106 Highland Avenue, Toronto, ON
Rosedale-Moore Park, Toronto · MLS® C13818260
About this home
In short
- There's a certain kind of house that feels made for family life, and 106 Highland Avenue is exactly that.
- Completely renovated in 2015 by architect Peter Higgins, it pairs remarkable craftsmanship with thoughtful, enduring design.
- Upstairs, the private primary suite offers 2 walk-in closets, its own gas fireplace, & a beautifully appointed ensuite with deep soaker tub.
- The L/L is exceptionally functional, with high ceilings & a walkout.
- 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...
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.
Key facts
- Property type
- Semi-Detached, 2 1/2 Storey
- MLS®
- C13818260
- Bedrooms
- 4+1 (5 total)
- Bathrooms
- 5 (1 half)
- Size
- 2500-3000 sq ft
- Lot
- 38.18 × 148.49 ft
- Cross streets
- Highland Ave and Glen Rd
- Parking
- 2 parking
- Driveway
- Private
- Basement
- Finished, Full, Separate Entrance
- Heating
- Forced Air
- A/C
- Central Air
- Exterior
- Brick
- Foundation
- Concrete
- Roof
- Asphalt Shingle
- Sewer
- Sewer
- Property tax
- $16,458 / 2026
- Days on market
- 6
- Listing brokerage
- SOTHEBY'S INTERNATIONAL REALTY CANADA
Rooms
hardwood floor · open concept · overlooks family
hardwood floor · b/i closet · skylight
gas fireplace · walk-in closet(s) · 5 pc ensuite
hardwood floor · above grade window · closet
hardwood floor · french doors · w/o to garden
hardwood floor · centre island · breakfast bar
hardwood floor · above grade window · pot lights
hardwood floor · large closet · closet organizers
hardwood floor · gas fireplace · overlooks frontyard
Listed at $3,750,000. Going by how homes in Rosedale-Moore Park and the wider GTA have actually closed against their asking prices (about 98%, 5 local closings in 90 days), the likely sale price is near $3.67M, if it sells. A realistic range is $3.44M to $4.14M.
Independent value check: $3.59M. Without looking at the asking price, our model values the home itself about 4% below the ask (homes like it typically land between $3.37M and $3.77M).
Why $3.59M. The typical semi-detached home sold in Rosedale-Moore Park over the past year went for about $2.79M (24 sales). What sets this one apart:
- ▲ Raises it stronglyIts tax bill, which follows the city's own assessment, is $16,458 a year; the typical home sold here pays about $14,100.
- ▲ Raises it4+1 bedrooms and 5 baths, against 3+1 and 4 typically.
- ▲ Raises itIt is 2,500 to 3,000 sq ft; the typical home sold here is 2,000 to 2,500.
- ▲ Raises it slightlyThe listing describes it as fully renovated or newly built.
Total price vs nearby homes. Likely closing about $3.67M, from 5 recent closings in this pocket.
The market behind the math:
About 3.6 months of inventory: 6 semi-detached homes for sale in the area against 5 closings in the last 90 days. Under two months favours sellers, over four favours buyers.
Price per square foot: this home lists at $1,364/sqft against an area asking average of $1,326/sqft.
- Separate-entrance basement apartment features. A finished 1 bed basement apartment with a separate entrance. A self-contained space for extended family, guests or potential income. In Rosedale-Moore Park basements rarely rent out (2 of 11 recent detached leases were basement units), so buyers here treat a suite as family or nanny space rather than income. Value it for the living space, not the rent. Second-suite retrofit status is not verified. A buyer intending to rent should confirm requirements with the City of Toronto.
- Ravine / green setting. This home is described as backing onto a ravine or green setting. A premium that comparable-sales math under-prices, so read the estimate as a floor.
How this estimate is builtthe short version
This figure comes from a model built on about 44,000 recent GTA sales. It weighs this home’s tax assessment, size, age, location and features against what homes like it actually sold for, including sales in this neighbourhood.
It never sees the asking price. The 5 most comparable recent sales on their own, adjusted for size, beds, baths and lot, point to about $3.22M. Condition and finishes remain an in-person call.
What the listing highlights5 points to weigh
Claims from the listing, worth confirming in person. I can book you a private showing.
