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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.
Inclusions
All appliances where located in as is conditions. All ELF's and window covering where they exist. W/D in basement (new 2024/25) Window A/C units in place in main and upper unit. New boiler 2022, Hot water heater leased $30/month.
Exclusions
None
Broker
ROYAL LEPAGE SIGNATURE REALTY
Neighbourhood
Annex
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Duplex
27 Hillsboro Avenue Toronto
Annex
Built
100+
Type
Duplex
Basement
Apartment, Finished, Separate Entrance, Full
Parking
None (2)
Property Tax
~$10,173/yr
Heating
Water
Buying Essentials
Square Feet
1750 sqft
Facing Direction
South
Parking
None (2)
Finances
List Price
$1,779,000
Price per SQFT
$1,017/sqft
Property Tax
~$10,173/yr
Property Specs
Property Type
Duplex
MLS Size
1750 sqft
Age of Building
100+
Basement
Apartment, Finished, Separate Entrance, Full
Living & Amenities
Heating Type
Water
Features
In-Law Capability · Water Heater Owned
Policies & Utilities
Neighbourhood
Annex
Listed On
Nov 2, 2026
Library
Park
Place Of Worship
Public Transit
Rec./Commun.Centre
School
Days on Market
Current: 5 days
Fireplace
14.8 x 9.9
146 sqft
Window
14.8 x 9.9
146 sqft
Window
9.4 x 7.5
71 sqft
Window
10.5 x 8.3
87 sqft
Window
12.5 x 8.3
104 sqft
Window
14.7 x 9.8
145 sqft
Window
9.2 x 8.7
80 sqft
9.5 x 7.5
71 sqft
Fireplace, W/O To Balcony
14.7 x 9.8
145 sqft
Window
12.6 x 8.0
101 sqft
Window
10.5 x 8.2
85 sqft
Window
15.3 x 9.0
138 sqft
Eat-in Kitchen
13.0 x 9.1
118 sqft
Window
17.5 x 11.2
196 sqft
Combined w/Laundry, Window
20.8 x 9.8
204 sqft
Rooms
15
Listed Room Area
1,837 sqft
Source
Estimated from MLS room dimensions
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