106 Highland Avenue, Toronto, ON M4W 2A6

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.

Home details

Days on market

Not reported

Property type

Semi-Detached

MLS® number

C14107036

Source status

New

Bedrooms

5

Bathrooms

5

Postal code

M4W 2A6

Kitchens

1

Kitchens above grade

1

Family room / den

Yes

Interior size (reported range)

2500-3000 (units not reported)

Lot depth

148.49 ft

Garage parking spaces

Not reported

Total parking spaces

2

Occupancy

Owner

Possession type

30-59 days

Garage

None

Annual property tax

16458

Basement

Finished, Full, Separate Entrance

Interior features

Bar Fridge, Built-In Oven, Countertop Range, ERV/HRV, In-Law Suite, Storage, Sump Pump, Carpet Free, In-Law Capability

Exterior features

Year Round Living, Landscaped

Architectural style

2 1/2 Storey

Parking features

Private

Pool features

None

Fireplace

Yes

Waterfront

No

Garage available

No

Heating system

Forced Air

Heating fuel

Gas

Cooling

Central Air

Sewer

Sewer

Direction facing

North

Construction materials

Brick

Roof

Asphalt Shingle

Foundation

Concrete

MLS entry age (not confirmed DOM)

13 days

These details come from the listing source. Please confirm measurements and fees before making a decision.

Utilities and services

Sewer

Sewer

Heating system

Forced Air

Heating fuel

Gas

Cooling

Central Air

A reported service is not necessarily included in rent or maintenance. Missing information does not mean a service is absent.

Room sizes

Bedrooms above grade

4

Bedrooms below grade

1

Rooms above grade

8

Rooms below grade

2

Den / family room reported

Yes

Room counts and measured room dimensions are separate source fields. No measurements are inferred.

Price history

Asking amount

$3,629,000

1. Oct 22, 2026

   Original MLS entry

   Entry into the source MLS system; distinct from days on market.

This history uses dates and prices supplied by the listing source. Some details may be missing.

Estimate monthly costs

Adjust the assumptions for your own scenario. Blank expenses are unknown; enter them for a fuller estimate.

Planning estimate with Canadian semiannual compounding. Excludes mortgage insurance, closing costs and special assessments. This is not a lender quote or mortgage approval.

Map and neighbourhood

Region / county

Toronto

Municipality

TORONTO

MLS® community

Rosedale-Moore Park

MLS® district

Toronto C09