I don't have enough recent comparable sales to call this one's price, but new this week. Here's everything I've got on it — ask me anything.

Toronto · Toronto Region · Annex

27 Hillsboro Avenue

Duplex

MLS® #C14144160

Listed for$1,779,0003 days on market
5+1 bed 3 bath 2 parking 1500-2000 sq ft~$1,017/sq ft
  • New this week
  • 14 schools within 1 km
  • Transit stop ~70 m
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Is $1,779,000 a fair price?

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Est. all-in monthly~$9,125/momortgage + property tax + maintenance · 20% down · example rate (compounded semi-annually) — the math on the list price, not a quote or what you can afford. For real rates, Alex can connect you with a mortgage pro.

On the map

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14 schools within ~1 km · nearest transit stop ~0.07 km

Property information
What house buyers ask first
Lot size
25 × 80 ft
Square footage
1500-2000 sq ft
Age
~100+ years old
Property tax
$10,173 / yr
Parking
2 spaces · None
Basement
Apartment, Finished, Separate Entrance, Full

Property summary

Property type
Duplex
Style
2-Storey
Approx. age
100+ years
Lot size
25 × 80 ft
Parking
2 spaces · None
Heating
Water
Air conditioning
Window Unit(s)
Basement
Apartment, Finished, Separate Entrance, Full
Kitchens
2
Exterior
Brick
Property tax
$10,173 / yr
MLS®
C14144160

Room dimensions

Primary Bedroomfireplace, w/o to balcony
Upper4.49 × 3.0 m
KitchenEat-in Kitchen
Lower3.95 × 2.78 m
Living RoomWindow
Upper4.49 × 3.0 m
Dining RoomWindow
Main4.5 × 3.02 m
Utility Roomcombined w/laundry, window
Lower6.35 × 2.99 m
BedroomWindow
Lower5.33 × 3.42 m
Bedroom 3Window
Upper3.19 × 2.49 m
BedroomWindow
Main3.19 × 2.52 m
Kitchen
Upper2.9 × 2.29 m
Bedroom 2Window
Upper3.85 × 2.44 m
Bedroom 2Window
Main3.82 × 2.54 m
Living RoomWindow
Lower4.67 × 2.74 m
Dining RoomWindow
Upper2.79 × 2.65 m
KitchenWindow
Main2.88 × 2.28 m
Living RoomFireplace
Main4.5 × 3.02 m

As stated by the MLS®, nothing inferred.

Nearby homes for sale
The numbers that matter
The numbers that matter
Property tax
$10,173/yr
Est. all-in
~$9,125/mo
Nearby rental listings are facts. Whether it works as a rental is a chat with Alex — not a number I’ll put on it.
Schools

Schools near this home, closest first by straight-line distance. These are factual locations — AskEmma doesn’t rate or rank schools.

  • Jesse Ketchum Junior and Senior Public SchoolPublic · Elementary & Secondary · Toronto DSB0.3 km
  • McDonald International AcademyPrivate · Secondary · ..0.3 km
  • City High SchoolPrivate · Secondary · ..0.4 km
  • National E SchoolPrivate · Secondary · ..0.4 km
  • Dalton School, ThePrivate · Elementary & Secondary · ..0.4 km
  • CareerQuest - TorontoPrivate · Secondary · ..0.5 km

Locations: Open Database of Educational Facilities (ODEF), Statistics Canada v2.1 (2022) · Open Government Licence – Canada. School locations as of 2022 — confirm current catchment and enrolment with the school board. For official provincial results, check EQAO.

Getting around

Public transit near this home, by straight-line distance. Factual locations from OpenStreetMap — not walking time, and not a rating.

  • Belmont StreetNearest transit · Bus stop~70 m
  • Cresecent Road EntranceNearest subway · Subway~350 m
  • Toronto Union StationNearest GO / rail · GO / regional rail~3.5 km

Locations: OpenStreetMap public-transit stops, © OpenStreetMap contributors · Open Database Licence (ODbL). Stop locations from OpenStreetMap — confirm current routes and service with the transit agency.

Community — Toronto
$850KMedian sold
32Median days on market
98.6%Sale-to-list
Median sold price · Toronto1-yr +2% · 3-yr —
Source: TRREB sold data via Repliers · all property types
Neighbourhood demographics — Toronto
2,794,356Population (2021)
39.6Median age
$84,000Median household income
51.9%Home owners
48.1%Renters
2.4Avg household size
Source: Statistics Canada, 2021 Census
Description & details

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.

The data only goes so far — condition, light and layout are worth seeing in person, with a home inspection, before you commit.

Listed by ROYAL LEPAGE SIGNATURE REALTY. Showings via AskEmma by Alex Goodman, Sales Representative, RE/MAX Your Community Realty, Brokerage.