Frederick Law Olmsted National Historic Site

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.

The Green Hill Historic District encompasses historical cross-section of residential housing in Brookline, Massachusetts, dating from the 18th century into the mid-20th century. The district includes properties on Warren, Cottage, and Fairmount Streets, and on Sargent Road, centered on the junction of Warren and Cottage Streets. The oldest houses (e.g. 215 Warren Street) date to the mid-18th century, and were originally modest Georgian or Federal structures. During the 19th century the area was populated by the summer estates of some of Boston's leading merchant and business families, including members of the Cabot and Perkins families. During the later 19th and early 20th centuries some of Brookline's largest and most architecturally interesting homes were built in this area.The district was listed on the National Register of Historic Places in 1985.

Reservoir Park is a historic park on Boylston Street in Brookline, Massachusetts. Its principal feature is Brookline Reservoir, formerly an element of the public water supply for neighboring Boston. The reservoir was built in 1848 as the main terminus of the now-defunct Cochituate Aqueduct, which delivered water from Lake Cochituate in the western suburbs. The reservoir covers 21.1 acres (8.5 ha), and is roughly kidney-shaped. A gravel path extends around the perimeter of the reservoir. The park is bounded on the north by Boylston Street (Massachusetts Route 9), on the west by Lee Street, on the south by Dudley Street, and on the east by Warren and Walnut Streets.There are two structures in the park. At the western end of the reservoir stands the Influent Gatehouse, the endpoint of the Cochituate Aqueduct. This is a modest utilitarian structure built out of dressed granite, about 11 feet (3.4 m) by 12 feet (3.7 m) and 11 feet in height. Its interior houses equipment for managing the flow of water from the aqueduct into the reservoir. The Principal Gatehouse, in contrast, is a more elaborate structure. It is located at the northeastern end of the reservoir, and is a two-story building partially buried in the embankment. It is built, like the Influent Gatehouse, of dressed granite, but was designed to be a public space. Its main facade has Renaissance Revival elements within a Greek-style temple front. The corners of the building have quoins in a paler shade of stone, and there is a course of that same stone in between the two floors. It has a gabled roof with a fully pedimented gable end, decorated with dentil stonework. The facade is three bays wide, with a centered entry on the lower level. The entry is recessed behind an arch that is flanked by round columns supporting an entablature. The entry is flanked by small elongated round-arch windows. The upper level consists of three larger equal-sized round-arch windows. The upper level of the building also has a facade facing the water; this also has three round-arch windows.Because the Principal Gatehouse was intended as a public space, its interior was also finished, unlike that of the Influent Gatehouse. The walls were plastered, and there were stairs, constructed of wrought iron, which were used to reach a platform giving a view of the water. These staircases are believed to the oldest surviving example of wrought iron stairs intended for public use in the United States. (They are predated by surviving stairs in lighthouses and a prison, and by public stairs in other countries.) The building's roof is also believed to be the only surviving period roof supported by wrought iron trusses.The park was listed on the National Register of Historic Places in 1985. The architectural significance of the gatehouse and its status as the best-preserved element of the Cochituate Aqueduct were recognized in its designation as a National Historic Landmark in 2015.

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.

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.

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 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.

Hellenic College Holy Cross Greek Orthodox School of Theology (HCHC) is an Orthodox Christian liberal arts college and seminary in Brookline, Massachusetts. Its mission is to educate individuals for life and service in the Orthodox Christian community; this includes men preparing for the priesthood of the Greek Orthodox Archdiocese and other Orthodox Christian entities, as well as men and women for leadership roles in the church or within secular society. HCHC includes a graduate school of theology (seminary) for clerical training and education, and several undergraduate and certificate programs in business, education, literature, and other secular professions. The institution was founded in 1937 as Holy Cross Theological School in Pomfret, Connecticut, but was moved to Brookline, Massachusetts in 1947.

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 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 Park School is an independent day school in Brookline, Massachusetts, for boys and girls providing pre-Kindergarten through eighth grade education. Founded in 1888 as Miss Pierce's School, it is a 34-acre campus in Brookline, Massachusetts near Jamaica Pond.

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.