Maidstone was originally located on 2000 acres of land along Herring Bay, in Anne Arundel County, Maryland. Samuel Chew (1660-1718) started construction and his son Samuel completed it after his father's death. The home was used as a Quaker meeting house before the Chews donated land for a new one. Maidstone remained in the Chew family for nearly 200 years.

Legend of the area says that incoming ships navigated the channel by lining up various Chew family residences. There is also a legend of the 'Ghost of Maidstone.'