House at 105 Marion Street

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.

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 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 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 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.

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.

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.

The Dr. Tappan Eustis Francis House is a historic house at 35 Davis Avenue in Brookline, Massachusetts. Built in 1877–78, the 2+1⁄2-story house is a well-preserved rendering of Queen Anne styling in brick. Its roof has varying patterns of slate tiles, and the facade has a variety of brickwork decorations. Its chimneys feature Panel brick design elements, and it has a Stick style porch. The house was built for a doctor who served the town for 50 years. The house was listed on the National Register of Historic Places in 1985.

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.