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.
About this home
Photos of 106 Highland Avenue
Facts and features of 106 Highland Avenue
| Type | Semi-Detached |
|---|---|
| Style | 2 1/2 Storey |
| Bedrooms | 4 + 1 |
| Bathrooms | 5 |
| Size | 2500-3000 sq ft |
| Lot | 38.18 x 148.49 Feet |
| Parking | 2 |
| Garage | None |
| Heating | Forced Air |
| Cooling | Central Air |
| Basement | Finished, Full, Separate Entrance |
| Exterior | Brick |
| Age | 100+ |
| Taxes | $16,458 (2026) |
| Days on market | 7 |
| Listing brokerage | SOTHEBY'S INTERNATIONAL REALTY CANADA |
Rooms
9 rooms, with sizes
| Room | Level | Size | Features |
|---|---|---|---|
| Living Room | Main | 16′ 8″ × 13′ 7″ 5.08 × 4.14 m | hardwood floor, gas fireplace, overlooks frontyard |
| Recreation | Lower | 16′ 9″ × 15′ 8″ 5.11 × 4.78 m | hardwood floor, above grade window, pot lights |
| Kitchen | Main | 51′ 8″ × 29′ 6″ 15.75 × 8.99 m | hardwood floor, centre island, breakfast bar |
| Bedroom 3 | Third | 17′ 2″ × 12′ 8″ 5.23 × 3.86 m | hardwood floor, b/i closet, skylight |
| Bedroom 5 | Lower | 14′ 0″ × 9′ 8″ 4.27 × 2.95 m | hardwood floor, above grade window, closet |
| Family Room | Main | 11′ 4″ × 10′ 8″ 3.45 × 3.25 m | hardwood floor, french doors, w/o to garden |
| Primary Bedroom | Second | 13′ 3″ × 12′ 0″ 4.04 × 3.66 m | gas fireplace, walk-in closet(s), 5 pc ensuite |
| Dining Room | Main | 15′ 8″ × 12′ 5″ 4.78 × 3.78 m | hardwood floor, open concept, overlooks family |
| Bedroom 4 | Third | 16′ 4″ × 11′ 0″ 4.98 × 3.35 m | hardwood floor, large closet, closet organizers |
Around this home
What’s near 106 Highland Avenue
From 106 Highland Avenue, the nearest station is Castle Frank station (Line 2 Bloor-Danforth), about 950 m away; the nearest grocery store is Summerhill Market, about 600 m away; the nearest TDSB elementary school is Rosedale Junior Public School, about 750 m away; and the nearest park is Beaumont Park, about 200 m away.
Transit
- Castle Frank station Line 2 Bloor-Danforth about 950 m
- Sherbourne station Line 2 Bloor-Danforth about 1.0 km
- Rosedale station Line 1 Yonge-University about 1.3 km
Groceries and pharmacies
- Marshall's Drugs Pharmacy about 550 m
- Summerhill Market Grocery about 600 m
- Bloor-Sherbourne Pharmacy Pharmacy about 1.1 km
- Wan2 supermarket Grocery about 1.1 km
- No Frills Grocery about 1.1 km
Parks
- Beaumont Park Park about 200 m
- Whitney Park Park about 300 m
- Rosedale Park Park about 400 m
Schools
- Rosedale Junior Public School TDSB elementary · JK-6 EQAO 2024-25: Gr 6 reading 100% · Gr 6 math 100% about 750 m
- Whitney Junior Public School TDSB elementary · JK-6 EQAO 2024-25: Gr 6 reading 100% · Gr 6 math 88% about 750 m
- Westwood Middle School TDSB middle school · 6-8 EQAO 2024-25: Gr 6 reading 84% · Gr 6 math 44% about 1.9 km
- Our Lady of Perpetual Help Catholic School Catholic elementary · JK-8 EQAO 2024-25: Gr 6 reading 100% · Gr 6 math 80% about 1000 m
- Rosedale Heights School of the Arts TDSB secondary · 9-12 EQAO 2024-25: Gr 9 math 66% · Gr 10 literacy 95% about 1.0 km
- Msgr Fraser College (Isabella Campus) Catholic secondary · 9-12 about 1.3 km
Nearest schools, not necessarily the ones that serve this address. Check with the TDSB and TCDSB school locators.
Community
- Rosedale-Moore Park Community Association Community centre about 600 m
- Toronto Reference Library Library Library about 1.5 km
- Aquatic Centre Pool or arena about 1.5 km
Private schools
- Girls
- Branksome Hall JK to Grade 12 about 850 m
- The Bishop Strachan School JK to Grade 12 about 3.0 km
- Boys
- Upper Canada College JK to Grade 12 about 2.6 km
- Royal St. George's College Grades 3 to 12 about 3.2 km
- St. Michael's College School Grades 7 to 12 about 3.5 km
- Co-ed
- De La Salle College "Oaklands" Grades 5 to 12 about 1.9 km
- The Rosedale Day School JK to Grade 8 about 2.0 km
- The York School JK to Grade 12 about 2.0 km
- Sunnybrook School JK to Grade 6 about 2.1 km
Within a 40-minute walk, from our list of private schools in central Toronto (checked October 2026). Fees and admissions on each school’s site. See all private schools
Restaurants
- Seoul Food Google reviews about 1.1 km
- Eggstatic Google reviews about 1.1 km
- Sushi Cafe Google reviews about 1.1 km
- Maja Indian Cuisine Google reviews about 1.1 km
- Chae's Chester Fried Chicken Express Google reviews about 1.1 km
Places: OpenStreetMap contributors, October 2026. Straight-line distances. Schools: EQAO 2024-25, Ontario Ministry of Education.
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The neighbourhood
Rosedale
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106 Highland Avenue
Listing information is deemed reliable but is not guaranteed accurate by PropTx or the Toronto Regional Real Estate Board. Data source: PropTx. Listings are refreshed from the MLS® at least daily.
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MLS® C14107036 Data source: PropTx Listed October 22, 2026
