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27 HILLSBORO AVENUE
Annex Toronto (Annex) M5R 1S6

$1,999,000
Multi-family beds: 6 baths: 3.0

Summer view street
Photo 1: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 2: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 3: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 4: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 5: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 6: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 7: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 8: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 9: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 10: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 11: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 12: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 13: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 14: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 15: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 16: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 17: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 18: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 19: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 20: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 21: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 22: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 23: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 24: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 25: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 26: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Photo 27: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
Status:
Active
Prop. Type:
Multi-family
MLS® Num:
C12722748
Bedrooms:
6
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. (id:2493)
Property Type:
Multi-family
Property Attached:
Yes
Living Area (Min):
1,500 sq. ft.
Living Area (Max):
2,000 sq. ft.
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
# Storeys:
2.0
Water:
Municipal water
Sewer:
Sanitary sewer
Basement:
Finished, Apartment in basement, Separate entrance, N/A
Lot Frontage:
25'
Lot Details:
25 x 80 FT
Parking:
No Garage
Total Parking Spaces:
2
Floor
Type
Size
Other
Lower level
Living room
15'4" × 9'
-
Lower level
Kitchen
12'11½" × 9'1½"
-
Lower level
Bedroom
17'6" × 11'3"
-
Lower level
Utility room
20'10" × 9'10"
-
Main level
Living room
14'9" × 9'11"
-
Main level
Dining room
14'9" × 9'11"
-
Main level
Kitchen
9'5" × 7'5¾"
-
Main level
Bedroom
10'6" × 8'3¼"
-
Main level
Bedroom 2
12'6" × 8'4"
-
Upper Level
Bedroom 3
10'6" × 8'2"
-
Upper Level
Living room
14'8¾" × 9'10"
-
Upper Level
Dining room
9'2" × 8'8"
-
Upper Level
Kitchen
9'6" × 7'6"
-
Upper Level
Primary Bedroom
14'8¾" × 9'10"
-
Upper Level
Bedroom 2
12'8" × 8'
-
  • Photo 1: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Summer view street
  • Photo 2: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Front Street view
  • Photo 3: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Entrance
  • Photo 4: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Front porch Main level
  • Photo 5: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    View of Ramsden Park Lv 1
  • Photo 6: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Main Bath level 1
  • Photo 7: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Bedroom Lv 1
  • Photo 8: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Primary Level 2
  • Photo 9: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Bedroom Upper
  • Photo 10: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Shared drive
  • Photo 11: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Kitchen Lv 1
  • Photo 12: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Living/Dining Lv 1
  • Photo 13: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Primary w/FP Lv 2
  • Photo 14: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Lv 1 living and Dining
  • Photo 15: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Level 1 Living
  • Photo 16: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Level 1 Dining
  • Photo 17: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    View of Park Level 2
  • Photo 18: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Reae entrance to In-Law suite
  • Photo 19: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Rear Parking 2 vehicles
  • Photo 20: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Rear Parking
  • Photo 21: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Entry stairs for upper level
  • Photo 22: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Sunroom/dining Lv 2
  • Photo 23: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Sunroom/ dining 2 of 2
  • Photo 24: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Upper Level Porch
  • Photo 25: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Upper level Bath
  • Photo 26: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Upper Level Kitchen
  • Photo 27: 27 HILLSBORO AVENUE in Toronto (Annex): Multi-family for sale : MLS®# C12722748
    Upper Level Porch 2
Listed by ROYAL LEPAGE SIGNATURE REALTY
Data was last updated January 23, 2026 at 08:45 PM (UTC)
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