Big Pine Key FL Homes For Sale

2 Beds ⋅ 2 Baths ⋅ A12113308 MLS ⋅ Eden Pines BLDG.

This beautifully updated 2 bedroom, 2 bathroom home sits on an oversized lot and offers the perfect blend of comfort, style, and waterfront living. Enjoy a renovated kitchen and bathrooms, a relaxing screened in porch, and a fenced yard featuring a sparkling fiberglass pool. Boating enthusiasts will appreciate the 75 ft of concrete seawall and 15,000 pound boat lift, providing convenient access to the water. A garage adds extra convenience and storage. Whether you're entertaining guests, enjoying a peaceful day by the pool, or heading out on the boat, this property offers the ideal Keys Lifestyle!

1669 Lantana Lane, Big Pine Key

$799,000

A12113271 MLS

This property offers an established commercial presence along the U.S. 1, with a valuable development history documented by Monroe County Planning & Environmental Resources. The subject property consists of (4Lots) totaling approximately 20,000 square feet, according to Monroe County GIS. All parcels are located within the Suburban Commercial (SC) Land Use/Zoning District and carry a Mixed Use/Commercial (MC) Future Land Use Map designation, providing an attractive opportunity for an investor, business owner, or developer looking for a commercial property in the Lower Florida Keys. Monroe County determined that 3,845 square feet of nonresidential floor area at 31095 Avenue A and 1,052.64 square feet at 31096 Avenue B were lawfully established as of September 19, 2001 and are exempt from the NROGO permit allocation system--a combined total of approximately 4,897.64 square feet of recognized nonresidential floor area. County permit records document uses at 31095 Avenue A over the years including a laundry, store, sandwich shop, real estate office, restaurant and other commercial uses, while records for 31096 Avenue B identify the building as an office building dating back to at least 1980. The property's location, commercial zoning, established development history and documented NROGO-exempt floor area create an exciting opportunity to reimagine, redevelop or reposition this Big Pine Key commercial site, subject to Monroe County's current development regulations and approvals.

31095 Avenue A, Big Pine Key

$895,000

A12112073 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

$2,300,000

4 Beds ⋅ 3 Baths ⋅ A12111941 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. 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

$2,450,000

3 Beds ⋅ 4 Baths ⋅ A12099164 MLS

Welcome to an exquisite open-water retreat in Big Pine Key, an unparalleled blend of modern luxury and authentic Keys lifestyle. This completely updated and remodeled 3BD/4BA pool home offers panoramic water views from every angle, setting the stage for endless sunrises, sunsets, and starry nights. Designed with sophistication and comfort in mind, each bedroom is an ensuite, ensuring privacy and convenience for family and guests. Beyond its beauty, this property is one of the rare few in Monroe County allowing nightly vacation rentals, boasting a highly successful rental history for those seeking both personal enjoyment and income opportunity. Every detail has been thoughtfully curated, impact windows and doors, corian countertops and two on-demand water heaters reflect quality and peace of mind. The boating enthusiast will appreciate one of the few marked channel systems leading directly to the Gulf of Mexico with the Atlantic Ocean just minutes away. Utilize the 220 sq ft extended dock for your vessel to some the best fishing, diving and boating in the continental U.S. Whether lounging poolside, entertaining on the spacious decks or heading out on the water this property offers an unmatched Keys experience. Rare, refined and ready for your investment this is open-water living at its finest.

31473 Warner Street, Big Pine Key

$995,000

2 Beds ⋅ 2 Baths ⋅ A12094986 MLS ⋅ Eden Pines Colony BLDG.

Beautifully maintained CBS home in the desirable Eden Pines Colony, custom-built by well-known builder Art Fuchs. Situated on a 7,625 SF corner lot with approximately 195 feet of canal frontage, the property is surrounded by a 45-foot-wide canal to the east and a 50-foot-wide canal to the south. The waterfront features a concrete seawall, two step-down docks, davits, and a convenient fish-cleaning table, with excellent access to both the ocean and backcountry. The 1,092 SF home offers a comfortable split-bedroom layout, tile flooring throughout, a spacious kitchen, and a screened porch with access from both the living room and primary bedroom. The ground level includes a 480 SF garage, covered parking and sitting area, plus an additional 192 SF storage area. Additional features include a metal roof, accordion shutters, and panel shutters for the sliding glass doors. The property is surrounded by mature coconut palms, slash pines, and a good-sized mango tree, making the outdoor space easy to maintain. Furnishings will remain for the seller's convenience. No HOA. A great opportunity to own a well-maintained canal-front home in Big Pine Key and make it your own.

