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Another popular area that offers a small-town atmosphere, but within Winnipeg's borders, is Charleswood. Bordered by the Assiniboine River to the north, farmland to the south, the Perimeter Highway on the west and the Assiniboine Park and Forest to the east, Charleswood includes several neighbourhoods.

There was little housing in Charleswood before 1920, although it was well known to prairie travelers. Long before Winnipeg was established, an ancient ford across the Assiniboine was a popular feature of the area.

Resident natives and herds of bison originally used the crossing. Years later it became popular with incoming settlers from Europe, who wanted to avoid living too close to the centre of Winnipeg at The Forks.

As recently as 1908, a ferry operated there and a trail leading to the ford was visible up to a few years ago. Settlement of the area occurred slowly from 1920 to 1946.

After this time, development of the area sped up and houses were constructed in the Roblin Park, Marlton and Varsity View neighbourhoods near the junction of Grant Avenue and Roblin Boulevard.

The 1960's saw development in the neighbourhoods now known as Eric Coy, Ridgedale and Westdale.

As Winnipeg grew, the popularity of Charleswood peaked in the 1970's, when thousands of new homes were built, offering an exceptional variety of styles, sizes, lots and prices. By 1980, about 7,500 homes had been built. Still, despite that busy decade of home building, less than five percent of Winnipeggers live in Charleswood.

The neighbourhoods of Vialoux, Ridgedale, Southboine and River West Park offer upscale housing with an air of exclusivity. Recent housing prices range up to $400,000