Hillside was built in 1861 by Franz Wilhelm Rittelmeyer (1824-1877), a German-born carpenter. Rittelmeyer and his wife Mary Elizabeth “Eliza” Rittelmeyer (1826-1909) immigrated from Prussia to the United States on November 8, 1851, arriving at the port of New Orleans on the ship Ernestine. The Rittelmeyers settled in Memphis, Tennessee, where they lived until 1857. In that year, Franz was hired as the master carpenter for Airliewood , the Gothic Revival mansion built by the Coxe family in Holly Springs. The Rittelmeyers moved to Holly Springs, where they built a small cottage, now called the Gaw House, just west of the railroad.
In about 1861, Franz Rittelmeyer (who now anglicized his name as Francis William Rittelmeyer) built his own masterpiece, the Italianate and Gothic Revival Rittelmeyer House. Located on a prominent hill east of the town center, the home was one of the best examples of Italianate/Gothic architecture in the area. After Francis and Eliza’s death, their daughter Emma Rittelmeyer (1854-1936) lived in the house. The Rittelmeyers owned the house for 75 years, until Mack C. Simpson Sr. (1878-1854) purchased the house in 1936.
Between 1945 and 1968, Hillside was owned by Curtis P. Ayers Jr. and his family. Glenn E. Hascher owned the house from 1968 to 1972, and Samuel B. West Jr. (1923-1992) and his family lived here from 1972 until 1999. Christian and Jennifer Knox lived in the house between 1999 and 2006, when it was sold to Wallace Lester and Shannon McNally. Wallace Lester has owned the house since 2016.
Hillside is an Italianate and Gothic Revival one-and-a-half-story flanking-gable frame house, with front-gable dormers with brackets and arched windows. There is a three-bay porch with Gothic arch openings and spandrels with quatrafoil motifs. A two-story hip-roof tower on the west elevation has a flat roof bay with paired windows and bracketed hood.