While most house hunters are familiar with Toronto’s elite neighbourhoods like Rosedale, Forest Hill, and The Bridle Path, it is the delightfully hidden enclaves that often offer a more heightened feeling of exclusivity. Follow our luxury real estate experts to Toronto’s most exclusive neighbourhoods where private road designations are so prestigious they prevent access to Google Street View!
Baby Point
Where you’ll find it: Roughly between the Humber River and Jane Street above Old Mill Road.
As you drive through the stone gates on Jane Street leading to Baby Point, you can’t shake the feeling you’re entering a gated community. Pronounced “Bobby” by in-the-know locals, some of Toronto’s finest examples of early 1900s architecture stand along the broad boulevards and serene crescents here. A mix of original estate homes with a fairy tale quality that defines the word “enchanting” are made all the more grand by some of the largest properties in Toronto’s west end. On streets that wind along the picturesque hilly landscape of a former orchard, elusive listings quickly disappear even when the market is suffering.
Named after prominent French fur trader James Baby, who created his own little paradise on the land in the early 1800s, Baby’s heirs later sold the land to developers in 1912. The lush green orchard was the idyllic setting for spacious homes surrounded by parkland set atop a ravine where the best of the best properties overlook the flowing Humber River.
Annette and Jane Street’s elite shopping areas are within walking distance, providing an eclectic mix of small grocers, shops, and restaurants, while nearby Bloor West Village offers a more upscale selection of shopping and dining options. The private Baby Point Club is a recreational hub for locals, and runners, dog walkers, and leisurely strollers follow the trails at Etienne Brule Park along the Humber River. The Bloor-Danforth subway line is also within walking distance, and drivers have convenient access to Lake Shore Boulevard and the Gardiner Expressway.
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Governor’s Bridge
Where you’ll find it: Nestled just east of Bennington Heights and west of Bayview above The Evergreen Brickworks.
Governor’s Bridge is sought after for its convenient location perched on the Moore Park Ravine. From its bougie name to the stone bridge that feels a little like crossing a moat to reach a protected fortress, this micro-neighbourhood sitting high above the Don River is possibly Leaside/East York’s best-kept secret. A small selection of just over 100 homes built between the 1920s and ’40s offers an opportunity to move into a smaller redone home in a wide range of architectural styles, purchase a diamond in the rough, or discover one of the recently built homes that are popping up on the former sites of the original tiny bungalows that once stood on the area’s expansive lots. Unexpected finds include the upscale condo townhouses of Governor’s Manor in a beautifully restored Tudor-style apartment building.
The Spanish-Esque designs of the area’s first homes earned the neighbourhood the nickname Little Hollywood. Today the enclave is so exclusive it sees very little listing activity, so you have to act fast if you want to snatch up one of these beauties.
Nesbitt Park is a family-friendly spot in the heart of the area, while nearby amenities include the upscale and chic Moore Park and Bayview area, Leaside, or Summerhill. You can also bike or drive down to the eco-friendly, très trendy Evergreen Brickworks. Easy access to the Bayview Extension and DVP gets you in or out of town in minutes, while a quick bus ride goes to the Rosedale Subway station.
If you’re looking for a private, exclusive neighbourhood, you might also want the same type of experience for your children. Read: How to Find the Best Private Schools in Toronto to learn more.
Cricket Club
Where you’ll find it: Sandwiched between Hogg’s Hollow and Nortown, bordered by Wilson Avenue to the North and Bedford Park to the south.
Named after the circa 1925 Toronto Cricket Skating and Curling Club, this exclusive community sits pretty in the far reaches of the city’s elite uptown. Just on the other side of Yonge, where York Mills turns into Wilson Avenue, this garden-forward enclave features lush green lawns and a shade-providing canopy of mature trees on streets unencumbered by tiresome sidewalks.
Georgian-style homes feature prominent central entries opening up onto spacious light-filled rooms where original characteristics include airy bay windows, intricate built-ins, hardwoods and trim, French doors, and cozy fireplaces.
The chic “high streets” of Yonge and Avenue road are designer shopping destinations, from clothing to home decor and rich gourmet delights topped off with a glass of wine and fine dining to recover. Along with the cricket club, residents enjoy programs from tots to retirees at the Armour Heights Community Centre or leisurely summer days on the links at the artfully landscaped Don Valley Golf Course. TTC routes take you to York Mills or Lawrence subway stations, while the nearby 401 is minutes from the DVP, ideal for getting to work or a night on the town.
Sometimes and exclusive neighbourhood isn’t actually a neighbourhood but rather a building! Take for example some of the Trendiest Lofts in Toronto. Read our blog to get the scoop on loft living in the GTA.
Wychwood Park
Where you’ll find it: North of Davenport, east of Christie and west of Bathurst just below where Tyrrel Avenue ends.
At the southwest corner of this gorgeous neighbourhood sits Tollkeepers Park, where you’ll find the oldest surviving tollkeepers’ cottage in Canada. A stone and wood gate structure and a sign announcing the private road with no exit establish Wychwood Park’s exclusivity. As one of Toronto’s oldest neighbourhoods, the significant historic architecture earned the area an Ontario Heritage Conservation district designation in 1985.
While a few homes from the 1880s still stand, most houses were built between 1906 and 1935. Eden Smith-designed Arts and Crafts houses mark the distinct English feel of the area. Enhancing the English countryside aesthetic are the surrounding wooded parkland and Taddle Creek Pond, famed for its turtle inhabitants and celebrity swans Oscar and Felix. Although residents pay a special tax for an executive council to manage the private roads and parkland, the very nature of the tax has few complaints from those lucky enough to call the neighbourhood home.
Residents also overlook the fact they might have to travel a bit further from home for luxury items and services. They always have the everyday amenities along St. Clair West to fall back on and reliable streetcars heading to the Yonge or Spadina subway lines to cater to their daily needs.
If you’re looking for a home in one of these exclusive enclaves or if you’re looking for something totally different, get in touch with the top Toronto real estate agents at The Christine Cowern Team. Reach out today by giving us a call or sending us an email directly.
