Pigeon Hill was the first “planned” subdivision in Weston. Until the later part of the 19th century, the town was primarily an agricultural community; and new houses, when needed for local farmers and tradesmen, were generally built along existing roads.

By the late 19th century, Weston was beginning to attract Boston businessmen who established country homes on large tracts of land purchased from local farmers. These men, in turn, encouraged other business and professional men to settle in Weston, creating a demand for middle class houses in the type of “suburban” neighborhoods which were growing up outside cities across the country. One of the first persons in Weston to recognize and address this demand was estate owner Horace Scudder Sears, who grew up in Weston as the son of the First Parish Church minister and remained in the community even after he made a fortune in textile manufacturing.

In the last few years of the 19th century, Sears purchased the land on Pigeon Hill, had a subdivision plan drawn up with 17 lots, and then sold the lots to business and professional men including a doctor, lawyer, bookseller, and several architects. One of the attractions of the new subdivision was its proximity to the Central Massachusetts Railroad, which opened in 1881 and had a station at the foot of the hill just outside the limits of this area form. In 1904, the subdivision became the location for the Pigeon Hill School, the first private school in Weston. 

Historical Estates

Samuel Mead House

The first house to be built on Pigeon Hill, the Samuel Mead House of 1891 (MHC 254, Map #19) was not part of the Sears subdivision. Some years earlier, the young architect had designed a brown shingled house for his contemporary, Robert Winsor, who would become Weston’s second largest estate owner. After designing Winsor’s relatively modest house, which still stands at 309 Boston Post Road, Mead embarked for Europe for three years of travel and study as the second winner of MIT’s prestigious Rotch Traveling Scholarship.

After his return in 1887, Mead moved to Jamaica Plain and began a career with well-known Boston firms including Ware and Van Brunt; Cabot and Chandler; Cabot, Chandler and Mead; and Cabot, Everett and Mead. For his own house, Mead remembered Weston and returned to the country town, choosing a hilltop lot with a beautiful view in an era when Weston was largely deforested. In 1892, he was taxed for a house and stable valued at $3,100 and eight acres of land. On the property he also built a carriage house and a greenhouse for Mrs. Mead, who was fond of gardening and oversaw the original landscaping of the property, as well as the planting of an exceptional collection of rhododendrons.

Mansions Designed by Samuel Mead

In the years after he settled in Weston, Mead designed impressive mansions for Lorenzo Kettle (ca.1892) at 770 Boston Post Road, Grant Walker at 319 Concord Road (ca.1906), Fannie Morrison, who wanted a new brick façade (1914) on her father’s Wellesley Street summer place, now the Regis College president’s house, and Mrs. Elizabeth Sparhawk Sears, whose neoclassical house at 293 Boston Post Road (1919) is one of the few in Weston with two-story columns.

Mead’s house for Charles Richardson at 6 Conant Road (1900) was later enlarged and remodeled by Joseph Everett Chandler in 1917. Another of his gracious Colonial Revival homes, the George W. Eliot House at 96 Church Street (1910), has remained largely unchanged.

Mead designed the yellow brick barn at what is now known as the Case Estates, the first Weston High School (now Brook School Building A on Wellesley Street), and additions to the Dickson House at 125 Highland Street and the Williamson - Farlow house at 98 Love Lane. Mead also designed the Wayland Public Library.

Horace Sears Subdivision

The remaining 20 houses in the Pigeon Hill Area were built as part of the 1897 subdivision by estate owner Horace Sears, who that year purchased over 46 acres from Daniel Lamson, for $11,000. Sears, the bachelor son of First Parish Church minister Edward Hamilton Sears, had made his fortune as a textile manufacturer with the firm of N. Boynton and Company, which within a few years of the Pigeon Hill purchase would be re-organized as Wellington and Sears. Sears hired W. A. Mason and Son, a surveying firm based in Central Square, Cambridge, to lay out a road pattern which, with minor modifications, is the same today. The road curves around the base of the hill, rising gradually to the top.

