Chestnut Hill
Chestnut Hill is Newton's most prestigious neighborhood — an affluent enclave of grand estates, manicured landscapes, and world-class amenities. Home to Boston College and The Street Chestnut Hill shopping center, this village offers some of the highest property values in Massachusetts with a median price of $2.1 million, top-rated schools, and a refined lifestyle that attracts executives, academics, and established families.
$2,100,000
Median Price
$900K – $8M+
Price Range
62
Walk Score
10/10
School Rating
20 min via Green Line D
Commute to Boston
Newton, MA
Location
What Is Chestnut Hill Like?
Chestnut Hill straddles the Newton-Brookline border and represents the pinnacle of luxury suburban living in Greater Boston. The neighborhood is defined by its sweeping estates on tree-lined streets like Hammond, Crafts, and Woodchester, where homes sit on generous half-acre to multi-acre lots. The architectural palette ranges from grand Georgian Colonials and stately Tudor revivals to architect-designed contemporary masterpieces. Boston College anchors the northern edge, lending intellectual energy and cultural programming to the area. The Street Chestnut Hill — an upscale outdoor shopping destination with Bloomingdale's, Tiffany & Co., and notable dining — serves as the village's commercial hub. Hammond Pond Reservation offers over 100 acres of walking trails and natural beauty just minutes from home. Chestnut Hill families enjoy access to Newton's top-rated public schools, including the Bowen Elementary School (rated 10/10), Bigelow Middle School, and Newton South High School. The Green Line D branch provides transit access to Boston, though many residents drive via Route 9 or the Massachusetts Turnpike.
What Are Home Prices in Chestnut Hill?
Chestnut Hill commands Newton's highest home prices, with a median of approximately $2,100,000. The market ranges from $900,000 condos and smaller homes to $8 million+ grand estates on premium streets. Properties here are rare and tightly held — inventory is consistently low, and homes in prime locations generate significant buyer interest. New construction and major renovations are common, with builders creating modern luxury homes on established lots. Year-over-year appreciation has been strong at 5-8%, and Chestnut Hill real estate is considered a blue-chip investment in the Greater Boston market. The proximity to Boston College means a small rental market exists, but the vast majority of transactions involve owner-occupied single-family homes.
What Are the Schools Like in Chestnut Hill?
Chestnut Hill students attend some of Newton's highest-rated schools. Bowen Elementary School is rated 10/10 and is considered one of the district's finest. Students then attend Bigelow Middle School before progressing to Newton South High School, which ranks among the top public high schools in Massachusetts with exceptional AP offerings, athletics, and college placement. Boston College adds to the educational environment with public lectures, cultural events, and library access. The Fessenden School, a prestigious private school for boys, is located nearby, as are other private options including Brimmer and May.
Where to Eat and Shop in Chestnut Hill?
The Street Chestnut Hill is the village's premier shopping destination, featuring upscale retailers like Bloomingdale's, Apple, and Tiffany & Co. alongside restaurants such as The Capital Grille, Legal Sea Foods, and Seasons 52. Beyond The Street, Chestnut Hill has easy access to the Hammond Street shops and the Route 9 retail corridor. The neighborhood's proximity to both Brookline's Coolidge Corner and Newton Centre's village center provides additional dining options. The Chestnut Hill Reservoir, while technically in Boston/Brookline, is a popular walking destination for residents.
Parks & Recreation in Chestnut Hill
Hammond Pond Reservation is Chestnut Hill's natural treasure — over 100 acres of trails, woodlands, and a scenic pond perfect for walking, birdwatching, and nature photography. The Chestnut Hill Reservoir offers a beautiful 1.5-mile walking loop popular with joggers and families. Crystal Lake in neighboring Newton Centre provides summer swimming. The neighborhood features well-maintained private and public green spaces, and Newton's extensive park system provides additional recreation options. The Boston College campus grounds are also open for walking.
How Do You Get Around Chestnut Hill?
Chestnut Hill offers good transit options via the MBTA Green Line D branch (Chestnut Hill and Reservoir stops), providing service to Boston in approximately 20 minutes. Route 9 runs through the neighborhood providing east-west highway access, and the Massachusetts Turnpike is easily reached for commuting. The walk score of 62 reflects the more suburban, estate-oriented layout — daily errands often require a short drive, though The Street Chestnut Hill provides walkable shopping for nearby residents. Express bus routes are also available.
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Neighborhood Highlights
- ✓Boston College
- ✓The Street Chestnut Hill
- ✓Hammond Pond
- ✓Grand estates
Frequently Asked Questions
Chestnut Hill FAQ
What is Chestnut Hill, Newton like?
Chestnut Hill is Newton's most prestigious neighborhood, known for grand estates, manicured landscapes, Boston College, and The Street Chestnut Hill shopping center. It offers the highest property values in Newton with a median price of $2.1M and top-rated schools.
What are home prices in Chestnut Hill, Newton?
The median home price in Chestnut Hill is approximately $2,100,000, making it Newton's most expensive village. Prices range from about $900,000 for condos to over $8 million for grand estates on premium streets like Hammond and Crafts.
What schools serve Chestnut Hill in Newton?
Chestnut Hill students attend Bowen Elementary (rated 10/10), Bigelow Middle School, and Newton South High School — one of Massachusetts' top-ranked public high schools. Private options include The Fessenden School and Brimmer and May.
Is Chestnut Hill a good place to live?
Chestnut Hill is considered one of the most desirable neighborhoods in Greater Boston, offering grand homes on spacious lots, top-rated schools, world-class shopping at The Street, Hammond Pond trails, and a refined community atmosphere.
What is The Street Chestnut Hill?
The Street Chestnut Hill is an upscale outdoor shopping center featuring Bloomingdale's, Tiffany & Co., Apple, and notable restaurants like The Capital Grille and Legal Sea Foods. It's the primary commercial center for the Chestnut Hill area.
How do you commute from Chestnut Hill to Boston?
Chestnut Hill offers Green Line D branch access (Chestnut Hill stop) reaching Boston in about 20 minutes. Route 9 and the Mass Turnpike provide easy driving access. Express bus routes are also available for downtown commuters.
What types of homes are in Chestnut Hill?
Chestnut Hill features grand Georgian Colonials, stately Tudor revivals, and architect-designed contemporary homes on generous half-acre to multi-acre lots. New construction and major renovations are common. Some condo options exist in converted properties.
What parks are in Chestnut Hill, Newton?
Hammond Pond Reservation offers over 100 acres of trails and natural beauty. The Chestnut Hill Reservoir provides a popular 1.5-mile walking loop. Crystal Lake, Newton's park system, and Boston College's grounds offer additional recreation.
How competitive is the Chestnut Hill real estate market?
Chestnut Hill's market is extremely competitive with consistently low inventory. Properties on premium streets generate significant buyer interest, and year-over-year appreciation has been 5-8%. An experienced local agent is essential.
Is Chestnut Hill Newton or Brookline?
Chestnut Hill straddles the Newton-Brookline border. The Newton side is a village within Newton's city limits, while the Brookline side is part of Brookline. They share proximity to Boston College and The Street Chestnut Hill but have different school districts and governance.