The Jennifer Jones Team, LPT Realty, Brokerage
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Toronto, ON

106 Highland Avenue

$3,629,000

Data last updated Oct 31, 2026, 7:10 p.m. ET. By using this site you agree to our Terms of Use.

Semi-detached at 106 Highland Avenue, Toronto, ON
106 Highland Avenue, Toronto, ON, photo 2106 Highland Avenue, Toronto, ON, photo 3

Property facts

Price
$3,629,000
Type
Semi-detached
Bedrooms
4
Bathrooms
5
MLS®
C14107036
Status
active
Brokerage
SOTHEBY'S INTERNATIONAL REALTY CANADA

About this home

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.

Location

Search the full MLS®

More details

Property tax
$16,458 (2026)
Days on market
10
Style
2 1/2 Storey
Year built
100+
Lot
38.18 × 148.49 Feet
Parking
2 spaces · None
Basement
Finished, Full, Separate Entrance
Heating
Forced Air
Air conditioning
Central Air
Neighbourhood
Rosedale-Moore Park
Major intersection
Highland Ave and Glen Rd

Rooms

RoomLevelSize (m)Features
Living RoomMain5.08 × 4.14hardwood floor, gas fireplace, overlooks frontyard
RecreationLower5.11 × 4.78hardwood floor, above grade window, pot lights
KitchenMain15.75 × 8.99hardwood floor, centre island, breakfast bar
Bedroom 3Third5.23 × 3.86hardwood floor, b/i closet, skylight
Bedroom 5Lower4.27 × 2.95hardwood floor, above grade window, closet
Family RoomMain3.45 × 3.25hardwood floor, french doors, w/o to garden
Primary BedroomSecond4.04 × 3.66gas fireplace, walk-in closet(s), 5 pc ensuite
Dining RoomMain4.78 × 3.78hardwood floor, open concept, overlooks family
Bedroom 4Third4.98 × 3.35hardwood floor, large closet, closet organizers

Details from PropTx (TRREB MLS®) via Repliers. Information deemed reliable but not guaranteed.

Home value