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$3,750,000

106 Highland Ave

Toronto C09, ON M4W 2A6

106 Highland Ave, Toronto C09Listed at $3,750,000. 5 bedroom, 5 bathroom 2 1/2 Storey Semi-Detached. MLS® C13818260.

Just listed — 1 day ago

Possession · seller's timeline

Flexible (30-90 Days)

5Beds
5Baths
2500-3000sqft
Semi-Detached
2 1/2 Storey
2Parking
$16,458Taxes/yr · 2026

What's this home worth?

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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 TypeSemi-Detached
Style2 1/2 Storey
CommunityRosedale-Moore Park
Approximate Age100+
Rooms8+2
Kitchens1
Washrooms5
Square Feet2500-3000 sqft
Lot Dimensions38.18 × 148.49 ft
Fronting OnNorth
Dir/Cross StHighland Ave and Glen Rd
Garage TypeNone
DrivePrivate
Parking Drive Spaces2
Total Parking Spaces2
ExteriorBrick
RoofAsphalt Shingle
FoundationConcrete
BasementFinished, Full, Separate Entrance
Fireplace FeaturesNatural Gas
Heating TypeForced Air
Heating SourceGas
A/CCentral Air
SewersSewer
Taxes (2026)$16,458
HSTIncluded In
SecurityAlarm System, Monitored, Smoke Detector, Carbon Monoxide Detectors
Listed Date9/23/2026
Days on Market1 days
Possession30-90 Days
Same-day showings available
5.0Rated 5 stars on Google ReviewsWhatsApp Us About This Listing

Property Insights

Home Value
Estimate

Listing Courtesy of: SOTHEBY'S INTERNATIONAL REALTY CANADA

MLS® #C13818260

TRREBMLS®

The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The listing data is deemed reliable but is not guaranteed accurate by TRREB. The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.

© 2026 Toronto Regional Real Estate Board. All rights reserved.

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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.

TTC subway & streetcar networkWorld-class dining & entertainmentUniversity of Toronto & major hospitals nearbyWaterfront trails & ravine parks
Walkability: Highly walkable — many neighbourhoods score 80+ on Walk Score
View full Toronto neighbourhood guide →