Proudly Canadian
Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 1 of 38
Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 2 of 38
Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 3 of 38
Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 4 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 5 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 6 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 7 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 8 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 9 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 10 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 11 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 12 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 13 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 14 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 15 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 16 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 17 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 18 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 19 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 20 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 21 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 22 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 23 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 24 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 25 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 26 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 27 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 28 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 29 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 30 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 31 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 32 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 33 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 34 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 35 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 36 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 37 of 38

Unlock All 38 Photos

Enter your email for instant access

Semi-Detached  for sale at 106 Highland Avenue, Toronto C09 - 5 bedroom, 5 bathroom - Photo 38 of 38

Unlock All 38 Photos

Enter your email for instant access

1 / 3835 locked
Active
MLS® C13104898

106 Highland Ave

Toronto C09, ON M4W 2A6

$3,795,000

Bedrooms

5

Bathrooms

5

Size

2500-3000 sqft

Type

2 1/2 Storey

Parking

2 spaces

Age

100+ yrs

Taxes (2025)

$16,175.17

Get Verified Property Details

Know the exact year built and above grade square footage — verified and sent to you within 2 hours.

Free service · No spam · Data verified by our team

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.

Price & Status History

Price history is locked

Property Details

Property TypeSemi-Detached
Style2 1/2 Storey
CommunityRosedale-Moore Park
Approximate Age100+
Rooms8+2
Kitchens1
Washrooms5
Square Feet2500-3000 sqft
Lot Dimensions38.18 × 148.49 ft
Fronting OnNorth
Dir/Cross StHighland/Glen Rd
Garage TypeAttached
DrivePrivate
Parking Drive Spaces2
Total Parking Spaces2
ExteriorBrick
RoofAsphalt Shingle
FoundationStone
BasementFinished
Fireplace FeaturesYes
Heating TypeForced Air
Heating SourceGas
A/CCentral Air
SewersSewer
Taxes (2025)$16,175.17
HSTIncluded In
UFFIRemoved
Listed Date5/8/2026
Days on Market12 days
PossessionTBD
Vick Yogeswaran - REALTOR

Book a Private Showing

Guided by Vick Yogeswaran • REALTOR®

RE/MAX Realtron Realty Inc., Brokerage

15+ years experience in GTA real estate
Private showings arranged quickly
Expert negotiation support
No pressure • 100% free consultation

Get Exclusive Property Insights

Access information not available to the public – no agent pressure, just the facts you need.

Listing Courtesy of:

ROYAL LEPAGE REAL ESTATE SERVICES OXLEY REAL ESTATE

This listing is provided through the TRREB MLS® System.

Same-day showings available across the GTA

MLS® #C13104898

Thinking about living in Toronto?

Explore the neighbourhood guide for Toronto — market trends, popular areas, buyer tips, and more.