The Boston and Worcester Railroad opened its Brookline branch from Brookline Junction to Brookline Village on April 10, 1848. The branch was extended west to Newton Upper Falls by the Charles River Branch Railroad in November 1852. The original wooden station at Brookline was replaced by a Victorian-style red brick station in 1878. The Boston and Albany Railroad, the successor to the Boston and Worcester, purchased the 1852-built extension in 1883 and extended it to its mainline at. The B&A began its Newton Circuit service over the Highland branch on May 16, 1886. All of the Highland branch stations except Brookline were replaced by stone structure designed by H.H. Richardson and Shepley, Rutan and Coolidge in the 1880s and 1890s.
The first horsecar line to reach Brookline Village was a branch of the Tremont Street line, which opened on October 26, 1859 from Roxbury Crossing to slightly northwest of Brookline Village along Washington Street. A branch from Brookline Village to Cypress Street on Pill Hill opened around 1888. Both lines were electrified on August 4, 1894. The Washington Street branch was extended to on September 1; this allowed through service from Reservoir, and – after August 1896 –. Two additional lines were added in July 1900: a branch on Harvard Street to began running on the Chestnut Hill tracks in May 1903. Even before the completion of the lines in 1900, the Boston Elevated Railway noted the need for improved transfer facilities in Brookline Village. Residents and local politicians petitioned for improved facilities in 1904 and 1908. A transfer station in the middle of the square was finally built in 1912 during road widening. It had two side platforms, with shelters similar to those at Coolidge Corner. By 1926, the transfer station served five main streetcar routes: Chestnut Hill– via Huntington Avenue, Cypress Street–Massachusetts via Ipswich Street, Lake Street–Brookline Village via Washington Street, Allston–Dudley, and the B&W. The Washington Street line was converted to bus in 1926. As construction of the Worcester Turnpike progressed eastward, the B&W was replaced by buses in June 1932, followed by the Chestnut Hill branch that November. The Ipswich Street line was cut back and mostly replaced by buses to in mid-1933. Cypress Street service was cut back to Brookline Village on June 10, 1934. The Allston–Dudley route was replaced by buses on September 10, 1938, with the Huntington Avenue cars cut back to short turns. The city immediately demolished the transfer station to speed traffic flow through the square.
In June 1957, the Massachusetts Legislature approved the purchase of the Highland branch by the M.T.A. from the nearly-bankrupt New York Central Railroad for conversion to a trolley line. Service ended on May 31, 1958. The line was quickly converted for trolley service, and the line including Brookline Village station reopened on July 4, 1959. The station building, like most on the line, was torn down during the conversion. The station has two side platforms serving the line's two tracks.
Renovations
In the early 2000s, the MBTA modified key surface stops with raised platforms for accessibility as part of the Light Rail Accessibility Program. Portable lifts were installed at Brookline Village around 2000 as a temporary measure, though it was not modified with raised platforms in 2002-03 as other stations were. During the Brookline Village/Longwood Avenue Station Renovation Project, the MBTA renovated Longwood and Brookline Village stations for accessibility. The two stations received raised platforms to interface with low-floor trams, wooden ramps to access high-floor trams, and other upgrades. Work on both stations began on July 23, 2007. Construction was completed in the second quarter of 2009, making Brookline Village a fully accessible station.