Welcome to 8705 County Road 99 in Headland a truly one-of-a-kind historic estate where timeless Southern charm meets rich local history. Situated on nearly 6 gated and fenced acres in the highly desirable Headland school district, this remarkable property offers privacy, character, and space unlike anything else on the market. Built in 1969 by a renowned pilot, this 3,528 sq ft architectural gem was uniquely designed so that its aerial footprint resembles an airplane, a rare and fascinating nod to its original owner's legacy. Inside, you'll find 4 bedrooms, 3 bathrooms, and the convenience of one-level living, all filled with historic character and generous living spaces designed for both everyday comfort and entertaining. Major updates provide peace of mind while preserving the home's charm, including new roof, windows, HVAC units (2018), plus septic tanks pumped/cleaned in 2026 and new front field lines installed in 2026. Step outside and experience the full beauty of the grounds featuring: A large restored two-story barn, an inviting sunroom, an elegant backyard fountain, a charming covered gazebo, and expansive fenced acreage ideal for recreation, animals, or simply enjoying the peaceful setting. This is more than a home, it's a piece of Wiregrass history offering the rare opportunity to own a truly distinctive estate with modern updates and unforgettable character.