Proudly Canadian

This Property Is No Longer Available

Looking for similar properties? We can help you find your perfect home.

Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 1 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 2 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 3 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 4 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 5 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 6 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 7 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 8 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 9 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 10 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 11 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 12 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 13 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 14 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 15 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 16 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 17 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 18 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 19 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 20 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 21 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 22 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 23 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 24 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 25 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 26 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 27 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 28 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 29 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 30 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 31 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 32 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 33 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 34 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 35 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 36 of 37
Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 37 of 37
1 / 37• 34 locked
View on map
Inactive

$1,799,000

27 Hillsboro Ave

Toronto C02, ON M5R 1S6

27 Hillsboro Ave, Toronto C02 — Listed at $1,799,000. 6 bedroom, 3 bathroom 2-Storey Duplex. MLS® C12870052.

6Beds
3Baths
1500-2000sqft
Duplex
2-Storey
2Parking
$10,173Taxes/yr · 2025
See similar homes in this price range

Description

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 Details

Property TypeDuplex
Style2-Storey
CommunityAnnex
Approximate Age100+
Rooms11+4
Kitchens3
Washrooms3
Square Feet1500-2000 sqft
Lot Dimensions25 × 80 ft
Fronting OnSouth
Dir/Cross StDavenport and Avenue
ViewPark/Greenbelt
Garage TypeNone
DriveMutual
Parking Drive Spaces2
Total Parking Spaces2
ExteriorBrick
RoofAsphalt Rolled
FoundationConcrete
BasementApartment, Finished, Separate Entrance
Fireplace FeaturesWood
Heating TypeWater
Heating SourceGas
A/CWindow Unit(s)
SewersSewer
Taxes (2025)$10,173
HSTIncluded In
Listed Date3/11/2026
Days on Market246 days
PossessionImmediate

Virtual Tour

Powered by iGuide

This Listing Is No Longer Active

Browse similar active listings or get a free home evaluation.

Listing Courtesy of: ROYAL LEPAGE SIGNATURE REALTY

MLS® #C12870052

TRREBMLS®

The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The listing data is deemed reliable but is not guaranteed accurate by TRREB. The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.

© 2026 Toronto Regional Real Estate Board. All rights reserved.

Thinking about living in Toronto?

Explore the neighbourhood guide for Toronto — market trends, popular areas, buyer tips, and more.

HouseIndex Take: 27 Hillsboro Avenue

This duplex (2-Storey) is located in the Annex neighbourhood of Toronto.

The home offers 6+1 bedrooms, 3 bathrooms.

Features include a apartment, finished, separate entrance basement, 2 parking spaces, a fireplace.

Additional details: lot dimensions of 25 × 80 feet.

Similar Listings in This Price Range in Toronto C02

This property is no longer available. Explore comparable Duplex listings currently on the market, priced within 5% of this home.

About Toronto Real Estate

This Duplex is located in the Annex community in Toronto. Toronto is Canada's largest city and the economic hub of the Greater Toronto Area. With world-class transit, diverse neighbourhoods from the Annex to Scarborough, and proximity to major employers in the Financial District, it remains the most sought-after real estate market in Ontario. Buyers benefit from extensive GO Transit and TTC subway connectivity.

TTC subway & streetcar networkWorld-class dining & entertainmentUniversity of Toronto & major hospitals nearbyWaterfront trails & ravine parks
Walkability: Highly walkable — many neighbourhoods score 80+ on Walk Score
View full Toronto neighbourhood guide →