27 Hillsboro Avenue

27 Hillsboro Avenue
27 Hillsboro Avenue
27 Hillsboro Avenue
+34
5+1
 bed
3
 bath
2
 parking
1500 - 2000
 sqft
Duplex
$1,799,000
For Sale
30 days
 on site
$1,799,000
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Size
-
Lot size
2000 sqft
Street frontage
-
Possession
2026-03-31
Price per sqft
$900 - $1,199
Taxes
$10,173 (2025)
Parking Type
-
Style
2-Storey
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Description
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.
Broker: ROYAL LEPAGE SIGNATURE REALTY
MLS®#: C12870052
Property details
Parking:
2
Parking type:
-
Property type:
Duplex
Heating type:
Water
Style:
2-Storey
MLS Size:
1500-2000 sqft
Lot front:
25 Ft
Lot depth:
80 Ft
Listed on:
Mar 11, 2026
Show all details
Rooms
LevelNameSizeFeatures
Lower
Kitchen
13.0 x 9.1 ft
Lower
Bedroom
17.5 x 11.2 ft
Lower
Living Room
15.3 x 9.0 ft
Show all
Instant estimate:
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$122,989
lower than listed price
i
High
$1,735,781
Mid
$1,676,011
Low
$1,591,680
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About 27 Hillsboro Avenue

27 Hillsboro Avenue is a Toronto duplex for sale. It has been listed at $1799000 since March 2026. This duplex has 5+1 beds, 3 bathrooms and is 1500-2000 sqft. 27 Hillsboro Avenue resides in the Toronto Yorkville neighbourhood, and nearby areas include Summerhill, Yonge and Bloor, The Annex and Casa Loma.

Some good places to grab a bite are Joso's, Subway or The Rebel House. Venture a little further for a meal at one of Yorkville neighbourhood's restaurants. If you love coffee, you're not too far from Black Camel located at 4 Crescent Rd. Nearby grocery options: Paris Grocery is a 3-minute walk.

Transit riders take note, 27 Hillsboro Ave, Toronto is only steps away to the closest public transit Bus Stop (Davenport Rd at Belmont St) with route Bay. For drivers, the closest highway is Don Valley Parkway and is within a few minutes drive from 27 Hillsboro Ave, making it easier to get into and out of the city