Winchester MA - Family Friendly with Classic New England Charm

In the 1970’s, Winchester was ranked as one of the top fifteen suburbs in the nation by the US Census. A sleepy bedroom community located just a fifteen minute train ride from Boston, it has changed little over the past few decades.

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With its quaint downtown, brick sidewalks, the common, and Wedge Pond, Winchester exudes classic New England charm. The town has fought the presence of chain establishments, and therefore most of its commerce is centered downtown, with unique restaurants, shops, bakeries, and boutiques. On a trip to Winchester center, D’Agostino’s deli, bakery La Patisserie, and Thai restaurant It Rains Fishes are can’t misses. Nick and Lizzie’s is a favorite shop among kids, and upscale boutiques French Lessons and Mad About Shoe merit a visit, even if only for window-shopping.

As one of the more affluent suburbs in the Greater Boston area, the median household income is over $100,000 and the average home price is approximately $800,000. Only 2.8% of residents are below the poverty level, compared with 9.9% in the state of Massachusetts (Citi-Data.com).

Winchester attracts many young families, as well as those who have lived there for generations. The pride and joy of Winchester may well be its school system. With five elementary schools, McCall Middle School, and Winchester High School, Winchester offers an excellent public education. Winchester’s public schools consistently rank near the top for MCAS scores. Winchester High School has over a 99% graduation rate, and approximately 85% of graduating seniors go on to four-year colleges (NEASC).

Winchester is a close-knit, family-oriented community, with annual events such as Town Day and the ENKA Fair. In the summer months, many residents unwind at the Country Club, the Boat Club, or the Swim and Tennis Club.

This small town of approximately 20,000 residents (2000 census) has had no shortage of famous residents, including cellist Yo-Yo Ma, Olympic gymnast Alicia Sacramone, Brad Whitford of Aerosmith, and Governors of Massachusetts Edward Everett, Samuel W. McCall, and John Volpe.