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$1,850,000
2 Beds ⋅ 2 Baths ⋅ 617440 MLS
Open water pool home with breathtaking views of Bogie Channel and direct deep water access to both the Atlantic Ocean and the Gulf. Located on a spacious 13,275 sq ft lot, this solid concrete ground-level residence is a true boater's paradise featuring a 75-foot concrete dock and a protected boat basin. Inside, the 1,980 sq ft home offers a large great room, a Florida Room perfect for sunrise coffee, and a spacious kitchen with quartz countertops and a center island ideal for entertaining. Enjoy the seamless indoor-outdoor lifestyle with a waterfront pool surrounded by tropical landscaping, swaying palms, and a peaceful outdoor patio. The primary suite offers views of the pool and water, blending luxury and tranquility. Built to last with impact-resistant doors and windows and a durable metal roof. Additional features include a one-car garage, beautifully manicured grounds, and regular visits from native birds and Key Deer. Ride your bike across the bridge to No Name Key or walk to the world-famous No Name Pub. Just minutes to shopping, dining, and all the Lower Keys have to offer.

1607 Sunrise Dr, Big Pine
$763,000
4 Beds ⋅ 2 Baths ⋅ 618615 MLS
If you want a spacious home with plenty of privacy, this property delivers. Set within a lushly landscaped 12,500 sq. ft. double lot, the 2,136 sq. ft. living area provides ample space for family and guests with 4-bedrooms, 2-baths, a family room, laundry room and additional room that could be a 5th bedroom. Refreshing colors complement the space, and the tasteful furnishings are included with just a few exceptions. You can literally move in with only your suitcase! Central A/C cools and heats the majority of the home, and mini-split units cover the rest. Flooring consists of solid bamboo and tile throughout. The fenced back yard features a tiki hut for entertaining and relaxing. The property is bordered on two sides by county and state-owned protected lands, adding to the privacy. The detached garage is a bonus!

30374 Oleander Blvd, Big Pine
$1,121,665
3 Beds ⋅ 3 Baths ⋅ 618357 MLS
Wake up to endless water views and wind down with breathtaking Keys sunsets at this peaceful island retreat. Set on a quiet corner lot, this 3-bedroom, 3-bath home offers the perfect blend of privacy, comfort, and classic Keys charm. A wraparound screened in porch with six sets of sliding glass doors fills the home with natural light and cooling tropical breezes, while rich pecky cypress accents add warmth and character throughout. Across the street, a community park provides a serene green space, and for boaters, the location is ideal—just minutes to Pine Channel, about 20 minutes by boat to the Content Keys, and easy access to the Atlantic. Outdoor living shines with a spacious screened patio, a 10' x 10' tiki hut for entertaining, and a 10,000-lb boat lift ready for your next adventure. Located in the highly sought-after Port Pine Heights neighborhood, this exceptionally tranquil community is known for its natural beauty and frequent visits from Key deer. With a residents-only park just around the corner and some of the most peaceful surroundings in the Lower Keys, this is more than a home—it's the island lifestyle you've been dreaming of.

3759 Seagrape St, Big Pine
$3,100,000
9 Baths ⋅ 617662 MLS
Prime commercial property just 30 minutes from Key West, located in the heart of Big Pine Key. This rare offering includes 35,475 sq. ft. of commercial land with 215 feet of high-visibility frontage along the iconic Overseas Highway (U.S. 1) — the only road connecting the islands of the Florida Keys. Positioned near the island's only traffic light, across from CVS, Walgreens, and Ace Hardware, while next door to NAPA. The site benefits from exceptional exposure and steady high-volume traffic. Key Features: One building is 2,700 square feet and the other 2,550 square feet, totaling 5,250 square feet of retail space indoors occupied by 9 tenants, two of which have been at this location for over 15 years, and several others for over 5 years. There are two additional tenants renting yard space, one is within the 4,500 square-foot fenced enclosure and the other is the ice machine which has been at this location for close to 15 years. There is also a 200' radio tower located on the property with potential for added future revenue. Both buildings are elevated and equipped with a handicap-accessible ramp that services all retail spaces. Each structure is constructed from solid concrete, incorporates several firewalls between tenants, and features a premium, robust roofing system that includes steel trusses, a lightweight concrete deck, and a hot-mopped 90-pound slate finish—providing exceptional structural strength, fire resistance, superior water protection, and long-lasting durability in demanding environments. Whether you're looking to grow your portfolio, expand an existing business, or launch a new venture, this high-visibility, high-traffic property offers limitless potential. Don't miss this rare investment opportunity in the Florida Keys!

