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.
Address
355 Parkside Drive
List Price
$1,799,000
MLS® Status
New
Property Type
Residential Freehold
Type of Dwelling
Triplex
Style of Home
2 1/2 Storey
Transaction Type
Sale
Area
Toronto W01
Sub-Area
High Park-Swansea
Region
Toronto
Bedrooms
5
Bedrooms (Total)
5
Rooms Above Grade
13
Bathrooms
4
Floor Area
3000-3500 Sq. Ft.
Lot Size Source
MPAC
Lot Depth
74.05
Lot Size Units
Feet
Lot Width
39.73
Parcel Number
213460080
Occupant Type
Tenant
Cross Street
Parkside Drive & Bloor Street W
MLS® Number
W13768692
Listing Brokerage
CORCORAN HORIZON REALTY
Basement Area
Full, Unfinished, Development Potential
Postal Code
M6R 2Z4
Posession Details
60-90 Days/TBA
Parking
Private
Parking Places (Total)
5
Parking Spaces
4
Tax Amount
$9,576.04
Tax Year
2025
Site Influences
Arts Centre, Beach, Hospital, Park, Place Of Worship, Porch, Porch Enclosed, Public Transit
Exterior Features
Porch, Porch Enclosed
Interior Features
Carpet Free, Floor Drain
Property Features
Arts Centre, Beach, Hospital, Park, Place Of Worship, Public Transit
Central Vacuum
No
Family Room
No
Ensuite Laundry
No
Special Designation
Unknown
Standard Status
Active
Senior Community
No
Board Or Association
Toronto Regional Real Estate Board
Heat Source
Gas
Heat Type
Radiant
Cooling Features
None
Construction Materials
Brick
Direction Faces
East
Fireplace
Yes
Fireplace Features
Freestanding
Foundation Details
Block, Stone
Garage
Yes
Garage Type
Detached
Covered Spaces
1
Kitchens Total
3
Kitchens Above Grade
3
Pool Features
None
Roof
Asphalt Shingle
Tax Legal Description
PT LT 70 PL 1277 TORONTO AS IN CT171106; CITY OF TORONTO
Waterfront
No
Sewer
Sewer
Rooms
| Floor | Type | Dimensions | Features |
|---|---|---|---|
| Main | Living Room | 4.32 x 4.27 | Closet, Hardwood Floor, Window |
| Main | Dining Room | 4.47 x 3.43 | Bow Window, Hardwood Floor |
| Main | Bedroom | 3.1 x 3.71 | Bow Window, Hardwood Floor |
| Main | Bedroom | 4.32 x 3.3 | Closet, Hardwood Floor, Window |
| Main | Kitchen | 2.92 x 3.43 | Updated, Window |
| Second | Living Room | 3.58 x 4.52 | Bow Window, Fireplace, Hardwood Floor |
| Second | Dining Room | 4.27 x 3.43 | Bow Window, Hardwood Floor |
| Second | Bedroom | 3.53 x 3.1 | Closet, Hardwood Floor, Window |
| Second | Bedroom | 3.71 x 3.1 | Hardwood Floor, Walk-In Closet(s), Window |
| Second | Kitchen | 3.18 x 3.43 | Updated, Window |
| Third | Living Room | 3.58 x 4.52 | Closet, Hardwood Floor, Window |
| Third | Bedroom | 3.48 x 4.52 | Hardwood Floor, Walk-In Closet(s), Window |
| Third | Kitchen | 2.79 x 3.18 | Window |