355 Parkside Drive, Toronto, ON M6R 2Z4
High Park-Swansea, Toronto · Near Parkside Drive & Bloor Street W · View map
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 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.
The home
- Type
- Triplex
- Style
- 2 1/2 Storey
- Square footage
- 3000-3500 sq ft
- Bedrooms
- 5
- Bathrooms
- 4
- Kitchens
- 3
- Rooms
- 13
- Basement
- Full, Unfinished, Development Potential
- Lot size
- 39.7 x 74.1 ft
- Faces
- East
Ownership & fees
- Ownership
- Freehold
- Monthly condo fee
- None
- Exterior
- Brick
Heating & cooling
- Heating fuel
- Gas
- Heating type
- Radiant
- Fireplace
- Yes
Garage & parking
- Garage
- Detached
- Garage spaces
- 1
- Driveway spaces
- 4
- Total parking
- 5
- Parking features
- Private
Taxes & other
- Property taxes
- $9,576/yr
- Tax year
- 2025
- Occupancy
- Tenant
- Possession
- 60-90 Days/TBA
- Cross street
- Parkside Drive & Bloor Street W
- Neighbourhood
- High Park-Swansea
More
- Price per sq ft
- ~$554 (at 3,250 sq ft)
- MLS® number
- W13768692
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The home and its surroundings
- Carpet Free
- Floor Drain
- Arts Centre
- Beach
- Hospital
- Park
- Place Of Worship
- Public Transit
- Porch
- Porch Enclosed
- Mortgage
- Property tax
- Maintenance fee
Cash needed to close
Estimates only, using Canadian semi-annual compounding, Ontario land transfer tax and Toronto municipal land transfer tax. Mortgage default insurance is added when you put down less than 20%. Your lender and lawyer will confirm exact numbers.
355 Parkside Drive, Toronto, ON M6R 2Z4
High Park-Swansea, Toronto · Near Parkside Drive & Bloor Street W
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Listing history for 355 Parkside Drive
See what this home and others at the same address were listed for, what they sold for, and how long it took.
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Frequently asked questions about 355 Parkside Drive
Answers come straight from this home’s MLS® listing.
How much is 355 Parkside Drive listed for, and what would it cost each month?
355 Parkside Drive is listed for $1,799,000. With 20% down ($359,800), the mortgage payment would be roughly $7,257 a month at 4.5% over 30 years. Add property tax and the estimate comes to about $8,055 a month, all in. That figure is an illustration, not a quote.
Is 355 Parkside Drive freehold or a condo, and is there a monthly fee?
355 Parkside Drive is a triplex in High Park-Swansea, Toronto. Ownership is freehold: you own the home and the lot. There is no monthly condo fee, so the roof, windows, driveway, snow and lawn are yours to look after.
How many bedrooms and bathrooms does 355 Parkside Drive have?
355 Parkside Drive has 5 bedrooms and 4 bathrooms. The listing gives the style as 2 1/2 storey.
Does 355 Parkside Drive have a garage and parking?
Yes. The listing shows the garage as detached, with room for 1 car. The driveway adds 4 spaces. In total the listing counts 5 parking spaces.
Does 355 Parkside Drive have a finished basement?
The listing describes the basement as full, unfinished, development potential.
What style of home is 355 Parkside Drive?
355 Parkside Drive is a triplex. A multiplex holds two or more separate units under one roof, often bought to live in one unit and rent the others.
How big is 355 Parkside Drive, and what is the lot size?
The listing puts the home between 3,000 and 3,500 sq ft. The board reports a range rather than an exact figure, and it usually leaves out the basement. The lot is listed as 39.7 x 74.1 ft.
How is 355 Parkside Drive heated and cooled?
Heating is radiant (gas). The listing does not show air conditioning.
What are the property taxes for 355 Parkside Drive?
Property taxes are $9,576 a year (2025), or about $798 a month.
Where is 355 Parkside Drive?
355 Parkside Drive is in the High Park-Swansea community of Toronto. The nearest main intersection is Parkside Drive & Bloor Street W. The postal code is M6R 2Z4.
Is 355 Parkside Drive still for sale?
Yes. It is an active listing (MLS® W13768692). Listings here update from the board through the day and come down once a home sells.
What are similar properties near 355 Parkside Drive asking?
Similar properties for sale nearby right now include 505 Parkside Drive at $1,895,000 (5 bed), 189 Parkside Drive at $1,999,000 (5+1 bed) and 298 South Kingsway at $1,990,000 (6 bed). These are asking prices, not sold prices. The Sold history tab shows what homes at this address went for.
What have homes at 355 Parkside Drive sold for?
Recent sales, leases and expired listings for this home and others at the same address are in the Sold history tab, with the price and date of each. It is free for members.
How do I book a showing at 355 Parkside Drive?
Pick a day and time with Book a Tour on this page. Tours are free, with no obligation, in person or by video. You can also call or text 647-931-3923.
Have a different question? Ask about this home and get an answer, usually within the hour.
Similar properties nearby
More properties for sale near High Park-Swansea, picked by style, size and price.
Triplex$1,895,000505 Parkside Drive, Toronto5 bed · 4 bath · High Park-SwanseaCourtesy of: ROYAL LEPAGE TERREQUITY BESPOKE REALTYView home →
Fourplex$1,999,000189 Parkside Drive, Toronto5+1 bed · 4 bath · High Park-SwanseaCourtesy of: GRANGE HALL REALTY INC.View home →
Triplex$1,990,000298 South Kingsway, Toronto6 bed · 5 bath · High Park-SwanseaCourtesy of: INX LANDMARK REALTYView home →Courtesy of: CORCORAN HORIZON REALTY
Listing information comes from the Toronto Regional Real Estate Board through PropTx and is deemed reliable but is not guaranteed accurate. It is provided for consumers' personal, non-commercial use. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA.
*Estimated monthly cost assumes 20% down, a 4.5% rate and a 30-year amortization, plus property tax. For illustration only.