This type of subdivision was not new in the United States. The first example, Riverside, Illinois, was laid out by Olmsted, Vaux and Co. nearly 30 years before, in 1869. According to Norman Newton’s book, "Design on the Land," Riverside was “the first clearly recorded instance in the United States of the application of landscape architectural design to a real-estate land subdivision project” (p.468). The Olmsted and Vaux plan for Riverside aimed at creating a “village-like suburb with a sylvan domestic atmosphere” (p.465). The curvilinear street pattern, so unusual in its day, was chosen for a purpose, as explained in Olmsted’s writing:

…as the ordinary directness of line in town-streets, with its resultant regularity of plan, would suggest eagerness to press forward, without looking to the right hand or the left, we should recommend the general adoption, in the design of your roads, of gracefully-curved lines, generous spaces, and the absence of sharp corners, the idea being to suggest and imply leisure, contemplativeness and happy tranquility" (as quoted in Newton, Design on the Land, p.467).

Development of Pigeon Hill

Adoption of Curvilinear Street Patterns

By the time of the Pigeon Hill subdivision, the curvilinear street pattern, which had been adopted by real estate developers in suburbs throughout the country, was finally making its way to Weston, albeit on a very small scale, as this rural, agricultural community began its transformation to sylvan suburb.

Alexander S. Jenney

Two of the first lots to be sold in the new development were the adjoining lots L and M at the top of the hill, sold to architect Alexander S. Jenney in November, 1897. Two years later, Jenney also bought Lot Q at the bottom of the hill from his house (now 32 Pigeon Hill Road), perhaps to protect his view. Jenney had began in practice in Boston about 1893 and worked in the firms of Fox, Jenney and Gale and later Jenney and Frost. He was the architect of the 1898 Weston Town Library and the fire stations on Boston Post Road (1914) and North Avenue (1908).

Jenney sited his own house at 44 Hill Top Road (1898, MHC 564, Map #12), on the crown of Pigeon Hill, where there was undoubtedly a spectacular view to the south in this era when so much land in Weston was deforested. In 1899, the house was valued at $6,000, with a henhouse valued at $200, according to town assessor’s records.

44 and 46 Hill Top Road

In 1899, Jenney also bought lot Q at what is now 32 Pigeon Hill Road at the base of the hill from his house. In 1901, his wife, Anne, died at age 37 of double pneumonia; and her two minor children, Paul G. and Marion S. Jenney, inherited the house. In 1919, Alexander Jenney and his children sold off the house at no. 44, which had been built on Lot M, but retained the adjoining vacant lot “L,” where they built a Tudor style house, now 46 Hill Top Road (1919, MHC 563, Map #11), which they sold seven years later, in 1926. It is not known that Jenney was the architect of either 44 or 46 Hill Top Road, but he is presumed to have designed them. Both houses have similar extra-large living room fireplaces.

21 Hill Top Road

Another of the first lots to be snapped up was Lot F, sold to Catherine Anne Everett of Philadelphia and her husband Herbert Everett in 1897. Everett built the carefully proportioned Colonial saltbox at 21 Hill Top Road (1898, MHC 560, Map #6), which first appears on town tax records in 1899, valued at $2,000.

42 Hill Top Road

In February and September, 1898, two adjoining hill top lots, P and N, were sold to Mary Q. Thorndike and her husband Albert, who worked for the Boston firm of Jackson & Curtis. The Thorndikes combined the two lots and built the house now numbered 42 Hill Top Road (1898-99, MHC 565, Map #14), which appears on the tax records in 1899, valued at $7,000 for the dwelling and $2000 for the barn. In 1900, Mary Q. Thorndike also bought Lot D down the hill from their residence, perhaps, like Jenney, to protect their view. The Thorndikes held this land, without building on it, until 1922, when they sold this parcel, later subdivided into two lots, now 7 Hill Top Road and 13 Pigeon Hill Road.

26 Pigeon Hill Road

The next house to be built, 26 Pigeon Hill Road (1899 -1900, MHC 568, Map #23), belonged to lawyer Grant Palmer and his wife Marian. According to the oral history account of his son, Grant, Jr., when Palmer and his wife were about to be married in 1891, they would take a horse and buggy and go from town to town to see where they would like to live. On one of these occasions they came to Weston and decided this was the place. They lived for a time in Robert Winsor’s mother’s house on Winsor Way (she used it only in the summer) and in other locations before buying their own lot in Horace Sears development in May, 1899. Grant Palmer took the nearby Central Massachusetts Railroad into his Boston office until he was about 90 years old.

