995 Avenue Road was constructed in 1925/1926. It was one of the very first properties built on this stretch of Avenue Road.

The first occupants were John Lennox Best, Walter W. Hurd, and their families. John Lennox Best was originally from Collingwood. The Bests and Hurds were related through the marriage of John Lennox Best and Lenore Hurd. John Lennox Best died at home quite young - only aged 35 - on 31 December 1926. Prior to his death, he was the Manager of D. M. Best & Company - a piano equipment (hammers, strings, etc.) company based at 520 King Street West, Toronto. D. M. Best & Company was owned by David M. Best. This was during a period when Toronto was one of the leading piano manufacturing cities in the world.  Comparatively, Walter W. Hurd was a builder by trade.  

The newspaper articles do not mention how or why John Lennox Best died so young (on New Year's Eve nonetheless). However, later obituaries identify that members of the Hurd family were still living at 995 Avenue Road as of Lenore Best's (née Hurd) death in 1969.