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.
Address
27 Hillsboro Avenue
List Price
$1,799,000
MLS® Status
New
Expiration Date
2026-05-29
Property Type
Residential Freehold
Type of Dwelling
Duplex
Style of Home
2-Storey
Transaction Type
Sale
Area
Toronto C02
Sub-Area
Annex
Region
Toronto
Bedrooms
5 + 1
Bedrooms (Total)
6
Rooms Above Grade
11
Rooms Below Grade
4
Bathrooms
3
Floor Area
1500-2000 Sq. Ft.
Lot Depth
80
Lot Size Units
Feet
Lot Width
25
Parcel Number
211940410
Occupant Type
Owner+Tenant
Cross Street
Davenport and Avenue
Approx. Age
100+ Years
MLS® Number
C12870052
Listing Brokerage
ROYAL LEPAGE SIGNATURE REALTY
Basement Area
Apartment, Finished, Separate Entrance
Postal Code
M5R 1S6
Posession Details
Immediate
Parking
Mutual
Parking Places (Total)
2
Tax Amount
$10,173.00
Tax Year
2025
Site Influences
Awnings, Library, Park, Place Of Worship, Porch, Public Transit, Rec./Commun.Centre, School
Exterior Features
Awnings, Porch
Interior Features
In-Law Capability, Water Heater Owned
Property Features
Library, Park, Place Of Worship, Public Transit, Rec./Commun.Centre, School
Cable
Available
Central Vacuum
No
Family Room
No
Hydro
Yes
Ensuite Laundry
No
Special Designation
Unknown
Standard Status
Active
Board Or Association
Toronto Regional Real Estate Board
Heat Source
Gas
Heat Type
Water
Cooling Features
Window Unit(s)
Construction Materials
Brick
Direction Faces
South
Fireplace
Yes
Fireplace Features
Wood
Foundation Details
Concrete
Garage
No
Garage Type
None
Kitchens Total
3
Kitchens Above Grade
2
Kitchens Below Grade
1
Pool Features
None
Roof
Asphalt Rolled
Tax Legal Description
PT LT 5 PL 130 TORONTO AS IN CA755819; S/T & T/W CA755819; CITY OF TORONTO
View Type
Park/Greenbelt
Waterfront
No
Sewer
Sewer
Rooms
| Floor | Type | Dimensions | Features |
|---|---|---|---|
| Main | Living Room | 4.5 x 3.02 | Fireplace |
| Main | Dining Room | 4.5 x 3.02 | Window |
| Main | Kitchen | 2.88 x 2.28 | Window |
| Main | Bedroom | 3.19 x 2.52 | Window |
| Main | Bedroom 2 | 3.82 x 2.54 | Window |
| Upper | Living Room | 4.49 x 3 | Window |
| Upper | Dining Room | 2.79 x 2.65 | Window |
| Upper | Kitchen | 2.9 x 2.29 | |
| Upper | Primary Bedroom | 4.49 x 3 | Fireplace, W/O To Balcony |
| Upper | Bedroom 2 | 3.85 x 2.44 | Window |
| Upper | Bedroom 3 | 3.19 x 2.49 | Window |
| Lower | Living Room | 4.67 x 2.74 | Window |
| Lower | Kitchen | 3.95 x 2.78 | Eat-in Kitchen |
| Lower | Bedroom | 5.33 x 3.42 | Window |
| Lower | Utility Room | 6.35 x 2.99 | Combined w/Laundry, Window |
