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. Listing data provided by the Toronto Regional Real Estate Board (TRREB). Data is deemed reliable but not guaranteed.
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
Listing
MLS® number
C14107036
Status
For Sale
Listed
Oct 22, 2026
Last updated
Oct 29, 2026
Possession
30-59 days
Building
Type
Semi-Detached
Style
2 1/2 Storey
Approx. age
100+
Approx. size
2,500–3,000 ft²
Basement
Finished, Full, Separate Entrance
Lot
Frontage
38.18 ft
Depth
148.49 ft
Lot area
≈ 5,669 ft² (calculated)
View
North
Community
Rosedale-Moore Park
Parking & utilities
Garage
None, 0 spaces
Driveway
Private, 2 spaces
Heating
Forced Air
Cooling
Central Air
Water / sewer
Not provided by brokerage
Taxes
Property tax
$16,458 / 2026
Condo fee
N/A
Source
Data source
TRREB (VOW feed)
Listed by
SOTHEBY'S INTERNATIONAL REALTY CANADA
Interior
Level
Room
Size
Features
Loading rooms…
Interior Features
Bedrooms above grade: 4
Bedrooms below grade: 1
Kitchens: 1 above grade
Basement: Finished, Full, Separate Entrance
Heating: Forced Air
Cooling: Central Air
Fireplace: Yes
Fireplaces: 2
Exterior
Waterfront features: None
Pool features: None
Property features: Park, Public Transit, Rec./Commun.Centre, School, School Bus Route, Ravine
Demographic data is not available for this area yet.
Population—
Median household income—
Median age—
Age Groups
Age group data is not available.
Owners vs Renters
Ownership data is not available.
Household Type
Household data is not available.
What’s NearbyDistances approximate
No nearby school data is available for this listing.
Transit score information is not available for this listing.
Nearby everyday places are not available for this listing.
Always confirm school catchments with the local school board.
Estimated Rental Income
Rental estimate coming soon
We’re not showing a number until we have a data source we trust. When it’s connected, this section will show:
A monthly rent range from nearby leased homes of the same type and size
The leased comparables behind it (signed-in, VOW-gated)
Gross yield at the current list price
Monthly Cost
A quick estimate to plan with. Taxes come from the listing; change the other inputs to match your situation.
Estimated monthly$14,947/mo
Mortgage (principal + interest)$13,576
Property taxFrom listing: $16,458/yr$1,372
Minimum 20% ($725,800 on this price) applies to homes priced over $1.5M in Canada; the slider starts at 20%. Confirm with a lender.
Mortgage uses Canadian semi-annual compounding. Houses-Gate doesn’t offer financing.
Estimated Budget
About how much cash you’ll need on closing day, besides the mortgage.
Down payment20% of the list price$725,800
Ontario land transfer taxProvincial brackets, no first-time refund$77,200
Toronto land transfer taxMunicipal brackets, no first-time refund$89,151
Legal fees & disbursementsTypical range $1,800–$2,800$1,800
Home inspectionTypical range $500–$800$600
Title insuranceTypical range $300–$600$400
Cash needed at closingEstimate$894,951
First-time buyers can get up to $4,000 back on Ontario land transfer tax. Toronto adds its own land transfer tax; first-time buyers can get up to $4,475 back on it.
Uses Ontario’s land transfer tax brackets and the down payment set in Monthly Cost. Legal, inspection and title-insurance figures are typical ranges, not quotes.
Listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The data is deemed reliable but is not guaranteed to be accurate. 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 information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate and may not be used for any commercial purpose or any other purpose.
All information deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither listing broker(s) nor HousesGate shall be responsible for any typographical errors, misinformation, misprints, and shall be held totally harmless.
