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Winchester MA

Living in Winchester MA

The city of Winchester MA is a popular bedroom community, just 8 miles north of Boston and Cambridge. Neighboring towns of Winchester include Woburn, Stoneham, Melrose, Malden, Medford, Arlington, and Lexington.

The town has two commuter rail stations that take you to Boston in less than 20 minutes. Winchester also has direct access to the I-93 for a short drive into Boston and Cambridge. There are also bus routes that connect to the Red Line at Alewife, North Cambridge, and the Orange Line at Wellington Station in Medford.  

Things to Do in Winchester

The town has a lot more to offer than convenient transport links. The picturesque town center with the beautiful common flanked by the striking white church steeple gives the town a quintessentially New England feel. Boutique stores and salons sit alongside popular favorites such as Starbucks and CVS for essential purchases. There are plenty of dining options, including The Waterfield Kitchen (part of the Serenitee Restaurant Group), the locally owned Black Horse Tavern, and Lucia’s Ristorante (sister restaurant of the North End favorite). For groceries, there is a Stop and Shop in town and a Whole Foods Market in Woburn. Winchester also has a hospital with an emergency room and many world-class facilities. 

One of the most stunning views of the town is looking across the Aberjona River towards the Winchester Public Library and the Town Hall. People gather on the lawn behind the library to enjoy Town Day and the fireworks in June and the annual Halloween Parade, organized by the parent group Family Action Network of Winchester. Across from the Town Hall, the En Ka Society brings the fair to town for a weekend in May, attracting the crowds since 1935 for this annual tradition. The Jenks, a thriving senior center for the over-55’s, hosts events and guest speakers for the whole community.   

A portion of the Middlesex Fells Reservation sits in Winchester, providing access points along South Border Road for families to enjoy hiking, biking, and nature walking. Upper Mystic Lake is another beautiful spot in town, and the Winchester Boat Club offers a prime location to explore the lakes. Wright-Locke Farm is a community farm offering organic produce, youth, and adult education programs and events, and outdoor activities.

With all that Winchester has to offer, it’s no wonder property is in high demand.

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Winchester Schools

The town boasts the highly-regarded Winchester Public School system, featuring one preschool, five elementary schools, one middle school, and one high school. The Winchester Foundation for Educational Excellence (WFEE) supports the schools by raising funds to support staff and students.

Winchester High School
McCall Middle School 
Ambrose Elementary School
Lincoln Elementary School
Lynch Elementary School
Muraco Elementary School
Vinson-Owen Elementary School 
Winchester Preschool