13 days on market
$1,999,000
For Sale

27 Hillsboro Ave

Annex, Toronto

5+1 Bed|3+1 Bath|Yes|13 days on market

$1,999,000

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Home Details

Taxes
$848 / month
Total Parking Spots
2
Driveway
Mutual
Garage Spaces
NaN
Furnished
No
Lot Size
25 x 80 Feet
Move-in Date
Immediate
Building Age
100+ Years
Hydro Included
No
Heating
Water
Water Included
No
Kitchens
3
Family Room
Yes
Basement
Apartment, Finished
Fireplace
Y
Air Conditioning
Window Unit
Central Vaccum
No
Exterior
Brick
Sewer
Sewers
Property Type
Duplex
Style
2-Storey
Status
New
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Listing Description

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.
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.

Property History

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Rooms

Room dimensions for 27 Hillsboro Ave, Toronto
Living
15 x 10150 sqft
Dining
15 x 10150 sqft
Kitchen
9 x 763 sqft
Br
10 x 880 sqft
2nd Br
13 x 8104 sqft
Living
15 x 10150 sqft
Dining
9 x 981 sqft
Kitchen
10 x 880 sqft
Primary
15 x 10150 sqft
2nd Br
13 x 8104 sqft
3rd Br
10 x 880 sqft
Living
15 x 9135 sqft
Kitchen
13 x 9117 sqft
Br
17 x 11187 sqft
Utility
21 x 10210 sqft

Market Trends and Insights

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Your estimated monthly payment for 27 Hillsboro Ave is 10702

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Total Mortgage


Purchase Price$1999000
Down Payment$399800
Mortgage Insurance$0
Total Mortgage$1599200

Monthly Payment


Mortgage Payment$9855
Property Taxes$848
Maintenance Fees$0
Monthly Payment$10702
$10702
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About 27 Hillsboro Ave, Toronto

Located at 27 Hillsboro Ave , this Toronto house is available for sale. This property was listed for $1,999,000 on Thu Jan 22 2026. This house's size is 1500-2000 Sqft. It has 5 bedrooms and 3 bathrooms. The property includes the following rooms: Living, Dining, Kitchen, Br, 2nd Br, Living, Dining, Kitchen, Primary, 2nd Br, 3rd Br, Living, Kitchen, Br, Utility. This property comes with 2 parking spots. 27 Hillsboro Ave, Toronto is situated in the Annex neighbourhood.


MLS#: C12722748 · $1,999,000 · 5 bedroom house in Annex, Toronto