The Jon and Roberta Gillespie house, located at 301 N. Oak Street, was constructed between 1909 and 1910. John Gillespie worked at the Continental State Bank. John Gillespie’s widowed mother, Cass, had moved to Texas with her three children in 1878. She later became a housekeeper for her sister, Mrs. Isabell (Sam) Reynolds. The Reynolds family had a large ranch near Roanoke and were involved in several business ventures in the community. After Isabell Reynolds’ death, her sister Cass married Sam Reynolds. Sam was the only father that John Gillespie ever knew. After World War I, the house belonged to the Seagraves family. J.H. Seagraves had a hardware and dry goods store on Oak Street (no longer extant).