Where to Buy Next

Change comes slowly to Toronto. Name almost any exciting new infrastructure project and it’s probably years behind schedule, at best. In our frustration, we obsess about current realities and rail against the transit gods, city planners and provincial overlords, but Toronto is on the precipice of enormous transformation. By the end of the year, the Eglinton Crosstown should be flying from Weston to Kennedy, and by 2031, the Ontario Line will be barrelling from Liberty Village up to Don Mills—and that’s just the beginning. Construction is underway for the East Harbour Transit Hub, a massive new interchange just south of Riverside; five high-traffic GO routes are being expanded; and the city is getting honest-to-god, from-scratch new neighbourhoods in the Port Lands and Downsview.

Related: Six experts wrestle with the future of Toronto’s housing crisis

In short: tectonic changes are afoot. And while everyone stands to benefit, certain pockets have much more to gain. Once-overlooked areas will become highly coveted, and property values will rise accordingly. The trick? To spot them early and get in before other buyers catch on. To that end, we undertook months of exhaustive research and identified 12 neighbourhoods where transit accessibility, housing stock and desirability are most likely to skyrocket. Here, our comprehensive guide for property hunters and gawkers alike.

1 Weston Village
2 Regent Park
3 The Port Lands
4 South Parkdale
5 Yonge-Bloor Corridor
6 Riverside/South Riverdale
7 The Golden Mile
8 Bloorcourt/Bloordale
9 Oakwood Village
10 Downsview-Roding-CFB
11 Pape Village
12 Woodbine-Lumsden

Weston Village

Where small-town feel meets first-class transit

1 When the up express started running in 2015, Weston Village, just west of Jane and south of Woodward Avenue, won the transit jackpot. It used to take more than an hour to get from there to Union—and that’s making the dubious assumption that everything was running on time. Now, the trip is less than 20 minutes, and soon the neighbourhood will be connected to the Eglinton LRT via a new stop at Mount Dennis.

It’s no surprise that house hunters have already come looking, and what they’ve found are 19th- and 20th-century storybook homes with gables and decorative masonry, plus 74 acres of continuous green space along the Humber. And there’s more housing on the way: four towers are in the works, which will add more than 2,000 units alongside a 400-seat performance hall and worship space.

Despite all this hustle and bustle, Weston still feels like a small town. It’s packed with family-friendly fixtures like the Artscape Weston Common and the picturesque Weston Public Library.

Book Worm 
No one knows Weston Village better than Suri Weinberg-Linsky, the owner of Squibb’s, Toronto’s oldest bookstore

Describe Squibb’s. “Smush a Hallmark, Staples, Indigo, educational press and art store together.”

Your parents bought the store in 1980. Why? “My dad was from eastern Europe and read to improve his English. My mom worked at the Globe. They both loved books.”

If Weston Village were a novel, what genre would it be? “Tragicomic redemption story. Like A Tale of Two Cities: opposing sides—heritage and growth—mistrust each other before realizing they’re stronger together.”

Best neighbourhood spot? “The serene Humber River. It’s peaceful and filled with animals.”

Regent Park

The city’s most transformative project enters its final stages

2 When city planners started work on this area in the 1940s, it was considered a slum. Their first stab at a revamp was an unappealing cluster of mid-rises with no major thoroughfares and few green spaces. Since then, the urban pocket bounded by Gerrard East, the Don Valley, Queen East and Parliament has become the site of a remarkable course correction.

Related: Mitchell Cohen on Regent Park’s two-decade revitalization

An ambitious revitalization project delivered an aquatic centre, an arts hub and MLSE-funded athletic grounds. Today, there’s a diverse community living in sleek mid- and high-rise buildings with a mix of affordable rentals, subsidized housing and market-rate condos. The neighbourhood has attracted buzzy new businesses, like Janet Zuccarini’s Café Zuzu, while holding on to long-time staples, like the Sultan of Samosas.

While the west side of Regent Park already hums with new energy—including the forthcoming 900-unit, mixed-income building at 325 Gerrard—the eastern edge is still in the middle of its glow-up, though likely not for long. With a public library and civic plaza on the horizon, this last pocket of the neighbourhood may soon shift from “on the rise” to fully rizzed up.

Best of the Fest
The Regent Park Film Festival is scrappy, free to attend and committed to historically marginalized filmmakers and films. Here are a few of its programs

The Regent Park Film Festival The namesake festival starts every November. Some of its films, like last year’s Village Keeper, have gone on to be official selections at TIFF.

