The house was once the home of Roger Barton who was nominated to congress, the Senate and U.S. Consul in Havana. All of which he refused. Greenwood is said to have been built when Holly Springs was an Indian trading post and there were little to no other houses built. The home does not face the street because, legend has it, there was nothing between the house and the town square at the time and Mr. Barton wanted to sit on his porch and be able to see everything going on downtown. The home was also used as a Catholic girl’s school until 1907. In 1979 a restoration began which unearthed a small tunnel beneath the dinning room said to have hidden valuables and used for escape during the Civil War. In uncovering the walls it was found that small trees still covered in bark were used for studs.