The 5 Most Unique Retirement Neighborhoods in Toronto

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Best Places to Retire in Toronto
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Each year I help over 500 clients file their Canadian and US tax returns as well as plan for both their Canadian and US investment accounts. I also regularly help new US clients plan for their move to Canada.

Feel free to reach out via email at phil@philhogan.com or by phone or text here 250-661-9417.




Although Toronto is one of Canada’s most expensive cities to live in, it is also one of the most diverse, most vibrant, and, some would suggest, the most American city that the country has to offer. As Canada’s biggest city, Toronto boasts a population of just over 2.6 million people in the city itself and almost 5 million in the Greater Toronto Areas, known locally as the GTA. By way of comparison, Toronto would land somewhere between Chicago and Houston in size.

Not surprisingly, Toronto ranks highly on the list of potential landing spots for Americans looking to retire north of the border. One possible reason for this appeal is the city’s wide variety of diverse and liveable neighborhoods. With more than 200 official and unofficial neighborhoods, each with a personality of its own, Toronto has earned its nickname of “the city of neighborhoods.”

For Americans looking to retire in this cosmopolitan center, some of these 200 options are most likely of the visit-and-explore-but likely-don’t-want-to live-there variety. But many areas are perfectly suited for American retirees looking to balance small-town charm and relaxed pace with proximity to big city hustle and amenities. Here is a list of some of the more unique and accessible retirement neighborhoods in Toronto:

Humber Valley Village

Retire to Humber Valley Village

A relatively affluent neighborhood located in what used to be known as the City of Etobicoke, Humber Valley Village is defined by its green spaces. Not only is it close to one of the finest golf courses in Canada (the spectacular St. Georges Golf and Country Club), but this neighborhood has more than a dozen parks and an elaborate, well-maintained network of bike and walking trails. It is also home to James Garden, a one-time private estate that is now a city-owned botanical garden where you can enjoy massive lawns, rock and flower gardens, nature trails, and even a lawn bowling court.

The Beaches

The Beaches Toronto Retire

If laid-back and relaxed describes your retirement plans, you will feel perfectly at home in the neighborhood known as The Beaches. Overflowing with small-town charm, it is two areas in one. The first is the beachfront, which runs along Lake Ontario and features sandy beaches, relaxing parks, an abundance of trails, and even a 2-mile long boardwalk. The second unique area of this neighborhood is Queen Street East, perfect for sauntering and shopping. Quaint and quirky are the best ways to define the stories along this pedestrian-friendly stretch. Do be aware that The Beaches also includes Kew Gardens. This large public park plays home to many of Toronto’s festivals, markets, and concerts, including the annual Beaches International Jazz Festival, held every July. So, if the occasional crowd is not your thing, plan a visit but maybe look elsewhere on this list for your retirement home.

The Cricket Club

The Cricket Club

This neighborhood is named, appropriately, after the Toronto Cricket, Skating, and Curling Club that dates back to 1827. (The Club’s name was decided by a coin toss in 1956 to determine which word would come first in its official title: “skating” or “cricket.”) This is an affluent neighborhood with a country-charm vibe and some of the best shopping that the city offers, from designer clothing stores and antique shops to gourmet coffee shops and fine dining restaurants. You will never run out of places to share with family and friends when they come to visit.

Casa Loma

Casa Loma Toronto

Imagine a close-knit neighborhood surrounding a castle. That is Casa Loma, an area named after the fantastic Casa Loma castle, built in 1911 by Sir William Henry Mill Pellatt, a prominent Toronto financier and industrialist. This is a neighborhood of forests and ravines, which feels more like a secret retreat located miles (and centuries) away from any city. Every amenity that you might need is nearby, but public transportation (bus, streetcar, and subway) making a trip downtown relatively easy. And with over 24% of area residents classified as seniors, you will have plenty of opportunities to socialize.

St. Lawrence Market

St. Lawrence Market

If you love history, the bustle of a European-style market founded in 1803, and gorgeous architecture, St. Lawrence Market is the neighborhood for you. These 10 city blocks are, quite literally, the history of Toronto, marking the exact location where the Town of York was established in 1793. But historic does not mean old. This neighborhood has been kept vibrant and modern by a commitment to urban planning that has become a model for the design of mixed-use communities across North America. Food and family define this area, which also includes a good assortment of condominiums and one-level homes perfect for retirement living.

This quick look at 5 of Toronto’s 200 neighborhoods gives you a glimpse into the opportunities and options that Americans have when considering retiring to Canada. There is truly something for everyone in the country to our north, so watch this blog for more tips and recommendations.

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