A rare piece of Charleston history, this extraordinary deepwater estate occupies a commanding high bluff overlooking Charleston Harbor, offering sweeping water views, exceptional boating access, and a remarkable connection to the Lowcountry's past. Set on nearly an acre in the heart of the Old Village of Mount Pleasant, the property is believed to be among the area's earliest surviving homes, offering an extraordinary blend of historic architectural integrity, timeless craftsmanship, and beautifully renovated living spaces.Rich in local history, the property is situated on Haddrell's Point, a historic settlement that supported a ferry operation from the mid-1700s through the mid-1800s. Local historical accounts also associate these shores with George Washington's visit to Charlestonin the 18th century. The residence retains an exceptional collection of period details, including hand-hewn structural timbers, distinctive dragon-beam bracing, remarkably wide 9- to 13-inch mill-sawn floors, and expansive cypress paneling--a rare testament to the craftsmanship of an earlier era. Throughout the fully renovated main residence, historic character is complemented by modern comfort, with soaring ceilings, beautiful moldings, and seven working fireplaces creating an atmosphere that is both gracious and inviting. Full-length double porches frame breathtaking harbor views, while a covered ground-level loggia provides a natural transition to the infinity pool and outdoor entertaining spaces. The main living level is designed for both comfortable everyday living and exceptional entertaining, with a beautifully appointed kitchen, dining area, inviting living room, and elegant bar. The second floor features a spacious primary suite with a generous closet and well-appointed bath, along with a second bedroom offering its own ensuite bath and oversized closet. Two additional guest bedrooms on the top floor share a full hall bath. The parterre of the home is in an X flood zone not requiring flood insurance and offers remarkable flexibility, with an expansive living area anchored by a beautiful masonry fireplace, a second kitchen, and a dedicated office or flex space, all opening directly to the covered loggia, pool house, and pool area which cascades to the dock. This area can easily function as a separate au pair or mother-in-law arrangement. Beyond the main residence, the property includes a fully renovated guest house situated above the three-car garage. Thoughtfully arranged with an open-concept layout, the space features a kitchenette, living area, and sleeping quarters. An additional single-car garage provides even more storage and flexibility. The separate pool house offers further versatility for guests and outdoor entertainment. The outdoor setting is every bit as impressive as the interiors. A stunning new pool and pool house, beautifully executed with a park-like setting. This work was completed in 2025 to create a private waterfront oasis. The deepwater dock is equipped with railings on both sides and two new power lifts installed in 2023, offering exceptional access to Charleston Harbor and beyond. Significant capital improvements include a new copper roof, gutters, and downspouts on the main residence and pool house in 2022; new HVAC systems and built-in dehumidifiers throughout all floors of the main residence in 2022; all new windows throughout the property (2025); and new lightning protection on the main house and guest house in 2023. With extraordinary harbor views stretching along the Old Village waterfront toward Fort Sumter and the tip of Sullivan's Island as well as the Charleston coastline, 111 Live Oak Drive is an exceptionally rare offering. Combining a storied past, remarkable architectural details, extensive modern renovations, and premier deepwater amenities, this is a truly distinctive opportunity to experience the very best of historic Old Village and Lowcountry waterfront living, just minutes from downtown Charleston and the area's best beaches.