Listed by Royal Lepage Signature Realty.

27 Hillsboro Avenue is a Duplex, 2-Storey and is currently for Sale @ $1,899,000. Taxes in 2025 were $10,173.00.

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27 Hillsboro Avenue Opportunity Meets Lifestyle in the Heart of Ave & Dav. The 2-Storey on 27 Hillsboro Avenue has 5 bedrooms, 3 bathrooms, and is located on a 80 x 25 ft lot in the community of Annex . 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. All units are vacant. Upper two units are 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 vacant as well. 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, or 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.

The address 27 Hillsboro Avenue was listed for sale (MLS# C12722748) on Thursday, January 22, 2026.