Greystone, also known as the Dancy-McDermott House, was built in 1839 by J. Y. Cummings. The original house was a small, two-room Greek Revival cottage. In 1850, Dr. Francis W. Dancy (1810-1890) bought the house. Dr. Dancy was a physician and landowner who originally settled in the now-lost town of Salem, east of Holly Springs. Dancy was friends with future Confederate President Jefferson Davis. In the 1840s, Dancy and his family moved to Holly Springs, where Dancy practiced as a respected physician for several decades.
Dr. Dancy was present at the deathbed of two of the most tragic figures in Holly Springs history: the accidental death of Reverend Joseph Ingraham (1809-1860), Rector of Christ Episcopal Church, and the murder of James Henry Nelson (d. 1865) by mauraders during the last days of the Civil War. During the Civil War, Dr. Dancy’s 14-year-old son Henry Dancy (1846-1933) ran away from home and joined the Confederate army in Richmond, Virginia. A quick letter sent from Dancy to his old friend, and now President of the Confederacy, Jefferson Davis, resulted in young Henry being hurriedly sent home.
During the Yellow Fever Epidemic of 1878, Dr. Dancy was on the Marshall County Medical Board. The doctor knew how dangerous the Yellow Fever could be to the town, and wanted to quarantine the town, but he was overruled by the Mayor and Aldermen, which resulted in the deaths of hundreds of citizens.
The Dancy family continued to own the house until 1904, when it was sold to the Jewish Blumenthal family, who owned a popular store on the Holly Springs Square. Between 1907 and 1925, the house was owned by the Bradberry family. In 1925, the home was purchased by Robert A. McDermott (1864-1938) and his wife Dena McDermott (1866-1963). The McDermotts had previously owned the Holly Springs Depot before purchasing this home. The McDermott family renovated the house in the Georgian style in the 1920s, adding the front porch and gables to the original Greek Revival house. The McDermott family owned the house for 70 years, until they sold it in 1995 to Chesterfield and Beverly Brown. The Browns owned Greystone from 1995 until 2007. Bobby and Connie Rhea owned the house from 2007 until 2011. Since 2011 the house has been owned by Lewis Bailey and Kevin and Stephanie Cavender.
Greystone is a one-and-a-half story frame Greek Revival house, with a 1920s Georgian addition of a porch supported by Tuscan columns and two front gables. The entrance has a transom and sidelights. The home gets its current name from the grey stone wall which surrounds the front of the property. Outside the front is the last remaining hitching post in Holly Springs, which would have been used to hitch horses in the decades before the coming of the automobile and would have once been located throughout the town.