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$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
$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
$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
$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
$999,999
3 Beds ⋅ 2 Baths ⋅ 620545 MLS
Where open water sunrise views and world-class boating meet, you'll find this elevated waterfront retreat at 31485 Avenue G in Big Pine Key. Offering 3 bedrooms, 2 bathrooms, and 1,196 square feet, this waterfront home features 70 feet of concrete dockage on a clean, approximately 20-foot-wide, 3-foot-deep canal with quick access to the Atlantic Ocean, Gulf of Mexico, Bahia Honda Channel, nearby sandbars, the backcountry, and the Content Keys. Whether your plans include chasing tarpon, pulling stone crab traps, snorkeling, diving, or cruising by boat to waterfront restaurants, this location puts it all within easy reach. Built in 2020, the home features abundant natural light, a metal roof, hurricane shutters, a new A/C installed in 2025, boat davits, a custom concrete fish cleaning station, nautical-style Key Deer fencing, and three storage sheds that convey with the property. The thoughtfully designed interior is move-in ready while offering the opportunity to update the kitchen and bathrooms with your own style. Mature tropical landscaping, including date palms and a rare yellow coconut palm, creates a private island setting. The open lower level may qualify for future enclosure under current Monroe County regulations, subject to buyer verification. A canal bubbler system helps maintain water quality, with an annual maintenance fee currently at $150. Near Grimal Grove and Big Pine Community Park, this property offers the boating, fishing, and waterfront lifestyle that make the Lower Keys so unforgettable.

31485 Ave G, Big Pine
$1,650,000
3 Beds ⋅ 2 Baths ⋅ 620510 MLS
LOOKING FOR A KEYS HOME WITH SOLID CONSTRUCTION? Check out this updated 3BD/2BA CBS home in desirable Pine Channel Estates, Big Pine Key -- just 30 miles from Key West and offering low-maintenance living at its finest. Step through the door into an open floor plan filled with natural light. Impact-resistant sliding glass doors blend indoor and outdoor living, while 32''x32'' porcelain tile runs throughout. The kitchen is a showstopper -- quartz counters, stainless steel appliances, two pantries, and plenty of cabinet space. The primary suite is a true retreat with an ensuite bath, two walk-in closets, and a sitting area with room for a couch or desk. Enjoy the screened porch off the living room and master suite for extended outdoor living, then head downstairs to nearly 1,000 sq. ft. of garage and storage space, a covered carport, garden shed, screened sitting area, - all leading out to your private boat lift and davits. The 46 ft. wide canal offers easy access to both the Atlantic and back country, with 75 ft. of concrete seawall and davit ready to go. Poured concrete floors and impact-resistant windows and doors throughout make this home feel like a fortress. Outside, low-maintenance living continues with artificial turf that stays green without a lawnmower in sight, plus a tiki hut, 4-hole putting green, and a newly added paver driveway. With canal frontage and salt pond views, this is your private oasis in the heart of the Florida Keys -- your favorite fishing and dive spots are just minutes away by boat. Come live the Keys life!

29667 Forrestal Ave, Big Pine
$799,000
3 Beds ⋅ 1 Baths ⋅ 620504 MLS
This newly remodeled 3-bedroom, 1-bathroom home is perfectly positioned on a spacious lot in the heart of Big Pine Key, offering 10,275 sq ft of land and an incredible 75 feet of waterfrontage, with a concrete seawall. With quick access to the ocean via Spanish Harbor Channel, this is a boater's dream come true. Inside, enjoy peace of mind with impact-rated windows and doors, a sturdy metal roof, and stylish modern finishes throughout. Outside, there's plenty of room to expand, entertain, or simply relax and soak in the serene Keys lifestyle. Located just minutes from shopping, dining, and Big Pine Community Park, this home combines privacy and convenience in one of the Lower Keys' most desirable neighborhoods.

550 Pine Ln, Big Pine
$695,000
2 Beds ⋅ 2 Baths ⋅ 620469 MLS
Remodeled waterfront home! Located in a lovely neighborhood with a boat ramp right around the corner! Exterior of property has open parking as well as covered parking for multiple vehicles. Below home is surrounded by lattice to give additional shade and privacy. So much potential downstairs for outdoor entertainment.The main living area has gone through a full renovation. Kitchen boast sleek quartz countertops and newly installed cabinets and backsplash. Both bathrooms have been upgraded. Gorgeous high end tiling in shower and floor, accompanied by new vanities. Throughout the house is luxury plank vinyl flooring and crown molding to make this home shine even more. Off main living area is an expansive back deck for relaxation. Local grocery store, dog park, and food/beverage only minutes away! Like what you see? Call today!

