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$649,000
3 Beds ⋅ 2 Baths ⋅ A12059984 MLS ⋅ Sands Subd BLDG.
Built in 2021, this well-maintained stilt home in Big Pine Key offers 3 bedrooms and 2 baths with 1,248 sq ft of living space. Constructed to current Monroe County code with concrete piling foundation, Hardie board exterior, and metal roof. Roof, A/C, and plumbing are all approximately 5 years young.NO HOA! Priced to sell, a rare opportunity to own in the Florida Keys near the water. Bring your vision and make it your own!

31169 Avenue G, Big Pine
$840,000
2 Beds ⋅ 2 Baths ⋅ A12045192 MLS ⋅ Port Pine Heights 2nd Add BLDG.
Beautifully Renovated Single-Family Home in the Florida Keys This stunning 2-bedroom, 2-bathroom home with extra guess room downstairs, fully renovated in 2024, is perfect for fishing enthusiasts and those seeking a serene island lifestyle. The property boasts a 50-foot dock with no bridges to the ocean, ideal for quick access to the water. Located in a quiet neighborhood, this home features a 2018 roof and a brand-new AC installed in 2024. Rentals are permitted, making it a great investment opportunity. For a full-price offer, the home comes fully furnished, including all pool tables. Don't miss out on this dream home in the Keys! SELLER MOTIVATED!!Show: 24 Hour Notice; Alarm System; Call List Agent

3635 Trade Winds St, Big Pine
$2,300,000
4 Beds ⋅ 3 Baths ⋅ A12036927 MLS ⋅ Doctors Arm BLDG.
Brand-New Waterfront Home - Completed and Move-In Ready. This elevated CBS single-level residence offers 4 bedrooms, 3 bathrooms, 10-foot ceilings, impact-rated windows and doors, metal roof, stainless steel appliances, quartz countertops, open-concept living, screened porch, private pool, and covered parking below. Built for coastal living, the CBS structure, impact openings, elevated design, and metal roof provide durability, strength, and insurance-friendly features. Allocated dockage includes an approx. 45' access walk to a 91' platform, creating a great setup for boating, kayaking, paddleboarding, and waterfront views. Set on a 14,680-square-foot lot with approx. 75' of waterfront frontage, the property captures panoramic Bay/Gulf-front water views and sunrise exposure. Enjoy access via Bogie Channel, with backcountry access and fast open-water routes to the Atlantic Ocean and the Gulf. Nearby Looe Key Reef is a favorite for snorkeling and scuba diving. Located on the Big Pine Key side of the Bogie Channel Bridge to No Name Key, this setting offers water views and island privacy. The property can be used as an investment property for vacation rental use, adding flexibility and income appeal. Near the iconic No Name Pub and surrounded by the natural beauty of Big Pine Key, where Key Deer are part of everyday island life. Big Pine Key offers conveniences nearby, while still delivering a quiet waterfront lifestyle. Construction is complete and ready for immediate occupancy.

30995 Watson Blvd, Big Pine
$1,150,000
4 Beds ⋅ 3 Baths ⋅ A12018191 MLS ⋅ Pine Channel Estate Sec 2 BLDG.
Waterfront retreat with excellent boating access in the heart of Big Pine Key! Home has 15k boat lift, fish cleaning table and clear deep canal. This elevated home features a private dock, canal frontage, and plenty of room for boats, trailers outdoor entertaining and out door showers. Open-concept living areas, abundant natural light, and spacious porches create the perfect Keys getaway or full-time residence. Conveniently located near world-class fishing, diving, turquoise blue waters, sandbars and the Lower Keys’ laid-back charm. 4 bedrooms, 3 baths, there are 2 bedrooms and 1 bath upstairs and 2 bedrooms, 2 baths downstairs. Home is fully furnished and ready to use.

29565 Flying Cloud Ave, Big Pine
$750,000
2 Beds ⋅ 2 Baths ⋅ A12015711 MLS ⋅ Cahill Pines And Palms BLDG.
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.