1539 Lantana Lane, Big Pine Key

$379,900

A12092777 MLS

Excellent neighborhood! Cleared land surrounding $800,000 homes plus range. In Rogo, Tier II . All homes are required to be CBS and no modular homes allowed. Plans for a 3 bedroom 2 bath home have been approved (county permits alterations to the house plans before you build, enabling you to design to your own specific needs). PERMIT Number is 16103833. Annual low association of 150.00. Dock plans underway. No living a board permitted. Water, Sewer and Electric are available ready to be connected.

30351 Flamingo Lane, Big Pine Key

$1,750,000

4 Beds ⋅ 3 Baths ⋅ A12082823 MLS

Exclusive New Construction in Big Pine Key, Florida Discover the perfect blend of modern luxury, coastal living, and exclusive design in this stunning newly constructed home in Big Pine Key, Florida. Featuring 4 spacious bedrooms and 3 beautifully designed bathrooms, this exceptional residence offers a sophisticated open-concept interior with high-end finishes, contemporary details, and an elegant design created for comfort and style. Step outside to an expansive terrace where you can relax, entertain, and enjoy breathtaking ocean and canal views. The property also features a private boat lift, providing direct and convenient access to the water--perfect for boating and enjoying the incredible Florida Keys lifestyle. Situated on an approximately 9,000-square-foot lot, this property offers generous outdoor space and privacy while embracing the natural beauty of the Keys. Every detail has been thoughtfully designed to create a unique and exclusive living experience. Whether you're looking for a luxurious primary residence, a private Keys retreat, or an exceptional investment opportunity, this one-of-a-kind Big Pine Key home offers the perfect combination of modern architecture, waterfront living, and the unmistakable charm of the Florida Keys.

31450 Avenue G, Big Pine Key

$950,000

3 Beds ⋅ 3 Baths ⋅ A12082023 MLS

Brand-New Waterfront Home in the Florida Keys Discover the ultimate Florida Keys lifestyle in this stunning brand-new construction, perfectly designed for those who love boating, waterfront living, and the beauty of the Gulf. This exceptional property features 3 spacious bedrooms, 2.5 bathrooms, and a private boat dock, providing direct access to the Gulf for unforgettable days on the water. The home offers generous parking space and is being sold fully furnished, allowing you to move in and immediately enjoy everything the Keys have to offer. From the modern finishes and comfortable living spaces to the incredible waterfront setting, every detail was designed for relaxation and enjoyment. Step outside and enjoy your own private waterfront paradise, with your boat just steps from your door and direct access to the Gulf. Whether you're looking for a luxurious primary residence, a vacation retreat, or an exceptional investment opportunity, this property offers the perfect combination of new construction, boating access, comfort, and the laid-back Florida Keys lifestyle. Your dream home on the water is ready to welcome you home.

31490 Avenue F, Big Pine Key

$975,000

3 Beds ⋅ 2 Baths ⋅ A12082035 MLS

Brand-New Waterfront Home in the Florida Keys Discover the perfect blend of modern luxury and relaxed island living in this stunning brand-new construction home in the Florida Keys. Boasting beautiful canal views, this exceptional property offers the ideal setting to enjoy the tropical lifestyle the Keys are famous for. The home features 4 spacious bedrooms and 3 beautifully appointed bathrooms, providing plenty of room for family, guests, or entertaining. The open and inviting layout is designed to maximize natural light and create seamless connections between the indoor and outdoor living spaces. Enjoy peaceful mornings overlooking the canal and breathtaking sunsets in your own private paradise. With its modern construction, spacious living areas, and desirable waterfront setting, this home is an excellent opportunity for anyone looking to experience the Florida Keys lifestyle in a brand-new residence. Modern design. Spacious living. Waterfront views. Your Florida Keys dream starts here.

