Ritchie Building

Brookline Hills station is a light rail station on the Massachusetts Bay Transportation Authority (MBTA) Green Line D branch in the Brookline Hills neighborhood of Brookline, Massachusetts. The station has two side platforms serving the line's two tracks. It was closed from April 2021 to January 2022 as part of adjacent construction on a Brookline High School building, which included renovations to make the station accessible.

105 Marion Street is a historic house located in Brookline, Massachusetts. It is significant as a well-preserved local example of the Second Empire style of architecture.

The House at 5 Lincoln Road in Brookline, Massachusetts, is a well-preserved local example of Italianate architecture. This 2+1⁄2-story wood-frame house was probably built in 1852 by Samuel Crafts, around the same time he built the nearby House at 25 Stanton Road. The two houses were essentially identical in their original construction; 25 Stanton underwent some modification in the 1870s. This house exhibits classical Italianiate styling, including deep bracketed eaves, and round-arch windows in the gables, as well as heavy cornices over the windows.The house was listed on the National Register of Historic Places in 1985.

The House at 44 Stanton Road in Brookline, Massachusetts, is a well-preserved local example of Italianate architecture, and is one of four houses of that style on Stanton Road. The 2+1⁄2-story wood-frame house was built c. 1864–65 by James Edmonds. It has deep eaves with paired brackets, a small centered gable on the front facade, and bracketed windows. Its full height front porch is probably a later addition. It was moved a short distance to its present location in 1901.The house was listed on the National Register of Historic Places in 1985.

25 Stanton Road is a historic house located in Brookline, Massachusetts, and is a well-preserved local example of Italianate design.

The Robert S. Davis House is a historic house at 50 Stanton Road in Brookline, Massachusetts. Built about 1859 for the scion of a locally prominent family, it is one of the town's best-preserved examples of Italianate architecture. It was listed on the National Register of Historic Places in 1985.

The Cypress–Emerson Historic District encompasses a residential area on the west side of Brookline Village in Brookline, Massachusetts, United States. Centered on Waverly and Cypress Streets, and including Emerson Park, this area was developed in the post-Civil War era, its growth matching that of the commercial areas of the village. The district was listed on the National Register of Historic Places in 1985.

Brookline is a town in Norfolk County, Massachusetts, United States, and part of the Boston metropolitan area. Brookline borders six of Boston's neighborhoods: Brighton, Allston, Fenway–Kenmore, Mission Hill, Jamaica Plain, and West Roxbury. The city of Newton lies to the west of Brookline. Brookline was first settled in 1638 as a hamlet in Boston, known as Muddy River; it was incorporated as a separate town in 1705. At the time of the 2020 census, the population of the town was 63,191. It has been the most populous municipality in Massachusetts to have a town (rather than city) form of government since Framingham changed to a city in 2018, following a 2017 referendum.

The Old Burying Ground, also known as Walnut Street Cemetery, was the first cemetery established in Brookline, Massachusetts, in 1717. It was the town's only cemetery for 140 years until the establishment of the Holyhood Cemetery in 1857, and the Walnut Hills Cemetery in 1875. The cemetery is part of the Brookline Town Green Historic District.

Staley School of the Spoken Word also known as "Staley School of Oratory", "Staley School", or "Staley College", was a college in Brookline, Massachusetts, founded by Dr. Delbert Moyer Staley, that closed in 1957. Originally named College of the Spoken Word, it opened in 1905 on Huntington Avenue in Boston; by 1920, the school had relocated to Brookline and was located at Washington Street and Cypress Street. As of 1992, their charter was held by Boston College.Many aspiring leaders and politicians came to the school, largely to polish their presence and presentation. The majority had already earned college degrees, some from institutions such as Harvard University. One famous Harvard alumnus to be graduated from Staley was future president John F. Kennedy.

The Candler Cottage is a historic house at 447 Washington Street in Brookline, Massachusetts. Built about 1850, it is one of the town's few examples of Gothic Revival architecture. It was listed on the National Register of Historic Places in 1985.

Brookline High School is a four-year public high school in the town of Brookline, Massachusetts. It is a part of Public Schools of Brookline. The Headmaster is Anthony Meyer who holds a Master of Education in Teaching and Curriculum from Harvard Graduate School of Education and a Bachelor of Arts in English from Boston College.As of the 2021–22 school year, 2087 students were enrolled in the high school, served by 194.8 teachers (on an FTE basis), the student to teacher ratio was approximately 10.4 to 1. As of 2022, the enrolled student body race/ethnicity was self reported as 7.3% African American, 15.1% Asian, 12.7% Hispanic, 54.3% White, and 10.5% Multi-Race Non-Hispanic.All students at Brookline High School must complete three credits' worth of electives, with the intent of fostering student creativity. A newly opened film program, facilitated through Brookline Access Television (BATV), enables students to produce their own films with state-of-the-art technology.