Larz Anderson Auto Museum

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.

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.

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 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.

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 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 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.

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.

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 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 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.