29172 Rose Dr, Big Pine
$1,695,000
3 Beds ⋅ 2 Baths ⋅ 620361 MLS
Waterfront coastal retreat in a quiet neighborhood, just 3 houses from open water! This beautifully renovated 3-bedroom, 2-bath stilt home offers coastal comfort with modern updates and relaxed waterfront living. Enjoy breathtaking sunsets from the screened-in balcony, or head down to the 70 ft dock with a 12,000 lb boat lift, perfect for boating enthusiasts. The fenced-in yard features lush fruit trees and outdoor space to unwind, plus room for an RV with 30 amp service. A spacious downstairs provides plenty of storage, making this home as functional as it is inviting. A rare opportunity to own a move-in-ready waterfront home in a peaceful setting!

29162 Bougainvillea Ln, Big Pine
$1,099,000
3 Beds ⋅ 3 Baths ⋅ 620351 MLS
Welcome to this beautifully updated 3-bedroom, 2.5-bath waterfront home situated on a rare 12,000 sq. ft. double lot in the heart of Big Pine Key. Thoughtfully renovated throughout, this spacious two-story home offers bright, comfortable living with plenty of room for family and guests. Inside, you'll find a large living room filled with natural light, a versatile office/den, and an updated kitchen and dining area designed for everyday living and entertaining. Boaters will appreciate the canal access to Pine Channel, providing quick access to both the Atlantic Ocean and Gulf waters. The screened porch overlooking the canal offers a comfortable spot to relax, dine outdoors, or enjoy the peaceful waterfront setting. Outside, the expansive double lot provides plenty of room for parking, pets, and outdoor activities. The open space beneath the home offers endless possibilities for storage, a workshop, recreational space, or an outdoor living area. There's also ample room to add a pool and create your own private backyard retreat. Located in a desirable, family-friendly neighborhood, this move-in-ready property combines generous indoor and outdoor space, waterfront access, and the relaxed lifestyle that makes the Florida Keys so special.

1615 Fern Ave, Big Pine
$1,695,000
3 Beds ⋅ 2 Baths ⋅ 620330 MLS
Welcome to your private Lower Keys oasis, where solid concrete construction meets refined coastal style. This beautifully designed 3-bedroom, 2-bath waterfront home is offered fully furnished and truly move-in ready, featuring impact windows and doors, a sleek 24 gauge standing seam metal roof, and bright, open living spaces made for effortless island living. Outdoors, the home transforms into a resort-style retreat. Enjoy a heated saltwater pool, expansive decking, and a wonderful poolside tiki hut perfect for entertaining or unwinding in the shade. Mature palms and lush tropical landscaping create a peaceful, secluded atmosphere. The fully fenced yard is secure for pets and even has a large parking spot perfect for a boat on trailer or an rv. Boating enthusiasts will appreciate the private concrete dock, and easy access to the pristine waters of the Lower Keys. Some of the absolute best kayaking and paddleboarding spots are just minutes away. With generous 1900 sq ft garage and storage space there is room for all your island toys! This turnkey waterfront escape delivers the perfect blend of comfort, beauty, and adventure. Learn more about Tropical Bay Community: www.TropicalBayEstates.org Owner has obtained ACOE and DEP permits to expand the dockage across the second lot if a buyer wants to add more than the existing 75'.

30463 Hawk Ln, Big Pine
$1,550,000
3 Beds ⋅ 2 Baths ⋅ 620317 MLS
If you've been dreaming of easy waterfront living in the Keys, this beautifully furnished CBS home in friendly Pine Channel Estates is ready to welcome you. Built in 1989 with solid construction, it offers 1,392 sq. ft. of living space, poured concrete floors on pre-stressed beams, and an impressive 754 sq. ft. garage/storage area. Inside, cathedral ceilings and high transom windows bring in plenty of natural light and give the home an open, comfortable feel. Outside, enjoy 75 ft. of canal frontage with a step-down dock, two boat lifts, one of which is rated for 14,000 lbs., and very quick boat access to Pine Channel, the ocean, and the backcountry. The split-bedroom floor plan offers 3 bedrooms and 2 baths; overlooking the canal, the south-facing screened porch provides additional outdoor living. Accordion shutters and a metal roof add peace of mind. Permitted in 2007, the elevator is no longer functional and is being sold as-is. This is a solid, comfortable Keys home where boating, sunshine, and life in paradise are right outside your door.

