The Bennington Heights neighbourhood is situated on a flat plain of land, on the crest of an escarpment which thousands of years ago had been part of the shoreline of ancient Lake Iroquois – the forerunner to Lake Ontario.  

This area was first settled in the 1870s by John Cudmore and Daniel Ryan, who operated successful market gardens on their respective properties. The Cudmore farm was subdivided for residential development in 1889 and later re-subdivided in 1912. Daniel Ryan’s property, which was located just to the north of the Cudmore farm was subdivided into stages between 1891 and 1946. 

The first resident of the present-day neighbourhood was Thomas Weatherhead, a solicitor for the East York School Board. In 1925, when Weatherhead purchased number thirty Rosemount Avenue he had the Rosemount street name changed to Bennington, which was his wife’s maiden name.

The Bennington name was also adopted by the Bennington Heights School when it opened in 1950. This neighbourhood has been referred to as Bennington Heights ever since. 

Bennington Heights English Manor stone houses were built in the 1920’s and 1930’s. The Cottage style two-storey homes and bungalows were built in the late 1940’s and early 1950’s. 

Bennington Heights’ winding roads, cul-de-sac and ravine properties all add to the charm of owning a home in this neighbourhood. With so much nature at your doorstep don’t be surprised if you spot a fox gingerly taking an afternoon stroll through Bennington Heights as I had the pleasure of witnessing while touring this neighbourhood.

Bennington Heights is one of Toronto’s most exclusive and expensive neighbourhoods. Over the years it has been the home of many prominent Torontonians including author Margaret Atwood, whose highly acclaimed novel Cat’s eye, is loosely based on her childhood growing up in Bennington Heights.  

Bennington Heights is bound on two sides by the bluffs of the Don River Valley ravine and on the north by Mount Pleasant Cemetery. These natural barriers help preserve the peaceful tranquility of this neighbourhood.