251 Pelican Ln, Big Pine
$1,199,000
2 Beds ⋅ 2 Baths ⋅ A12012572 MLS ⋅ Pine Channel Estate Sec 2 BLDG.
Embrace the serene beauty of island living with this delightful 2-bedroom, 2-bathroom home nestled on a double-fenced lot in Big Pine Key. Perfectly positioned along a scenic canal, this property offers Southern charm, with an inviting wraparound porch to enjoy the gentle breeze and picturesque views. This home is ideal for both relaxation and entertaining. Step outside to a seawall that leads directly to the water, offering easy access for boating and water activities. Whether you're a seasoned boater or a weekend enthusiast, this canal-front location provides fantastic opportunities for adventure right at your doorstep. The property offers plenty of storage space, ensuring room for all your gear and toys. There's even space to add a pool for those sunny Florida days. A garage adds to the convenience, making this home both functional and full of potential. Don't miss the chance to own this piece of paradise, where comfort, coastal living, and a vibrant island lifestyle meet.

29662 Independence Ave, Big Pine
$3,899,000
6 Beds ⋅ 6 Baths ⋅ A11980368 MLS ⋅ Long Beach Estates BLDG.
Welcome to The Barnacle Bed and Breakfast, a rare oceanfront offering in Big Pine Key where island living meets income opportunity. This beautifully updated waterfront property allows you to live the Florida Keys lifestyle while hosting it or operate a turnkey hospitality investment in one of the most sought-after settings in the Lower Keys. The property has undergone an extensive renovation over the past two years and is now updated, featuring a new roof, new windows, remodeled interiors, and upgraded throughout. Offered fully furnished, the estate includes multiple structures with indoor and outdoor kitchens, central water, and electric service, allowing for immediate enjoyment and operation. Enjoy approximately 150 feet of direct oceanfront on the main parcel, complemented by additional parcels offering flexibility and long-term potential. Boating enthusiasts will appreciate the private beach, bay and ocean access, CBS dockage, private boat ramp, and on-site boat docking, making life on the water effortless. Currently operating as a bed and breakfast with strong daily rental performance, the property is now fully operational at capacity, presenting immediate income potential. Whether envisioned as a private waterfront retreat, an owner-operated B&B, or an investment opportunity, this is a truly unique chance to own a piece of paradise in the Florida Keys.

1557 Long Beach Dr, Big Pine
$1,055,000
3 Beds ⋅ 3 Baths ⋅ A11977420 MLS ⋅ Eden Pines BLDG.
Enjoy Florida Keys waterfront living in the heart of Big Pine Key. This canal-front home with a full concrete seawall and direct boating access offers the perfect opportunity to experience the relaxed Lower Keys lifestyle surrounded by world-class fishing, diving, and boating. The elevated main home features a 2 bedroom, 2 bathroom layout with an open living area, spacious kitchen with built-in cabinetry extending into the dining area, and pocket sliding doors leading to a screened porch overlooking the canal—an ideal spot to enjoy the island breeze. Downstairs is a pre-FIRM finished enclosure with approximately 480 sq ft including an additional 1 bedroom and 1 bathroom, providing flexible space for guests, hobbies, or storage. The fenced lot, drive-through garage, and large utility/laundry area offer plenty of room for boating gear and outdoor equipment. A rare feature is the added privacy with no neighbors on one side, as the county owns the two adjacent lots which will remain undeveloped. Located in the desirable Eden Pines neighborhood, just minutes from the community boat ramp, local restaurants, and shopping, and approximately 30 minutes to Key West. Close to Bahia Honda State Park, the National Key Deer Refuge, and world-class snorkeling and diving at Looe Key Reef.

