376 Sunnyside Avenue photo 1
376 Sunnyside Avenue photo 2
376 Sunnyside Avenue photo 3
376 Sunnyside Avenue photo 4
376 Sunnyside Avenue photo 5
376 Sunnyside Avenue photo 6
376 Sunnyside Avenue photo 7
376 Sunnyside Avenue photo 8
376 Sunnyside Avenue photo 9
376 Sunnyside Avenue photo 10
376 Sunnyside Avenue photo 11
376 Sunnyside Avenue photo 12
376 Sunnyside Avenue photo 13
376 Sunnyside Avenue photo 14
376 Sunnyside Avenue photo 15
376 Sunnyside Avenue photo 16
376 Sunnyside Avenue photo 17
376 Sunnyside Avenue photo 18
376 Sunnyside Avenue photo 19
376 Sunnyside Avenue photo 20
376 Sunnyside Avenue photo 21
376 Sunnyside Avenue photo 22
376 Sunnyside Avenue photo 23
376 Sunnyside Avenue photo 24
376 Sunnyside Avenue photo 25
376 Sunnyside Avenue photo 26
376 Sunnyside Avenue photo 27
376 Sunnyside Avenue photo 28
376 Sunnyside Avenue photo 29
376 Sunnyside Avenue photo 30
376 Sunnyside Avenue photo 31
376 Sunnyside Avenue photo 32

376 Sunnyside Avenue

High Park-Swansea / Toronto W01, ON M6R 2R8

NewActiveFor Sale
6 Beds
4 Baths
2,000 Sq Ft
Multi-Family
Virtual Tour Available

About This Property

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.

Property Details

StatusActive
Property TypeMulti-Family
Listing TypeFor Sale
Interior Size2,000 sq ft
Bedrooms6
Bathrooms4
ListedJuly 1, 2026
Postal CodeM6R 2R8

Features & Amenities

  • View
  • Fireplace
  • Air Conditioning
  • Basement

TRREB MLS® Attribution

MLS® W13509134

Listed by SOTHEBY'S INTERNATIONAL REALTY CANADA

The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA. The trademarks REALTOR®, REALTORS® and the REALTOR® logo are controlled by CREA and identify real estate professionals who are members of CREA. Listing data provided by the Toronto Regional Real Estate Board (TRREB). The information contained herein is from sources believed to be reliable but is not guaranteed. Information deemed reliable but not guaranteed accurate by TRREB or Team Filipe / RE/MAX.

$2,199,000

asking price

MLS®W13509134
TypeMulti-Family
CityToronto W01
← Back to Search

Team Filipe · RE/MAX · (647) 210-6070

Mortgage Estimate

Est. Monthly Payment

$10,738

/month · $1,759,200 mortgage

Down Payment20% — $439,800
Interest Rate5.5%

Amortization

Total Interest

$1,462,202

Total Cost

$3,221,402

Estimate only. Based on Canadian semi-annual compounding, 25-yr amortization at 5.5%.

Full Mortgage Calculator →

Listed By

SOTHEBY'S INTERNATIONAL REALTY CANADA