27 Hillsboro Avenue
Annex · Toronto, ON M5R 1S6
Listing brokerage: ROYAL LEPAGE SIGNATURE REALTY
Asking price
$1,779,000
Key facts
- MultiplexProperty type
- 6Bedrooms
- 3Bathrooms
- 2 spacesParking
- 1,750 sq ftLiving space
- 25 ftLot frontage
- Nov 3, 2026Listed
- 5 daysOn market
- C14144160MLS® number
About this home
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.
Price history
- Listed$1,779,000
Location
27 Hillsboro Avenue, Toronto
Schools & transit
School locations and boards shown from open data. We do not publish rankings; any future scores will be sourced, dated and shown factually.
Nearby schools
- Jesse Ketchum Junior and Senior Public SchoolToronto DSB · Elementary · 258 m in a straight lineBoundary data unavailable for this board — we don't guess catchment lines.
- Lolart SchoolPrivate · Secondary · 312 m in a straight lineBoundary data unavailable for this board — we don't guess catchment lines.
- McDonald International AcademyPrivate · Secondary · 312 m in a straight lineBoundary data unavailable for this board — we don't guess catchment lines.
Nearby transit
Lines nearby: Line 1, 19, 82, 97, 320
- Davenport Rd at Belmont StTTC · 73 m in a straight line · about 1 min walk (estimate) · 19
- Davenport Rd at New StTTC · 81 m in a straight line · about 1 min walk (estimate) · 19
- Rosedale StationTTC · 285 m in a straight line · about 4 min walk (estimate) · Line 1, 82, 97, 320
Estimated commute
- Downtown Mississauga (Square One)~86 minestimate
- Downtown Toronto (Union Station)~20 minestimate
- Toronto Pearson Airport~74 minestimate
How is the commute estimated?
Estimate only. A coarse model from straight-line distance and an average transit speed — not a live routed trip. Actual times vary with schedules, transfers and traffic.
Sources
- Contains information licensed under the Open Government Licence – Ontario. Source: Ontario Ministry of Education.
- Contains information licensed under the Open Government Licence – Toronto.
MLS® #C14144160
Last updated Nov 3, 2026
MLS®, Multiple Listing Service®, and the associated logos are owned by The Canadian Real Estate Association (CREA)/the applicable board and identify the quality of services provided by real estate professionals who are members.
Listing data is provided under licence by the Toronto Regional Real Estate Board and is deemed reliable but not guaranteed accurate.



