Brookline, MA vs Winchester, MA

Winchester is moderately more affordable than Brookline, with a 10% lower cost of living index. Brookline scores 225 compared to 204 for Winchester, where the US average is 100. This difference means residents of Brookline can expect to pay noticeably more for everyday expenses, housing, and services.

On the housing front, median rent in Brookline is $2,804/month compared to $2,271/month in Winchester — a 24% difference. Home values follow the same pattern: Winchester is more affordable at $1,181,700 median vs $1,233,100.

Median household income in Brookline is $140,631 compared to $218,176 in Winchester (-35.5%). Winchester offers a double advantage: higher earnings combined with a lower cost of living, giving residents significantly more purchasing power. Looking at affordability, residents of Brookline spend roughly 23.9% of their income on rent, more than the 12.5% in Winchester.