After 20 years of living in Hogg’s Hollow, I can say this with conviction: few neighbourhoods in Toronto feel so quietly extraordinary.
And the kicker? Most people haven’t even heard of it. Tucked into a steep, wooded ravine just off Yonge Street and improbably served by the subway, Hogg’s Hollow has a kind of secret-garden quality—lush, hushed, and seemingly miles from the city’s chaos.
New visitors are often startled that such a green and hidden pocket exists in the heart of Toronto. I still run most errands on foot—groceries, the bank, the barber—and take the subway more often than I drive, mostly to avoid the existential despair of midtown traffic.
A short stroll through the park gets me to the Miller Tavern, which has been holding court on that corner since the 1850s.
My own home sits at the end of a quiet cul-de-sac, where the land rises and folds in unexpected ways, more reminiscent of British Columbia than midtown Toronto. It’s shaded by a stand of 150-year-old white pines, which tower overhead and cast long, cathedral-like shadows in the morning light.
While that topography and tree canopy aren’t found on every lot in the neighbourhood, they reflect the essence of what Hogg’s Hollow offers: a profound sense of retreat and immersion in nature. Many homes are nestled into slopes or set back beneath a canopy of mature maples and oaks, with ravine views and wildlife never far off.
Even my Parisian family, who are generally diplomatic in their preference for the City of Light, can’t help but admire this particular corner of Toronto. The presence of deer, coyotes, raccoons, and the occasional red-tailed hawk doesn’t hurt either—nor does Cooper, my tiny goldendoodle and self-declared mayor of the ravine, who has built quite a local fanbase through a mix of charm, consistency, and humping my leg while I try to chat with fellow dog walkers.
The Charm and History of Hoggs Hollow
This neighbourhood wears its layers well. From the Georgian and English cottage-style homes of the 1920s to the mid-century Modernist gems—and yes, even the occasional contemporary residence that gets it right—there’s an organic rhythm to the streetscapes here. It’s not all perfectly preserved, mind you.
There are a few architectural missteps, to put it politely—houses built more for show than soul—but many homeowners have managed to blend ambition with grace. I’m always grateful for those larger homes that respect their context, and for the mid-century and early 20th-century houses that have been lovingly updated rather than erased. This mix, this refusal to conform to a single style or era, gives Hogg’s Hollow its rare character.
Of course, Hogg’s Hollow didn’t always look this way. Long before the subway tunneled under it and the Miller Tavern got its polished restoration, this was a working mill town, named after James Hogg, a Scotsman who arrived in 1824 and set up a whisky distillery and a grist mill.
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The area was originally subdivided in 1856 by Hogg’s sons, though development came in fits and starts—bogs, swamps, and the occasional patch of quicksand made construction… challenging. Still, the community formed around the essentials: a school, a church, a blacksmith, a store, and eventually golf links.
The name stuck. Since then, Hogg’s Hollow has grown in waves—first in the 1920s, and later through the post-war decades—always retaining a rural air that defies its urban location. Today, it’s a pocket of charm in a city increasingly losing its rough edges. The streets curve instead of grid, there are no sidewalks, and the whole place feels more discovered than designed.
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But what really makes the Hollow sing is the architecture — and the attitude. The homes here aren’t all the same, nor should they be. Some are old friends, some are beautifully revived, and a few are fresh additions that simply get it right.
What they share is something harder to define: character, restraint, a sense of place. So in the entries that follow, I’ve pulled together a personal collection — a kind of walking tour of the most interesting homes in the Hollow.
Think of it as a love letter to the houses that make me stop, stare, and maybe secretly wish I’d designed them myself.
2 St. Margaret’s – 1934
With its steeply pitched roof, arched dormers, and red front door peeking through ivy-clad brickwork, this French Norman Revival home feels plucked from a storybook. Nestled on a quiet, leafy street, it pairs old-world charm with enduring curb appeal. Manicured gardens, classic proportions, and a dignified silhouette make this a true standout—quietly grand, unmistakably refined.
4 Hedgewood – 1914
Set back on a sweeping, tree-framed lot, this stately brick residence is a masterclass in American Georgian style—with its symmetrical façade, blue-green shutters, classical columns, and dignified hipped roof. The wide veranda and gravel drive lend it a relaxed, East Coast country club air—think understated wealth, not ostentation. It’s the sort of house that doesn’t shout, but rather nods politely from behind its boxwood hedges.
