Real Estate Guide: Leaside-Bennington

Many of Leaside’s residential sections were built in the ’30s, when wainscotting and leaded windows were the height of fashion

  • toronto real estate board overview
  • located in sector: C11
  • average 2012 sale prices
  • all homes: $458,604
  • detached houses: $1,246,333
  • semi-detached houses: N/A
  • townhomes: $221,000
  • apartments: $226,661
  • neighbourhood map: see map

The commercial strip of Bayview from Millwood to Soudan is reason enough to move here. With a comfortable mix of chains and indie shops, this up-market (but not too pricey) bit of high street is the heart of Leaside-Bennington—and all of eastern uptown, for that matter. A relatively new development, Leaside residents numbered just 43 in 1913; in 1929, there were still fewer than 500. Nonetheless, the neighbourhood once had its own train station and an airfield (used for wartime pilot training and the site of Canada’s first delivery of Airmail in 1918). Munitions factories, the Durant Motor Company and Canada Wire and Cable all came and went over the years, mostly between the wars, and each built houses for its workers and executives. Leaside High School (Margaret Atwood’s alma mater) is generally considered one of the better schools in the city. It’s believed that The Handmaid’s Tale is based on the school.

  • Leaside
    165 McRae Drive, 396-3835
  • Northlea Elementary and Middle School
    305 Rumsey Road, 396-2395
  • Leaside High School
    200 Hanna Road, 396-2380
  • Bessborough Drive Elementary and Middle School
    211 Bessborough Drive, 396-2315
  • Rolph Road Elementary School
    31 Rolph Road, 396-2435
  • Bennington Heights Elementary School
    76 Bennington Heights Drive, 396-2310
  • Children’s Garden Junior School
    670 Eglinton Avenue East, 423-5017
  • Maria Montessori School
    125 Brentcliffe Road, 423-9123
  • St. Anselm
    182 Bessborough Drive, 393-5243
  • neighbourhood hot spots

Hollywood Gelato
Though lineups might deter newbies, the natural ingredients that go into this gelato draw aficionados from far and wide. 1640 Bayview Ave., 416-544-9829.

McSorley’s Wonderful Saloon and Grill
A good-time place complete with casual staff, cheap, moderately tasty food and a patio perfectly positioned for enjoying summer days on the strip. 1544 Bayview Ave., 416-932-0655.

Pâtisserie la Cigogne
This small but exquisite shop is a francophilic oasis of butter, cream and flakiness. 1626 Bayview, 416-487-1234.

Sleuth of Baker Street
It’s all detective fiction, all thrillers, all the time in this quirky shop. 907 Millwood Rd., 416-483-3111.