Houses at 76–96 Harvard Avenue

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

St. Mark's Methodist Church is a historic church building at 90 Park Street in Brookline, Massachusetts. The church cornerstone was laid on April 9, 1892. The building was designed by Brookline architect George A. Clough in a Romanesque style. The building, vacated by its dwindling congregation in 1968, was listed on the National Register of Historic Places in 1976. It has since been converted into condominiums.

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

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 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 12 Vernon Street in Brookline, Massachusetts is one of the town's most elaborate Queen Anne Victorians. The 2+1⁄2-story wood-frame house was designed by Tristram Griffin and built in 1890 for William Boynton, a Boston flour merchant. It has classic Queen Anne elements, including a turret, multiple projecting and recessed sections. Its front porch wraps around the turret to the side, supported by paired columns above a spindled balustrade, and features a gable above the entry stairs decorated with latticework and arched spindlework framing the opening.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.

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.

Summit Avenue station (announced as Winchester Street/Summit Avenue) is a light rail stop on the MBTA Green Line C branch, located in the median of Beacon Street between Winchester Street and Summit Avenue in the Coolidge Corner neighborhood of Brookline, Massachusetts. The stop has two low side platforms that serve the line's two tracks; it is not accessible.

Brandon Hall station is a light rail stop on the MBTA Green Line C branch in Brookline, Massachusetts. The station's name is an anachronism, as it was named for Brandon Hall, a large hotel built in 1904 just south of the station which burned down on April 26, 1946, after housing 400 SPARS during World War II.Brandon Hall station has two side platforms serving the line's two tracks. It is not accessible, although a wheelchair lift allows accessible passage between the two elevations of the two halves of Beacon Street at the station. With 356 daily passengers by a 2011 count, Brandon Hall was the second-least-used stop on the C branch after Hawes Street.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 Brandon Hall and seven other C Branch stations was 15% complete, with construction expected to take place in 2024.

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.