- Ravine lot: privacy and premium value, but confirm the buildable area and any conservation limits. Worth verifying
- Renovated / rebuilt: recent work can mean fewer upfront costs, worth confirming the scope, quality, and that permits were pulled. Value driver
- Upscale kitchen: a genuine value driver, verify the appliances, stone, and finishes in person. Value driver
- Heated floors: comfort and a premium-finish signal. Lifestyle
- Tall ceilings: they transform how a home feels, worth confirming the actual heights room to room. Worth verifying
Schools & getting aroundcatchment and transit
Its public catchment (Whitney Junior Public School) tests around the provincial average, a steady, family-friendly draw. The full EQAO breakdown is below.
Read this with carewhy it’s an estimate, not an appraisal
There were not many closely comparable homes right in Rosedale-Moore Park, so I widened the search to the surrounding area.
Based on 5 comparable homes that sold in Rosedale-Moore Park over the past two years, from 45 closings there.
For sale
For sale
For sale
For sale
For sale
For saleNothing closely matching this home is listed nearby right now, so these are the nearest semi-detached listings on the market. Homes like this one have recently closed around $3.59M, which is where my estimate comes from.
Per square foot, these ask about $1,375/sqft; this home lists at $1,364/sqft. Size is part of the price story, not just the sticker.
The 5 closest of 6 active listings nearby.
See all comparable homesNeighbourhood & location
Rosedale-Moore Park, Toronto, ON
Enter a workplace or destination and we’ll show the door-to-door time by car, transit and bike.
How asking prices compare in the closest areas to this home. Longer bars mean a pricier market.
Typical asking price of active listings of the same type, per area (outliers removed). Toronto.
Get the full neighbourhood report (schools, parks, transit & safety) →
The public and Catholic schools this address is zoned for, with EQAO results (the share of students meeting Ontario's provincial standard).
School attendance boundaries and EQAO results are Ontario government data and can change. Confirm the current catchment with the school board before relying on it.
Also nearby: 12 more schools within 2.5 km
Not the assigned catchment: schools a family here could reach, with EQAO results where published.
Affordability & Mortgage
Income needed assumes a ~32% GDS ratio; weekly is mortgage principal & interest only. Price ÷ income is the home price over the income needed. Fixed reference assumptions so listings compare on equal footing, not a lending decision.
Calculate and customize your mortgage and other expenses
Adjust the down payment, rate, and amortization, and add property tax, condo fees, and heating to see your true monthly cost.
Your numbers
Homes over $1.5M can't be insured, so 20% down or more is required.
Conventional (20%+ down). Best insured 5-year fixed 4.34% via Ratehub.ca (as of September 30, 2026); conventional rates run a little higher.
Mortgage amount $3,000,000 · 4.49% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $16,588
- Property tax
- $1,372
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $17,959
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $80,225
- Toronto municipal land transfer tax
- $87,725
- Estimated closing costs
- $167,950
Plus your down payment of $750,000. Legal fees, title insurance, and adjustments are extra and vary by deal.
Mortgage stress test
Lenders qualify you at the greater of your rate plus 2% or 5.25%. You do not pay this rate. It just shows you could still handle payments if rates rose, so aim to stay comfortable at this higher number.
Over the full 25 years
At the end of your 5-year term
- Total paid over the term
- $995,251
- Principal paid down
- $366,545
- Interest paid
- $628,706
- Balance remaining
- $2,633,455
Talk to Team Asgarian about your options
Rates and programs change often. We will connect you with a trusted mortgage professional and build a plan that fits your budget and goals.
Estimates only, not a mortgage quote or pre-approval. Figures use Canadian semi-annual compounding, current minimum down-payment rules, CMHC premium tiers, and Ontario (plus Toronto, when selected) land transfer tax. Actual rates, taxes, insurance, and closing costs vary by lender and property. Confirm every number with your mortgage professional.
Investor snapshot
About the suite: in Rosedale-Moore Park basements rarely rent out (2 of 11 recent detached leases were basement units), so the figure above does not count it as income. Buyers here use a suite as family or nanny space.
Thinking of this home as an investment? We will pull real comparable rents and run the full numbers with you.
Talk about the numbersThe last 6 whole-home leases in Rosedale-Moore Park signed at a median of $10,500 a month; adjusted to this home for size, beds and baths, and for where rents stood the month each signed, that is $10,338. The gross yield above is on the asking price, before taxes and upkeep; the cap rate is after them. A finished basement or second suite can push real rent above it. Taxes, fees, and vacancy vary by property, and cap rate is before financing.
Helpful resources
All information deemed reliable but not guaranteed. For personal, non-commercial use only. Listing courtesy of SOTHEBY'S INTERNATIONAL REALTY CANADA. MLS®/PropTx.