The history of Chestnut Street follows a pattern very common in Weston history. Until the late 19th century, Weston was predominantly an agricultural community and land on Chestnut Street was part of several farms. Only one of the early farmhouses remains today. As in other areas of Weston, these farms were purchased in the late 19th and early 20th century by well-to-do Boston business and professional men who developed country estates here.
The eastern end of Chestnut Street was part of the William Hill estate and the western end was largely bought up by General Charles Jackson Paine, one of the first and most important of Weston estate owners, who was to become the town’s largest landowner. A small farm and Colonial farmhouse no longer standing at the bend of the road also became a country retreat belonging to Boston lawyer E. Sohier Welch.
All three of these properties were run as “gentleman’s farms” well into the 20th century. Some of the Paine estate land is still owned by family members, who have preserved several of the original estate buildings and undeveloped land. The rest of the land formerly part of these country estates was gradually subdivided, in most cases after World War II, into large lots for the building of substantial new homes.
Another farm on the street, the Barker Farm on the south side, was never bought up by the Boston contingent, and for this reason followed a different development pattern. This land was subdivided again and again as pieces were sold off or deeded to family members. The result is that this part of the street was developed with modest homes on small lots owned by Barker descendants, staff of nearby estates, and local tradesmen.