Offers the perfect community for growing families.

Welcome to Winchester

An upscale, beautiful New England town that is perfect for families


Located approximately eight miles north of Downtown Boston, Winchester is a small suburb with the quintessential New England feel. The seventh wealthiest municipality in Massachusetts, Winchester is affluent and offers the perfect community for growing families.

Winchester has its roots in the agri-industrial space. It wasn’t until the early 20th century that it began to develop into the bedroom community it is today. In addition to the Yankee forebears who once populated the region, Winchester’s population was complemented by immigrants that included Irish, African Americans, and Italians. Today, the town has a little over 21,000 residents.

Homes here feature both the traditional New England style that includes a steeply pitched roof and multiple additions, as well as more modern construction and a selection of condos and townhouses. The median price of homes for sale in Winchester is $1.3 million.

What to Love

  • Revolve Consignment Boutique is a high-end consignment store where residents can find designer brands at a deep discount
  • Black Horse Tavern offers diners a cozy environment to enjoy traditional American fare and a full bar 
  • Salone Estetica was named one of the top 10 best hair salons in the Boston area

People & Lifestyle

With its beautifully manicured lawns and upscale restaurants and shops, Winchester is the perfect community for affluent families who want to escape the hustle and bustle of the city. The residents are genuine, close to their neighbors, and diverse in background and occupation.

Winchester has a dense suburban feel where more than 85% of residents own their homes. It’s been ranked as the 20th-best Massachusetts suburb in terms of public schools and the 24th-best suburb in the state to raise a family.

Dining, Entertainment & Shopping

Winchester has a wide collection of high-end locally owned establishments for those who want to eat, shop, or be entertained. Both A’Tavola and Lucia’s are local Italian restaurants where you can grab a glass of wine or a plate of handmade pasta.

For those who want to shop for unique gifts or take a class on drawing, pottery, or painting, Studio on the Common is a perfect choice. This shop sells gifts from socially responsible vendors such as glassware, jewelry, greeting cards, and children’s clothing.

Those looking to grab a quick, tasty bite to eat can stop by D’agostino’s for a deli sub. D’agostino’s also offers trays of lasagna, chicken parmesan, and other Italian favorites for families craving a ready-made, delicious meal.

Things to Do

There’s always something going on in Winchester for active families to enjoy. The farmers' market runs spring through early fall, featuring local vendors who sell fresh produce, gifts, and other hand-made items. The TASTE at the Griffin is an annual benefit for the Griffin Museum of Photography and features tastings from 34 local restaurants and food vendors as an open wine and beer bar and silent auction.

Winchester Town Day is another exciting event in town. Every June, this event features fireworks, exhibitions, games, music, and athletic events. Town Day is celebrating its 40th anniversary and is the perfect way to kick off summer in New England.


Winchester is home to several excellent schools. Top educational opportunities include:

  • Lynch Elementary serves children in grades kindergarten through fifth grade and has been ranked the 19th-best public elementary school in the state
  • McCall Middle School is for students in sixth through eighth grade and received an overall A+ rating from
  •  Harvard University, providing education for both undergrads and graduate students, is only six and a half miles from Winchester and is the #1 university in the world

Work With Us

The Marrocco Group, understand that to attract the appropriate, prospective buyers and to achieve top dollar for every home we list - you must first spend the time creating a marketing plan that no one else can compare to.