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216 Newfound Blvd, Big Pine
$800,000
3 Beds ⋅ 2 Baths ⋅ 618879 MLS
A true tropical oasis nestled on a 6,600 sq ft lot with lush landscaping and a mature mango tree. Make this well maintained property your new home or INVESTMENT property. Currently in a successful vacation rental program. Fenced in for privacy and that sense of peace and tranquility. The backyard features a 14 x 30 custom concrete POOL with heater, chiller and colored lights. 7 x 7 spa tub and waterfall. Downstairs enclosure storage 20 x 34. Plenty of room for parking with RV parking and connections. 3 bedrooms and 2 bathrooms with 1360 sq ft of living space. Double French doors and impact resistance windows allow natural light throughout the home. Spacious open floor plan. Kitchen updated with white corian counter tops, backsplash and bar. Hall bathroom updated with fully tiled walk in shower and glass door. Upstairs covered balcony patio with plenty of space for dining outdoors and entertaining guests. Located on a plugged canal for convenience of kayaking, paddle boarding or swimming from your 15 x 40 foot wooden dock. This is not a boating canal. Local boat ramps are within 5 - 7 minutes. This island gem is being offered turn key, ready for you to start living your paradise lifestyle. It's truly a must see! Call for your private showing today.

216 Newfound Blvd, Big Pine
30937 Baileys Ln, 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.

30937 Baileys Ln, Big Pine
31226 Hollerich Dr, Big Pine
$799,000
2 Beds ⋅ 2 Baths ⋅ 619707 MLS
Buy a slice of the Florida Keys with this sturdy CBS 2-2 located in one of the most convenient locations available! Boating is a short ride to Bogie channel which offers easy access to both the Gulf of Mexico and the Atlantic! World-class fishing at your fingertips! Also nearby is Big Pine Park, and many amenities like the Winn-Dixie shopping center. More about the house; the first floor currently is secure storage and covered parking. Moving up the steps you will be on the back porch overlooking the 60ft. of concrete dockage. Inside, the home has been tastefully remodeled, furnishings are currently negotiable! Improvements soon to be made not currently shown in photos - paint touchups in the guest bedrooms, and a coat of sealant over the back porch!

31226 Hollerich Dr, Big Pine
3686 Gulfstream St, Big Pine
$790,000
2 Beds ⋅ 2 Baths ⋅ 619308 MLS
Key Deer, Quick Access to Pine Channel, Canal Views & Updated Island Living: Your Florida Keys Dream Awaits! Imagine: breathtaking sunsets painting the sky, the gentle presence of Key Deer just outside your fence, and the tranquility of canal-front living in the heart of the National Key Deer Refuge. This charming 2-bedroom, 2-bathroom home offers a rare opportunity to live in harmony with nature without sacrificing modern comfort. Spend your days boating, fishing, diving, or simply relaxing on your canal-side wrap-around porch, soaking in the vibrant colors of the sunset. Key Deer sightings are a regular occurrence, making this property a true paradise for nature lovers. Enjoy 50 feet of canal frontage with excellent boating access, a control depth of 3', and quick access to open water. Venture out to the popular hot spots on the water, like Picnic Island, or explore Pine Channel from the Atlantic to the Gulf of America. Fish, lobster, and crabs await. Inside, soaring cathedral ceilings create a spacious and airy atmosphere. The updated kitchen features stainless steel appliances, granite countertops, and wood cabinets, flowing seamlessly onto the canal-side porch, perfect for morning coffee or evening cocktails. Upstairs offers a spacious private master suite with a soaring ceiling, a walk-in closet, and a master bath with a soaking tub. Downstairs is the second room, a guest bath, a full-size laundry room with lots of storage, a kitchen, a large dining area, and a living room. 2018 Meticulously updated for comfort and peace of mind, this home boasts impact windows, a new front door, a standing seam metal roof, and updated electrical . Durable Hardie board siding and facia protect the exterior of the home. The yard is fully fenced, adding to the property's appeal. Plus ample storage in the large enclosed lower level. Low insurance rates add to the value! Don't miss your chance to make this island dream a reality! Pre-qualification is available.

