Castlewood is one of Chesterfield County's finest and most puzzling early 1800s houses. The five part building was erected in several stages of uncertain sequence. The land on which the house was built was patented to Henry Winfree in 1754 and remained in the Winfree family until 1816. At that time 180.5 acres were sold to Parke Poindexter, the clerk of the Chesterfield County Court from 1812 until his death in 1847. According to Chesterfield tax record, Poindexter was assessed for 300.5 acres of land and for buildings valued at $3,000, of which $2,600 worth was noted as having been added since 1817. From this evidence, it would appear that by 1820 the house had reached its present state, except for the decoration in the south wing.
During its history, Castlewood has had many owners. Between 1860 and 1872, the home was used by the Methodists to house traveling ministers. It is believed the name Castlewood was first applied to the house by James H. Lumpkin, owner from the 1920s to 1957. The house was converted into use as a bank in 1977. In 1992 the property was acquired by the Chesterfield Historical Society, and the house now serves as its headquarters.
Castlewood was listed on the Virginia Landmarks Register of June 15, 1976 and the National Register of Historic Places on November 21, 1976. Castlewood is the home of the Chesterfield Historical Society library. As a research facility it focuses primarily on the history of the county and its families. For more information please visit: Chesterfield Historical Society.