The Judge Carleton House is recognized for being a rare example of a pure Queen Anne Revival style house in Woodstock, as well as its association with playwright Judge Carleton.

The Judge Carleton House was constructed in the late 1890s by Daniel Grant, owner of the local carriage making factory. The building is one of the few pure examples of a Queen Anne-style residence in Woodstock. This style can be seen the building's elaborate and asymmetrical façade with a dominant front gable and side tower. The house is also notable for its location in "Victoria Terrace", a historic area that contains many other large and grandiose homes that once housed Woodstock's wealthiest citizens.

For many years, the house was inhabited by Judge Carleton. Carleton was a member of the ‘Woodstock Dramatic Club, one of several amateur theatrical groups that came together over the years. He had a successful career as a playwright and it is believed several of his plays were performed in Woodstock. Most notably, his play ‘The Crimson Wing’ won first prize for the Canadian Prize Play Competition of 1918.