355 Parkside Drive, Toronto, ON

Toronto, West Toronto, High Park-Swansea Hood
Parkside Drive & Bloor Street W
5 Br | 4 Bath | 3000-3500 Sqft
$1,829,000 For Sale

Property Overview

  • Triplex — 2 1/2 Storey
  • SqFt: | 3000-3500 Sqft
  • Lot Size: 39.73 x 74.05 Feet
  • Age: n/a
  • Basement: Full, Unfinished, Development Potential
  • Exterior: Brick
  • Taxes: 9,576 / 2025
  • Zoning: n/a
  • MLS #: W13487692
  • Sewer: Sewer
  • Heat Source: Gas , Radiant

Property Description

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 storeys, 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.

Three (3) refrigerators, Three (3) stoves, Washing Machine (Commercial Grade, coin operated), Dryer (Commercial Grade, coin operated).

Property Details

  • For: For Sale
  • Type: Triplex
  • Style: 2 1/2 Storey
  • Lot: 39.73 x 74.05 Feet
  • Region: Toronto
  • Hood: High Park-Swansea
  • Zoning: n/a
  • Lot Irreg: Fronting on: East
  • Fronting On: East

Building Details

  • Age: n/a
  • Exterior: Brick
  • Heat: Gas , Radiant
  • A/C: None
  • Interior Features: Carpet Free, Floor Drain
  • Pool: None
  • Sewer: Sewer
  • Garage: Detached
  • Total Parking: 5.00
  • Driveway: Private

Property Interior

  • Sqft: 3000-3500 Sqft
  • Bed: 5
  • Bath: 4
  • Kitchen: 3
  • Family Room: No
  • Basement: Full, Unfinished, Development Potential
Rooms Details

Living Room

Main Level

4.32 x 4.27

Hardwood Floor, Window, Closet

Dining Room

Main Level

4.47 x 3.43

Hardwood Floor, Bow Window

Bedroom

Main Level

3.1 x 3.71

Hardwood Floor, Bow Window

Bedroom

Main Level

4.32 x 3.3

Hardwood Floor, Window, Closet

Kitchen

Main Level

2.92 x 3.43

Updated, Window

Living Room

Second Level

3.58 x 4.52

Hardwood Floor, Bow Window, Fireplace

Dining Room

Second Level

4.27 x 3.43

Hardwood Floor, Bow Window

Bedroom

Second Level

3.53 x 3.1

Hardwood Floor, Window, Closet

Bedroom

Second Level

3.71 x 3.1

Hardwood Floor, Window, Walk-In Closet(s)

Kitchen

Second Level

3.18 x 3.43

Updated, Window

Living Room

Third Level

3.58 x 4.52

Hardwood Floor, Window, Closet

Bedroom

Third Level

3.48 x 4.52

Hardwood Floor, Window, Walk-In Closet(s)

Kitchen

Third Level

2.79 x 3.18

Window

Property Listed by: CORCORAN HORIZON REALTY
Virtual Tour: n/a

Home Valuation Estimate

What is 355 Parkside Drive, Toronto, ON worth in today’s High Park-Swansea, West Toronto market?

This HomeZira valuation preview helps buyers and sellers think through the asking price for this 5-bedroom Triplex with 3000-3500 sq. ft. in High Park-Swansea, West Toronto. The full estimate reviews the property’s location, home type, bedroom count, size range, age, and nearby comparable market activity after sign-in.

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Location

  • Address: 355 Parkside Drive
  • Neighborhood: High Park-Swansea
  • Zip/Postal Code: M6R 2Z4
  • Nearby Amenities: Arts Centre, Beach, Hospital, Park, Place Of Worship, Public Transit
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About 355 Parkside Drive, Toronto, ON M6R 2Z4, West Toronto

Located at 355 Parkside Drive, Toronto, ON in West Toronto (High Park-Swansea neighbourhood), near Parkside Drive & Bloor Street W. This freehold home offers Triplex, ["2 1\/2 Storey"], 5 bedrooms, 4 bathrooms and 3000-3500 sq.ft. (approx.) in a layout suited to everyday family living. Basement: Full, Unfinished, Development Potential • 5 parking spots • Garage: Detached • Heating: Gas Radiant • Cooling: None. Property taxes are approximately $9,576 for 2025. 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 storeys, 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 ca.

FAQs for 355 Parkside Drive, Toronto, ON , High Park-Swansea , West Toronto

What are the listing details for 355 Parkside Drive, Toronto, ON?
355 Parkside Drive, Toronto, ON is a Triplex for sale in West Toronto, in the High Park-Swansea neighbourhood, Toronto. The current list price is $1,829,000. MLS number: W13487692.
How many bedrooms and bathrooms does this home have?
355 Parkside Drive, Toronto, ON is listed as a Triplex with a ["2 1\/2 Storey"] style, featuring 5 bedroom(s) and 4 bathroom(s). The listed interior size range is 3000-3500 sq. ft..
What lot, basement, garage, or parking details are listed?
The lot size is listed as approximately 39.73 x 74.05 Feet. The basement is listed as: Full, Unfinished, Development Potential. Garage type: Detached. Total parking: 5 space(s).
What heating, cooling, and exterior details are shown?
Heating is listed as: Gas, Radiant. Cooling is listed as: None. Exterior/construction materials are listed as: Brick.
Where is this property located?
355 Parkside Drive, Toronto, ON is located in the High Park-Swansea neighbourhood of West Toronto. The listed cross street is Parkside Drive & Bloor Street W.
What information is available on this public listing page?
The public listing page shows current active listing information, property photos, room details when available, map location, listed price, property features, and contact options. Annual taxes are listed as $9,576 / 2025. Valuation tools and similar sold-property previews are available after sign-in where applicable, without displaying sold data in this public FAQ.

FAQ content is based on current active listing fields shown on this page. Sold prices, sold comparables, and VOW-only details are not included in this public FAQ.