Toronto's coolest neighbourhoods
This is far from an extensive list of Toronto’s coolest neighbourhoods, nor is it in any particular order. As a die hard Torontonian , I spent my mid teens to mid 40’s living, playing and working in all of these areas and have seen them all transform from little communities into the thriving neighbourhoods they are today. If you’e considering a move to Toronto or you’re new to the city , these are some of my favourite places based on walkability, diversity, culture, green space, good housing stock, decent schools, Yummy nosh, and proximity to the core & the lakeshore.
Trinity Bellwoods The focal point of this city neighbourhood is the very picturesque Trinity Bellwoods Park, which spans the entire length of the neighbourhood from Queen West to Dundas West. No longer a neglected city park but the vibrant heart of a lively community. Today the neighbourhood is one of the trendiest areas of the city with housing stock that has risen 10 fold in the last decade. Popular with young professionals , there are a variety of property styles to choose from including rental properties, condominiums and freeholds. Also, there is no shortage of bars and cafes to dine or sip coffee at.
Kensington Market – Very little has changed in Kensington Market since it was established in 1920's by Jewish immigrants and this is part of its charm. Nestled between China Town and Little Italy this unique bohemian neighbourhood has a walkable outdoor market with a diversity of goods and people that reflects Toronto culture. Attracting artists, tourists and people from a variety of backgrounds including students at nearby U of T and OCAD that are drawn to its indie shops, vintage boutiques, arts spaces , bars, cafes and international restaurants. Students and families populate Victorian houses along tree-lined streets.
Little Italy -The neighbourhood may be known as Little Italy, however it is no longer exclusively Italian. It’s actually one of the most multicultural neighbourhoods in Toronto. Home to a large Italian community, there is also a substantial Portuguese and Asian population because of its close proximity to Little Portugal and China Town . There’s an array of quality schools in the vicinity, great restaurants, bars and in walking distance to everything else. This makes the neighbourhood suitable for families, couples and singles with housing stock ranging from semi's, detached homes , select condominiums and town-houses.
Little Portugal - Located in the West end of downtown Toronto, this area is flush with amenities. Little Portugal is a neighbourhood in transition. It has witnessed rapid gentrification in recent years, which underscores it’s dynamic personality and property opportunity. Like many other neighbourhoods near downtown, Little Portugal is undergoing gentrification with some hip independent businesses and an enclave of restaurants along Dundas between Ossington and Lansdowne. Residents are a mix of seniors and families of Portuguese and Brazilian descent, as well as new urban professionals.
High Park- Once a pleasantly sleepy community of European immigrants, the High Park area has evolved over the past couple decades into an enclave for educated, affluent Gen X and millennials to raise their families in befittingly organic style. For visitors that means Roncesvalles Village’s trove of foodie-approved casual restaurants, health food stores and gourmet shops. “Roncey” is also known for its indie gift shops, fashion boutiques and yoga studios. Further north, the Junction is another hit with smart, young Torontonians, but with an edgier, artier vibe, and replete with small galleries, vintage shops and coffee bars. The heart of the neighbourhood is the sprawling, leafy High Park, home to a small zoo, an extensive trail network, adventure playgrounds, a leash-free dog park and scenic pond.
The Junction- It's called the Junction because it's, well, a junction, originally of two First Nations trails and then of the Canadian Pacific Railway's Ontario and Quebec lines with the Toronto, Grey and Bruce and Credit Valley lines. A neighbourhood that has finally arrived, The Junction is home to some of the city's most interesting furniture shops, espresso bars, restaurants and live music venues. Blessed with some of the city’s best high schools, it’s popular with families and couples. Although there are several new condominiums peppered around the area you will find mostly semi’s, row and detached homes lining its leafy streets.
The Junction Triangle – The Junction Triangle (not to be confused with The Junction) is a small neighbourhood East of the Go Train, West to Dufferin St, North to Davenport and South to Bloordale Village. Ubisoft and Freshbooks both have large offices here and up and coming Sterling Road is home to Toronto's Museum of Contemporary Art (MOCA). The Junction Triangle is already a great place to live—and its best years are still ahead of it. Some pluses: Go/Up train station runs express service every 20 minutes to the Airport and downtown to Union Station, upcoming transformation of Sterling Road , with French immersion schools and some of the city’s best galleries already making the move here along St. Helens Ave and around Dupont Street. Like The Junction, The Junction Triangle has a mixture of single family homes, town-homes and condominiums and is popular with singles, couples and families alike.
