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.
For sale
C$1,799,000
355 Parkside Dr, Toronto, ON M6R 2Z4
5beds
4baths
Triplex
Built in ----
-- sqft lot
$-- Zestimate®
C$--/sqft
C$-- HOA
What's special
- 1 hour
- 8
- 1
Zillow last checked:
Listing updated:
Listed by:
CORCORAN HORIZON REALTY
Source: TRREB,MLS®#: W13768692
Originating MLS®#: Toronto Regional Real Estate Board
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
Heating
- Radiant, Gas
Cooling
- None
Features
- Floor Drain
- Flooring: Carpet Free
- Basement: Full,Unfinished,Development Potential
- Has fireplace: Yes
- Fireplace features: Free Standing
Interior area
- Living area range: 3000-3500 null
Property
Parking
- Total spaces: 5
- Parking features: Private
- Has garage: Yes
Features
- Stories: 2.5
- Patio & porch: Porch, Enclosed
- Pool features: None
Lot
- Size: 2,942 Square Feet
- Features: Arts Centre, Beach, Hospital, Park, Place Of Worship, Public Transit
Details
- Parcel number: 213460080
Construction
Type & style
- Home type: MultiFamily
- Property subtype: Triplex
Materials
- Brick
- Foundation: Block, Stone
- Roof: Asphalt Shingle
Utilities & green energy
- Sewer: Sewer
Community & HOA
Location
- Region: Toronto
Financial & listing details
- Annual tax amount: C$9,576
- Date on market: 9/10/2026
Price history
Price history is unavailable.
Public tax history
Tax history is unavailable.
Climate risks
Neighborhood: High Park
Nearby schools
GreatSchools rating
No schools nearby
We couldn't find any schools near this home.







