Pine Manor College

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 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.

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 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.

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 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.

The 1963 U.S. Open was the 63rd U.S. Open, held June 20–23 at The Country Club in Brookline, Massachusetts, a suburb southwest of Boston. Julius Boros won his second U.S. Open title in an 18-hole Sunday playoff with Jacky Cupit and Arnold Palmer. The U.S. Open returned to The Country Club for the first time in fifty years to celebrate the golden anniversary of Francis Ouimet's playoff victory in 1913. Boros won eleven years earlier in 1952, and won a third major at age 48 at the PGA Championship in 1968. At 43, Boros was the second-oldest winner in U.S. Open history, and only a month younger than Ted Ray when he won the 1920 Open. For Palmer, it was the second consecutive year he lost in a playoff at the Open.High winds made scoring conditions extremely difficult throughout the entire week, especially on Saturday during the final two rounds, when gusts approached 50 mph (80 km/h). The winning score of 293 remains the highest in post-World War II U.S. Open history, while the 77.4 final-round scoring average set a record for the post-war era, later broken in 1972 at Pebble Beach. For the first time in U.S. Open history, no amateur made the cut. Defending champion and Masters winner Jack Nicklaus missed the cut by a stroke; his next missed cut at the U.S. Open came 22 years later in 1985. He rebounded in the next two majors in 1963, missing the playoff at the Open Championship in England by a stroke for third place and won the PGA Championship in Dallas the following week. This U.S. Open was played the week after Father's Day.

The 1913 U.S. Open was the 19th U.S. Open, held September 18–20 at The Country Club in Brookline, Massachusetts, a suburb southwest of Boston. Amateur Francis Ouimet, age 20, won his only U.S. Open title in an 18-hole playoff, five strokes ahead of Britons Harry Vardon and Ted Ray.The four rounds were played over two days, Thursday and Friday. After 36 holes, Vardon and Wilfrid Reid co-led at 147 (+1), and after the third round on Friday morning, Ouimet, Vardon, and Ray were tied for the lead at 225 (+6). All three shot 79 in the afternoon and remained tied for the lead at the end of regulation at 304 (+12).In the Saturday playoff round, all were tied at even-par 38 at the turn, then Ouimet had a bogey-free back nine 34 for 72 (−1), Vardon was second with 77, and Ray came in third with a 78. It was widely hailed as a stunning upset over the strongly-favored Britons and increased the popularity of the game in the United States. Ouimet's victory was the first of eight wins by amateurs at the U.S. Open; Bobby Jones won four and the last was Johnny Goodman in 1933, 90 years ago. The U.S. Open returned to the course for the 50th and 75th anniversaries in 1963 and 1988, and the U.S. Amateur was held at The Country Club on the centennial anniversary in 2013; it also hosted the Ryder Cup in 1999. All four events, except the 2013 U.S. Amateur, were won by Americans. The 2022 U.S. Open, again played at The Country Club, was won by Englishman Matt Fitzpatrick. Vardon, the 1900 champion, won a sixth British Open in 1914. Ray, the British Open champion in 1912, won the U.S. Open in 1920. The tournament inspired the Mark Frost book The Greatest Game Ever Played: Harry Vardon, Francis Ouimet, and the Birth of Modern Golf (2002). The book was adapted into the film The Greatest Game Ever Played (2005), directed by Bill Paxton.

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.

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 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.