106 Highland Avenue • Toronto, ON photo 1
106 Highland Avenue • Toronto, ON photo 2
106 Highland Avenue • Toronto, ON photo 3
106 Highland Avenue • Toronto, ON photo 4
106 Highland Avenue • Toronto, ON photo 5
106 Highland Avenue • Toronto, ON photo 6
106 Highland Avenue • Toronto, ON photo 7
106 Highland Avenue • Toronto, ON photo 8
106 Highland Avenue • Toronto, ON photo 9
106 Highland Avenue • Toronto, ON photo 10
106 Highland Avenue • Toronto, ON photo 11
106 Highland Avenue • Toronto, ON photo 12
106 Highland Avenue • Toronto, ON photo 13
106 Highland Avenue • Toronto, ON photo 14
106 Highland Avenue • Toronto, ON photo 15
106 Highland Avenue • Toronto, ON photo 16
106 Highland Avenue • Toronto, ON photo 17
106 Highland Avenue • Toronto, ON photo 18
106 Highland Avenue • Toronto, ON photo 19
106 Highland Avenue • Toronto, ON photo 20
106 Highland Avenue • Toronto, ON photo 21
106 Highland Avenue • Toronto, ON photo 22
106 Highland Avenue • Toronto, ON photo 23
106 Highland Avenue • Toronto, ON photo 24
106 Highland Avenue • Toronto, ON photo 25
106 Highland Avenue • Toronto, ON photo 26
106 Highland Avenue • Toronto, ON photo 27
106 Highland Avenue • Toronto, ON photo 28
106 Highland Avenue • Toronto, ON photo 29
106 Highland Avenue • Toronto, ON photo 30
106 Highland Avenue • Toronto, ON photo 31
106 Highland Avenue • Toronto, ON photo 32
106 Highland Avenue • Toronto, ON photo 33
106 Highland Avenue • Toronto, ON photo 34
106 Highland Avenue • Toronto, ON photo 35
106 Highland Avenue • Toronto, ON photo 36
106 Highland Avenue • Toronto, ON photo 37
106 Highland Avenue • Toronto, ON photo 38
106 Highland Avenue • Toronto, ON photo 39
1 / 39
$3,795,000
106 Highland Avenue • Toronto, ONNew
Courtesy of ROYAL LEPAGE REAL ESTATE SERVICES OXLEY REAL ESTATE
4+1
Bedrooms
5
Bathrooms
2500-3000
Square feet
2
Parking

About this home

Welcome to 106 Highland Ave, a gorgeous Red Brick Home w/ incredible curb appeal, impressively set back on an irreg. wide ~39' & ~150' lot ideally situated in prime North Rosedale on one of the most coveted tree-lined streets in the area. Completely renovated in 2015 by Architect Peter Higgins w/ superior quality construction thru/out & timeless design savvy finishes, this extraordinary home is "move in ready" w/ the quality of the home immediately evident as you enter the inviting entrance w/ heated floors & design savvy fluted wood wall which sets the tone for the rest of the home. The open concept main floor greets you with streaming light from front to back & the front sitting rm/great rm features an open flame gas fireplace - the perfect place to start & end your day. The heart of the main floor is the chef inspired custom kitchen w/ bespoke millwork & an oversized island which seamlessly flows into the lg dining area, ideal for everyday living & hosting parties of 12+. The cozy family rm French Doors open to the back deck o/looking the generous backyard. Bask in the generous Primary retreat on the 2nd fl w/ gas f/pl & incredible built-ins as well as 2 walk-in closets. The primary ensuite is truly an escape w/luxurious designer wallpaper, indulgent soaker tub, & twinkling chandelier floating. A 2nd generously sized bedrm also enjoys the convenience of a private ensuite & walk-in closet. 2 additional bedrms, a well-appointed bathrm, & extra laundry rm make up the spacious 3rd floor. Downstairs the lwr lvl has incredible ceiling height thru/out & heated floors in the coveted mudrm easily accessible via the walk out to the side of the house. The massive rec rm is the perfect place for kids to play, watch TV or simply hang out. The long driveway comfortably parks up to 3 cars. Enjoy your private grg offering ample storage for bikes, strollers & more. Steps to Rosedale & Chorley Parks & ravines, Branksome Hall, Whitney P.S., Summerhill Market, & the TTC.

Property details

Property type
Semi-Detached
Style
2 1/2 Storey
Approx. age (yrs)
100+
Total rooms
8
Lot size
38.18 × 148.49 ft
Property taxes
$16,175.17 (2025)
Occupancy
TBD
Days on market
75
Status
Active
MLS®

Property history

Recently sold nearby

Listing data last updated: Jul 9, 2026, 10:10 a.m. EDT via TRREB IDX.

First listed: May 8, 2026, 3:55 p.m. EDT.