Winchester was first settled in 1683, colonized by the Puritan citizens of Charlestown. The first house in Winchester was built along the Aberjona River in 1640. For the next 100 years, there were many land changes, but Winchester ended with land taken from Woburn, Medford, and West Cambridge (now Arlington). By 1798, the population of Winchester was about 200 people. The Black Horse Tavern, which was demolished in 1892, served as an important meeting place for soldiers during the American Revolutionary War.

The character of Winchester was changed when the Middlesex Canal opened in 1803 and the Lowell Railroad supplanted it in 1835. The farming village now had easy access to Boston, strengthening the ties to the city.  In 1835, the Boston and Maine railroad also opened.

In 1850, the Town of Winchester was officially incorporated. The community grew steadily throughout the nineteenth century. Moving into the twentieth century, Winchester started developing more into a bedroom community when former farm lands were bought for housing developments. Following World War II, agriculture started to decline and farms were converted into house lots.