Leaside Neighbourhood History

Today, Leaside real estate is some of the finest real estate in Toronto. Leaside has a long history that dates as far back as 1819 before becoming one of Toronto’s most desirable neighbourhoods among young families and young professionals.

Leaside was first settled in 1819 by a pioneer farmer from Philadelphia named John Lea. In the 1850s, an eight-sided octagonal shaped home was built by Lea’s oldest son William. The home was named ‘Leaside’, and ever since, the neighbourhood has been referred to as Leaside.

The Town of Leaside was incorporated in 1913 by The Canadian Northern Railway on land that was formerly owned by the “Lea” family. Interestingly, the town of Leaside was the first town in Ontario to be planned on paper prior to the commencement of any construction.

In 1967, Leaside became part of the Borough of East York and was no longer considered a “town”. East York has since amalgamated with the City of Toronto.

Leaside Neighbourhood Today

Today, Leaside is a very popular community consisting mostly of young and mature professionals. The northern side of Leaside has drastically changed over the years with many of its original homes being torn down and replaced with larger and more lavish homes, mainly along Broadway. The residents of Leaside have a great sense of community, making this a great neighbourhood for families with kids of all ages. Leaside real estate is some of the finest real estate in Toronto.

Leaside Properties & Real Estate

The majority of Leaside homes are situated on large lots which typically include a private driveway and a garage. Most of the homes in Leaside consist of Tudor-style homes which were mostly built in the 1930s and 1940s. Leaside includes a mix of both detached two-story homes, bungalows and semi-detached homes. In addition to the many beautiful detached and semi-detached homes available in this community, Leaside also includes a number of condominiums and townhouses. 

Thinking About Making A Move?

Are you thinking of buying a home or condo in Leaside or you are thinking of selling your Leaside home or condo?

I would love to learn about your specific real estate objectives and to discuss how I can help you achieve them. Take the first step towards achieving your objectives by contacting me today. I look forward to hearing from you and to answering your questions.


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Leaside Local Business Directory

Below are some of the most prominent businesses within Leaside and the surrounding area.



LIT Espresso Bar
1517 Bayview Ave, East York

The Bagel House

1548 Bayview Ave, Toronto



1568 Bayview Ave, Toronto



1524 Bayview Ave, Toronto


COBS Bread Bakery

1539 Bayview Ave, East York



1614 Bayview Ave, Toronto


West Coast Kids

1646 Bayview Ave, Toronto


Duff’s Famous Wings

1604 Bayview Ave, Toronto


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Get in Touch

+1 (416) 294-3776 braden@chestnutpark.com