Created by an act of Colonial Assembly in 1768, New Windsor was established on the site known as Gray's Landing. A part of grants to the Lords Proprietors, 2800 acres on the Cashie River were sold in 1717 by John Lord Carteret, Earl of Granville to Thomas Pollock. His son, Cullen, sold to John Gray 1,000 acres of the "Rosefield" Plantation in 1722. William Blount, a Gray descendant who was born at Rosefield, became a member of the Continental Congress and a signer of the Federal Constitution. He later became Governor of the Southwest Territory and a U.S. Senator from Tennessee. Today the National Register Historic District encompasses some of the same area.
Passing through the Historic district one sees stately homes many of which were built in the 18th and 19th centuries.
Windsor has served as the county seat of Bertie County since 1794 when the courthouse and prison were moved by the Assembly from the old town of Cashy. It continues as the county seat and the center of an agricultural and industrial economy based on farm products and the timber industry.