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Rev. Simon Shailer became minister of Haddam’s Baptist Church in 1822. In 1827, he built a house on Saybrook Road in Shailerville adjacent to a house he had constructed for his son that same year. The houses are very similar in their Federal style design, although the Simon Shailer House has a Victorian-era balustraded porch with a hipped roof. Another son of Simon Shailer, Nathan Emery Shailer, also became a Baptist minister. After Rev. Simon Shailer died in 1864, his widow and daughter lived there and it is now owned by a descendant.

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The Simon Shailer House (1827)