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NEXT Open House + more
Mar 14, 2026 02:00 PM - 04:00 PM EDT

27 Hillsboro Avenue
Annex Toronto M5R 1S6

$1,799,000
Residential Freehold beds: 5+1 baths: 3.0

Main Photo: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 1: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 2: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 3: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 4: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 5: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 6: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 7: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 8: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 9: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 10: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 11: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 12: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 13: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 14: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 15: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 16: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 17: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 18: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 19: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 20: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 21: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 22: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 23: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 24: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 25: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 26: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 27: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 28: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 29: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 30: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 31: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 32: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 33: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 34: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 35: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 36: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Photo 37: 27 Hillsboro Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12870052
Open House - Mar 14, 2026
02:00 PM - 04:00 PM EDT
NOTES: Open House on Saturday, March 14, 2026 2:00PM - 4:00PM
Open House - Mar 15, 2026
02:00 PM - 04:00 PM EDT
NOTES: Open House on Sunday, March 15, 2026 2:00PM - 4:00PM
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
C12870052
Bedrooms:
5+1
Bathrooms:
3
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. The 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 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.
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
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 upper unit. Main level units stored in basement area. 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:
Mar 11, 2026
Original Price:
Previous Price:
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Virtual Tour

Listed by ROYAL LEPAGE SIGNATURE REALTY
Data was last updated March 11, 2026 at 06:15 PM (UTC)
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