“Hart House in Winter” was painted in MacDonald's typical style using quick yet intentional brush strokes done in an impressionistic style. MacDonald deliberately chose purples, reds, and warmer tones to keep the painting soft and welcoming in spite of being a winter scene. Hart House stands proudly through the barren trees and would have been a welcome sight to a Torontonian walking in the cold.
Although the artist attended the Ontario College of Art, Hart House was open to the public and a prominent building downtown, not far from OCA. Not only would Hart House have been important to Toronto culturally, but it was also physically dominant at a time when Toronto's downtown area was less developed. University of Toronto's historic Hart House was built during the Gothic Revival era of architecture and designed with the intention of providing an environment that would encourage balanced and productive members of society.