Henry Bissell was a prominent Litchfield farmer. In 1860, he owned 72 acres of farmland with 5 dairy cows, and his holdings only increased over the years. When the Shepaug Railroad started running through Litchfield in 1872, dairy farming became increasingly lucrative, since farmers could now ship milk daily to New York. By 1870, Henry Bissell had 9 cows, and by 1896, 20.
Henry Bissell died in 1887, and the property passed to his children Francis and Amelia Bissell. The house remained in the family until 1985.