The log cabin is one of Toronto's oldest buildings still standing, although its exact date of construction is unknown.

From 1941 to 1947, the inn was leased by the Government of Canada as a base for the Women's Royal Naval Service, HMCS Bytown II, and later a military hospital.

The Clarks remained involved with the development of the subdivision, in its design and layout to preserve as many trees in the area as possible.

[3] The community introduced a number of new ideas in subdivision design, including winding roads and cul-de-sacs to reduce through traffic, and underground power and phone lines.

After most of Toronto's Stanley Barracks (New Fort York) was demolished in 1953, its gates were salvaged and re-erected at the entrance to Guildwood Village.

In addition to TTC routes, GO Transit's commuter rail service may be accessed from Guildwood GO Station.

The eastern end of the roadway splits north, and east, with the northern portion forming Morningside Avenue.