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$1,500,000
Pineland SubDv.
Set within the historic heart of Pineland, this extraordinary 9.5-acre AG-2 zoned estate offers a rare opportunity to own a true piece of Old Florida heritage. Held within the same family for five generations, the property carries a legacy that stretches back more than a century, blending agricultural utility, historic character, and deep cultural significance into one irreplaceable offering. Surrounded by mature trees and peaceful rural landscapes, the property is currently configured with two established horse paddocks, stables, multiple outbuildings, and expansive usable acreage suited for equestrian, agricultural, recreational, or private estate use. The AG-2 zoning allows for flexibility while preserving the property’s timeless country setting. Positioned near the center of the property is a home originally constructed in 1926, now officially 100 years old. The residence remains occupied and functional, offering the next owner the option to restore and preserve a historic Pine Island homeplace or reimagine the property entirely according to their own vision. While the home itself is not considered the primary contributory value of the estate, it adds an unmistakable sense of authenticity and history rarely found in today’s market. What truly distinguishes this property is its location within one of the most historically significant areas in Southwest Florida. Located near the ancient Calusa Canal system and just moments from the renowned Pineland archaeological district, the property sits within a landscape once occupied and engineered by the powerful Calusa civilization — one of the most advanced indigenous societies in North America. These hand-built canals connected fisheries, inland waterways, ceremonial sites, and shell mound complexes throughout the region and remain among the most remarkable examples of prehistoric engineering in the United States. Historians recognize Pineland as one of the most important Calusa settlements ever discovered, historically associated with the settlement known as “Tanpa,” believed to have contributed to the modern namesake of Tampa. The nearby shell mounds, waterways, and preserved archaeological features stand today as enduring reminders of the area’s immense cultural importance. Whether envisioned as a private family compound, equestrian retreat, agricultural homestead, restoration project, or long-term legacy holding, this property offers a combination of acreage, history, and generational significance that is becoming increasingly impossible to find. Properties can be replicated. History cannot.

7535 Caloosa Drive, Bokeelia

$48,000
Kreamers Avocado Subd SubDv.
Discover the perfect place to build your dream island home on this beautiful private ½-acre lot in the heart of Bokeelia. Tucked away in a quiet, rural setting at the end of the street, this wooded parcel offers privacy, tranquility, and the laid-back island lifestyle Pine Island is known for. Located in an X flood zone, flood insurance is not typically required by lenders, adding even more value to this exceptional property. Enjoy easy access to everything that makes Bokeelia special. Just minutes from Pineland Marina, Four Winds Marina, public boat ramps, Alden Pines Golf Course (reopening Fall 2026), local fruit markets, shopping, and the famous Tarpon Lodge Restaurant. Spend your days boating to Pine Island Sound, Boca Grande Pass, Cayo Costa, Cabbage Key, and the Gulf of Mexico, where world-class fishing, shelling, and white sand beaches await. With no HOA restrictions, plenty of room for your custom home, tropical landscaping, and all your toys, the possibilities are endless. Whether you’re looking for a peaceful full-time residence, seasonal getaway, or investment opportunity, this property offers the perfect blend of natural beauty, privacy, and convenience. Come experience the true island lifestyle in beautiful Bokeelia!

