Forest Hill, Oakville and Kleinburg offer three very different ways of living. Forest Hill is established midtown prestige, minutes from downtown Toronto. Oakville is lakeside living with a small-town downtown. Kleinburg is a historic village with estate lots and room to breathe.
Forest Hill: established prestige in midtown
Forest Hill was an independent village from 1923 until it joined Toronto in 1967. Early rules required architect-designed homes and a tree in every front yard. Families are drawn by Upper Canada College and The Bishop Strachan School, and by Line 1 subway access at St. Clair West and Cedarvale stations.
Oakville: lakeside luxury
Oakville sits on Lake Ontario between Mississauga and Burlington. Its luxury market centres on Old Oakville, Eastlake, Clearview, Glen Abbey and Bronte, with Appleby College and St. Mildred's-Lightbourn School nearby and GO train service on the Lakeshore West line.
Kleinburg: village charm in Vaughan
Kleinburg grew around a flour mill built in 1847, in wooded hills between two branches of the Humber River. It offers estate homes and new custom builds, the McMichael Canadian Art Collection, and fast access to Toronto and Pearson via the Highway 427 extension.
How to choose
Choose Forest Hill for centrality and schools, Oakville for the lake and train access, and Kleinburg for land and privacy. Buyers in Forest Hill also pay Toronto's municipal land transfer tax; buyers in Oakville and Kleinburg do not.
Alexey Kopeykin, Sales Representative, Zolo Realty Brokerage Inc. Published September 2026. General information, not legal or tax advice; confirm details for your situation.