355 Parkside Drive, Toronto, ON
High Park-Swansea, Toronto · MLS® W13768692
About this home
In short
- Offered for the first time in over 50 years, this impeccably maintained triplex occupies one of Toronto's most coveted corners, proudly positioned at Parkside Drive...
- Spanning three story's, the building comprises two spacious 1,233 sq. ft. two-bedroom suites and a bright 708 sq. ft. one-bedroom suite on the third floor.
- Below, the full unfinished basement features solid concrete construction, dedicated storage rooms, a laundry area, and a powder room, presenting exciting...
- A private driveway accommodates 4 vehicles in addition to a detached garage-an extraordinary convenience in this sought-after neighbourhood.
- Steps to High Park, the subway, the waterfront, and the vibrant boutiques, cafés, restaurants, and pubs of Roncesvalles Village and Bloor West, this is a truly...
Offered for the first time in over 50 years, this impeccably maintained triplex occupies one of Toronto's most coveted corners, proudly positioned at Parkside Drive and Geoffrey Street directly across from High Park. A rare legacy property, lovingly cared for by the same family for half a century, it presents an exceptional opportunity for investors, multi-generational families, or those seeking a premier owner-occupied residence with substantial income potential. Spanning three story's, the building comprises two spacious 1,233 sq. ft. two-bedroom suites and a bright 708 sq. ft. one-bedroom suite on the third floor. West-facing windows in every unit frame picturesque views of High Park's expansive green canopy, creating a tranquil setting rarely found in the city. The property has benefited from significant capital improvements, including updated roof, windows, doors, eavestroughs, fascia, and electrical service, providing peace of mind for years to come. The vacant third-floor suite offers immediate occupancy or market-rent potential, while the first and second floor suites are occupied by outstanding long-term month-to-month tenants who have cared for their homes with pride and respect. Below, the full unfinished basement features solid concrete construction, dedicated storage rooms, a laundry area, and a powder room, presenting exciting possibilities for additional living space, supplementary income suites, or enhanced amenities. A private driveway accommodates 4 vehicles in addition to a detached garage-an extraordinary convenience in this sought-after neighbourhood. Steps to High Park, the subway, the waterfront, and the vibrant boutiques, cafés, restaurants, and pubs of Roncesvalles Village and Bloor West, this is a truly irreplaceable location. Opportunities to acquire a meticulously maintained, generational triplex overlooking Toronto's most celebrated park are exceptionally rare.
Key facts
- Property type
- Other, 2 1/2 Storey
- MLS®
- W13768692
- Bedrooms
- 5
- Bathrooms
- 4 (1 half)
- Size
- 3000-3500 sq ft
- Lot
- 39.73 × 74.05 ft
- Cross streets
- Parkside Drive & Bloor Street W
- Parking
- 1 garage · 5 parking (detached)
- Driveway
- Private
- Basement
- Full, Unfinished, Development Potential
- Heating
- Radiant
- A/C
- None
- Exterior
- Brick
- Foundation
- Block, Stone
- Roof
- Asphalt Shingle
- Sewer
- Sewer
- Property tax
- $9,576 / 2025
- Days on market
- 40
- Listing brokerage
- CORCORAN HORIZON REALTY
Rooms
hardwood floor · window · closet
hardwood floor · window · closet
hardwood floor · bow window
hardwood floor · window · closet
Window
updated · window
hardwood floor · bow window
hardwood floor · bow window
hardwood floor · window · walk-in closet(s)
hardwood floor · bow window · fireplace
hardwood floor · window · closet
updated · window
hardwood floor · window · walk-in closet(s)
No automatic estimate is shown here: there are not enough closely comparable recent sales nearby to support one.
Considering this property? Request a written price readIts public catchment (Howard Junior Public School) tests around the provincial average, a steady, family-friendly draw. The full EQAO breakdown is below.
Neighbourhood & location
High Park-Swansea, Toronto, ON
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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 October 20, 2026); conventional rates run a little higher.
Mortgage amount $1,439,200 · 4.49% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $7,958
- Property tax
- $798
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $8,756
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $32,455
- Toronto municipal land transfer tax
- $32,455
- Estimated closing costs
- $64,910
Plus your down payment of $359,800. 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
- $477,455
- Principal paid down
- $175,844
- Interest paid
- $301,611
- Balance remaining
- $1,263,356
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
Thinking of this home as an investment? We will pull real comparable rents and run the full numbers with you.
Talk about the numbersEstimates only. Rent is modelled on above-grade size and local norms, so a finished basement or second suite (a separate entrance often means one) can push real rent well above this. Taxes, fees, and vacancy vary by property, and cap rate is before financing. A starting point, not a final number, let us run the real ones with you.
Helpful resources
All information deemed reliable but not guaranteed. For personal, non-commercial use only. Listing courtesy of CORCORAN HORIZON REALTY. MLS®/PropTx.