6242 Fuller Drive, Bokeelia

$497,500
Pine Island SubDv.
SELLER FINANCING AVAILABLE!!! Your shortcut to island living starts here. Welcome to your private slice of paradise on Pine Island. Set on 2.5 acres, this property is already prepped and packed with opportunity the clearing and elevation is done, so you can skip the heavy lifting and jump straight into bringing your vision to life. Tucked away at the very end of a quiet dirt road, this peaceful setting is surrounded by other large parcels, offering both privacy and room to grow. A serene salt water pond borders the west side, adding a natural focal point and tranquil views. Zoned agricultural, this land is incredibly versatile design your dream homestead, start that boutique farm or nursery, or create a private retreat complete with a custom home, pool, and barn. With approximately 200 palm trees already on the ground included in the sale (standing palms do not convey), you’ve got a head start on landscaping or business potential. What truly sets this property apart are two brand-new wooden covered structures beautifully built and perfect for hosting gatherings, parties, family reunions, or even creating a unique event space. Whether you're entertaining under the island breeze or planning something bigger, the setup is already here. Utilities are already in place, with electric on site and a well. fed irrigation system covering the entire property ideal for maintaining lush greenery year round. Life on Pine Island is all about slowing down and soaking it in. Known for its laid-back charm, the island offers scenic bike paths, a local K–5 school, fresh-caught seafood, and endless kayaking opportunities. Surrounded by Gulf waters, you’ll also have access to some of the best shallow water fishing in the world. Whether you're looking to build, invest, or create something truly unique this property delivers the space, setting, and flexibility to make it happen.

12242 Eagles Nest Drive, Bokeelia

$44,900
Pine Island SubDv.
Calling all anglers, boaters, and lovers of the outdoors—this is your chance to claim your own slice of island living. Situated on **½ acre in unincorporated Bokeelia**, this property offers an incredible opportunity to build or invest in one of Southwest Florida’s most naturally beautiful and peaceful communities. Bokeelia is known for its quiet, laid-back lifestyle and abundant wildlife, offering a true escape while still being within reach of **Cape Coral, Fort Myers, and Punta Gorda**. Despite its secluded feel, you're just a short drive to airports, beaches, shopping, and dining. Take a drive out and experience it for yourself—you may find there’s no reason to leave the island once you arrive. Located at the northern tip of Pine Island, Bokeelia is surrounded by water, with easy access to **Pine Island Sound, Charlotte Harbor, and Matlacha Pass**—making it a dream location for boating and world-class fishing enthusiasts. Enjoy **southern exposure** and a setting filled with native palms and natural beauty. The lot will require some clearing, along with installation of a well and septic system, giving you the flexibility to design and build exactly what you envision. Let's go, what are you waiting for?

5599 Royal Okley Lane, Bokeelia

$1,350,000
Pine Island SubDv.
Prime opportunity in the heart of Bokeelia (Pine Island)!! This 4.78 Acre commercial parcel offers exceptional visibility and accessibility with over 300 ft. of frontage along Pine Island Rd. - one of the area's main thoroughfares. Zoned CC , CG, and CT , with a portion designated to TFC-2, this versatile property allows for a wide range of Commercial and mixed-use opportunities. Whether your looking to establish retail, office, service-oriented businesses, or a combination project, the zoning flexibility provides a strong foundation for your vision. Even better, Site plans have already been approved through Lee County for OPEN STORAGE BUSINESS , saving valuable time and expense-making this property truly SHOVEL--READY FOR DEVELOPMENT! DON'T MISS THIS RARE CHANCE TO SECURE A HIGH - VISIBILITY COMMERCIAL SITE IN A GROWING AREA. CALL TODAY FOR MORE INFORMATION !!

5361 Pine Island Road NW, Bokeelia

$925,000
Not Applicable SubDv.
One of the only few VACANT COMMERCIAL PROPERTIES left located on Pine Island, in Bokeelia. This prime location is only a 3 minute drive from the center of Pine Island. The ever growing island community has so much to offer and with this lot the possibilities are endless. The lot has some cleared areas throughout the property. This property has over 600+ feet of road frontage on Stringfellow Rd., which is the main road running from the south end of Pine Island to the north end. Also, in front of this property in-between the main road there is a bike path which gives peoples access to all of Pine Island right along Stringfellow. This property doesn't lack foot traffic either because Marina Dr. is another main road which leads to multiple communities throughout the inner north east side of Pine Island such as Blue Crab key, the 'Fish Streets' and Charlotte Shores.

