355 Parkside Drive, Toronto, ON
High Park-Swansea, Toronto · MLS® W13487692
About this home
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 storeys, 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®
- W13487692
- Bedrooms
- 5
- Bathrooms
- 4 (1 half)
- Size
- 3000-3500
- 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
- 28
- Listing brokerage
- CORCORAN HORIZON REALTY
Rooms
Window
hardwood floor · window · closet
updated · window
updated · window
hardwood floor · window · closet
hardwood floor · bow window
hardwood floor · bow window
hardwood floor · bow window
hardwood floor · window · walk-in closet(s)
hardwood floor · window · closet
hardwood floor · window · walk-in closet(s)
hardwood floor · bow window · fireplace
hardwood floor · window · closet
Listed at $1,829,000, and my independent estimate is within the range of comparable homes, on the lower side.
In High Park-Swansea lately, sellers get about 104% of asking; homes sell in ~16 days.
Total price vs nearby homes. Fair value about $2.31M, median of 18 comparables.
How this estimate is builtthe short version
I take the 18 most comparable recent sales nearby and adjust each one to this home for the real differences (size, beds, baths, garage, and standout features), then use the median, which is steadier than leaning on any single sale.
It’s grounded in recent closing prices, not asking prices. Lot, condition, and finishes are my in-person call, and the city (MPAC) assessment points to about $2.01M, a bit lower.
What the listing highlights3 points to weigh
Claims from the listing, worth confirming in person. I can book you a private showing.
- Finished basement: added living space, worth checking ceiling height and that the work was permitted. Value driver
- Addition / added square footage: more space lifts value when it is permitted and well integrated, verify the permits. Value driver
- Transit / schools nearby: convenience and resale support, verify the exact distances and school catchment. Value driver
Schools & getting aroundcatchment and transit
Its public catchment (Howard Junior Public School) tests around the provincial average, a steady, family-friendly draw. The full EQAO breakdown is below.
Based on 18 comparable homes that recently sold nearby.
The closest active listings by size, beds, and price, so you can see what this home is up against.
The 3 closest active listings nearby.
See all comparable homesOn the market now.
View comparable listingsPrice per square foot vs the area average.
Neighbourhood & location
High Park-Swansea, 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.
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 3.99% via Ratehub.ca (as of July 24, 2026); conventional rates run a little higher.
Mortgage amount $1,463,200 · 4.14% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $7,808
- Property tax
- $798
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $8,606
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $33,055
- Toronto municipal land transfer tax
- $33,055
- Estimated closing costs
- $66,110
Plus your down payment of $365,800. 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
- $468,491
- Principal paid down
- $186,339
- Interest paid
- $282,152
- Balance remaining
- $1,276,861
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.