Sell With Julia
← Back to listings
Photo of 355 Parkside Drive Map

355 Parkside Drive

Toronto (High Park-Swansea), Ontario M6R2Z4

MLS # W13768692

$1,799,000

Property Details

Type

Triplex

Beds

5

Baths

4

Status

For Sale

About this property

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.

Mortgage Estimate

Estimated monthly payment

Calculating…

Estimate only. Taxes, insurance, condo fees, and lender terms are not included.

Monthly costs to verify

Property taxes: about $798/month based on listed annual taxes.

Estimate only. Confirm taxes, condo/maintenance fees, insurance, utilities, and lender terms before making decisions.

Rooms

Room Level Dimensions
Living room Main level 4.32 x 4.27
Living room Third level 3.58 x 4.52
Bedroom Third level 3.48 x 4.52
Kitchen Third level 2.79 x 3.18
Dining room Main level 4.47 x 3.43
Bedroom Main level 3.1 x 3.71
Bedroom Main level 4.32 x 3.3
Kitchen Main level 2.92 x 3.43
Living room Second level 3.58 x 4.52
Dining room Second level 4.27 x 3.43
Bedroom Second level 3.53 x 3.1
Bedroom Second level 3.71 x 3.1
Kitchen Second level 3.18 x 3.43

Facts & Location

Interior Size

1,233 sq ft

Parking

5 spaces

Lot Size

39.7 x 74.1 FT

Annual Taxes

$9,576

Listing data

Listing information is provided for personal, non-commercial use and should be independently verified before making real estate decisions.

Last refreshed: Sep 10, 2026 6:00 PM

Similar Properties

More nearby listings that may fit the same search.

View all
Contact Julia About This Property