Spiteful, stubborn and surviving: How these Winnipeg holdout homes have stood the test of time

By Katherine Dow
Published: February 14, 2026 at 7:00AM EST

We all know Darwin’s theory of survival of the fittest, often misquoted by stale memes and bad motivational posters and a certain hack reporter.

The gist - those who endure are those who adapt.

Still, a walk down Graham Avenue in downtown Winnipeg seems to suggest an architectural counterpoint to Darwin, that a certain stubbornness can also be a necessity to survival.

I’m writing of 415 Graham Avenue.

Nestled quietly behind a shoe repair and a coffee shop, peeking up just above the traffic lights and the store facades, sits a house.

“The house is still there at the heart,” explained Christian Cassidy, a Winnipeg history blogger.

“Even though you have much more modern retail development around it, it’s still there at the heart of that development.”

The home, barely visible today, is over 120 years old.

Built on Graham Avenue at the turn of the 20th century, the superintendent of the Winnipeg Street Railway was its first known owner.

According to Cassidy’s research, he had just moved west from Toronto, Ont. with his wife to take the gig.

They didn’t last long, packing up about a year later, en route to a home on nearby Assiniboine Avenue.

In the decades since, Graham transformed and, in some regard, the home did too, from a rooming house in the early 1900s, to the backdrop of a single-storey retail extension built squarely in front of it in the late ‘30s.

Those storefronts have since housed a craft centre, a girls’ fashion shop, a beauty salon, a bridal boutique and a thrift store, to name a few.

As the businesses and Winnipeg Transit corridor came and went, the home still sat patiently behind it, just as it does today.

‘Kind of a throwback’

The Graham relic is one example of an urban phenomenon that can go by many names, be it stubborn or holdout houses.

The Larry David set might prefer to call them spite homes.

In China, the term is “nail houses,” meant to elicit an old adage of steely determination, of digging in.

The city planning or legal term- non-conforming properties - eschews flowery language for function.

To Cassidy, they’re lonely houses.

But a lonely house by any other name still means the same thing—a property that remains in place, firmly planted, as the neighbourhood around it evolves in a slow but steady urban expansion of high-rises and infill and change.

These lonely homes hold a certain fascination for Cassidy, who researches and writes of their histories on his excellent blogs, “Winnipeg Places” and “Winnipeg Dumplings.”

Homes that never made the history books are the bite-sized morsels of information that interest him most.

“Lonely homes are always interesting, kind of a throwback,” he said.

“You have an idea of a neighbourhood or a district of the city, and then that just kind of throws you back to, ‘Wait a second. People once lived in this neighbourhood. This is where people raised their families.”

A home ensnared in a real estate scandal

Lucky for Cassidy, Winnipeg has many such throwbacks whose fascinating histories he generously shared with CTV News.

His favourite – Kelly House.

The historic Queen Anne-style home at 88 Adelaide Street was built in 1882, as the transcontinental railway chugged into Winnipeg, positioning the fledgling Prairie metropolis as the Chicago of the North.

The home takes its name from Thomas and Michael Kelly, the brothers who owned the land. If those names ring a bell, you paid attention in civic history.

Their construction company got caught up in the 1913 Manitoba legislature construction scandal.

According to the Manitoba Historical Society, the company bid unusually low on the project and was promptly hired for the build.

Thomas Kelly was later accused of inflating material and labour costs, ultimately blamed for overcharging the Manitoba government to the tune of $1 million.

Thomas served two years in prison for the scandal and headed for America upon his release.

Kelly House, on the other hand, didn’t budge, even as the factories and warehouses expanded to that edge of the Exchange District, swallowing neighbouring homes in its path.

“It has been said that that’s kind of the reason why that house still stands, because Thomas Kelly’s whole estate was kind of tied up in this legal limbo and between family members, and they didn’t know what brother owned what property,” Cassidy explained.

The home was municipally designated a historic site in 2010 and won a Heritage Winnipeg Preservation Award the year after.

Earlier this month, it went up for lease.

“An opportunity to call this your new signature location in the West Exchange. A fully modernized heritage building,” the listing reads.

A piece of Winnipeg punk history

Stroll south of Portage Avenue onto Fort Street, past surface parking lots and The Pyramid Cabaret, and you’ll come upon another of Cassidy’s notable lonely houses.

A one-storey, wood-framed home painted dusty sky blue is wedged snuggly against a storage garage, looking perfectly out of place.

This is Squires House.

“It’s just a little house,” Cassidy explained.

“It was built in 1902 and somehow. that house managed to survive all this commercial development that took place around it.”

According to the Manitoba Historical Society, the first occupant was cab driver William Squires and his family. They moved out in 1904, and it remained a single-family home well into the ‘70s.

“In the 1980s, the house was the centre of the city’s punk music community,” the Manitoba Historical Society writes.

The leather and mohawks left later that decade, as the home became office space for an archaeological consulting company.

It gained and lost historic designation status over the decades, alongside countless residential and commercial tenants.

It’s currently owned by Westgate Developments.

Westgate president Justin Beaulieu still remembers when he first came across the little house that lasted, while walking to meet a friend.

At the time, he was already trying to buy two other adjacent buildings.

“I thought, ‘What is this house doing here in the middle of downtown? What are the chances that we’re literally trying to buy these two buildings?’” he recalled.

The company purchased the home a few years ago in speculation of closing a sale on the two other lots—a deal that has since fallen through.

Now, Beaulieu is trying to sell.

He thinks the small house would suit a small business perfectly.

“If there’s basically someone starting out, a small operation or a couple-person law firm or accounting, you can get your downtown presence.”

Lonely house gets new lease on life

Still, some lonely houses don’t stay lonely for long.

Case in point – Kerr House.

According to the Manitoba Historical Society, it was built in 1887 for educator Francis Ferguson Kerr at the corner of Qu’Appelle Avenue and Balmoral Street opposite the Manitoba College grounds.

The Second Empire Victorian-style home changed hands many times over the years until it came under threat of the wrecking ball in the late ‘80s.

“Around that Central Park area, a lot of those big old houses were torn down and modern apartment blocks were built, including Manitoba Housing, and things like that,” Cassidy explained.

To respond to the new neighbourhood, the government planned to tear down Kerr House and its neighbouring homes to make way for Sister MacNamara School.

That’s when architect Giovanni Geremia stepped in.

Having immigrated from Italy when he was 10, Geremia spent his childhood fascinated by the countless historical buildings that surrounded him.

He bought the home from the city for $1 on the condition it be moved. That ran him another $30,000 to lift it off its foundation and truck it to its new lot on Assiniboine Avenue, where it sits today.

Geremia spent the next year restoring the historic home from the inside out, even adding a small replica building next to it, serving as an entrance to a stairwell to the lower level.

His architecture firm moved in and practiced there for decades.

“I’ve had painters in here saying, ‘I painted this house before.’ I’ve had people say, ‘I used to date somebody there. I saved the house from a fire,’” he recalled.

“That whole history disappears as soon as the building disappears.”

Now in his retirement, Geremia counts Kerr House’s restoration as one of the most meaningful projects of his career.

“There is not a day that I come to this building and say, ‘Why am I here again?’ It’s just an incredible building.”