Exclusive | Tranquil | Convenient
Bennington Heights is one of Toronto’s most exclusive and expensive neighbourhoods. Over the years, it has been home to 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. The neighbourhood is bordered 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 the area.
Bennington Heights residents can shop for all their household needs at the mall located on the southeast corner of Bayview and Moore Avenues. This mall features a popular grocery store, a large pharmacy, and a bank. Further north on Bayview Avenue, the Leaside shopping district offers an excellent selection of specialty stores, food shops, and restaurants.
Bennington Heights sits on a flat plain atop an escarpment that was once part of the shoreline of ancient Lake Iroquois—the predecessor to Lake Ontario. The 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, located just north of the Cudmore farm, was subdivided in 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, after purchasing number 30 Rosemount Avenue, Weatherhead had the street name changed to Bennington, his wife’s maiden name. The Bennington name was later adopted by Bennington Heights School when it opened in 1950. The neighbourhood has been known as Bennington Heights ever since.
The English Manor-style stone houses in Bennington Heights were built in the 1920s and 1930s. Cottage-style two-storey homes and bungalows followed in the late 1940s and early 1950s. Unlike many other Toronto neighbourhoods, the abundance of natural space creates an environment that allows for large yards and sprawling estates.
