Hellenic College Holy Cross Greek Orthodox School of Theology

Sargent's Pond is a man-made 3-acre (1.2 ha) pond on Sargent Road in Brookline, Massachusetts. The pond was created by Charles Sprague Sargent (best known as the first director of the Arnold Arboretum) in the late 1870s as a centerpiece of his family's extensive Holm Lea estate. Sargent's estate has since been subdivided, but the roads giving access to it run along the estate's original alignments. Sargent landscaped the estate using similar principles to those he applied at the Arboretum, with vistas and a variety of trees and shrubs. The pond was created by damming a brook. It still has naturalistic plantings around it, although some Sargent's rhododendrons (a significant draw on occasions when he opened the estate to the public) have died.The pond (along with its immediately surrounding grounds) was listed on the National Register of Historic Places in 1985.

The Park School is an independent day school in Brookline, Massachusetts, for boys and girls providing pre-Kindergarten through eighth grade education. Founded in 1888 as Miss Pierce's School, it is a 34-acre campus in Brookline, Massachusetts near Jamaica Pond.

The Green Hill Historic District encompasses historical cross-section of residential housing in Brookline, Massachusetts, dating from the 18th century into the mid-20th century. The district includes properties on Warren, Cottage, and Fairmount Streets, and on Sargent Road, centered on the junction of Warren and Cottage Streets. The oldest houses (e.g. 215 Warren Street) date to the mid-18th century, and were originally modest Georgian or Federal structures. During the 19th century the area was populated by the summer estates of some of Boston's leading merchant and business families, including members of the Cabot and Perkins families. During the later 19th and early 20th centuries some of Brookline's largest and most architecturally interesting homes were built in this area.The district was listed on the National Register of Historic Places in 1985.

Putterham School, built 1768, is a one room schoolhouse in Brookline, Massachusetts. Originally built at the juncture of Grove and Newton Streets, in 1966 the school was moved from its original site to its present location at Larz Anderson Park.

The John Goddard House is a historic house at 235 Goddard Avenue in Brookline, Massachusetts, US. The two-story wood-frame house was originally built by Joseph Goddard in 1670 and re-built by his grandson John Goddard in 1767, a farmer. It is one of the few 18th-century houses in Brookline, important for the role it and its owner played in the American Revolutionary War during the Siege of Boston in 1776. The house was added to the National Register of Historic Places in 1985.

Frederick Law Olmsted National Historic Site is a United States National Historic Site located in Brookline, Massachusetts, a suburb of Boston. Frederick Law Olmsted (1822–1903) is recognized as the founder of American landscape architecture and the nation's foremost parkmaker of the 19th century. In 1883, Olmsted moved his home to suburban Boston and established "Fairsted", the world's first full-scale professional office for the practice of landscape design. Over the course of the next century, his sons and successors expanded and perpetuated Olmsted's design ideals, philosophy, and influence. The site is located at 99 Warren Street, in the Green Hill section of Brookline. Olmsted bought the Clark homestead, an 1810 Federal farmhouse, in 1883, to be near his frequent collaborator, H. H. Richardson, whose home and office were nearby. Olmsted and his son John Charles renovated the house, landscaped the property, and relocated the barn closer to the house, and in 1903 added the office wing to the northwest of the main house. Members of the Olmsted family occupied the main house until 1936, when Frederick Law Olmsted Jr. moved to Elkton, Maryland, renting the house to tenants. The offices of the Olmsted Brothers firm continued to be in the wing during this time, although business also declined. Members of the firm reoccupied the house in the 1960s, making substantial alterations to the original landscaping of the property. The property was acquired by the National Park Service in 1980. The grounds have been restored to a c. 1930 appearance, restoring much of Olmsted's landscaping.Park resources include the restored "Fairsted" historic landscape, and the design office (which remains virtually unchanged from the days when the Olmsted firm's activity was at its height.) Housed within the office complex are nearly 1,000,000 original design records detailing work on many of America's most treasured landscapes, including the grounds of the U. S. Capitol and White House; Great Smoky Mountains and Acadia National Parks; Yosemite Valley; New York's Central Park; and whole park systems in cities such as Buffalo, Seattle, Boston, Louisville and Montreal. The Olmsteds also played an influential role in the creation of the National Park Service, which now owns and maintains the Olmsted site. Frederick Law Olmsted National Historic Site is open to the public. The Park Service offers guided tours of the grounds and office wing.

Larz Anderson Auto Museum is located in the Anderson Carriage House on the grounds of Larz Anderson Park in Brookline, Massachusetts and is the oldest collection of motorcars in the United States.The museum is a non-profit educational institution with community events, lectures, children's programs, walking tours of the park, and an ever-changing series of exhibits on motor vehicles and the automobile's impact on society and culture.

Larz Anderson Park is a wooded, landscaped, and waterscaped 64-acre (26 ha) parkland in Brookline, Massachusetts that is listed on the National Register of Historic Places. The southwest corner of the park is in Boston. The park contains playing fields, picnic areas, gardens, waterways, an ice skating rink, and two sites of special interest: Larz Anderson Auto Museum, the oldest automobile collection in the United States Putterham School, a one-room schoolhouse from colonial timesAs Larz Anderson Park is about a half-mile away from Jamaica Pond it might also be considered a de facto extension of Boston's Emerald Necklace into the town of Brookline.

Jamaica Pond is a kettle lake, part of the Emerald Necklace of parks in Boston designed by Frederick Law Olmsted. The pond and park are in the Jamaica Plain neighborhood of Boston, close to the border of Brookline. It is the source of the Muddy River, which drains into the lower Charles River.USGS 2005The pond has an area of about 68 acres (28 ha), and is 53 feet (16 m) deep at its center (MassWildlife map), making it the largest body of fresh water in Boston, and the largest natural freshwater body in the lower Charles River watershed. It is ringed by a 1.5-mile (2.4 km) walking path, and is an extremely popular destination for Bostonians for walking, fishing, rowing, and sailing. Around Halloween each year, the pond serves as the site for The Lantern Parade. Participants dress in their Halloween costumes and walk around the pond. The pond once served as a reservoir for the City of Boston and the Town of West Roxbury, and it supplied ice in the winter to Boston and beyond.According to the USGS, the name Jamaica derives from an Indian name meaning "abundance of beavers".The pond's setting, Jamaica Park, was included in the Olmsted Park landscape complex that was placed on the National Register of Historic Places on December 8, 1971.

Pinebank Mansion was a Queen Anne style house sited on a hill overlooking Jamaica Pond in Boston, Massachusetts. Built in 1868 by John Hubbard Sturgis, it was the only mansion retained by Frederick Law Olmsted in his plans for the Emerald Necklace park system. It was the only original structure remaining in the park system at the time of its demolition in 2007.

The Brookline Town Green Historic District encompasses the historic colonial heart of the town of Brookline, Massachusetts. Centered on a stretch of Walnut Street between Warren and Chestnut Streets, this area is where the town's first colonial meeting house and cemetery were laid out, and was its center of civic life until the early 19th century. The district was listed on the National Register of Historic Places in 1980.

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.