Bennington Heights
History:
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.
Overview:
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.
Lifestyle:
Bennington Heights residents can shop for all of their household needs at the mall located on the south-east corner of Bayview and Moore Avenues. This mall features a popular grocery store, a large pharmacy and a bank. Further north on Bayview Avenue is the Leaside shopping district which contains an excellent selection of specialty stores, food shops and restaurants.
The Evergreen Brick Works situated in the Don Valley ravine off the Bayview Extension seems like a world away from everyday life in Toronto. Evergreen Brick Works is Toronto’s newest Green initiative and it is attracting visitors of all ages from all parts of the city who are gathering here to shop at the popular farmers market, hike along nature trails and to learn about Toronto’s urban nature.
Homes:
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, culs-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.
Recreation:
Bennington Park, located off of Bayview Heights Drive, has a nice view of the Don River Valley. This park is the home of the Bennington Heights Tennis Club which has two tennis courts. Next to the park is the Bennington Heights School. The school’s recreational facilities include a soccer field, two baseball diamonds, and a large children’s playground. Evergreen Gardens Park, off of Moore Avenue also has a children’s playground. Nature lovers and fitness enthusiasts can access the Moore Park Ravine walking trail from Moore Avenue east of Hudson Drive or from the Bayview Avenue extension. The Moore Park trail is a remnant of the former Belt Line Railway, a commuter train that serviced Toronto in the early 1890’s.
Transportation:
The Moore Avenue bus connects passengers to the St. Clair station on the Yonge-University-Spadina subway line. Motorists can hop on the Bayview extension which will usher them downtown in minutes or provide access to the Don Valley Parkway and a network of connecting highways leading into and out of the city.
Featured Listings
Bennington Heights Stats
Walkability:
Medium
Bikeability:
High
Public Transit:
Low
Affordability:
Low
Greenspace:
High
Recreation:
High
Legend: Low, Medium, High
Commute Times
* All commuting times provided are approximate times only. Commute times may increase or decrease depending on where you live within the neighbourhood and the time of day i.e rush hour versus off hour commutes. Time estimates to public transit are based on walking distance or bus line connection whichever is quicker. All other commute times on the chart above are based on drive times.
School Guide
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Toronto School Resources

Editor’s Note. BEFORE MOVING INTO, BUYING OR RENTING A HOME, PLEASE CONTACT THE SCHOOL YOU ARE CONSIDERING BY PHONE to ensure your home is within the designated boundaries and that your child is age appropriate. WE CANNOT BE HELD RESPONSIBLE FOR ANY MISINFORMATION REGARDING SCHOOL ENROLLMENT SO DO NOT ASSUME that your child can automatically attend a specific school or specialized program until you have official confirmation from that school. Please visit the school board web sites for more information.