3686 Gulfstream St, Big Pine
30471 Coconut Hwy, Big Pine
$790,000
3 Beds ⋅ 2 Baths ⋅ 614717 MLS
Experience the charm of this beautifully renovated split-level home, designed with privacy and elegance in mind. The elevated master suite ensures a peaceful retreat, while additional spaces offer the versatile of an office or separate family room perfect for relaxation or entertaining. Step through the bedroom doors onto a spacious deck, where you can enjoy views of the meticulously landscaped backyard and expansive pool. Nestled on a generous double lot, this property features wonderfully lush greenery, providing seclusion in the tranquil setting of Big Pine Key. Every detail has been thoughtfully considered, from the stylish Plantation shutters and open-concept living area to the new metal roof and AC system. This home truly offers everything you could wish for. Schedule your showing today and experience all the beauty this home has to offer!

30471 Coconut Hwy, Big Pine
3922 Gordon Rd, Big Pine
$789,000
2 Beds ⋅ 2 Baths ⋅ 619213 MLS
Not every canal-front home in the Keys feels like a destination. This one does. 3922 Gordon Road is an elevated 2BR/2BA waterfront retreat in Big Pine Key offering the lifestyle buyers come here for--easy boating, inviting outdoor living, and a home that feels like an escape from the moment you arrive. Bright coastal interiors, an open living/dining/kitchen layout, and a screened porch create a relaxed yet polished atmosphere upstairs, while the expansive covered space below adds exceptional flexibility for entertaining, lounging, storage, and covered parking. Outside, the property is dialed in for life on the water with 50' of dockage, a concrete seawall, and a 17,000 lb boat lift just moments from open water. An above-ground pool completes the picture, adding the perfect place to cool off after a day on the boat. Stylish, functional, and full of lifestyle appeal, this is a standout Big Pine Key waterfront opportunity. Home has all hurricane windows and shutters.

3922 Gordon Rd, Big Pine
3672 Fox St, Big Pine
$740,000
3 Beds ⋅ 3 Baths ⋅ 618276 MLS
Price and lifestyle come together in this canal-front home in Big Pine Key. Offering 3 bedrooms and 3 baths, this property is ideal as a full-time residence, vacation getaway, or investment opportunity. Inside, you'll find a bright, open floor plan with high ceilings and an updated kitchen featuring stainless steel appliances and granite counters. The primary suite opens to a private balcony, while two additional bedrooms provide flexibility for guests or rental potential. Outdoor living is where this home shines--enjoy a large deck, private nature trails, and a 12-foot dock with patio space for boating and waterfront relaxation. Nestled near Port Pine Heights Park and just minutes from top fishing and local conveniences, this is your chance to own a slice of Keys tranquility.

3672 Fox St, Big Pine
1817 Watson Blvd, Big Pine
$725,000
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
1634 Lantana Ln, Big Pine
$700,000
2 Beds ⋅ 2 Baths ⋅ 617945 MLS
Custom-built 2-bedroom, 2-bathroom home (1987) situated on a boating canal in the sought-after Eden Pines neighborhood of Big Pine Key where the Key Deer roam. Short stilted home located on a 6,000 sq. ft. lot the property offers 60 feet of concrete seawall ideal for your boat of choice, with excellent boating access via Pine Channel. Boaters should note two bridges en route with approximate clearances of 8.5 ft and 10 ft; canal depth offers approximately 3 ft of draft. The home features an updated kitchen with all-new appliances (2021) and gas a range. Desirable split floor plan with both bedrooms accessed by a short set of stairs and a side screened porch in the back of the home--perfect for relaxing at the end of the day. Additional highlights include a new HVAC system (2020), roof replacement (2018), ample storage beneath the home. Miami-Dade approved accordion shutters for added storm protection. Well suited as a primary residence, vacation home, or long-term rental investment.

