Big Pine Real Estate Search

Newest Big Pine Homes and Condos for Sale

$899,000
3 Beds ⋅ 2 Baths ⋅ 620865 MLS
Experience the beauty of the Lower Florida Keys from this waterfront 3-bedroom, 2-bath home offering breathtaking open water views in Big Pine Key. Enjoy spectacular sunrises, refreshing island breezes, and the peaceful setting that makes waterfront living so special. Wraparound decking and elevated walkways invite you to take in the panoramic views while providing easy access to the home's outdoor living spaces. A rare and valuable feature, the property includes ownership of a portion of the bay bottom, enhancing its unique waterfront appeal. An additional adjacent 50' x 80' lot is also included, providing added privacy, expanded outdoor space. Whether you're relaxing on the porch, entertaining guests, or simply taking in the panoramic water views, this home is the perfect island retreat. Ideally located near world-class boating, fishing, diving, and the natural beauty of the Florida Keys, this property offers an exceptional opportunity to enjoy the waterfront lifestyle. Don't miss your chance to own this unique Big Pine Key property with open water views, bay bottom ownership, and an additional adjoining lot.

31247 Ave J, Big Pine
$749,900
3 Beds ⋅ 2 Baths ⋅ 620858 MLS
A Boating/Fishing Dream Home.... This Canal Front Stilt home sits on an oversized corner lot, in ''Key Deer Refuge'', beautiful wild-life and Key Deer abound, 2/bedroom, 2/bath, a 3rd bonus room, you may use as a bedroom or office, a spacious Living/Dining/Kitchen with lots of light, stainless appliances, impact windows, Bamboo/tile floors. Enjoy the Florida Keys Lifestyle on your Boat docked at your back door, at 'L' shape total 63' concrete dock with electric and water at dock with pavers adjoining the dock awaits a sitting area/picnic table, Tiki Hut or pool, paver driveway, minutes to the Gulf and the Famous ''Content Keys''. Entire property is fenced for privacy, an irrigation system, mature palms, fruit trees and beautiful vegetation, an extra side yard with (50 Amp electricity), sewer and water for parking an RV or storage of your boat trailer, a camera system will convey, plenty storage/work-space downstairs with a generator (to be connected), exterior freshly painted, $200K renovated in the last few years. Room for a pool or Tiki Hut, Boat ramp is on Bittersweet about 50' from property. May Vacation Rent, Annual Rent or use as a primary home or fish camp, owner's closet downstairs for your convenience. Own your Piece of Paradise!!!Pro Pics coming!

1821 Bittersweet Ave, Big Pine
$1,199,000
3 Beds ⋅ 2 Baths ⋅ 620836 MLS
Experience the keys waterfront lifestyle! This charming 3 bedroom, 2 bath home has peekaboo views of Big Pine Bight and is minutes away from Bogie Channel with NO limiting bridges to slow you down. Only 2 minutes to the Atlantic, and direct access to the Gulf. Equipped with a 10,000 LB boat lift, the boat is also available as a separate purchase. The buyer will get first right of refusal on the boat. There is a separate nicely sized storage room that could also be a workshop. The garage is currently set up as bonus space, it would make a great 'man cave', or play room! This Key West style home is being offered fully furnished as well as an extensive list of required amenities, such as a fully stocked kitchen, bedding and bath towels, to name a few. Bring your toothbrush and fishing rods, drop a line off of the seawall and catch your dinner, or walk to the famous No Name Pub for pizza and adult beverages. Or, enjoy a quiet evening under the stars, in your private heated pool, grilling your catch of the day. The outdoor patio is expansive, private and fenced in, with a puppy area for ease of relaxing for everyone! Newer roof, A/C, and hot water heater.

1657 Watson Blvd, Big Pine
$449,000
2 Beds ⋅ 1 Baths ⋅ 620831 MLS
Start your next adventure from this 2-bedroom, 1-bath retreat in Big Pine Key's Eden Pines community. Just a short stroll from the neighborhood boat ramp, you can be on the water in minutes for fishing, reef trips or an afternoon at the sandbar. Back at home, a fully enclosed yard provides generous outdoor space for pets, entertaining or relaxing in the island breeze. The property sits along a dead-end street with very little passing traffic, while visits from the area's famous Key deer add to the true Big Pine Key experience. The kitchen offers warm butcher-block counters, a farmhouse-style sink and a smooth glass-top range. An indoor laundry room provides added convenience. Climate control is handled by a newly installed mini-split in the living area, plus individual units in both bedrooms for efficient, room-by-room comfort. A metal roof and raised water heater complete the home's practical features. This is an excellent opportunity to enjoy a relaxed Florida Keys lifestyle with convenient boating access right nearby.

