27 Hillsboro Avenue, Toronto, ON M5R 1S6
Annex, Toronto · Near Davenport and Avenue · View map
About this home
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.
The home
- Type
- Duplex
- Style
- 2-Storey
- Square footage
- 1500-2000 sq ft
- Bedrooms
- 5
- Basement bedrooms
- 1
- Bathrooms
- 3
- Kitchens
- 3
- Rooms
- 11
- Basement
- Apartment, Finished, Separate Entrance, Full
- Lot size
- 25 x 80 ft
- Faces
- South
- View
- Park/Greenbelt
- Approximate age
- 100+ years
Ownership & fees
- Ownership
- Freehold
- Monthly condo fee
- None
- Exterior
- Brick
Heating & cooling
- Heating fuel
- Gas
- Heating type
- Water
- Air conditioning
- Window Unit(s)
- Fireplace
- Yes
Garage & parking
- Total parking
- 2
- Parking features
- Mutual
Taxes & other
- Property taxes
- $10,173/yr
- Tax year
- 2025
- Occupancy
- Tenant
- Possession
- Immediate
- Cross street
- Davenport and Avenue
- Neighbourhood
- Annex
More
- Price per sq ft
- ~$1,017 (at 1,750 sq ft)
- MLS® number
- C14144160
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The home and its surroundings
- In-Law Capability
- Water Heater Owned
- Library
- Park
- Place Of Worship
- Public Transit
- Rec./Commun.Centre
- School
- Awnings
- Porch
- Mortgage
- Property tax
- Maintenance fee
Cash needed to close
Estimates only, using Canadian semi-annual compounding, Ontario land transfer tax and Toronto municipal land transfer tax. Mortgage default insurance is added when you put down less than 20%. Your lender and lawyer will confirm exact numbers.
27 Hillsboro Avenue, Toronto, ON M5R 1S6
Annex, Toronto · Near Davenport and Avenue
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Listing history for 27 Hillsboro Avenue
See what this home and others at the same address were listed for, what they sold for, and how long it took.
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Frequently asked questions about 27 Hillsboro Avenue
Answers come straight from this home’s MLS® listing.
How much is 27 Hillsboro Avenue listed for, and what would it cost each month?
27 Hillsboro Avenue is listed for $1,779,000. With 20% down ($355,800), the mortgage payment would be roughly $7,176 a month at 4.5% over 30 years. Add property tax and the estimate comes to about $8,024 a month, all in. That figure is an illustration, not a quote.
Is 27 Hillsboro Avenue freehold or a condo, and is there a monthly fee?
27 Hillsboro Avenue is a duplex in Annex, Toronto. Ownership is freehold: you own the home and the lot. There is no monthly condo fee, so the roof, windows, driveway, snow and lawn are yours to look after.
How many bedrooms and bathrooms does 27 Hillsboro Avenue have?
27 Hillsboro Avenue has 5 bedrooms, plus 1 more bedroom in the basement, and 3 bathrooms. The listing gives the style as 2-storey.
Does 27 Hillsboro Avenue have a garage and parking?
The listing does not show a garage. In total the listing counts 2 parking spaces.
Does 27 Hillsboro Avenue have a finished basement?
The listing describes the basement as apartment, finished, separate entrance, full. It counts 1 bedroom on that level. Finished basement space is usually not counted in the square footage shown. A listing description is not proof of a legal second unit, so confirm zoning and permits with the municipality before counting on rental income.
What style of home is 27 Hillsboro Avenue?
27 Hillsboro Avenue is a duplex. A multiplex holds two or more separate units under one roof, often bought to live in one unit and rent the others.
How big is 27 Hillsboro Avenue, and what is the lot size?
The listing puts the home between 1,500 and 2,000 sq ft. The board reports a range rather than an exact figure, and it usually leaves out the basement. The lot is listed as 25 x 80 ft.
How is 27 Hillsboro Avenue heated and cooled?
Heating is water (gas). Cooling is window unit(s).
What are the property taxes for 27 Hillsboro Avenue?
Property taxes are $10,173 a year (2025), or about $848 a month.
Where is 27 Hillsboro Avenue?
27 Hillsboro Avenue is in the Annex community of Toronto. The nearest main intersection is Davenport and Avenue. The postal code is M5R 1S6.
Is 27 Hillsboro Avenue still for sale?
Yes. It is an active listing (MLS® C14144160). Listings here update from the board through the day and come down once a home sells.
What are similar properties near 27 Hillsboro Avenue asking?
Similar properties for sale nearby right now include 320 Brunswick Avenue at $1,699,000 (4+1 bed), 35 Dupont Street at $1,999,999 (4 bed) and 301 Dupont Street at $1,299,000 (3+1 bed). These are asking prices, not sold prices. The Sold history tab shows what homes at this address went for.
What have homes at 27 Hillsboro Avenue sold for?
Recent sales, leases and expired listings for this home and others at the same address are in the Sold history tab, with the price and date of each. It is free for members.
How do I book a showing at 27 Hillsboro Avenue?
Pick a day and time with Book a Tour on this page. Tours are free, with no obligation, in person or by video. You can also call or text 647-931-3923.
Have a different question? Ask about this home and get an answer, usually within the hour.
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Listing information comes from the Toronto Regional Real Estate Board through PropTx and is deemed reliable but is not guaranteed accurate. It is provided for consumers' personal, non-commercial use. 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.
*Estimated monthly cost assumes 20% down, a 4.5% rate and a 30-year amortization, plus property tax. For illustration only.