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Wychwood Park was founded as an artists' colony in the late nineteenth century, as a private project by painter Marmaduke Matthews and businessman Alexander Jardine.  The area was then still a rural region on the edge of the city, and Matthews planned out a picturesque community that he named after Wychwood forest in Oxfordshire, England.

Painting of Wychwood Park by Marmaduke Matthews, c. 1895
The land was divided into irregularly shaped lots, with a central park built around a pond and tennis courts designed by the architect Arthur Edwin Whatmough, and there were careful restrictions upon what could be built in the community. Whatmough designed many of the houses that were built in the Arts and Crafts style. Some of the others were designed by prominent architect Eden Smith, including his own home at number 5 Wychwood Park, which he built around 1906.

One of Toronto's ravines ran through the heart of the neighbourhood, and this was preserved as parkland. Taddle Creek ran through the ravine, and it was dammed to create a large pond in the middle of the park. This is now one of the few places in the city where Taddle Creek is still visible above ground.

While the area was amalgamated into the city of Toronto in 1909, Wychwood Park remains a private community, with approximately sixty houses. Wychwood Park's private roads and amenities are paid for by the local residents, and the community is managed by an executive council.

Wychwood Park is one of Toronto's more expensive neighbourhoods, with house prices well over two million dollars. In 1985, Wychwood Park became the first residential zone in Ontario to be granted heritage status when it was designated as a Heritage Conservation District under the Ontario Heritage Act.

The Wychwood Barns site, a former Toronto Transit Commission streetcar maintenance facility located to the north of Wychwood Park, was transformed into a community park in 2008. The original maintenance buildings (the St. Clair Carhouse) on the site were converted into a mixed-use community facility at that time. source: wikipedia