Isaac Buck built the house at 14 Maple Street in Chester by 1755 on land he had acquired in 1750. He divided the house and barn with his son Justus. Justus’ son, William Buck, sold the house in 1798. Later, in the nineteenth century, the house was owned by Joshua L’Hommedieu. He settled in Chester in 1812 and, with his brother Ezra, became an early manufacturer in town. He also represented Chester in the state General Assembly. At some point the colonial-era Isaac Buck House acquired Federal and Greek Revival-style exterior ornamentation.
The oldest house in Chester is the Thomas Dunk House, at 16 North Main Street, now home to the Thomas Dunk House Gallery. The exact date of the house’s construction is not known, but it was built sometime between 1672, when the land was deeded to Thomas Dunk, and 1711, when his son, Jonathan Dunk, was born in the house.
The Greek Revival house at 64 West Main Street in Chester was built around 1830. Associated with Julius Smith, a dealer in dry goods and groceries, by 1859 the house was home to L. Norton. Stuart Joslyn bought and restored the house in the 1930s, one of several old houses he and his first wife restored on West Main Street.
The first Catholic mass in Chester was held in 1851 and a church was built on Middlesex Ave in 1855. At that time, the Parish served the towns of Chester, Deep River, Essex, Old Saybrook, Westbrook, Old Lyme, Lyme, and Haddam. The Parish received a full-time pastor in 1876 and the current church replaced the original one on the same site in 1891. To make way for the new church, the first church building was sold and moved to the corner of Main Street and Middlesex Avenue. The new St Joseph’s Roman Catholic Church was dedicated on February 16, 1892. The church was enlarged in 1929, at which time the peak of the gable roof was lowered and two smaller towers on the right of the front facade were removed.
George M. Abbey was a builder who constructed several houses in Chester, including one for his son, G. Myron Abbey. Nearby, Abbey had earlier built the house at 54 West Main Street in Chester in 1865 for himself and his wife, Lois A. Abbey. Their descendants continue to live in the house.