The Chestnut Street Area was documented by the Weston Historical Commission in 1998. The following properties are included in the area: 1, 7, 21, 27, 34, 36, 38, 40, 44, 52, 55, 56, 70, 72, 73, 74, 77, 78, 81, 84, 88, 99, 100, 109, 115, 118, 140 Chestnut St; 64 Highland St (formerly 140 Chestnut St)
The following is an excerpt from the 1998 Chestnut Street Area Form, which includes the complete text, data sheets, and photographs.
Chestnut Street is one of the earliest streets in Weston. The distinctive sharp bend in the path of the road reflects the earliest land division lines. This is one of the town’s designated scenic roads, loved for its gently rolling topography, stone walls, naturalistic landscaping, and “country” character. This area form covers the part of Chestnut Street from #1 to #118 and also #140. The western end of the street, which is not included, has recently been developed with large new homes on landscaped lots. Along the rest of the street, much of the open land is still maintained as meadow rather than lawn, and in general landscaping avoids a manicured appearance. Located at the eastern end of the street is the restored farmhouse generally considered to be the oldest remaining house in Weston. Several other houses along the street, although built in the 1950s and 1960s, are excellent, well-proportioned Colonial Revival examples which appear to be earlier in date. These houses lead most people to presume that Chestnut Street has many early historic houses, although, in fact, only one was built before 1870 and almost half of the houses within the area form date after World War II. Also contributing greatly to the architectural character of the street are a group of modest homes on small lots on the south side of the street, built between 1885 and the mid-1930s in a variety of styles. One feature of the street which accounts, in part, for its appeal is that nothing is regular or predictable. Lots sizes within the area covered by this form vary widely, from 1/3 of an acre to a high of over 10 acres. Age of houses ranges from ca.1696 to the present day. Set back of houses varies from about 10’ to almost 500’. Houses vary greatly in size, scale and design, from modest 1 1/2 story cottages to large mansions. What brings this disparate group of houses into something of a coherent whole is the sense that the street “feels” old and historic, that the street evolved “naturally” over time rather than through a subdivision process specifying regular lot sizes and setbacks, and that a high percentage of the houses, whether old or new, do not call attention to themselves. In future years, it is expected that this street will continue to be a favored location for new construction and also “tear downs,” to make way for new construction. If there is to be any hope of preserving the street’s special “sense of place,” it is essential that new houses be designed to fit in with the character of the street by using traditional architectural styles and informal, natural landscaping.
The earliest house within the area form, One Chestnut Street (ca.1696, MHC 223, Map #1) is generally considered to be the oldest house in Weston and is listed on the National Register of Historic Places. The house stands on its original site, set back from the corner of two country roads, with a meadow in front protected as conservation land. The house, which faces south, is a brown clapboard saltbox four bays wide, with a large modern ell added to the north at the east end of the lean-to. A large modern barn has replaced an earlier barn. Careful restoration by Philip W. Barker in 1961 revealed that the original house consisted of the two southwest rooms, one over one (18’ X 18’), a massive chimney with smoke chamber, and an entry-way and stair on the east end. About 1720, a lean-to was added on the north side, and about 1760 two additional rooms, one over one (13’ X 14’) were added to the east. The earlier lean-to was replaced by a larger one extending across the north side of the house. The next major renovation was in 1961, at which time the paneling and trim in the ca.1696 living room was made to conform to the style of the 1760 rooms.
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 landowners. 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.