376 Sunnyside Avenue, Toronto

376 Sunnyside Avenue
376 Sunnyside Avenue
376 Sunnyside Avenue
+29
6
 bed
4
 bath
8
 parking
2000 - 2500
 sqft
Fourplex
$2,199,000
For Sale
45 days
 on site
$2,199,000
Click to open the pre-gallery to get the direction
Size
-
Lot size
3423 sqft
Street frontage
-
Possession
Flexible
Price per sqft
$880 - $1,100
Taxes
$10,270.66 (2025)
Parking Type
-
Style
2 1/2 Storey
See what's nearby
Description
Offered for the first time in two generations, a truly exceptional residence that presents a rare opportunity to acquire one of the neighbourhood's distinguished legacy properties. Occupying a prominent 27 x 126.81ft corner lot, this stately home seamlessly blends historic charm with remarkable versatility, offering endless possibilities for families, investors, builders, and those seeking a multigenerational residence in one of Toronto's most coveted communities.Encompassing 3,490 of total living space, the home welcomes you through a gracious vestibule that sets the tone for the impressive scale and timeless character. Generous principal rooms, abundant natural light, and enduring architectural details create an inviting atmosphere while providing the perfect canvas for restoration, modernization, or reimagining.Configured as a well-maintained income-producing property, the residence is occupied by exceptional tenants. The property offers outstanding flexibility with five separate hydro meters, a dedicated coin-operated laundry facility, and private balconies serving each of the above-grade suites-features that enhance both tenant appeal and long-term investment value. Modern mechanical upgrades include a tankless hot water system, providing efficient, on-demand hot water.Outside, the property's scale is equally impressive. A rare detached three-car garage complemented by parking for eight vehicles is virtually unheard of in this prestigious neighbourhood, creating unmatched convenience for homeowners, extended families, or investment use. The expansive corner lot further presents exciting opportunities for future enhancement or redevelopment and is garden suite eligible.Properties of this significance seldom become available. Rich in history, exceptional in scale, and brimming with future potential, 376 Sunnyside Avenue represents a once-in-a-generation opportunity to own a remarkable family legacy while creating the next chapter of its enduring story.
Broker: SOTHEBY'S INTERNATIONAL REALTY CANADA
MLS®#: W13509134
Property details
Parking:
8
Parking type:
-
Property type:
Fourplex
Heating type:
Radiant
Style:
2 1/2 Storey
MLS Size:
2000-2500 sqft
Lot front:
27 Ft
Lot depth:
126 Ft
Listed on:
Jul 1, 2026
Show all details
Rooms
LevelNameSizeFeatures
Third
Living Room
13.3 x 11.3 ft
Basement
Foyer
5.9 x 7.8 ft
Second
Living Room
18.6 x 11.1 ft
Show all
Instant estimate:
orto view instant estimate
$8,056
lower than listed price
i
High
$2,269,079
Mid
$2,190,944
Low
$2,080,704
Have a home? See what it's worth with an instant estimate

Use our AI-assisted tool to get an instant estimate of your home's value, up-to-date neighbourhood sales data, and tips on how to sell for more.

505 Parkside Drive
1/39
$2,049,000
110 days
505 Parkside Drive
5BD
4BA
1 Parking
2,000-2,500 sqft
MLS#: W13050314
ROYAL LEPAGE TERREQUITY BESPOKE REALTY
110 days
268 Sterling Road
1/39
$2,299,000
79 days
268 Sterling Road
4+1BD
3BA
2 Parking
2,000-2,500 sqft
MLS#: C13211386
RE/MAX WEST REALTY INC.
79 days
9 Fairview Avenue
1/38
Featured
$2,199,900
9 Fairview Avenue
4+1BD
3BA
4 Parking
2,000-2,500 sqft
MLS#: W13606320
PROPERTY.CA INC.
80 Northcote Avenue
1/20
$2,350,000
44 days
80 Northcote Avenue
3+1BD
4BA
3 Parking
2,000-2,500 sqft
MLS#: C13514426
FOREST HILL REAL ESTATE INC.
44 days

About 376 Sunnyside Avenue

376 Sunnyside Avenue is a Toronto fourplex for sale. It was listed at $2199000 in July 2026 and has 6 beds and 4 bathrooms. 376 Sunnyside Avenue resides in the Toronto High Park neighbourhood, and nearby areas include Roncesvalles Village, Junction Triangle , Little Portugal and Dufferin Grove.

376 Sunnyside Ave, Toronto is only a 7 minute walk from Cosettee Coffee for that morning caffeine fix and if you're not in the mood to cook, Grenadier Cafe & Tea House, Dairy Queen and King Slice are near this fourplex. For grabbing your groceries, Victoria Fruit Market is a 6-minute walk.

Living in this High Park fourplex is easy. There is also Howard Park Ave at Indian Rd Bus Stop, a short walk, with route Carlton nearby. If you're driving from 376 Sunnyside Ave, you'll have decent access to the rest of the city by way of Gardiner Expressway as well, which is within a few minutes drive getting on and off at Dowling Ave.