By the beginning of World War I all that remained undeveloped of the Brookline Land Company holdings — by then owned by the Brookline Riverdale Land Association — was the southern ends of Glen Rd, Pond Ave., and Hawthorn Rd. When a developer took out permits for a series of triple-deckers at the bottom of Cumberland, neighbors formed the Glen Trust and bought the land to assure that the character of the Hill would be maintained. Many homes on these streets were developed by individual residents who bought lots. The majority are of the Colonial and Dutch Colonial styles, and many have the sunporches and sleeping porches typical of this period. At 203-219 Pond Ave. are the four Playing Card Houses (1925-26) — although designed by three different architects, each house has shutter cut-outs of one of the four suits in a deck of cards.
Unique among Pill Hill’s houses is 231 Pond (1928), designed by Byron Merrill, whose highly picturesque materials — the random red and black clay roof tiles and the overfired, distorted clunker-brick — are typical of a very theatrical (or movie-set like) architecture which flourished in the interwar period. Some think of this as a “storybook” house with a somewhat Scandinavian character — albeit perhaps more Brother Grimm than Hans Christian Andersen. Its distorted bricks, a type which originally must have been discovered among over-fired kiln rejects, were rather popular in and peculiar to Boston in this period — and clearly came to be deliberately produced. After World War II the Scandinavian-modernist architects Alvar Aalto and Earo Saarinen, teaching and working at MIT, discovered and used them, leading to a brief fad for them outside New England in the 1960s.
Howe, Manning & Almay designed the Colonial Revival house at 60 High (1928), for William C. Codman. Lois Lilley Howe and Eleanor Manning O’Connor were among the first women graduates of the M.I.T. School of Architecture. Their firm was the first all-woman architecture practice in Boston and the second in the U.S. They built over thirty houses in Cambridge and public housing in Boston. Howe was the first woman elected a Fellow of the American Institute of Architects.
A Pill Hill institution is the clay tennis court at the corner of Hawthorne and Cumberland. By 1893, far earlier than for much of that area, there was already a house on that lot, owned by E.W. Lamb. By 1907 the house had been replaced by a carriage house or “barn”, designed by Peabody & Stearns, and still owned by Lamb. Curiously, the barn (as shown on town atlases) appeared to have the same footprint as the house, but was located further up the Cumberland side of the lot. In the 1920s it belonged to Mrs. Redmond, who lived at 70 Upland. Mrs. Redmond, whose daughter was an accomplished equestrian, kept a horse in her Cumberland Rd., barn. It was also rumored, perhaps apocryphally, to have been a Prohibition era depository of bootlegged hooch. In 1930 she sold the lot for $10,500 to The Hawthorne Associates Trust. By then the tennis court was already in place. The Trust’s shareholders were a broad group of neighbors who may have been more concerned about inappropriate development than about tennis. At that time and for some years thereafter the barn was used to store stage scenery for the Leland Powers School of the Spoken Word and to garage automobiles. The tennis court was leased to an informal neighborhood club. Sometime in the 1940s the trust considered subdividing the lot and selling the part with the barn, which has been recalled as being built of brick and stone, for conversion into a house. However a zoning change precluded that. In the mid-50s the barn was demolished. At some point the Trust took over the role of the tennis club. It also gradually gained control of a majority of the shares, although some are still handed down from owner to owner when houses are sold. Anyone living in the neighborhood can be a playing member of the club.
The Brookline Land Company area in 1913, showing its final street pattern. No houses had then been built on Glen or Pond Roads. The Highland Circle housing was a year from being started. A carriage barn occupied the now wooded half of the tennis court’s lot on Cumberland Ave at Hawthorne Rd. The new Acron Rd on the Wright estate (then still a dead end called Acron Place) had nothing built on it, nor even at that late date, did the entire Walnut St. frontage of the Wright Estate. Near the upper left corner of the map are the trolley car storage tracks and “car-barns” off Cypress St. at the end of the trolly line, where the Robinson Playground is now.
Pill Hill in 1930. The white road on the upper left is Boylston. Almost paralleling it, Walnut, meets High at the “V” shaped building. Top right is Leverett Pond. Just below that is the Free Hospital for Women and below that Tech Field. Along the bottom edge is Cypress with the huge black-roofed trolley car barn where the playing field is now. The now lost carriage house is visibly next to the (very white) tennis court on Cumberland. The Allerton Hospital stands opposite the north end of Glen, whose southern end goes through to Highland. Hall Road is still a garden. One estate occupies all the land between the Puddingstone Rows and Walnut Place. The Veterans Housing and 99 High are not built.
The only post-World War II house in this part of Pill Hill is a 1960s split-level at 38 Cumberland, once the home of Seiji Ozawa, long time conductor of the Boston Symphony Orchestra. It has a Japanese garden designed by Julie Messervy.
At the bottom of High St. around Highland Circle, are four identical brick double houses with gambrel roofs designed in 1914 by Kilham & Hopkins for the Highland Road Trust. (The shingled, single-family houses between them were inserted in the 1920s.) Prescott Hall of 127 High St and Henry Lamb of 138 High were two of the trustees. There was a strong anti-triple decker sentiment at the time and these houses reflect the housing reform ideas of the Massachusetts Homestead Commission. The purpose of the Commission was to “assist mechanics, laborers, and other to acquire homesteads or smaller houses and plots of ground in the suburbs of cities and towns.” They were inspired by the examples of the English “Garden Cities” around London. Kilham & Hopkins were chosen because of their experience in designing similar housing in Lowell and Salem. Among the early residents were teachers, a chauffeur, a bookkeeper, a carpenter, and a civil engineer. Nearby, in the Point neighborhood, other reform housing was built at about that time by the Lawrence Trust. Some of it survived intact and in good condition until recently when, unfortunately, it was vinyl-sided. The strength of the anti-triple decker sentiment that developed throughout New England in that era was such that, when zoning was introduced after World War I, almost everywhere triple-deckers were not allowed. (In part this arose from concerns about urban conflagrations, such as the great Salem fire of 1914, although there may have been other biases at work as well.) Even though they are now considered a desirable type of housing, it was only in 2007 that Brookline, for the first time, created an appropriate three-unit zoning classification.