11900 Stringfellow Road, Bokeelia

$95,000
Captains Cove SubDv.
CAPTAIN’S COVE — One of only two communities in Bokeelia offering a private boat ramp with direct water access! Prime Homesite in Bokeelia – Coastal Living at Its Finest Discover an exceptional opportunity to build your custom dream residence in the serene waterfront community of Bokeelia. This premium lot is ideally positioned just moments from the sparkling waters, offering a lifestyle defined by tranquility, nature, and coastal elegance. Surrounded by charming homes and lush tropical landscapes, this property provides the perfect canvas to create a private retreat or investment in one of Southwest Florida’s hidden gems. Experience breathtaking sunsets, island breezes, and the ultimate in relaxed luxury living. Build your dream home in beautiful Bokeelia. Steps from the water, peaceful vibes, and endless sunsets.

7883 Breakwater Court, Bokeelia

$37,000
Pine Island Center SubDv.
Discover the perfect investment opportunity at 5477 Avenue D, Bokeelia, FL 33922! This spacious duplex lot, measuring 100' x 100', offers endless possibilities in a prime location. Nestled in a charming community, you're just a short stroll from Pine Island Elementary School, making it ideal for families. Enjoy easy access to a wealth of amenities, including a community pool, scenic walking and bike paths, a library, museum, and popular pickleball courts. Indulge in local shopping and dining experiences, all within reach. Seize the chance to build your dream property or lucrative rental in this thriving area. Don't miss out on this incredible opportunity! THE PROPERTY NEXT DOOR AT 5465 AVENUE D IS ALSO FOR SALE MLS # 2026013788

5477 Avenue D, Bokeelia

$37,000
Pine Island Center SubDv.
Discover a prime opportunity in desirable Bokeelia with this cleared 100' x 100' duplex lot tucked away on a peaceful dead-end street. Perfectly positioned for convenience, this versatile property is just moments from the community pool, library, museum, pickleball courts, and local boat ramps, offering endless recreational possibilities. With nearby schools, shopping centers, and some of the area's best dining options, you'll enjoy a blend of tranquility and accessibility. Whether you're looking to invest or build your dream home, this lot presents an ideal canvas for your vision. Don't miss the chance to create your paradise in this charming island community! THE LOT NEXT DOOR IS ALSO FOR SALE 5477 AVENUE D MLS #2026013787

5465 Avenue D, Bokeelia

$175,000
Pine Island SubDv.
Build your dream home on this Gulf access homesite in Bokeelia, offering direct boating access to the surrounding waterways and the Gulf of Mexico. This single-family residential lot is ideally situated in a quiet area of Pine Island, providing a peaceful setting with natural surroundings and tropical landscape. Enjoy the convenience of launching your boat right from your future backyard and spending your days fishing, kayaking, or exploring nearby islands and waterfront destinations. The property provides ample space to design and build a custom home with room for outdoor living, a pool, and boat dock. Located just minutes from local marinas, boat ramps, waterfront restaurants, and island amenities, this lot offers the perfect balance of privacy and accessibility. Whether you’re looking to build a seasonal retreat or a full-time residence, this Gulf access property in Bokeelia presents a great opportunity to enjoy Southwest Florida boating and island living.

5350 Marina Drive, Bokeelia

$139,000
Knights Bokeelia Isle SubDv.
OPPORTUNITY KNOCKS: KNIGHTS BOKEELIA ISLE. RARELY AVAILABLE ON BEAUTIFUL BELLFLOWER STREET IN BOKEELIA, PINE ISLAND FLORIDA. WELCOME TO THIS OPPORTUNITY THAT IS PERFECTLY POSITIONED JUST YARDS FROM THE COMMUNITY BOAT RAMP/MARINA AND ONLY MINUTES FROM THE TAHITIAN VIBED BOKEELIA RIVIERA ON CHARLOTTE HARBOR. WITH LIFE AMONG THE NATURAL WONDERS AND AMENITIES OF THIS SPECIAL ISLAND COMMUNITY, YOU POSITION YOURSELF ON ACREAGE, YARDS FROM DEEP WATER. MOST PROPERTY RIGHT ON THE CANALS ARE LIMITED IN SIZE. HERE YOU HAVE OPTIONS TO DESIGN YOUR FAMILY’S LEGACY COMPOUND AND RETREAT TO THE GOOD LIFE.YOU CAN CREATE YOUR OWN MAGICAL, ENCHANTED FORREST AND TROPICAL GARDEN. ETC.. CITY WATER AND POWER AVAILABLE. IF YOU DIDN’T KNOW YOU WERE LOOKING FOR PINE ISLAND YOU’LL SOON KNOW… YOU ALWAYS WERE. 15855 BELLFOWER ST IS ALSO AVAILABLE.

