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Chaplin Estates

The mid-town neighbourhood of Chaplin Estates with its tree lined streets is a quiet upscale family-friendly community.

Chaplin Estates is an upscale neighbourhood located in midtown Toronto, encompassing the southwest section of Yonge and Eglinton. The neighbourhood is a sought-after location for many of the city’s elite, with its variety of first-class amenities, top-notch public services, beautiful environment, and majestic homes.

Chaplin Estates has a very inviting atmosphere – a leisurely stroll will take you past well-maintained lawns along quiet tree-lined streets, giving you a glimpse of the relaxing, laidback lifestyle it offers. The neighbourhood is also located close to plenty of recreational venues, gourmet food shops, and the commercial areas along Avenue, Eglinton, and Yonge, offering plenty of convenience for residents.


The neighbourhood of Chaplin Estates started as a new development on the outskirts of Toronto. It was established in 1913 by William John Chaplin and his son, James Chaplin. Part of their strategy was to market the neighbourhood as a high-end residential community, which is why zoning bylaws and building restrictions were imposed on the sale of every property in the neighbourhood. Some of the restrictions included the requirement of using stucco for more than half of every home and the prohibition of constructing semi-detached houses.

Chaplin Estates, Toronto real estate options and property types

While most homes in Chaplin Estates were built in the 1920s and 30s, the neighbourhood is now equipped with ultra-modern amenities, giving it a lovely balance. Many homes feature elegant Tudor and Georgian-style architecture, and are located on spacious lots with private driveways.

Buyers looking for an ideal home in Chaplin Estates will be able to choose from a great selection of two to three-storey single-family homes equipped with many luxurious features. Most properties have undergone extensive interior renovations while still retaining their elegant old-fashioned exteriors, which gives them a unique character.

Living in Chaplin Estates

    • Residents of Chaplin Estates often head to the commercial districts near Yonge and Eglinton for shopping and dining. Many incredible restaurants are located in this area, such as Jaipur Grille, Quince Bistro, Il Sogno, and many more.

    • The Beltline Trail, which can be accessed from Oriole Park at the neighbourhood’s south end, is a very popular outdoor venue perfect for walking, jogging, and biking. Other parks you can visit include Sherwood Park, Moore Park Ravine, Sunnybrook Park, and Lawrence Park.

    • Most homes in Chaplin Estates are within walking distance from the bus stops along Eglinton Avenue, Yonge Street, Chaplin Crescent, and Oriole Parkway. The subway stations in Davisville and Eglinton are also located close to the neighbourhood. Chaplin Estates is around 15 minutes away from downtown Toronto via Avenue Road or Yonge Street.

    • Some of the schools located near Chaplin Estates are: Bishop Strachan School, Oriole Park Jr., St. Clements School, Upper Canada College, and North Toronto Collegiate Institute.

Need more information on luxury homes for sale in Chaplin Estates? We can help you find the perfect home in this wonderful neighbourhood! Get in touch with Cheryl Thompson of Sotheby’s International Realty Canada at 416.960.9995. You can also send an email to cthompson(at)sothebysrealty(dotted)ca

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