Chestnut Hill
The Brookline side of Chestnut Hill — grand homes, the Reservoir, and proximity to Boston College.
About Chestnut Hill
The Brookline side of Chestnut Hill shares the same prestige address as Newton's Chestnut Hill but with a distinctly Brookline character — Brookline schools, Brookline town services, and a slightly different housing mix. The Chestnut Hill Reservoir is the centerpiece, with its 1.5-mile perimeter loop that draws walkers and joggers year-round. Route 9 runs through the area with The Street Chestnut Hill and the Chestnut Hill Mall providing upscale shopping. The residential streets — particularly along Heath Street, Clyde Street, and around the Reservoir — feature some of the grandest homes in Brookline. Boston College's campus borders the neighborhood, adding energy and cultural programming. This is Brookline at its most suburban and its most expensive.
Property Character
Grand single-family homes on large lots are the defining feature. Brick Colonials, stone Tudors, and estate-quality properties on streets with a country-club feel. Some of the largest residential parcels in Brookline. Less density than northern Brookline — no apartment buildings or condo conversions here. Very limited inventory; homes rarely come on the market and sell quickly when they do.
Typical Home Styles
Best For
Local Highlights
- •Chestnut Hill Reservoir — 1.5-mile walking loop, one of the best in Greater Boston
- •The Street Chestnut Hill — open-air luxury shopping and dining
- •Boston College campus — beautiful grounds, Conte Forum events, cultural programming
- •Hammond Pond Reservation — hiking trails and a glacial pond
- •Chestnut Hill Mall — upscale retail including Bloomingdale's
Getting Around
Chestnut Hill station on the Green Line D branch is at the neighborhood edge. The B line terminus (Boston College) is also accessible. Driving is the primary mode — Route 9 provides east-west access, and the Mass Pike is reachable via Newton. The 86 bus runs to Harvard Square via Brighton. Most residents in this area own cars and use them.
Schools
Served by Baker School (K-8), one of Brookline's smaller and most desirable school zones. Baker is well-funded with strong parent engagement and excellent test scores. All students attend Brookline High School. The Baker school zone is a significant driver of real estate demand in this part of Brookline.
Explore more of Brookline
Chestnut Hill is just one part of what makes Brookline special.