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. (id:2493)
Property Type:
Multi-family
Property Attached:
Yes
Living Area (Min):
1,500 sq. ft.139 m2
Living Area (Max):
2,000 sq. ft.186 m2
Taxes:
$10,173 /
-
Community:
Annex
Features:
Fireplace(s)
Exterior Features:
Brick
Community Features:
Community Centre
Structure Type:
Duplex
Utilities:
Sewer, Electricity, Cable
Appliances Included:
All, Window Coverings, Water Heater
Bedrooms:
6
Bedrooms Above Grade:
5
Bedrooms Below Grade:
1
Bathrooms:
3.0
Cooling:
Window air conditioner
Fireplace:
Yes
Fireplaces:
2
Foundation:
Concrete
Heating:
Natural gas
# Storeys:
2.0
Water:
Municipal water
Sewer:
Sanitary sewer
Basement:
Finished, Full, Apartment in basement, Separate entrance, N/A
Data was last updated November 3, 2026 at 07:45 PM (UTC)
Area Statistics
Listings on market:
11
Avg list price:
$2,700,000
Min list price:
$1,299,000
Max list price:
$5,999,000
Avg days on market:
30
Min days on market:
4
Max days on market:
138
Avg price per sq.ft.:
$651.45
These statistics are generated based on the current listing's property type
and located in
Annex. Average values are
derived using median calculations. This data is not produced by
the MLS® system.
The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are member’s of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.