106 Highland Avenue

106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
+36
4+1
 bed
5
 bath
2
 parking
2500 - 3000
 sqft
Semi-Detached
$4,495,000
For Sale
46 days
 on site
$4,495,000
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Size
-
Lot size
5669 sqft
Street frontage
-
Possession
Flexible
Price per sqft
$1,498 - $1,798
Taxes
$16,175.17 (2025)
Parking Type
-
Style
2 1/2 Storey
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Description
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.
Broker: ROYAL LEPAGE REAL ESTATE SERVICES OXLEY REAL ESTATE
MLS®#: C12737476
Property details
Parking:
2
Parking type:
-
Property type:
Semi-Detached
Heating type:
Forced Air
Style:
2 1/2 Storey
MLS Size:
2500-3000 sqft
Lot front:
38 Ft
Lot depth:
148 Ft
Listed on:
Jan 28, 2026
Show all details
Rooms
LevelNameSizeFeatures
Second
Primary Bedroom
13.3 x 12.0 ft
Basement
Bedroom
14.0 x 9.7 ft
Basement
Recreation
16.8 x 15.7 ft
Show all
Instant estimate:
orto view instant estimate
$247,214
lower than listed price
i
High
$4,438,464
Mid
$4,247,786
Low
$4,067,619
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About 106 Highland Avenue

106 Highland Avenue is a Toronto semi detached house for sale. It has been listed at $4495000 since January 2026. This 2500-3000 sqft semi detached house has 4+1 beds and 5 bathrooms. 106 Highland Avenue, Toronto is situated in Rosedale, with nearby neighbourhoods in Moore Park, Bennington Heights, St. James Town and Yonge and Bloor.

For those that love cooking, Summerhill Food Market is a 5-minute walk.

Transit riders take note, 106 Highland Ave, Toronto is only steps away to the closest public transit Bus Stop (Highland Ave at Glen Rd) with route Sherbourne, and route Rosedale. Residents of 106 Highland Ave also have decent access to Don Valley Parkway, which is within a few minutes drive