Winter Hill derived its name from the 120-foot hill that was a notable geographic feature in the late 17th and early 18th centuries. Little remains of the military works built to take advantage of the high ground during the American Revolution or the precise route followed by Paul Revere when crossing Winter Hill during his famous midnight ride. However, the neighborhood has no shortage of historical buildings.
Several structures in Winter Hill have been listed in the National Register of Historic Places. These include the Otis-Wyman House, the Susan Russell House, the Peter and Oliver Tufts House, the H. Warren House, the Downer Rowhouses, the Broadway Winter Hill Congregational Church, the Charles Adams-Woodbury Locke House and the Adams-Magoun House. Of more recent historical significance is an apartment occupied by a Harvard Law School student named Barack Obama from 1988 to 1991.
Magoun Square lies to the west of Winter Hill, with Medford Street forming the neighborhoods approximate southern border and McGrath Highway providing its eastern boundary. However, the neighborhood cannot be succinctly defined by precise north-south and east-west roadways.
Housing in Winter Hill is a mix of upscale single-family homes, apartments that range from economical units to luxury townhomes. Rents and property values have increased in recent years, but they are currently on a par with average prices throughout the balance of Somerville.
The Winter Hill neighborhood is known as the home of some of the best restaurants to be found in the Boston metropolitan area. Options range from classic pizzerias and delicatessens to casual cafes and fine-dining establishments.
Downtown Boston and Tufts University are a short bus ride away from Winter Hill. The convenient location, coupled with housing available in a wide range of prices, have made the Winter Hill neighborhood a popular choice for many in the Somerville area.