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$4,295,000

106 Highland Ave

Toronto C09, ON M4W 2A6

106 Highland Ave, Toronto C09 — Listed at $4,295,000. 5 bedroom, 5 bathroom 2 1/2 Storey Semi-Detached. MLS® C12960708.

5Beds
5Baths
2500-3000sqft
Semi-Detached
2 1/2 Storey
2Parking
$16,175.17Taxes/yr · 2025
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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.

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 Date4/6/2026
Days on Market220 days
PossessionTBD

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Listing Courtesy of: ROYAL LEPAGE REAL ESTATE SERVICES OXLEY REAL ESTATE

MLS® #C12960708

TRREBMLS®

The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The listing data is deemed reliable but is not guaranteed accurate by TRREB. The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.

© 2026 Toronto Regional Real Estate Board. All rights reserved.

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HouseIndex Take: 106 Highland Avenue

This semi-detached (2 1/2 Storey) is located in the Rosedale-Moore Park neighbourhood of Toronto.

The home offers 5+1 bedrooms, 5 bathrooms.

Features include a finished basement, 2 parking spaces, a fireplace.

Additional details: lot dimensions of 38.18 × 148.49 feet.

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About Toronto Real Estate

This Semi-Detached is located in the Rosedale-Moore Park community in Toronto. Toronto is Canada's largest city and the economic hub of the Greater Toronto Area. With world-class transit, diverse neighbourhoods from the Annex to Scarborough, and proximity to major employers in the Financial District, it remains the most sought-after real estate market in Ontario. Buyers benefit from extensive GO Transit and TTC subway connectivity. Semi-detached homes in Toronto provide freehold ownership at a more accessible price point, appealing to first-time buyers and young families.

TTC subway & streetcar networkWorld-class dining & entertainmentUniversity of Toronto & major hospitals nearbyWaterfront trails & ravine parks
Walkability: Highly walkable — many neighbourhoods score 80+ on Walk Score
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