MLS® listing
355 Parkside Drive: triplex for sale
$1,799,000
From the listing brokerage
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.
Facts on the listing
| Square feet | 3000-3500 |
|---|---|
| Style | 2 1/2 Storey |
| Basement | Full, Unfinished, Development Potential |
| Lot width | 39.73 |
| Lot depth | 74.05 |
| Lot measured in | Feet |
| Faces | East |
| Parking spaces | 5 |
| Garage | Detached |
| Heating | Radiant |
| Cooling | None |
| Kitchens | 3 |
| Property tax | $9,576 |
| Tax year | 2025 |
| Parking | Private |
| Interior features | Carpet Free, Floor Drain |
| Features | Arts Centre, Beach, Hospital, Park, Place Of Worship, Public Transit |
Listing courtesy of CORCORAN HORIZON REALTY. MLS® W13768692.
About this triplex
355 Parkside Drive is a 5 bedroom triplex in TRREB's High Park-Swansea community in Toronto, listed for sale at $1,799,000. The listing shows 4 bathrooms and 3000-3500 square feet. The style is given as 2 1/2 storey. The lot is listed as 39.73 by 74.05 feet. The listing gives the basement as full, unfinished, development potential. It comes with 5 parking spaces and a detached garage according to the listing. The nearest main intersection given is Parkside Drive & Bloor Street W.
These details come from the listing brokerage through TRREB's MLS® System. Room sizes, the lot, the taxes and what is included in the sale should all be confirmed before an offer is firm.
What it costs to buy 355 Parkside Drive
At the asking price of $1,799,000, a buyer pays two land transfer taxes on closing: the Ontario tax and the City of Toronto's municipal tax. Both apply to every home inside the City.
| Asking price | $1,799,000 |
|---|---|
| Ontario land transfer tax | $32,455 |
| Toronto municipal land transfer tax | $32,455 |
| Both taxes | $64,910 |
| First-time buyer relief, if you qualify | up to $8,475 |
| Minimum down payment | $359,800 |
The down payment figure is the federal minimum: 20 percent, because a home at $1.5 million or more cannot carry mortgage default insurance. A lender can ask for more. These figures use the asking price, so they change if you pay more or less. Legal fees, title insurance and adjustments are extra: ask your lawyer for a written quote. This is general information, not legal or tax advice. Confirm the figures with a lawyer or accountant. You can change the price in our land transfer tax calculator and our mortgage calculator.
What it costs to own each month
| Property tax (2025) | $9,576 a year, about $798 a month |
|---|
That is before a mortgage payment, home insurance and utilities. The listing shows no monthly maintenance fee, so upkeep of the building and the lot is the owner's own cost.
What to check before you make an offer
- Book a home inspection. An inspector looks at the roof, foundation, wiring, plumbing and heating. The listing gives the heating as radiant.
- Have a lawyer search the title. A title search shows mortgages, liens and easements registered against the property. Ask whether a survey exists and whether it matches the lot on the listing, 39.73 by 74.05 feet.
- Ask about permits. Ask which renovations had building permits and whether those permits were closed. The listing shows 3 kitchens. If there is a second unit, ask whether it meets the municipality's rules for one.
- Confirm what is included. Appliances, light fixtures and window coverings are included only if the agreement says so. Ask whether the water heater or furnace is rented.
- Get your financing in writing. A lender looks at the property tax and heating costs as well as the price.
- See it in person. Photos do not show noise, light at different hours or the state of the street and the homes beside it.
Our first-time home buyer guide and our page for buyers walk through each step. This is general information, not legal advice. Confirm the details with a lawyer.
About High Park
Two TRREB communities on either side of Bloor Street West, sharing one very large park and four Line 2 subway stations. Houses and condo apartments trade here in roughly equal numbers.
Transit: Line 2 Bloor Danforth at High Park, Keele, Runnymede and Dundas West stations; 30 High Park North and 80 Queensway buses; Bloor GO (Kitchener line and UP Express) near Dundas West station
| Property type | Median | Sales and average |
|---|---|---|
| High Park-Swansea: all property types | $1,175,000 | 81 sales, average $1,283,066 |
| High Park-Swansea: detached | About $1,879,000 | 36 sales, average about $1,936,000 |
| High Park-Swansea: semi-detached | About $1,499,000 | 3 sales, average about $1,389,000 |
| High Park-Swansea: condo apartment | About $614,000 | 32 sales, average about $733,000 |
| High Park North: all property types | $1,345,500 | 46 sales, average $1,370,457 |
| High Park North: detached | About $1,790,000 | 13 sales, average about $2,035,000 |
| High Park North: semi-detached | About $1,615,000 | 11 sales, average about $1,679,000 |
| High Park North: condo apartment | About $810,000 | 21 sales, average about $803,000 |
Source: TRREB community housing market reports, as set out in the guide.
Questions about High Park
Is High Park a good place to live?
On housing and transit it offers a wide choice. Buyers can pick between detached houses with an April to June 2026 median of about $1,879,000 in High Park-Swansea and condo apartments near $614,000, with four Line 2 stations, a large City park and four library branches close by (TRREB, TTC, City of Toronto, TPL).
What does a detached house cost near High Park?
From April to June 2026 the detached median was about $1,879,000 across 36 sales in High Park-Swansea and about $1,790,000 across 13 sales in High Park North (TRREB). These are chart readings, so treat them as approximate.
Are there many condos in High Park?
Yes, especially north of Bloor. In the 2021 Census 59.6% of households in High Park North lived in apartment buildings of five or more storeys. Across both TRREB communities 53 of the 127 sales from April to June 2026 were condo apartments.
Which subway stations serve High Park?
Line 2 Bloor Danforth stops at High Park, Keele, Runnymede and Dundas West stations. Dundas West also connects to Bloor GO, which serves the Kitchener line and UP Express (TTC).
How far is High Park from Union station by subway?
From High Park station it is 9 stops east on Line 2 to St George, then 6 stops south on Line 1 to Union, 15 stops in all (TTC map).
Is High Park a heritage conservation district?
The City of Toronto's list of heritage conservation districts does not include one for High Park or Swansea. Individual properties can still be listed or designated, so check the specific address with the City before planning changes.
Read the High Park neighbourhood guide · All High Park homes for sale
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Questions about 355 Parkside Drive
How much is land transfer tax on 355 Parkside Drive?
At the asking price of $1,799,000 the Ontario tax is $32,455 and the Toronto tax is $32,455, $64,910 in total. A first-time buyer who qualifies can get up to $8,475 back. Confirm the final figures with your lawyer.
What is the minimum down payment for 355 Parkside Drive?
$359,800 at the asking price of $1,799,000, under the federal minimum down payment rules. A lender may require more.
How much is the property tax on 355 Parkside Drive?
The listing shows $9,576 a year for 2025, about $798 a month.
How do I book a showing for 355 Parkside Drive?
Use the form on this page or call us. Quote MLS® W13768692. We will confirm the listing is still available and arrange a time with the listing brokerage.
Is 355 Parkside Drive still for sale?
This page is refreshed from TRREB's MLS® System through the day. If the listing sells or is withdrawn the page says so. Contact us to confirm before you make plans.
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