MLS® listing
106 Highland Avenue: semi-detached house for sale
$3,750,000
From the listing brokerage
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.
Facts on the listing
| Square feet | 2500-3000 |
|---|---|
| Approximate age | 100+ |
| Style | 2 1/2 Storey |
| Basement | Finished, Full, Separate Entrance |
| Lot width | 38.18 |
| Lot depth | 148.49 |
| Lot measured in | Feet |
| Faces | North |
| Parking spaces | 2 |
| Garage | None |
| Heating | Forced Air |
| Cooling | Central Air |
| Kitchens | 1 |
| Property tax | $16,458 |
| Tax year | 2026 |
| Parking | Private |
| Interior features | Bar Fridge, Built-In Oven, Countertop Range, ERV/HRV, In-Law Suite, Storage, Sump Pump, Carpet Free, In-Law Capability |
| Features | Park, Public Transit, Rec./Commun.Centre, School, School Bus Route, Ravine |
Listing courtesy of SOTHEBY'S INTERNATIONAL REALTY CANADA. MLS® C13818260.
About this semi-detached house
106 Highland Avenue is a 5 bedroom semi-detached house in TRREB's Rosedale-Moore Park community in Toronto, listed for sale at $3,750,000. The listing shows 5 bathrooms and 2500-3000 square feet. The style is given as 2 1/2 storey. The lot is listed as 38.18 by 148.49 feet. The listing gives the basement as finished, full, separate entrance. It comes with 2 parking spaces according to the listing. The nearest main intersection given is Highland Ave and Glen Rd. The age is listed as 100+ years.
These details come from the listing brokerage through TRREB's MLS® System. Room sizes, the lot, the taxes and what is included in the sale should all be confirmed before an offer is firm.
What it costs to buy 106 Highland Avenue
At the asking price of $3,750,000, a buyer pays two land transfer taxes on closing: the Ontario tax and the City of Toronto's municipal tax. Both apply to every home inside the City.
| Asking price | $3,750,000 |
|---|---|
| Ontario land transfer tax | $80,225 |
| Toronto municipal land transfer tax | $94,475 |
| Both taxes | $174,700 |
| First-time buyer relief, if you qualify | up to $8,475 |
| Minimum down payment | $750,000 |
The down payment figure is the federal minimum: 20 percent, because a home at $1.5 million or more cannot carry mortgage default insurance. A lender can ask for more. These figures use the asking price, so they change if you pay more or less. The rates above $2,000,000 used here are the ones for a home with one or two single family residences. A property with more units is taxed differently. Legal fees, title insurance and adjustments are extra: ask your lawyer for a written quote. This is general information, not legal or tax advice. Confirm the figures with a lawyer or accountant. You can change the price in our land transfer tax calculator and our mortgage calculator.
What it costs to own each month
| Property tax (2026) | $16,458 a year, about $1,372 a month |
|---|
That is before a mortgage payment, home insurance and utilities. The listing shows no monthly maintenance fee, so upkeep of the building and the lot is the owner's own cost.
How the asking price compares
TRREB recorded 159 semi-detached house sales in the City of Toronto in August 2026, at a median price of $981,000 and an average of $1,110,639. This home is listed at $3,750,000, which is $2,769,000 above that median.
The median covers every neighbourhood, size and condition in the City of Toronto, so it is a reference point and not a valuation of this home. Location, size, lot, parking and condition all move the price. Our Toronto house prices page has the figures for every home type.
What to check before you make an offer
- Book a home inspection. An inspector looks at the roof, foundation, wiring, plumbing and heating. The listing gives the heating as forced air.
- Have a lawyer search the title. A title search shows mortgages, liens and easements registered against the property. Ask whether a survey exists and whether it matches the lot on the listing, 38.18 by 148.49 feet.
- Ask about permits. Ask which renovations had building permits and whether those permits were closed.
- Confirm what is included. Appliances, light fixtures and window coverings are included only if the agreement says so. Ask whether the water heater or furnace is rented.
- Get your financing in writing. A lender looks at the property tax and heating costs as well as the price.
- See it in person. The listing has a virtual tour, but photos do not show noise, light at different hours or the state of the street and the homes beside it.
