Positioned on one of the most prominent sites on Sullivan's Island, 1714 Middle Street represents a rare opportunity to own one of the largest private residences on the island. Originally built in 1906 and located on the island's highest natural point, known locally as ''Mount Sullivan's'', this historic estate has been thoughtfully reimagined to preserve its architectural heritage while delivering the comfort and scale of modern coastal living. Recognized as a National Historic Registry home, the residence has undergone a comprehensive transformation behind its preserved exterior.Inside, soaring 13-foot ceilings and expansive living spaces create a sense of scale rarely found on the island. The chef's kitchen anchors the home and flows seamlessly into multiple gathering spaces designed for both everyday living and large-scale entertaining. The private owner's suite offers a peaceful retreat with its own screened porch, while the upper level features two newly added bedrooms with ensuite baths and a flexible living space. One of the home's most remarkable features lies on the lower level, an extraordinary entertainment space with ceilings reaching nearly 23 feet in height. Once used historically as a gathering space for soldiers, it has been transformed into a dramatic venue that can accommodate a wide range of possibilities, from wellness and recreation to automotive display or large-scale entertaining. A lounge, wine cellar, wellness studio, guest accommodations, and additional living areas complete this level. The grounds are designed for privacy and relaxation, featuring a resort-style pool, lush landscaping, multiple outdoor entertaining areas, and a detached guest suite. Nearly every major system has been replaced or rebuilt, including a new roof, electrical, plumbing, HVAC systems, and a whole-home generator, offering the integrity of historic design with the reliability of modern construction. Sullivan's Island is celebrated for its pristine beaches, relaxed sophistication, and unmatched coastal lifestyle, all just minutes from historic downtown Charleston. Properties of this scale and historical significance are rarely available, and opportunities like this are unlikely to be recreated.