Under the Stars Every summer, the festival hosts outdoor screenings in Regent Park. Arrive early for an array of food options.

School Programs The festival offers free film screenings and accompanying lesson plans to schools. Each addresses an issue facing school-aged kids in the city.

Live It to Learn It Black youth can apply for the festival’s paid internship program, where they work on some of Toronto’s biggest TV shows.

The Port Lands

A state-of-the-art neighbourhood right on the waterfront

3 It’s easy to see why Google wanted to turn part of Toronto’s Port Lands into the city of the future. The area comprises more than 2,100 acres of waterfront, and it’s less than 15 minutes from downtown. The long-standing obstacle to developing the area, just beneath Lake Shore Boulevard and west of Leslie Street, was that its location at the mouth of the Don River made it a flood risk. But, in 2017, all three levels of government ponied up a combined $1.25 billion to divert the river. Now it’s game on.

There’s already Biidaasige Park (which includes the Don Greenway wetlands); four futuristic bridges designed for cars, transit, cyclists and pedestrians; and pre-existing hot spots like the Leslie Spit and the Michelin-­recognized Cherry Street Bar-B-Que. But the crowning achievement will be the residential projects. By the 2030s, people will be moving onto Ookwemin Minising, a new 98-acre island projected to house more than 15,000 people in a mix of low- and mid-rise buildings. The McCleary District will accommodate at least another 13,500. And everything will be easily accessible via the incoming East Harbour Transit Hub.

Related: A brand-new 98-acre island in the Port Lands is ready for its close-up

Next Up
Exciting projects on the horizon for Toronto’s newest neighbourhood

The Equinox Bridge Set to open next year: a 120-metre no-cars-allowed overpass designed to be the perfect place to view the summer solstice sunset and the winter solstice sunrise.

Lassonde Art Trail The city is building a 4.2-kilometre open-air art trail with 15 sites for permanent collections and rotating displays. One of the first will be a painted aluminum sculpture by Kuwaiti artist Monira Al Qadiri.

PlayPark A $75-million, three-acre playground is still in the planning and fundraising stages, but it’s aiming to have twisty tree slides, a splash pad and mammoth-size animal sculptures.

South Parkdale

A bohemian enclave beside a new rapid transit line

4 Liberty Village will soon be home to the western terminus of the Ontario Line, but the real gem is just north of the madding crowds of yuppies. A vibrant new community of young artists, entrepreneurs and families is taking root amid the detached Edwardian and Victorian homes of South Parkdale and Little Tibet.

The neighbourhood, which sits between the Gardiner, Queen West and Atlantic Avenue, is peppered with momo shops, thrift stores and dive bars, and it has managed to retain its edge while welcoming a mix of new businesses. Trendy cafés like Grocery Coffee—overflowing with vinyl, houseplants and a gallery space for special exhibitions—blend into the streetscape so naturally that they feel more like a record collector’s apartment than a place selling $6 lattes.

In short: South Parkdale is to Toronto what the East Village is to New York. And with the upcoming subway access, residents will be able to spread their unique brand of cool all over town.

Shopping Spree
Seasoned thrifters know that South Parkdale has some of the city’s best treasure troves. Here are three spots for one-of-a-kind pieces

High End: House of Vintage A quirky shop with a party vibe and a mirror ball to prove it, House of Vintage offers a curated selection of classic thrifting fare: ’70s belt buckles, cowboy boots, vintage tees, stacks of denim and a lot of plaid.

Mixed Bag: Common Sort Stocked with everyday staples—jeans, dress pants, sweaters, tees—Common Sort sits somewhere between boutique and straight-up donation bin. There’s fashion to be found, but you’ll have to dig for it.

Bargain: Public Butter Charmingly wacky and gloriously over-stuffed, Public Butter is vintage shopping at its most chaotic. Expect a wild rainbow of second-hand treasures at fair prices, from perfectly broken-in denim to Oscar de la Renta.

Yonge-Bay Corridor

Toronto’s downtown core is getting the revamp it deserves

5 Very few major cities still have under-­developed downtowns, but in Toronto, there’s a nine-kilometre strip of land between Front and Bloor that’s been begging for love. The Yonge-Bay Corridor is steps from everything: Sankofa Square, the Eaton Centre, city hall and the Entertainment District. Its connectedness is unparalleled, but for decades the residential scene has been overlooked.

