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Leaside-Bennington neighborhood in Toronto
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Leaside-Bennington

Toronto's Quintessential Family Neighbourhood

About Leaside-Bennington

Leaside-Bennington is the gold standard for family living in midtown Toronto. Originally developed as a planned garden community in the 1920s by the Canada Wire and Cable Company, Leaside was once a separate town before being amalgamated into the City of Toronto. That independent heritage lives on in the neighbourhood's strong sense of identity, with the Bayview Avenue shopping strip serving as its de facto main street. Bayview between Eglinton and Millwood is lined with family-friendly restaurants, boutiques, specialty food shops, and the kind of independently owned stores that make a neighbourhood feel like a village. The residential streets are uniformly attractive, with well-maintained brick homes on treed lots and a sense of community pride visible in every front garden. Trace Manes Park, Howard Talbot Park, and the Leaside Memorial Community Gardens provide recreation, while the East Don Parklands offer ravine walks just minutes away. The opening of the Eglinton Crosstown LRT will add rapid transit to an already well-connected neighbourhood.

Key Highlights

Walkability

76/100 - Very Walkable

Transit

Bayview bus (11); Eglinton Crosstown LRT (coming); Leaside bus connections

Vibe

Family-first, village-feel, established

What Makes Leaside-Bennington Special

Bayview Avenue village shopping and dining
Planned 1920s garden community heritage
Trace Manes Park and community gardens
East Don Parklands ravine trail access
Highly rated schools and family programming
Future Eglinton Crosstown LRT connectivity

Liveability Scores

72

Walk Score

Very Walkable

70

Transit Score

Great Transit

66

Bike Score

Bikeable

Local Favourites in Leaside-Bennington

The best-rated spots right in the neighbourhood, from cosy cafes to beautiful parks.

Cafes & Coffee Shops

Achieva Health Cafe

5

47 Laird Dr, East York, ON M4G 3T4, Canada

5 reviews

Starbucks Coffee Company

3.5

301 Moore Ave, East York, ON M4G 1E1, Canada

32 reviews$$

Parks & Green Spaces

Cottonwood Flats

5

Lower Don Parklands, 44 Beechwood Dr, Toronto, ON M4K 2K1, Canada

4 reviews

Nesbitt Park

4.7

93 Nesbitt Dr, Toronto, ON M4W 2E6, Canada

31 reviews

Thomas Hauser Memorial Trailhead

4.6

Crothers Woods Trail, Toronto, ON M4H 1P6, Canada

221 reviews

Crothers Woods

4.6

Crothers Woods Trail, East York, ON M4H 1P6, Canada

882 reviews

Lower Don Parklands

4.6

44 Beechwood Dr, Toronto, ON, Canada

1,159 reviews

Fitness & Gyms

Defy Functional Fitness

5

94 Laird Dr, East York, ON M4G 3V2, Canada

176 reviews

The Flock MMA Academy

5

94 Laird Dr Unit 210, East York, ON M4G 3V2, Canada

27 reviews

ANPT Fitness Inc.

5

94 Laird Dr Unit 210, East York, ON M4G 3V2, Canada

11 reviews

Pilates and Wellness with Dana

4.9

Bayview and Moore Area, 7 Southlea Ave, Toronto, ON M4G 3L8, Canada

10 reviews

Greenwood Jiu Jitsu

4.7

416 Moore Ave suite 102, East York, ON M4G 1C9, Canada

124 reviews

Restaurants

Dhillon’s Karahi

4.9

1213 Bayview Ave, East York, ON M4G 2Z8, Canada

232 reviews

Nigiri-Ya (Leaside)

4.7

897 Millwood Rd, Toronto, ON M4G 1X2, Canada

163 reviews$$

NAAN KABOB

4.6

62 Laird Dr, East York, ON M4G 3V1, Canada

1,681 reviews$$

Olde Yorke Fish & Chips

4.6

96 Laird Dr, East York, ON M4G 3V3, Canada

3,175 reviews$$

La Casetta

4.6

900 Millwood Rd, East York, ON M4G 1X1, Canada

206 reviews

Bakeries

Loblaws Redway Road

4.2

11 Redway Rd, East York, ON M4H 1P6, Canada

1,225 reviews

Loblaws Moore Avenue

4.1

301 Moore Ave, East York, ON M4G 1E1, Canada

1,063 reviews

Tim Hortons

3.8

85 Laird Dr, East York, ON M4G 3T7, Canada

711 reviews$

Happening in Toronto

Upcoming events, festivals, and community gatherings across the city.

All Events
Mar11

Hamilton at the Princess of Wales Theatre

Princess of Wales Theatre

arts
Mar14

St. Lawrence Market Saturday Artisan Market

St. Lawrence Market

communityFree
Mar15

AGO Exhibit: Canadian Modernism Reimagined

Art Gallery of Ontario (AGO)

arts
Mar19

Toronto Tech Meetup: AI & the Future of Work

MaRS Discovery District

techFree
Mar21

Jazz Nights at The Rex Hotel

The Rex Hotel Jazz & Blues Bar

music
Mar28

Improv Comedy Night at Second City Toronto

The Second City Toronto

arts
View All Events

Nearby Neighborhoods

Explore the communities surrounding Leaside-Bennington.

Broadview NorthThorncliffe ParkMount Pleasant EastPlayter Estates-Danforth

Guides & Articles

Helpful resources for anyone exploring Toronto neighbourhoods.

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Real Estate

What to Look for in a Toronto Real Estate Agent (And How to Find One)

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