John Goddard House

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.

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.

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 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.

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.

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 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.

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 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 Perkins Estate is a historic estate at 450 Warren Street in Brookline, Massachusetts. The property was part of the summer estate of the Cabot family, originally belonging to Thomas Handasyd Perkins; the present main mansion house was built in the 1850s to a plan by Edward Clarke Cabot for his sister-in-law, Elizabeth Perkins Cabot. The grounds of the property were originally designed by Perkins, and subsequent generations maintained the grounds to a high degree. In the 1980s it was owned by Mitch Kapor, founder of Lotus Software. The property was listed on the National Register of Historic Places in 1985.

The Lewis Cabot Estate was a historic estate at Warren and Heath Streets in Brookline, Massachusetts. The estate, developed in 1894, was one of few surviving turn-of-the-century properties of the Boston Brahmin Cabot family, and a prominent local example of Jacobethan architecture with landscaping by Frederick Law Olmsted. The remnant portion of the estate was listed on the National Register of Historic Places in 1985; the main house has since been demolished.