29424 Forrestal Ave, Big Pine
$1,199,000
4 Beds ⋅ 3 Baths ⋅ 620193 MLS
Discover a rare combination of privacy, waterfront living, and spacious outdoor enjoyment on this nearly half-acre canal-front property in Big Pine Key. Boasting approximately 130 feet of waterfront, this unique location at the end of the canal offers minimal boat traffic, easy boating access to both the Atlantic Ocean and Gulf waters. Set behind lush tropical landscaping and a gated entrance, the fenced 19,762-square-foot lot creates a private retreat surrounded by mature palms, fruit trees, orchids, and vibrant native plantings. The heated swimming pool serves as the centerpiece of the outdoor living area, complemented by a large screened patio perfect for relaxing, entertaining, or enjoying the peaceful garden setting. Designed with boaters and outdoor enthusiasts in mind, the property offers ample room for multiple vessels, RV parking, and trailer storage, with convenient access through a separate gate. The ground-level residence spans approximately 2,166 square feet and features four bedrooms, two and one-half updated bathrooms, an upgraded kitchen, laundry room, impact-resistant windows and doors, a newer mini-split air conditioning system, and a ceramic tile roof installed in 2017. Additional highlights include abundant storage space, a dedicated workshop area, and extra refrigeration and freezer capacity for fishing gear and supplies. Offered furnished, this home is ready to be enjoyed from day one. Located just a short distance from Big Pine Community Park, residents can enjoy pickleball, tennis, basketball, walking paths, playgrounds, waterfront picnic areas, and community events. Whether you're seeking a full-time residence, vacation home, or private waterfront escape, this property offers the space, seclusion, and Keys lifestyle that are becoming increasingly difficult to find.

30985 Hibiscus Dr, Big Pine
$400,000
620170 MLS
Commercial waterfront lot at 29517 Big Pine St, Big Pine Key. Deep-water canal with quick access to both the Gulf of Mexico and the Atlantic Ocean, icommercial fishing, marine operations, boating, or waterfront business use. Located on a quiet cul-de-sac with exceptional privacy--no neighbors in front or on either side. Nearly surrounded by county-owned land that is not expected to be developed. Enjoy a peaceful natural setting with frequent Key Deer sightings. Sale includes an existing 8' x 52' trailer. Rare opportunity to own a private commercial waterfront property in the Florida Keys with deep-water access and outstanding boating convenience.

29517 Big Pine St, Big Pine
$750,000
2 Beds ⋅ 2 Baths ⋅ 620072 MLS
Experience the laid-back Florida Keys lifestyle in this beautifully maintained, double lot sized at 12,000 sq ft, concrete 2-bedroom, 2-bath stilt home located on a desirable clean swim canal in Big Pine Key. Situated at the end of the street with no through traffic, this secluded waterfront retreat offers exceptional privacy, tropical breezes, and the perfect blend of comfort and coastal living. The home sits on an ideal east-west exposure, allowing for a refreshing cross breeze throughout the property and abundant natural light from the many windows throughout the home. Step inside to discover a nicely finished interior featuring laminate flooring, granite countertops, and soft close cabinets, a spacious living and dining room area, and huge walk-in closets that provide excellent storage space. Offered fully furnished, this home is move-in ready and ideal as a full-time residence, vacation getaway, or investment opportunity. Outdoor living is truly exceptional with two large screened decks that enhance the outdoor living space, perfect for relaxing, entertaining, or enjoying peaceful canal views and tropical surroundings. Enjoy looking at the many fruit trees on the property including, papaya, mangos, dragonfruit, 2 varieties of bananas, grapefruit, lemon, Spanish limes, melon, and pineapples. The property also offers plenty of room for a pool, gazebo, or garden area, creating additional potential for your private island oasis. The fenced yard adds both privacy and security, while the clean closed canal behind the home is known for its clear water and fish, making it ideal for kayaking, paddleboarding, or simply enjoying nature. A concrete seawall with kayak launch provides direct canal access right from your backyard. Additional features include: Impact windows and doors Stair access on both sides of the house Conforming enclosed space under the home with ample room for storage, hobbies, or recreational use Ground-level garage and storage area

