MLS® listing
27 Hillsboro Avenue: duplex for sale
$1,799,000
From the listing brokerage
27 Hillsboro Avenue Opportunity Meets Lifestyle in the Heart of Avenue & Davenport. Welcome 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. All units are vacant, The upper two units have been freshly updated with new flooring, paint, and modern lighting, and are move-in ready or easily rentable. Each upper level enjoys its own private porch, and both feature wood-burning fireplaces, adding warmth and character that tenants and homeowners love.The upper unit also includes a sun porch, offering wonderful bonus family space, a home office, or a cozy reading retreat.The basement in-law suite can be used to provide immediate income from day one. Laundry and utilities are shared, keeping operations straightforward. From 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 potential An initial zoning review by Property Pathways 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.
Facts on the listing
| Square feet | 1500-2000 |
|---|---|
| Approximate age | 100+ |
| Style | 2-Storey |
| Basement | Apartment, Finished, Separate Entrance |
| Lot width | 25 |
| Lot depth | 80 |
| Lot measured in | Feet |
| Faces | South |
| Parking spaces | 2 |
| Garage | None |
| Heating | Water |
| Cooling | Window Unit(s) |
| Kitchens | 3 |
| Property tax | $10,173 |
| Tax year | 2025 |
| Parking | Mutual |
| Interior features | In-Law Capability, Water Heater Owned |
| Features | Library, Park, Place Of Worship, Public Transit, Rec./Commun.Centre, School |
| View | Park/Greenbelt |
Listing courtesy of ROYAL LEPAGE SIGNATURE REALTY. MLS® C13437452.
About this duplex
27 Hillsboro Avenue is a 6 bedroom duplex in TRREB's Annex community in Toronto, listed for sale at $1,799,000. The listing shows 3 bathrooms and 1500-2000 square feet. The style is given as 2-storey. The lot is listed as 25 by 80 feet. The listing gives the basement as apartment, finished, separate entrance. It comes with 2 parking spaces according to the listing. The nearest main intersection given is Davenport and Avenue. The age is listed as 100+ years.
These details come from the listing brokerage through TRREB's MLS® System. Room sizes, the lot, the taxes and what is included in the sale should all be confirmed before an offer is firm.
What it costs to buy 27 Hillsboro Avenue
At the asking price of $1,799,000, a buyer pays two land transfer taxes on closing: the Ontario tax and the City of Toronto's municipal tax. Both apply to every home inside the City.
| Asking price | $1,799,000 |
|---|---|
| Ontario land transfer tax | $32,455 |
| Toronto municipal land transfer tax | $32,455 |
| Both taxes | $64,910 |
| First-time buyer relief, if you qualify | up to $8,475 |
| Minimum down payment | $359,800 |
The down payment figure is the federal minimum: 20 percent, because a home at $1.5 million or more cannot carry mortgage default insurance. A lender can ask for more. These figures use the asking price, so they change if you pay more or less. Legal fees, title insurance and adjustments are extra: ask your lawyer for a written quote. This is general information, not legal or tax advice. Confirm the figures with a lawyer or accountant. You can change the price in our land transfer tax calculator and our mortgage calculator.
What it costs to own each month
| Property tax (2025) | $10,173 a year, about $848 a month |
|---|
That is before a mortgage payment, home insurance and utilities. The listing shows no monthly maintenance fee, so upkeep of the building and the lot is the owner's own cost.
What to check before you make an offer
- Book a home inspection. An inspector looks at the roof, foundation, wiring, plumbing and heating. The listing gives the heating as water.
- Have a lawyer search the title. A title search shows mortgages, liens and easements registered against the property. Ask whether a survey exists and whether it matches the lot on the listing, 25 by 80 feet.
- Ask about permits. Ask which renovations had building permits and whether those permits were closed. The listing shows 3 kitchens. If there is a second unit, ask whether it meets the municipality's rules for one.
- Confirm what is included. Appliances, light fixtures and window coverings are included only if the agreement says so. Ask whether the water heater or furnace is rented.
- Get your financing in writing. A lender looks at the property tax and heating costs as well as the price.
- See it in person. The listing has a virtual tour, but photos do not show noise, light at different hours or the state of the street and the homes beside it.
Our first-time home buyer guide and our page for buyers walk through each step. This is general information, not legal advice. Confirm the details with a lawyer.
About The Annex
Heritage districts, apartment buildings along Bloor Street and two subway lines meeting at Spadina and St George. The Annex sells more condo apartments than houses by a wide margin.
Transit: Spadina and St George stations (Line 1 and Line 2), Bathurst and Bay stations (Line 2), Dupont station (Line 1), 510 Spadina and 511 Bathurst streetcars, 26 Dupont bus
| Property type | Median | Sales and average |
|---|---|---|
| All property types | $1,240,000 | 133 sales, average $1,660,517 |
| Detached | About $1,950,000 | 8 sales, average about $2,882,000 |
| Semi-detached | About $1,725,000 | 27 sales, average about $2,056,000 |
| Freehold townhouse (TRREB att/row/townhouse) | About $1,825,000 | 9 sales, average about $1,796,000 |
| Condo townhouse | About $1,260,000 | 7 sales, average about $1,649,000 |
| Condo apartment | About $858,000 | 82 sales, average about $1,397,000 |
Source: TRREB community housing market reports, as set out in the guide.
Questions about The Annex
What did homes sell for in The Annex in spring 2026?
TRREB recorded 133 sales from April to June 2026 with a median of $1,240,000 and an average of $1,660,517 across all property types. Condo apartments were 82 of those sales, with a median of about $858,000.
Is The Annex a good place to live if you want to use the subway?
For subway access it is well placed, with Spadina and St George stations serving both Line 1 and Line 2, plus Bathurst, Bay and Dupont stations at its edges. From Spadina station, Union station is 7 stops on Line 1.
Are there heritage rules on houses in The Annex?
Parts of it are in Heritage Conservation Districts, including East Annex (1994) and West Annex Phase 1 on Madison Avenue, with West Annex Phase II in development. Check with the City whether a specific address is inside a district before planning exterior changes.
Are most homes in The Annex houses or apartments?
Apartments. In the 2021 Census 54.5% of the 16,325 private dwellings were in buildings of five or more storeys and 27.8% in buildings under five storeys, while single-detached houses were 3.8%.
Where is the library in The Annex?
The Toronto Public Library Spadina Road branch is at 10 Spadina Road. The Toronto Reference Library at 789 Yonge Street is to the east.
Read the The Annex neighbourhood guide · All The Annex homes for sale
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Questions about 27 Hillsboro Avenue
How much is land transfer tax on 27 Hillsboro Avenue?
At the asking price of $1,799,000 the Ontario tax is $32,455 and the Toronto tax is $32,455, $64,910 in total. A first-time buyer who qualifies can get up to $8,475 back. Confirm the final figures with your lawyer.
What is the minimum down payment for 27 Hillsboro Avenue?
$359,800 at the asking price of $1,799,000, under the federal minimum down payment rules. A lender may require more.
How much is the property tax on 27 Hillsboro Avenue?
The listing shows $10,173 a year for 2025, about $848 a month.
How do I book a showing for 27 Hillsboro Avenue?
Use the form on this page or call us. Quote MLS® C13437452. We will confirm the listing is still available and arrange a time with the listing brokerage.
Is 27 Hillsboro Avenue still for sale?
This page is refreshed from TRREB's MLS® System through the day. If the listing sells or is withdrawn the page says so. Contact us to confirm before you make plans.
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