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Living in Winchester MA

Lake view

Winchester, MA is a lovely suburb just 8 miles North of Boston. It is considered a bedroom community due to the number of residents that commute to Boston for work, whether it be by car or the MBTA Commuter Rail. Residents enjoy a quiet community with easy access to all that the city has to offer. The center of Winchester, Winchester Center, is made up of beautiful Victorian architecture and a collection of small shops and businesses. This is a great attraction for shopping, dining, and meeting up with family and friends. Located on the bank of the Aberjona River, the center is surrounded by brick walkways and lanterns with a Town Common, which typifies New England. Read more about the town of Winchester in Northshore magazine here

Winchester Schools

Winchester public schools have long been known for their dedication to excellence. The school system provides an environment that supports challenging, yet nurturing, academic achievements, as well as emotional and social development. Public schools include:

Winchester Hospital

Winchester is proud to have its own award winning hospital, Winchester Hospital. It is the leading provider of quality healthcare with attention to women’s health, obstetrics, and oncology. The hospital’s top-of-the-line pediatric care unit is affiliated with Boston Children’s Hospital. Winchester Hospital won the award for nursing excellence in 2003 and was the first community hospital in Massachusetts to achieve this prestigious recognition. Less than 3% of US hospitals ever achieve this status. The hospital was also named one of the Boston Business Journal’s Best Places to Work in 2006, and it has been on that list for four consecutive years.

Things To Do in Winchester


Check out some of Winchester’s best spots for a bite to eat. From fine dining to casual fare, Winchester has a variety of restaurants to choose from! If you are looking for an upscale experience, discover Lucia Ristorante and A Tavola. A casual spot for lunch or dinner First House Pub. Looking for a great cup of coffee check out the Fuller Cup and for a hearty sandwich head to D'Agostino's Delicatessen. Gloria’s Pizzeria is a spot for Italian comfort food. For all Winchester restaurants, click here!

Outdoor Recreation

The Town of Winchester is blessed to be surrounded by one of the most magnificent reservations around, Fells Reservation. With miles of walking and biking trails, Fells Reservation is a popular spot to watch the season change and take in spectacular scenery. The Aberjona River is another natural feature that enhances the beauty of the town. This meandering waterway defines the town and the waterfall in the center is part of this landscape.

Some of Winchester’s most desirable homes have stunning views of Mystic Lakes, a waterway consisting of Upper Mystic Lake and Lower Mystic Lake. From the terraced lawns of Everett Avenue to the privacy and beauty of Myopia Hill with views of the lake and Boston, Mystic Lakes are a town treasure.

Houses of Worship

First Baptist Church, First Church of Christ Science, First Congregational Church, Second Congregational Church, Parish of the Epiphany, Hope Christian Church, International Family Church, Temple Shir Tikvah, Crawford Memorial United Methodist Church, St. Eulalia’s Church, St. Mary’s Church, Winchester Unitarian Church.


Winchester Family Action Network (FAN) – FAN is a Winchester based non-profit organization offering support for families with infants and young children. FAN organizes playgroups, events, educational programs and much more.

Winchester Seniors Association - The Winchester Seniors Association is a not-for-profit volunteer corporation of, by, and for people 55 years and older. Their mission is to improve the quality of seniors' lives through participation in a wide variety of social, educational, and recreational activities operated by the private not-for-profit Jenks Center. 

Winchester MA Real Estate

Begin your Winchester, MA real estate search below. If you have questions about the town or Winchester or the Winchester real estate market, contact The Shanahan Group today!

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