Built ca. 1817-1819 by Parke Poindexter. Poindexter was Clerk of the Court at Chesterfield County from 1812 until 1847. The original landowner was Henry Winfree, who received the property as a land grant in 1754.

Castlewood is one of the finest Federal period houses in Chesterfield County, featuring a formal five-part design with molded plaster ceilings in the main rooms, two stairways to each adjacent wings and beautiful carved mantels with King-of-Prussia marable surrounds.

Castlewood currently serves as the headquarters for the Chesterfield Historical Society and research library.