Toronto, ON
355 Parkside Drive
$1,799,000
Data last updated Oct 30, 2026, 6:20 p.m. ET. By using this site you agree to our Terms of Use.
Property facts
- Price
- $1,799,000
- Type
- triplex
- Bedrooms
- 5
- Bathrooms
- 4
- MLS®
- W13768692
- Status
- active
- Brokerage
- CORCORAN HORIZON REALTY
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.
Location
More details
- Property tax
- $9,576 (2025)
- Days on market
- 51
- Style
- 2 1/2 Storey
- Lot
- 39.73 × 74.05 Feet
- Parking
- 5 spaces · 1 garage · Detached
- Basement
- Full, Unfinished, Development Potential
- Heating
- Radiant
- Air conditioning
- None
- Neighbourhood
- High Park-Swansea
- Major intersection
- Parkside Drive & Bloor Street W
Rooms
| Room | Level | Size (m) | Features |
|---|---|---|---|
| Living Room | Main | 4.32 × 4.27 | hardwood floor, window, closet |
| Bedroom | Main | 4.32 × 3.3 | hardwood floor, window, closet |
| Dining Room | Main | 4.47 × 3.43 | hardwood floor, bow window |
| Bedroom | Second | 3.53 × 3.1 | hardwood floor, window, closet |
| Kitchen | Third | 2.79 × 3.18 | Window |
| Kitchen | Second | 3.18 × 3.43 | updated, window |
| Dining Room | Second | 4.27 × 3.43 | hardwood floor, bow window |
| Bedroom | Main | 3.1 × 3.71 | hardwood floor, bow window |
| Bedroom | Second | 3.71 × 3.1 | hardwood floor, window, walk-in closet(s) |
| Living Room | Second | 3.58 × 4.52 | hardwood floor, bow window, fireplace |
| Living Room | Third | 3.58 × 4.52 | hardwood floor, window, closet |
| Kitchen | Main | 2.92 × 3.43 | updated, window |
| Bedroom | Third | 3.48 × 4.52 | hardwood floor, window, walk-in closet(s) |
Details from PropTx (TRREB MLS®) via Repliers. Information deemed reliable but not guaranteed.