106 Highland Avenue, Toronto C09

$3,750,000
106 Highland Avenue

$3,750,000

New
30d
Semi-Detached 2 1/2 Storey

106 Highland Avenue, Toronto C09

Total Monthly Obligation $16,873

Beds
5
Baths
5
Park
2
Sqft
2500-3000
DOM
30d
Score
15
Yield
3.2%
Cash on Cash
-8.9%
Cap Rate
2.7%
5Y IRR
8.6%
10Y IRR
9.1%
Property Type-Semi-Detached
MLS® Number-C13818260
Beds-5
Bathrooms-5
Size-2500-3000 sqft
Lot Size-38.18 × 148.49 ft
Listed on site-Sep 23, 2026
Style-2 1/2 Storey
Building Type-Semi-Detached
Age-100+
Taxes-$16,458 (2026)
Parking-2 - None
Basement-Finished, Full, Separate Entrance
Heating-Forced Air (Gas)
Brokerage-SOTHEBY'S INTERNATIONAL REALTY CANADA
Cooling-Central Air
Laundry-No
Fireplace-Natural Gas
Pool-None
Facing-North
Exterior-Brick
Roof-Asphalt Shingle
Foundation-Concrete
Sewer-Sewer
Possession-30-90 Days
Neighbourhood-Rosedale-Moore Park
Title-Residential Freehold

No agent assigned

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.

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Closing Costs

Mortgage Amount
$3,000,000
Land Transfer Taxes$80,225
Legal Fees (Est.)
$
Total cash required for closing$831,725

Total Monthly Obligation

$16,873/mo
Mortgage $15,126
Monthly Loss $12,892
Principal$3,981
Interest$11,146
Property Tax$1,372
Home Insurance$125
Variable Costs$250
Returns
Weight: 25%
Cap Rate
2.4%14
Cash-on-Cash
-11.5%0
5-Year IRR
6.5%16
10-Year IRR
7.8%
Returns Index
9.4/ 100
Growth Sentiment
Weight: 20%
%/yr
Score+50
%/yr
Score+50
%
%
Growth Index
50.0/ 100
GradeD
15/ 100
Avoid•Pass

Strategy: Buy & Hold — Weights: CFI 35% · RI 25%
RKI 20% · GI 20%

Assumptions & Inputs
$/mo
%
$
yr
%
Cash Flow
Weight: 35%
Gross Rent
$121,800/yr
NOI
$88,662/yr
Net Cash Flow
-$7,738/mo
Cash Margin
-76.2%0
Cash Flow Index
0.0/ 100
Risk Profile
Weight: 20%
DSCR
0.495
LTV Ratio
80.0%18
Vacancy Buffer
0.6 mo13
Risk Index
11.8/ 100

*This analysis is independently generated NOT provided by TREB or CREA.

Comparables

Properties near 106 Highland Avenue

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