Insurance in Winchester, MA

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Winchester, Massachusetts is the 7th wealthiest town in Massachusetts. Located 8 miles north of Boston, it is largely a residential suburb with an easy commute into downtown Boston. It is located in Middlesex County and its neighbors include Woburn, Stoneham, Medford, Arlington, and Lexington.

Winchester covers 6.3 square miles, nearly 4% of which is water. The town has a variety of waterways including the Aberjona River, the Mystic Lakes, Wedge Pond, and Winter Pond. Sucker Brook and Sanchem Swamp make up additional water areas in the town.

Insurance Winchester MA

The population of the town is over 21,000 people. As the town grew, it attracted immigrants from a variety of backgrounds including Irish, Italians, and African-Americans, leading to the diverse population Winchester enjoys today.

Winchester has two stops on the MBTA Lowell Line commuter rail, providing residents with easy access to North Station in Boston. Several bus lines also operate in Winchester for access to other local areas. With Interstate 93 nearby, residents can easily get to any area within the region.


Winchester was originally purchased from the Native Americans in 1639 as part of Charlestown. Known as Waterfield or Black Horse Village, it was settled by Europeans in 1640. The town did not incorporate until 1850, when the Whig party sought to separate from the surrounding Democratic towns. When the town was granted incorporation, it took land from Woburn, Arlington, Medford, and Cambridge.

In its early days, the town was largely agricultural, but as was the case with many Massachusetts towns, the railroad allowed it to thrive with industry as well. The two best-known industries in town were the Beggs and Cobb tannery and the Winn Watch Hand factory.

Today, Winchester is largely residential, with residents commuting into Boston and other cities for work. There has been a recent push towards saving energy and becoming a Green Community, a designation that the town earned in 2010 by the Massachusetts Department of Energy Resources. With solar power installation, state grants, and other programs, it has become a model for environmental friendliness on the municipal level.

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Insurance Winchester MA


Winchester has a variety of recreational opportunities for its residents, making it a highly desirable place to live. From a charming duck pond to a private country club, there are many activities to choose from.

Part of the Middlesex Fells Reservation lies in Winchester. This large Massachusetts state park area has over 100 miles of trails for hiking, biking, and other activities that are open to residents and visitors year-round.

Other activities include:

  • Wedge Pond, which a popular beach and splash park, and annual fishing derby
  • The Packer Tennis Courts
  • The Mystic Lakes, which are open for swimming and boating in summer months
  • The Winchester Boat Club, a private club operating on the Mystic Lakes
  • The Winchester Swim and Tennis Club
  • The Winchester Country Club
  • The En Ka Fair and Exchange
  • The Duck Pond

Winchester, Massachusetts has much to offer its residents, from a convenient location to enjoyable recreational opportunities. The town has grown from its agricultural roots to become a thriving and sought-after residential suburb, ranked as one of the top in the nation.


For quotes or questions, reach out to the experts at Scotti Insurance Agency. We’ll be happy to assist you!

Scotti Insurance Agency

Scotti Insurance Agency

19 Mount Vernon Street
Winchester, MA 01890