355 Parkside Drive, Toronto W01, ON

$1,829,000
MLS#:W13487692
5 beds
4 baths
3000-3500 sqft
5.0 parking
Residential Freehold
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Property Highlights

Welcome to this remarkable 2 1/2 Storey triplex located in the coveted neighborhood of High Park-Swansea. Expertly crafted featuring premium brick construction, this residence presents an exceptional opportunity offered at $1,829,000 to acquire a beautiful home in a highly sought-after setting. Designed for both comfortable daily living and elegant entertaining, the layout maximizes natural light, functional flow, and lifestyle utility.

  • 5 Bedrooms and 4 Bathrooms with 3 functional kitchens
  • Generous living space spanning 3000-3500 sqft on a premium 93.37 x 74.23 ft lot
  • Features a full, unfinished, development potential basement, adding superb versatility for recreation, a home gym, or extra storage
  • 5.0 total parking spaces available with a convenient detached configuration
  • Notable attributes: Carpet Free, Floor Drain
  • Efficient radiant heating via gas

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.

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Key Features

Bedrooms
5
Bathrooms
4
Kitchens
3
Living Area
3000-3500 sqft
Property Type
Residential Freehold

Additional Details

StatusActive
Listed Date6/25/2026
Transaction TypeFor Sale

Property Details

Property Sub-TypeTriplex
Architectural Style2 1/2 Storey
ConstructionBrick
BasementFull, Unfinished, Development Potential
Lot Size93.37 × 74.23 Feet
CountyToronto
Annual Tax$9,576.04
Legal DescriptionPT LT 70 PL 1277 TORONTO AS IN CT171106; CITY OF TORONTO

Parking & Garage

Parking Spaces5.0
Garage Spaces4
Garage TypeDetached

Heating & Cooling

Heat SourceGas
Heat TypeRadiant
CoolingNone

Features

Property Features

Arts Centre, Beach, Hospital, Park, Place Of Worship, Public Transit

Interior Features

Carpet Free, Floor Drain

Security Features

Community Features

Location

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355 Parkside Drive, Toronto W01, ON
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Property History

No historical data available for this property.

This could be the first listing for this address.

Pricing & Value Insights

Data-driven valuation for 355 Parkside Drive, Toronto, ON M6R 2Z4

Estimated Sales Range
$1.2M - $1.4M

Based on 0 recent similar sales in the pocket.

Market Speed
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Properties in this area are selling at a steady pace.

Market Trend
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Financial Audit

Estimated Costs

Loan Amount$1,463,200
Monthly Mortgage$8,502
Property Tax (Est.)$798
Utilities & Maint.$350
Total Monthly Cost$9,650

Nearby School Rankings

No schools found within 3 km of this property.

Within 2km radiusFraser Institute Ratings

Nearby Listings

Distance:

No current listings found in Toronto W01.

Similar Listings Nearby

City & Neighborhood Guide

Comprehensive city-wide demographics, local real estate stats, and school rankings for High Park Swansea, Toronto W01.

Verified Local Data
City Population2,794,356
City Median Age39.2 Yrs
City Ownership48% Owners
Avg Area List Price$1,494,418

People & Families

Age Distribution

Household Composition

One-person households
32%
Families with children
36%
Couples without children
24%
Other households
8%

Top Ethnic Origins

Chinese11%
English9%
Canadian8%
East Indian8%

Local Schools Guide

Elementary Schools

Swansea
Public207 Windermere Avenue, High Park-Swansea, Toronto, Ontario, M6S 3J9
7.7
St Pius X
Public71 Jane Street, Toronto, Ontario, M6S 3Y3
8.3
Howard
Public30 Marmaduke Street, High Park-Swansea, Toronto, Ontario, M6R 1T2
7.6
Garden Avenue
Public225 Garden Avenue, High Park-Swansea, Toronto, Ontario, M6R 1M9
7.7
Keele Street
Public99 Mountview Avenue, Toronto, Ontario, M6P 2L5
6.7

Secondary Schools

Western
Public125 Evelyn Crescent, Toronto, Ontario, M6P 3E3
6.8
Ursula Franklin
Public146 Glendonwynne Road, Toronto, Ontario, M6P 3J7
9.7
Pope John Paul II
PublicFern Avenue, High Park-Swansea, Toronto, Ontario, M6R 2L4
6.7
Humberside
Public280 Quebec Avenue, Toronto, Ontario, M6P 2V3
9.0

Homes & Housing

Structural Home Types

Tenure (Ownership vs Rental)

Owner-Occupied48%
Rented52%

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Disclaimer: AI Insights are generated by an automated system and should be used for informational purposes only. While we strive for accuracy using current market data and deep-learning models, these assessments do not constitute professional real estate, legal, or financial advice. All property values, predictions, and scores are estimates. We strongly recommend verifying all property details and conducting independent due diligence with a licensed professional before making any purchase decisions.