The sightlines and majestic beauty of the Avenue Road Hill have over the years, inspired many of Toronto's wealthiest citizens to build their homes in the Casa Loma area.

The one home that stands out above all the others is Casa Loma, a real life medieval castle. Casa Loma was built in 1911, by Sir William Henry Mill Pellatt, a prominent financier, industrialist, and military man. It took three hundred men nearly three years to build Casa Loma at a cost of $3,500,000, which at that time was an unprecedented amount of money to pay for a home. Sir Henry enjoyed his dream home for less than ten years before mounting debts forced him to turn Casa Loma over to the City of Toronto.

In the 1920's, shortly after Sir Henry's departure from Casa Loma, the extensive grounds and greenhouses to the north of the castle were subdivided, and the development of the neighbourhood that we see today began.