29146 Hibiscus Ln, Big Pine
$849,000
3 Beds ⋅ 2 Baths ⋅ 620830 MLS
Situated on an oversized corner lot at the end of a quiet street, this brand-new home is ready to welcome its first owner. Thoughtfully built with durability, quality, and modern design in mind, 281 Pelican Lane offers the perfect blend of contemporary comfort and the relaxed lifestyle of the Florida Keys. Featuring 3 bedrooms and 2 bathrooms, the home is well suited as a full-time residence, seasonal retreat, or monthly vacation rental. The expansive lot provides plenty of room to create your own private outdoor oasis, with space for a pool, tropical landscaping, and entertainment areas. The property overlooks a plugged canal, offering peaceful water views without boat traffic. Enjoy launching a kayak or paddleboard to explore the neighborhood waterways and surrounding mangrove trails, where you can experience the natural beauty and wildlife that make the Florida Keys so special! Call for your private showing today!

281 Pelican Ln, Big Pine
$700,000
3 Beds ⋅ 2 Baths ⋅ 620819 MLS
Welcome to Eden Pines--now offered at an exceptional new price of $700,000! This charming 3-bedroom, 2-bath home sits on a spacious and private 10,000 sq. ft. lot in the heart of Big Pine Key. With a garage, abundant storage, a fully fenced yard, and room to add a pool, this property offers endless potential. Inside, you'll find an inviting open-concept floor plan, two beautifully updated bathrooms, and comfortable living spaces designed for easy Florida Keys living. The covered back porch is the perfect place to relax with your morning coffee while enjoying the peaceful surroundings and frequent visits from the neighborhood Key deer. Located just minutes from the community boat ramp, this home is ideal for boating enthusiasts and anyone looking to embrace the laid-back island lifestyle. Comfortable, private, and now aggressively priced at $700,000, this is an incredible opportunity to own a piece of the Lower Keys. Assumable flood insurance is only 926.00!! Wind 6,121.00!

29160 Primrose Ln, Big Pine
$599,000
2 Beds ⋅ 2 Baths ⋅ 620818 MLS
Private Lower Keys opportunity! Nestled behind a lush hedge of mature Areca palms, this 2BR/2BA CBS home offers privacy, solid construction, and endless potential. Recent improvements include a 2018 post-Irma roof and storm shutters. The fully fenced 6,250 sq. ft. lot provides ample space for a pool, outdoor living, or tropical gardens, with a storage shed already in place. Enjoy a peaceful neighborhood within walking distance of No Name Key and just minutes from the Blue Hole, parks, shopping, dining, and local amenities. Ready for your personal updates and vision, this property is an excellent opportunity to create your own island retreat.

30354 Palm Dr, Big Pine
$820,000
2 Beds ⋅ 2 Baths ⋅ 620816 MLS
Nestled in the heart of Big Pine Key, this 2-bedroom, 2-bath canal-front ranch style home offers a rare opportunity to enjoy the Florida Keys lifestyle while investing for exceptional future potential. Situated on an oversized 1 1/2 lot with direct boating access out to open water in 3 mins, this property is a true waterfront gem. The existing home provides comfortable island living with abundant natural light and serene canal views. Features include a large, covered boatlift!!!!! & basin, garage, no bridges and outside storage. Step outside to enjoy your private waterfront setting under the Poinciana tree, perfect boating, fishing kayaking, or simply relaxing while taking in the tropical surroundings. What truly sets this property apart is the expansive double lot, an increasingly rare ROGO exempt offering in the Keys. Whether you're looking to renovate, expand, or build a stunning new luxury waterfront home in an upscale community, the possibilities are endless. The generous lot and coveted, covered boat basin provide ample space to create your dream residence while maximizing the property's waterfront location and investment potential. Conveniently located 5 minutes to open water, near parks, nature preserves, dining/shopping, and world-class fishing and diving this property offers the perfect blend of tranquility and accessibility. Whether you're searching for a full-time residence, vacation retreat, or premier redevelopment opportunity, this exceptional canal-front property is ready to make your vision a reality.

1817 Watson Blvd, Big Pine
$1,400,000
3 Beds ⋅ 2 Baths ⋅ 620815 MLS
Discover your paradise in the heart of Big Pine Key! This beautifully maintained 3-bedroom 2-bath CBS, stilted home offers the perfect blend of Lower Keys Island charm and all the modern comforts. Step inside to find a bright, wide-open living space designed for relaxed Keys living and entertaining, with plenty of room for family & friends. Outside, your private backyard oasis awaits. Take a refreshing dip in the sparkling pool/hot tub, lounge in the tropical sun, or entertain your guests in the expansive outdoor living areas amidst the lush tropical landscaping. Whether you're enjoying morning coffee watching the sunrise over the Bay or unwinding with a cocktail after a day on the water, this home is designed for year-round enjoyment. Located in the tranquil Tropical Bay Estates community, you'll be literally minutes from world-class fishing, boating diving, nature trails within the natural beauty of the fabulous Lower Keys. Whether you're searching for a full-time residence, a vacation retreat or a profitable vacation investment rental, this exceptional property offers the laid-back island lifestyle you've been dreaming of. Come experience the best of the Florida Keys-where every day feels like a vacation.