30330 30348 Overseas Hwy, Big Pine
$850,000
615821 MLS
Commercial Zoning Tier 1 Wooded lot

Overseas Overseas N Us Highway 1, Big Pine
$825,000
3 Beds ⋅ 2 Baths ⋅ 617747 MLS
Back on the market! Welcome to this meticulously maintained and updated move-in ready canal-front home that offers the perfect blend of comfort, style, and durability. Featuring an inviting open-concept floor plan, this home boasts three spacious bedrooms and two modern bathrooms, all enhanced by LVP flooring throughout. Built above flood level with just the right number of steps to climb, this home ensures both convenience and peace of mind. The freshly painted exterior showcases durable James Hardie siding, complemented by brand-new impact windows and doors. Topped with a sturdy 5V crimp metal roof, this property is designed to withstand the elements. Situated on an expansive 7,500 square foot lot, this waterfront gem offers 75 feet of concrete dock and seawall, providing ample space for docking your boat or simply enjoying serene canal views. Launch your boat at the nearby and convenient community boat ramp. Whether you're seeking a relaxing retreat or a full-time residence, this thoughtfully upgraded home is ready for you to move in and start enjoying the coastal Keys lifestyle. INSURANCES: Flood = $2,428 Wind = $4,467 Homeowners = $702.48

29115 Rose Dr, Big Pine
$2,150,000
3 Beds ⋅ 3 Baths ⋅ 617619 MLS
Discover the easygoing charm of the Lower Keys at this .81-acre waterfront estate, featuring a two-bedroom, two-bath main house and a one-bedroom, one-bath guest cottage with views over Bogie Channel. Enjoy leisurely days entertaining under the large poolside tiki hut or on the covered platform at the end of the 463-foot pier—perfect for relaxing with family and friends while watching sunsets after a fun day on the water. The platform is equipped with a boat lift, floating jet ski dock, and an outdoor kitchen. The completely renovated, two-story CBS main home offers a spacious 1,950 sq. ft. living area with enough space to possibly add a third bedroom if needed. Large impact-resistant windows allow for views of peaceful sunrises and moonrises over the property and open water. The updated 536 sq. ft. frame-stucco guest cottage gives visitors their own comfortable retreat. Thoughtfully planned lighting enhances the 35,330 sq. ft. fenced property. Monroe County's small Palm Villa Park borders the southern edge, and the County owns the land directly across the street to the north, intended to remain undeveloped. Move-in ready and tastefully furnished, this tranquil slice of paradise is just minutes from local shops and restaurants, and only 30 miles from lively Key West. (Note: Living Area Sq. Ft. Source is the Property Record Card.)

30468 Oleander Blvd, Big Pine
$499,000
614178 MLS
Prime Commercial Fishing Property in the Florida Keys! Discover a rare opportunity to own and operate a commercial fishing business in the coveted Commercial Fishing Special District of Big Pine, FL. This unique zoning allows unparalleled access to open water, making it a fisherman's paradise. Here are the highlights: - Buildable Property: Your vision can come to life with ease on this buildable lot. - AE Flood Zone: Favorable flood zone location for peace of mind. - Endangered Species Free: Not restricted by endangered species listings. - Commercial Vessel Accommodation: Control depth tailored to fit commercial fishing vessels. - Large Corner Lot: Expansive nearly 1/2 acre lot, offering ample space. - Bayside Location: Situated in Big Pine on the tranquil Bayside, with quick access to the water. This property represents a rare and valuable investment opportunity with its unique zoning, generous lot size, and prime location. It stands out as one of the few remaining parcels that cater specifically to the commercial fishing industry. Act now to secure this sophisticated and financially advantageous piece of real estate in the beautiful Florida Keys! Contact us today for more information or to schedule a viewing. Don't miss out on this exclusive chance to elevate your business!

