$3,750,000
106 Highland Ave
Toronto C09, ON M4W 2A6
106 Highland Ave, Toronto C09 — Listed at $3,750,000. 5 bedroom, 5 bathroom 2 1/2 Storey Semi-Detached. MLS® C13818260.
Possession · seller's timeline
Flexible (30-90 Days)
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Description
There's a certain kind of house that feels made for family life, and 106 Highland Avenue is exactly that. Set well back from the street on an exceptional 39' x 150' lot in prime North Rosedale, this handsome red-brick semi offers privacy, space and permanence. Approximately 4,000 sf (total). Completely renovated in 2015 by architect Peter Higgins, it pairs remarkable craftsmanship with thoughtful, enduring design. Step into the foyer, where heated floors & a fluted wood feature wall offer the first glimpse of the detail found throughout. The main floor features a chef's kitchen with Wolf & Miele appliances and generous island seating, opening to a large dining area. Beyond, the family room overlooks the expansive rear garden, while the elegant living room features a gas fireplace & stone mantel. Upstairs, the private primary suite offers 2 walk-in closets, its own gas fireplace, & a beautifully appointed ensuite with deep soaker tub. A 2nd spacious bedroom includes a 4-piece ensuite & walk-in closet. The 3rd floor features 2 oversized, light-filled bedrooms with custom built-ins, a shared 3-piece bath and an additional laundry room. The L/L is exceptionally functional, with high ceilings & a walkout. A heated-floor mudroom provides plenty of storage, while the expansive rec room offers space to play & work, including a dedicated office area. An additional bedroom or gym, 3-piece bath & laundry room complete the level. Outside, the rear garden is beautifully centred around an elegant fountain, creating a tranquil setting for entertaining. A long private driveway & the home's generous setback create an added sense of privacy, while a covered side storage area keeps bikes, & all the equipment of family life neatly out of the way. Walk to Summerhill Market for Saturday-morning groceries, wander the nearby ravine trails, & enjoy close proximity to Branksome Hall & Whitney Junior P.S.- all while coming home to a quiet, established North Rosedale street.
Property Details
Property Insights
Listing Courtesy of: SOTHEBY'S INTERNATIONAL REALTY CANADA
MLS® #C13818260


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HouseIndex Take: 106 Highland Avenue
This semi-detached (2 1/2 Storey) is located in the Rosedale-Moore Park neighbourhood of Toronto.
The home offers 5+1 bedrooms, 5 bathrooms.
Features include a finished, full, separate entrance basement, 2 parking spaces, a fireplace.
Additional details: lot dimensions of 38.18 × 148.49 feet.
Listed at $3,750,000 CAD with annual property taxes of $16,458 (2026).
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About Toronto Real Estate
This Semi-Detached is located in the Rosedale-Moore Park community in Toronto. Toronto is Canada's largest city and the economic hub of the Greater Toronto Area. With world-class transit, diverse neighbourhoods from the Annex to Scarborough, and proximity to major employers in the Financial District, it remains the most sought-after real estate market in Ontario. Buyers benefit from extensive GO Transit and TTC subway connectivity. Semi-detached homes in Toronto provide freehold ownership at a more accessible price point, appealing to first-time buyers and young families.


















