1518 Sunrise Dr, Big Pine
$1,499,000
4 Beds ⋅ 3 Baths ⋅ 620791 MLS
Brand New Home! Oversized Custom 4 bedroom 3 bath home located on a beautiful protected deep water canal with excellent access to the Gulf and Atlantic. This 2000 sq ft home is situated in a quiet neighborhood and features an open living area design with chef's kitchen/ quartz counter tops, high ceilings, covered porch, custom railings, impact windows and doors, custom concrete heated and chilled pool. The home comes complete with a custom 60 ft boat dock for all your water toys. The custom concrete pool, pool decking and landscaping will be completed within the month and this brand new home also comes with a 1 Year Builders Warranty. The home is perfectly situated for the water enthusiast with world class fishing, diving, snorkeling, paddle boarding and kayaking! Don't wait on this one!!!

2211 San Sebastian Dr, Big Pine
$599,000
3 Beds ⋅ 2 Baths ⋅ 620767 MLS
Welcome to laid-back island living in this beautifully updated 3-bedroom, 2-bathroom home on Big Pine Key. Recent upgrades include a brand-new kitchen with stainless steel appliances, along with impact-resistant windows and doors throughout. The home also features a large downstairs enclosure offering abundant space for storage, tools, bicycles, kayaks, and other island essentials. Outside, the lush tropical setting and low-maintenance gravel yard create an inviting outdoor environment without the burden of extensive upkeep. Tucked away in a quiet community, the property is conveniently located near Big Pine Key Community Park, grocery stores, local restaurants, shopping, and everyday conveniences. An assumable VA loan with a sub 3% interest rate may be available to qualified buyers, subject to lender and VA approval. Assumable Flood Insurance 1010 per year, current windstorm 3500!

31118 Ave I, Big Pine
$1,450,000
3 Beds ⋅ 2 Baths ⋅ 620761 MLS
If you're looking for a property that can wear many hats, this one deserves a closer look! The Big Pine Key Bungalow sits on a spacious waterfront lot where open-water views and glowing sunrise skies set the tone for every day. Whether you're searching for a full-time residence, a vacation retreat, or a turn-key investment with a well-established vacation rental history, this home offers exceptional flexibility. Full of personality and intentional functionality, this turnkey, fully furnished 3-bedroom, 2-bath home was built in 2019 with hurricane-rated steel construction and upgraded smart home features throughout. The east-facing location captures breathtaking sunrises while offering direct boating access to both the Gulf and Atlantic. Inside, you'll find a bright, modern, and spacious home designed to take full advantage of its incredible surroundings. Large impact-rated windows and doors frame sweeping water views from nearly every room, filling the open-concept living, dining, and kitchen areas with natural light. One of the home's standout features is its versatility. Murphy beds allow guest rooms to effortlessly transform into home offices, hobby spaces, or fitness rooms, making it easy to adapt the home to your lifestyle. Thoughtful storage throughout adds even more everyday functionality. Outside, the adventure continues! Set on a large, fenced double lot with ~100ft of canal frontage, the property offers direct boating access to both the Gulf and Atlantic, putting some of the Keys' best fishing, diving, and exploring right at your fingertips. The property also features low-maintenance artificial turf, a heated saltwater pool, plenty of room for boat storage/RV parking, an outdoor shower, many tropical plants and fruit trees, fishing cleaning station, and all the gear that comes with the Florida Keys lifestyle. Whether your perfect day is spent on the water or simply relaxing poolside, you'll feel right at home here!

31536 Ave F, Big Pine
$699,000
2 Beds ⋅ 1 Baths ⋅ 620744 MLS
This updated concrete cottage with all the necessities you will need to enjoy waterfront living in the Keys. This home has a metal roof, mini split A/c, updated kitchen and bath and is situated on 3 lots giving you plenty of space. It is only a very short boat ride to Boggie Channel, the only market channel to both the Atlantic and Gulf in the Lower Keys. This is a great opportunity for boaters and naturalist as this is only a short walk or kayak to No Name Key, surrounding waters and nature trails. Large 280 square foot utility building with workshop. A short walk to the No Name Pub, a Keys historic watering hole. Don't miss your opportunity for this15000 square foot, 3 lot parcel with a lovely concrete home. Proof of funds or pre-qualification necessary to schedule a showing.

