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355 Parkside Drive in Toronto for sale

Asking price
$1,799,000
Estimate (Sep 10)
$1,776,422
MLS #:
W13768692
Type:
Triplex, 2 1/2 Storey
Approx. SQFT:
3000-3500
Basement:
Full, Unfinished
5 5
1 39.73 x 74.05 ft lot
PROPERTY HISTORY
SIGN IN REQUIRED
List Date List Price Last Status Sold Date Sold Price Days On Market
0000-00-00 $00000 Ter N/A N/A N/A
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.

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  • Date Listed: Thursday, September 10, 2026
  • Listing Brokerage: Corcoran Horizon Realty - Disclaimer: The information contained in this listing has not been verified by Corcoran Horizon Realty and should be verified by the buyer.
  • City: Toronto

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  • Neighbourhood: High Park-Swansea
  • Major Intersection: Parkside Drive & Bloor Street W
  • Full Address: 355 Parkside Drive, Toronto, M6R 2Z4, Canada, ON, Canada
  • Living Room: hardwood floor, Window, Closet
  • Kitchen: Updated, Window
  • Living Room: hardwood floor, Bow Window, Fireplace
  • Kitchen: Updated, Window
  • Living Room: hardwood floor, Window, Closet
  • Kitchen: Window
  • Amenities:
  • Taxes: $9,576.04 (2025)
Living14 x 14 ft196 sq ft
Dining15 x 11 ft165 sq ft
Br10 x 12 ft120 sq ft
Br14 x 11 ft154 sq ft
Kitchen10 x 11 ft110 sq ft
Living12 x 15 ft180 sq ft
Dining14 x 11 ft154 sq ft
Br12 x 10 ft120 sq ft
Br12 x 10 ft120 sq ft
Kitchen10 x 11 ft110 sq ft
Living12 x 15 ft180 sq ft
Br11 x 15 ft165 sq ft
Kitchen9 x 10 ft90 sq ft

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WHAT'S YOUR HOME WORTH?

Click here to get an instant estimate and track its value over time.