106 Highland Avenue

ActiveRosedale / Moore Park · Rosedale-Moore Park3 days on marketMLS® C14107036

$3,629,000

$1,452 / sq ft

Bedrooms5

Bathrooms5

Interior2,500 sq ft

TypeSemi-Detached

ListingFor Sale

Days on Market3

About this property

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.

Features & finishes

Fireplace

Air Conditioning

Basement

Property details

MLS® Number	C14107036
Status	Active
Listing Type	For Sale
Property Type	Semi-Detached
Interior Size	2,500 sq ft
Beds / Baths	5 bed · 5 bath
Property Taxes (2026)	$16,458
Neighbourhood	Rosedale-Moore Park
City	Rosedale / Moore Park
Postal Code	M4W 2A6
Province	ON
Listed Date	October 22, 2026
Days on Market	3
Price per Sq Ft	$1,452
Brokerage	SOTHEBY'S INTERNATIONAL REALTY CANADA