Designed by Ehrick K. Rossiter, the 1904 Seymour Cunningham House, on South Street in Litchfield, is an example of the types of high style Colonial Revival houses that were built as summer homes for the wealthy in the early twentieth century. Seymour Cunningham was the son of William Orr Cunningham, a wealthy papermill owner from New York State. Seymour married in 1892 and it is possible that he built the house the following year, 1893. That is the date given in a biographical sketch of Cunningham in the Genealogical and Family History of the State of Connecticut, Vol. II (1911):
Seymour, son of William Orr Cunningham, was born in Troy, New York, September 13, 1863. He attended the Troy Academy. Later he entered the Rensselaer Polytechnic Institute and graduated with the degree of civil engineer in 1884. He became interested in the oil business in Pennsylvania and Ohio. In 1887 the old home at Troy, New York, was sold and he brought his mother to Washington, D. C., and built a residence at No. 1719 K street, where he still maintains his winter residence. His Litchfield home, “Forked Chimney,” was built in 1893, on South street, near the site of the old Parmelee house. In politics he is a Republican. In religion he is an Episcopalian. He married, June 6, 1892, Stephanie Whitney, of Oakland, California, born October 22, 1869, daughter of Hon. George E. Whitney, lawyer and state senator of California, and Mary (Van Swaringen) Whitney, of Louisville, Kentucky. Mrs. Cunningham was named Stephanie in honor of her uncle, Justice Stephen J. Field, of the United States supreme court. Children of Mr. and Mrs. Cunningham: Cecil, born March 8, 1893; Macklin, February 21, 1894; Jane Chester, February 27, 1896; Pamela, May 5, 1906. The three oldest were born in Washington, D. C., the youngest in Litchfield, Connecticut.