1634 Lantana Ln, Big Pine
30246 Watson Blvd, Big Pine
$700,000
3 Beds ⋅ 2 Baths ⋅ 618372 MLS
Discover your dream home on Big Pine Key at this expansive 37,500 sq. ft., property totaling 6 lots that combines privacy, nature and convenience. Nestled in a serene setting with tropical landscaping and thoughtful features, this home offers a massive yard that goes from street to street and is surrounded by a 6' stockade fence allowing lots of safety and room for kids and pets to play and roam. The 3 Bedroom 2 Bath home offers an open floor plan highlighted with soaring ceilings and garden views from all rooms with no neighbors in sight. The kitchen is a culinary delight with a central island with peninsula seating, wood cabinetry and abundant counter space. Whether you're preparing a gourmet meal or a quick snack this kitchen is equipped for it all. A convenient pantry and a laundry closet add to the functionality, ensuring everything has its place. Enjoy morning coffee or evening cocktails on either the front or back porch while watching key deer roam. The home's split floor plan provides privacy and comfort. The primary suite is a private retreat with a walk-in closet and a en suite bathroom. Additional bedrooms feature engineered hardwood floors and offer plenty of space for family or guests. The property's outdoor spaces are nothing short of extraordinary. Two tranquil ponds on either side of the lot enhance the peaceful ambiance and can be filled using the private well. A large cistern is used for watering the grounds, abundant in native and lush landscaping creating a serene environment. A stone walkway leads to a spacious 20x20 shed allowing for plenty of room for all of your toys. A garden shed tucked at the back of the lot provides additional storage, while a downstairs covered lanai offers an ideal spot for entertaining, barbecuing, or unwinding in the shade. This property is as practical as it is beautiful, with a covered carport, trailer storage, room for pool and RV and plenty of parking for guests.

30246 Watson Blvd, Big Pine
29048 Iris Dr, Big Pine
$693,800
3 Beds ⋅ 2 Baths ⋅ 619078 MLS
This 50' wide canal provides great boat access to the Atlantic and back country via Pine Channel for excellent fishing and diving in the stunning waters of the Lower Keys. If you're looking for a move-in ready stilt home at an entry-level price, this is it! Many updates have been made in recent years including impact-resistant windows and doors, new stainless steel kitchen appliances, water heater, vinyl plank flooring and vanities; new metal roof in 2018. Add your own personal touches and exterior updates to create your Keys paradise! The potential exists to replace the existing deck with a 30'-50' dock by going through proper permitting; ask agent for names of permitting services and dock contractors. The great room features a cathedral ceiling, abundant natural light from a south-facing picture window, and French doors opening to a covered porch with canal views. On the ground level are convenient covered parking and a large storage enclosure. The Eden Pines Colony public boat ramp is nearby; only one neighborhood bridge to go under with approximately 10.5 ft. clearance.

29048 Iris Dr, Big Pine
30968 Baileys Ln, Big Pine
$690,000
2 Beds ⋅ 2 Baths ⋅ 619189 MLS
Canal front home with boat lift. Quick access to Bogie Channel for Gulfside or Atlantic side fishing, boating and fun. Marinas nearby and boat ramps. 1.5 lots total of 75 ft. on canal. Lot is 100 ft deep. Room to park a RV or a boat trailer. Cut in boat slip with 10,000 pound boat lift. 2 vacant lots across the canal are county owned. Nieghbors on both sides are part time and across street. House is cute and cozy, perfect little getaway or home. Big 14X32 patio deck upstairs and shaded patio underneath. Concrete driveway in front and parking on other side. Fencing allowed in tier 2. Zoning is Improved subdivison. AE10 flood zone, bfe is 11. ft of the house upstairs floor. 30 miles to Key West 20 min to Marathon Concrete downstairs and hardyboard upstairs, Modified butumen roof with underlayment, Tile floors throughout. House tented for termites in 2023. On demand water heater. Impact windows upstairs. AC is Mini splits upstairs(ductless Range, Fridge, Dishwasher, Washer, Dryer. Upstairs is above flood, downstairs is not. Boat is available for purchase. Do not tresspass onto property. Shown by appointment.

