Massachusetts Living Index
Winchester
Greater Boston · pop. 22,970
Picture-postcard downtown next to Mystic Lakes with a 24-minute train to North Station.
Family SuburbCommuter Value
Livability Index
69
/ 100
Ranks #34 of 194 MA towns
The numbers
Median home
$1.38M
6× household income
Household income
$230k
ACS median
Commute to Boston
24 min
peak driving
Population
22,970
5-yr trend 73/100
How Winchester scores
Schools
96
Safety
95
Walkability
40
Transit
29
Biking
44
Dining
60
Nightlife
38
Arts & Culture
50
Green Space
72
Diversity
68
Climate
73
The honest read
Best for
Commuters who want a charming town center.
The tradeoff
Inventory turns over slowly, and bidding wars are common.
Compare on your terms
These scores reflect a neutral weighting. Your priorities are not neutral. Open the full atlas to tune schools, walkability, affordability, commute, and seven more dimensions, and see where Winchester lands for you.
Nearby towns
Bordering and adjacent Massachusetts towns near Winchester.
Popular comparisons
Common head‑to‑heads people search when looking at Winchester.
Want my honest read on Winchester?
I'm Gary Fikes, a licensed real estate agent at MP Signature Realty and the curator of this site. Tell me what you're looking for and I'll reply personally within 1 business day. No auto-dialer, no spam, no resale.