251 Pelican Ln, Big Pine
$785,000
2 Beds ⋅ 1 Baths ⋅ 620040 MLS
Experience the laid-back Florida Keys lifestyle in this beautifully updated, turn-key canal-front retreat, nestled in the quiet Eden Pines neighborhood among the roaming Key Deer. Situated on a 50-foot concrete seawall with step-down access, fish cleaning station, and a new boat lift, this property offers excellent boating access to both the ocean and bay. Inside, the open concept living area is filled with natural light and designed for comfortable island living, boasting high exposed-beam ceilings, adding character and depth to the space. The spacious kitchen features solid wood cabinetry, while recent updates to the bathroom, bedrooms, and bedroom flooring give the home a fresh coastal feel. A large pocket sliding glass door disappears into the wall, creating seamless indoor-outdoor living and opening to an expansive covered back porch measuring approximately 36' x 12', perfect for entertaining, dining, or relaxing canal-side. New composite decking and front porch railings were completed in 2024, adding durability and style, and additional updates include a new HVAC system, new tankless water heater, new siding, and new impact windows throughout. The primary suite offers walk-in closets and direct porch access, while the laundry area is conveniently located on the back balcony. Offered with new furnishings both inside and out, this move-in-ready Keys getaway is ideal as a full-time residence, vacation home, or investment opportunity. Don't miss the opportunity to check out this Big Pine Key gem!

29034 Rose Dr, Big Pine
$1,174,000
3 Beds ⋅ 3 Baths ⋅ 620017 MLS
Nestled in the heart of Big Pine Key, this private canal-front retreat with screened in POOL offers the perfect blend of comfort, space, and island living. Situated on an oversized 21,438 fenced in corner lot with a private gated entrance, the property provides exceptional privacy and a peaceful setting surrounded by tropical beauty. Plenty of space for your RV, Boat Trailer and more. It's a boaters dream. Access the Atlantic or Gulf in minutes. 15,000 lb. Boat lift added in 2024. Inside, the home features 1,774 square feet of thoughtfully designed living space with 3 bedrooms and 3 bathrooms. The third bedroom has a private entrance and could be used as guest quarters or an in-law suite. The updated kitchen showcases modern finishes and functionality, while the beautifully renovated bathrooms reflect today's contemporary style and comfort. Spacious living areas and an inviting layout create an ideal environment for both relaxing and entertaining. Impact Windows and Doors. New AC year 2026. Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this canal-front property offers the privacy, upgrades, and Florida Keys lifestyle buyers are searching for. Call to schedule your private tour. Sellers are motivated.

30525 Winifred St, Big Pine
$799,000
3 Beds ⋅ 2 Baths ⋅ 620011 MLS
It's your lucky day! The last buyers had to cancel their contract for personal reasons prior to inspections. Whether you enjoy fishing and diving or prefer kayaking and paddle boarding through the beautiful waters of the Lower Keys, this updated 'Old Keys' home offers the perfect base for quick access to Bogie Channel, the Atlantic, and the backcountry. Situated on a 50' x 100' lot, the 2-story, single-family residence features a cut-in boat slip with a boat lift beneath the expansive great room, along with its own boat ramp on the side. The frame with stucco upstairs offers 1,380 square feet of living space with 2 bedrooms, 1 bath, and a spacious great room with impressive water views. The original structure has high cathedral ceilings with wood beams and beautiful hardwood floors. Generously-sized, the updated kitchen includes abundant cabinet space, granite countertops, and a large island. The CBS ground level has a grandfathered-in, 600 sq. ft. living area that provides the 3rd bedroom and 2nd bathroom creating an ideal in-law suite; plus 300 sq. ft. devoted to storage as well as the washer and dryer. Impact-resistant windows were installed upstairs in 2021, and new ductless AC/heat systems were added both upstairs and downstairs in 2022. Panel shutters protect the downstairs jalousie windows. Please note that the upstairs and downstairs living areas are not connected by an interior staircase. This long-established neighborhood is also home to local favorites and landmarks including the No Name Pub, No Name Bridge, and the Old Wooden Bridge Resort and Marina with boat ramp. Sellers would appreciate post-closing occupancy of 30-60 days.