30968 Baileys Ln, Big Pine
30416 Coconut Hwy, Big Pine
$660,000
2 Beds ⋅ 2 Baths ⋅ 620377 MLS
Looking for land in the Keys and a well-maintained home? This rare 25,000 sq. ft. property spans more than ½ acre, with room for a pool and/or tiki hut, RV, boat trailers, and more. The four lots are bordered by Coconut Hwy., Avenue B, and Hibiscus Ln., with vehicle access to the large, fenced backyard. The 1,497 sq. ft. CBS home blends ''old Keys'' charm with thoughtful updates, including cypress ceilings and wall accents, new quartz counters, tiled backsplash, original cypress kitchen cabinets, tile floors, solid wood doors, storage/workshop space, sheds, and an inviting porch screened on three sides. The Florida room offers potential for a third bedroom, and the half ''spa bath'' includes a whirlpool tub and sink, with potential for a second toilet. Tropical plantings attract birds and butterflies and include mango, starfruit, banana, frangipani, and lignumvitae. The 100' x 250' property includes unfenced front and rear areas where protected key deer roam freely. New metal roof in 2019; upgraded electric panel in 2025.

30416 Coconut Hwy, Big Pine
3943 Venna Rd, Big Pine
$650,000
2 Beds ⋅ 2 Baths ⋅ 617300 MLS
Welcome to your island retreat in the sought-after community of Port Pine Heights on Big Pine Key. This charming stilted waterfront home offers quick boating access to Pine Channel, perfect for those who love life on the water. Families are drawn to this serene neighborhood for its privacy, friendly Key Deer, and close proximity to No Name Key, as well as the sparkling beaches and crystal-clear waters of Content Key and Bahia Honda State Park. Enjoy the laid-back Keys lifestyle surrounded by nature trails and stunning coastal scenery. This 2-bedroom, 2-bath home features a durable metal roof, vaulted ceilings, ceramic tile floors, boat lift, and a beautiful screened-in balcony ideal for relaxing or entertaining. The spacious carport below provides ample parking and storage. Don't miss your chance to own a piece of paradise—call today to schedule your private tour!

3943 Venna Rd, Big Pine
31240 Ave H, Big Pine
$635,000
3 Beds ⋅ 2 Baths ⋅ 618307 MLS
This beautifully updated 3-bedroom, 2-bath home is truly move-in ready, featuring thoughtful upgrades throughout. The renovated kitchen offers quartz countertops, soft-close cabinetry, and premium finishes, while new luxury vinyl plank flooring runs throughout the home for durability and coastal style. The open-concept layout flows seamlessly into the living and dining areas, with sliding glass doors leading to a spacious screened-in upstairs porch—ideal for morning coffee, evening cocktails, or enjoying the tropical breeze. From the front porch, enjoy stunning views of the 4th of July fireworks over the natural estuary across the street. Recent improvements include a new exterior electric panel (2023), full termite tenting (2024), and a metal roof (2017). Hurricane shutters are included for all windows and doors, providing storm protection and potential insurance savings. The oversized, fully fenced yard offers plenty of space for pets, outdoor activities, and room to add a pool. Ample parking accommodates multiple vehicles, a boat, or an RV. The screened-in ground-level enclosure features a heavy-duty bar, perfect for entertaining or unwinding after a day on the water. With low insurance premiums and a transferable flood policy, this home is both beautiful and a smart investment. Conveniently located near local shops, boat ramps, and the community park, it's well suited as a primary residence, vacation home, or income-producing property.

31240 Ave H, Big Pine
29123 Rose Dr, Big Pine
$630,000
2 Beds ⋅ 2 Baths ⋅ 619625 MLS
Accepting a Backup offer! Welcome to your slice of paradise in the highly sought-after neighborhood of Eden Pines on Big Pine Key! This solid concrete construction home offers 2 bedrooms, 2 bathrooms, and 1,036 sq. ft. of comfortable living space, perfectly positioned on the water with a peaceful canal view. Enjoy the true Florida Keys lifestyle from your charming back porch that is ideal for morning coffee, evening cocktails, or simply soaking in the tropical surroundings. The home's durable concrete construction provides peace of mind, while the functional layout makes it a great option for full-time living, a vacation getaway, or an investment opportunity. Located in a family-friendly community, Eden Pines offers a welcoming atmosphere and convenient access to a nearby boat ramp, making it easy to get out on the water for boating, fishing, and exploring the beautiful Lower Keys. There is an RV hook up as well. Perfectly situated just approximately 30 miles from Marathon and 35 miles from Key West, you'll enjoy the balance of peaceful island living with easy access to dining, shopping, and entertainment. Don't miss your chance to own a waterfront retreat in one of Big Pine Key's most desirable neighborhoods! Great insurance rates!

