Cypress–Emerson Historic District

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.

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.

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 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.

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.

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.

Saint Mary of the Assumption Church, Rectory, School and Convent is a historic church complex at 67 Harvard Street, and 3 and 5 Linden Place, in Brookline, Massachusetts in the Archdiocese of Boston. It was the first Roman Catholic Church in Brookline, and the first in the nation to bear the name. Most of its buildings were built between 1880 and 1906, and are reflective of the growth of the area's Irish immigrant community during that time. The complex was listed on the National Register of Historic Places in 1985.

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 Eliphalet Spurr House is a historic house located at 103 Walnut Street in Brookline, Massachusetts, United States.

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.