The oldest house in Windsor is the Loomis Homestead, located on the campus of Loomis Chaffee school. The oldest part of the house is now the south ell, built by Joseph Loomis in 1640. His son, Deacon John Loomis built the main section in 1688, the year he died, possibly for his son Timothy. In the 1870s, planning began for what would become Loomis Chaffee, established by five Loomis siblings, children of Colonel James Loomis and Abigail Sherwood Chaffee, who had all lost their own children. The school’s first buildings, completed in 1913-1916, were designed to match the axis of the Loomis Homestead, several degrees off of true north. The old house itself remained in the Loomis family until Miss Jennie Loomis deeded it to the Loomis Institute in 1901. She continued to reside in the house until her death, in 1944. Then it became a residence for a member of the Loomis Chaffee School faculty and continues as a museum and memorial to the Loomis family.
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