106 Highland Avenue
Toronto C09, ON
- 5 bed
- 5 bath
- approx. 2500-3000 sqft
- Semi-Detached
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.
Listing Details
- Taxes (2026)
- $16,458
- Listed
- October 22, 2026
Price History
Listing history
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Property
- Style
- 2 1/2 Storey
- Age
- 100+
- Construction
- Brick
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Interior
- Bar Fridge, Built-In Oven, Countertop Range, ERV/HRV, In-Law Suite, Storage, Sump Pump, Carpet Free, In-Law Capability
- Lot Size
- 38.18 x 148.49 Feet
Parking
- Garage
- None
- Covered Spaces
- 0
- Total Parking
- 2
Utilities
- Sewer
- Sewer
- Heat Source
- Gas
Location & Legal
- Cross Street
- Highland Ave and Glen Rd
- Parcel Number
- 211160140
- Possession
- 30-59 days
- Occupancy
- Owner
Included
- Inclusions
- Wolf 6 Burner Gas Stove; Fisher & Paykel Fridge; Miele: paneled dishwasher, built-in coffee machine, wall oven/microwave; Whirlpool front load washer & dryer; stackable Miele Washer & Dryer; Perlick wine fridge; All electrical light fixtures; All window coverings; Alarm system with 4 outdoor cameras (monitoring extra); wired ceiling speakers with Sonos System; Backyard irrigation system + wired Bose speakers.
- Exclusions
- All televisions (main level, primary bedroom, third floor bedroom, lower level rec room, lower level bedroom), freezer in lower level
- Rental Items
- Reliance Hot Water Tank: $118.13 + HST /month
Schools
Elementary
- Rosedale Junior Public School0.7 km
Public · Toronto DSB · 220 students
Grade 3 reading: 95% met the provincial standard · Grade 6 math: 100% met the provincial standard
- Whitney Junior Public School0.7 km
Public · Toronto DSB · 420 students
Grade 3 reading: 93% met the provincial standard · Grade 6 math: 88% met the provincial standard
- Our Lady of Perpetual Help Catholic School1 km
Catholic · Toronto CDSB · 330 students
Grade 3 reading: 90% met the provincial standard · Grade 6 math: 80% met the provincial standard
Secondary
- Rosedale Heights School of the Arts1 km
Public · Toronto DSB · 945 students
Grade 10 literacy: 95% met the provincial standard
- Msgr Fraser College (Isabella Campus)1.3 km
Catholic · Toronto CDSB · 345 students
- CALC Secondary School1.3 km
Public · Toronto DSB · 565 students
Straight-line distance. Nearby schools are not necessarily the assigned schools — confirm catchment with the school board. Scores are EQAO provincial test results for 2024-2025.
Community
Postal area M4W
- Population
- 15,296
- Private dwellings
- 9,238
- Median age
- 44.8
- Average household size
- 1.9
- Median household income
- $104,000
Source: Statistics Canada, 2021 Census of Population, catalogue 98-401-X2021013. Adapted from Statistics Canada. This does not constitute an endorsement by Statistics Canada of this product.
Local market
Residential Freehold in Toronto C09 · last 12 months
- Median sold price
- $1,995,000
- Homes sold
- 247
- Median days on market
- 22
- Sale-to-list price
- 96.3%
Based on 247 recorded sales of residential freehold properties in Toronto C09 over the last 12 months.
Rooms
2-piece on Main, 4-piece on Second, 5-piece on Second, 3-piece on Third, 3-piece on Basement
Third
- Bedroom 317'2" x 12'8"
- Bedroom 416'4" x 11'
Second
- Primary Bedroom13'3" x 12'
Main
- Dining Room15'8" x 12'5"
- Family Room11'4" x 10'8"
- Kitchen
- Living Room16'8" x 13'7"
Lower
- Bedroom 514' x 9'8"
- Recreation16'9" x 15'8"
Listed by
SOTHEBY'S INTERNATIONAL REALTY CANADA
Walk Score
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Location
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Mortgage Calculator
$725,800
Estimated Monthly Payment
$17,828
Land transfer tax
Ontario land transfer tax only. An estimate — not legal or financial advice. Municipal land transfer tax applies in Toronto and is not included.
Investment Analysis
No recent nearby lease data. Enter a rent to see the numbers.
Mortgage: $17,828/mo (20% down, 5.5%)
Taxes: $1,372/mo · Insurance: $907/mo
Estimates only. Consult a financial advisor.
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