15 St. Margaret’s – 1953
Tucked deep into the forested fold of the valley, this long-forgotten gem looks like it was designed by a disciple of Frank Lloyd Wright and then left for nature to slowly take back. The horizontality, natural materials, and quiet presence are classic 1960s modernism—but softened by vines, moss, and towering maples. It’s as though someone built their dream house, then handed the deed to the forest. A haunting, romantic reminder of how good design can dissolve into its surroundings—and sometimes vanish altogether.
19 Hedgewood – 1937
Ah, now this is one of those houses that quietly commands respect. A classic example of French Provincial architecture with a Toronto twist, this yellow-brick beauty is defined by its steep, cedar-shingled mansard roof and symmetrical dormers — equal parts charm and authority. The arched portico over the front door feels like a polite bow, while the shutters and sash windows add a sense of order that’s wonderfully unpretentious.
It’s the kind of home that looks like it might belong to a retired ambassador, now tending to espaliered pear trees and debating philosophy with his dog. And despite its formal appearance, it nestles into the ravine setting as naturally as a foxglove in spring. A quiet standout in a neighbourhood known for showy contemporaries and sprawling estates, this one wins on restraint and refinement.
19 Plymbridge – 2024
Understated, monolithic, and utterly magnetic, this is modernism at its most disciplined. Clad in slender Roman bricks and barely revealing an expression beyond the recessed entry and muted second-storey glazing, the architecture seems to whisper rather than shout — and somehow that makes it all the more compelling.
This home could easily be mistaken for a private gallery or the lair of a minimalist Bond villain with impeccable taste. It’s a study in proportion and shadow play, with every line deliberately placed to heighten the mystery. The landscaping is restrained but strategic — almost like a curated silence around a profound thought. It doesn’t beg to be noticed… but you notice it anyway.
21 Brookfield – 2014
This remarkable home might look like a preserved modernist gem from the 1960s, but in fact, it’s a contemporary masterpiece with impeccable retro credentials. Designed and built about a decade ago by a university classmate of mine (clearly still at the top of her game), it channels the disciplined elegance of late modernism without ever feeling like a pastiche.
The rhythmic façade, crisp geometry, and elevated glazing evoke the era of Mies, yet the execution is unmistakably current — precise, clean-lined, and utterly intentional. It’s a house that understands its architectural ancestry but doesn’t feel the need to cosplay it. A rare feat in any era, and one that settles into the snowy ravine landscape like it’s been there all along… just quietly outclassing the neighbours.
28 Beechwood – 1966
There’s a particular kind of charm that only a stone Georgian can deliver — and this one does it with enviable confidence. With its symmetrical façade, dignified shutters, and pedimented entry framed in delicate tracery, it feels like it could have been lifted from the pages of Country Life and quietly resettled here in Hogg’s Hollow.
What makes it special, though, isn’t just its textbook proportions — it’s the soft patina of ivy traces on the stone, the weathered copper flashing, and that generous wreath that says, “yes, this house knows how to do Christmas properly.” It’s elegant without being precious, traditional without veering into parody. A little slice of New England grace tucked into the Toronto ravine — and better for it.
35 Brookfield – 1951
Even cloaked in evening shadows, this house exudes a quiet confidence — the kind of home that doesn’t need daylight to make an impression. With its steep gables, symmetrical windows, and that arched upper sash glowing like a lantern, it feels like something out of a well-heeled New England village, reinterpreted with Toronto restraint.
The textured stucco, classical trim, and boxwood hedges all play their part, but it’s the atmosphere that wins you over — warm light spilling from the windows, a discreet Canadian flag fluttering by the portico, and a sense that inside, there’s likely a roaring fire, a well-stocked drinks tray, and someone making a perfect omelette. It’s not flashy. It’s just… right.
40 Brookfield – 1964
Now this is how you honour the mid-century spirit without falling into caricature. Originally a 1960s home, it’s been thoughtfully expanded and reimagined by its current owners — not as a departure, but as a deepening of the original design language. The result? A home that feels both grounded in its era and utterly current.
