The brick house at 273 South Main Street in Cheshire was built c. 1850. It is transitional in style between the Greek Revival and the Italianate Villa. Two owners of the house in the mid-nineteenth century were E. Talmadge and U. P. Hokum.
Warren Doolittle (1813-1870), who ran a farm and was secretary and treasurer of the Cheshire Manufacturing Company, was one of Cheshire’s wealthiest citizens. One of two houses he owned on West Main Street in Cheshire was an Italianate villa (345 West Main Street) that was built c. 1860.
The house at 568 South Brooksvale Road in Cheshire was built in 1851 on land long owned by the Brooks family. The first residents of the house, which was known as the Glebe House, were Rev. David March and his wife, Anna Brooks March, whose brother David Brooks had deeded the property to her. Rev. March was pastor of the Cheshire Congregational Church from 1845 to 1848.
Frank E. Aldrich purchased the lot at 254 West Main Street in Cheshire in 1919. Probably by the next year he had built a Colonial Revival house that also has features of the Neo-Classical (the columns) and Craftsman (exposed rafters) styles.
The Queen Anne house at 242 South Main Street in Cheshire was built circa 1895. At that time the land was owned by Annis Williams (1837-1924), an heir of stage driver Norvil Williams, who had an earlier home on the site. The house later became a funeral home.
The house at 500 South Brooksvale Road in Cheshire combines elements of the Colonial Revival and Craftsman styles. Known as Brookside, it was built in 1898 as a summer cottage for Peter Palmer of Brooklyn.
The house at 108 Cornwall Avenue in Cheshire was built in the 1880s by James Gardner Clark. It was sold to James M. Speake in 1905 and then to Susan Hotchkiss in 1909. The house was used to board students of Cheshire Academy in the 1940s and 1950s.