30881 Witters Ln, Big Pine
$899,000
4 Beds ⋅ 2 Baths ⋅ 620607 MLS
Waterfront Duplex with Income Potential in Big Pine Key! Live the Florida Keys lifestyle while your investment works for you. Welcome to 31032 & 31034 Hollerich Drive, a beautifully maintained waterfront duplex offering the perfect combination of island living and exceptional income potential. Located on a peaceful canal just steps from the Big Pine Community Park, this unique property features two spacious 2-bedroom, 1-bath residences, each with its own private entrance, private outdoor shower, and thoughtfully updated interior. Both units showcase bright, open floor plans with updated kitchens featuring stainless steel appliances, and ample cabinetry, along with renovated bathrooms, comfortable living areas, and spacious bedrooms. Whether you're searching for a primary residence, vacation home, or investment property, this duplex offers endless possibilities. Step outside and enjoy the laid-back Keys lifestyle with tropical landscaping, expansive gravel parking with room for boats and trailers, a detached storage building, and a relaxing canal-front setting perfect for enjoying the ocean breeze. Spend your mornings with a cup of coffee by the water, launch your next boating adventure, or simply unwind in your own tropical oasis. This versatile property is ideal for: -Living in one unit while renting the other -Generating income by leasing both units -Creating a family compound or multigenerational retreat -Seasonal or long-term rental opportunities Conveniently located near the Big Pine Community Park, shopping, dining, world-class boating, fishing, and all the natural beauty the Lower Florida Keys have to offer, this property truly has it all. Whether you're looking to invest, retire, or embrace the island lifestyle full-time, this rare waterfront duplex offers flexibility, charm, and endless possibilities. Own your piece of paradise while letting your investment help pay for it!

31032 Hollerich Dr, Big Pine
$579,000
3 Beds ⋅ 2 Baths ⋅ 620548 MLS
If you've been searching for an affordable stilted home in the Lower Keys that doesn't feel dated or compromised, this is one of the best values on the market. Built in 2000 and set on a beautifully fenced 5,000 sq. ft. corner lot with large mature trees, this 3 bedroom, 2 bath home offers the elevated Florida Keys lifestyle at a price point that's hard to find. Inside, the home features a great floor plan with the spacious primary suite tucked away on its own side of the house for added privacy, while two guest bedrooms and a full bath are located on the opposite wing. The updated kitchen, in home washer and dryer, and bright, comfortable living spaces make this home feel move in ready. Step outside to enjoy the inviting open front porch, perfect for relaxing and enjoying the Keys breeze. Additional highlights include a post Irma metal roof, downstairs enclosed storage, and plenty of parking for vehicles, trailers, or toys. The location is just as appealing, walking distance to Big Pine Community Park, and only minutes from Winn Dixie, shopping, dining, and other local conveniences. For buyers looking for a well kept, affordably priced stilted home with modern updates, functional space, and a convenient Big Pine Key location, this property stands out as an exceptional opportunity.

31054 Ave J, Big Pine
Start Your Search

Big Pine Homes for Sale

Located in the Lower Keys of the one-hundred-mile-long chain of islands known as the Florida Keys, Big Pine Key is a great place to buy a home far away from the typical overcrowded urban American lifestyle. This gorgeous resort-style community is in unincorporated Monroe County and has much to offer prospective homebuyers and vacationers alike. Surrounded by stunning natural beauty, Big Pine Key encompasses many delightful little restaurants and small beach resorts, and has a quiet, laid-back vibe.

More than four thousand, two hundred people live in Big Pine Key and enjoy its many services, amenities, and attractions. It is the second-largest of the Key islands and has excellent options for recreation, dining, and shopping, and its schools are operated by the Monroe County School District. Adding to its allure, it is only two to three hours from Miami International Airport and Ft. Lauderdale-Hollywood International Airport, while Key West International Airport is just a short drive away. Big Pine Key real estate also offers easy access to an intra-coastal nautical highway, train services, and interstate bus routes. Big Pine also boasts points of interest that include the Blue Hole, No Name Key, National Key Deer Refuge, and Looe Key coral reef.

Real estate in Big Pine Key is diverse and includes everything from lakefront properties and beach homes to apartments and single-family detached residences. Most homes for sale in Big Pine Key have Gulf or canal views, and many are stilt or conch homes. There are some gorgeous Big Pine Key luxury estates in neighborhoods like Pine Channel Estates, but there are also more modest and affordably priced Big Pine Key properties in neighborhoods like Sands Sub, Darios Sub, Doctor’s Arm, Pine Heights, and Eden Pines Colony. In addition to detached housing, some of these Big Pine Key neighborhoods also include apartments, duplexes, and Big Pine condos. We would love to help you by providing details about the specific properties available in Big Pine Key, Florida, so please connect with us today or at your earliest opportunity.

Our website features the best Big Pine real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in the Big Pine real estate market? Sign up for a Big Pine Real Estate Market Report to see what’s active, under contract, and sold!