Holly Hill stands on land originally granted to James Robeson in 1768 as part of England’s expansion into the S.C. backcountry. Robeson sold the property in 1778 to Sarah and Jenkin Harris, whose sons Jenkin Jr., John, and Moses became active in the development of Edgefield Village. Charles Goodwyn, a lawyer and state senator, later lived there until his death in 1824, and architectural study suggests that the eastern half of the house may date to the 18th century. In the 19th and 20th centuries the house passed through a series of owners, including Sheriff Humphrey Boulware, Irish immigrant and Catholic leader Peter McHugh, planter and physician Dr. C.P. Devore, and Edgefield socialites Wallace and Adrienne “Dollie” Dugas Sheppard. In 1919 Benjamin Tillman Lanham purchased the property and operated a dairy there, and the Lanham family lived in the house until the 1970s.