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Duplex for sale at 27 Hillsboro Avenue, Toronto C02 - 6 bedroom, 3 bathroom - Photo 1 of 28
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$1,779,000

27 Hillsboro Ave

Toronto C02, ON M5R 1S6

27 Hillsboro Ave, Toronto C02 — Listed at $1,779,000. 6 bedroom, 3 bathroom 2-Storey Duplex. MLS® C14144160.

Possession · seller's timeline

Immediate

6Beds
3Baths
1500-2000sqft
Duplex
2-Storey
2Parking
$10,173Taxes/yr · 2025
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Description

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 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, Full
Fireplace FeaturesWood
Heating TypeWater
Heating SourceGas
A/CWindow Unit(s)
SewersSewer
Taxes (2025)$10,173
HSTIncluded In
Listed Date11/3/2026
Days on Market9 days
PossessionImmediate

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Listing Courtesy of: ROYAL LEPAGE SIGNATURE REALTY

MLS® #C14144160

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.

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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, full basement, 2 parking spaces, a fireplace.

Additional details: lot dimensions of 25 × 80 feet.

Listed at $1,779,000 CAD with annual property taxes of $10,173 (2025).

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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 →