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$1,829,000Asking Price

355 Parkside Drive, Toronto, ON M6R 2Z4

High Park, Toronto

Triplex
5
Bedrooms
4
Baths
5
Parking
Days on Market

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.

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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.

Key Info

  • 2.5-Storey Triplex
  • 4+ Parking
  • Detached Garage
  • Parkside Drive & Bloor Street W
  • 3000-3500 Approximate Sq Feet
  • No Ensuite Laundry
  • Radiant Gas Heating
  • No A/C

Property

  • Excludes: Heat, Hydro, Water, Cable TV, Central A/C, Common Elements, Building Insurance, Parking
  • Taxes were $9,576 in 2025

Details

  • Brick Exterior
  • No Fireplace
  • 3 Kitchens
  •  
  • MLS #W13487692
  • CORCORAN HORIZON REALTY

Extras

Room Floor Dimensions Details
1 Kitchen Main 9.58' x 11.25' Updated, Window
Washroom1 4-Piece Bathroom on Main Floor
Washroom1 4-Piece Bathroom
Washroom1 4-Piece Bathroom
Washroom1 2-Piece Bathroom

Who lives here?

High Park, Toronto is a west Toronto neighbourhood notable for its renters, university grads, executives and business, science, education, law & public sector and arts & culture professionals. Residents tend to be younger with a significant number of adults aged 25 to 49.

Families

Kids Per Family

0.9

kids per family
in the neighbourhood.

Toronto  (1.2)
Gta  ({{ '1.29999995231628' | number: 1 }})

Singles

49% of residents are
single and loving it.

49% singles

Toronto (50%)
Gta ({{ '44.8800010681152' | number: 0 }}%)

Renters

63% of residents
are renters.

63% renters

Toronto (47%)
Gta ({{ '33.0200004577637' | number: 0 }}%)

Education

64% of residents are
university grads.

64% university grads

Toronto (48%)
Gta ({{ '43.6699981689453' | number: 0 }}%)

Income

Average Household Income

$132K

is the average household
income in the neighbourhood.

Toronto  ($132K)
Gta  ({{ '135056.828125' | minifiedCurrency }})

Professions

Professions

Sales 13%
Government 13%
Business 12%
Management 10%
Sciences 9%

Immigrants

32% of residents were
born outside of Canada.

32% immigrants

Toronto (48%)
Gta ({{ '45.4300003051758' | number: 0 }}%)

Birthplace - All

Poland was once home to 2.7% of immigrants.
UK 2.0%
Ukraine 1.6%
India 1.6%
USA 1.4%

2.7% from Poland
All-time

Birthplace - Recent

India was once home to 0.5% of immigrants.
UK 0.5%
USA 0.3%
Ukraine 0.3%
Russia 0.3%

0.5% from India
Recent

Foreign Languages

Foreign Languages

Polish 3%
French 3%
Spanish 3%
Russian 2%
Ukrainian 2%

Religions

Religions

Christian 54%
Muslim 3%
Hindu 2%
Jewish 1%
Buddhist 1%

Social Housing

Social Housing Buildings

2

Social housing buildings
in the neighbourhood.

Gta Avg (5.19)

Shelters

Shelters

0

Homeless shelters in
the neighbourhood.

Gta Avg (0.54)