Related: Goodbye, Yonge-Dundas Square. Hello, Sankofa

Now, there’s a massive overhaul planned for the decrepit bus station at Bay and Dundas. In five years, the site will have two new builds, one a mid-rise and one a high-rise, both done in the art deco style of the station at its prime. There will be more than 873 purpose-built rental units between them, plus a paramedics services hub and a community plaza. But that’s just a fraction of what’s coming: there are also mixed-use towers popping up around it—239 Yonge, Massey Tower, Aura and 8 Elm Condos—to prove that this neighbourhood can sustain full-time residents, not just university students or passers-through.

Go Small
A list of must-try indie spots in the land of big box chains

Elm Street Deli What could feel more metropolitan than grabbing an Italian sando at a New York–style deli for lunch?

Bootmaster Go to this western leather-goods purveyor for the stampede-worthy kicks; stay for the turquoise accessories.

Acadia Books Acadia specializes in out-of-print and vintage books. Check out the owner’s selection of antique maps and art prints.

Lao Lao Bar This spot has artfully plated Lao cuisine and colourful decor. Great for the family or a cocktail and snack on date night.

Riverside/South Riverdale

The charming residential ’hood will be home to the Union Station of the east

6 Once a sleepy stretch known mostly for its intersection with storied De Grassi Street, this pocket of Queen East between the DVP and Jones Avenue has emerged as a dynamic strip. Michelin-recognized spots like the White Lily Diner rub shoulders with charming cafés and wine bars while bodegas and beloved takeout joints, like the classic Jamaican Blessed Love, keep the vibe grounded and authentic.

Construction has begun on the East Harbour Transit Hub, a 38-acre GO and TTC interchange just south of Eastern Avenue, so anyone living in Riverside’s mix of charming Victorians, converted historic lofts and modern high-rises will soon be able to easily zip across town. Add in the futuristic 35-storey residential development that’s being planned for the intersection of Broadview and Danforth, and it’s clear that Riverdale’s star (not to mention its property values) is on the rise.

Nice Ride
The East Harbour Transit Hub is a centrepiece of the city’s $70-billion transit expansion plan and will serve an estimated 100,000 daily commuters. Here’s what to expect

Trains Six new tracks—four for the GO and two for the Ontario Line—will allow commuters to zip along Queen Street and up to Eglinton Avenue without having to suffer through Union.

Housing Fifteen new mid- and high-rise buildings will go up above the hub, adding more than 4,000 commercial and residential units. The complex will also include daycare facilities and a community centre.

Parkland Plans for the East Harbour site include 3.5 acres of parks, plus plazas and open spaces linking the waterfront to East Chinatown, Leslieville, the Distillery District and beyond.

The Golden Mile

The crosstown is coming to Scarborough’s culinary hotspot

7 Staunch downtown loyalists may scoff at the idea of living in Scarborough, but the Golden Mile’s mix of mid-century homes on spacious lots, modern high-rises and townhouses offers more than just suburban quiet. This stretch—between St. Clair East, Wexford Park, Victoria Park and Birchmount Road—is fast becoming a destination for food lovers, especially those seeking refuge from the reservation headaches and snootiness of dining in the core.

There are unpretentiously delicious spots like Vienna Fine Foods, a family-owned hot counter and grocery that’s been pumping out expert pork schnitzel and goulashes since 1953, and local favourites like Perlas de Pilipinas and Golconda Toronto. And that’s pre-LRT. Once the Eglinton Crosstown stop at Warden Avenue opens up, connecting the once-isolated area to the rest of the subway system, its transit score—and housing prices—will skyrocket.

Food Tour
Gourmands, get out your pen and paper—we’ve done the vetting for you

Adonis This enormous market specializing in Middle Eastern and Mediterranean foods is one of three Adonis outposts in Toronto. Picture 40 varieties of olives, meat pies and a pita conveyor belt.

Diana’s Oyster Bar Don’t let the strip-mall setting fool you—this offshoot of Diana’s Seafood serves some of the finest morsels in the city. Dinner includes the crowd-pleasing crab, shrimp and lobster tagliatelle.

La Bastille Boulangerie Patisserie This French pâtisserie is owned and operated by Paris-born Martial Ribreau. Try their light, buttery croissants and the kouign-amann—a layered roll sprinkled with sugar and beautifully caramelized.

