585 Old Stamford Road
The Greek Revival Style home at 585 Old Stamford Road known as the Joseph Weber Jr. Homestead has been the residence for some of New Canaan’s earliest families.
The original parcel of land was deeded to Joseph Smith from Seymour Talmadge. Joseph Smith was the son of “Tory Joe” Smith who had lost the family holdings during the Revolution. His new wife, Mary Talmadge, was the daughter of Joseph Talmadge of Flat Ridge. The Smith brothers expanded in this area -James the eldest remained in the family home; Minot had a house on Talmadge Hill; and Sherman built the home in 1840 for his new wife, Mary Elizabeth Hoyt.
The property included a three-story cow barn which bears the architectural markings of a structure built in the 1700s, including wooden pegs/nails and “triple marks” on the beams. At one time, there were four barns on the property as indicated in the 1956 subdivision map.
The New Canaan tax books in 1858 set the value of the home at $1600. In 1871, the value jumped to $2500 which suggests that renovations and an addition occurred during this era. The 1870 census also indicates that a farmer and his wife were sharing the residence with the Smiths.
When Sherman Smith died in 1878 and his wife died in 1891, the home passed to his adopted daughter and niece, Harriet Raymond Crofoot and her husband, Homer Crofoot, who was the general manager at Martin Bros., a clothing store in Stamford.
Mrs. Crofoot’s family sold the property to Mary Talmadge Kellogg in 1903 and then the parcel passed to her niece, Lorena Talmadge Taylor. In 1934, Mrs. Taylor married Mrs. Albert (Alfred) Waterbury who was the son of Isaac Newton Waterbury and Mary Miller. In 1937, Mr. Weber from South Orange, New Jersey, and his daughters, Edith and Grace visited George H. Jelliff at his home at Riverdale Farm. Mr. Weber’s daughter, Florence Bertha, married George H. Jelliff in 1916. (Advertiser 1/14/1937 article) Mrs. Waterbury sold the home to Joseph Weber Jr. and it remained in his possession until April 3, 1978 when it was purchased by Douglas Queen.
Mr. Queen sold the home in 1985 to Allen Stevens and it remained in Mr. Stevens family until it was sold in November 2022.
—Special thanks to Joanne Santulli for providing some of the research for this historic home.