Best Neighborhoods in Brookline, Massachusetts

Brookline is a small, dense town, and each neighborhood is walkable in its own way, all feeding Brookline High. Coolidge Corner is the social center, anchored by the Coolidge Corner Theater, a nonprofit independent cinema, with restaurants, shops and a major transit stop. Brookline Village is the historic district, with brick buildings and a charming downtown feel, popular with healthcare workers for its proximity to the Longwood Medical Area.

Washington Square is quieter than Coolidge Corner but still walkable, with tree-lined streets and boutique cafes. Chestnut Hill is a very affluent residential area with larger homes and the upscale Chestnut Hill Mall, tied to Boston College. South Brookline is the leafiest and most suburban, with bigger lots and more open space.

Coolidge Corner Neighborhood

Families who want walkability and easy access to city life.

The Vibe: Coolidge Corner is the social center of town. The cornerstone of the neighborhood is the Coolidge Corner Theater, a nonprofit, independent cinema and community culture center, surrounded by restaurants, shops, and a major transit stop.

The Schools: Served by:

Housing: Mix of condos, apartments, and historic homes. Prices usually range from $750K–$1.5M for condos and small single-family homes; luxury condos can run higher.

Good Fit For: Families who want walkability and easy access to city life.

Similar Neighborhoods:

  • Davis Square (Somerville, MA)
  • Princeton Downtown (NJ)
  • Maplewood Village (NJ)

Washington Square Neighborhood

Families seeking calm while staying connected to amenities.

The Vibe: Washington Square is quieter than Coolidge Corner but still walkable. It has beautiful tree-lined streets and boutique cafes and shops.

The Schools:

Housing: Apartments and single-family homes, often with more space. Typically $1M–$2M

Good Fit For: Families seeking calm while staying connected to amenities.

Similar Neighborhoods:

  • Newton Centre (Newton, MA)
  • Montclair Center (NJ)
  • Lakewood (Cleveland, OH)

Brookline Village Neighborhood

Healthcare workers and families wanting a village feel with city convenience

The Vibe: Brookline Village is the historic district of the city with beautiful brick buildings and a charming downtown feel. Many locals choose this neighborhood for its proximity to the Longwood Medical Area.

The Schools:

Housing: Condos and apartments from $700K–$1.2M; older single-family homes often $1.2M – $2M+.

Good Fit For: Healthcare workers and families wanting a village feel with city convenience.

Similar Neighborhoods:

  • Bronxville Village (NY)
  • Concord Center (MA)
  • Evanston Downtown (IL).

Chestnut Hills Neighborhood

Professionals and families looking for more space and prestige

The Vibe: Chestnut Hill is a very affluent residential area with beautiful, larger homes and access to the upscale Chestnut Hill Mall. The neighborhood stretches into Newton for some; it is beloved for being home to Boston College. This gives the neighborhood a bit more pep than some of the quieter Brookline areas.

The Schools:

Housing: Luxury single-family homes and townhomes, often $1.5M – $3M+.

Good Fit For: Professionals and families looking for more space and prestige.

Similar Neighborhoods:

  • Wellesley Hills (MA)
  • Scarsdale (NY)
  • Palo Alto’s Old Palo Alto (CA)

South Brookline Neighborhood

Families wanting suburban quiet without leaving Brookline.

The Vibe: South Brookline is the most leafy and suburban of the neighborhoods in Brookline. The homes sit on bigger lots, with more trees and open spaces for the kiddos to run around.

The Schools:

Housing: Larger homes with land, generally $1.2M–$2.5M+.

Good Fit For: Families wanting suburban quiet without leaving Brookline.

Similar Neighborhoods:

  • Belmont Hill (MA)
  • Wilmette (IL)
  • Edina Highlands (MN)