Bloorcourt/Bloordale

A GO expansion is bringing new life to this west-end culture hub

8 Finding an affordable home in Toronto’s core has never been more challenging, but it’s possible in this eclectic, low-key stretch of Bloor West between Christie Pits and Lansdowne. It has a mix of Edwardian-style row homes and low- to mid-rise walk-ups and is home to vibey staples like the Burdock Brewery taproom and music hall, supper favourite Sugo, and hi-fi listening bar Sounds Good. They sit comfortably alongside stalwarts like Ethiopian Selam and Taqueria El Pastorcito.

By 2027, a new GO station will be running just southwest of Bloor and Lansdowne, topped by a two-tower, mixed-use development from architecture firm Hariri Pontarini. While this wave of gentrification may seem at odds with a community known for its sleepy, artsy energy, nearby anchors like the Paradise Theatre and oddball institutions like the Monkey’s Paw bookstore help ensure that the spirit of the neighbourhood endures.

Art Walk
A mini tour of Bloorcourt and Bloordale’s indie culture scene

Gallery 1065 Owner Monica Gupta transformed the space that used to house her father’s real estate company into a modern venue that highlights west-end artists.

MOCA After giving up its original Queen West digs, Toronto’s long-standing modern art institution, known for exhibiting experimental and local artists, found a new home on Sterling Road.

Mercer Union This contemporary art gallery was established in 1979 by artists sick of seeing cutting-edge work overlooked. Now, it’s housed in a renovated 20th-century movie theatre on Bloor West.

Oakwood Village

The growing pains of a new light rail line are finally paying off

9 Unending construction on the Eglinton Crosstown has wreaked havoc on this neighbourhood, but Oakwood station is really and truly almost done. When it is, Oakwood Village—which extends from St. Clair to Eglinton and Winnett to Dufferin—will get an injection of new life.

Little Jamaica is already home to a steady stream of entrepreneurial bustle: long-standing jerk chicken joints are nestled alongside independent grocers and flower sellers like Best Choice and Yips. Now that direct transit to the rest of the city is on the horizon, the area is poised to become the latest west-end foodie hotspot.

Ossington, Dundas and Geary are well-known, but culinary offerings up here, like carb-haven Primrose Bagel Company and Porzia’s, home of the one-pound slab of lasagna, are becoming must-tries. The neighbourhood’s detached homes and low-rises are also within walking distance of Cedarvale Park, where sugar maples and dogwood trees add a dose of natural calm.

Caribbean Cruise
Who needs a multi-stop vacation? All the best food from the isles is gettable here

Randy’s Takeout This is the best spot for a Jamaican patty, according to basketball star Tristan Thompson, actor Shamier Anderson and Drake.

Rap’s Rap’s is to jerk chicken what Michael Jordan was to basketball—the undisputed GOAT.

Earla’s Kitchen Earla’s is the place to try Grenada’s national dish: breadfruit, salted meat and dumplings in seasoned coconut milk.

Always Fresh (Restaurant Canadian Caribbean) A local favourite, Always Fresh is a sleeper hit for well-executed Caribbean classics.

Downsview-Roding-CFB

The former airport has landed an influx of new development

10 Until recently, reasons to trek to Downsview were scant. The area north of Wilson and east of Jane was known mostly for its 291-acre park and defunct airport. That started to change when Northcrest Developments bought the airport land. Their most headline-grabbing move was hosting the temporary Rogers Stadium, but the real game-changers are still to come.

The neighbourhood is getting seven new districts designed to accommodate more than 50,000 residents over the next 30 years. They’ll be huddled around existing TTC and GO stations and loaded with compact mid-rise buildings and townhouses, adding new diversity to the current landscape of detached single-family homes. The former runway will become a pedestrian promenade, and the whole thing will be surrounded by green space. Canada Lands Company is also bringing five vibrant new communities surrounding the fully protected Downsview Park, which will bring over 22,000 new homes to the area.

Still, it would be a mistake to overlook what Downsview already has on offer. Case in point: the Downsview Park Merchant’s Market is home to more than 500 grocers and vendors, plus a global food court that rivals the Ex’s, which is on Canada Lands’ future Downsview West site.

Cutting Edge
Merchant Market vendor Elias Shaikh runs Exotic Knives and Things, a stall peddling rare blades and other oddities

Why knives? “I’ve had an appreciation for arcane pursuits for a long time. I saw there was a demand for these hard-to-find objects.”

