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.
Like the neighboring house at 224 Cornwall Avenue, the house at 214 Cornwall Avenue in Cheshire was built in the 1850s by Edward A. Cornwall to rent to rent to one of the many miners from Cornwall, England who were emigrating at the time to Cheshire to work in the barite mines. Barite was discovered in Cheshire around 1840 and mining activity continued until 1878. The house was purchased for $850 by William Moon, a miner from Cornwall, in 1862. He paid $$250 down with a $600 mortgage held by Edward Cornwall. The current owners have expanded the house in recent years. (pdf source)
In the nineteenth century, Cheshire became famous for its barite mines. Barite was discovered in Cheshire around 1840 and mining activity continued until 1878. Many miners from Cornwall in England settled in Cheshire to work in the mines. One such miner was Richard Brown, who rented the house at 224 Cornwall Avenue. It was built in the 1850s as an investment property by Edward A. Cornwall, a prominent citizen of Cheshire. Cornwall sold many other parcels of land from the Cornwall Farm, which went back in his family to the 1790s. Richard Brown later purchased the house with a mortgage held by Cornwall. The house was a twin of the residence next door at 214 Cornwall Avenue, which was also a rental property erected by Cornwall. The house at 224 Cornwall has a later Victorian front porch. The large dormer on the west side of the house was added in the late 1970s. (pdf source)
The house (pdf) at 240 West Main Street in Cheshire was built circa 1845 for Augustus C. Peck, a mechanic. In the 1860s, the Greek Revival house was purchased by Dr. M.M. Chamberlain, who enlarged and modified it with Victorian additions.
Adjacent to northeast of the First Congregational Church of Cheshire is a house built around 1835 (1831-1836) for Rev. Joseph Whiting, who served as the first minister in that church building, from 1827 to 1836. The house was owned by a number of ministers over the years. Arthur Sherriff, headmaster of Cheshire Academy from 1923 to 1966, was a later resident of the house, which was sold to the Congregational Church in 1969. The Greek Revival-style house has a later Colonial Revival porch.