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$1,799,000

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355 Parkside Drive

High Park-Swansea, Toronto, Ontario M6R2Z4

For sale· Added

5 bed4 bath3,000–3,500 sqft

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

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Property details

Listing

MLS® number
W13768692
Added
Sep 10, 2026 ()
Updated
Sep 10, 2026 ()
Info refreshed

Overview

Property type
Multi-family
Building type
Triplex
Storeys
2.5

Inside

Bedrooms
5
Bathrooms
4
Half baths
1
Heating
Radiant heat, Natural gas
Cooling
None
Fireplace
Yes · Free Standing Metal
Flooring
Hardwood
Appliances
Washer, Refrigerator, Stove, Dryer
Features
Carpet Free

Building

Basement
Unfinished, Full
Exterior
Brick
Foundation
Stone, Block
Parking
Detached Garage, Garage · 5 spaces

Land

Lot size
39.7 x 74.1 ft

Services

Water
Municipal water
Sewer
Sanitary sewer

Location

Cross streets
Parkside Drive & Bloor Street W

Running costs

Annual property tax
$9,576

Rooms

Living roomMain level4.32 x 4.27 m
Living roomThird level3.58 x 4.52 m
BedroomThird level3.48 x 4.52 m
KitchenThird level2.79 x 3.18 m
Dining roomMain level4.47 x 3.43 m
BedroomMain level3.1 x 3.71 m
BedroomMain level4.32 x 3.3 m
KitchenMain level2.92 x 3.43 m
Living roomSecond level3.58 x 4.52 m
Dining roomSecond level4.27 x 3.43 m
BedroomSecond level3.53 x 3.1 m
BedroomSecond level3.71 x 3.1 m
KitchenSecond level3.18 x 3.43 m

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$1,799,000
355 Parkside Drive
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