The crisp white brick, rhythmic fenestration, and dramatic glass bridge are pure architectural theatre — but the kind performed with subtlety and taste. You get the sense that every update was made with reverence, as if the house itself had a say in the matter. It’s warm, sophisticated, and brilliantly lit at night — almost cinematic in its glow. A perfect example of what can happen when heritage and ambition strike the right balance.
49 Donwoods – 1940
If Norman Rockwell had been Canadian and partial to Georgian Cape Cods, this might’ve been the house he painted. Framed by its storybook picket fence and glowing like a warm invitation on a cold December night, this home is the architectural equivalent of a perfectly timed hug.
Those symmetrical dormers, charming shutters, and classic centre-hall proportions all speak to timeless American vernacular — but the execution here feels elevated. The crisp white brick, restrained palette, and those festive wreaths in every window are almost comically perfect. It’s like a holiday card that happens to be real, right down to the reflections on the wet pavement. If you squint, you might catch a golden retriever dozing by the fire just inside.
50 Donwoods – 2018
This one’s a masterclass in architectural theatre — and proof that new doesn’t have to mean forgettable. With its tall chimneys, steeply pitched gables, and crisply defined stonework, it reads like an English manor that’s spent a sabbatical in Toronto and come back better dressed.
Despite its scale, there’s nothing ostentatious here — just strong proportions, exceptional materials, and a symmetrical rhythm that makes the whole façade feel grounded and composed. The lighting is subtle but strategic, drawing you in through that sculpted stone entry like a warm handshake. And those black-trimmed windows? A quiet, contemporary wink amid the otherwise classical restraint.
In a neighbourhood where some new builds try too hard, this one simply gets it right. A worthy addition to the canon of Hogg’s Hollow houses that make you stop, stare, and maybe secretly wish you’d designed it yourself.
75 Donwoods – 1927
This is the kind of house that doesn’t perform for the street — it simply belongs. With its shingled second storey, classic red brick base, and perfectly symmetrical shuttered windows, it’s a Colonial Revival gem with the quiet confidence of something that’s been loved — and lived in — for generations.
In fact, it has. This home has been in the same family for nearly 60 years (or more), and you can feel it in the details: the mature hedges clipped just so, the patina on the shingles, and that engraved stone at the driveway that feels less like a label and more like a signature. Nothing’s overdone. Everything’s just right. A house with history, and not the kind that needs a plaque to prove it.
104 Donwoods – 1937
This one’s a fairytale with a second act — and thankfully, it’s no longer the haunted kind. After years of looking forlorn and nearly forgotten, this turreted stone charmer has just emerged from a respectful and much-needed revival, and the result is nothing short of magical.
There’s something innately romantic about the curved walls, leaded windows, and steep gables — like it was plucked from a Bavarian hillside and dropped into the ravine, then politely overgrown. But now, with its copper roof gleaming again and the stonework scrubbed back to life, it feels like a long-lost character who’s just been given their lines back. Whoever took this on had the rare good sense to preserve its quirks, not erase them.
Not every house gets a second chance. This one took it — and absolutely ran with it.
Would You Like a Closer Look at Hoggs Hollow?
There you have it — thirteen homes, each with its own point of view, its own charm, and its own role in the larger story of Hogg’s Hollow. Some are venerable old souls, others are bold newcomers, and a few are glorious comebacks worthy of their own HGTV spinoff. Together, they form a kind of architectural patchwork: not matching, but harmonious. Not perfect, but interesting — which is, I’d argue, much better.
It’s easy to love a neighbourhood for its houses. But the truth is, you stay for the way it feels. The way light filters through the trees at dusk. The neighbours you wave to on walks. The way it dramatically shows off the distinct seasons. And the tiny dog with delusions of political office who insists on introducing you to everyone.
Hogg’s Hollow may not be on every Torontonian’s radar — and frankly, we’re fine with that. The place wasn’t built to be noticed. It was built to be lived in. And for those of us who call it home, that’s more than enough.
If you have real estate (or architecture) questions, I’m always happy to chat. Get in touch with me today by filling out the form on this page, calling me at 416-824-1242, or emailing me at robert@lifeofluxury.ca.
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