Holyhood Cemetery

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.

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.

Hammond Pond Parkway is a historic parkway in Chestnut Hill, Massachusetts. The road, built in 1932, extends 2 miles (3.2 km) from Hobart Road (at Beacon Street) in Newton to Horace James Circle in Brookline, where it joins the West Roxbury Parkway. It was designed by Charles Eliot and the Olmsted Brothers to provide a parkway setting that provided access from Brookline, Newton, and the western portions of Boston to the southern parks of the Emerald Necklace. The parkway was listed on the National Register of Historic Places in 2004.

The House at 41 Middlesex Road in the Chestnut Hill section of Newton, Massachusetts, USA, is a well-preserved local example of Shingle style architecture. The 2+1⁄2-story stone-and-wood house was built in 1894 by William R. Dupee, who lived on a nearby estate. The house was designed by Boston architect Horace Frazer, of Chapman & Frazer, and initially occupied by Dr. Frederick William Payne. The ground floor has significant fieldstone elements, and the upper levels are clad in dark brown shingles. Some of the windows have diamond-paned muntins, a late Victorian touch. The house was expanded in the 1930s, with a 1+1⁄2-story addition and garage.The house was listed on the National Register of Historic Places in 1986.

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).

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 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 Shops at Chestnut Hill is a two-level enclosed shopping mall, located in the Chestnut Hill section of Newton, Massachusetts on Boylston Street (Route 9). As of 2022, the mall currently features two Bloomingdales, as well as prominent brands Apple, Uniqlo, Crate & Barrel, Tiffany & Co., and Brooks Brothers. It is managed by Simon Property Group, who owns 94.4% of it. Bloomingdale's Women's store is located at the west end of the complex and the Men's Home & Furnishing store anchoring the east end. These are the only Bloomingdale's locations in Massachusetts.

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.

The House at 152 Suffolk Road in the Chestnut Hill area of Newton, Massachusetts is a rare local example of the Spanish Mediterranean style of Colonial Revival architecture. The house, built in 1904, is set apart from more typical Colonial Revival structures by its use of ceramic tile as roofing, stucco walls, and a Mediterranean-style loggia.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.

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.