Research amongst former Charleswood residents of the 1940 era concludes these two buildings were located on the corner of Elmhurst Rd and Roblin Blvd. The brick building in the foreground was a grocery store/Post Office and operated by Tommy Chester then later by the Bloomer family. Later it was named "The Willows" and served as a short order restaurant ie hamburgers, pizza, etc.
The house behind the store was also owned by Tommy Chester who rented it to Bill McKennitt's mother and the family (Marnee, Bill & Sharon) lived there for a number of years.
If you're interested or ever lived in the area, send me an email and I'll provide some further history.