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.
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In-Law CapabilityWater Heater OwnedPark/GreenbeltLibraryParkPlace Of Worship
Facts & features
TypeMultiplex
Style2-storey
Built100+
Size1.5K~2K Sq.Ft.
Lot25 x 80 ft
Tax$10,173 (2025)
HeatingWater, gas
CoolingWindow unit(s)
BasementApartment, finished, separate entrance
WaterMunicipal
FireplaceYes, wood
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Wed28Oct
Thu29Oct
Fri30Oct
Sat31Oct
Sun1Nov
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Rooms
15 rooms · 3 bathrooms
Main floor5 rooms
Bedroom 212′6″ × 8′4″104 sq.ft.
Bedroom10′6″ × 8′3″87 sq.ft.
Kitchen9′5″ × 7′6″71 sq.ft.
Dining room14′9″ × 9′11″146 sq.ft.
Living room14′9″ × 9′11″146 sq.ft.
Upper floor6 rooms
Living room14′9″ × 9′10″145 sq.ft.
Kitchen9′6″ × 7′6″71 sq.ft.
Bedroom 310′6″ × 8′2″85 sq.ft.
Primary bedroom14′9″ × 9′10″145 sq.ft.
Dining room9′2″ × 8′8″80 sq.ft.
Bedroom 212′8″ × 8′101 sq.ft.
Lower level4 rooms
Kitchen13′ × 9′1″118 sq.ft.
Bedroom17′6″ × 11′3″196 sq.ft.
Utility room20′10″ × 9′10″204 sq.ft.
Living room15′4″ × 9′138 sq.ft.
Bathrooms3
4-pcMain4-pcUpper4-pcBasement
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