The Governor's Bridge neighbourhood was subdivided in 1912 by William Douglas and Wallace Nesbitt. Douglas and Nesbitt were distinguished lawyers at the Toronto law firm of McCarthy, Osler and Company, and both men were elected president of the Osgoode Legal and Literary Society during their careers.

The actual building of homes in this neighbourhood did not take place until after 1923, when the Governor's Bridge was opened. This bridge spanned a section of the Moore Park Ravine and received its name due to the close proximity of the Lieutenant Governor's residence, which was located where Chorley Park is today.

The same year that the Governor's Bridge opened, Wallace Nesbitt and the estate of William Douglas altered their original plan of subdivision for this neighbourhood. All of the original street names were changed in the new plan. Southview Avenue became Nesbitt Drive, Oakdale Crescent became Douglas Crescent, and Hawthorne Avenue was changed to Governor's Road.

In the early years this neighbourhood was affectionately referred to as "Little Hollywood", because many of the first houses built in Governor's Bridge featured Spanish architectural accents.