House at 41 Middlesex Road

Chestnut Hill station is a light rail station on the MBTA Green Line D branch, located off Hammond Street north of Massachusetts Route 9 in the Chestnut Hill neighborhood of Newton, Massachusetts. The station has two side platforms serving the line's two tracks. Chestnut Hill station is not accessible.

Brimmer and May School is an independent, pre-K–12 school located in Chestnut Hill, Massachusetts. Brimmer and May is accredited by The New England Association of Schools and Colleges (NEASC) and is a member of the National Association of Independent Schools (NAIS), which in 2011 designated Brimmer and May as a "School of the Future." In addition, it is a member of the Association of Independent Schools in New England (AISNE), Coalition of Essential Schools (CES), and the National Center for Independent School Renewal (NCISR).

The Old Chestnut Hill Historic District encompasses the historic residential heart of the Newton portion of Chestnut Hill, Massachusetts. When first listed on the National Register of Historic Places in 1986, the district extended along Hammond Street, between Beacon Street and the MBTA Green Line right-of-way, and along Chestnut Hill Road between Hammond and Essex, including properties along a few adjacent streets. The district was expanded in 1990 to include more of Chestnut Hill Road and Essex Road, Suffolk Road and the roads between it and Hammond, and a small section south of the Green Line including properties on Hammond Street, Longwood Road, and Middlesex Road. A further expansion in 1999 added a single property on Suffolk Road.The district consists of a residential enclave of high-quality architect-designed residences on ample, landscaped lots, that exemplified the development of Newton as a fashionable upper-class suburb. The area's colonial history begins with settlement in the 17th century by Thomas Hammond and others. Hammond was probably the builder of the c. 1700 Hammond House at 9 Old Orchard Road, considered to be Newton's oldest surviving structure. The 1723 house at 521 Hammond Street, a substantial Georgian style house, also belonged to the Hammond family.Development of the area did not begin in a significant way until after 1886, when the Circuit Railroad brought rail service to the area. A station designed by H. H. Richardson was built at Chestnut Hill in 1883 and landscaped by Frederick Law Olmsted; it was demolished in 1960. The houses in the district are predominantly Colonial Revival in their styling, although other forms popular into the 1920s are also represented, including Tudor Revival. There has been only limited new construction in the area since 1942. The 98-acre (40 ha) district includes 132 buildings, of which 109 contribute to its significance.

The Street at Chestnut Hill is an open-air shopping center on Route 9 in Chestnut Hill, Massachusetts. The shopping center contains 640,090 sq ft (59,466 m2) of fashion retailers, restaurants, and entertainment options. The architecture and design of the new shopping center mimics modern village-like streetscapes and overlooks neighboring Hammond Pond. The center contains a Showcase SuperLux and a Star Market.

The Chestnut Hill Historic District encompasses the historic portion of the village of Chestnut Hill that lies in Brookline, Massachusetts, with only slight overlap into adjacent Newton. The 70-acre (28 ha) district is bounded on the north by Middlesex Road, on the east by Reservoir Lane, on the south by Crafts Road and Massachusetts Route 9, and on the west by Dunster Road. A small portion of the district extends south of Route 9, including a few houses and the Baldwin School on Heath Street. The district was listed on the National Register of Historic Places on October 17, 1985.The oldest portion of Chestnut Hill, including its colonial roots, lies just over the line in Newton, and was also the part of the village that was the first to be developed as a suburban residential area. When the Brookline section was being planned for development, Frederick Law Olmsted was consulted in 1888, but his plans were not executed. The area was developed between then and about 1920, with large, high-quality houses on well-proportioned lots. Most of the houses in the district are either Colonial Revival or Shingle in their styling; there are also a few earlier Queen Anne houses and a number of later Craftsman-style houses, especially in the Reservoir Lane area which was the last to be developed.Several prominent area architectural firms were engaged in the development of properties in the district. Chapman & Frazer (later Chapman, Frazer & Blinn) were responsible for 29 of the more than 120 houses in the district; Horace Frazer lived in the district, at 471 Heath Street. Putnam & Cox designed seven homes, generally in the Arts and Crafts style, and William Putnam also lived in the district. Arthur Bowditch designed one house, as did the firm of Hartwell & Richardson.

Chestnut Hill is a wealthy New England village located six miles (9.7 km) west of downtown Boston, Massachusetts, United States. Like all Massachusetts villages, Chestnut Hill is not an incorporated municipal entity. It is located partially in Brookline in Norfolk County; partially in the city of Boston in Suffolk County, and partially in the city of Newton in Middlesex County. Chestnut Hill's borders are defined by the 02467 ZIP Code. The name refers to several small hills that overlook the 135-acre (546,000 m2) Chestnut Hill Reservoir rather than one particular hill. Chestnut Hill is best known as the home of Boston College and as part of the Boston Marathon route.

Holyhood Cemetery is a cemetery located in Brookline, Massachusetts.

Beaver Country Day School is an independent, college-preparatory day school for students in grades 6 through 12 founded in 1920. The school is located on a 17-acre (69,000 m2) campus in the village of Chestnut Hill, Massachusetts, near Boston. Beaver is a member of the Cum Laude Society, the Independent Curriculum Group, and the National Association of Independent Schools. Beaver is accredited by the New England Association of Schools.

Roughwood is a historic estate at 400 Heath Street in Brookline, Massachusetts. It is currently the main campus of Pine Manor College. The main estate house and outbuildings were designed by Andrews, Jaques and Rantoul, and built in 1891 as the summer estate of William Cox, a wholesale dealer in the footwear industry. The estate house is one of the largest Shingle-style houses in Brookline. The property was reduced in size by sales of land to the adjacent country club, and for the establishment of Dane Park; the estate was acquired by Pine Manor College in 1961, which has retained the estate's rural flavor.It was added to the National Register of Historic Places in 1985.

The Kingsbury House is a historic house at 137 Suffolk Street in the Chestnut Hill section of Newton, Massachusetts. The oldest part of this 2+1⁄2-story timber frame may have been built as early as 1686; its exterior styling suggests a construction date in the early 18th century, but the earlier structure may have been incorporated in new construction at that time. The house is one a few First Period houses in Newton, and was associated for many years in the 19th century with the Kingsbury family, who were major landowners in the Chestnut Hill area.The house was listed on the National Register of Historic Places in 1986, and included in an expansion of the Old Chestnut Hill Historic District in 1990.

Eddie Pellagrini Diamond at John Shea Field was a baseball stadium in Chestnut Hill, Massachusetts. It was the home field of the Boston College Eagles baseball team from 1961 to 2017. The stadium held 1,000 people and was named after Commander John Joseph Shea, USN, a former football player (1916–1917) at Boston College, who died on September 15, 1942, when the aircraft carrier USS Wasp was torpedoed and sunk during the Guadalcanal Campaign in World War II. In 1997, the diamond was named for Eddie Pellagrini, head coach of the Eagles for 31 years and the coach of the team when the field opened in 1961.Shea Field was also home to many tailgaters during home football games at the adjacent Alumni Stadium. The Boston College baseball team played its final game at Shea Field on May 20, 2017. The team moved to a new baseball stadium, on nearby Brighton Campus, in spring 2018. Boston College's new Athletics Field House, an indoor practice facility for football and other varsity and intramural sports, is currently being constructed on the site of the former Shea Field. It is expected to open in August 2018.

Roberts Center was a 4,400-seat multi-purpose arena in Chestnut Hill, Massachusetts, United States. It opened in 1958 and was home to the Boston College Eagles men's basketball and women's basketball teams until the Conte Forum opened in 1988.