The oldest extant part of the house was built in 1751 by a yeoman planter, Lewis Lewin on or near the site of an earlier wood structure.,[2] though a brick in one of the chimneys is dated 1678.

Maidstone Plantation was originally in Anne Arundel County in the Province of Maryland prior to boundary shift.

[3] In 1755, Thomas Whittington and his wife Wilhelmina Powell purchased Maidstone with the proceeds from the sale of a portion of her inheritance, a plantation called Gory Banks.

Thomas Whittington's will, which was probated February 9, 1786, gave one half of his land containing Maidstone "where my Dwelling house stands" to his oldest son John.

After her death, it became the property of John Whittington's daughter, Mary, who married Henry Childs on June 26, 1820.