Charleswood, Winnipeg

Charleswood is a residential community and neighbourhood in Winnipeg, Manitoba, Canada. Situated in the southwest of the city, it is bordered by the neighbourhoods of Tuxedo to the east, Whyte Ridge to the south, and the Rural Municipality of Headingley to the west. The area's boundaries are defined by Roblin Boulevard and the Assiniboine River to the north, Shaftesbury Boulevard to the east, Wilkes Avenue to the south, and the Perimeter Highway to the west.

Historically, the region was known for "The Passage," a ford across the Assiniboine River that served as an essential route for Indigenous and Métis traders and settlers. In 1869, the area was ceded by the Hudson's Bay Company to the Dominion of Canada, becoming a focal point for European settlement. Charleswood was incorporated as a Rural Municipality in 1913 and maintained its independence until 1972, when it was merged with the City of Winnipeg during the city's amalgamation. Since the 1930s, Charleswood has been recognized as "The Suburb Beautiful."

Today, Charleswood is part of the city ward of Charleswood-Tuxedo-Westwood; and is situated within the provincial electoral district of Roblin (formerly the Charleswood electoral district). The community is also served by the Pembina Trails School Division.