Pineland Real Estate

Welcome to Pineland, a hidden gem nestled in the picturesque Bokeelia, Lee County, Florida. This charming community is the perfect blend of tranquil living and natural beauty, offering residents a unique opportunity to embrace the serene lifestyle that Southwest Florida is renowned for.

Pineland is characterized by its lush landscapes, stunning waterfront views, and a strong sense of community. Surrounded by the pristine waters of Pine Island Sound, this development provides easy access to some of the best fishing, boating, and outdoor activities that Florida has to offer. Whether you're an avid angler or simply enjoy a leisurely kayak ride, the natural beauty of the area is sure to captivate you.

The development features a variety of thoughtfully designed homes that cater to diverse lifestyles, from cozy single-family residences to spacious waterfront properties. Each home is crafted with quality materials and modern amenities, ensuring comfort and convenience for every resident. The community is also surrounded by charming local shops, delightful restaurants, and vibrant farmer's markets that showcase the best of Florida's local produce.

Pineland is not just about beautiful homes; it’s about fostering connections and creating memories. With a welcoming atmosphere and friendly neighbors, residents can enjoy a sense of belonging in this idyllic setting.

Come discover Pineland, where the beauty of nature meets the warmth of community living. Your dream home awaits in this enchanting corner of Bokeelia, Florida!

Newest Listings in Pineland

$1,279,000

2026023455 MLS

A rare opportunity to own a 60’ x 100’ reinforced concrete barn topped with a durable metal roof, thoughtfully positioned on a gorgeous 4 acre parcel. This exceptionally landscaped estate blending tropical Florida beauty with classic Old Florida charm. Surrounded by mature pine trees and native palmettos, the property offers both privacy and natural elegance. Built for strength and longevity, this structure is designed to withstand severe weather conditions and sits comfortably above the flood plain, providing peace of mind and security. This property has had a well plus irrigation installed, vegetation clean up, loads of fill dirt brought in, 2 culverts installed. All landscaping work has been done professionally with very low maintenance plants and trees. Build your dream home in the heart of Bokeelia, Pineland is one of the most desirable neighborhoods on Pine Island and has a lot of amenities to offer including the historical Calusa Indian mound preserve(Randell Research Center) right around the corner from the post office, Alden Pines Golf Course, Safe Harbor Marina, which has ferries to the outer islands, and of course the Tarpon Lodge. This property also has the option to have a road access from the north side from Capri Ln but is overgrown currently.

6690 Pineland Road, Bokeelia

$1,500,000

2026022571 MLS

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

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