High Street Hill

High Street Hill Association  (HSHA)

The HSHA was organized over fifty years ago by a group of neighbors living on or around High Street and the Village Green.  Residents came together on January 27, 1958 to form the HSHA because of concerns that development was threatening to alter the character of the community. The neighborhood decided “to organize an association to foster and promote the common interests of the residents, property owners and others interested in the welfare of the High Street area.”  The HSHA is one of the older continuously operating neighborhood associations in Brookline.

The High Street Hill neighborhood has played an important role in the history of the town. Walnut Street, one of the neighborhoods’ major roads, was a major east-west thoroughfare in 18th century Brookline.  The eastern part became part of Brookline in 1844.  In the middle of the 19th century, the town’s civic center moved from the intersection of Walnut and Warren Streets to Brookline Village, a branch of the Boston-Worcester railroad came to Brookline Village, and our neighborhood blossomed.

Originally known as High Street Hill, the area was nicknamed Pill Hill in the late nineteenth century because of the large number of medical professionals who lived here. Set above the Village, the neighborhood is particularly distinguished by the numerous examples of Victorian architecture. There is an underlying harmony of size and scale as well as a consistency of good design and workmanship.

In 1977, most of Pill Hill was placed on the National Register of Historic Places.   Later, the Pill Hill Local Historic District was established with the help and support of the HSHA. The current boundaries of the HSHA, roughly Walnut Street, Allerton, Pond Avenue, and Cypress Street, are the same as those of the Local Historic District.

Over the past 50 years, the HSHA has worked to promote a sense of neighborhood and has been an advocate for the interests of its residents on a wide array of issues. We advocated for the construction of a new Lincoln school, and we supported the conversion of the Free Hospital for Women into The Park condominiums.  Our neighborhood is greener because of the restoration initiatives for the Emerald Necklace and Olmsted Park and Friends of Leverett Pond, all supported by the HSHA.

The High Street Hill Association continues to foster our sense of community and tries to preserve its unique characteristics.  We are lucky to live in such an extraordinary and historic community.

High Street Hill Association Board Officers

  • Diana Post President 76 High St 617-738-5096 dpost@partners.org
  • Anthony Flint Vice President 254 Walnut St 617-383-5601 anthony.flint@gmail.com
  • John Carpenter Secretary 68 High St 617-566-0689 j.m.carpenter@sbcglobal.net
  • Kristin Leader Treasurer 141 Walnut St 617-734-1964 kkleader@comcast.net

Images of High Street Hill

The Tappan-Philbrick house in the mid-nineteenth century with cows in the yard.






The Swedenborgian church in 1876 









44 Edgehill Road.  Built 1877, Peabody and Stearns, Arch