Charleswood was a provincial electoral division in the Canadian province of Manitoba. It was created by redistribution in 1968, and formally existed from the provincial election of 1969 until that of 2019. The riding was in the westernmost tip of Manitoba's capital and largest city, Winnipeg.
Charleswood was bordered to the east by Tuxedo and Fort Whyte, to the north by Kirkfield Park, and to the south and west by the rural riding of Morris.
Charleswood's population in 1996 was 20,262. The riding's character is middle- and upper-middle class: in 1999, the average family income was $70,417, and the unemployment rate was 5.20%. Eleven per cent of the riding's residents are immigrants, with over half being of German origin.
The service sector accounts for 15% of Charleswood's industry, with a further 12% in the retail trade and 11% in health and social sciences.
Members of the Progressive Conservative Party represented Charleswood throughout its lifetime. Sterling Lyon was premier of Manitoba from 1977 to 1981 while representing Charleswood.