Lexington Avenue, Westmount
Average Housing Price: $2.12 million
Located in the wealthy Montreal enclave of Westmount, Lexington Avenue is a predominantly Anglophone neighbourhood notable for its large, tasteful houses.
The area is overlooked by Saint Joseph's Oratory, A Roman Catholic basilica which is also Canada's largest church, just across the border in Montreal. It was dedicated as a National Historic Site of Canada in 2004, 100 years after construction began.
Bridle Path, Toronto
Average Housing Price: $2.24 million
Tucked away in a quiet area north of Lawrence Avenue East overlooking a small valley, the Bridle Path neighbourhood of Toronto can be accurately summed up with just one word: Mansions.
Surrounding the Bridle Path one can find Toronto's famous ravine trails, highly-regarded schools both public and private, and a campus of York University down in the valley. If nature is something you deeply appreciate, then you can also visit Edward Gardens, a botanical garden located within the Bridle Path.
The Bridle Path is known for housing celebrities and many of Canada's richest people, among whom include Elton John, Conrad Black, Drake, Gordon Lightfoot, Mick Jagger, and Prince. Mansions along the Bridle Path have also been used as movie sets, with the most notable example being Regina George's house in Mean Girls.
Don't be fooled by the price tag though. While a couple million could purchase you one of the smaller houses on the outskirts of the area, the big mansions which define the Bridle Path can sell for well over $30 million.
Average Housing Price: $2.29 million
Located just south of the Bridle Path, Sunnybrook is best known across Canada for its famous hospital baring the same name. The area is small, tucked cozily between the hospital and the historic Leaside neighbourhood. It's also bordered by the Don Valley River, which boasts beautiful and quiet paths for those seeking to get out of the house.
The area is known for its old money, with average net worth vastly dwarfing average incomes. That feel will undoubtedly sink in for those who visit. The houses are big, but not as grandiose and opulent as the nearby Bridle Path. The area is also home to the Sunnybrook Stables for avid equestrians. Joseph Kilgour, an avid horse rider, once owned much of the land in Sunnybrook, but upon his death donated his land to the city to establish the stables for all residents to enjoy.\
The Sunnybrook Hospital, affiliated with the University of Toronto, is among the world's leaders in medical research. As recently as 2015, doctors at the hospital made a medical breakthrough when they non-invasively opened the blood-brain barrier for the first time.
Summit Park, Westmount
Average Housing Price: $2.76 million
Across the Fraser River from Richmond and the airport, Kerrisdale is a large, quiet, and diverse neighbourhood encompassing much of southern Vancouver. Beautiful, classically Vancouver-ish houses make up most of the area, notable by their back alleys and well-kept front lawns, often guarded off by hedges.
The rest of the neighbourhood is mostly schools and small greenspaces, but as one reaches the perimeters of the community, it becomes clear that there is more to offer. On the west side lies Pacific Spirit Regional Park, which contains days worth of walking trails. On the other side of the park is the Vancouver campus of the University of British Columbia, itself a peaceful and appreciable place to tour.
At the southern end of Kerrisdale, often called "the Southlands," one can find a First Nation's reserve, stables, two golf courses, a driving range, and more.
Sunnyside &amp; Edgehill, Westmount
Average Housing Price: $2.84 million
Just south of Lexington Avenue, Sunnyside & Edgehill contains similarly large houses along a steep hill.
At the top of the hill towards Sunnyside Street, one can overlook the city of Montreal from the Summit Circle Lookout. Directly north lies Summit Woods, a large forested park popular among pedestrians and dog owners.
At the south end lies St. George's School of Montreal, a prestigious private school boasting various notable alumni including Kevin O'Leary.
Lawrence Park North, Toronto
Average Housing Price: $2.81 million
Lawrence Park North is a neighbourhood with a history of great wealth, having housed many members of Canada's aristocratic elite since the early 20th century.
On the west side of the neighbourhood is Avenue Road, a quaint street lined with a multicultural array of restaurants and quality fashion boutiques. On the east side lies the Don Valley River running straight through the Rosedale Golf Club.
Yonge Street, the longest street in the world, runs directly through not only the middle of the neighborhood, but the middle of Toronto itself. This is where Avenue East meets Avenue West, and the street more than lives up to its status. The street is known for being host to a wide variety of cultural events, protests, and parades. If you're not a fan of loud noises, don't worry, because you would have to drive southwards to find it. You will, however, get to enjoy the bustling culture Toronto's main street has to offer.
Average Housing Price: $2.89 million
The most expensive area in western Canada, Shaughnessy is a planned neighbourhood centrally located within the city Vancouver. The houses here are big and are built with class, avoiding much of the McMansion horror which defines other planned developments.
A number of famous people, especially actors and actresses, were raised in the area, and it is the location where Seth Rogen and Evan Goldberg wrote the script to Superbad. Given Vancouver's notable film production scene, you may even see a film being produced here too.
The neighbourhood is also known for its green space, most notably the VanDusen Botanical Garden.
Forest Hill, Toronto
Average Housing Price: $3.18 million
Forest Hill is a perfect location for rich Torontonians if they want an area that is quiet, but with easy and quick access to all the benefits of the scene of downtown Toronto.
The northern half of Forest Hill surrounds an area of Bathurst Street, the heart of Toronto's Jewish community, with a variety of Jewish day schools and synagogues lying just north of the neighbourhood.
The southern part of Forest Hill is nested between Yonge Street, Eglinton Avenue, Bathurst Street, and St. Clair Avenue. Bloor Street, home of many of Toronto's most popular bars and clubs, is only a couple of kilometers south, white the area's border is home to a variety of independent bars and restaurants.
The area is home to St. Michael's College School, known by the locals as St. Mikes, Bishop Strachan, and Upper Canada College, three of Canada's most prestigious private schools. The tip of the Cedarvale Ravine also pokes into the neighbourhood, providing both local pedestrians and cyclists access to a scenic nature walk.
York Mills, Toronto
Average Housing Price: $3.4 million
Named after a local sawmill in a part of the neighbourhood now known as Hoggs Hollow, York Mills is the most expensive place to live in Toronto and among the country's wealthiest neighbourhoods.
Today, York Mills is the northernmost portion of Toronto's Millionaire's Mile. The area is known for its luxury homes, but is also the location of several luxury condos which distinguish it from other rich parts of uptown Toronto.
An historical site in the area is Miller Tavern, which served as a bar and hotel for decades before closing in the 1960s (it even functioned as a gambling den during prohibition). Today, visitors can appreciate the old building's Georgian Survival architecture