27 Hillsboro Avenue, Toronto

27 Hillsboro Avenue
27 Hillsboro Avenue
27 Hillsboro Avenue
+25
5+1
 bed
3
 bath
2
 parking
1500 - 2000
 sqft
Duplex
$1,779,000
For Sale
3 hours
 on site
$1,779,000
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Size
-
Lot size
2000 sqft
Street frontage
-
Possession
2026-12-01
Price per sqft
$890 - $1,186
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 & 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.
Broker: ROYAL LEPAGE SIGNATURE REALTY
MLS®#: C14144160
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:
Nov 3, 2026
Show all details
Rooms
LevelNameSizeFeatures
Upper
Primary Bedroom
14.7 x 9.8 ft
Lower
Kitchen
13.0 x 9.1 ft
Upper
Living Room
14.7 x 9.8 ft
Show all
Instant estimate:
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$199,429
lower than listed price
i
High
$1,635,903
Mid
$1,579,571
Low
$1,500,093
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About 27 Hillsboro Avenue

27 Hillsboro Avenue is a Toronto duplex for sale. 27 Hillsboro Avenue has an asking price of $1779000, and has been on the market since November 2026. This 1500-2000 sqft duplex has 5+1 beds and 3 bathrooms. 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 Lemon Lily Organic Tea located at 184 Davenport Rd. Nearby grocery options: Paris Grocery is a 3-minute walk.

Living in this Yorkville duplex is easy. There is also Davenport Rd at Belmont St Bus Stop, only steps away, with 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