The Upper Beaches: One Of Toronto’s Hidden Gems For Young Families | Pick 5 Edition

October 9, 2025

This week, David heads east to explore one of Toronto’s best-kept secrets: the so-called “Upper Upper Beaches.” Quiet, family-friendly, and packed with character homes at relatively approachable prices, this pocket north of Kingston Rd. and around Victoria Park & Gerrard might just be one of the city’s most underrated areas.

From cozy starter homes under $1M to fully renovated semis with parking and yard space, these five listings show off the charm and value that still exists in Toronto’s east end.

This week’s picks:

  • 03:14 – 28 Pickering St: Starter semi under $1M with character and potential
  • 07:31 – 2311 Gerrard St. E: Renovated 3-bed with huge backyard, great value despite being on a main street
  • 11:35 – 95 Kimberly Ave: Modern red-brick semi, 3 bed 3 bath, beautifully renovated
  • 15:32 – 184 Swanwick Ave: Stylish semi with rec room, backyard deck, and family-friendly layout
  • 19:34 – 106 Malvern Ave: Edwardian 3-bed with parking, staging perfection, and tons of original charm

If you’re in the market for a first home, a family upgrade, or just curious where the hidden value in Toronto still lives, this video is for you.