15875 Bellflower Street, Bokeelia

$617,000
Kreamers Subd SubDv.
A rare opportunity to own coconut-grove acreage on Pine Island within a wellness-oriented farm setting designed for integrative and lifestyle-based living. This quiet tropical island environment is especially appealing to physicians and wellness practitioners seeking a warm-winter base that combines nature, purpose, and long-term land ownership. The property is rooted in organic agriculture, herbs, and land stewardship, offering a setting where food, lifestyle, and restorative living are central. In addition to personal seasonal use, owners may explore thoughtfully aligned income opportunities (such as agricultural leasing, eco-rental or cottage concepts, and practitioner or educational uses) where permitted and subject to recorded documents. Most comparable parcels in this offering were absorbed in early 2026, making this one of the final opportunities currently available. Pine Island is known for its slower pace, boating access, and proximity to Sanibel and Captiva, while remaining removed from high-density development. Sale is subject to recorded covenants, HOA/POA structure, easements/right-of-way, and an agricultural lease framework intended to preserve the integrity of the farm setting. Buyers are encouraged to review all documents with title and advisors to confirm intended use. Pine Island remains one of Southwest Florida's most supply-constrained land markets, with strict growth patterns, limited new subdivision activity, and a strong emphasis on agricultural and low-impact uses. This scarcity has historically supported long-term land value while attracting buyers who prioritize privacy, sustainability, and intentional living over dense development. As coastal pressure increases on nearby barrier islands and mainland communities, Pine Island continues to stand apart as a place where land ownership still carries intrinsic lifestyle and legacy value. The island's year-round warm climate, fertile soils, and strong agricultural heritage make it well suited for specialty farming, small-scale cultivation, and wellness-aligned land uses. Its proximity to Sanibel, Captiva, Fort Myers, and Southwest Florida International Airport allows owners to remain connected while enjoying a distinctly quieter environment. For buyers seeking Pine Island acreage with agricultural roots, wellness orientation, and long-term upside driven by scarcity rather than speculation, this parcel represents a compelling opportunity.

Lada Lane, Bokeelia

$90,000
Pine Island Shores Unit 6 SubDv.
Escape to Your Private 1-Acre Island Sanctuary in Bokeelia! Discover the "Old Florida" you’ve been dreaming of. This rare, oversized 1-acre lot offers the ultimate canvas for your secluded island retreat. Tucked away on a quiet, hard-packed sand road, this property provides the perfect balance of total privacy and convenient access to the best of Pine Island. Boaters and anglers, you are just minutes from multiple world-class boat launches. From here, the legendary tarpon fishing of Boca Grande and the pristine white sands of Cayo Costa and North Captiva are just a short boat ride away. Pine Island is a place where time slows down - there are no traffic lights, no high-rises, and no hustle. Instead, you’ll find vibrant art galleries, exotic mango groves, and a community that treasures its natural beauty and Calusa Indian heritage. Whether you are looking to build a stilt-home hideaway or a sustainable tropical homestead, this treed lot offers the space and serenity you won’t find in the city. No HOA fees, no frantic pace—just salt air, soaring eagles, and your own private piece of paradise. Come see why Bokeelia is Florida’s best-kept secret!

7224 Coccoloba Way, Bokeelia