<img height="1" width="1" style="display:none" src="https://www.facebook.com/tr?id=294326554740919&ev=PageView&noscript=1" /> Chaplin Estates - Wilson Sisters

Chaplin Estates lives up to its name as one of Toronto’s most prestigious neighbourhoods. Nestled above the Kay Gardner Beltline Park, Chaplin Estates is located in the southwest part of the Yonge and Eglinton area (south of Eglinton Avenue, east of Avenue Road, west of Yonge Street, and north of Chaplin Crescent). This much desired postal code features some of the city’s best coffee, award-winning restaurants, luxurious shopping, picturesque parks, top-notch public and private schools, user-friendly transit service, and overall easy city-wide access.

Once upon a time . . .

The year is 1913. An Eglinton area landowner since 1860, William John Chaplin, along with his son James D., breaks out as an early Toronto developer and registers a plan of subdivision. Chaplin Estates lives up to its name as a high-end residential district through the establishment of building constraints and zoning bylaws that restrict such “abominations” as overdone tacky stucco exteriors and semi-detached construction. Launched as the Chaplin Realty Company, William and Jimmy’s venture culminates in the sale of these exclusive lots from 1921 to 1925 with prices ranging from $500.00 to $9000.00 per lot.

Bricks & Mortar

Those very same lots, thanks to the clear-cut vision of the Chaplin family, now feature 2- and 3-storey homes – notably, detached with limited stucco detailing – and together make up present-day Chaplin Estates. This beautiful, pedestrian friendly, tree-lined neighbourhood boasts 1920s–1930s Tudor, Georgian, and English Cottage-style homes on premium lots with private driveways and range from $600,000.00 to well over $2,000,000.00. Both well-loved, and newly renovated homes await you and your family – a heritage neighbourhood that has remained true to the vision of Billy & Jimmy Chaplin.

A breath of fresh air

Chaplin Estates is nestled between two fantastic parks, with Eglinton Park to the north and Oriole Park rounding out the neighbourhood’s southern end. Weighing in at 5.17 acres, Oriole Park is small but mighty and boasts tennis courts, picnics tables, a baseball diamond, and one of the few playgrounds in the city designed for the use of disabled children. This well utilised park gives access to the Kay Gardner Beltline, a 4.5km trail running between Allen and Mount Pleasant Roads. Originally the Belt Line Railway, the 1892 venture was created to connect the neighbourhoods of Rosedale, Moore Park, Forest Hill, and Swans, but closed 28-months later – a victim of recession to be left desolate until it was purchased in 1973 by the city and designated as parkland. Situated at the northern end of this picturesque neighbourhood, Eglinton Park also features tennis courts and a baseball diamond, as well as an artificial ice hockey rink, a wading pool, and a community centre. The North Toronto Community Centre is well loved by residents who enjoy the gymnasium, track, exercise room, and year-round indoor and outdoor swimming. Two pools, one park: who could ask for anything more?


Getting around the city from Chaplin Estates is easy whether you drive, walk, ride, or utilise Toronto’s convenient transit service. By taxi or car, a 15-minute drive will get you downtown (head south on Yonge Street or Avenue Road), while a similar timeframe will get you to the Allen Expressway or Don Valley Parkway depending on where you want to go. Bus stops are readily available and can be found on Eglinton Avenue, Yonge Street, Chaplin Crescent, and Oriole Parkway, or it is a short walk to the Eglinton Avenue or Yonge Street shopping districts and subway stations. Jump aboard at either Eglinton or Davisville Station. The city of Toronto awaits you!

Coffee . . . Where art thou?

