Old Burying Ground (Brookline, Massachusetts)

The Brookline Town Green Historic District encompasses the historic colonial heart of the town of Brookline, Massachusetts. Centered on a stretch of Walnut Street between Warren and Chestnut Streets, this area is where the town's first colonial meeting house and cemetery were laid out, and was its center of civic life until the early 19th century. The district was listed on the National Register of Historic Places in 1980.

Maimonides School (Hebrew: ישיבת רמב"ם Yeshivat Rambam) is a coeducational, Modern Orthodox, Jewish day school located in Brookline, Massachusetts. The school was founded in 1937 by Rabbi Joseph Soloveitchik and his wife Tonya Soloveitchik. It is named after Rabbi Moses Maimonides. Today, Maimonides is a Torah institution with approximately 550 students from early childhood (2–4 years) through grade twelve with over 2,000 alumni, including multiple Rhodes Scholars, National Merit Scholars, prominent professors, scientists and business leaders. More than 325 of them are living in Israel.

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.

Frederick Law Olmsted National Historic Site is a United States National Historic Site located in Brookline, Massachusetts, a suburb of Boston. Frederick Law Olmsted (1822–1903) is recognized as the founder of American landscape architecture and the nation's foremost parkmaker of the 19th century. In 1883, Olmsted moved his home to suburban Boston and established "Fairsted", the world's first full-scale professional office for the practice of landscape design. Over the course of the next century, his sons and successors expanded and perpetuated Olmsted's design ideals, philosophy, and influence. The site is located at 99 Warren Street, in the Green Hill section of Brookline. Olmsted bought the Clark homestead, an 1810 Federal farmhouse, in 1883, to be near his frequent collaborator, H. H. Richardson, whose home and office were nearby. Olmsted and his son John Charles renovated the house, landscaped the property, and relocated the barn closer to the house, and in 1903 added the office wing to the northwest of the main house. Members of the Olmsted family occupied the main house until 1936, when Frederick Law Olmsted Jr. moved to Elkton, Maryland, renting the house to tenants. The offices of the Olmsted Brothers firm continued to be in the wing during this time, although business also declined. Members of the firm reoccupied the house in the 1960s, making substantial alterations to the original landscaping of the property. The property was acquired by the National Park Service in 1980. The grounds have been restored to a c. 1930 appearance, restoring much of Olmsted's landscaping.Park resources include the restored "Fairsted" historic landscape, and the design office (which remains virtually unchanged from the days when the Olmsted firm's activity was at its height.) Housed within the office complex are nearly 1,000,000 original design records detailing work on many of America's most treasured landscapes, including the grounds of the U. S. Capitol and White House; Great Smoky Mountains and Acadia National Parks; Yosemite Valley; New York's Central Park; and whole park systems in cities such as Buffalo, Seattle, Boston, Louisville and Montreal. The Olmsteds also played an influential role in the creation of the National Park Service, which now owns and maintains the Olmsted site. Frederick Law Olmsted National Historic Site is open to the public. The Park Service offers guided tours of the grounds and office wing.

Sargent's Pond is a man-made 3-acre (1.2 ha) pond on Sargent Road in Brookline, Massachusetts. The pond was created by Charles Sprague Sargent (best known as the first director of the Arnold Arboretum) in the late 1870s as a centerpiece of his family's extensive Holm Lea estate. Sargent's estate has since been subdivided, but the roads giving access to it run along the estate's original alignments. Sargent landscaped the estate using similar principles to those he applied at the Arboretum, with vistas and a variety of trees and shrubs. The pond was created by damming a brook. It still has naturalistic plantings around it, although some Sargent's rhododendrons (a significant draw on occasions when he opened the estate to the public) have died.The pond (along with its immediately surrounding grounds) was listed on the National Register of Historic Places in 1985.

Brookline High School is a four-year public high school in the town of Brookline, Massachusetts. It is a part of Public Schools of Brookline. The Headmaster is Anthony Meyer who holds a Master of Education in Teaching and Curriculum from Harvard Graduate School of Education and a Bachelor of Arts in English from Boston College.As of the 2021–22 school year, 2087 students were enrolled in the high school, served by 194.8 teachers (on an FTE basis), the student to teacher ratio was approximately 10.4 to 1. As of 2022, the enrolled student body race/ethnicity was self reported as 7.3% African American, 15.1% Asian, 12.7% Hispanic, 54.3% White, and 10.5% Multi-Race Non-Hispanic.All students at Brookline High School must complete three credits' worth of electives, with the intent of fostering student creativity. A newly opened film program, facilitated through Brookline Access Television (BATV), enables students to produce their own films with state-of-the-art technology.

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 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 Pill Hill Historic District is a historic district roughly bounded by Boylston Street, Pond Ave., and Acron, Oakland and Highland Roads in Brookline, Massachusetts.