Barrett Sotheby's International Realty Logo

Winchester MA

Located just 8 miles north of Boston and Cambridge, and with easy access to both cities, you can see why Winchester has grown to become a popular bedroom community. The town has not one but two commuter rail stations that take you to the city 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.  

The town has more to offer than just convenient transport links. Winchester boasts a highly-regarded Winchester Public School system with five elementary schools, one middle school, and one high school catering to over 4600 students from Grades PK - 12. Winchester High School, renovated in 2017, is consistently featured in the list of Top 20 High Schools in the state. Vinson-Owen Elementary School was rebuilt in 2013, and McCall Middle School is expanding to accommodate the growing student population. The Winchester Foundation for Educational Excellence (WFEE) supports the schools by raising funds to support staff and students.

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 a Stop and Shop in town and a Whole Foods Market in Woburn. Winchester also has a hospital with a full 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 or attend 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. Winchester has a thriving senior center, The Jenks, a hub for the over-55’s. The center also hosts events and guest speakers for the whole community.   

A portion of the Middlesex Fells Reservation sits within Winchester’s borders, with access points along South Border Road, a popular spot with families for hiking, biking, and nature walking. Upper Mystic Lake is another beautiful spot within the town, and the Winchester Boat Club offers a prime location from which to enjoy the lakes. Wright-Locke Farm, a community farm offering organic produce, youth, and adult education programs and events, is another gem of a place in town to enjoy the outdoors.

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

Browse Winchester MA Real Estate >>