Roughwood (Brookline, Massachusetts)

Pine Manor College (PMC) was a private college in Chestnut Hill, Massachusetts. It was founded in 1911 and was historically a women's college until 2014. Originally the college was a post-graduate program of Dana Hall School, an all-girls preparatory high school, although later on it was an independent college serving primarily students of color. In May 2020, with the institution's longterm financial instability exacerbated by the COVID-19 pandemic, Boston College announced that it would take over the college, in a graduated scheme that allowed outgoing Pine Manor students to study on their campus through the 2022 school year.

The Paine Estate is a historic estate at 325 Heath Street in Brookline, Massachusetts. The mansion on the expansive estate was built by Walter Channing Cabot for his daughter Ruth and son-in-law Robert Treat Paine, Jr. It is a Jacobethan style Medieval Revival structure built of brick, with Flemish end gables, limestone sills and lintels, and egg-and-dart panels. It is one of the last estates, of what was once a whole series, which lined Heath Streat. The only other to remain (albeit no longer in private hands) is Roughwood, now the campus of Pine Manor College. The property was listed on the National Register of Historic Places in 1985.

Beaver Country Day School is an independent, college-preparatory day school for students in grades 6 through 12 founded in 1920. The school is located on a 17-acre (69,000 m2) campus in the village of Chestnut Hill, Massachusetts, near Boston. Beaver is a member of the Cum Laude Society, the Independent Curriculum Group, and the National Association of Independent Schools. Beaver is accredited by the New England Association of Schools.

The Chestnut Hill Historic District encompasses the historic portion of the village of Chestnut Hill that lies in Brookline, Massachusetts, with only slight overlap into adjacent Newton. The 70-acre (28 ha) district is bounded on the north by Middlesex Road, on the east by Reservoir Lane, on the south by Crafts Road and Massachusetts Route 9, and on the west by Dunster Road. A small portion of the district extends south of Route 9, including a few houses and the Baldwin School on Heath Street. The district was listed on the National Register of Historic Places on October 17, 1985.The oldest portion of Chestnut Hill, including its colonial roots, lies just over the line in Newton, and was also the part of the village that was the first to be developed as a suburban residential area. When the Brookline section was being planned for development, Frederick Law Olmsted was consulted in 1888, but his plans were not executed. The area was developed between then and about 1920, with large, high-quality houses on well-proportioned lots. Most of the houses in the district are either Colonial Revival or Shingle in their styling; there are also a few earlier Queen Anne houses and a number of later Craftsman-style houses, especially in the Reservoir Lane area which was the last to be developed.Several prominent area architectural firms were engaged in the development of properties in the district. Chapman & Frazer (later Chapman, Frazer & Blinn) were responsible for 29 of the more than 120 houses in the district; Horace Frazer lived in the district, at 471 Heath Street. Putnam & Cox designed seven homes, generally in the Arts and Crafts style, and William Putnam also lived in the district. Arthur Bowditch designed one house, as did the firm of Hartwell & Richardson.

Brimmer and May School is an independent, pre-K–12 school located in Chestnut Hill, Massachusetts. Brimmer and May is accredited by The New England Association of Schools and Colleges (NEASC) and is a member of the National Association of Independent Schools (NAIS), which in 2011 designated Brimmer and May as a "School of the Future." In addition, it is a member of the Association of Independent Schools in New England (AISNE), Coalition of Essential Schools (CES), and the National Center for Independent School Renewal (NCISR).

The House at 41 Middlesex Road in the Chestnut Hill section of Newton, Massachusetts, USA, is a well-preserved local example of Shingle style architecture. The 2+1⁄2-story stone-and-wood house was built in 1894 by William R. Dupee, who lived on a nearby estate. The house was designed by Boston architect Horace Frazer, of Chapman & Frazer, and initially occupied by Dr. Frederick William Payne. The ground floor has significant fieldstone elements, and the upper levels are clad in dark brown shingles. Some of the windows have diamond-paned muntins, a late Victorian touch. The house was expanded in the 1930s, with a 1+1⁄2-story addition and garage.The house was listed on the National Register of Historic Places in 1986.

Holyhood Cemetery is a cemetery located in Brookline, Massachusetts.

The 2022 United States Open Championship was the 122nd U.S. Open, the national open golf championship of the United States. It was a 72-hole stroke play tournament that was played between June 16–19 at The Country Club in Brookline, Massachusetts, a suburb west of Boston. It was the club's fourth U.S. Open, having been held there in 1913, 1963, and 1988. Matt Fitzpatrick won his first major championship, finishing the tournament with a score of 274, six-under-par, a shot ahead of Scottie Scheffler and Will Zalatoris. The win was also Fitzpatrick's first on the PGA Tour. He had previously won the U.S. Amateur at The Country Club, in 2013, and matched Jack Nicklaus, who won both at Pebble Beach, as the only players to win the U.S. Amateur and U.S. Open on the same course. Zalatoris, who lost in a playoff a month earlier at the PGA Championship, had a 14-foot birdie putt on the 18th green that would have forced a playoff but missed, and had his second consecutive runner-up finish in a major championship.

The Benjamin White House is a historic house at 203 Heath Street in Brookline, Massachusetts. Built in 1790, this two-story wood-frame house is one of the oldest on Heath Street. It has been moved twice: once when the Cabot family established a large estate in the area, at which time they moved it back from Heath Street and added a barn, and again in 1947, when the barn was demolished and the house moved onto its foundation. Much of the interior finish was lost during interior remodelling in the 1940s, but the exterior has retained much of its 18th and 19th century trim.The house was listed on the National Register of Historic Places in 1985.

Chestnut Hill station is a light rail station on the MBTA Green Line D branch, located off Hammond Street north of Massachusetts Route 9 in the Chestnut Hill neighborhood of Newton, Massachusetts. The station has two side platforms serving the line's two tracks. Chestnut Hill station is not accessible.

The Country Club, located in Brookline, Massachusetts, is the oldest golf-oriented country club in the United States. (The Philadelphia Cricket Club, founded in 1854, was the first country club for any sport.) It holds an important place in golf history, as it is one of the five charter clubs that founded the United States Golf Association, and has hosted numerous USGA tournaments including the 1913 U.S. Open won by then-unknown Francis Ouimet. Although the club has 1300 members, it is known for its exclusivity.

The Street at Chestnut Hill is an open-air shopping center on Route 9 in Chestnut Hill, Massachusetts. The shopping center contains 640,090 sq ft (59,466 m2) of fashion retailers, restaurants, and entertainment options. The architecture and design of the new shopping center mimics modern village-like streetscapes and overlooks neighboring Hammond Pond. The center contains a Showcase SuperLux and a Star Market.