The original Tyson House was an antebellum house, presumably built in about 1849 by Warren Caldwell. It was located across the street from the Caruthers House (1842). It was owned by F. T. Bradley from 1857 until 1889, when he sold the house to Medora “Dora” Alexander Tyson (1854-1933) and her husband James Owen Tyson (1839-1906). As early as 1892, this first house was being used as a boarding house for local bachelor men. Early Holly Springs historian John Mickle lived in the Tyson Hotel for much of his later life. In about 1900, the Tysons built a new building just to the west of the original building, on the corners of today’s Gholson Avenue and Market Street. This second house was a large Victorian home that was also known as the Tyson Hotel, and provided lodging (both temporary and permanent) for women. In 1901, Dora Tyson deeded the newer house to her two daughters, Kate Tyson (1881-1949) and Lucy Tyson (1883-1961). The Tyson girls continued to live in this home and run the hotel for the next fifty years.
In 1906, James Tyson died, but his wife Dora continued to run both Tyson Hotels for many decades, until her death in 1933. Besides the two Tyson daughters, there were also five brothers: Edmund Tyson (1885-1963), Robert Tyson (1887-1953), James Tyson (1889-1964), Joseph Tyson (1891-1957) and Frederick Tyson (1892-1949). Most of these Tyson brothers continued to live in the original antebellum Tyson home, and all were well known in the local community. Joseph Tyson became a pharmacist and later founded Tyson’s Drug Store, which continues today a block north where the Tyson House stood.
After the death of Lucy Tyson in 1961, both the original Tyson House and the Victorian Tyson Hotel were destroyed. In the 1970s, the current building was built on the same lot and was used as the Greer and White Insurance Office for many years. As of 2018, it is the home of the Law Offices of Jennifer Shackelford, Amery Moore and Collier Carlton.