Who’s buying? “Collectors, outdoorsy people, military buffs, the historically inclined and movie lovers chasing props. No cooks, though—I don’t sell kitchen knives.”

Why should people make the trip to Downsview for the market? “The chain-free food court is amazing. I’d recommend Mama Original’s jerk chicken or a Turkish kabab from the tent out front. The fruit and vegetable grocers are an incredible resource too. Their fare is fresh and affordable—there’s zero price-gouging.”

Pape Village

A mediterranean oasis isolated no more

11 The seven-block stretch of Pape between Sammon and Gamble Avenues is a world unto itself. The distinctly local-feeling pocket is lined with early 20th-century Edwardian cottages and a mix of genuinely charming family-run businesses both long-­standing and new. Diner-style spots like Masa Buka—known for its epic gyro plates—share the street with fruit stands, flower shops and convenience stores, some with pragmatic catch-all names like the Everything Store.

Sprinkled in are signs of a new wave of gentrification: the retro-styled Lorenzo’s Pizzeria, or Greek-run café El Greco, which sells handmade koulouri and spanakopita as well as jars of bougie herbs from Crete. And soon, thanks to the forthcoming Ontario Line station at Pape and Cosburn, it will be much more accessible than the Aegean island from which it takes its character—though it’s sure to retain the conversational hum of a small Greek town.

Platonic Ideals
The Danforth gets all the glory, but Pape Village has baklava and other Greek goodies as prized to the neighbourhood as the Golden Fleece. Here’s where to get them

Serano Bakery Pastries and cheeses could easily distract from the real gem: the baklava. Serano’s take on the phyllo classic is the best of its kind.

Masa Buka The standout at this diner-style eatery is the gyro. On the side, thick hand-cut potatoes are twice-fried for maximum crunch.

Phyllo Cafe The heavy hitter here is the Sweetest Torontonian Cheese Pie: layers of phyllo dough stuffed with ricotta and feta.

Pape Village Original Greek Restaurant Come for the giant half-block of Greek feta; stay for the zucchini croquettes. These crisp spheres arrive with a welcome counterpoint: the cool, garlicky tang of tzatziki.

Woodbine-Lumsden

The east end’s final frontier is having its moment

12 Lately, East York has seemed like the last bastion of houses within sniffing distance of affordable. That’s changing fast. Buyers have arrived here in droves, erecting shiny infill and bringing commerce along with them.

There is, however, one last holdout: Woodbine-­Lumsden, the area north of Danforth between Woodbine and Main Street, is still gettable for less. In June, it became one of the nine Toronto wards primed to build sixplexes, preparing it for gentle densification that won’t detract from the character of its current post-war bungalows.

The area already has three subway stations, the nearby Danforth GO and the 62 Mortimer bus, which is the fastest way to reach the Don Valley. But there’s really no need to travel far for a night out. Just pair any one of the nearby restaurants—the Michelin-recognized Wood Owl, the Oak Park Deli or Friday Burger Co., say—with a show at the Comedy Bar Danforth or Coal Mine Theatre.

Super Natural
A roundup of the best spots along gorgeous Taylor Creek

For Hikers: Taylor Massey Creek Trail This three-and-a-half-kilometre stretch winds around old maples and dips under the Woodbine Bridge, extending all the way from the Don River to Warden Woods.

For Nature Seekers: the Wetlands This is the spot to see muskrats, damselflies, orange fish and great blue herons.

For Jocks: Stan Wadlow Park Woodbine-Lumsden’s all-ages playground has a skatepark, athletic fields, an outdoor swimming pool and seven baseball diamonds.

Plus: the Long, Long Plays

Three promising neighbourhoods for the extra patient buyer

Mount Dennis It’s less developed than neighbouring Weston Village, but the Eglinton Crosstown’s terminus station will come with perks. Namely: a bus loop, GO and UP access, and LRT service into Mississauga. The transit accessibility will be unmatched. Bonus: George Brown is considering a new Mount Dennis campus.

Thorncliffe Park This area, nestled in the crook of the DVP just east of Leaside, has long been underserved by transit. Soon the Ontario Line will connect it to the rest of the city. The station will come with a massive mixed-use development, and residents will be just steps from doctors, daycares and more at the area’s fancy new community hub.

Willowdale Willowdale already has luxury condos and charming bungalows. Soon, Finch station will connect the yellow line with the Yonge North subway extension. Couple that with a revitalization project and a wave of new residential towers and you have an already successful neighbourhood bound to appreciate even further.