The Summerhill Residents Association, incorporated is 1998, was formed in the late 1960's, making it one of the earliest in the city. Our organization consist of a board of director and street representatives which communicate with neighbours regarding issues end events A newsletter is published three to fourth times a year and delivered to all residents within the Summerhill areas.

In the 1870 Toronto was a growing concern and several of the more prominent families had established country estates on the escarpment (the former shores of Lake Ontario) in the area that become known as the Hill. Charles Thompson was a transportation baron in his day (1830-40) and when his venture became successful, he was able to purchase Lot 17, Second Concession from the Bay. Thompson hired the leading architect John George Howard, who had designed a neighbouring home on Woodlawn (35 Woodlawn West) to build his home on the north east corner of the land facing Yonge Street. In 1853 Thompson fortunes began to fade forcing him to sell sections of his estate and built a amusement park. Thompson's Amusement Park was located at the southern end, extending to little creek. Not long after he changed the name to Summer Hill Park and Pleasure Grounds. It attracted man visitors and became popular picnics area. In 1864, the trustees of Thompson's estate subdivided Lot 17 into 59 building lots and two streets were formed: Charles Street now Shaftesbury and Thompson Avenue now Summerhill.
In 1866 Larratt William Smith (1820-1905) bought the property where the Summer Hill house stood. As the family grew 2 children from his first marriage and11 children with his second, the house was expanded to a total of 30 rooms. In 1909 the home was torn down to make room for a subdivision. The memory of Summer Hill estate has been commemorated in two street names Summerhill Avenue and Summerhill Gardens and a in a subway station. The only remaining structure of the estate is the Summer Hill coach house that is located in the far north corner of Summerhill gardens and can best be seen from the corner of the David A. Balfour park.