easy to show. No Homeowners association, Not leased land. Has been connected to central sewer. NO TRESPASSING! By appointment.

$539,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,020 SqFt Days Listed: 218
-22.89% ($160,000) 5 Price Changes : Last Change 2 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.

$539,900
Big Pine Key
Palm Villa   - MM: 30.50
2 Bed, 2 Baths, 816 SqFt Days Listed: 170
-5.94% ($34,100) 5 Price Changes : Last Change 5 Days Ago
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!

$565,000
Big Pine Key
Darios Subdivision   - MM: 31.00
3 Bed, 3 Baths, 972 SqFt Days Listed: 25
-3.42% ($20,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Located in a peaceful neighborhood on Big Pine Key, this well-maintained 3 bedroom, 2-bath home offers comfortable living both inside and out. Enjoy the new stainless appliances and a metal roof was installed in 2018. Accordion shutters make it a breeze to button up. Just think, youre a bike ride away from local parks and everyday conveniences. Public boat ramps are also available nearby.Outside, the fully fenced backyard offers plenty of room for kids, pets, or weekend barbecues. Its a great spot to unwind or enjoy the outdoors in privacy and just disconnect.Youll love the large covered rear porch thats ideal for outdoor dining, morning coffee, or winding down in the evenings.Whether youre a first-time buyer, a growing family, or just looking for a solid home in the Lower Keys, this property is a great option for year-round living. Theres also a separate entrance from the master bedroom to the rear deck.With great outdoor space and generous parking, this one is definitely worth a look.Come and enjoy the Keys lifestyle.

$575,000
Big Pine Key
Tropical Key Colony   - MM: 30.00
2 Bed, 2 Baths, 884 SqFt Days Listed: 18
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Cute Custom built home, 2 Bd/ 2bth with laundry closet. French doors to a spacious screen porch and wrap around balconies. Central AC w/ heat. Covered parking and concrete patio. Legal storage 12X13 downstairs w/ vents. Concrete slab under house. House is in AE8 and at floor upstairs sits at 12.53 House has been connected to central sewer w/pump system. No home on one side nor behind house adding some privacy. Vacant and easy to show. 45 min to Key West 20 min. to Marathon, 10 min to Bahia Honda State Park or less to a Public Boat Ramp at Spanish Channel. 2.5 hr. to Miami. Nice waterfront park across highway also there are a few more parks in Big Pine Key with tennis, racquetball, walking/exercise trail, basket ball, baseball. Grocery store, library, restaurants, post office, churches all on Big Pine, Bike paths you dont even have to get in the car. Owner will be doing a 1031 Exchange.

$575,000
Big Pine Key
Sands Subdivision   - MM: 31.00
3 Bed, 3 Baths, 960 SqFt Days Listed: 17
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Big Pine Key Heres your opportunity to get into a 3 Bedroom. 2 Bath stilt home in the Keys. Metal Roof. Central A/C & Heat. Sliding door from house to Covered Porch. Garage and Storage, downstairs, Concrete Patio. Back yard has concrete slab for a storage shed. Sewer has been connected and paid for in full. Fenced. Easement behind fence line between this home and back neighbor. For utility co. AE 8 Flood zone but house is at 12.1 Rented need notice to show. Renters are on a month to month. Nice community waterfront park nearby. 2 other Parks on Island. Bike paths on Big Pine. Grocery, Restaurants, Church, Library. Key West 45 min. Marathon 20 min. Miami 2.5 hours.