30937 Baileys Ln, Big Pine
$1,295,000
3 Beds ⋅ 2 Baths ⋅ 620002 MLS
Homes offering this level of detail, space & modern construction are a rare find in the Lower Keys. Built in 2023 in desirable Pine Channel Estates, this exceptional waterfront home offers 75' of dockage on a deep, wide canal with quick access to Pine Channel. Tucked in far enough to avoid traffic noise, yet moments from open water, the location delivers the best of the Lower Keys lifestyle. Bonus-Low insurance costs! Designed with both luxury & functionality in mind, this split floorplan home showcases extensive upgrades & designer finishes throughout including crown custom built-ins, crown moulding, recessed LED lighting, upgraded designer fixtures, impact windows & doors, & durable Hardie board siding. The stunning kitchen serves as the centerpiece of the home with quartzite countertops, custom cabinetry, premium finishes & abundant space to gather and entertain, while quartzite carries through the bathrooms for a cohesive upscale feel. The expansive upstairs screened lanai creates an ideal indoor/outdoor living space with designer details throughout and plenty of room to relax, dine & entertain year-round. Downstairs offers expansive covered entertaining areas, outdoor shower, hot tub & 300 sq ft enclosure perfect for storage, tackle room, gym, workshop or additional flex space. True laundry/utility room adds practicality rarely found in Keys homes. Custom closet built-ins throughout. Additional features include a cistern (not currently in use), exceptional indoor & outdoor living space, & a beautifully designed waterfront setting built for boating, entertaining & enjoying the Keys lifestyle. The clear canal water here is a standout rarely found elsewhere. Double framed dock for boat lift. Homeowners/Windstorm=$2,645. Flood=$2,164

29663 Saratoga Ave, Big Pine
$850,000
5 Beds ⋅ 3 Baths ⋅ 619979 MLS
Welcome to your perfect Florida Keys retreat! Situated on a spacious 5,250 s/f lot, this versatile waterfront property offers two separate living units, making it ideal for multi-generational living, vacation use, or income-producing potential. The upper level features 3 bedrooms and 2 bathrooms with bright, comfortable living spaces designed for relaxed island living. The lower unit offers 2 bedrooms and 1 bathroom and is currently rented month-to-month for $4,000, with the tenant also utilizing the upstairs portion of the home. This property is loaded with upgrades and features for convenience, security, and outdoor enjoyment, including a shingle roof approximately 8 years old, impact windows throughout, and two elevated A/C units that are less than 4 years old. Boating and recreational enthusiasts will appreciate the 50-foot dock, along with existing preparation for water and electricity service for boats on the canal. Additional highlights include a 16-camera security system, RV preparation, and readiness for an electric vehicle charging station. Perfectly located just a 5-minute walk from the coast, this exceptional property combines waterfront lifestyle, flexibility, and modern upgrades in one incredible Florida Keys opportunity.

3610 S Seas St, Big Pine
$1,299,900
2 Beds ⋅ 2 Baths ⋅ 619915 MLS
Welcome to your private paradise in the Lower Keys! This beautifully updated 2-bedroom, 2-bathroom two-story home offers the ultimate island escape with unmatched privacy -- no direct neighbors on any side, just peaceful surroundings, tropical landscaping, and the charm of the native Key Deer. Designed for true Florida Keys living, the outdoor space is a showstopper. Enjoy a brand-new heated concrete pool, concrete dock with both a boat lift and jet ski lift, and an elevated sundeck perfect for sunbathing or taking in serene canal views. The professionally landscaped backyard creates a lush tropical retreat complete with paver decking and a tiki hut ideal for entertaining or relaxing poolside. Inside, the home features numerous upgrades and renovations throughout. The fully enclosed and renovated ground level provides excellent guest accommodations, entertaining space, and additional storage, along with a separate laundry room for added convenience. Both levels are equipped with impact windows and doors, as well as electronic roll-down screens for shade and storm protection. Whether you're boating, entertaining, relaxing by the pool, or enjoying the surrounding wildlife, this exceptional property captures the very best of Lower Keys waterfront living.

