Built in 1929, this palatial Forest Hill spread was designed by architects Sproatt and Rolph, known for such landmarks as the Royal York Hotel and the College Park Eaton’s. Their client, philanthropist and steel magnate Sigmund Samuel, moved in as the Depression began, and bequeathed the house to the province to be used for visiting dignitaries. The government sold it without any luminaries ever stopping by.

Where: 104 Forest Hill Road
Price: $12 million
Bedrooms: Seven, including a nanny’s room, all ensuite
Bathrooms: 11, including two bathroom–change rooms for the pool
Size: 18,000 square feet on four floors
Current owner: Michael Bregman, former boss of the Second Cup chain, now a businessman-at-large, and his wife Barbara (known for her volunteer work with Mount Sinai)