Forgot password Extend Verify Contact

27 Hillsboro Avenue
Annex Toronto M5R 1S6

$1,999,000
Residential Freehold beds: 5+1 baths: 3.0

Summer view street
Photo 1: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 2: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 3: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 4: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 5: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 6: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 7: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 8: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 9: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 10: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 11: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 12: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 13: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 14: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 15: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 16: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 17: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 18: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 19: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 20: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 21: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 22: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 23: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 24: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 25: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 26: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Photo 27: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
C12722748
Bedrooms:
5+1
Bathrooms:
3
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.
Under Contract:
Hot Water Heater
Property Type:
Residential Freehold
Property Sub Type:
Duplex
Home Style:
2-Storey
Approx. Age:
100+
Total Approx Floor Area:
1500-2000
Lot Depth:
80'
Lot Frontage:
25'
Direction Faces:
South
Bedrooms:
5+1
Bathrooms:
3.0
Water supply:
Municipal
Kitchens:
3
Kitchens in Basement:
1
Bedrooms Above Grade:
5
Bedrooms Below Grade:
1
Kitchens Above Grade:
2
Rooms Above Grade:
11
Rooms Below Grade:
4
Heating type:
Water
Heating Fuel:
Propane
Fireplaces:
2
Foundation:
Concrete
Roof:
Asphalt Rolled
Basement:
Apartment, Finished, Separate Entrance
Fireplace Features:
Wood
Fireplace/Stove:
Yes
Garage:
None
Garage Spaces:
0.0
Parking Features:
Mutual
Parking Spaces:
0
Total Parking Spaces:
2.0
Family Room:
No
Possession Details:
Immediate
Pool:
None
HST Applicable To Sale Price:
Included In
Taxes:
$10,173 / 2025
Assessment:
$- / -
Toronto
Toronto C02
Annex
Library, Park, Place Of Worship, Public Transit, Rec./Commun.Centre, School
In-Law Capability, Water Heater Owned
Awnings, Porch
Hot water heater
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 unit a/c units in place in upper unit. Main level units stored in basement area. New boiler 2022 Hot water heater leased $30/month.
Tenant property.
Brick
Park/Greenbelt
Floor
Type
Size
Other
Main
Living Room
14'9" × 9'11"
Fireplace
Main
Dining Room
14'9" × 9'11"
Window
Main
Kitchen
9'5" × 7'5¾"
Window
Main
Bedroom
10'6" × 8'3¼"
Window
Main
Bedroom 2
12'6" × 8'4"
Window
Upper
Living Room
14'8¾" × 9'10"
Window
Upper
Dining Room
9'2" × 8'8"
Window
Upper
Kitchen
9'6" × 7'6"
Upper
Primary Bedroom
14'8¾" × 9'10"
Fireplace, W/O To Balcony
Upper
Bedroom 2
12'8" × 8'
Window
Upper
Bedroom 3
10'6" × 8'2"
Window
Lower
Living Room
15'4" × 9'
Window
Lower
Kitchen
12'11½" × 9'1½"
Eat-in Kitchen
Lower
Bedroom
17'6" × 11'3"
Window
Lower
Utility Room
20'10" × 9'10"
Combined w/Laundry, Window
Utilities Cable:
Available
Utilities Telephone:
Available
Utilities Gas:
Yes
Utilities Hydro:
Yes
Utilities Water:
Yes
Sewers:
Yes
Special Designation:
Unknown
Sewers:
Sewer
Air Conditioning:
Window Unit(s)
Central Vacuum:
No
Seller Property Info Statement:
No
Date Listed:
Jan 22, 2026
Original Price:
Previous Price:
  • Photo 1: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Summer view street
  • Photo 2: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Front Street view
  • Photo 3: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Entrance
  • Photo 4: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Front porch Main level
  • Photo 5: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    View of Ramsden Park Lv 1
  • Photo 6: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Main Bath level 1
  • Photo 7: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Bedroom Lv 1
  • Photo 8: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Primary Level 2
  • Photo 9: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Bedroom Upper
  • Photo 10: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Shared drive
  • Photo 11: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Kitchen Lv 1
  • Photo 12: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Living/Dining Lv 1
  • Photo 13: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Primary w/FP Lv 2
  • Photo 14: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Lv 1 living and Dining
  • Photo 15: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Level 1 Living
  • Photo 16: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Level 1 Dining
  • Photo 17: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    View of Park Level 2
  • Photo 18: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Reae entrance to In-Law suite
  • Photo 19: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Rear Parking 2 vehicles
  • Photo 20: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Rear Parking
  • Photo 21: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Entry stairs for upper level
  • Photo 22: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Sunroom/dining Lv 2
  • Photo 23: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Sunroom/ dining 2 of 2
  • Photo 24: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Upper Level Porch
  • Photo 25: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Upper level Bath
  • Photo 26: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Upper Level Kitchen
  • Photo 27: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12722748
    Upper Level Porch 2
Listed by ROYAL LEPAGE SIGNATURE REALTY
Data was last updated January 23, 2026 at 04:15 PM (UTC)
EVA GOODING
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.