$579,900
Big Pine Key
Palm Villa   - MM: 30.50
3 Bed, 3 Baths, 1,508 SqFt Days Listed: 110
-2.86% ($17,100) 1 Price Change : Last Change 45 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Look no further.....this charming Big Pine Key Cottage has all the comforts you are looking for in a lush tropical setting. Through the front foyer, you are welcomed by an open concept living and kitchen area with natural lighting and a neutral painted interior that creates a relaxing atmosphere whether casually dining or entertaining guests. No details were spared making this 1,508 Sq Ft, 3 bedroom, 2 bathroom home feel cozy in a tropical setting. Immaculately maintained, low maintenance, and most furnishings included - just waiting for you to start living the Florida Keys Lifestyle you have always dreamed of. The unique floor plan creates an opportunity to use the first bedroom and ensuite bath for visiting family and friends with its own private entrance.The 6,250 Sq Ft lot features a paved concrete driveway and boasts palm trees, tropical foliage varieties, including a mature Keitt Mango tree, and Tamarind tree. Nestled in a quiet neighborhood, the back yard borders 149 acres of Key Deer Refuge. There is a detached 12 x 20 ft outbuilding with a 4 1/2 x 12 ft covered porch and two work benches. Plenty of extra space for storing your bicycles, or outdoor toys such as kayaks and paddle boards. New metal roof in 2022, stainless steel appliances including a new refrigerator, dishwasher and new On Demand hot water heater. Located only one mile from grocery shopping, restaurants, pharmacys and much more. Plenty of room to park a boat and trailer. Plenty of room for a POOL. Call today for your personal showing, you dont want to miss this one!

$594,999
Big Pine Key
Sands Subdivision   - MM: 31.00
3 Bed, 3 Baths, 960 SqFt Days Listed: 32
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Cute as a button and move-in ready! This three bedroom and two bathroom charmer has had many recent updates including fresh paint and a newer roof. Impact resistant doors and windows, as well as great elevation ensure reasonable insurance rates. Full concrete slab under the home for parking and storage and fully fenced in yard makes this a perfect home for a family to enjoy. Make an appointment to see this one today!

$599,999
Big Pine Key
Doctors Arm   - MM: 30.50
3 Bed, 3 Baths, 1,080 SqFt Days Listed: 62
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Other Dockage

Updated adorable 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 home has been tastefully updated, featuring stainless steel appliances, newer 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.

$625,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 912 SqFt Days Listed: 48
-3.85% ($25,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

This home offers privacy with an over-sized grass yard, surrounded by nature with a natural garden and room for all your needs. This double lot property is 10,000SF with room for a pool, tiki and/or an accessory structure. French doors take you to an additional 500+SF screened patio that extends your living space and provides tranquil views over the garden and lush yard. Spend your mornings having coffee and your evenings enjoying cocktails with friends and family. Upon entering the home, the open living room/kitchen has beautiful hardwood floors that transition to over-sized tiles in the bedrooms. Both bathrooms have been updated and finished with stone tile in subtle shades of gray. The kitchen is ready for your own updates and has views out to an open balcony. The house has great airflow on cool nights and the sound of nature can be heard rustling through the garden. Key deer graze and rest in the shades of the tropical landscaping and romp in the crisp mornings. The spacious master bedroom can accommodate a king size bed as you star gaze at night. There is a downstairs storage room for all your outdoor needs and plenty of room for extended outdoor living. The community boat ramp is one block from the home and the yard provides ample parking for your trailer. Dont miss this gem and your opportunity for Keys Cottage living.

$655,000
Big Pine Key
Sands Subdivision   - MM: 31.00
3 Bed, 3 Baths, 1,144 SqFt Days Listed: 10
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome to your slice of paradise in Big Pine Key! This beautifully updated 3-bedroom, 2-bath home offers the perfect blend of modern comfort and laid-back Keys living. Partially furnished and move-in ready, this island retreat boasts impact windows and doors throughout for safety and peace of mind.Step inside to a bright and open living space with sleek finishes, coastal-inspired details, and a thoughtfully designed layout perfect for both relaxing and entertaining. The home opens to a spacious porch -- ideal for sipping your morning coffee. Outdoors, youll find an inviting tiki hut perfect for gatherings, an outdoor shower for rinsing off after a day on the water.Dont miss this opportunity to own a modern, Keys-style home in a tranquil, established neighborhood -- where island life meets contemporary convenience.Schedule your private showing today and start living the dream in Big Pine Key!