Elsewhere on the Hill changing times changed the neighborhood. After World War I the Wright Estate house was demolished and the land subdivided into lots for two family houses and triple-deckers along its Walnut St. and new Acron Rd. frontages. With the Great Depression came the downsizing or demolition of two other houses at the foot of Walnut Place and at the corner of Irving and Upland — in the latter case creating two cottages, which for the past sixty years have often served as dower or retirement homes for neighbors no longer needing large houses.
Sometimes we pass historic clues and place markers daily without a second thought. Pill Hill has a surprising number of substantial granite Obelisk-like stone posts marking the entrances to former estate drives and developments with estate ambitions — including Wellington Terrace, Walnut Place, both ends of lower Upland Rd. (Harvey Ave., as it then was), the Tappan-Philbrick house, a massive pair for the Moses Williams house (67 Walnut Place), and the houses at 217, 233, and 239 Walnut and at 55 Irving (originally a drive to 99 High), and two pairs marking the site of the Searle Estate near the bottom of Walnut Place.
As the ‘thirties came to a close Pill Hill, like the rest of Brookline, saw its old hand painted wood street name signs replaced by unique cast aluminum ones made in the Town’s own foundry in the Town Barn on Cypress St. (Many still survive in the Town’s Historic Districts whereas they have almost completely disappeared from south Brookline. There is no other set of surviving cast aluminum street name signs like these in the country. (Brookline still has several hundred in place and they have been determined to be eligible for listing in the National Historic Register.)
Post-World War II
After the Depression, World War II and the introduction of cheap GI mortgages for suburban tract houses, areas like Pill Hill were thought obsolete and its large houses were called “white elephants” or “Victorian horrors” (think Charles Addams). In the 1960s urban renewal came to Brookline with a vengeance. The Brookline Redevelopment Authority efficiently cleared the Marsh and the Farm and, following Federal “mandates,” declared Brookline Village and Pill Hill “blighted.” Into the late 1970s Pill Hill residents could be eligible for low interest Federal improvement loans. Houses on the Hill were attractive to some with large families because they were cheap — but brokers told their clients to avoid the Lincoln School. (Transfers to other schools allowed, no questions asked!) Break-ins and vandalism were not uncommon. One Upland Rd. house was a Hippie Commune. Another Upland owner reluctantly demolished a polygonal Victorian greenhouse because its glass was constantly being broken.
In 1958 a group of Pill Hill neighbors formed the High Street Hill Neighborhood Association with Jay O’Callahan’s father, Edward O’Callahan, as its first president and with bylaws cribbed by judge Mo Richardson from the Beacon Hill Neighborhood Association. It now claims the distinction of being Brookline’s oldest continuously operating neighborhood association.
This large Queen Anne house at the corner of Upland and Irving was built by Dr. George Sabine in about 1880. It was demolished at the end of the Depression and replaced by the two cottages at 30 Irving and 27 Upland. While the house is gone, the granite obelisk-like post (visible lower left) at the corner of the street remains — one of two pairs still marking the ends of what was once Harvey St. on the Wright Estate (now lower Upland Rd.).
True to the neighborhood’s heritage, many long time residents remained, and Pill Hill attracted new residents who understood how special it was and wanted to retain its unique character. Although the Town’s first Local Historic District was created in Cottage Farm, following a weekend demolition by B.U., Pill Hill provided about a third of the combined members of the then Historic and Local District Commissions, just as it has always provided more than its share of the present Preservation Commission’s members. Most of Pill Hill was placed on the National Register of Historic Places in 1977. The Local Historic District was established in 1983 following various threats, including a proposal to demolish and sub-divide the Tappan-Philbrick estate on Walnut St. and the insensitive aluminum siding of some properties.
Based on the experience of similar Brookline neighborhoods, if there had been no historic district, in recent years Pill Hill probably would have again experienced the demolition of larger houses — but now for McMansions — and of smaller homes for two-families or higher density development, where the zoning allows.
The brick and shingle new Park Condominiums (1984) at the southern end of the former Free Hospital site, designed by CBT/Childs, Bertram, Tseckares & Casendino, was the first new building in the Pill Hill subject to Historic District design review. Since then there have been three new houses, a few out buildings and many additions throughout the neighborhood.
The new buildings or major additions that the Preservation Commission has reviewed in the Pill Hill District include:
The Latvian Churchentrance lobby addition (1985), which replaced the original front of the meeting hall (previously identical to the façade still exposed on High St.) The design, while not impressive, was much improved over the then existing façade and the original proposal — and it was required not to be in physical contact with the historic church structure.
An Acorn (prefabricated) house at 222 Walnut St. (1985). Because this industrially produced house fit appropriately among its 1950s modern neighbors, it was approved as presented.
A new house at 10 Walnut Place (1997), whose design responded to neighborhood concerns about sight lines and not upstaging the Tappan-Philbrick house.
A new house at 36 Allerton, (2005), whose siting on the lot evolved in response to neighbors’ concerns about preserving a specimen beech tree on the property.
A two story garage with studio above at 273 Walnut (1997), a garage/woodworking studio at 27 Walnut Place (1999), and the Parking forecourt for one of the Puddingstone Rows at 254-58 Walnut St. (1994).