Bennington Heights: A Hidden Gem in Toronto

Bennington Heights stands out as one of Toronto’s most sought-after neighbourhoods—and it’s easy to see why. Tucked within the Don River Valley ravine, this exclusive pocket offers a rare combination of tranquility and natural charm. The area is known for its stately detached homes, pristine gardens, and gently winding streets. A stroll down Bennington Heights Drive instantly sets it apart from typical residential areas.

Location
Bennington Heights is a small, refined community closely connected to its prestigious neighbour, Leaside. It’s bordered by Mount Pleasant Cemetery to the north, the railway line to the south, and the Don River Valley to the west—adding to the area’s lush, scenic ambiance.

Schools
Incredibly notable for young families is Bennington Heights Elementary School. Located immediately south of Bayview and Moore Avenues, the school has been serving the Bennington Heights Community since 1950, and is one of the city's best public schools providing educational excellence in a small school environment.

Other schools in the area include:
- Bessborough Dr. Elementary and Middle PS 
- St. Anselm Catholic School
- Our Lady of Perpetual Help Catholic Elementary School 
- Junior Academy, private (JK to Grade 8)
- Leaside High School
- Crescent School (private boys' school grades 3 to 12)

Local Conveniences
Residents enjoy access to a conveniently located shopping plaza at Bayview and Moore Avenues, offering essentials such as groceries, pharmacies, and banking services. For boutique shopping and upscale finds, the nearby Leaside retail area is home to a variety of specialty stores.

The Evergreen Brick Works, nestled in the Don River Valley, is another local highlight. This environmentally conscious destination features one of this city's largest and most vibrant farmers markets with vendors selling locally sourced produce and handcrafted goods.

Lifestyle & Recreation
Bennington Heights is ideal for those who enjoy nature and outdoor activities. Evergreen Brick Works isn’t just a marketplace—it’s an educational and recreational hub with nature trails, outdoor learning spaces, and engaging eco-programs for all ages.

The neighbourhood also boasts beautiful green spaces like Bennington Heights Park, which features scenic valley views and a tennis club with two courts. Families will appreciate Evergreen Gardens Park for its well-equipped playground and easy access to the Moore Park Trail.

Sports and Fitness 
Bennington Park is home to the Bennington Heights Tennis Club and to Bennington Heights School which has a soccer field, two baseball diamonds, and a large playground.  Nature lovers and fitness enthusiasts can also access the Moore Park Ravine walking trail - a remnant of the former Belt Line Railway that serviced Toronto in the early 1890s.
 
Getting Around
Public transit is easily accessible, with bus service along Moore Avenue connecting to St. Clair Station on the Yonge-University-Spadina subway line. Drivers benefit from quick access to the Bayview Extension, which links directly to the Don Valley Parkway, making travel throughout the city seamless.