On the northwest corner of the Bradley-Wheeler House property in Westport is a heptagonal (seven-sided) cobblestone barn with an octagonal roof. It is thought to have been built circa 1847 by Farmin Patchin, a mason and blacksmith who owned the house at the time. The original uses of the barn are unknown, but it was possibly a smithy. The northwest corner of the building was originally attached to a wood frame barn that is no longer standing. Renovated in late 1980s/early 1990s, the barn is now home to the Museum of Westport History run by the Westport Historical Society.
At the intersection of Barnum Avenue and Harriet Street in Bridgeport is an Octagon house, built around 1856. The structure has the gravel wall with stuccoed exterior typical of this type of house, poularized in the 1850s by Orson Squire Fowler. Traditionally considered to have been built by P.T. Barnum, the house was actually built by Nathan Gould.
As requested, the octagon house built for Henry S. Smith in 1855 is located at the dead end of Bevin Boulevard in East Hampton. Smith was the son of Nathaniel C. Smith, who represented his town six times in the Connecticut General Assembly and served as town clerk for twenty-five successive years. The house, which has a porch and a later ell, has been owned by the Clark family since around 1900.
The Deming Sexon House is an octagon house on Middletown Avenue in East Hampton. The house appears to have two floors in the picture above, but on the other side the house’s basement is exposed and has windows, revealing that it actually has three floors. Deming Sexton was an East Hampton bell manufacturer.
An unusual octagon house with a Mansard roof is located at 86 Hallock Street in New Haven’s Hill District. It was built by Massena Clark, a real estate speculator who once had his own large estate on Whitney Avenue.
Located on Main Street in Old Saybrook is an octagon-shaped house known as the Ingham House. It was a prefab building, said to have been purchased from the Sears and Roebuck Catalogue around 1890. The attribution to Sears and Roebuck is open to question, because a number of online sources indicate that the company only began offering kit houses in 1908, and apparently such homes were only available in the United States starting around 1906. So the origins of the house must be considered as still undetermined. The building, which is not a completely symmetrical octagon, has been extensively remodeled to become a dentist’s office.
Addendum: The house was constructed by Horace Archer and was the residence of Robert Burns for many years. Robert Burns was a partner in the nearby Burns and Young store on Main Street. His daughter, Mary Burns, lived in the house and was postmistress for many years.