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.
For sale
C$3,750,000
106 Highland Ave, Toronto, ON M4W 2A6
5beds
5baths
Single Family Residence
Built in ----
5,669 Square Feet Lot
$-- Zestimate®
C$--/sqft
C$-- HOA
What's special
Handsome red-brick semiHeated floorsFluted wood feature wallGenerous island seatingLarge dining areaAdditional laundry roomLong private driveway
- 9 days
- 84
- 5
Zillow last checked:
Listing updated:
Listed by:
SOTHEBY'S INTERNATIONAL REALTY CANADA
Source: TRREB,MLS®#: C13818260
Originating MLS®#: Toronto Regional Real Estate Board
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
Bedroom 3
- Level: Third
- Dimensions: 5.23 x 3.86
Other
- Level: Second
- Dimensions: 5.61 x 3.28
Dining room
- Level: Main
- Dimensions: 4.78 x 3.78
Heating
- Forced Air, Gas
Cooling
- Central Air
Appliances
- Included: Bar Fridge, Built-In Oven, Countertop Range
Features
- ERV/HRV, In-Law Suite, Storage, In-Law Capability
- Flooring: Carpet Free
- Basement: Finished,Full,Separate Entrance
- Has fireplace: Yes
- Fireplace features: Natural Gas
Interior area
- Living area range: 2500-3000 null
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Private
Features
- Stories: 2.5
- Exterior features: Year Round Living, Landscaped
- Pool features: None
- Waterfront features: None
Lot
- Size: 5,669 Square Feet
- Features: Park, Public Transit, Rec./Commun.Centre, School, School Bus Route, Ravine, Irregular Lot
Details
- Parcel number: 211160140
- Other equipment: Sump Pump
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Brick
- Foundation: Concrete
- Roof: Asphalt Shingle
Utilities & green energy
- Sewer: Sewer
Community & HOA
Community
- Security: Alarm System, Monitored, Smoke Detector(s), Carbon Monoxide Detector(s)
Location
- Region: Toronto
Financial & listing details
- Annual tax amount: C$16,458
- Date on market: 9/23/2026
Price history
Price history is unavailable.
Public tax history
Tax history is unavailable.
Climate risks
Neighborhood: Rosedale
Nearby schools
GreatSchools rating
No schools nearby
We couldn't find any schools near this home.






