27 Hillsboro Avenue

27 Hillsboro Avenue
27 Hillsboro Avenue
27 Hillsboro Avenue
1/1
5+1
 bed
3
 bath
2
 parking
1500 - 2000
 sqft
Duplex
$1,999,000
For Sale
1 hour
 on site
$1,999,000
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Size
-
Lot size
2000 sqft
Street frontage
-
Possession
2026-02-13
Price per sqft
$1,000 - $1,333
Taxes
$10,173 (2025)
Parking Type
-
Style
2-Storey
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Description
27 Hillsboro Avenue Opportunity Meets Lifestyle in the Heart of Ave & Dav. 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. The home features a shared (skinny) driveway with parking for two vehicles a true bonus for this location. The upper two units are vacant, 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 is currently rented at $1,650/month. Laundry and utilities are shared, keeping operations straight forward.From a future-planning perspective, the options here are compelling: Keep the current duplex configuration Restore to a stunning single-family home Upgrade or reposition the property to maximize its potential An initial zoning review by Property Pathways indicates potential 6-plex compliance (buyers t 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®#: C12722748
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:
Jan 22, 2026
Show all details
Rooms
LevelNameSizeFeatures
Lower
Utility Room
20.8 x 9.8 ft
Main
Dining Room
14.8 x 9.9 ft
Lower
Living Room
15.3 x 9.0 ft
Show all
Instant estimate:
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$40,764
lower than listed price
i
High
$2,028,072
Mid
$1,958,236
Low
$1,859,705
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About 27 Hillsboro Avenue

Located at 27 Hillsboro Avenue, this Toronto duplex is available for sale. It was listed at $1999000 in January 2026 and has 5+1 beds and 3 bathrooms. Situated in Toronto's Yorkville neighbourhood, Summerhill, Yonge and Bloor, The Annex and Casa Loma are nearby neighbourhoods.

Looking for your next favourite place to eat? There is a lot close to 27 Hillsboro Ave, Toronto.Grab your morning coffee at Black Camel located at 4 Crescent Rd. For grabbing your groceries, Paris Grocery is a 3-minute walk.

For those residents of 27 Hillsboro Ave, Toronto without a car, you can get around rather easily. The closest transit stop is a Bus Stop (Davenport Rd at Belmont St) and is only steps away connecting you to Toronto's public transit service. It also has route Bay nearby. Access to Don Valley Parkway from 27 Hillsboro Ave is within a few minutes drive, making it easy for those driving to get into and out of the city