$665,000
Big Pine Key
Sands Subdivision   - MM: 31.00
3 Bed, 3 Baths, 1,272 SqFt Days Listed: 185
-4.32% ($30,000) 3 Price Changes : Last Change 36 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Dont miss out on this amazing property. 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
Big Pine Key
Sands Subdivision   - MM: 31.00
3 Bed, 3 Baths, 1,272 SqFt Days Listed: 17
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

NATURES EMBRACE, SERENITYS TOUCH! Charming 3-Bedroom, 2-Bath Gem with Tropical Landscaping and Modern Upgrades!This beautifully well-maintained 3/2 home is a true gem nestled in a lush, tropical setting. Enjoy your own slice of paradise with mature mango, and banana trees, and pineapple plant, all within a fully fenced yard for privacy and security.Recent upgrades include a remodeled main bath, fresh interior paint, a durable metal roof, and updated A/C units (2020 & 2024) for year-round comfort. The kitchen features modern appliances, while elegant Hunter Douglas window treatments add a touch of class throughout.Ample storage space is available under the home, and the screened private patio downstairs is perfect for relaxing or entertaining. Whether youre enjoying the vibrant garden or the stylish indoor comforts, this home is move-in ready and waiting for you!

$689,000
Big Pine Key
Tropical Key Colony   - MM: 30.00
3 Bed, 3 Baths, 1,184 SqFt Days Listed: 80
-4.97% ($36,000) 3 Price Changes : Last Change 11 Days Ago
Single Family - Contingent - 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!

$697,000
Big Pine Key
Big Pine Key Inc   - MM: 31.00
2 Bed, 2 Baths, 1,447 SqFt Days Listed: 82
-10.64% ($83,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

CHARMING HOME NESTLED IN THE TREES ... if you love nature and a bit of privacy, this 14,000 sq. ft. property is not to missed. The conveniences and amenities that Big Pine Key offers are easily accessible by foot, bicycle and car. Look in any direction and all you see are trees! Custom-built, the home has wonderful porch spaces on two levels ... its light and bright inside with abundant windows and French doors, and a soaring cathedral ceiling in the living room and primary suite / loft walkways in the upper level. The kitchen features custom mahogany and African mahogany counters, as well as a stunning wood ceiling. On the main level youll find one bedroom and bath, and the upper level has the primary bedroom with ensuite bath and loft areas for an extra guest, office and quiet reading. New roof in 2018; recent central AC. There are trees in every direction that one looks; the east and west facing porches on both levels are prime for bird watching. If you enjoy walking or biking, its a 10-minute walk to the post office, and a short walk or bike ride to Winn Dixie Plaza, drug stores, banks, and the Pine Channel Nature Park. On the ground level youll find covered parking, 500 sq. ft. of storage, and a great storage shed tucked away in the back of the property. Cleared to the south, the double lot measures 100 x 140. Come see why the current owner has loved this home and property for over 30 years!

$699,000
Big Pine Key
Sea View   - MM: 28.00
2 Bed, 2 Baths, 864 SqFt Days Listed: 102
-19.10% ($165,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Ultimate Privacy in Big Pine KeyStep into an extraordinary sanctuary of seclusion, where tropical elegance meets unmatched exclusivity. 1 of only 2 homes in the entire Seaview subdivision of Big Pine Key.3231 Pompano Drive is a beautifully renovated island retreat set on a 10,000 sq. ft. lot, surrounded by untouched nature and abundant wildlife. No additional homes can ever be built, ensuring that this private paradise remains forever preserved.Inside, the open-concept living space is designed to impress, flowing seamlessly into a stunning kitchen featuring shiplap tile accents, new cabinetry, quartz countertops, stainless steel appliances, and a propane stove. Vaulted wood-beamed ceilings, mini-split A/C units, AT&T Fiber, tankless hot water and brand-new vinyl plank flooring add to the homes tropical charm. Sunlight pours in through expansive windows, showcasing breathtaking views of the pristine nature preserve.Designed for indoor-outdoor living, this home offers a screened upper porch, ideal for peaceful mornings surrounded by nature. The spacious screened enclosure downstairs provides a private retreat, while the swim spa is perfect for unwinding under the stars.With ample parking for an RV with hookkups, boat, trailers, and more, this home is an outdoor lovers dream. A nearby boat ramp ensures quick access to world-class fishing, kayaking, and boating.Come see this secluded oasis-paradise awaits.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 06-01-2025.
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