Chestnut Hill
Part of: Brighton
United States > Massachusetts > Greater Boston > City of Boston > Brighton > Chestnut Hill

Chestnut Hill is one of Greater Boston's most desirable – and complex – addresses. The enclave spans three cities, each in a different county: Brookline (Norfolk County), Boston (Suffolk County), and Newton (Middlesex County). The sections of Chestnut Hill within Boston are in Brighton and West Roxbury. Properties within the neighborhood typically have an 02467 zip code.

Just six miles west of downtown Boston, Chestnut Hill feels like a stately enclave that is also remarkably accessible to Boston on public transit. From the Reservoir stop on the Green Line (D), it is about 30 minutes to the Park Street station in downtown Boston.

Significant parkland. The neighborhood is anchored by the Chestnut Hill Reservoir, designed by Frederick Law Olmsted, who designed Boston's Emerald Necklace of parks, as well as Central Park and Prospect Park in New York City. The 114-acre Hammond Pond Reservation is a wooded reservation with a large, scenic pond located in the Newton section of Chestnut Hill. Hammond Pond offers fishing, hiking, and rock climbing. Kennard Park is a 16-acre park within a larger conservation area.

Academic presence – and pressure. Boston College acquired land in Chestnut Hill in 1907, when the area was still largely rural, and began construction on its distinctive Collegiate Gothic campus. The college has grown to 13,500 students, and its athletic programs, particularly football, exert continuing pressure on the adjacent residential neighborhoods. The campus extends into Brighton and Newton.

Boston marathon route and Heartbreak Hill. Sections of the Boston Marathon, including Heartbreak Hill, route go through the neighborhood. Heartbreak Hill is in the Newton section of Chestnut Hill, between the 20 and 21st mile markers for the marathon. While it only rises 88 feet, its location marking the last quarter of the race, is where many runners experience the phenomenon of 'hitting the wall'. Heartbreak Hill begins at Commonwealth and Grant avenues, and peaks at Commonwealth intersects with Hammond, Wachusett, and Woodchester streets.

While the area that would become Chestnut Hill was settled in 1655, it remained primarily rural until a handful of estates, the Essex Colony, were built in the 1800s. It evolved from summer estates into a somewhat more suburban neighborhood after the railroad arrived in 1886. However, many of the houses were designed by architects rather than developers. As a result, the houses are thoughtfully integrated into the topography, and the streets gracefully wind around rocky outcroppings of Roxbury puddingstone, rather than having blasted them away for straighter lines.

Chestnut Hill is an architecturally significant neighborhood, known for stately houses on large lots of land, affording considerably privacy and seclusion. The houses are typically Colonial Revival, Georgian Revival, Italianate, Shingle Style, and Tudor Revival. Within the Brookline section of the neighborhood, the areas south of Boylston Street are more highly developed and include more institutional uses. In addition, outside of the historic districts, there are a few areas – particularly around Boston College and along Route 9 – that are more densely developed with multifamily housing. Along Route 9 are many five story and higher condo complexes, as well as The Towers, two 16 story condo buildings near the Chestnut Hill mall.

Historic districts

Because of the significance of its landscape and architecture, parts of Chestnut Hill have been designated local and national historic districts.

Boston College Main Campus Historic District (Newton). In 1907, Boston College bought Lawrence farm among other parcels, when Chestnut Hill was still predominantly rural. The college's first building, Gasson Hall, was built largely of fieldstone found on the property. The heart of the campus was built in a distinctive Collegiate Gothic style.

Chestnut Hill Historic District (Brookline) is roughly bounded by Middlesex Rd., Reservoir Ln., Denny Rd., Boylston St. and Dunster Road.

Chestnut Hill North Local Historic District. (Brookline) While the National Register historic district was approved in 1986, in 2005 Brookline's Town Meeting approved a local historic district to offer greater protections. The local district includes 112 residential properties north of Boylston Street.

Chestnut Hill Reservoir Historic District (Boston) While most of Chestnut Hill remained farmland well into the early twentieth century, the area around the reservoir was developed in 1870, by landscape architect Frederick Law Olmsted, designer of Central Park in New York City and of the Emerald Necklace park system in Boston and Brookline.

Old Chestnut Hill Historic District (Newton) covers an area along Hammond St. and Chestnut Hill Rd. roughly bounded by Beacon St. and Essex Rd., and Suffolk Rd. In addition, the Chestnut Hill Local Historic District (Newton) was recognized in 2005 as a local historic district to add protections to the area already recognized by the National Register district.

Best blocks and notable buildings

Hammond House (9 Old Orchard Rd., Newton) is regarded as the oldest surviving house in Newton, from the family that first settled the area. Sources vary as to its age; it was built at least in 1714, but possibly as early as 1645.

