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Murat Sahiner, Broker | Home6 Team at RE/MAX Realtron Realty Inc., Brokerage | 88 Konrad Crescent, Markham, ON L3R 8T7

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355 Parkside Drive Toronto W01
For SaleHigh Park-Swansea

355 Parkside Drive Toronto W01, Triplex for Sale

MLS® W13768692

High Park-Swansea, Toronto, ON

58 days on market
$1,799,000
Show on Map
Show on Map
5Beds
4Baths
3,250Sqft
5Parking
Triplex

Overview· 355 Parkside Drive Toronto

MLS® #W13768692

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.

Inclusions

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

Exclusions

Tenants' art, belongings and furnishings.

Broker

CORCORAN HORIZON REALTY

Neighbourhood

High Park-Swansea

Walk 61Avg $1.37MArea guide

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Walk Score®74Very WalkableVery Walkable
Transit Score®89Excellent TransitExcellent Transit
Bike Score®70Very BikeableVery Bikeable
Schools10012 schools within 1.5 km12 schools within 1.5 km
Parks10064 parks within 1 km64 parks within 1 km
Convenience100138 groceries, cafes and pharmacies within 1 km138 groceries, cafes and pharmacies within 1 km
Safety81Safer than 81% of Toronto neighbourhoods (2025)High Park-Swansea: 1,064 incidents per 100,000 residents in 2025, across all crime types, ranked against 158 Toronto neighbourhoods. Toronto counts resident population only, so business and entertainment districts rank worse than residents experience. Source: Toronto Police Services.

Highlights & Amenities· 355 Parkside Drive Toronto

Source: MLS® listing data
355 Parkside Drive Toronto

Triplex

355 Parkside Drive Toronto

High Park-Swansea

Type

Triplex

Basement

Full, Unfinished, Development Potential

Parking

Detached (5)

Property Tax

~$9,576/yr

Heating

Radiant

Buying Essentials

Square Feet

3250 sqft

Facing Direction

East

Parking

Detached (5)

Finances

List Price

$1,799,000

Price per SQFT

$554/sqft

Property Tax

~$9,576/yr

Property Specs

Property Type

Triplex

MLS Size

3250 sqft

Basement

Full, Unfinished, Development Potential

Living & Amenities

Heating Type

Radiant

Features

Carpet Free · Floor Drain

Policies & Utilities

Neighbourhood

High Park-Swansea

Listed On

Sep 10, 2026

Arts Centre

Beach

Hospital

Park

Place Of Worship

Public Transit

Price & Listing History

Days on Market

Current: 58 days

0306090120+

Rooms

Living Room(Main)

Hardwood Floor, Window, Closet

14.2 x 14.0

199 sqft

Dining Room(Main)

Hardwood Floor, Bow Window

14.7 x 11.3

165 sqft

Bedroom(Main)

Hardwood Floor, Bow Window

10.2 x 12.2

124 sqft

Bedroom(Main)

Hardwood Floor, Window, Closet

14.2 x 10.8

153 sqft

Kitchen(Main)

Updated, Window

9.6 x 11.3

108 sqft

Living Room(Second)

Hardwood Floor, Bow Window, Fireplace

11.7 x 14.8

174 sqft

Dining Room(Second)

Hardwood Floor, Bow Window

14.0 x 11.3

158 sqft

Bedroom(Second)

Hardwood Floor, Window, Closet

11.6 x 10.2

118 sqft

Bedroom(Second)

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

12.2 x 10.2

124 sqft

Kitchen(Second)

Updated, Window

10.4 x 11.3

117 sqft

Living Room(Third)

Hardwood Floor, Window, Closet

11.7 x 14.8

174 sqft

Bedroom(Third)

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

11.4 x 14.8

169 sqft

Kitchen(Third)

Window

9.2 x 10.4

95 sqft

RoomsDimensionsFeaturesSqft
Living Room(Main)14.2 x 14.0Hardwood Floor, Window, Closet199
Dining Room(Main)14.7 x 11.3Hardwood Floor, Bow Window165
Bedroom(Main)10.2 x 12.2Hardwood Floor, Bow Window124
Bedroom(Main)14.2 x 10.8Hardwood Floor, Window, Closet153
Kitchen(Main)9.6 x 11.3Updated, Window108
Living Room(Second)11.7 x 14.8Hardwood Floor, Bow Window, Fireplace174
Dining Room(Second)14.0 x 11.3Hardwood Floor, Bow Window158
Bedroom(Second)11.6 x 10.2Hardwood Floor, Window, Closet118
Bedroom(Second)12.2 x 10.2Hardwood Floor, Window, Walk-In Closet(s)124
Kitchen(Second)10.4 x 11.3Updated, Window117
Living Room(Third)11.7 x 14.8Hardwood Floor, Window, Closet174
Bedroom(Third)11.4 x 14.8Hardwood Floor, Window, Walk-In Closet(s)169
Kitchen(Third)9.2 x 10.4Window95

Rooms

13

Listed Room Area

1,878 sqft

Source

Estimated from MLS room dimensions

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Nearby Schools

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Mortgage Calculator

Mortgage Summary

Mortgage Payment$7,236/mo
Property Tax$798/mo
Total Monthly$8,034

Monthly Cash Flow (investors)

$
Net Cash FlowN/A

Closing Costs

Estimated closing costs$0
Cash required incl. down payment$0