27 Hillsboro Avenue Opportunity Meets Lifestyle in the Heart of Avenue & DavenportWelcome to a rare and versatile offering in one of Toronto's most coveted neighbourhoods. 27 Hillsboro Avenue is a duplex-zoned property with exceptional flexibility for investors, end-users, or visionaries looking to unlock long-term value in this century brick home. The home features a shared driveway with parking for two vehicles-a true bonus for this location. Main level freshly updated with new flooring, paint, and modern lighting. Lower level recently updated, new windows and water proofing.currently leased. Each upper level enjoys its own private porch and includes a sun porch, offering wonderful bonus family space, a home office, or a cozy reading retreatThe basement in-law suite currently leased.Laundry and utilities are shared, keeping operations straightforwardFrom a future-planning perspective, the options here are compelling:Keep the current duplex configuration with basement suite,Restore to a stunning single-family home (all stairways are intact),Upgrade or reposition the property to maximize its potentialAn initial zoning review indicates potential 6-plex compliance (buyers to confirm independently), making this an exciting prospect for those exploring gentle density and long-term development upside.All of this is wrapped in an unbeatable location: steps to Ramsden Park, minutes to Rosedale subway station, and a short walk to Yorkville, with its world-class dining, shopping, and culture.Live in it. Rent it. Reimagine it. This is a property that grows with your goals-and opportunities like this on Hillsboro Avenue don't come around often. Book your showing and explore the possibilities.
5 bedrooms, 3 bathrooms, about 1,500 sq ft, works out to roughly $1,186 per square foot. Chat with Zara if you'd like a deeper read on whether this duplex fits your budget and timing.
Inside 27 Hillsboro Ave
Every detail from the listing, in one place.
Type
Duplex
Style
2-Storey
Living space
1500-2000 sq ftas stated on the listing
Parking
2 spaces
Basement
Apartment, Finished
Features & systems
Parking & garage
Parking spaces
2
Interior
Basement
Apartment · Finished
Lot & land
Lot size (sqft)
0
Listing & possession
Property style
2-Storey
Property class
Duplex
27 Hillsboro 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® C14144160$1,779,000
Sourced from MLS®. Includes earlier listings of this property on record.
What's it worth?
How 27 Hillsboro 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 →
Referral disclosure: Summitly may refer you to Mortgage Squad Advisors, an affiliated mortgage partner. You are free to choose any lender or mortgage professional.
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
$8,740
/mo
based on the purchase price of $1,779,000
$355,800 cash
$1,423,200 financed
$1,198,708 total interest
Principal54%$1,423,200
Interest46%$1,198,708
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.
For homeowners nearby
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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 4–7 bed homes for sale in Toronto around $1.8M.
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 listings13,017Homes 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 27 Hillsboro Ave
How much is 27 Hillsboro Ave listed for?
27 Hillsboro Ave is listed at $1,779,000 (MLS® C14144160). Summitly updates the price as soon as the MLS® record changes.
Is $1,779,000 a good price for 27 Hillsboro Ave?
Summitly rates it Well Above Market: the asking price is 15% or more above 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 27 Hillsboro Ave changed?
No — 27 Hillsboro Ave is still listed at its original asking price of $1,779,000.
How many bedrooms and bathrooms does 27 Hillsboro Ave have?
27 Hillsboro Ave has 5 bedrooms and 3 bathrooms, with about 1,500–2,000 square feet of living space. It is a duplex in Toronto.
How much would the monthly mortgage be on 27 Hillsboro Ave?
About $8,740 a month — principal and interest on $1,779,000 with 20% down ($355,800), 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 27 Hillsboro Ave compare with other homes in Toronto?
Its asking price of $1,779,000 is about 111% 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 27 Hillsboro Ave been sold before?
Summitly has no earlier MLS® sale or lease of 27 Hillsboro Ave on record from the last two years. Older records aren't shown under TRREB rules.
Where is 27 Hillsboro Ave?
27 Hillsboro Ave is in Toronto, ON. Schools, transit, parks and shops nearby are under Location & lifestyle on this page.
How long has 27 Hillsboro Ave been on the market?
1 day — 27 Hillsboro Ave was listed on November 2, 2026.
What is the price per square foot of 27 Hillsboro Ave?
About $890 to $1,186 per square foot: the asking price of $1,779,000 over the 1,500–2,000 sq ft the listing gives as its size range.
Does 27 Hillsboro Ave have parking or a garage?
Yes — the listing gives 2 parking spaces.
Does 27 Hillsboro Ave have a basement, and is it finished?
The listing describes the basement as: Apartment, Finished.
