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27 Hillsboro Avenue
Annex Toronto M5R 1S6

$1,779,000
Residential Freehold beds: 5+1 baths: 3.0

Main Photo: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 1: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 2: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 3: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 4: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 5: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 6: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 7: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 8: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 9: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 10: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 11: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 12: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 13: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 14: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 15: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 16: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 17: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 18: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 19: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 20: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 21: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 22: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 23: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 24: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 25: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 26: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 27: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Photo 28: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C14144160
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
C14144160
Bedrooms:
5+1
Bathrooms:
3
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.
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:
Gas
Fireplaces:
2
Foundation:
Concrete
Roof:
Asphalt Rolled
Basement:
Apartment, Finished, Separate Entrance, Full
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 A/C units in place in main and upper unit. New boiler 2022, Hot water heater leased $30/month.
None
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:
Nov 03, 2026
Original Price:
Previous Price:
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    new windows for basement
Listed by ROYAL LEPAGE SIGNATURE REALTY
Data was last updated November 3, 2026 at 06:15 PM (UTC)
Carl Schuy
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