31441 Avenue F, Big Pine Key

$189,000

A12072388 MLS

Enjoy the Florida Keys lifestyle with this RV lot offering access to a variety of community amenities, including a swimming pool, clubhouse, shuffleboard, picnic and grilling areas, laundry facilities, and bathhouse.A convenient bike path located directly in front of the park provides easy access to nearby shopping and restaurants. For boating enthusiasts, boat storage is available across the street, with a boat ramp conveniently located nearby.The affordable $197 monthly fee includes water, sewer, cable, and Wi-Fi, making this a great opportunity for a Keys getaway, seasonal retreat, or recreational home base. Identical lot #20 also for sale*Short term rentals are allowed*

29859 Overseas Highway, Big Pine Key

$189,000

A12072379 MLS

Enjoy the Florida Keys lifestyle with this RV lot offering access to a variety of community amenities, including a swimming pool, clubhouse, shuffleboard, picnic and grilling areas, laundry facilities, and bathhouse.A convenient bike path located directly in front of the park provides easy access to nearby shopping and restaurants. For boating enthusiasts, boat storage is available across the street, with a boat ramp conveniently located nearby.The affordable $197 monthly fee includes water, sewer, cable, and Wi-Fi, making this a great opportunity for a Keys getaway, seasonal retreat, or recreational home base. Identical lot #21 also for sale. *Short term rentals are allowed*

29859 Overseas Highway, Big Pine Key

$5,200,000

8 Beds ⋅ 6 Baths ⋅ A12075674 MLS

Coastal living awaits at this spacious property in Long Beach Estates on Big Pine Key! Offering exceptional privacy and direct access to island life, this lot features ample space for your island sanctuary. Located just minutes from pristine beaches, local dining, open water boating, and the Bahia Honda State Park. Perfectly situated in the heart of the Lower Keys, offering quiet, relaxed island living with easy access to Key West.

1557 Long Beach Drive, Big Pine Key

99 Don Quixote Key Big Pine Key, Big Pine Key

$1,500,000

A12060300 MLS

OPPORTUNITY PRICEConstruction of DETACHED DWELLING UNITS is permitted on the island under the OS (Offshore Island) land-use district designation. The island also complies with Monroe County density and open space requirements as outlined in Article III, Section 130:90 (Offshore Island District – Land Use).There is no other 22-acre island in the Florida Keys with approved building status available at this price point of $1,200,000—a price reduced due to family medical circumstances.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

$4,650,000

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

$178,000

A12037782 MLS

Rare opportunity to own a canal-front property in the desirable Breezeswept Beach Estates community on Ramrod Key. Please note that the property currently has an unresolved issue involving the lot-line adjustment and the configuration of the parcel. The buyer will be responsible for investigating, resolving, and assuming all costs associated with this matter after closing. The asking price has been reduced to reflect this condition.Survey and available supporting documentation will be provided upon request. Buyer must independently verify the property’s legal lot configuration, building rights, permits, setbacks, utilities, zoning, and all applicable development requirements directly with Monroe County and other appropriate authorities. The property is being sold in its current condition, and no representation or guarantee is made regarding buildability or the outcome of the lot-line adjustment matter.Located minutes from the waters of the Gulf of Mexico and the Atlantic Ocean, the property offers convenient access to boating, fishing, kayaking, snorkeling, diving, restaurants, marinas, shopping, and the relaxed lifestyle of the Lower Florida Keys.

27334 Saint Lucie Lane, Big Pine Key

$1,100,000

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 rooms downstairs. Home is fully furnished and ready to use. Seller Financing.

29565 Flying Cloud Avenue, Big Pine Key

$699,000

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

$964,999

3 Beds ⋅ 2 Baths ⋅ A11962087 MLS

Welcome to island living in Big Pine Key. Situated on a desirable corner lot, this beautifully remodeled 3-bedroom, 2-bathroom home offers 70 feet of dockage with davits, providing excellent boating access and true waterfront Keys living. The home has been fully updated, featuring a newer roof, updated windows, modern flooring, renovated kitchen and bathrooms, and upgraded lighting throughout. The property also features a large garage and ample storage space, ideal for boating gear, tools, or recreational equipment. Enjoy privacy, outdoor living, and easy access to open water, nearby parks, and local amenities. A fantastic opportunity for a full-time residence, vacation retreat, or investment property in the Lower Keys.

30368 Killdeer Lane, Big Pine Key

$1,970,000

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

$200,000

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

$680,000

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

$899,000

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 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 ELAVATION CERTIFICATE AVAILABLE IN DOCUMENTS

1540 Lantana Lane, Big Pine Key

Big Pine Key FL Homes For Sale

Big Pine Key FL Homes For Sale

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