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$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. MLS® C13437452.
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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. All units are vacant, The upper two units have been 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

Your agent: Vick Yogeswaran
REALTOR® · RE/MAX Realtron Realty Inc.
Listing Courtesy of: ROYAL LEPAGE SIGNATURE REALTY
MLS® #C13437452


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.
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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 basement, 2 parking spaces, a fireplace.
Additional details: lot dimensions of 25 × 80 feet.
Listed at $1,799,000 CAD with annual property taxes of $10,173 (2025). This listing has been on the market for 9 days.
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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.