Brookline High School

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.

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.

Maimonides School (Hebrew: ישיבת רמב"ם Yeshivat Rambam) is a coeducational, Modern Orthodox, Jewish day school located in Brookline, Massachusetts. The school was founded in 1937 by Rabbi Joseph Soloveitchik and his wife Tonya Soloveitchik. It is named after Rabbi Moses Maimonides. Today, Maimonides is a Torah institution with approximately 550 students from early childhood (2–4 years) through grade twelve with over 2,000 alumni, including multiple Rhodes Scholars, National Merit Scholars, prominent professors, scientists and business leaders. More than 325 of them are living in Israel.

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.

89 Rawson Road and 86 Colbourne Crescent are two historic Shingle Style houses located in Brookline, Massachusetts.

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.

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

The Ritchie Building is a historic industrial building at 112 Cypress Street in Brookline, Massachusetts. Built in 1883 by Edward Samuel Ritchie, it is a fine example of the Panel Brick style, and is further notable as the factory space in which Ritchie manufactured a nationally distributed line of navigational instruments. The building was listed on the National Register of Historic Places in 1985.

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.

The houses at 76–96 Harvard Avenue are historic rowhouses in Brookline, Massachusetts. Built in 1903 by Benjamin Whitney, this was one of the earliest series of rowhouses to be built in Brookline. They are of Colonial Revival style, built in brick with limestone trim, with iron balconies. Originally built as single-family units, each of the houses except number 76 was converted to three apartments in the 1940s and 1950s.The rowhouses were listed on the National Register of Historic Places in 1985.

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.

Fairbanks Street station is a light rail stop on the MBTA Green Line C branch in Brookline, Massachusetts, located in the median of Beacon Street. Fairbanks station has two side platforms serving the line's two tracks. It is not accessible, although a wheelchair lift allows accessible transfer between the two elevations of the two halves of Beacon Street at the station. Track work in 2018–19, which included replacement of platform edges at several stops, triggered requirements for accessibility modifications at those stops. By December 2022, design for Fairbanks Street and seven other C Branch stations was 15% complete, with construction expected to take place in 2024.