Christian Matthews : Toronto, Leslieville and East York Real Estate Agent

Woodbine Gardens is bordered by Victoria Park to the east, St. Clair East to the north, O’Connor to the west, and Taylor Massey Creek to the south. When you drive through Woodbine Gardens with its hills and dales and winding and sloping crescents it is easy to envision the fact that this neighbourhood was once an attractive golf course.

The neighbourhood of Woodbine Gardens has its origins in the Woodbine Golf and Country Club which once occupied the picturesque hilly landscape on which this neighbourhood now sits. In 1932, Woodbine Bridge (currently part of O’Connor Dr.) was built over the Taylor Creek Ravine, which enabled a better connections to the area. This connection would eventually lead to the development of this area, which has an interesting story behind it.

Toronto born hollywood star Mary Pickford donated the proceeds of the sale of her family home to the building of the first bungalow in this future East York neighbourhood. A raffle for the Pickford bungalow occurred in 1943 with the proceeds going to the Canadian war effort. Most of the rest of the development of Woodbine Gardens occurred in the 1950s, with a pretty heavy handed approach to building by burying waterways and levelling many of the plentiful hills.