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27 Hillsboro Avenue in Toronto for sale

Asking price
$1,779,000
Estimate (Nov 03)
$1,710,000
MLS #:
C14144160
Type:
Duplex, 2-Storey
Approx. SQFT:
1500-2000
Basement:
Apartment, Finished
5+1 5+1
25 x 80 ft lot
PROPERTY HISTORY
SIGN IN REQUIRED
List Date List Price Last Status Sold Date Sold Price Days On Market
0000-00-00 $00000 New N/A N/A N/A
0000-00-00 $00000 Ter N/A N/A N/A
0000-00-00 $00000 Lsd Jul 31 $1,650
0000-00-00 $00000 Ter N/A N/A N/A
0000-00-00 $00000 Lsd May 11 $3,300
0000-00-00 $00000 Ter N/A N/A N/A
0000-00-00 $00000 Ter N/A N/A N/A
0000-00-00 $00000 Ter N/A N/A N/A
0000-00-00 $00000 Ter N/A N/A N/A
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.

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  • Date Listed: Monday, November 02, 2026
  • Listing Brokerage: Royal Lepage Signature Realty - Disclaimer: The information contained in this listing has not been verified by Royal Lepage Signature Realty and should be verified by the buyer.
  • Virtual Tour: View Virtual Tour for 27 Hillsboro Avenue
  • City: Toronto

    More 5 bedrooms homes for sale in Toronto

  • Neighbourhood: Annex
  • Major Intersection: Davenport and Avenue
  • Full Address: 27 Hillsboro Avenue, Toronto, M5R 1S6, Canada, ON, Canada
  • Living Room: Fireplace
  • Kitchen: Window
  • Living Room: Window
  • Kitchen:
  • Living Room: Window
  • Kitchen: Eat-In Kitchen
  • Amenities:
  • Taxes: $10,173.00 (2025)
Living15 x 10 ft150 sq ft
Dining15 x 10 ft150 sq ft
Kitchen9 x 7 ft63 sq ft
Br10 x 8 ft80 sq ft
2nd Br13 x 8 ft104 sq ft
Living15 x 10 ft150 sq ft
Dining9 x 9 ft81 sq ft
Kitchen10 x 8 ft80 sq ft
Primary15 x 10 ft150 sq ft
2nd Br13 x 8 ft104 sq ft
3rd Br10 x 8 ft80 sq ft
Living15 x 9 ft135 sq ft
Kitchen13 x 9 ft117 sq ft
Br17 x 11 ft187 sq ft
Utility21 x 10 ft210 sq ft

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WHAT'S YOUR HOME WORTH?

Click here to get an instant estimate and track its value over time.