29123 Rose Dr, Big Pine
31147 Ave H, Big Pine
$625,000
3 Beds ⋅ 2 Baths ⋅ 619301 MLS
Big Pine Key Pool Home - Nature Lover's Paradise! 3BR/2BA single-family home with pool, outdoor kitchen, and gazebo -- perfect for entertaining and enjoying the Florida Keys lifestyle! Located in beautiful Big Pine Key, this property offers an abundance of parking and is ideal for boating, guests, RVs, or multiple vehicles. Surrounded by the natural beauty of Big Pine Key and its famous Key deer, this home is a dream for nature lovers seeking peace, privacy, and island charm. Spacious outdoor living areas provide the perfect setting for relaxing or hosting gatherings year-round. Perfect for military families receiving summer PCS assignments and looking for a move-in-ready Florida Keys home with space to relax and entertain. Enjoy the best of Keys living with nearby boating, fishing, kayaking, dining, and wildlife viewing. A rare opportunity to own your own island retreat! Seller Motivated!

31147 Ave H, Big Pine
29172 Rose Dr, Big Pine
$614,000
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
30625 16th Ln, Big Pine
$600,000
3 Beds ⋅ 2 Baths ⋅ 618675 MLS
Want to feel as if you've gotten away from it all? Nestled on over an acre, this one-owner home is surrounded by nature, yet it's conveniently close to the grocery store, shopping, restaurants, banks and more; Key West and Marathon are within easy reach. The screened porch is wonderful for relaxing, reading, bird watching. With 1008 sq. ft. of living space, it offers 3 bedrooms and 2 baths; the 3rd bedroom is currently used as an office. Updates include new carpet November 2025, new water heater 2023, new central A/C in 2022, new staircase in 2019, and the metal roof was replaced in 2009. The 12,000 gallon, concrete cistern presently collects rainwater as the water source, and the home can be hooked up to FKAA water if one chooses; the sewer connection is complete. The parcel measures 215 x 220 ft. Well-maintained through the years, here's your opportunity to make updates to your liking without a long list of immediate to-do's. ***DON'T USE GOOGLE MAPS!*** APPRX. MM30.5 TRAFFIC LIGHT TURN NORTH ONTO WILDER RD., turn right/east on 16th Lane (says 'Private Rd.); it's just north of 17th St., house is towards end on the left.

30625 16th Ln, Big Pine
29951 Pine Channel Rd, Big Pine
$592,000
2 Beds ⋅ 2 Baths ⋅ 615774 MLS
*Back on Market & Ready for New Owners!* VA Assumable 2.625% interest rate for eligible Buyers! Total current payment $2864/mo! Inquire for more details. Welcome to your island escape! This beautifully updated 2 bedroom, 2 full bath stilted home offers the perfect blend of comfort, convenience, & coastal charm. Situated on a spacious lot in the heart of Big Pine Key, this property features a brand new gas stove, new AC, new quartz countertops, new tile floors, & a large screened-in covered porch: ideal for relaxing & entertaining. Downstairs, you'll find an oversized storage space perfect for your tools, gear, or hobby shop. Elevated construction offers lower insurance costs (with transferable flood insurance of $595/year!) & added peace of mind. Enjoy the island lifestyle with nearby dining, shopping, community parks, & quick access to US-1, all while surrounded by the natural beauty the Keys are known for. Neighboring wooded lot offers additional privacy. Don't miss this opportunity to own a move-in ready home in the heart of the Lower Keys!

