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$1,500,000
A12060300 MLS
ADDRESS: 99 DON QUIXOTE KEY Big Pine Key Fl. 33043 DISTANCE FROM HOMESTEAD ( Miami Dade ) to BAHIA HONDA : 1:57 hours by car. DISTANCE OF THE “BIG PINE KEY”: 10 minutes.

99 Don Quixote Key Big Pine Key, Big Pine Key
$649,000
3 Beds ⋅ 2 Baths ⋅ A12059984 MLS
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 Key
$5,390,000
3 Beds ⋅ 3 Baths ⋅ A11877495 MLS
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 Street, Big Pine Key
$3,899,000
A11960373 MLS
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 Drive, Big Pine Key
$3,899,000
A11960846 MLS
Welcome to The Barnacle Bed and Breakfast, a rare oceanfront offering in Big Pine Key where island living meetsincome opportunity. This beautifully updated waterfront property allows you to live the Florida Keys lifestyle whilehosting 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 anew roof, new windows, remodeled interiors, and upgraded throughout. Offered fully furnished, the estateincludes multiple structures with indoor and outdoor kitchens, central water, and electric service, allowing forimmediate 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 appreciatethe private beach, bay and ocean access, CBS dockage, private boat ramp, and on-site boat docking, making lifeon the water effortless. Currently operating as a bed and breakfast with strong daily rental performance, theproperty is now fully operational at capacity, presenting immediate income potential. Whether envisioned as aprivate waterfront retreat, an owner-operated B&B, or an investment opportunity, this is a truly unique chance toown a piece of paradise in the Florida Keys.

1557 Long Beach Drive, Big Pine Key
$3,899,000
6 Beds ⋅ 6 Baths ⋅ A11980368 MLS
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 Drive, Big Pine Key
$215,000
A12037782 MLS
Rare opportunity to own a piece of paradise in the heart of the Florida Keys. Located in the desirable Breezeswept Beach Estates community on Ramrod Key, this canal-front homesite offers the perfect blend of tranquility, natural beauty, and island living. The property benefits from a recorded Lot Line Adjustment that established the current buildable lot configuration, creating an excellent opportunity for future residential development. Survey and supporting documentation are available upon request.Imagine building your dream home just minutes from the open waters of the Gulf of Mexico and the Atlantic Ocean, with world-class boating, fishing, kayaking, paddleboarding, snorkeling, and diving right at your doorstep. Enjoy breathtaking sunrises, spectacular sunsets, and the relaxed lifestyle that has made the Florida Keys one of the most sought-after destinations in the world.Ramrod Key is known for its peaceful atmosphere, tropical surroundings, and convenient location, offering easy access to restaurants, marinas, shopping, and outdoor recreation while maintaining the privacy and charm of island living. Whether you are seeking a primary residence, vacation home, or investment property, this homesite presents a unique opportunity to create a custom waterfront retreat in one of the most desirable areas of the Lower Keys.Buyer to verify all building rights, permits, setbacks, utility availability, and development requirements with Monroe County.

27334 Saint Lucie Lane, Big Pine Key
$1,055,000
3 Beds ⋅ 3 Baths ⋅ A11977420 MLS
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 Lane, Big Pine Key
$1,150,000
4 Beds ⋅ 3 Baths ⋅ A12018191 MLS
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 Avenue, Big Pine Key
$750,000
3 Beds ⋅ 2 Baths ⋅ A11958850 MLS
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 Drive, Big Pine Key
$2,300,000
4 Beds ⋅ 3 Baths ⋅ A12036927 MLS
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 Boulevard, Big Pine Key
$2,700,000
4 Beds ⋅ 3 Baths ⋅ A11953691 MLS
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 Drive, Big Pine Key
$750,000
2 Beds ⋅ 2 Baths ⋅ A12015711 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 doorsStair access on both sides of the houseConforming enclosed space under the home with ample room for storage, hobbies, or recreational useGround-level garage and storage areaElectric driveway gate for added convenience and privacyLocated in the heart of the Lower Keys, this property offers easy access to boating, fishing, dining, and the relaxed island lifestyle that makes Big Pine Key so desirable.Don’t miss this rare canal-front opportunity offering privacy, space, breezes, and true Florida Keys living—schedule your private showing today!

251 Pelican Lane, Big Pine Key
$1,199,000
2 Beds ⋅ 2 Baths ⋅ A12012572 MLS
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 Avenue, Big Pine Key
$2,069,000
3 Beds ⋅ 2 Baths ⋅ A11916862 MLS
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 Drive, Big Pine Key
$895,000
A12037227 MLS
Build Immediately with Active Building & Pool Permits Included. This Bay Front/Gulf Front open-water lot offers 14,746 sq. ft. of waterfront opportunity with beautiful wide water views, sunrise exposure, and the rare advantage of moving forward without years of permitting uncertainty. Included are approved plans for an elevated CBS coastal residence featuring 4 bedrooms, 4.5 bathrooms, parking below, and a private in-ground pool. The planned home features an open-concept kitchen, dining, and living area, multiple bedroom suites, generous porch space, and a layout designed for relaxed indoor-outdoor Keys living. Enjoy open-water boating access to both the Atlantic Ocean and the Gulf of Mexico, along with nearby access to the backcountry for kayaking, paddleboarding, and exploring the surrounding waters. The Old Wooden Bridge boat ramp is less than 5 miles away, adding convenience for boating and water activities. Surrounded by the natural beauty of Big Pine Key, this area is well known for its Key Deer presence and peaceful coastal setting. A strong opportunity to create a custom Florida Keys waterfront retreat with the major approvals already in place.

30988 Witters Lane, Big Pine Key
$850,000
A11841689 MLS
Seller financing available, Commercial zoning, Tier 1 lot.

Us Highway 1, Big Pine Key
$840,000
2 Beds ⋅ 2 Baths ⋅ A12045192 MLS
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 Street, Big Pine Key
$660,000
3 Beds ⋅ 3 Baths ⋅ A11942155 MLS
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 Lane, Big Pine Key
$949,000
3 Beds ⋅ 2 Baths ⋅ B26013545 MLS
Bring your boats to this beautifully furnished canal front home. This home is secluded on a large corner lot with 190 ft. of concrete seawall. Large and open living, dining, and kitchen areas. Lovely updated kitchen and bathes. New beautiful floors, along with impact windows, doors, and metal roof. Enjoy swimming in the above ground pool, relaxing on the deck, cocktails at the bar, or meeting the adorable key deer roaming the neighborhood. Great yard with room for all your toys. Three vacant lots next door are county owned for preservation. Lots of privacy! This home is totally furnished with lots of extras. TURN KEY READY! Successfully rents for$9000 during season. This house is MAGICAL! ROOF 2017 AC 2019

1540 Lantana Lane, Big Pine Key