This grand home was built for William Stewart Darling, rector of Toronto's Church of the Holy Trinity. It was prominently situated to offer spectacular lake views and to overlook a scenic ravine known as "Ben Lamond Park", named for Benjamin Morton and James Lamond Smith, previous owners of the property. Along with nearby "Glen Stewart", also constructed at this time for Darling, the house was most likely designed by his son, illustrious architect Frank Darling. The house was soon purchased by merchant William Monteith; then by William Davies, whose company would contribute to the formation of Canada Packers; and later by Alexander McLeod, a builder who subdivided the dwelling in 1910. Featuring Italianate and Second Empire styles, the Darling house is one of the oldest surviving residences of East Toronto.