Smith-Dickinson House (1842)

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In 1841-1842, Charles Whitmore Smith, a merchant, built a Greek Revival house on North Street in Essex. In 1888, the house was purchased by Edward E. Dickinson, whose E.E. Dickinson Company dominated the nation’s production of witch hazel. Dickinson wintered in Florida, where the wealthy community of Palm Beach was being developed at the time. In 1927, Dickinson enlarged and remodeled his house in Essex to resemble Whitehall, Henry Flagler’s famous mansion in Palm Beach.

The William Jillson House (1826)

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In 1826, Asa Jillson and his brother, Seth, from Rhode Island, arrived in the Borough of Willimantic in the Town of Windham, where they became industrial pioneers, setting up mills and building a stone house, built of gneiss granite quarried from the Willimantic River. Asa’s son, “Colonel” William Lawrence Jillson, had arrived with his father and eventually became the agent for his father and uncle’s textile manufacturing firm, the A. & S. Jillson Company. William L. Jillson worked with the machinist Ames Burr Palmer to invent the Jillson and Palmer cotton opener, which came to be used throughout the country. Jillson founded other textile factories and, when he died in 1861, control of his companies passed to his son, William Curtis Jillson, who became one of Willimantic’s most prominent citizens. By the 1970s, the stone Jillson House had fallen into disrepair. It was restored and became the home of the Windham Historical Society.

William Hart House (1767)

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Located next to the First Congregational Church in Old Saybrook is the 1767 house of General William Hart, which is now the headquarters of the Old Saybrook Historical Society. Hart was a merchant engaged in the West Indies trade with his brother, Joseph. During the Revolutionary War, he outfitted privateers and led the First Regiment of Connecticut Light Horse Militia to Danbury, when that town was raided by the Brittish under Brig. Gen. William Tryon in 1777.

Elizabeth Apthorp House (1837)

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In 1838, Elizabeth Apthorp moved from her first home on New Haven’s Hillhouse Avenue, which she had been sharing with her half-sister, Abigail Whelpley, to another one nearby, again arranged by James Hillhouse and newly completed the year before. The Apthorp House was designed by A.J. Davis. He described the house as an Etruscan Villa, although its overall shape conformed to the Greek Revival style and the original focus of the facade was an Egyptian Revival porch. The building has been constantly added to over the years with new and reused elements in a variety of styles. In the early twentieth century, the house was occupied by the family of former Yale president Timothy Dwight. It is now owned by Yale and is one of the buildings housing the Yale School of Management. It was renovated in 2001.

Eugene Boss House (1882)

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Eugene Boss rose from being a bookkeeper for the Willimantic Linen Company (later the American Thread Company) to becoming the mill’s agent (or manager), a position he held from 1879 to 1916. He was, literally, boss at the mill. The company had a private rail network between its buildings and the train was pulled by an engine, the Helen B, named after Boss’ daughter. Boss’ house in Willimantic, on Windham Street, from which he could look down on the company’s mills, was built in the 1880s.