157 m
Distance
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. Reconfigure to design your family home or assume this already configured and well-maintained income-producing property. 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/garden suite use. The expansive corner lot 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. (id:58753)
Cross Streets: Howard Park and Sunnyside Ave. ** Directions: corner of sunnyside avenue and marmadukee.
Source: Public Records
Discover key demographics, population statistics, and environmental insights for the Toronto (high Park-Swansea), ON area.
98/100
Walker's Paradise
Walk Score ®
97/100
Rider's Paradise
Transit Score ®
94/100
Biker's Paradise
Bike Score ®
Daily errands do not require a car. World-class public transportation. Daily errands can be accomplished on a bike.
24 nearby routes: 16 bus, 8 rail, 0 other
The average walkability score in the surrounding area is Walk Score: 80/100, Transit Score: 77/100, Bike Score: 75/100.
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4 bds • 4 ba • 0 sqft
168 LANSDOWNE AVENUE, Toronto W01, ON M6K2V9
7 bds • 4 ba • 0 sqft
323 BROCK AVENUE, Toronto, ON M6K2M6
4 bds • 6 ba • 0 sqft
1531 DUPONT STREET, Toronto W02, ON M6P3S3
5 bds • 4 ba • 0 sqft
138 HEPBOURNE STREET, Toronto, ON M6H1K7
3 bds • 3 ba • 0 sqft
PH3 - 270 DUFFERIN STREET, Toronto W01, ON M6K0H8
6 bds • 3 ba • 0 sqft
280 GRACE STREET, Toronto, ON M6G3A6
5 bds • 6 ba • 0 sqft
141 CHRISTIE STREET, Toronto, ON M6G3B3
4 bds • 3 ba • 0 sqft
224A MANNING AVENUE, Toronto, ON M6J2K7
5 bds • 4 ba • 0 sqft
75 SLOPING SKY MEWS, Toronto C01, ON M5V1P3
3 bds • 3 ba • 0 sqft
6 ANNEX LANE, Toronto, ON M5R3V2
4 bds • 4 ba • 0 sqft
6 MARQUIS AVENUE, Toronto, ON M8X1V4
3 bds • 3 ba • 0 sqft
836 - 8 TELEGRAM MEWS, Toronto C01, ON M5V3Z5
4 bds • 5 ba • 0 sqft
66A VICTOR AVENUE, Toronto, ON M8V2L9
4 bds • 2 ba • 0 sqft
4402 - 99 JOHN STREET, Toronto C01, ON M5V0S6
2 bds • 3 ba • 0 sqft
406 - 55A AVENUE ROAD, Toronto C02, ON M5R2G3
3 bds • 3 ba • 0 sqft
205 - 77 AVENUE ROAD, Toronto, ON M5R3R8
4 bds • 4 ba • 0 sqft
21 HAROLD STREET, Toronto W06, ON M8Z3R4
3 bds • 3 ba • 0 sqft
3 FLAX FIELD LANE, Toronto, ON M2N0L5
4 bds • 3 ba • 0 sqft
195 GLEN CEDAR ROAD, Toronto C03, ON M6C3G9
3 bds • 2 ba • 0 sqft
56 CAMBERWELL ROAD, Toronto, ON M6C3E8
3 bds • 2 ba • sqft
308 - 384 SUNNYSIDE AVENUE
3 bds • 3 ba • 0 sqft
202 - 384 SUNNYSIDE AVENUE
7 bds • 4 ba • 0 sqft
415 PARKSIDE DRIVE
6 bds • 4 ba • sqft
376 SUNNYSIDE AVENUE
bds • 5 ba • 3300 sqft
2243 DUNDAS STREET W
bds • 5 ba • 3300 sqft
2243 DUNDAS STREET W
bds • 0 ba • 5285 sqft
2261 DUNDAS STREET W
4 bds • 4 ba • sqft
2261 DUNDAS STREET W
5 bds • 3 ba • sqft
296 WRIGHT AVENUE
6 bds • 4 ba • sqft
189 PARKSIDE DRIVE
5 bds • 3 ba • sqft
268 STERLING ROAD
4 bds • 5 ba • sqft
115 PARKSIDE DRIVE
5 bds • 2 ba • sqft
165 GALLEY AVENUE
6 bds • 5 ba • sqft
56 WRIGHT AVENUE
4 bds • 4 ba • 0 sqft
168 LANSDOWNE AVENUE
4 bds • 3 ba • sqft
353 ST CLARENS AVENUE
4 bds • 4 ba • sqft
343 INDIAN GROVE
7 bds • 4 ba • 0 sqft
323 BROCK AVENUE
5 bds • 2 ba • sqft
39 HUMBERSIDE AVENUE
2 bds • 0 ba • 2114 sqft
1600 QUEEN STREET W
Source: Realty.com
376 SUNNYSIDE AVENUE, Toronto (High Park Swansea), ON M6R2R8 in Toronto (High Park-Swansea), ON M6R2R8 is a other listed at $2,099,000. Highlights include 6 bedrooms, 4 bathrooms. Realty.ca has 32 photos, sales history, school insights, and mortgage tools for this listing.
Realty.com has 32 photos of 376 SUNNYSIDE AVENUE.
The full address for this home is 376 SUNNYSIDE AVENUE, Toronto (High Park Swansea), ON M6R2R8.
376 SUNNYSIDE AVENUE has been listed on Realty.com since Thu October 01, 2026
Daily errands do not require a car. World-class public transportation. Daily errands can be accomplished on a bike.
The average walkability score in the surrounding area is Walk Score: 80/100, Transit Score: 77/100, Bike Score: 75/100.
This content last refreshed on 2026-10-03 10:14:35. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.