Offered for the first time in decades, this distinguished Wychwood/Regal Heights detach home presents a remarkable opportunity to own a property with its' original character and charm, generous in scale and full of possibilities. Situated just steps from St. Clair Avenue West, this home offers the flexibility to preserve its existing legal duplex(with 2 separate hydro meters) configuration as an income property or undertake a thoughtful restoration to create an exceptional single-family residence. From the classic solid brick and welcoming large covered front porch to hardwood floors, original wood trim, stained-glass details, elegant staircase, bay windows and wood-burning and gas fireplace, the home's architectural heritage is evident throughout. Generously proportioned principal rooms and multiple levels of living space provide an inviting foundation for a transformation that keeps the property's history while introducing the comforts and finishes of contemporary living. For investors, the existing duplex setup offers an opportunity to establish a rental strategy with potential for up to 4 units. For those with a vision for restoration, the home's layout and distinctive period details invite a spectacular reinvention as a substantial single-family residence. One-car detached garage with One-car parking on driveway & One on parking pad and private, tree-lined backyard add further versatility. Just moments from cafés, restaurants, shops and everyday conveniences of St. Clair Ave W, this home enjoys access to the cultural energy of nearby Corso Italia, easy access to Transit with Bus Stop across the street, Schools nearby and Yorkdale Shopping Centre and 401 Hwy access just a 15 min drive away. Whether you're looking for a smart investment or a chance to enter the market with built-in income potential, this property checks all the boxes. Live in one unit and rent the others, helping to build equity while enjoying all the benefits of home ownership.
6 bedrooms, 4 bathrooms, about 2,500 sq ft, works out to roughly $490 per square foot. Chat with Zara if you'd like a deeper read on whether this detached fits your budget and timing.
Inside 55 Oakwood Ave
Every detail from the listing, in one place.
Type
Detached
Style
2 1/2 Storey
Living space
2500-3000 sq ftas stated on the listing
Parking
3 spacesYes garage
Basement
Unfinished
Features & systems
Parking & garage
Garage
Yes
Parking spaces
3
Interior
Basement
Unfinished
Lot & land
Lot size (sqft)
0
Listing & possession
Property style
2 1/2 Storey
Property class
Detached
55 Oakwood Ave Price & Sale History
Earlier listings of this property, list-price changes, and the most recent annual property tax on the listing.
For saleListedThis listingMLS® C14142454$1,225,000
Sourced from MLS®. Includes earlier listings of this property on record.
What's it worth?
How 55 Oakwood Ave Compares to the Toronto Market
Zara compares it with recent sales of similar homes nearby. It's a guide, not an appraisal.
Independent mortgage broker · OAC · rates subject to change and underwritingMortgage Squad →
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Monthly cost
Enter a rate to see the monthly cost
An estimate, not a quote. Utilities and insurance are extra.
Affordability calculator
Estimated monthly payment
$6,018
/mo
based on the purchase price of $1,225,000
$245,000 cash
$980,000 financed
$825,417 total interest
Principal54%$980,000
Interest46%$825,417
20% down · 25-yr amortization · 5.50% rate. Principal & interest only — taxes, condo fees, and insurance not included.
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Figures are Summitly estimates for illustration only — not from TRREB or the MLS® feed, and not a mortgage approval, appraisal, or financial advice.
Rental income potential
Est. monthly rent
low–high
Gross yield
rent × 12 ÷ price
Cap rate (est.)
net of tax + fees
Summitly AI estimate for discussion only — not from TRREB or the MLS® feed, and not an appraisal or investment advice. Yield and cap rate are derived from the estimated rent versus the asking price.
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Mortgage financing is arranged through Mortgage Squad Advisors. Summitly is the technology platform that powers this site. Estimated values, AI insights, calculator results, and rental projections shown on this page are generated by Summitly and are not provided by, reviewed by, or sourced from TRREB, the MLS®, or the listing brokerage; they are not appraisals or opinions of value. The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by the Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The Coldwell Banker® name and logo are trademarks of Coldwell Banker Real Estate LLC.
Similar homes for sale nearby in Toronto
Other 5–8 bed homes for sale in Toronto around $1.2M.
Average days on market32Homes sold in about 32 days on average.
Sale-to-list ratio5121.8%On average, homes sold at or above asking.
Active listings12,629Homes for sale here right now.
Median vs prior 90 days−0.3%Compared with May 7 – Aug 5, 2026: prices down.
Based on 9,257 sales from Aug 5 – Nov 3, 2026 (7,087 in the prior 90 days). Aggregate MLS® figures for closed sales; individual sold prices are shown only to signed-in members.
Questions About 55 Oakwood Ave
How much is 55 Oakwood Ave listed for?
55 Oakwood Ave is listed at $1,225,000 (MLS® C14142454). Summitly updates the price as soon as the MLS® record changes.
Is $1,225,000 a good price for 55 Oakwood Ave?
Summitly rates it Excellent Deal: the asking price is 10% or more below Zara's estimate, an estimate built from recent sales in Toronto. The rating is an automated opinion, not an appraisal; "What's it worth?" on this page shows how it is worked out. See Zara's estimate
Has the price of 55 Oakwood Ave changed?
No — 55 Oakwood Ave is still listed at its original asking price of $1,225,000.
How many bedrooms and bathrooms does 55 Oakwood Ave have?
55 Oakwood Ave has 6 bedrooms and 4 bathrooms, with about 2,500–3,000 square feet of living space. It is a detached home in Toronto.
How much would the monthly mortgage be on 55 Oakwood Ave?
About $6,018 a month — principal and interest on $1,225,000 with 20% down ($245,000), a 25-year amortization and an assumed 5.5% interest rate. The mortgage calculator on this page lets you change the down payment, amortization and rate.
How does 55 Oakwood Ave compare with other homes in Toronto?
Its asking price of $1,225,000 is about 45% above the median sold price in Toronto over the last 90 days, $842,000, across 9,257 closed sales on the TRREB MLS®. A city median mixes every type and size of home, so the comparable sales on this page are the closer guide.
Has 55 Oakwood Ave been sold before?
Summitly has no earlier MLS® sale or lease of 55 Oakwood Ave on record from the last two years. Older records aren't shown under TRREB rules.
Where is 55 Oakwood Ave?
55 Oakwood Ave is in Toronto, ON. Schools, transit, parks and shops nearby are under Location & lifestyle on this page.
How long has 55 Oakwood Ave been on the market?
55 Oakwood Ave was listed today (November 3, 2026).
What is the price per square foot of 55 Oakwood Ave?
About $408 to $490 per square foot: the asking price of $1,225,000 over the 2,500–3,000 sq ft the listing gives as its size range.
Does 55 Oakwood Ave have parking or a garage?
Yes — the listing gives 3 parking spaces. Garage: Yes.
Does 55 Oakwood Ave have a basement, and is it finished?
The listing describes the basement as: Unfinished.
