In early 18th century, Osterhout Log Cabin was built in Guildwood.
The log cabin is one of Toronto's oldest buildings still standing.

In 1914, the Guild Inn was opened.
Initially a private residence, it later became an art colony, and a hotel.
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.

After Metropolitan Toronto was formed in 1954, taxes on the Guild Inn property increased to the point that the owners Rosa and Spencer Clark decided to sell 450 acres (180 ha) of their property, which became the basis for the Guildwood Village subdivision.
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.
Development started in 1957 with the famous "Avenue of Homes" display of upscale homes.
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. "
Rear-lot parks were modelled after English footpaths as walkways within the community."

The Clarks helped design the entrance gates to the subdivision.
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.
These gates, now called the "Guildwood Gates" still provide a unique and grand entrance to the community at the corner of Kingston Road and Guildwood Parkway.43°44′58″N 79°12′20″W
Guild Park is famous for its historical architectural fragments from the façades of demolished buildings in Downtown Toronto.
Just west of the Guild Inn is Sir Wilfrid Laurier Collegiate Institute.
In early 18th century, Osterhout Log Cabin was built in Guildwood. The log cabin is one of Toronto's oldest buildings still standing.
In 1914, the Guild Inn was opened. Initially a private residence, it later became an art colony, and a hotel. 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.
After Metropolitan Toronto was formed in 1954, taxes on the Guild Inn property increased to the point that the owners Rosa and Spencer Clark decided to sell 450 acres (180 ha) of their property, which became the basis for the Guildwood Village subdivision. 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. Development started in 1957 with the famous "Avenue of Homes" display of upscale homes. 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. "Rear-lot parks were modelled after English footpaths as walkways within the community."
The Clarks helped design the entrance gates to the subdivision. 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. These gates, now called the "Guildwood Gates" still provide a unique and grand entrance to the community at the corner of Kingston Road and Guildwood Parkway.43°44′58″N 79°12′20″W
Guild Park is famous for its historical architectural fragments from the façades of demolished buildings in Downtown Toronto. Just west of the Guild Inn is Sir Wilfrid Laurier Collegiate Institute.
Guildwood