In pre-colonial times, numerous Native American cultures occupied Callawassie Island for 5,000 years and left their mark in archaeologic remains, shell middens, and a Native American burial mound. Some artifacts are exhibited in the Clubhouse entrance hall for Callawassie Island residents and visitors to enjoy. In the early 17th century, the Yemassee Indians gave Callawassie Island its name and occupied the Lowcountry until their expulsion by the English.
The beautiful ruins of the tabby sugar mill can be found on Callawassie Island today and are a registered national landmark. James Hamilton, a legislator and general, was the gentleman who constructed this sugar mill on Callawassie Island during the plantation era. Sugar cane did not prosper but the old mill remnants remain.
The island evolved over the centuries from a thriving indigo plantation to a southern playground for the nation's industrial elite. In 1981, Callawassie Island established its modern identity as a serene residential community featuring signature amenities.