Built in 1919, this building was first leased by Winchester Motor Co., which sold Ford automobiles and Fordson Tractors. In 1926, the Rollaway Skating Palace, with its highly polished maple floors, opened here. A variety of wholesale grocery companies used the building, until it was rented for Vaughan hardware's building Materials business. T.C. Simmons Insurance, operating in Winchester through three generations since 1921, came to this location in 1971, and optometrist W.E. Eichenberger used the corner rooms from 1981 to 2000.