The area now known as the Kingsway is a combination of three distinct areas: The neighbourhood was first developed by Etobicoke lawyer Robert Home Smith who purchased the old King's Mill (which was renamed the Old Mill, reopening as a high-end Inn) and began developing land in the early 1900s.

The Kingsway emerged from Home Smith's vision of the ideal community and was mostly inspired by the Garden City principles, which were originally conceived in parts of England and the United States during the late 19th and early 20th centuries.

"Tastefully appointed" traditional homes were sited on well-treed and winding streets, to create an air of a wooded retreat.

Home Smith also decreed that no owner could build a house without the approval of his staff, and he developed strict regulations against the cutting of trees.

Smith also created the Old Mill Restaurant in the community, whose Tudor Revival facade and well-appointed interior inspired much of the English design in the Kingsway.

In the 1950s a series of accidents led to the creation of a highway style interchange at Royal York and Dundas, cutting the neighbourhood from the much older community of Islington to the west and the street the Kingsway from its extension to the north.

The stretch of Bloor east of Prince Edward Drive near the entrance to the street the Kingsway and the Old Mill saw the construction of many apartment buildings in this period.

The community in the Kingsway has been very successful in preserving the style of housing and atmosphere of the neighbourhood as intended by Robert Home Smith; the area contains many of Etobicoke's most prestigious addresses.

Prince Edward, a two-lane arterial roadway, runs north–south from Berry Road to Dundas Street West.