Hilltop was built in 1856 by George W. Reynolds. It is built on the spot of the original Randolph Outpost, built before the town of Holly Springs was founded in the early 1830s on the east ridge overlooking the original “holly springs”. In 1860 the house was sold to John D. Fennell (1809-1879), a wealthy planter who moved to Holly Springs to send his children to school. The Fennell family owned the house for many years, and it was called the Old Fennell Place for much of the 19th century.
In 1872 William C. Jones married John Fennell’s daughter, Conley Fennell (1854-1918) at Hilltop. By 1900, William Jones and his wife had inherited Hilltop from John Fennell. The Jones family owned the house until 1940, when it was sold to William Sumner Hill (1888-1960) and his wife Alma K. Hill (1897-1968). The Hills owned the house for thirty years, and eventually sold it to John C. Williamson. Between 1970 and 1988 it was owned by the Williamson, Moody and McKinney families. Between 1988 and 2002 this was the home of Bobby and Kathy Clanton, who sold the house to Doctor Joseph A. Hale in 2002. From 2009 until 2015 the home was owned by Paul Thimmes. It is currently owned by David and Pam Zelman.
Hilltop has a local reputation for being one of the most haunted homes in town. A ghostly child is frequently heard crying in the house.
Hilltop is a Greek Revival frame house, with flanking gables, a three-bay pedimented portico supported by Tuscan piers, pilasters, and a full entablature. The main entrance has a transom and sidelights. The house was renovated and reduced in size in the 1940s.