Dewberry Hill began as a one-story-with-garret house, built in the 18th or early 19th century. In the late 1860s, Dr. Thomas Herndon Miles and his wife, Lucie L. Palmer Miles, added a two-story, sophisticated Italianate house to the front of the original dwelling and developed the property into a prosperous tobacco farm. Dr. Miles studied at New York University in the 1840s and became a respiratory specialist. Advertising his services in regional newspapers, he received patients in an office erected on the front yard.  The builder of Dewberry Hill is unknown, although local African American carpenter Leander Cunningham may have been involved. An elaborately scrolled stair newel was likely acquired from the workshop of African American cabinetmaker and finish carpenter Thomas Day in nearby Milton, North Carolina. Later owners included Dr. William M. Palmer and the Wilson, Dewberry, and Adams families.