Our first-time home buyer guide and our page for buyers walk through each step. This is general information, not legal advice. Confirm the details with a lawyer.
About Rosedale
Detached houses on winding ravine streets inside two heritage conservation districts, with apartment buildings near Yonge and Bloor. From April to June 2026 the median sale across all property types in Rosedale-Moore Park was $2,425,000 (TRREB).
Transit: Line 1 Yonge University at Rosedale and Summerhill stations, with St Clair station to the north. Line 2 Bloor Danforth at Castle Frank station on Bloor Street East. TTC buses 82 Rosedale, 97 Yonge, 74 Mount Pleasant and 65 Parliament
| Property type | Median | Sales and average |
|---|---|---|
| All property types | Median $2,425,000 | 73 sales, average $2,441,401 |
| Detached | About $3,440,000 | 26 sales, average about $3,981,000 |
| Semi-detached | About $2,725,000 | 11 sales, average about $2,638,000 |
| Condo townhouse | About $1,415,000 | 4 sales, average about $1,661,000 |
| Condo apartment | About $850,000 | 23 sales, average about $1,242,000 |
| Other (TRREB category) | About $779,000 | 8 sales, average about $1,106,000 |
| Freehold townhouse (TRREB att/row/townhouse) | No price reported | 1 sale |
Source: TRREB community housing market reports, as set out in the guide.
Questions about Rosedale
Is Rosedale a good place to live?
That depends on your budget and the type of home you want. TRREB's Rosedale-Moore Park community recorded a detached median of about $3,440,000 from April to June 2026, alongside condo apartments at about $850,000. The area has Rosedale and Summerhill stations on Line 1, Castle Frank station on Line 2 and several City ravine parks.
How much does a house cost in Rosedale?
From April to June 2026 TRREB recorded 26 detached sales in Rosedale-Moore Park with a median of about $3,440,000 and an average of about $3,981,000. The 11 semi-detached sales had a median of about $2,725,000.
Is Rosedale on the subway?
Yes. Rosedale station at 7 Crescent Road and Summerhill station at 16 Shaftesbury Avenue are on Line 1 Yonge University. Castle Frank station at 600 Bloor Street East is on Line 2 Bloor Danforth. Rosedale station is 7 stops from Union station on the TTC map.
Are there condos in Rosedale?
Yes. TRREB recorded 23 condo apartment sales from April to June 2026 with a median of about $850,000 and 4 condo townhouse sales with a median of about $1,415,000. In the 2021 Census 50.2% of private dwellings in Rosedale-Moore Park were in apartment buildings of five or more storeys.
Is Rosedale a heritage conservation district?
Much of it is. The City of Toronto lists two Rosedale heritage conservation districts, South Rosedale and North Rosedale. Exterior changes inside a district follow the district plan, so check whether the exact address falls inside one before you buy.
Read the Rosedale neighbourhood guide · All Rosedale homes for sale
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Questions about 106 Highland Avenue
How much is land transfer tax on 106 Highland Avenue?
At the asking price of $3,750,000 the Ontario tax is $80,225 and the Toronto tax is $94,475, $174,700 in total. A first-time buyer who qualifies can get up to $8,475 back. Confirm the final figures with your lawyer.
What is the minimum down payment for 106 Highland Avenue?
$750,000 at the asking price of $3,750,000, under the federal minimum down payment rules. A lender may require more.
How much is the property tax on 106 Highland Avenue?
The listing shows $16,458 a year for 2026, about $1,372 a month.
Is 106 Highland Avenue priced above or below the median?
It is listed at $3,750,000. The August 2026 median for semi-detached house sales in the City of Toronto was $981,000 across 159 sales, so the asking price is $2,769,000 higher. The median covers all sizes and neighbourhoods.
How do I book a showing for 106 Highland Avenue?
Use the form on this page or call us. Quote MLS® C13818260. We will confirm the listing is still available and arrange a time with the listing brokerage.
Is 106 Highland Avenue still for sale?
This page is refreshed from TRREB's MLS® System through the day. If the listing sells or is withdrawn the page says so. Contact us to confirm before you make plans.
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