106 Highland Avenue, Toronto, ON

Toronto, Central Toronto, Rosedale-Moore Park Hood
Highland Ave and Glen Rd
4+1 Br | 5 Bath | 2500-3000 Sqft
$3,750,000 For Sale

Property Overview

  • Semi-Detached — 2 1/2 Storey
  • SqFt: | 2500-3000 Sqft
  • Lot Size: 38.18 x 148.49 Feet
  • Age: 100+ Years
  • Basement: Finished, Full, Separate Entrance
  • Exterior: Brick
  • Taxes: 16,458 / 2026
  • Zoning: n/a
  • MLS #: C13818260
  • Sewer: Sewer
  • Heat Source: Gas , Forced Air

Property Description

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.

Wolf 6 Burner Gas Stove; Fisher & Paykel Fridge; Miele: panelled 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.

Property Details

  • For: For Sale
  • Type: Semi-Detached
  • Style: 2 1/2 Storey
  • Lot: 38.18 x 148.49 Feet
  • Region: Toronto
  • Hood: Rosedale-Moore Park
  • Zoning: n/a
  • Lot Irreg: See Attached Survey-Irreg,27.55N,122.5W
  • Fronting On: North

Building Details

  • Age: 100+ Years
  • Exterior: Brick
  • Heat: Gas , Forced Air
  • A/C: Central Air
  • Interior Features: Bar Fridge, Built-In Oven, Countertop Range, ERV/HRV, In-Law Suite, Storage, Sump Pump, Carpet Free, In-Law Capability
  • Pool: None
  • Sewer: Sewer
  • Garage: None
  • Total Parking: 2.00
  • Driveway: Private

Property Interior

  • Sqft: 2500-3000 Sqft
  • Bed: 4 +1
  • Bath: 5
  • Kitchen: 1
  • Family Room: No
  • Basement: Finished, Full, Separate Entrance
Rooms Details

Living Room

Main Level

5.08 x 4.14

Hardwood Floor, Gas Fireplace, Overlooks Frontyard

Dining Room

Main Level

4.78 x 3.78

Hardwood Floor, Open Concept, Overlooks Family

Kitchen

Main Level

15.75 x 8.99

Hardwood Floor, Centre Island, Breakfast Bar

Family Room

Main Level

3.45 x 3.25

Hardwood Floor, French Doors, W/O To Garden

Primary Bedroom

Second Level

4.04 x 3.66

Gas Fireplace, Walk-In Closet(s), 5 Pc Ensuite

Second Level

5.61 x 3.28

Hardwood Floor, Walk-In Closet(s), 4 Pc Ensuite

Bedroom 3

Third Level

5.23 x 3.86

Hardwood Floor, B/I Closet, Skylight

Bedroom 4

Third Level

4.98 x 3.35

Hardwood Floor, Large Closet, Closet Organizers

Recreation

Lower Level

5.11 x 4.78

Hardwood Floor, Above Grade Window, Pot Lights

Bedroom 5

Lower Level

4.27 x 2.95

Hardwood Floor, Above Grade Window, Closet

Property Listed by: SOTHEBY'S INTERNATIONAL REALTY CANADA
Virtual Tour: https://www.dropbox.com/scl/fo/xvxe7jr50nwtgrv09r42l/ANnK1C2PSOhK6U_WT79XNrI?dl=0&e=1&preview=v2_Reel_106HighlandAve.mov&rlkey=01siuplxvoo1o4hp3dzvozd8r&st=kl1o2cxo

Home Valuation Estimate

What is 106 Highland Avenue, Toronto, ON worth in today’s Rosedale-Moore Park, Central Toronto market?

This HomeZira valuation preview helps buyers and sellers think through the asking price for this 4-bedroom Semi-Detached with 2500-3000 sq. ft. in Rosedale-Moore Park, Central Toronto. The full estimate reviews the property’s location, home type, bedroom count, size range, age, and nearby comparable market activity after sign-in.

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Location

  • Address: 106 Highland Avenue
  • Neighborhood: Rosedale-Moore Park
  • Zip/Postal Code: M4W 2A6
  • Nearby Amenities: Park, Public Transit, Rec./Commun.Centre, School, School Bus Route, Ravine
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About 106 Highland Avenue, Toronto, ON M4W 2A6, Central Toronto

Located at 106 Highland Avenue, Toronto, ON in Central Toronto (Rosedale-Moore Park neighbourhood), near Highland Ave and Glen Rd. This freehold home offers Semi-Detached, ["2 1\/2 Storey"], 4 bedrooms, 5 bathrooms and 2500-3000 sq.ft. (approx.) in a layout suited to everyday family living. Basement: Finished, Full, Separate Entrance • 2 parking spots • Garage: None • Heating: Gas Forced Air • Cooling: Central Air. Property taxes are approximately $16,458 for 2026. 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 t.

FAQs for 106 Highland Avenue, Toronto, ON , Rosedale-Moore Park , Central Toronto

What are the listing details for 106 Highland Avenue, Toronto, ON?
106 Highland Avenue, Toronto, ON is a Semi-Detached for sale in Central Toronto, in the Rosedale-Moore Park neighbourhood, Toronto. The current list price is $3,750,000. MLS number: C13818260.
How many bedrooms and bathrooms does this home have?
106 Highland Avenue, Toronto, ON is listed as a Semi-Detached with a ["2 1\/2 Storey"] style, featuring 4+1 bedroom(s) and 5 bathroom(s). The listed interior size range is 2500-3000 sq. ft..
What lot, basement, garage, or parking details are listed?
The lot size is listed as approximately 38.18 x 148.49 Feet. The basement is listed as: Finished, Full, Separate Entrance. Garage type: None. Total parking: 2 space(s).
What heating, cooling, and exterior details are shown?
Heating is listed as: Gas, Forced Air. Cooling is listed as: Central Air. Exterior/construction materials are listed as: Brick.
Where is this property located?
106 Highland Avenue, Toronto, ON is located in the Rosedale-Moore Park neighbourhood of Central Toronto. The listed cross street is Highland Ave and Glen Rd.
What information is available on this public listing page?
The public listing page shows current active listing information, property photos, room details when available, map location, listed price, property features, and contact options. Annual taxes are listed as $16,458 / 2026. Valuation tools and similar sold-property previews are available after sign-in where applicable, without displaying sold data in this public FAQ.

FAQ content is based on current active listing fields shown on this page. Sold prices, sold comparables, and VOW-only details are not included in this public FAQ.