How property flippers transformed an entire street of Toronto ‘strawberry box’ homes

Two weeks before Christmas in 1947 — the year the Maple Leafs won the Stanley Cup over rival Montreal Canadiens — a mystery artist placed a sweet classified ad in the Toronto Star to drum up some cash.
“Being an artist still alive, I paint pretty scenes you can buy … Tiny studio, tiny artist, tiny prices,” the ad stated. The artist didn’t give their name, just an address on Exmoor Drive in the Long Branch neighbourhood of Etobicoke.
The artist’s little house — with white siding and lace curtains in the front window — was purchased for $300,000 by a local builder at the end of 2018.
It was one of just nine squat, single-storey homes on a short stretch of road with a front-row view of a bustling transit loop. These “strawberry boxes” — so named for their resemblance to the pint-sized containers farmers use to pack strawberries — with square foundations, simple gabled roofs and brick or wood exteriors once dotted neighbourhoods across Etobicoke and beyond. Many were built en masse during the Second World War for factory workers who produced items used in battle and later for returning veterans and their families.
As veterans passed away, homes like these provided one of the most affordable entry points in the city’s real estate market for young families.
In the past decade, nearly all of the strawberry boxes on Exmoor Drive have been demolished and replaced with what the local neighbourhood association calls “soldier homes” — not in a nostalgic nod to the past but a swipe at their uniform aesthetic: “generic, tall and skinny.”
Since 2015, nine new custom homes have replaced the strawberry boxes on “the little island of Exmoor,” as the neighbourhood association calls it. Some builders severed the existing 50-foot lots to construct two homes instead of one, raising the total number of homes on the island to 12 from nine. The transformation has also boosted property values despite the fact the homes are on a dead-end street sandwiched between a Go rail line and the city’s transit loop.
The transformation has pushed these homes out of reach for many Toronto families, as the new homes cost at least twice as much as the ones they replaced. Even the old homes that are left have become too expensive for families as they’re priced to reflect the land’s potential instead of the house that’s sitting there. A spokesperson for the construction company that launched the big flip of Exmoor Drive says the cost of land is now even out of their comfort zone.
Flipping is big business across the Greater Toronto Area, where nearly 30 per cent of existing housing was built in 1960 or before. Re/Max Canada flagged renovations and rebuilds as “one of the most underestimated factors” driving up the value of detached houses, which has shot up 35 per cent from 2019 to 2023. A Toronto Star analysis of demolition permit and sales records for single family homes in Toronto found the work of flippers has resulted in home prices more than doubling in some pockets of the city in recent years.
Since 2020, three of the new custom builds on Exmoor Drive have been resold at an average price of nearly $1.4 million from an original average price of $490,000.
Two weeks ago, realtor Andrew Ipekian brought a new listing on Exmoor Drive to the market. While the interior of the 950-square-foot, three-bedroom, one-bath home with a basement apartment is renovated, the exterior echoes the storied strawberry box. But this one is on an extra-wide lot. At $1,198,000, the price tag is not a measure of the house itself but what it could be.
“Welcome to 50 Exmoor!” the online listing says. “Ideal for investors, builders or end users! Consider severing into two 25ft lots for new builds, renovate or expand the home to suit your needs.”
“On a 25-foot-wide lot, on average, you can get approximately a 2,000-square-foot home above ground, plus the basement with a built-in garage,” Ipekian explains in a phone call.
Scag Holdings Inc., the Toronto-based construction company that first saw the potential of Exmoor Drive, purchased three strawberry boxes on the strip starting in the summer of 2012 and replaced them over the next several years with five custom homes.
While the Go train was loud and the street traffic constant, investors saw the proximity to multiple modes of transit as a benefit rather than a drawback and bet others would, too.
“We took a risk,” a spokesperson said. “A lot of people questioned whether we’d sell those houses at all.”
But they did sell. And with handsome-enough profits to attract new flippers to the area and drive up values of the three original strawberry boxes that remain on Exmoor Drive. The spokesperson said the company would have done more but the cost of land became too expensive.
David Godley, a former urban planner who resided in Long Branch and coined the term “soldier homes,” is worried about the loss of affordability in the neighbourhood but says what happened on Exmoor Drive alone isn’t to blame.
Real estate investors quickly found lot severing to be a profitable business in Long Branch so Godley worked with the local neighbourhood association to help preserve the character that remained. They successfully petitioned the city to approve a formal set of “character guidelines” for future developments.
City Council approved the guidelines in 2018, directing staff to apply them in reviewing all development applications and public initiatives for land bounded by Lake Ontario to the south, the rail corridor to the north, Twenty Third Street to the east, and Forty Second Street (including Marie Curtis Park) to the west. It’s the only neighbourhood in Toronto, city staff confirmed, to have its own set of character guidelines.
The transformation of Exmoor Drive was well underway by the time the new rules came into play.
“These new homes don’t meet the guidelines at all,” says Christine Mercado, chair of the Long Branch Neighbourhood Association. “There were numerous and not minor variances granted to make those applications work. They’re too close to the lot lines. There is almost no tree planting space left and the backyards are quite small.”
Vanessa Covello, a senior community planner with the City of Toronto who oversees Etobicoke—York District, said the guidelines alone “can’t deter lot severances.” Provincial policies and the city’s official plan “will still determine the suitability of lot severances and it’s all based on the character of the existing lot sizes in the neighbourhood.”
The Toronto builder who bought the artist’s strawberry box for $300,000 at the end of 2018 didn’t want to talk about his work for this story.
The tiny house was rebuilt during the pandemic into a two-storey, four-bedroom, three-bath modern luxury home with 12-foot ceilings and a waterfall island in the kitchen.
The property was listed for $1,499,900 and sat on the market for a month before the price dropped to $1,399,900.
Five days later, at the end of 2020, it sold for $1.415 million — a record high on Exmoor Drive.