Willowdale was originally a postal village, as well as Lansing and Newtonbrook for the district of North York. Willowdale covered the area from Finch Avenue north to Elmwood Avenue to the south and Bathurst Street west to Bayview Avenue east. Lansing covered Elmwood Avenue north to approximately Hwy. 401 south and Bathurst Street west to Bayview Avenue east. The north-south centreline of Lansing & Willowdale was Yonge St. The postal Village of Lansing remained in existence until the Post Office at Lansing corner was closed. When a new Post office was built in Willowdale, the whole area of the former postal villages of Lansing & Willowdale then became Willowdale, but still only a postal village, all within the Township of North York at that time. Newtonbrook was located on Yonge Street, north from Finch Avenue to Steeles Avenue where a number of small business and commercial buildings still remain. The borders of the neighbourhood extend as far east as Victoria Park Avenue, west to Bathurst Street, south to the 401 highway, and north to Steeles Avenue. The neighbourhood bounds Bayview Village to the east and is considered to overlap Newtonbrook to the north. North York Centre is centred at the intersection of Yonge Street and Empress Avenue and is commonly thought to be a part of Willowdale, though its high-rise residential and commercial development in recent years sets it apart from much of the rest of Willowdale.
The Willowdale neighbourhood consists of single family homes, condominium townhouses and high-rise condominium towers. High mass development is restricted along Yonge Street. The single family homes range in age from the original 1910 to 1950s construction. After the 1990s, very large replacement two-storey luxury homes were constructed by tearing down the original houses. It is in this neighbourhood that the term "monster homes" was first applied by Torontonians.
Willowdale was originally established by Jacob Cummer, who immigrated from the United States in 1797. Cummer was a mill owner on the nearby Don River, an owner of a tinsmith shop on Yonge Street and a self-trained doctor and veterinarian. Cummer was held in such high esteem by his neighbours that this area was originally known as Kummer's Settlement.
David Gibson, a well-known land surveyor, was another leader in this community. He helped establish the “Willow Dale” post office, named after the willow trees that decorated this district. The subdivision development took place in 1920s. The Gibson House, which is still standing, is now a historic museum.
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