Charleswood is a residential community and neighbourhood in Winnipeg, Manitoba, Canada. It is located in the southwest of the city and is bordered by the neighbourhoods of Tuxedo to the east, Whyte Ridge to the south, and the Rural Municipality of Headingley on the west. Its boundaries are Roblin Boulevard and the Assiniboine River to the north, Shaftesbury Boulevard on the east, Wilkes Avenue to the south and the Perimeter Highway to the west.