355 Parkside Drive

FOR SALE
$1,799,000
355 Parkside Drive, Toronto
355 Parkside Drive
355 Parkside Drive
355 Parkside Drive
355 Parkside Drive
355 Parkside Drive
355 Parkside Drive
355 Parkside Drive
355 Parkside Drive
355 Parkside Drive
355 Parkside Drive
355 Parkside Drive
355 Parkside Drive
355 Parkside Drive
355 Parkside Drive
355 Parkside Drive
355 Parkside Drive
355 Parkside Drive
355 Parkside Drive
355 Parkside Drive
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5
BEDROOMS
4
BATHROOMS
3
KITCHENS
13
ROOMS
W13768692
MLSID
Contact Us
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 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.
Nearby Intersections
Property Features
Arts Centre, Beach, Hospital, Park, Place Of Worship, Public Transit, Carpet Free, Floor Drain, Private, Freestanding
Property Details
Address
355 Parkside Drive
Postal Code
M6R 2Z4
Property Type
Triplex, Triplex
Lot Size
40' x 74'
Taxes
$9,576 (2025
Basement
Full, Unfinished, Development Potential
Exterior
Porch, Porch Enclosed
Heat Type
Radiant
Heat Source
Gas
Water
Municipal
Parking Spaces
4
Garage Type
Detached
Listing contracted with Corcoran Horizon Realty
272 Seaton Street, Toronto
5
BEDS
3
BATHS
$1,750,000
FOR SALE
Brand New Rebuilt - Double Brick - Triplex in Downtown Toronto! Complete Gut-Renovation down to the studs, with completion in approx.6 weeks. 3 Legal Separate Suites - All Built to new codes, with separate meters, hardwired fire system, New Roof, New Main Staircase, New Insulation, New Drywall, New Floors, Brand New Modern Kitchens, with Dishwashers. A 3 year complete renovation on a very large victorian home, with 7, yes SEVEN parking spaces, a ~163 foot deep lot with fenced backyard. Potential for 2 floor garden home addition, fourth unit in basement (high ceilings). Boasting, Two 2 Bedroom Units with 12' high ceilings, and 1 large loft unit with an additional 1 bedroom, vaulted ceilings and a massive 19'x7' Private Deck. Perfect for "growing into" this spectacular victorian for end users or investors. All building under city permits.
434 Victoria Park Avenue, Toronto
5+1
BEDS
4
BATHS
$1,550,000
FOR SALE
OPEN HOUSE SATURDAY 11/14/2026 1:00 PM - 3:00 PM! Modern Triplex. You get what you pay for; excellent cap rate, mint condition and prime location. Welcome to 434 Victoria Park Ave. Over 3040 Sq Ft., fully updated 3 units spread over 4 levels. This impeccably renovated legal modern triplex is located in the Upper Beach area just off the trendy Kingston Road shopping district. Excellent designed and well maintained property features three (3) modern self-contained units, each tastefully designed and each unit has its own private entrance, it's own in-suite laundry and 1 front parking pad and 2 car garage at rear (garden suite compliant). This building has been recently re-designed for maximum impact, efficiency and income potential. All units have been appointed with quality materials and built with superior craftsmanship and completed with modern appliances. The detached double car garage provides additional upside potential for increased income and potential for garden suite re-development. This home is equipped with 2 furnaces, 2 hot water tank-less heaters, and 2 A/C units for efficient climate control and comfort. Three (3) hydro meters and two (2) gas meters also make this property easy for a landlord to manage. This is a turnkey investment opportunity or live in one and rent out the other 2 units making home ownership very affordable. Enjoy the convenience and economy of a full sized "live-in" property with low maintenance and exceptional income and upside potential. (garden suite compliant).
