House at 25 Stanton Road

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 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 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 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.

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 William F. Tuckerman House is a historic house located at 63 Harvard Avenue in Brookline, Massachusetts.

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.

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 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.

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.

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.

Brookline Village is one of the major commercial and retail centers of the town of Brookline, Massachusetts. Located just north of Massachusetts Route 9 and west of the Muddy River, it is the historic center of the town and includes its major civic buildings, including town hall and the public library. The commercial spine of the village, extending along Washington Street from Route 9 to the library, is a historic district listed on the National Register of Historic Places as the Brookline Village Commercial District.