Putterham School

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.

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.

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 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.

Hellenic College Holy Cross Greek Orthodox School of Theology (HCHC) is an Orthodox Christian liberal arts college and seminary in Brookline, Massachusetts. Its mission is to educate individuals for life and service in the Orthodox Christian community; this includes men preparing for the priesthood of the Greek Orthodox Archdiocese and other Orthodox Christian entities, as well as men and women for leadership roles in the church or within secular society. HCHC includes a graduate school of theology (seminary) for clerical training and education, and several undergraduate and certificate programs in business, education, literature, and other secular professions. The institution was founded in 1937 as Holy Cross Theological School in Pomfret, Connecticut, but was moved to Brookline, Massachusetts in 1947.

The George R. Minot House is a National Historic Landmark in Brookline, Massachusetts. It is an architecturally undistinguished vernacular Colonial Revival brick house, probably built in the 1920s. The 2+1⁄2-story main block has an attached 1+1⁄2-story ell, and two end chimneys. The hip roof is pierced by gabled dormers, and a pedimented portico shelters the front entry.

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 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.

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.

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.

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.