29951 Pine Channel Rd, Big Pine
1258 Division St, Big Pine
$590,000
3 Beds ⋅ 1 Baths ⋅ 618153 MLS
Welcome to Your Own Slice of Island Paradise in Big Pine Key! Tucked away in the heart of Big Pine, this picture-perfect 3-bedroom, 1-bath home invites you to slow down, breathe deep, & truly enjoy island living. Set on an oversized double lot totaling 12,500 sq ft, this property is truly a private tropical sanctuary: lush, peaceful, and full of life. From the moment you step inside, soaring beam ceilings in the living area and primary bedroom create a light-filled, open atmosphere that instantly feels welcoming and expansive. Warm hardwood floors and thoughtful updates: central air, impact windows, and a metal roof blend effortlessly with the home's charm. The open, spacious kitchen is the heart of the home in a roomy open floor plan, perfect for cooking, gathering, & soaking up the little moments together. The generously sized primary bedroom offers room to unwind & dream big, with space to add an additional bathroom if desired. Every detail reflects pride of ownership & careful maintenance. A large downstairs bonus space in the enclosure allows ample storage & additional entertaining (not included in square footage). Outside, your backyard becomes a true island oasis. Mature fruit trees surround you with color, shade, and abundance: offering multiple varieties of dragon fruit, pineapple, sugar apple, Glenn mango, guava, pomegranate, Persian lime, & banana trees. Enjoy fresh eggs at your disposal from the secure chicken coop w/run on-site. Parking your boat(s), jet ski, camper, & more is a breeze! Harvest fresh fruit, entertain under the palms & stars, or simply savor quiet mornings in nature, this space feeds the soul. This is more than a home: it's a chance to live the Keys lifestyle. A rare opportunity to own a serene retreat with room to grow, relax, and put down roots in one of the Keys' most beloved communities. A must-see for anyone searching for something truly special. Transferable flood insurance available

1258 Division St, Big Pine
29961 Pine Channel Rd, Big Pine
$575,000
2 Beds ⋅ 1 Baths ⋅ 618702 MLS
Welcome to your perfect Florida Keys getaway in the heart of Big Pine Key. This charming 2-bedroom, 1-bath home offers an inviting open-concept layout that flows seamlessly between the living, dining, and kitchen areas. Natural light pours in through large windows, creating a bright, airy feel that complements the relaxed island setting. The kitchen features stainless steel appliances and a functional layout ideal for everyday living or entertaining. Step outside to enjoy ample space for gathering with friends, soaking up the sunshine, or unwinding after a day on the water. A dedicated storage area keeps all your outdoor gear organized and ready to go. Recent updates include: -On-demand hot water heater (2023) -12x20 above-ground pool (2022) -Plantation shutters (2022) -Upgraded HVAC air handling unit (2022) -Galvanized 6x10 shed for extra storage -RV hookup available Enjoy convenient access to multiple nearby boat ramps, and the benefit of being on one of the only islands between Marathon and Key West with a grocery store. Don't miss the opportunity to own a piece of paradise--schedule your showing today and start living the Florida Keys lifestyle.

29961 Pine Channel Rd, Big Pine
175 E Cahill Ct, Big Pine
$572,000
2 Beds ⋅ 2 Baths ⋅ 618528 MLS
Discover relaxed Keys living in this elevated 2 bedroom, 2 bath stilted home tucked away on a plugged swimming canal in Big Pine Key. Surrounded by two wooded vacant lots, this property offers exceptional privacy and a peaceful setting. The calm, non boating canal is perfect for swimming, kayaking, and paddleboarding, creating a true backyard oasis. An additional spiral staircase off the open covered porch leads directly down toward the canal, making it easy to enjoy the water and views anytime. Inside, the home features an open concept living area ideal for entertaining with a generous kitchen space. Recent upgrades include a metal roof, adding durability and peace of mind. Downstairs, enjoy covered parking, along with iron gates that provide added security and privacy. Elevated construction captures breezes and enhances the laid back island vibe. Whether you're looking for a full time residence, weekend retreat, or Keys getaway, this home offers a rare combination of water access, privacy, and tranquility.

