Smart Movers Club

    Moving to Winchester, MA

    Is Winchester a good place to live?

    Watch Winchester

    Winchester ranks #12 of 65 Massachusetts cities with 25,000+ people on the Smart Movers livability score (67/100), which weighs home affordability, unemployment, education and population growth. Population grew 0.2% in the latest Census year.

    Median home value
    $1,181,700
    +2.8% vs prior year
    Median rent
    $2,271
    per month
    Household income
    $218,176
    median
    Unemployment
    3.0%
    lower is better

    Cost of living in Winchester

    The median home value in Winchester is $1,181,700 and median rent is $2,271 a month, against a median household income of $218,176. Homes cost about 5.4× a year of income (under 3× is considered affordable).

    Winchester crime rate

    City-level FBI figures vary by agency; across Massachusetts the 2025 rate was 301 violent and 1,036 property crimes per 100,000 people — #42 highest of 50 states. The full report breaks down local trends.

    Moving to Winchester, MA

    Winchester has about 22,862 residents, 3.0% unemployment and 28% of adults with a bachelor's degree or higher.

    Compare Winchester with

    Winchester vs BostonWinchester vs WorcesterWinchester vs SpringfieldWinchester vs CambridgeWinchester vs LowellWinchester vs BrocktonWinchester vs QuincyWinchester vs Lynn

    More: Where to move in Massachusetts · Best counties in Massachusetts

    Sources: U.S. Census Bureau ACS 5-year estimates (2023, compared with 2022); FBI Crime Data Explorer.

    Home listings, local news, migration, schools, resources and the Smart Movers Grade & Verdict.

    See the full Smart Movers Club report