John L. Cleveland, born in Georgia in 1851 to James Monroe and Catherine Wright Cleveland, studied agriculture and business before moving to Midlothian, Texas, to teach and farm. Annie Hamilton Upshaw, daughter of Samuel Crockett and Attelia Aldridge Upshaw of old Washington, Texas, later moved with her family to Hillsboro and attended Stuart Female Seminary in Austin. She and Cleveland married in Hillsboro in 1884 and settled in Cleburne, where they bought two lots from B.J. Chambers in 1887. They began building their home in 1892 and moved into it the next year. Both were instrumental in forming Main Street Methodist Church. John owned the Cleburne Cottonseed Oil Mill until it was destroyed by fire in 1907, and he also owned a hardware store and sold cars in Cleburne, though he did not learn to drive until he was 80 years old. He belonged to the Knights of Pythias, the school board, and the Democratic Club of Cleburne. Annie, also called Anne, served as president of the Cleburne Chapter of Circle of Kings Daughters, led the local Red Cross Canteen during World War I, and in 1925 helped organize the city's Parent-Teacher Associations and the Cleburne Council of Mothers, later the City Council, serving as the group's first president. The couple had ten children, six of whom lived to adulthood. John died in March 1936, Annie died four months later, and their children sold the house in 1941. Later owners preserved the historic home's appearance, including its Queen Anne style with Eastlake details, decorative fishscale shingling, polychromatic painting, sunburst motifs, a prominent modified keyhole window, and spindled friezework.