Charleswood is a residential community within the city of Winnipeg, Manitoba, Canada. It is located in the southwestern part of the city, and is bordered by the Assiniboine River to the north, the Rural Municipality of Macdonald to the south, the Rural Municipality of Headingley on the west and the Assiniboine Park and Forest to the east. Until it joined with the City of Winnipeg in 1972 it was a separate municipality known as the Rural Municipality of Charleswood.