Chestnut Hill is a wealthy New England village located six miles (10 km) west of downtown Boston, Massachusetts, United States. It is best known for being home to Boston College and a section of the Boston Marathon route. 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 m) Chestnut Hill Reservoir rather than one particular hill.

The boundary between Newton and Brookline was originally more or less straight northwest–southeast, following today's boundary at the east edge of the Newton Commonwealth Golf Course, and the west boundary of the MBTA rail yards. It followed what is today St. Thomas More Road and Chestnut Hill Driveway through swampland that is today the western edge of the Chestnut Hill Reservoir, and then rejoined today's city limit that runs essentially with the portion of Beacon Street that forms the western boundary of the Reservoir, and continues southeast to today's triple point between Boston, Brookline, and Newton near the intersection of Reservoir Road and Middlesex Road. Around the 1870s, the Lawrence farm land that is today bounded by Commonwealth Avenue, the slope dividing Boston College upper campus from lower campus, Beacon St., Chestnut Hill Driveway, and St. Thomas More Rd. was ceded from Newton to Boston, so that Boston could construct the Chestnut Hill Reservoir. What is today the Boston College lower campus and stadium was excavated to become the Lawrence Basin of the Reservoir, paired with the surviving Bradlee Basin, to receive water from the Sudbury Aqueduct. Beacon St. was rerouted around the southern and western edges of the Bradlee Basin. The two halves of the Reservoir were separated to preserve the Cochituate Aqueduct, which ran under a causeway separating the two halves of the reservoir, now roughly St. Thomas More Rd. and Chestnut Hill Driveway, and a short stretch of Beacon Street.

While most of Chestnut Hill remained farmland well into the early 20th century, the area around the reservoir was developed in 1870 by landscape architect Frederick Law Olmsted, designer of Central Park in New York City and of the Emerald Necklace in Boston and Brookline.

Because of the significance of its landscape and architecture, the National Register of Historic Places designated parts of Chestnut Hill as historic districts in 1980s. Examples of Colonial, Italianate, Shingle, Tudor Revival, and Victorian architectural styles are evident in the village's country estates and mansions. The Boston College campus is itself an early example of Collegiate Gothic architecture.

Hammond Pond Reservation, an extensive forest preserve and protected wetlands, goes through Chestnut Hill and Newton where it is also known as Webster Woods.

The Kennard Park and Conservation Area is a post-agricultural forest grown up on 19th century farmland. The mixed and conifer woodlands reveal colonial stone walls, a red maple swamp with century-old trees, and a sensitive fern marsh.

The Chestnut Hill Reservation embraces 120 acres adjacent to the Boston College campus, including a 1.5 mile walking trail around a reservoir. The Reservation was designed by Frederick Law Olmsted’s son and constructed in the late 1860s to give Boston clean drinking water and a rural park. Just outside the park proper, the Boston Waterworks with its three gatehouses at water’s edge and three majestic pump houses on Beacon Street is considered a masterpiece of 19th century engineering and landscape design.

The Heartbreak Hill Park, surrounding the Waban Hill reservoir, opened in 2015, and a major renovation was completed in 2020.

• The Shops at Chestnut Hill
• The Street at Chestnut Hill

Chestnut Hill is served by two branches of the Green Line of the MBTA, Boston's light rail system. Stations include:

• B branch: Boston College; terminus of the line
• D branch: Chestnut Hill

The area is also served by the 51 and 60 MBTA buses.

Massachusetts Route 9 runs through the area from west to east and serves as the main retail corridor for Chestnut Hill and many surrounding communities. Hammond Pond Parkway connects the area from north to south as a four-lane road through conservation areas, bypassing the busy retail areas and residential neighborhoods.

• Boston College Main Campus Historic District – 140 Commonwealth Ave. (in Newton)
• Chestnut Hill Historic District – roughly bounded by Middlesex Rd., Reservoir Ln., Denny Rd., Boylston St. and Dunster Rd. (added November 17, 1985) (mostly in Brookline, but includes a few properties that spill into Newton)
• Chestnut Hill Reservoir Historic District – within Boston city limits
• Old Chestnut Hill Historic District – along Hammond St. and Chestnut Hill Rd. roughly bounded by Beacon St. and Essex Rd., and Suffolk Rd. (added October 4, 1986), within Newton city limits

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The village is served by the Brookline Public Schools, Newton Public Schools, and Boston Public Schools, depending on the city or town in which a particular residence is located. The neighborhood also features several private schools including Brimmer and May School (non-denominational, K–12), The Chestnut Hill School, and Beaver Country Day School.

Chestnut Hill is home to both Boston College and Pine Manor College (formerly).

• Mike Wallace, TV host CBS, 60 Minutes, Brookline High School graduate

• List of Registered Historic Places in Brookline, Massachusetts
• List of Registered Historic Places in Newton, Massachusetts
• List of Registered Historic Places in Suffolk County, Massachusetts

• Begans, Pete (September 16, 1974). "A Brief History of Chestnut Hill". The Heights. Vol. LV, no. 3. Boston College Newspapers.