Dr. Hezekiah Chaffee House (1765)

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Built for Dr. Hezekiah Chaffee on Palisado Green in Windsor around 1765. The Georgian style house is constructed of brick and features a gambrel roof. John Adams dined there in 1774. Dr. Chaffee’s daughter, Abigail, married Colonel James Loomis in 1805. In 1874, their children, including the state senator James Chaffee Loomis, founded the co-educational Loomis Institute. The Chaffee House would later be utilized by the girls’ division, which broke off in 1926 to form the Chaffee School. The two branches reunited in 1970 to form the Loomis-Chaffee School. Records survive relating to the slaves owned by Dr. Chaffee, including the documents for the emancipation of Elizabeth Stevenson. Another slave in the Chaffee household was Nancy Toney, who was later owned by Dr. Chaffee’s daughter, Abigail. When she died in 1857, she was the last surviving slave in Connecticut. The house is now owned by the town of Windsor and is currently open as a museum, maintained and operated by the Windsor Historical Society.

The John and Sarah Strong House (1758)

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The Strong House, on Palisado Avenue in Windsor, was long thought to have been built in 1640 and was known for many years as the Lt. Walter Fyler House. Fyler came to the Massachusetts Bay Colony from England in 1630, settling in Windsor in 1634. He received the land on which the house now stands in 1640 for his service in the Pequot War. Recent research has shown that Fyler’s house actually stood on a different part of his property than the house that was latter attributed to him. The area where this surviving house now stands was later owned by Henry Allyn, who sold it to John Strong, Jr. in 1758. When Strong later sold the property to Alexander Allin in 1762, it contained a dwelling which had not been there before. This is the house which is now called the John and Sarah Strong House.

The original, 1758 gambrel-roofed portion of the house was a half-house, a middle-class home intended to be added to later, as it was with more elaborate additions over the years. The house was saved from demolition in 1925 by the Windsor Historical Society. The house has served the Society as a headquarters, and even as a tea room for several years in the 1920s. Research into this historic structure continues and it is currently open for tours as a house museum.

Oliver Ellsworth Homestead (1781)

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The house of Oliver Ellsworth, on Palisado Avenue in Windsor, was originally at the heart of the Ellsworth estate, called Elmwood. It was built in 1781 by Samuel Denslow, to Ellsworth’s specifications. Oliver Ellsworth had been born on the property in 1745 and went on to become a member of the Continental Congress during the Revolutionary War, an envoy to France, a framer of the U.S. Constitution, the chairman of the Senate Committee that framed the bill organizing the federal judiciary system, and the third Chief Justice of the United States. Ellsworth married Abigail Wolcott Ellsworth in 1772 and the couple lived in the house until his death in 1807. Two sitting presidents visited the house, George Washington in 1789 and John Adams in 1799.

In 1788, Ellsworth commissioned Thomas Hayden, a notable Windsor architect-builder, to construct a two-story addition to the house on the south elevation. The addition’s first floor was a drawing room, in which Ellsworth’s daughter Abigail married Ezekiel Williams, son of the merchant and Hartford County Sheriff, Ezekiel Williams of Wethersfield in 1794. Ezekiel Williams Sr had served with Ellsworth on the Committe of the Pay Table during the Revolutionary War. The Greek Revival-style colonnaded porch was added by Martin Ellsworth in 1836. Members of the Ellsworth family continued to live in the house until 1903. It was then deeded to the Connecticut Daughters of the American Revolution by Oliver Ellsworth’s descendants. Restored in the 1980s and 1990s, the house is open to the public as the Oliver Ellsworth Homestead.