Committed coffee connoisseurs and café owners of Rachel’s Coffee House, Jack and Maria, while new to the Chaplin Estates neighbourhood, have an extensive track record running a popular franchise café previously. Committed to quality coffee (locally sourced organic/fair trade beans) and fresh treats (preservative free, all natural, and baked daily in house), Rachel’s Coffee House is an extension of your home with its relaxed atmosphere and cozy front patio. The Italian frozen yogurt and Mascarpone/salted caramel paired also come highly recommended. Another trusted Toronto favourite, Bulldog Café’s second location is perfectly positioned adjacent to Chaplin Estates. This well-loved establishment really does serve great coffee, and where the Granby Street location had taken flack for its supposed elitist attitude, locals are singing the praises of the 7-bean blend made by award-winning friendly baristas whose artistic talents are experienced in both the latte art and the perfectly pulled espresso in this newer location. Homemade tasty treats both savoury and sweet are perfect companions to quality coffee that really can’t be beat however you rate the service.

Date Night!

Chaplin Estates is part of the broader Yonge and Eglinton neighbourhood fondly referred to as “Yonge and Eligible” after the young professionals who have made the area home – a reputation perfect for a neighbourhood overflowing with outstanding restaurants, cafés, pubs, and lounges. In the summer months, there are so many outdoor patios to choose from as well as a range of international cuisine available in both casual and 5-star fine dining establishments. For exceptional Italian fare, Zucca features authentic, flavourful dishes that will have you singing for your supper (in Italian) with friendly service that can’t be beat. For a casual date night, why not opt for the traditional dinner and a movie? Bamburger is licensed and features gourmet burgers, award-winning poutine, and sweets second to none, all at friendly prices, and you are only a short walk away from Silver City Yonge-Eglinton Cinemas where there are nine screens and an array of blockbusters awaiting you. Be sure to pop into the Blue Meaney for a nightcap after – the ideal way to unwind after a long day or week.

Does that come in a size 7?

Whatever your size, the Eglinton Way and Yonge Street shopping districts will dress you up right with high-end boutiques and trendy fashion retailors ready and waiting. If you and your ‘girls’ need a pick me, Secrets from your Sister is where you want to be. They will size you up right and position your assets for success. For those last-minute invites to a gala, your fairy godmother is just around the corner at the chic and friendly Poor Little Rich Girl (2094 Yonge Street). They will have you spinning in designer tulle, taffeta, or silk – dressed to the nines to rescue your prince charming. Can’t find your silver slippers? Why not opt for red ones instead? Eglinton Way’s Madison Shoes & Accessories will help you dance the night away in comfort and in style. Does Prince Charming need an overhaul? Are the little prince and princesses lacking the latest for school? Whether you need to renovate the castle kitchen or refill the fridge, some of the best shopping in the city is available with a range of unique stores, gourmet grocers, and specialty shops only a short walk away. Block after block of restaurants, cafés, shops, and services will meet your day-to-day needs whether you are looking for fresh cut flowers, cat food, dental work, a pedicure; or a loaf of bread, a carton of milk, and a stick of butter.

Where to take the kids. . .

Your kids will love the North Toronto Memorial Community Centre. With arts and crafts, ballet, jazz, and a range of sports including basketball, volleyball, badminton, and Martial Arts, this recreation centre will become your family’s home away from home. You and your children (from toddlers to teenagers) will learn how to skate or swim with programs for all ages. School holidays, while celebrated by children, can be stressful for parents who don’t have the option to take time off. Residents of Chaplin Estates will have nothing to worry about with quality, fun-filled day camps that will give your children memories to last a lifetime.

Also, be sure to visit the Northern District branch of the Toronto Public Library. Located on Orchard View Boulevard, the branch has fantastic programs for all ages. Does your child struggle with reading? Take advantage of the library’s free one hour weekly tutoring, or if your child loves the art of language, calligraphy classes for children 9 to 12 are also available. From elementary school to high school, private, public, or catholic, Chaplin Estates has some great options. Most Toronto schools have definite enrollment boundaries, so it’s always a good idea to contact the school you have in mind to ensure your new home falls within its boundaries. For more information, visit the Toronto District and Toronto Catholic School Boards websites.