So, You Want to Live in Winchester?
Looking for a family-friendly town with a vibrant arts scene just a quick ride from Boston? Pack your bags—you’re making a beeline for this northern ’burb.
Photo via Getty Images
1. Pick Your Price Point
It isn’t cheap to live in Winchester (population about 23,000): Last year, the median sale price of a single-family home here was $1.5 million. And if you find a place you love, be sure to act fast, as properties typically sell after 20 days on the market. Listings range from spacious historical beauties for $1.6 million to two-bedroom condos in downtown Winchester priced around $700,000.
2. Plot Your Commute
Given that Winchester is only 9 miles north of Boston, most 9-to-5ers choose to drive into the city, but be aware that the normally 30-minute ride pushes closer to an hour during peak times. To avoid traffic, the train from Wedgemere commuter-rail station will get you to North Station in just over a half hour.
Photo via Creative Commons/Aslam Karachiwala
Photo by Demetri Productions LLC / Listing agent: Nan Shanahan
3. Take in the Vibe
Outdoor enthusiasts will find plenty to do in Winchester—from kayaking and bike riding around Mystic Lakes on the town’s southern border to hiking and mountain-biking on the wooded hills of the Middlesex Fells Reservation. Winchester’s downtown, meanwhile, is full of classic charm, with a diverse array of boutiques, dessert spots, and the beloved indie bookstore Book Ends, a town staple since 1984.
4. Check out the Culture
Incorporated in 1850, Winchester is dedicated to preserving its original New England character and architecture. The town also has a vibrant arts scene—so much so that the Massachusetts Cultural Council designated downtown Winchester as a cultural district in 2019. You can take a stroll through the Griffin Museum of Photography, catch some live music at Winchester Porchfest every summer, or sign up for a pottery class at Studio on the Common to try your hand at throwing.
Photo via Creative Commons/Lee Wooten
Photo by Studio on the Common
5. Scope out the Schools
The schools in Winchester are renowned for their high test scores and low student-teacher ratio of 12.3 to 1. There are five public elementary schools, one middle school, and one high school in the town, which was ranked number 18 in our 2024 list of Greater Boston’s best public high schools. There are also a handful of private schools, including the Acera School, serving students from kindergarten through 9th grade with STEAM-focused education and leadership development.
First published in the print edition of Boston magazine’s November 2024 with the headline, “So You Want to Live in… Winchester.”
