376 Sunnyside Avenue, Toronto W01

Price: $2,099,000

6 bedrooms, 4 bathrooms

2,000 - 2,499 sqft

Property Type: Detached

MLS#: W13846418

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.

376 Sunnyside Avenue - Detached photo 1 of 32 in High Park / Junction / Roncesvalles, Ontario
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376 Sunnyside Avenue - Detached photo 31 of 32 in High Park / Junction / Roncesvalles, Ontario
376 Sunnyside Avenue - Detached photo 32 of 32 in High Park / Junction / Roncesvalles, Ontario
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New Listing
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$2,099,000 - 376 Sunnyside Avenue, High Park

Detached for Sale in High Park

New — Listed 7 days ago

Neighbourhood: High Park-Swansea

6Beds
4Baths
2,000 - 2,499Sq Ft
Detached

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Property Details
MLS Number
W13846418
Property Type
Detached
Status
active
Days on Site
7
Bedrooms
6
Bathrooms
4
Square Feet
2,000 - 2,499 sqft
Neighbourhood
High Park / Junction / Roncesvalles
Taxes (2025)
$10,271
Listing Brokerage
SOTHEBY'S INTERNATIONAL REALTY CANADA
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. 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.

Mortgage Calculator

Estimate your monthly payments for this property

Estimated Payment

$9,284.58/mo

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5-yr fixed avg.

Principal: $1,679,200Interest: $1,106,175
Mortgage Amount$1,679,200
Total Interest$1,106,175
Est. Property Tax$1,487/mo
Total Cost$2,785,375

Rates shown are estimates based on typical Ontario 5-year fixed rates. Canadian mortgages use semi-annual compounding as required by law. CMHC insurance applies to purchases under $1.5M with less than 20% down. Estimated property tax uses an approximate 0.85% rate. Contact us for current rate options and pre-approval.

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Neighbourhood Guide: High Park-Swansea

Discover High Park-Swansea

High Park-Swansea is a vibrant community in the Greater Toronto Area, offering excellent amenities, schools, and transportation options. This area is popular with families and professionals seeking a balanced lifestyle with access to urban conveniences and natural spaces.

Why Live in High Park-Swansea

  • •Convenient location in High Park / Junction / Roncesvalles
  • •Access to local shops and dining
  • •Good public transit connections
  • •Community parks and green spaces
  • •Well-maintained neighbourhoods

Nearby Schools

Local Elementary SchoolPublic Elementary
Local Secondary SchoolPublic High School

Transit & Commuting

  • •MiWay bus routes throughout the area
  • •GO Transit stations within driving distance
  • •Easy highway access to 401/403/QEW
  • •Walking distance to local amenities

Parks & Amenities

  • •Local parks and recreational facilities
  • •Community centres
  • •Shopping plazas nearby
  • •Restaurants and cafes

Lifestyle & Community

High Park-Swansea offers a wonderful quality of life with a mix of residential charm and urban convenience. Residents enjoy easy access to schools, parks, and shopping, making it an ideal location for families and professionals alike.

70
Walk Score
Varies
Price Range

376 Sunnyside Avenue, High Park / Junction / Roncesvalles

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Investor Analysis

Rental income estimator & ROI calculator

Estimated Monthly Rent
$4,100/mo
Range: $3,485 - $4,715
Cap Rate (ROI)
1.2%
Below Average

Monthly Cash Flow Breakdown

Rental Income+$4,100
Maintenance Fees-$0
Property Tax (est.)-$1,487
Insurance (est.)-$437
Net Cash Flow+$2,176

Note: These are estimates only. Actual figures may vary based on market conditions, property condition, and other factors. Consult with a financial advisor for personalized advice.

Joe Battaglia - Top Real Estate Agent in Mississauga, REMAX Realty Specialists

Joe's Thoughts

Honest perspective from 30+ years of GTA real estate experience

Fair Market Value

At $1050/sqft, this property is priced in line with current High Park market conditions. The pricing suggests the seller has done their homework. We may have modest room for negotiation, typically 2-4% in today's market.

Just Listed - Act Strategically

This property hit the market within the last week. In High Park's current market, desirable homes often receive multiple offers within 5-7 days. If you're seriously interested, I recommend booking a showing immediately. However, never let urgency override due diligence - we'll still do proper inspections.

Detached Home Advantages

Detached homes in High Park are increasingly scarce and valuable. You'll have no shared walls, full control over renovations, and typically stronger appreciation. Consider the lot size and potential for future additions or basement apartment income. Detached homes also offer the most flexibility for growing families.

Excellent Flexibility

With 6 bedrooms, you have genuine flexibility. Beyond the master and kids' rooms, you can have a dedicated home office, guest room, hobby space, or even rental income potential. In today's work-from-home era, extra bedrooms add significant value. Properties with 5+ bedrooms are relatively rare in High Park.

Bathroom Count Matters

With 4 bathrooms, morning routines are much smoother. Multiple bathrooms significantly improve daily livability and are a major selling point for resale. Buyers consistently pay more for adequate bathroom counts - this is a strong feature.

About High Park-Swansea

I know High Park-Swansea well from working with many buyers and sellers here. Each pocket has its own character - let me share what I've learned about this specific street and block. During our showing, I'll point out local amenities, school catchments, and what similar homes have sold for recently.

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