This simple, gable-front building was constructed circa 1870. The earliest records show Henry Crawford as the owner; however, he lost the building at sheriff sale in July 1873. It was purchased by Ruben Main for $1333 at the sale, and sold by Main the following year for $2400. The purchaser was Martin Kiefer, who operated a saloon here. The building continued to operate as a saloon under various names until the late 1910s.

When the building at the northeast corner of Pearl and Market streets was torn down in 1929 to make way for the new Kresge Building, Harry McDonald moved his drugstore to this location. After Mr. McDonald's death in 1944, his heirs sold the store, its fixtures and contents to the Louisville drugstore chain of T.P. Taylor & Co., and this became the first Indiana location for Taylor Drugs. Taylor Drugs remained here until the mid-1960s when it moved to a suburban location on Charlestown Road. Mills Discount Pharmacy then occupied the structure until the mid-1990s.