Prior to the arrival of settlers from the Old World, Brays Island's earliest residents were Native Americans who roamed the South Carolina coast in a loose confederacy of fishing tribes. The colorful recorded history here dates back to the early 1600s, when it became part of a succession of land grants by the King of England. British Commander William Hilton, for whom Hilton Head Island was named, first wrote about discovering Brays Island in 1663.
Separated from the mainland by Haulover Creek and marshes, Brays Island's name is derived from William Bray, who traded with the native Americans and who was slain with his family by the Yemassee Indians in 1715. Later, during the American Revolution, various armies including Hessian and Loyalist troops fought on the island. In the 18th and 19th centuries, the sale of cotton and rice provided its residents with a fashionable lifestyle. During the Civil War, the area was ravaged and burned by General Sherman in his march to the sea. Brays Island remained as a working plantation through several owners including George Waterhouse, who bought it after the Civil War and was active in the business and religious life of nearby Beaufort, and then by Francis B. Davis of U.S. Rubber Company, who bought it in 1937. In 1963, the property was purchased by Sumner and Virginia Pingree of Boston, Massachusetts. Sumner farmed the property for approximately 20 years. In the late 1980s, in an effort to preserve his property, he decided to sell 325 one-acre lots and leave the remaining 94 percent as a shared playground. This provided these 325 families the ability to enjoy the type of lifestyle associated with owning a large recreational property at a fraction of the cost and without the managerial headaches associated with property ownership.