20 Pigeon Hill Road

Another of the original buyers was Arthur J. Russell, son of First Parish Church minister Charles Russell and architect with the Boston firm of Brainerd, Leeds and Russell. Russell purchased Lot B in April, 1900 and constructed the Shingle Style house, presumably of his own design, now numbered 20 Pigeon Hill Road (1900, MHC 569, Map #24). Russell also designed other houses in Weston including the mansion for cotton broker Brenton H. Dickson Jr. at 125 Highland Street at the corner of Love Lane, built about the same time.

Charles H. Stimpson purchased Lot G in March, 1901 and by the time of the 1908 Middlesex County atlas, they had built a house on the site, now 25 Pigeon Hill Road. It is not clear whether the present house at this location was built then or in 1920. The adjacent house at 29 Hill Top Road was built in 1935 for Stimpson’s son, Charles Jr. and his wife Emily.

W. B. Clarkes' House

William Butler Clarke and his wife Maria Josephine bought Lot I on the Sears plan in 1902 and by 1904 had completed the house at 45 Hill Top Road (1903, MHC 562, Map #10). Clarke owned a bookselling business, W. B. Clarke, Co. on Tremont Street in Boston. His house has been attributed to both A.J. Russell and Samuel Mead, however, a photograph at SPNEA, donated by Wm. B. Clarke in 1922, is captioned “W. B. Clarkes’ house, Pigeon Hill, Weston, built about 1905, Planned by himself.” The photograph shows the original entrance porch, which was quite grand, with paired columns and a balustrade above. The house had large cupola/dormer at the peak of the low-hipped roof, suggesting a stylistic influence from the nearby Sears estate mansion, “Haliewa,” completed in 1902. In 1909, the Clarkes purchased the adjoining lot H and portions of lot G and J, including the cul de sac that had been marked “The Overlook” on the original street plan. With this sale, the Clarkes had enough land to build the combined cottage and garage, which still remains on the property (MHC 561, Map #9).

Pigeon Hill School

In 1903, Sears sold Lot C to fellow estate owner Robert Winsor as the site for his newly formed Pigeon Hill School. The school was established to educate the children of estate owners in Weston and Wayland; included among its students were the progeny of Winsor, Gen. Charles Jackson Paine and Brenton H. Dickson, Jr. The school’s location near the Weston stop on the Central Massachusetts railroad was important, as some of the children commuted to school from Wayland. In later years, the small site constrained the growth of the school, and Winsor arranged a move to land formerly part of his estate, where the school was renamed Meadowbrook. After the move, the former school building was converted to house, now 10 Pigeon Hill Road (1904, converted 1926, MHC 570, Map #25).

56 Pigeon Hill Road

About 1907, Weston doctor Frederick Hyde built his house at 56 Pigeon Hill Road (ca.1907, MHC 257, Map #17). Before moving to Pigeon Hill, Hyde had a house and office on Central Avenue (now Boston Post Road).

Harold Graves

It is worth noting that a fourth architect also lived on Pigeon Hill just outside the area covered by this form. Harold Graves built his own house at 23 Old Road about 1910. Graves was the architect of numerous houses in Weston, including 23 Wellesley Street and many houses in the Meadowbrook Road area. He converted the Winsor barn to the Weston Golf Club, although his design was much altered by a later fire. His house at 23 Old Road remained in the Graves family until recent years, when it was sold by the heirs of Graves’ daughter-in-law, Ida, and subsequently “modernized.”

13 Pigeon Hill

About a decade after the subdivision plan was drawn up, at the time of the 1908 Middlesex County Atlas, eight houses and one school building had been built on the reconfigured 17 lots of the Sears subdivision (21, 25, 42, 44 and 45 Hill Top Road, and 10, 20, 26 and 56 Pigeon Hill Road). Several notable houses were built in the next two decades, among them the house at 46 Hill Top Road (1919), already mentioned, and the house at 13 Pigeon Hill Road (ca.1925, MHC 557, Map #2), built on the extra lot originally owned by the Thorndikes.