106 Highland Avenue, Toronto

106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
+46
4+1
 bed
5
 bath
2
 parking
2500 - 3000
 sqft
Semi-Detached
$3,750,000
For Sale
8 hours
 on site
$3,750,000
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Size
-
Lot size
5669 sqft
Street frontage
-
Possession
Flexible
Price per sqft
$1,250 - $1,500
Taxes
$16,458 (2026)
Parking Type
-
Style
2 1/2 Storey
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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.
Broker: SOTHEBY'S INTERNATIONAL REALTY CANADA
MLS®#: C13818260
Property details
Parking:
2
Parking type:
-
Property type:
Semi-Detached
Heating type:
Forced Air
Style:
2 1/2 Storey
MLS Size:
2500-3000 sqft
Lot front:
38 Ft
Lot depth:
148 Ft
Listed on:
Sep 23, 2026
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Instant estimate:
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$74,745
lower than listed price
i
High
$3,840,233
Mid
$3,675,255
Low
$3,519,372
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About 106 Highland Avenue

106 Highland Avenue is a Toronto semi detached house for sale. 106 Highland Avenue has an asking price of $3750000, and has been on the market since September 2026. This 2500-3000 sqft semi detached house has 4+1 beds and 5 bathrooms. 106 Highland Avenue resides in the Toronto Rosedale neighbourhood, and nearby areas include Moore Park, Bennington Heights, St. James Town and Yonge and Bloor.

For grabbing your groceries, Summerhill Food Market is a 5-minute walk.

If you are looking for transit, don't fear, 106 Highland Ave, Toronto has a public transit Bus Stop (Highland Ave at Glen Rd) only steps away. It also has route Sherbourne, and route Rosedale close by. If you're driving from 106 Highland Ave, you'll have decent access to the rest of the city by way of Don Valley Parkway as well, which is within a few minutes drive