Walnut Hills Cemetery (Brookline, Massachusetts)

Allandale Farm, also known as the John Harris House and Farm, and once as Faulkner Farm, is an historic farm at 284 Newton Street in Chestnut Hill, Massachusetts. The main farm house, built c. 1778 and extensively remodeled in 1976, is one of Brookline's few 18th-century houses. The farm is the last working farm in both communities; it was added to the National Register of Historic Places in 1985.

The Brandegee Estate is a historic estate at 280 Newton Street in Brookline and Boston, Massachusetts. Developed at the turn of the 20th century, it is one of the largest essentially intact estate properties in either community. It was developed by Mary (Pratt) Sprague, a direct descendant of Joseph Weld, one of Boston's first settlers, and is noted for its large Renaissance Revival mansion (designed by Little, Browne & Moore), and landscaping by Charles A. Platt. The estate was listed on the National Register of Historic Places in 1985. Its name derives from Mary Sprague's second husband, Edward Brandegee.

West Roxbury Parkway is a historic parkway running from Washington Street in Boston, Massachusetts, where the Enneking Parkway runs south, to Horace James Circle in Chestnut Hill, where it meets the Hammond Pond Parkway. The parkway serves as a connector between Stony Brook Reservation and Hammond Pond Reservation (via Hammond Pond Parkway). West Roxbury Parkway was built between 1919 and 1929 and added to the National Register of Historic Places in 2006. The parkway is distinctive in the roadway system developed by the Metropolitan District Commission beginning around the turn of the 20th century in that it was built in collaboration with the City of Boston, and is maintained by the city.At the northern end of the Stony Brook Reservation, the parkway runs through Bellevue Hill Park. The boundary roads of Bellevue Hill Park (Bellevue Hill Road, East Border Road, and West Border Road), which flank the parkway, are also listed as contributing properties to the West Roxbury Parkway. The West Roxbury Parkway also intersects with the Veterans of Foreign Wars Parkway.

The Thaddeus Jackson House is a historic house at 15 Alberta Road in Brookline, Massachusetts. Built in 1820, it is one of Brookline's older surviving houses, unusual because it was built in the Georgian style, then already out of fashion. The house was listed on the National Register of Historic Places on October 17, 1985.

The Isaac Child House is a historic house at 209 Newton Street in Brookline, Massachusetts. With a documented history dating to the 1790s, it is one of Brookline's few surviving 18th-century houses. It was listed on the National Register of Historic Places in 1985.

The Alfred Douglass House was a historic house at 76 Fernwood Road in Brookline, Massachusetts, United States. It was built in 1910 as servant quarters for the Fernwood estate of Alfred Douglass. It was a prominent surviving example of Jacobethan architecture in Brookline, and an unusual surviving outbuilding from one of the town's early 20th century country estates. The house was listed on the National Register of Historic Places in 1985. It has since been demolished and replaced by new construction.

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 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.

Southfield School was an independent school for girls in Brookline, Massachusetts, United States. Founded in 1992, its campus is also home to its brother school, Dexter, an independent school for boys founded in 1926. In 2013 the school merged with Dexter to form Dexter Southfield School.