There were many controversies related to the construction of the Winchester Town Hall building. In 1877, town leaders appropriated funds to build a town hall so as to provide a safe place for the town records. Before most people in town were aware of it, these men had moved quickly to start construction of the building in an area called the Flat, part of the central business district of Winsted. People in other parts of town, who thought that the building was unnecessary and too expensive, felt that promoters of the Flat had stolen a march on the voters, but at a contentious town meeting those who wanted to press on with the building won out. An injunction to halt construction was soon dissolved by the court and the building was completed in 1878. Bitter feelings over the episode continued for many years. The building was expanded in 1887 and 1904 for use by the County Court. Plans for a 25-foot addition on the front of the building fell through in 1910, but when this was finally done in 1927, the structure gained a more convenient entrance at street level.