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$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

$1,450,000
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

$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

$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

$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

$520,000
2 Beds 1 Baths 620103 MLS
Escape to your own private tropical oasis in the heart of Big Pine Key. Hidden behind lush mature landscaping and swaying palms, this charming 2-bedroom, 1-bath home offers the privacy, tranquility, and island lifestyle that make the Lower Keys so desirable. The flood policy is $977 and assumable!! Situated on a 6,000-square-foot lot in the sought-after Eden Pines neighborhood, this concrete home features a durable metal roof, tile flooring throughout, and an inviting open living area filled with natural light. A spacious screened porch extends the living space outdoors, creating the perfect setting to enjoy morning coffee, entertain friends, or simply relax and enjoy the peaceful tropical surroundings. The fully fenced yard provides exceptional privacy and ample room for gardening, pets, outdoor activities, or future enhancements. A detached storage shed offers convenient storage for tools, fishing gear, bicycles, and all your island toys. One of the neighborhood's hidden gems is the nearby community boat ramp, providing convenient access to the waters of the Lower Keys. Enjoy easy days on the water exploring the backcountry, fishing, kayaking, paddleboarding, or heading offshore for world-class boating adventures--all without the cost of owning a waterfront property. Located in the desirable Eden Pines community, this home is just minutes from the National Key Deer Refuge, Blue Hole, Bahia Honda State Park, local restaurants, shopping, and marinas. Big Pine Key offers a relaxed island atmosphere while remaining conveniently located approximately 30 miles from Key West and less than 30 minutes from Marathon. Whether you're searching for a full-time residence, seasonal getaway, or investment opportunity, this tropical retreat offers an exceptional opportunity to enjoy the Florida Keys lifestyle at an attractive price point

29284 Coconut Palm Dr, 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

$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

$1,435,000
4 Beds 2 Baths 619761 MLS
Embrace island living in your own tropical paradise, where comfort, space, and waterfront access create a remarkable oasis for boating and relaxation. Welcome to Pine Channel Estates, the ultimate destination for anglers and water enthusiasts. Currently operating as a successful vacation rental, this gem is ideal for a second home that can offset some of the annual costs of ownership, and furnishings are negotiable in the sale. This elevated, solid concrete home offers quick access to both the Ocean and Gulf, just minutes from world-class adventures! Designed with the serious boater in mind, the property features a 75' concrete seawall, a 17k lb. boat lift, fish-cleaning station, and step-down dock for easy loading. This expansive 4-bed, 2-bath home is ideal for entertaining, with oversized common areas that flow seamlessly for memorable gatherings. The third-floor loft, currently used as a bonus bedroom, offers 360-degree views and a private retreat, while main-floor bedrooms are generously sized with walk-in closets for ample storage. The kitchen is well appointed with a double oven, sprawling counter space, walk-in pantry, and room to host with ease. Unique details throughout include a custom etched mirror in the primary bath that adds coastal charm. Step outside and embrace the Keys lifestyle! A spacious porch, accessible from both the living area and primary suite, is perfect for open-air dining and relaxing water views. Downstairs, the ultimate entertaining area includes a full bar with TV, a large swim spa, plus a 500 lb. ice machine and bait freezer for added convenience. The thoughtfully landscaped yard offers privacy and function, boasting a fenced backyard and ample space for RV or trailer storage. Covered parking provides unique, direct interior access out of the elements. Located in a quiet neighborhood close to dining and shopping, this home blends tranquility with convenience. It is more than a home; it is a waterfront escape ready to be enjoyed!

29562 Saratoga Ave, Big Pine

$1,695,000
4 Beds 3 Baths 619740 MLS
Welcome to the ultimate angler's retreat in Tropical Bay Estates. This elevated concrete waterfront home offers quick access to both the Atlantic and Gulf, putting you in the heart of world-class fishing and diving. Located just a few miles from Bahia Honda State Park, you're ideally positioned for elite tarpon fishing, backcountry action, reef trips, and offshore runs. The dock is built for serious fishermen, featuring a 50' concrete seawall, 15,000 lb boat lift, fish cleaning station, underwater fish lights, and a shaded dockside area with crank out awning, everything you need for seamless days on the water. Built in 1993 with solid concrete construction, the home is designed for durability and comfort, with impact windows and doors, a new metal roof, updated A/C system, and thoughtful upgrades throughout. Inside, you'll find a spacious primary suite with California closet system, whirlpool tub, walk-in shower, and dual sinks, along with two oversized screened lanais to enjoy the coastal breeze. The ground level offers over 1,100 sq ft of enclosed garage space, perfect for storing gear, tackle, and water toys, along with a 250 lb ice maker, multiple freezers. Additional features include a cargo lift, whole-house water filtration and softener system, and tankless hot water. After a long day on the water, unwind just a few minutes walk away at No Name Pub, a local favorite known for its laid back Keys vibe. This is more than a home, it's a Keys Fisherman's paradise Built like a fortress!

30363 Flamingo Ln, Big Pine

$4,650,000
3 Beds 3 Baths 619696 MLS
Escape to ''The Castle'', a luxurious gated Gulf-front estate rarely spanning 1.14 acres on Big Pine Key. This extraordinary retreat is a graceful blend of architectural grandeur and coastal charm, thoughtfully designed for both relaxation and recreation. Boaters will delight in an unparalleled offering of 235 feet of dockage total: 140 feet of protected canal-front dockage featuring a 15,000 lb lift, cut-in slip, boat ramp, plus a 95-foot open water pier-style dock with additional 15,000 lb lift and cut-in slip, set against a 130-foot concrete seawall for secure, convenient access. Crafted in 2014 with solid poured concrete, impact-rated windows and doors, whole home generator and elevator, the home is built for enduring elegance. With over 4,600 square feet of refined interior space, this 3-bedroom, 3-bathroom estate is an architect's masterpiece with its stately presence, curved openings, and striking double staircase. Step inside to a breathtaking panorama of endless open Gulf waters and nightly sunset performances. The chef's kitchen is a dream for entertaining, featuring 10.5-foot island with seating for 8, dual sinks, refrigerators, and ovens, plus Jenn-Air 6-burner gas cooktop with pot filler, and rich wood cabinetry. Enjoy the grand family room with Gulf views, host movie nights in the private theater, or dine al-fresco under the stars. Nearby, find the full-size laundry room and storage. The top-floor primary suite is a sanctuary, offering sweeping water views, home office, private lounge with kitchenette, spa-like bath with clawfoot tub, tiled shower and generous walk-in closet with additional laundry. Outside, the resort-style pool beckons with a spa, water features, LED lighting, plus heater and chiller. Rooftop deck with 180-degree views, and unrivaled sunsets await. Offered fully furnished, this is ultimate Keys living without compromise!

3742 Seagrape St, Big Pine

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