Wychwood Park was established by Marmaduke Matthews, a landscape painter who purchased the land in the 1870's.

The area was then still a rural region on the edge of the city, and Matthews outlined a bucolic community and named it after Wychwood Forest, located near his childhood home in Oxfordshire, England.

In 1874 Matthews built the first house in the society the second house was built in 1877 by his friend Alexander Jardine.

In 1891 Matthews and Jardine document a plan of subdivision for what is now the Wychwood Park neighbourhood.

The area was divided into irregularly shaped lots, with a central park built around a pond and tennis courts designed by the architect Arthur Edwin Whatmough (born 1884, Toronto). Whatmough designed many of the houses that were built in the Arts and Crafts style.

The arrangement of other houses in Wychwood Park started in 1906. In 1917, architect Eden Smith built his own house and later he was working on many designs for houses in the neighbourhood.

In 1985 the area became the first residential zone in Ontario to be granted heritage status.

While the area merged into the city of Toronto in 1909, it remains a private community.