175 E Cahill Ct, Big Pine
31054 Ave J, Big Pine
$570,000
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
29757 Henry Ln, Big Pine
$465,000
2 Beds ⋅ 2 Baths ⋅ 619990 MLS
Enjoy the laid back Big Pine Key lifestyle. Situated on an expansive 11,500 square foot lot, this beautifully updated 2 bedroom, 2 bath home offers space, comfort, and the feel of a manufactured home while no longer functioning as a mobile home. The home is securely affixed to wood pilings and concrete blocks on a concrete pad, creating a more permanent structure. Inside, you'll find a large open floor plan designed for comfortable everyday living and easy entertaining. The spacious primary suite features an oversized bathroom and walk in closet. New flooring throughout adds a fresh, updated feel to the entire home. Enjoy outdoor living from both the welcoming front porch and the back deck, perfect for relaxing or entertaining. Dedicated laundry room with additional pantry storage. Recent improvements include: Metal roof, All new impact windows, and Central A/C. Schedule your private showing today and discover the possibilities this Keys property has to offer.

29757 Henry Ln, Big Pine
31037 Ave D, Big Pine
$455,000
3 Beds ⋅ 2 Baths ⋅ 618815 MLS
This is a large Modular HOME on Big Pine Key that is permanently affixed to concrete pilings and is elevated above the 8' flood plain-which helps keep flood insurance reasonable. It is located in a tranquil setting with land that is owned by Monroe County on two sides and a spacious interior and inviting layout with ample natural light. The home has a well-appointed kitchen, area for washer and dryer and a large living area. Two of the three bedrooms have walk in closets and the third is a larger master bedroom. One of the two bathrooms has double sinks and a tub and separate shower. It has a metal roof that was installed in 2018, central AC/heater new in August 2025, and a brand new 40 gal. hot water heater. The flooring is ceramic tile throughout and there are four ceiling fans. There is enough outdoor space to enjoy nature, the Florida sunshine, and the Key deer the walk through the property daily. Conveniently located with easy access to the local amenities and natural beauty of the Keys. Don't miss this opportunity to experience island living at an affordable price!

31037 Ave D, Big Pine
29771 Henry Ln, Big Pine
$450,000
3 Beds ⋅ 2 Baths ⋅ 619739 MLS
Located in desirable Big Pine Key, this property offers an opportunity to enjoy island living on a double lot. Situated on a quiet street, the home features a functional layout and is surrounded by a fence complete with mature tropical landscaping providing privacy and a relaxed setting. A standout feature of the property is the inground pool, creating a private outdoor space for cooling off, entertaining, or simply enjoying the laid-back Keys lifestyle. The home is spacious with and open floor plan. The primary bedroom and bathroom on the back of the home for added privacy while 2 additional bedrooms and a bathroom on the opposite side of the home. The oversized lot features an accessory unit with screened in patio, additional outdoor room for parking, storage, gardening, or future enhancements. Updates including new floors and personal touches. The home has the potential to serve as a comfortable full-time residence, seasonal getaway, or rental investment. Conveniently located near boating, fishing, nature preserves, and local amenities, this property provides access to everything Big Pine Key is known for--outdoor recreation, wildlife, and a quiet island atmosphere.

29771 Henry Ln, Big Pine
29146 Hibiscus Ln, Big Pine
$438,000
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
31017 Ave I, Big Pine
$399,000
2 Beds ⋅ 2 Baths ⋅ 621399 MLS
Double lot with mobile home and storage in quiet area full of nature and key deer in big pine key. Statistical purposes only.

31017 Ave I, Big Pine
31042 Ave J, Big Pine
$335,000
2 Beds ⋅ 1 Baths ⋅ 619249 MLS
Located only a few blocks to the Big Pine Community Park, with lots of vacant government land around it and only a few blocks to the water, this home has lots of potential for someone to put their finishing touches on it and make it their own. This 2/1 with vaulted ceilings, metal roof, newer A/C and walk around deck are a perfect canvas for the new owner. The home does have visible termite damage and for that reason a cash offer is preferred. Please submit proof of funds when requesting a showing.

31042 Ave J, Big Pine

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