Holly Springs contractor and merchant Joel Wynne built the house. After the Civil War, Mrs. Anne Dickens, a widow from Kentucky, bought the house and was criticized for entertaining Union soldiers during the war. The rumors proved to be true when Union Lieut. W. A. Newton, who was the most hated military figure in the county, and Mrs. Dickens fell in love and married. They moved away in 1880 and the home then went to a gambler who wagered the home in a poker game and lost. The home was in his wife’s name but she honored the bet and moved out. The current dining table in the home, marked and dated 1830 by Berkey and Gay, first belonged to Reverend Newitt Vick, founder of Vicksburg.