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.

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.

[1] In 1869, the area was ceded by the Hudson's Bay Company to the Dominion of Canada, becoming a focal point for European settlement.

[1] In 1899, a highway, now Roblin Boulevard, was surveyed along the south side of the Assiniboine River[1] Patrick H. Kelly (1847–1940) is widely regarded as the founder of what is now Charleswood.

of Assiniboia and Parishes of Headingley and St. Charles, while excluding territories held by the Town of Tuxedo and the City of Winnipeg.

The local economy at the time was chiefly agricultural with dairy and poultry farms, market gardens, and mink ranchers.

[11] Following World War II, it became popular with European immigrants who wanted to avoid living too close to the centre of Winnipeg.

Development of the area increased, and new houses were constructed in the Roblin Park, Marlton, and Varsity View neighbourhoods.

A ferry service was in operation in the region as late as 1958, and a trail leading to the ford was visible until fairly recently.

With Headingley seceding in 1992, the former municipalities on the north and south sides of the Assiniboine River—Charleswood and St. James-Assiniboia, respectively—were reunited as the Assiniboia Community.

[17] Charleswood is host to the main campus of Canadian Mennonite University, which includes the former Manitoba School for the Deaf.