It is bounded by The Bridle Path on the north, Sunnybrook Health Sciences Centre on the south, Bayview Avenue on the west and Wilket Creek on the east.

The Bridle Path was little more than farmland until 1929, when the Bayview Bridge was constructed across the steep (West Branch) Don River Valley.

Taylor, who designed the Don Mills community, purchased a large plot of land north of the Bridle Path.

In an effort to control who his future neighbours would be, Black took over the company that owned the rolling farmland that was to become the Bridle Path, and set restrictions in place through the North York zoning by-law; only single-family dwellings could be built, and only on minimum lot sizes of 2 acres (0.81 ha).

The hospital was since reorganized into Sunnybrook Health Sciences Centre, and has expanded to encompass much of Bridle Path's southern boundary.

In the 1950s and 1960s, local architects such as James A. Murray, Jerome Markson, Brook and Banz, and Seligman & Dick built many modern houses in the Bridle Path.

Media mogul Moses Znaimer used to call the Bridle Path home, as did computer businessman Robert Herjavec.

Former newspaper baron and convicted felon, businessman Conrad Black was owner of a familial residence until 2016 when he sold the 26 Park Lane Circle, North York for $16.5 million.

[5] "Casino King of Macau" Stanley Ho bought a house in the Bridle Path in 1987 for a then-high $5.5 million.