When Chestnut Street opened in the mid-1880's, Ellen Davis, a former enslaved woman, bought one of the first houses on the street.
Garrett Wilgus, a building contractor and brickyard owner, announced plans in 1884 to open Chestnut Street from Third Street to his brickyard on Seventh. Wilgus ran newspaper ads saying he was selling lots “very cheap for cash.”
In 1886, Davis bought the house at 335 Chestnut Street. Davis was enslaved by John T. Hughes, a thoroughbred horse breeder with extensive land holdings along Winchester Pike. At the age of 18, Davis had a son by Hughes, who acknowledged he was the father of the child and sent him to New York to be educated. They never married, but their relationship continued for the next 63 years until Hughes’ death.
When Hughes died in 1924, he left the bulk of his estate to Davis, making her a wealthy Black woman. Their son Col. John H. Hughes returned to Lexington, and Ellen Davis bought the imposing residence at 340 East Third Street in 1926, where she lived until her death in 1927.
John H. Hughes lived there until his death in 1935. Today it is the Smith & Smith Funeral Home.
The New York Times covered the story in 1925, publishing an article titled, “MADE RICHEST NEGRESS IN SOUTH BY COURT; Bequest of Hughes Estate to Former Slave Upheld -- Payne Whitney Buys Elkton.”