29051 Magnolia Ln, Big Pine
$750,000
3 Beds ⋅ 2 Baths ⋅ A11958850 MLS ⋅ Hollerich Subd BLDG.
Nestled in the heart of Big Pine Key, this charming A-frame home offers classic Florida Keys character on an oversized double lot with canal frontage and excellent boating access to Bogie Channel. Built in 1973 and constructed with metal beams, this just-over-1,000-square-foot home blends durability with coastal charm. Additional highlights include an on-demand hot water heater, a seawall, and ample storage for all your island and boating gear. With plenty of room to expand or customize, the expansive property offers endless possibilities. Ideally located just minutes from Big Pine Community Park, this home provides easy access to nature trails, recreation, and local amenities. Whether you're seeking a full-time residence, weekend retreat, or investment opportunity, this canal-front property with quick access to open water is a rare find in the Lower Keys.

31033 Hibiscus Dr, Big Pine
$2,700,000
4 Beds ⋅ 3 Baths ⋅ A11953691 MLS ⋅ Tropical Bay BLDG.
Walk into this luxurious palace with captivating open water views. Light colors accenting the beautiful interior with matching large Porcelain floors and counter tops enhancing the large windows bringing the natural light inside. Gourmet kitchen for any chef to create great memories viewing the sunsets. Open patio with a great view of the pool and the outdoor entertaining areas. Four roomy suites for your family and friends to enjoy with oversized closets and high ceilings for your pleasure. 15,000-pound boat lift for your convenance at your dock side.

1553 Sunrise Dr, Big Pine
$660,000
3 Beds ⋅ 3 Baths ⋅ A11942155 MLS ⋅ Cahill Pines And Palms BLDG.
A completely remodeled property featuring a new roof installed in 2024, new flooring, and termite treatment performed in 2025. It comes fully furnished and boasts an ideal location just 30 minutes from Key West. The home is situated close to restaurants, schools, beaches, recreational facilities, and everything needed to enjoy a peaceful and pleasant lifestyle. Additionally, the property includes an extra game room—fully finished, complete with its own private bathroom and separate entrance. The seller will contribute up to $10,000 toward the buyer's closing costs.

74 Pelican Ln, Big Pine
$2,069,000
3 Beds ⋅ 2 Baths ⋅ A11916862 MLS ⋅ Tropical Bay BLDG.
Beautiful Waterfront Ocean & Canal property 3BD/2BA concrete block (CBS) direct ocean and canal access Property sits at 10 ft. elevation lot and features a durable aluminum roof, impact-resistant windows, and low-maintenance construction built for longevity in the Florida Keys. A 75 ft concrete dock, ideal for larger vessels, water toys, and fishing trips straight to open water. Spacious outdoor area provides room for entertaining, relaxing, and enjoying the coastal lifestyle. Interior highlights include an open living/dining layout with abundant natural light, a functional kitchen, and comfortable bedroom spaces. Perfect for full-time living, a vacation retreat, or investment property. Strong construction and unmatched waterfront access make this a must-see Keys home.

1733 Sunrise Dr, Big Pine
$5,390,000
3 Beds ⋅ 3 Baths ⋅ A11877495 MLS ⋅ Port Pine Heights 2nd Add BLDG.
Escape to “The Castle”, a luxurious gated Gulf-front estate spanning 1.14 acres on Big Pine Key. Built in 2014 with poured concrete, impact windows/doors, elevator, and generator, this 4,600+ sq. ft. masterpiece offers 3 bedrooms, 3 baths, and breathtaking Gulf views. Boaters enjoy 235’ of dockage: 140’ protected canal dock with lift, ramp, and slip, plus 95’ open-water pier dock with lift and seawall. Inside, a chef’s kitchen with 10.5’ island, dual sinks, Jenn-Air gas range, and wood cabinetry flows to a grand family room, theater, and rooftop deck. The top-floor primary suite boasts water views, office, lounge, spa bath, and custom closet. Outside, a resort-style pool with spa, heater/chiller, and LED lighting completes this rare Florida Keys retreat.

3742 Seagrape St, Big Pine