Vacant Lot Vacant, Big Pine
$2,700,000
3 Beds ⋅ 3 Baths ⋅ 618316 MLS
Walk into this luxurious palace with captivating open water views. Light colors accenting the beautiful interior with matching large porcelain floors 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. Three 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
$2,300,000
4 Beds ⋅ 3 Baths ⋅ 614697 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, durable metal roof, stainless steel appliances, quartz countertops, open-concept living areas, screened porch, private in-ground pool, and covered parking below. Built with modern coastal construction in mind, the CBS structure, impact openings, elevated design, and metal roof provide lasting durability, low-maintenance appeal, and insurance-friendly features for coastal living. The waterfront setting is enhanced by allocated dockage with an approximately 45' access walk leading to a 91' platform, creating a great setup for enjoying boating, kayaking, paddleboarding, and the surrounding water views. Situated on a generous 14,680-square-foot lot with approximately 75' of waterfront frontage, the property captures panoramic Bay/Gulf-front water views and beautiful sunrise exposure. Enjoy boating access via Bogie Channel, with easy access to the backcountry and fast open-water routes to both the Atlantic Ocean and the Gulf. Nearby Looe Key Reef is a favorite destination for snorkeling and scuba diving, with excellent fishing opportunities nearby. Located on the Big Pine Key side of the Bogie Channel Bridge to No Name Key, this setting offers peaceful water views and a unique sense of island privacy. The property can be used as an investment property for vacation rental use, adding flexibility and income appeal. Located near the iconic No Name Pub and surrounded by the natural beauty of Big Pine Key, where Key Deer are a beloved and frequent part of everyday island life. Unlike smaller, more remote keys, Big Pine Key serves as a convenient Lower Keys hub with everyday necessities nearby while still offering the quiet waterfront lifestyle people come to the Keys to enjoy. Construction is complete and ready for immediate occupancy.

30995 Watson Blvd, Big Pine
$849,000
2 Beds ⋅ 2 Baths ⋅ 618629 MLS
GREAT INVESTMENT OPPORTUNITY! $849,000 Best price property in Pine Channel Estates, Big Pine Key. Fully furnished. Remodeled 2 bdrm/2 full bath + BONUS room (3rd bdrm/office). 75' Canal frontage. Total sq.ft. 1934 w/heated sq.ft. 1277. All new SS appliances. Metal roof, impact windows and garage door, vinyl siding, tankless water heater, gutters, hurricane shutters, fence, covered patio, large garage and RV/Generator hookups. Low Insurance costs. Generous and impressive one level living space is perfect for entertaining and family gatherings. Located in a sought-after subdivision highlighting deep, quick open water access to the ocean and back country for stellar world class fishing, lobstering, diving and snorkeling. Loads of parking. Bike to the nature park, shops, restaurants, water sports, groceries and pharmacy. Take a short boat ride to KiKi's for a delicious meal and live music. 30 minutes to Key West! This property is elevated and ideal as a primary, second or investment. Use your creativity when enhancing your island style to the vast outdoor canvas with a pool/tiki hut. Just 30 mins to Key West! Own your slice of paradise in the Florida Keys today!

29544 Independence Ave, Big Pine
$1,295,000
4 Beds ⋅ 2 Baths ⋅ 617564 MLS
Discover an outstanding opportunity in Big Pine Key with this canal-front, stilted duplex featuring two spacious 2 bedroom 1 bath residences and deep-water boating access. This is an exceptional boater's duplex in Pine Channel Estates where you can enjoy income and lifestyle in one place. Enjoy 75 feet of concrete dockage with a convenient step-down and retaining wall, all situated on a clean, wide canal that delivers you to the ocean or the bay within minutes. Recent upgrades include a brand-new metal roof for peace of mind. One unit has been beautifully updated with modern finishes, while the second unit is rented annually—ideal for buyers looking to live in one home and generate immediate income from the other. Solid construction, excellent water quality, and a prime location in one of the most desirable boating neighborhoods in the Lower Keys make this property truly stand out. Come see for yourself!

29678 Enterprise Ave, Big Pine
$2,900,000
3 Beds ⋅ 4 Baths ⋅ 618739 MLS
Spectacular Open-Water Retreat with Unmatched Sunset View This exceptional open-water property offers breathtaking western-facing sunset views and premier ocean access with no bridges--perfect for boating enthusiasts. Enjoy privacy and natural beauty bordering the Florida Key Deer Preserve. The property features over 200 feet of concrete seawall, a 35' x 15' boat basin making it ideal for waterfront living. Step inside this impressive concrete-built home, where water views surround the main living area. The spacious living room showcases vaulted wood ceilings and abundant natural light. The home offers three en-suite bedrooms, plus an additional full bath conveniently located off the kitchen. Designed for true Florida Keys living, the resort-style in-ground pool and tiki hut are perfectly positioned to take in the spectacular western sunset views, creating an unforgettable setting for relaxing evenings and waterfront entertaining. Additional highlights include: Impact windows and slidersLarge attached garage Separate utility/storage building Exceptional privacy Direct ocean access This is a rare opportunity to own a private, west-facing luxury estate that seamlessly blends modern construction, boating convenience, and breathtaking sunset views.

