Paine Estate

Roughwood is a historic estate at 400 Heath Street in Brookline, Massachusetts. It is currently the main campus of Pine Manor College. The main estate house and outbuildings were designed by Andrews, Jaques and Rantoul, and built in 1891 as the summer estate of William Cox, a wholesale dealer in the footwear industry. The estate house is one of the largest Shingle-style houses in Brookline. The property was reduced in size by sales of land to the adjacent country club, and for the establishment of Dane Park; the estate was acquired by Pine Manor College in 1961, which has retained the estate's rural flavor.It was added to the National Register of Historic Places in 1985.

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.

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 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.

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

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.

Fernwood is a historic estate house at 155 Clyde Street in Brookline, Massachusetts, United States. Built in 1909, it is a distinctive example of Jacobethan architecture, and one of a few surviving country estate houses of the early 20th century in the town. The house 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.

The General Simon Elliot House is a historic house at 61 Heath Street in Brookline, Massachusetts. Built in 1824, it is one of the town's oldest examples of Greek Revival architecture, owned by several prominent residents. The house was listed on the National Register of Historic Places on October 17, 1985.

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 1988 U.S. Open was the 88th U.S. Open, held June 16–20 at The Country Club in Brookline, Massachusetts, a suburb southwest of Boston. Curtis Strange defeated Nick Faldo in an 18-hole playoff for the first of two consecutive U.S. Open titles.

The 33rd Ryder Cup, also known as the "Battle of Brookline", was held September 24–26, 1999, in the United States at The Country Club in Brookline, Massachusetts, a suburb southwest of Boston. The American team won the competition by a margin of 141⁄2 to 131⁄2, The Europeans, leading 10–6 heading into the final round, needed only 4 points on the final day to retain the cup. The Americans rallied on the Sunday, winning the first 6 matches of the day to surge into the lead. Further wins by Steve Pate and Jim Furyk took them into a 14–12 lead. The Americans recaptured the Ryder Cup when Justin Leonard halved his match with José María Olazábal. With the match all-square Leonard holed a 45-foot birdie putt on the 17th hole. After controversial premature celebrations on the green, Olazabal then missed his 22-foot birdie putt to leave Leonard one up with just one hole to play, assuring him of a half point and guaranteeing an American victory. The behavior of both U.S. spectators and the U.S. team was criticized by both American and European media. U.S. spectators raucously heckled and abused European players. Allegations were also made regarding cheating on the part of course marshals. Notoriously, the U.S. team raucously invaded the 17th green after Leonard had holed his long putt but before Olazábal had attempted his shorter putt. The incident was viewed by many in both the US and Europe as appalling sportsmanship. Veteran broadcaster Alistair Cooke described the last day of the tournament as "a date that will live in infamy" in a Letter from America entitled "The arrival of the golf hooligan".At the time, the American win was the largest final day come-from-behind victory in Ryder Cup history; Europe achieved the same feat in 2012. It is still widely regarded as one of the most impressive come-from-behind victories in recent sports history.This was one of the last public appearances of Payne Stewart, who died in a plane crash less than a month later.