The particular character of Pill Hill derives from four significant factors. First, most of its development was carefully controlled by neighborhood residents. Second, its development and landscaping often reflected a respect for the local physical features. Third, many property owners hired well-established, respected architects and land-planners who created a visually harmonious neighborhood of distinguished houses. Fourth, and most important, occupying many of these homes during the nineteenth and twentieth centuries were leaders in politics, education, science, the arts, and, of course, medicine. The name Pill Hill derives from the many doctors who lived here beginning in the late nineteenth century and from the neighborhood’s Free Hospital for Women. As the alternate name, High Street Hill, could not have been used before 1860, it is not clear what the hill might have been called earlier. Old maps name most of Brookline’s hills, but not this one.
This map shows all roads and properties in 1822, Brookline. At the bottom middle is the meandering, then tidal, Muddy River (now approximately the Town Line). The straight, pre-1844 Brookline-Roxbury town line follows what is now mostly the rear lot lines on the west side of High St. The two closely paralleling roads angling away above that are Walnut St. and the 1808 Worcester Turnpike (Rte. 9). The first street crossing the turnpike is Cypress. The next one meeting it, where Walnut ends, is Warren St., with First Parish and (soon) the first Town Hall nearby. Note also that at that time Brookline’s boundaries went to the center of the Charles River and included what is now Kenmore Sq. The loss of those areas to Boston in the 1870s was a price Brookline paid for continued independence. (This map is one of a chronological set of six, the earliest of which is for 1667, created by the Brookline Historical Society in 1923. Most of those lot lines can still be traced in today’s highly subdivided Brookline.) In the late eighteenth century the Brookline portion of Pill Hill was still all in the Benjamin White estate to the south of Walnut St. and divided between the Edward White and Benjamin Davis estates to the north. The area east of what is now High St. was then part of Roxbury and remained essentially unsettled into the nineteenth century — by which time it was the Samuel Ward Farm.
By 1822 the White Estate south of Walnut had split onto the Oliver Whyte Estate to the east, the Rev. Henry Coleman estate to the west and, in the middle, the John Tappan (soon to be Samuel Philbrick) estate, which was approximately bounded by the present locations of Irving St. and the lower straight part of Walnut Place.
As late as 1874 the Philbrick and Wright (formerly Whyte) estates would still remain largely intact (although by then separated by Irving St.), while the Colman estate would become (from east to west): the properties along Walnut Place, developed starting in the 1840s and looking much today as it did then; the Cobb Estate, which later would become the Puddingstone Rows and Oakland Rd.; and what would become, in part, Wellington Terrace.
In size, these early nineteenth century estates were typical of the country properties of the first generation of wealthy retired merchants and carriage-commuters who settled in Brookline. Today we think of suburbs as developing on open farmland, but Brookline was different. In the mid-nineteenth century, when Brookline’s suburbanization and urbanization began, most of northern and central Brookline was compact country estates of perhaps five or ten acres, each with a substantial house and a few out-buildings. (For a time in the late nineteenth century, Brookline was said to be the wealthiest town in the country.) A critical difference between Pill Hill and many areas of Brookline is that, to a large extent, the land owners were their own developers and they intended to stay in the neighborhood. (The same might be also said of a few other Brookline areas, such as Longwood, Cottage Farm, and Fisher Hill.)
Wellington Terrace is the remaining core of the estate associated with the Joseph Sewall House (1823) at 2 Wellington Terrace, the second oldest house in Pill Hill — an estate that originally extended as far as Walnut Place. This granite residence contains elements of the Federal and Greek Revival styles, as seen in its long first floor windows. The porch or “piazza” was probably added in the 1840s or 1850s. The Rockport granite would have come all the way to Brookline by boat. Originally there were three similar granite houses of this time in Brookline. Only the two in Pill Hill survive. Granite was a rare, expensive material for a private house, when almost all non-urban buildings were of wood. The few stone buildings in Brookline were more typically made of local Roxbury puddingstone. The original owner of this house, Joseph Sewall, was a partner in the shipping firm of Sewall & Tappan and a descendant of Salem Witch Trial Judge Samuel Sewall. Joseph Sewall lived here until 1834.
As the estate was successively subdivided by later owners, the house became: a lodging house, a home for the orphans of naval officers, and since the 1970s, condominiums. The Stick Style house at 6 Wellington Terrace (1871) was originally built on what is now the rest of Wellington terrace, a lot that was separated from the Sewell house at that time. The house was later turned 90° when Wellington Terrace was laid out ca. 1890. The street was not named for the Iron Duke but for the Wellington family that sub-divided the property. Martha L. Wellington was also a member of the Swedenborgian church on High St. 3 Wellington Terrace (1892) combines the Queen Anne/Colonial Revival styles. 5 Wellington Terrace (c. 1892) is a simple Shingle Style house. 7 Wellington Terrace (1891) is a Queen Anne house designed by Edwin Tobey. Elizabeth Glendower Evans, an active social reformer lived here. Widowed at an early age, she contributed to the development of a more modern penal system in Massachusetts. She was active in the women’s trade union movement, eventually becoming a committed socialist, and supported the successful campaign for a minimum wage law in Massachusetts. Along with Jane Addams, she was a US delegate to the International Congress of Women in The Hague. She founded and funded the committee to defend Sacco and Vanzetti. Vanzetti’s letters refer to her as his second “Mother” and “Auntie Bee” — a name used by her friends — who included William James and Louis Brandeis. Other Pill Hill residents also actively supported Sacco and Vanzetti's cause.