House at 83 Penniman Place

Reservoir station is a light rail station on the MBTA Green Line D branch, located in Brookline, Massachusetts near Cleveland Circle and the south edge of Brighton. The station is adjacent to Reservoir Yard and Carhouse, with the Cleveland Circle terminus of the C branch just a block away. With a daily ridership of 3,395, Reservoir is the second-busiest surface stop on the D branch (after Brookline Village).Reservoir station is accessible, with raised platforms to accommodate low-floor trams. MBTA bus routes 51 and 86 terminate at the Reservoir busway off Chestnut Hill Avenue.

155 Reservoir Road is a historic house located in Brookline, Massachusetts. It is significant as a well-preserved Greek Revival house.

Cleveland Circle is a surface light rail station on the MBTA Green Line C branch, located in the Brighton neighborhood of Boston, at Cleveland Circle. Cleveland Circle station is handicapped accessible, with raised platforms to accommodate low-floor trams.

The Strathmore Road Historic District is a residential historic district on Strathmore Road and Clinton Path in Brookline, Massachusetts. It consists of six brick apartment blocks, four of which lie on Strathmore Road, and two of which lie on Clinton Path. The two streets form a loop just south of the westernmost portion (in Brookline) of Beacon Street, and abutting the MBTA Green Line yard at Cleveland Circle. The district is reflective of the area's growth as a commuter suburb following the development of the rail line along Beacon Street (now the MBTA Green Line "C" branch), and was listed on the National Register of Historic Places in 1985.Beacon Street and the rail line were extended to Cleveland Circle in the 1880s, and the area was soon developed to provide housing for commuters into Boston. Charles Newhall and George Johnston were two major developers whose projects line Beacon Street, and who were responsible for the development of Strathmore Road as well. This development took place between 1904 and 1908. The buildings are 3-1/2 story brick buildings, most designed by either James Hutchinson or Murdock Boyle. Five of the six buildings were built by Johnston; only 1 Clinton Path was built by Newhall. They are built with consistent setbacks, large enough to provide each building with a small front yard, and with sufficient space to allow for the planting of trees.The basic styling of most of the buildings is either Federal or Classical Revival. Typical features include limestone wedges above the windows, and cornices with dentil molding and modillions. Two of the buildings (40 Strathmore and 1 Clinton) are Romanesque in style, using rusticated brownstone and with round-arched entries.

Cleveland Circle, an area of Boston, Massachusetts, is located in Boston's Brighton neighborhood, and more specifically the Aberdeen section of Brighton, in very close proximity to Brookline and Chestnut Hill, Massachusetts, at the intersection of Beacon Street and Chestnut Hill Avenue. Cleveland Circle is the commercial "town center" of Aberdeen, a residential area of apartment buildings and free-standing homes, populated primarily by working professionals of all ages, as well as seniors. The area also has student rentals inhabited primarily by students from nearby Boston College, but nevertheless, student renters are the smallest segment of the area's population. This part of Brighton is a historical streetcar suburb. The Cleveland Circle station is the terminus of the Green Line C branch of the MBTA's Green Line. Reservoir station on the Green Line D branch is one block to the south. Chestnut Hill Avenue on the Green Line B branch is a short walk away.

Kilsyth Terrace is a historic series of townhouses at 15–27 Kilsyth Road in Brookline, Massachusetts. The Chateau-style townhouses were designed by J. Williams Beal and built in 1892. They are 3+1⁄2-story townhouses, built of yellow brick with Roxbury stone trim. Notable features include turrets, arched entrances and corbelled brickwork. Their design was likely influenced by the earlier Beaconsfield Terraces development, not far away on Beacon and Tappan Streets.The building was listed on the National Register of Historic Places in 1985.

The Fisher Hill Reservoir and Gatehouse are historic elements of the public water supply for the Greater Boston area.

Cardinal Cushing College was a private, Catholic women's college in Brookline, Massachusetts. It operated from 1952 to 1972 and was named after Cardinal Richard Cushing, who helped acquire the land for its campus while he was Archbishop of Boston. Cardinal Cushing College was one of three now-defunct women's colleges sponsored by the Sisters of the Holy Cross, along with College of Saint Mary-of-the-Wasatch in Salt Lake City and Dunbarton College of Holy Cross in Washington, D.C. The college's campus is now owned by Newbury College. Newbury College closed in 2019. Its records are held in the Sisters of the Holy Cross Archives at Saint Mary's College in Notre Dame, Indiana.

Newbury College was a private college in Brookline, Massachusetts, originally founded in 1962.The college was accredited by the New England Association of Schools and Colleges (NEASC) but was placed on probation in June 2018, when its worsening financial standing was determined to pose a potential violation of NEASC's accreditation requirements. In December 2018, the college announced that it would close at the end of the 2018–19 academic year.Lasell University was named as Newbury's institution of record and provides enrollment verifications and copies of transcripts for Newbury students, though Lasell does not possess archival material from Newbury.

Englewood Avenue station is a light rail station on the MBTA Green Line C branch located in the median of Beacon Street just west of Englewood Avenue in Brookline, Massachusetts. The station consists of two low side platforms which serve the C branch's two tracks. Englewood Avenue is not accessible. Track work in 2018–19, which included replacement of platform edges at several stops, triggered requirements for accessibility modifications at those stops. By December 2022, design for Englewood Avenue and seven other C Branch stations was 15% complete, with construction expected to take place in 2024.

The Fisher Hill Historic District encompasses a residential area in central Brookline, Massachusetts. The area was subdivided and built out beginning in the 1880s, with landscaping design by Frederick Law Olmsted and John Charles Olmsted. The district is bounded on the west by Chestnut Hill Avenue, Baxter Road, and Channing Road, and on the south by Massachusetts Route 9. Its eastern boundary runs along Buckminster Street to Dean Road, joining the northern boundary of Clinton Road, running between Dean Road and Chestnut Hill Avenue. Prior to its development in the 1880s, Fisher Hill had a relatively small number of landowners. Some of them banded together, hiring the Olmsteds to design a subdivision plan for the entire district. Lots were sold to wealthy individuals, who built fashionable houses, often designed by architects. In 1914 a restrictive covenant was entered into by a significant number of property owners, restricting their properties to strictly single-family residential uses.The district was listed on the National Register of Historic Places in 1985.

The Waterworks Museum is a museum in the Chestnut Hill Waterworks building, originally a high-service pumping station of the Boston Metropolitan Waterworks. It contains well-preserved mechanical engineering devices in a Richardsonian Romanesque building.During its busiest years, the waterworks pumped as much as a hundred million gallons of water each day.: 125  The station was decommissioned in the 1970s, and later some of its buildings were turned into condominiums. After a period of disuse, the pumping station was restored, and in 2007 the Waterworks Preservation Trust was set up to oversee its conversion into a museum. In March 2011, the building reopened to the public as the Waterworks Museum.