3746 Park Ave, Big Pine
$869,000
2 Beds ⋅ 2 Baths ⋅ 619841 MLS
Seller Welcomes Offers! Tucked away on a quiet dead-end street in Big Pine Key, this beautifully updated 2-bedroom, 2-bath canal-front home offers the perfect blend of modern comfort and relaxed island living. Thoughtfully renovated throughout, the home features updated flooring, stylishly remodeled bathrooms, a sleek contemporary kitchen, fresh exterior paint, and upgraded decking and screening, creating a truly turnkey island retreat. The spacious screened porch extends the living area outdoors, providing an inviting setting to relax, entertain, and enjoy the gentle island breezes year-round. Outside, unwind along the canal and take advantage of the durable composite dock with quick boating access to Pine Channel--perfect for fishing excursions, waterfront dining by boat, or unforgettable sunset cruises. Whether you're searching for a full-time residence, seasonal escape, or weekend getaway, this exceptional property captures the charm, tranquility, and effortless lifestyle that make the Florida Keys so desirable.

3674 S Seas St, Big Pine
$899,000
2 Beds ⋅ 2 Baths ⋅ 619829 MLS
Extra adjoining lot adds additional seawall frontage and provides plenty of room for a pool, extra recreational space, and additional parking at this beautifully updated waterfront property in Big Pine Key. This well-maintained home features impact-resistant windows and doors, along with a tranquil canal-side screened porch that creates the perfect setting to relax and enjoy the Florida Keys lifestyle. Inside, you'll find two comfortable bedrooms and two renovated bathrooms, including a spacious primary shower. Luxury vinyl flooring runs throughout the home, offering both style and durability. Additional upgrades include a tankless hot water heater and abundant shaded space underneath the home, ideal for outdoor entertaining, storage, or covered parking. Boating enthusiasts will appreciate the impressive 100 feet of waterfront, featuring an 80-foot concrete seawall along with a wooden section connecting the two concrete seawalls across both lots. The entire perimeter of the property is fenced, providing added privacy and security. A Home Warranty is offered with this property. With expanded outdoor space, updated features, and exceptional waterfront access, this property offers a rare opportunity to enjoy relaxed Florida Keys living in Big Pine Key.

29114 Cedar Dr, Big Pine
$1,055,000
3 Beds ⋅ 2 Baths ⋅ 619820 MLS
Accessibility elevator! Welcome to your Lower Keys retreat where comfort, and coastal living come together beautifully along with the convenience of an interior elevator. Situated on the desirable boating canal system of Pine Channel Estates, this 3 bedroom, 2 bath home is designed for those who appreciate the water based lifestyle. Inside, soaring vaulted ceilings create an open and airy atmosphere throughout the home, while the interior elevator offers effortless and/or handicap access and convenience. Expansive living spaces flow seamlessly onto a large screened deck and two additional open-air decks off of the canal side bedrooms, all perfectly positioned to capture peaceful canal views. Elevated above flood and built to withstand severe weather conditions with impact resistant windows and metal roof. For boating enthusiasts, this property is truly exceptional. Featuring two boat docks and a 12,000-pound boat lift, you'll enjoy quick and easy access to the ocean and gulf side right from your backyard. Whether you're heading out for a day on the boat, entertaining guests outdoors, or simply relaxing in the coastal breeze, this home delivers the ultimate waterfront lifestyle. **NOT AVAILABLE TO SHOW AUGUST 5-15** **Handicap accessible with interior elevator shaft ~ Sewer assessment is paid in full ~ Fire & Liability (homeowners) insurance $2,318.30**

29555 Enterprise Ave, Big Pine
$899,000
1 Beds ⋅ 1 Baths ⋅ 619787 MLS
This recently built canal front home is situated in a highly desirable area of Big Pine just minutes to the open water. The home has a bright open kitchen with plenty of cabinets, stainless appliances, attractive tile backsplash and built in table with seating overlooking the living area.......From the bedroom with adjoined bathroom there are partial ocean views. There is also a utility room with walk-in closet and washer/dryer next to the bedroom......for convenience and easy maintenance there are impact windows and doors and ''Hardie board'' siding.......There is a wrap-around screened porch from which to enjoy views of the canal and partial open water view.......The very spacious 5250 sf lot with 70 ft of seawall benefits from having a large storage enclosure plus carport and plenty of room for an RV, trailer storage or to build a pool.

31342 Ave I, Big Pine