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Chaplin Estates

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About Chaplin Estates


This affluent neighbourhood is synonymous with Toronto luxury real estate, particularly in the form of exquisitely crafted homes on expansive wooded lots, which often sell over the asking price.

  • Location: Bordered by Eglinton Avenue to the north, Yonge Street to the east, Chaplin Crescent to the south, and the Kay Gardner Beltline Trail to the west, the neighbourhood is situated in Ward 22 and sits squarely in Midtown Toronto.

    Residents come to the Yonge and Eglinton area to unwind, whether it’s to savour a glass of good wine or a sumptuously prepared meal. This famous commercial strip is also known for exclusive shopping, with many stores carrying bespoke wardrobe staples and other unique finds.

    Despite its central location, Chaplin Estates feels far removed from the frenetic energy of the city, offering commuters a quiet and safe place to come home to.

  • Transportation: Residents can walk to the bus stops on Yonge Street, Oriole Parkway, Eglinton Avenue, and Chaplin Crescent. Also, within walking distance are the Eglinton and Davisville and subway stations.
  • Who lives here: A top choice among discerning home buyers, Chaplin Estates calls you to the good life.

Luxury Homes in Chaplin Estates

The neighbourhood is known for its stately mansions on deep manicured lots, and with wide private driveways. Georgian, Tudor, and English Cottage are the most prevalent architectural styles.

With over 900 home sites, Chaplin Estates harbours some of the finest luxury homes for sale in Toronto. Many feature gleaming hardwood floors, finished basements with separate entrances, and oversized detached garages.

The majority of homes in the enclave were built sometime in the 1920s and 1930s, and have been updated to include modern upgrades like chef-inspired appliances.

However, you’ll also find an excellent selection of contemporary style new construction homes that Toronto real estate is known for.

The Chaplins initially prohibited the construction of semi-detached homes to preserve the neighbourhood’s unique character, while municipal officials restricted the use of stucco finishes on home exteriors to encourage visual cohesiveness.

Today, however, there are up and coming townhouse developments in the neighbourhood to add to the housing stock. A good example is The Chaplin, an exclusive project that consists of just five townhouses.

Living in Chaplin Estates

Named after a family of wealthy and forward-thinking landowners who subdivided the property sometime in 1910, Chaplin Estates is among the most prestigious neighbourhoods in Toronto.

Known for gorgeous detached homes on sprawling acre lots, this affluent enclave is within walking distance of world-class dining and shopping at Eglinton Way and Yonge Street.

But what really makes it stand out is the strong sense of community – school fairs, street parties, and countless other events bring people together throughout the year.

Notable in the neighbourhood

Some of the top attractions in Chaplin Estates are:

  • North Toronto Memorial Community Centre: Residents live active lifestyles, thanks to recreational facilities like this one. This multipurpose complex has a gymnasium, weight room, fitness centre, function rooms, and indoor and outdoor pools.
  • Eglinton Park: Located north of the community centre, this multipurpose park is home to the North Toronto Memorial Arena and community-based baseball and soccer organizations.
  • Kay Gardner Beltline Trail – Accessible via Oriole Park at the southern tip of the neighbourhood, the Kay Gardner Beltline Trail spans nine kilometres and is a popular jogging and biking spot.
  • Toronto Public Library Northern District Branch – Spend a quiet afternoon reading your favourite authors at the library, and enjoy their programs on a variety of topics, from child-rearing to cosplay.

Make Toronto your home: Explore luxury properties in Toronto

Find luxury homes for sale in Toronto. For more information on Chaplin Estates, call Toronto real estate agent Casey Ragan at 416.486.5588 or send an email to casey(at)remaxhallmark(dotted)com.