As described in "Beyond Green Gables”, "Chestnut Park Road in Rosedale, Toronto still retains its Edwardian panache with globe lights set along winding curbs of imposing private residences.”

Rosedale is one of the oldest and wealthiest suburbs just north of downtown Toronto.  It is known as the area that contains the most “old money” and has housed several famous Canadians, including Ken Thomson – Canada’s wealthiest man at the time of his death in 2006.

Set amongst the ravines that compose the neighbourhood’s boundaries are many winding streets.  These can be attributed to Mary Jarvis – the wife of Sherriff William Jarvis – Rosedale’s first settlers in the 1820’s.  Mary loved to horseback ride and the trails she made marked the beginnings of the neighbourhood’s roads.  The name of the suburb was inspired by the many wild roses that grew on the hillside of the Jarvis estate.

The neighbourhood provided the perfect setting in which to establish the wealthy environment Anne entered while teaching in Kingsport.

Source: Beyond Green Gables