29581 Richard Rd, Big Pine
$2,499,000
3 Beds ⋅ 2 Baths ⋅ 618401 MLS
Tucked away on 2 gated acres along the pristine waters of Bogie Channel, Dei Paradiso is a one-of-a-kind open water estate offering total privacy, resort-style amenities, and world-class boating access to both the ocean and backcountry. Just a mile off the Overseas Highway, peace and convenience converge in this tropical retreat. Awaken to dazzling sunrises and wind down beneath the glow of moonrises over the channel, all from your expansive 1,500 sq. ft. saltwater pool, wrapped in swaying palms and endless sea views. Inside, the open-concept living space connects effortlessly to the outdoors, with floor-to-ceiling glass bringing the water right to your doorstep. The heart of the home is a chef's kitchen built to impress: quartz counters, a six-burner gas stove, four ovens, stainless steel appliances, and a massive island with seating for eight — ideal for gatherings and memory-making. Outdoor features abound: a private sandy beach, multiple dining and lounging areas, a 50-foot RV pad with 30/50 amp service overlooking the water, and a 40x40 four-bay garage for your boat, cars, and toys. A dock permit is in progress, opening up quick access to prime fishing grounds and sandbars. Surrounded by flowering tropical plants and a bounty of fruit trees, including Hayden mangoes, Catalina avocados, and Key lime hedges, this home is as nourishing as it is beautiful. Built like a fortress, Dei Paradiso features poured concrete construction, CBS walls, hurricane windows/shutters, prestressed beams, and a standing seam aluminum roof. Elevated for peace of mind with living spaces over 15' above sea level. A rare and radiant offering in the Florida Keys. Dei Paradiso isn't just a home...it's a legacy.

1233 Ave A, Big Pine
$120,000
617719 MLS
Positioned just off US-1 (Jimmy Buffett Memorial Highway), this parcel of land benefits from excellent visibility and accessibility, supporting a wide variety of potential commercial uses. Potential for securing valuable ROGO points for future permitting needs in Monroe County (buyer to verify the number of ROGO points with the County).

Lot 6 Vacant Land, Big Pine
$54,000
618082 MLS
ROGO lot worth 2 points for DEDICATION purposes. Seller has county ROGO Letter of Land Dedication verifying lot is eligible for land dedication/2 points. Want to build quicker? This is a path. Buyer to verify points and process with Monroe County. See Documents tab for letter.

Bk 4 Lt 9 Pine Crest Road, Big Pine
$699,000
4 Beds ⋅ 3 Baths ⋅ 616469 MLS
699,000 for 2 units. Great price reduction on income producing CBS duplex in Big Pine Key. Good boating with direct access to Bogie Channel. Large lot with full seawall. Interior is cute and tidy and would be easy to rent or live in one side and generate extra income. Fully furnished. insurance ESTIMATE with owner occupied on 1 unit: 1410 Homeowners, Flood 4000.00 windstorm 8530.00.

1433 Sunset Rd, Big Pine
$1,800,000
3 Beds ⋅ 2 Baths ⋅ 618850 MLS
This beautifully maintained 3-bedroom, 2-bath concrete block home truly has it all. Designed for comfort and peace of mind, the property features impact windows and sliders throughout. Step inside to a spacious living room that flows seamlessly into the dining area, where triple sliding glass doors open to a screened patio--perfect for enjoying the coastal breeze and tranquil water views. The kitchen offers stainless steel appliances and granite countertops, offering both style and functionality for everyday living or entertaining. Offered fully furnished--including kayaks--this home is truly move-in ready, allowing you to start enjoying the waterfront lifestyle from day one. Boaters will appreciate the 12,000 lb boat lift and excellent access--just minutes to Pine Channel and open water--making it easy to spend the day fishing, diving, or cruising the turquoise waters of the Florida Keys. Set along a peaceful canal with serene salt pond views, this waterfront retreat offers privacy, island charm, and direct boating access right from your backyard. Whether you're searching for a full-time residence or a relaxing coastal escape, this home delivers the true Keys lifestyle.

29549 Forrestal Ave, Big Pine