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106 Highland Avenue

Rosedale-Moore Park / Toronto C09, ON M4W 2A6

ActiveFor Sale
5 Beds
5 Baths
2,500 Sq Ft
Semi-Detached

About This Property

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. Approximately 4,000 sf (total). 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 Details

StatusActive
Property TypeSemi-Detached
Listing TypeFor Sale
Interior Size2,500 sq ft
Bedrooms5
Bathrooms5
Taxes (2026)$16,458
Postal CodeM4W 2A6
Last UpdatedOct 28, 2026 · 12:30 p.m.

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Features & Amenities

  • Fireplace
  • Air Conditioning
  • Basement

Buying or selling in Toronto?

Filipe & Isabel Ferreira and the Team Filipe (RE/MAX Ultimate Realty Inc., Brokerage) represent buyers and sellers here. Local guides and live listings below.

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TRREB MLS® Attribution

MLS® C14107036

Listed by SOTHEBY'S INTERNATIONAL REALTY CANADA

The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA. The trademarks REALTOR®, REALTORS® and the REALTOR® logo are controlled by CREA and identify real estate professionals who are members of CREA. Listing data provided by the Toronto Regional Real Estate Board (TRREB). The information contained herein is from sources believed to be reliable but is not guaranteed. Information deemed reliable but not guaranteed accurate by TRREB or Team Filipe / RE/MAX.

$3,629,000

asking price

MLS®C14107036
TypeSemi-Detached
CityToronto C09
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Team Filipe · RE/MAX · (647) 210-6070

Mortgage Estimate

Est. Monthly Payment

$17,721

/month · $2,903,200 mortgage

Down Payment20% — $725,800
Interest Rate5.5%

Amortization

Total Interest

$2,413,066

Total Cost

$5,316,266

Estimate only. Based on Canadian semi-annual compounding, 25-yr amortization at 5.5%.

Full Mortgage Calculator →

Listed By

SOTHEBY'S INTERNATIONAL REALTY CANADA