William F. Tuckerman House

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 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 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.

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.

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 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 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.

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.

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.