Liberty Village - Once a gritty industrial area, Liberty Village has become a sought after address for Toronto young urban professionals. While historic factory buildings still dot the area, many have been converted for contemporary uses, from cool lofts to even cooler restaurants and bars. Centred on the Liberty Market Building, this neighbourhood is where Toronto’s young urban professionals choose to live, work and play.
Parkdale - A century ago Parkdale was once Toronto's wealthiest district. With tree lined streets, it is now one of the downtown cores most diverse neighbourhoods. Residents range from Tibetan, North African and West Indian mixed with new urbanites. The area is popular for trendy bars, restaurants, vintage fashion, furniture and fabric stores. There are still a few affordable -ish victorians to be had.
Roncesvalles - Culturally, the area was known as the centre of the Polish community in Toronto but with gentrification this lively neighbourhood is popular with families and young professionals drawn to its leafy streets, well proportioned Edwardian and Victorian homes, the sprawling green space of High Park, and Lake Shore Boulevard all within close proximity to downtown. Not to mention several excellent schools to choose from, boutique shops, cafes and restaurants, plenty of fresh grocers, and good public transit. Along its tree lined streets many Roncesvalles multi- unit homes have been converted back to single family homes.
Rosedale - Well established over a 100 years ago, Rosedale has held its position as Toronto’s chicest and wealthiest central neighbourhood. Surrounded by beautiful ravines and parkland whilst in the middle of the city. With fantastic shops on Yonge street including the High End fashion shops of Yorkville, it is a perfect spot for the well heeled. Properties range from stately homes, to modernized row victorians to newly built condominiums.
Annex - Is a vibrant neighbourhood that draws its energy from the University of Toronto, as well as from the bars, restaurants and museums that crowd together along Bloor Street. The neighbourhood attracts people from all walks of life including, prominent artists, business people, as well as students and faculty. An excellent place to live work and invest. Many of the the Annex’s large edwardians houses have been converted back to coveted single family houses reflecting on the return to prominence of this historic Toronto neighbourhood. There are also several with multi-unit low rise older and newer buildings.
Wychwood Park - Was a former gated Community That sits on the hill north of Davenport , West of Bathurst Street. Now the area has expanded West to Oakwood South of St. Clair and the whole area is now known as Wychwood. A quiet family neighbourhood with a mix of low and mid-rise residential dwellings,
it is bounded roughly by Oakwood Avenue and Dovercourt Road to the west, Bathurst Street to the east, St. Clair Avenue west to the north and the CN rail tracks to the south.
The area features a number of small but well-loved green spaces, including Hillcrest Park, Wychwood Barns Park, Garrison Creek Park, the Tollkeeper’s Park and others.
Wychwood Barns hosts a farmer’s market and art shows, among other attractions. A sought after neighbourhood for families.
Seaton Village- Seaton Village is a centrally located family oriented neighbourhood. Remarkably, this neighbourhood has managed to maintain the feel of a small town village, even though it is situated in a busy part of the city. With Annex to the East and Little Korea to the South it’s popular with both families and singles alike. Housing stock is mostly row and semi detached homes on its leafy streets. Perfect for rental investments because of its proximity to U of T and downtown .
Leslieville - This east-end neighbourhood forms part of the broader neighbourhood of South Riverdale to Lakeshore Blvd East. Leslieville began as a small village in the 1850s, which grew up around the Toronto Nurseries owned by George Leslie (1804-1893) and sons, after whom the community is named. Today Leslieville is a sought after neighbourhood popular with young families, singles, couples and professionals. There is a great selection of specialty shops, restaurants, cafes and antique shops that line Queen St East from the DVP right to the Beaches (another great neighbourhood especially during the summer). Homes range from row house, condominiums, detached and semi's.