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Sep 26, 2026 02:00 PM - 04:00 PM EDT

106 Highland Avenue
Rosedale-Moore Park Toronto M4W 2A6

$3,750,000
Residential Freehold beds: 4+1 baths: 5.0

Main Photo: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 1: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 2: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 3: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 4: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 5: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 6: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 7: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 8: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 9: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 10: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 11: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 12: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 13: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 14: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 15: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 16: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 17: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 18: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 19: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 20: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 21: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 22: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 23: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 24: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 25: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 26: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 27: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 28: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 29: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 30: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 31: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 32: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 33: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 34: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 35: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 36: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 37: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 38: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 39: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 40: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 41: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 42: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 43: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 44: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 45: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 46: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 47: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 48: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Photo 49: 106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13818260
Open House - Sep 26, 2026
02:00 PM - 04:00 PM EDT
NOTES: Open House on Saturday, September 26, 2026 2:00PM - 4:00PM
Open House - Sep 27, 2026
02:00 PM - 04:00 PM EDT
NOTES: Open House on Sunday, September 27, 2026 2:00PM - 4:00PM
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
C13818260
Bedrooms:
4+1
Bathrooms:
5
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 in one of Toronto's most coveted neighbourhoods. 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.
Property Type:
Residential Freehold
Property Sub Type:
Semi-Detached
Home Style:
2 1/2 Storey
Total Approx Floor Area:
3500-5000
Lot Depth:
148'5⅞"
Lot Frontage:
38'2"
Lot Shape:
Irregular
Direction Faces:
North
Bedrooms:
4+1
Bathrooms:
5.0
Water supply:
Municipal
Kitchens:
1
Bedrooms Above Grade:
4
Bedrooms Below Grade:
1
Kitchens Above Grade:
1
Rooms Above Grade:
8
Rooms Below Grade:
2
Heating type:
Forced Air
Heating Fuel:
Gas
Foundation:
Concrete
Roof:
Asphalt Shingle
Basement:
Finished
Fireplace Features:
Natural Gas
Fireplace/Stove:
Yes
Garage:
None
Garage Spaces:
0.0
Parking Features:
Private
Parking Spaces:
2
Total Parking Spaces:
2.0
Family Room:
Yes
Possession Details:
30-90 Days
Lot Irregularities:
See Attached Survey-Irreg,27.55N,122.5W
Pool:
None
HST Applicable To Sale Price:
Included In
Taxes:
$16,458 / 2026
Assessment:
$- / -
Toronto
Toronto C09
Rosedale-Moore Park
Fenced Yard, Park, Public Transit, Rec./Commun.Centre, School, School Bus Route
Bar Fridge, Built-In Oven, Central Vacuum, Countertop Range, ERV/HRV, In-Law Suite, Storage, Sump Pump
Alarm System, Monitored
Reliance Hot Water Tank: $118.13 + HST /month
Wolf 6 Burner Gas Stove; Fisher & Paykel Fridge; Miele: panelled dishwasher, built-in coffee machine, wall oven/microwave; lower level Frigidaire freezer; Whirlpool front load washer & dryer; stackable Miele Washer & Dryer; Perlick wine fridge; All electrical light fixtures; All window coverings; Alarm system with outdoor cameras (monitoring extra); wired ceiling speakers with Sonos System; Backyard irrigation system + wired Bose speakers; Wall mounted TVs.
None
Brick
None
Floor
Type
Size
Other
Main
Living Room
16'8" × 13'7"
Hardwood Floor, Gas Fireplace, Overlooks Frontyard
Main
Dining Room
15'8" × 12'5"
Hardwood Floor, Open Concept, Overlooks Family
Main
Kitchen
51'8" × 29'6"
Hardwood Floor, Centre Island, Breakfast Bar
Main
Family Room
11'4" × 10'8"
Hardwood Floor, French Doors, W/O To Garden
Second
Primary Bedroom
13'3" × 12'
Gas Fireplace, Walk-In Closet(s), 5 Pc Ensuite
Second
-
18'5" × 10'9"
Hardwood Floor, Walk-In Closet(s), 4 Pc Ensuite
Third
Bedroom 3
17'2" × 12'8"
Hardwood Floor, B/I Closet, Skylight
Third
Bedroom 4
16'4" × 11'
Hardwood Floor, Large Closet, Closet Organizers
Lower
Recreation
16'9" × 15'8"
Hardwood Floor, Above Grade Window, Pot Lights
Lower
Bedroom 5
14' × 9'8"
Hardwood Floor, Above Grade Window, Closet
Utilities Cable:
Yes
Utilities Telephone:
Yes
Utilities Gas:
Yes
Utilities Hydro:
Yes
Utilities Water:
Yes
Sewers:
Yes
Special Designation:
Unknown
Sewers:
Sewer
Air Conditioning:
Central Air
Central Vacuum:
Yes
Seller Property Info Statement:
No
Laundry Level:
Lower Level
Date Listed:
Sep 23, 2026
Original Price:
Previous Price:
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Listed by SOTHEBY'S INTERNATIONAL REALTY CANADA
Data was last updated September 23, 2026 at 12:15 PM (UTC)
JARROD  ARMSTRONG
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