Shipp first entered the family construction business in 1945 at the age of 19, immediately upon graduation from high school.

[4] In the fall of 1957, Thomas Laird Kennedy, who briefly served as Premier of Ontario, asked Harold Shipp to succeed him as his choice as the Conservative candidate for the region of Peel.

[5] In 1967, the Shipps formed a joint venture with Mutual Life of Canada to produce four high-rise apartment buildings, the latter one winning the Canadian housing design award in 1974.

The Shipp Centre, a commercial office complex at the intersection of Islington Avenue and Bloor St., West in Etobicoke, was completed in 1981.

Adjacent to the Shipp Centre is Kingsway on-the-Park, a 289 suite condominium residence in two towers of 24 and 25 stories, respectively.

The buildings are connected to phase three of the Shipp Centre (now called Bloor Islington Place), which allows access to the Toronto subway system.

The arrival of the Duke and Duchess of York was a grand affair with members of Council and dignitaries assembled in the courtyard to greet them.