400 Beacon Street, former and final residence of Mary Baker Eddy, now open as a house museum.

Jackson House (Chestnut Hill Rd.) was designed by one of the first women architects, Eleanor Raymond (1887-1989) in 1923. She is known for working with innovative materials, as well as designing one of the first successful solar-heated buildings in the northeast, the Sun House, in 1948.

Olmsted House (35 Glencoe Rd.) designed by Eleanor Raymond in 1937.

150 Woodland Rd. is one of the most expensive houses in Massachusetts. Built in 1999, the 26,000 sq.ft. house on almost 14 acres was recently asking $90 million.


The Brighton section of Chestnut Hill is served by several stops on the B train of the Green Line (South Street and Chestnut Hill Ave.), while the Newton section is served by the Chestnut Hill stop on the D train. The Brookline part of the neighborhood is served by the C train with stops at Reservoir and Cleveland Circle. The West Roxbury section of Chestnut Hill is close to the Belgrade Avenue stop on the Commuter Rail.


Chestnut Hill is not just a neighborhood within Boston. Instead, it is an overlay that covers sections of Boston, Brookline, and Newton. However, most properties within Chestnut Hill have an 02467 zip code.

Within Boston, sections of Chestnut Hill are in the Brighton and West Roxbury neighborhoods.

The Newton section of Chestnut Hill was settled by the Hammond family in 1655 – a prominent family remembered in the names of Hammond Street, Hammond Pond, and Hammond Woods. By the mid 1700s, the original landscape of meadows and wetlands had been converted to large farms and woodlots owned by a few prominent families. The neighborhood began in the same way as Longwood and Cottage Farm, as a place for friends and family of the original landowners. In this instance, Chestnut Hill was named by Francis Lee (who, as an aside, lived at 174 Beacon St. in Back Bay), who built his country house here in the 1850's. Given that his family was from Beverly, Mass., he attracted other North Shore families including the Cabots, Lawrences, Lowells, and Saltonstalls – and the area became known as the Essex Colony. Later, the Lawrence's farm became the heart of Boston College.

Despite being just six miles from downtown Boston, the area felt remote until the arrival of the railways in the 1850s. Because large parcels of land were sold and subdivided all at once, the neighborhoods of Chestnut Hill have a pleasing uniformity to them. Large, gracious homes were designed and built in the styles popular at the turn of the century, such as Colonial Revival, Tudor, and Shingle Style. They were then carefully sited on large lots that were heavily wooded. There is a continuity of styles, scale, setting, and materials amongst the homes that lends aesthetic cohesion to the neighborhood. The result is a pleasing balance between nature and the man-made environment.

In the early 1900s, Chestnut Hill changed dramatically as farmland was divided for estates and Boston College broke ground on their new campus. While the area continued to develop well into the 20th century, much of it still retains the rural neighborhood character established in the mid and late 19th century.

A Boston & Albany railroad station designed by H.H. Richardson replaced the original rail stop in 1884. Sadly, the station with its F. L. Olmsted designed landscaping, was demolished in the 1960's. The Boylston Street trolley line ran from Newton to Cypress Street and opened in 1900. Shortly after this, a small commercial area developed around the intersection of Heath and Hammond Streets. Commercial businesses still characterize this area today, and the Chestnut Hill Village Alliance, whose mission is to promote an accessible, livable and functional Chestnut Hill Village, hopes to build on this historic land development pattern.

Several talented and prolific architects first built their own homes and then designed homes for clients in this country enclave. Herbert Jaques, a partner in the firm of Andrews, Jaques, and Rantoul, built his home on Dunster Street. He then went on to design many Chestnut Hill homes, including the Cox estate on Heath Street, which was called "Roughwood" when built, and is now home to Pine Manor College. Jaques' home was recently demolished to make way for the new Longyear Museum. Architect Horace Frazer, partner in the firm Chapman and Frazer, built his own home at Heath and Boylston Streets. His firm built more homes in Brookline than any other architect, including two dozen Chestnut Hill homes built between 1890 and 1916. In addition to the skillful utilization of the era's prominent design styles, such as Tudor and Shingle, the architects excelled at coming up with seemingly infinite variations that gave each home its own unique signature. While the homes are large and gracious, they are not ostentatious, and have a minimum of ornament, possessing a straightforward understatement that seems a response to their environment. Many feature natural materials such as stone and wood shingles, and subdued earth colors are frequently employed.

Prominent landscape designers put their mark on the area as well, working on projects that sought to realize the latest trends and aesthetic ideals of their era. Holywood Cemetery, designed by Shedd & Edson civil engineers, embodied the romantic, rural cemetery in the mode of the revolutionary Mt. Auburn cemetery (1831). Frederick Law Olmsted developed a design for the Crafts Road neighborhood, however his plans were not used. Another desired landscape of the era was that of the golf course. The Chestnut Hill Golf Club and clubhouse were built in 1897, and were located where Fairway Road is today. The lands of the golf course were the last open lands developed in the area, which is reflected in the relative newness of the homes on Fairway and adjoining streets.