725 Indian Road, Toronto
4+1
BEDS
3
BATHS
$1,499,000
FOR SALE
** CHARMING! Exceptional Investment Opportunity in High Park North! ** High-Cash-Flow (5.2% Cap) Triplex in One of Toronto's Most Desirable Neighbourhoods! Featuring 3 Well-Designed Legal Apartments with unique character, cozy vibes, and spacious private decks: 1 Two-Bedroom Unit + 2 One-Bedroom Units. A Rare Bonus: One-of-a-Kind Garden Cabin-Perfect for a Home Office, Creative Studio, Hobby Room, or Guest Retreat! Live in One Unit and Let the Other Two Help Pay Your Mortgage! Each unit is currently tenanted on a month-to-month basis with wonderful tenants at excellent market rents, while the lower-level two-bedroom unit including the garden cabin will be vacant as of December 1-offering exceptional flexibility for owner-occupiers, investors, or multi-generational living. Shared coin-operated laundry provides an additional income stream. Enjoy an unbeatable location just a short walk to the vibrant shops and restaurants of The Junction and Bloor Street, Dundas West and Keele subway stations, UP Express and GO Transit, and the beautiful trails and green spaces of High Park. Set on a lovely, tree-lined street in a welcoming community, this distinctive property combines income potential, lifestyle appeal, and urban convenience. ** A Rare Opportunity to Own a Versatile, Turn-key Income Property in a Prime Toronto Neighbourhood! A Must-See! **
28 Concord Avenue, Toronto
6
BEDS
4
BATHS
$1,450,000
FOR SALE
If you value large scale and versatility, this grand three-storey Edwardian on a 25' x 137' lot will offer you choices. Be charmed by the original stained glass, hardwood floors, soaring ceilings, oversized windows & an optimized east-facing front porch. With over 3000 SqFt of usable space in the entire home, reimagine a single-family home, multigenerational living or continue generating rental income by maintaining separation. 2 entrances are located at the front & 1 on the side. The currently tenanted main level of approximately 850 SqFt features generous storage and walk-in closets. The staircase to the second and third floors are exceptionally wide. The upper levels have been recently vacated by the owner and form one spacious unit of approx 1,500 SqFt ideal for an owner's residence or rental suite. The generous layout features separate living and dining rooms, a den, three generously sized bedrooms and two full 4-piece bathrooms. The basement, accessible via the side entrance, provides additional square footage. It was previously used as a separate living space with a kitchen, washroom and 3 additional rooms with windows. The deep west-facing backyard unfolds into distinct zones for gardening, play & entertaining, creating a private urban retreat with afternoon and evening sun. A legal front-yard parking pad adds valuable urban convenience. Ideally situated just north of College Street, walk to the highly rated Dewson St School & north to the subway, Dufferin Mall, CTA High School and neighbourhood parks. The Ossington Strip, Little Italy, Trinity Bellwoods, independent shops and cafés are all nearby, with the University of Toronto just a quick commute away. A distinguished Toronto grand dame held by the same family for more than 55 years with remarkable proportions, enduring character and incredible possibilities - ready for your design, update or renovate and become part of its story.
104 Dixon Road, Toronto
5
BEDS
3
BATHS
$1,399,000
FOR SALE
RARELY OFFERED DETACHED TRIPLEX IN TORONTO'S WESTON NEIGHBOURHOOD! THIS SOLID DOUBLE-BRICK PROPERTY FEATURES 3 SELF-CONTAINED RESIDENTIAL UNITS, EACH WITH A SEPARATE ENTRANCE, AND 4 SEPARATE HYDRO METERS. THE PROPERTY IS FULLY TENANTED AND OFFERS AN ATTRACTIVE OPPORTUNITY FOR INVESTORS OR MULTI-GENERATIONAL LIVING. INTERIOR UPDATES AND MECHANICAL FEATURES INCLUDE A GOODMAN FURNACE AND NORITZ TANKLESS WATER HEATER. THE LOWER LEVEL FEATURES HIGH CEILINGS, WHILE TWO SEPARATE STAIRWELLS PROVIDE ACCESS BETWEEN AREAS OF THE HOME. ADDITIONAL FEATURES INCLUDE A PRIVATE DRIVEWAY, FENCED BACKYARD, AND SHARED COIN-OPERATED LAUNDRY. CONVENIENTLY LOCATED NEAR PUBLIC TRANSIT, SCHOOLS, PARKS, THE HUMBER RIVER, WESTON GOLF CLUB, TORONTO PEARSON INTERNATIONAL AIRPORT, AND MAJOR HIGHWAYS. EXISTING APPLIANCES, COIN-OPERATED WASHER AND DRYER, WINDOW COVERINGS, AND LIGHT FIXTURES ARE INCLUDED, EXCLUDING TENANTS' BELONGINGS. A VERSATILE MULTI-UNIT PROPERTY IN AN ESTABLISHED TORONTO NEIGHBOURHOOD.
96 Wesley Street, Toronto
5+1
BEDS
3
BATHS
$1,499,999
FOR SALE
Attention investors, builders, and developers - an exceptional opportunity at 96 Wesley Street in the highly sought-after Stonegate-Queensway community. This 3,072 sq ft triplex sits on a lot that has been subdivided into two 25 x 125 ft parcels, with approvals in place for the construction of two detached homes. Development permits have been approved and are ready, with permit fees remaining to be paid. Architectural drawings for both detached dwellings are available.The existing property features three spacious self-contained units, offering a total of 5 bedrooms, 3 kitchens, and 3 full 4-piece bathrooms, providing immediate rental income while you plan your next project.With parking for up to 8 vehicles, including a private driveway and 2-car garage, this property offers strong holding potential and exceptional long-term value. Both subdivided lots must be sold together.Ideally situated with convenient access to the Gardiner Expressway and public transit, and just a short walk to Grand Avenue Park and Queensway Park. Surrounded by top-rated schools, local shops, restaurants, and everyday amenities, this is a rare development opportunity in one of Toronto's most established and desirable west-end neighbourhoods.Seller prefers this property to be sold together with 100 Wesley Street (MLS W13520460).
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