106 Highland Avenue

Rosedale-Moore Park, Toronto, Ontario M4W 2A6

Overview

At a glance

Days on market4 days
ListedOct 22, 2026
UpdatedOct 22, 2026
Building age100+ years
Size2500-3000 sq ft
Lot38.18 x 148.49 Feet
Property taxes$16,458 (2026)
Parking2 spaces
BasementFinished, Full, Separate Entrance
MLS® numberC14107036
Data sourcePropTx MLS® System
Listing brokerageSOTHEBY'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.

Details

Property

Style
2 1/2 Storey
Building age
100+
Fronting on
North
Cross street
Highland Ave and Glen Rd
Community
Rosedale-Moore Park
Municipality
Toronto C09

Inside

Bedrooms above grade
4
Bedrooms below grade
1
Bathrooms
5
Kitchens
1
Basement
Finished, Full, Separate Entrance
Family room
Yes
Fireplace
Natural Gas
Interior features
Bar Fridge, Built-In Oven, Countertop Range, ERV/HRV, In-Law Suite, Storage, Sump Pump, Carpet Free, In-Law Capability

Utilities

Heating
Forced Air
Heating fuel
Gas
Cooling
Central Air
Sewer
Sewer
Electricity
Yes
Cable
Yes

Building

Construction
Brick
Foundation
Concrete
Roof
Asphalt Shingle
Exterior features
Year Round Living, Landscaped
Pool
None

Parking

Garage
None
Parking spaces
2
Total parking
2
Driveway
Private

Land

Frontage
38.18
Depth
148.49
Lot size units
Feet
Lot irregularities
See Attached Survey-Irreg,27.55N,122.5W
Waterfront
No
Property features
Park, Public Transit, Rec./Commun.Centre, School, School Bus Route, Ravine
Rooms (10)
RoomLevelSizeFeatures
Living RoomMain5.08 x 4.14 MetersHardwood Floor, Gas Fireplace, Overlooks Frontyard
Dining RoomMain4.78 x 3.78 MetersHardwood Floor, Open Concept, Overlooks Family
KitchenMain15.75 x 8.99 MetersHardwood Floor, Centre Island, Breakfast Bar
Family RoomMain3.45 x 3.25 MetersHardwood Floor, French Doors, W/O To Garden
Primary BedroomSecond4.04 x 3.66 MetersGas Fireplace, Walk-In Closet(s), 5 Pc Ensuite
RoomSecond5.61 x 3.28 MetersHardwood Floor, Walk-In Closet(s), 4 Pc Ensuite
Bedroom 3Third5.23 x 3.86 MetersHardwood Floor, B/I Closet, Skylight
Bedroom 4Third4.98 x 3.35 MetersHardwood Floor, Large Closet, Closet Organizers
RecreationLower5.11 x 4.78 MetersHardwood Floor, Above Grade Window, Pot Lights
Bedroom 5Lower4.27 x 2.95 MetersHardwood Floor, Above Grade Window, Closet
Value

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History

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Neighbourhood

Around Rosedale-Moore Park

What’s nearby

On a busier streetBackyard faces north

  • Elementary schoolWhitney Junior Public Schoolabout 10 min walk
  • High schoolRosedale Heights School of the Artsabout 15 min walk
  • ParkBeaumont Parkabout 1 min walk
  • Playground about 7 min walk
  • TrailPark Drive Reservation Trailabout 3 min walk
  • River or lakeYellow Creekabout 3 min walk
  • Grocery storeSummerhill Marketabout 8 min walk
  • DowntownTorontoabout 3.2 km
  • LibraryToronto Public Library - Toronto Reference Libraryabout 21 min walk
  • Rec centre or arenaRosedale Tennis Clubabout 6 min walk
  • Golf courseGolf 247about 2.9 km
  • HospitalSunnybrook Holland Centreabout 27 min walk
  • Highway on-ramp about 8 min walk
  • GO or train stationToronto Union Stationabout 4.1 km

Approximate: straight-line distances, and the backyard and street worked out from the map pin and map data © OpenStreetMap contributors. Check school boundaries with the school board.

On the map

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Community

The Rosedale-Moore Park market

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Costs

What it would cost

%
%
An example rate. Use the one your lender quotes.
Every monthEstimate
Mortgage payment$0
Property tax$0
Monthly total$0
At closing
Ontario land transfer tax$0

Estimates only, not financial advice. Uses Canadian semi-annual compounding, the minimum down payment and mortgage insurance rules, and Ontario’s land transfer tax brackets. Your lender and lawyer confirm the real numbers. Legal fees, title insurance and moving costs aren’t included.

Listing courtesy of SOTHEBY'S INTERNATIONAL REALTY CANADA. Listing information from the PropTx MLS® System. Each listing shows the brokerage that represents it. The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate and may not be used for any commercial purpose or any other purpose. Information is deemed reliable but is not guaranteed accurate by PropTx. Last updated October 26, 2026 at 10:38 p.m.

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