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43.73° N · 79.40° W — Toronto & nearby · 9,740 homes for sale today43.73° N · 79.40° W — 9,740 homes today(647) 554-7436Saved

43.6753° N · 79.3925° W — Annex, Toronto — MLS® #C14144160

27 Hillsboro Ave

$1,779,000

Annex, Toronto, Ontario M5R 1S6

5+1
BedroomsBeds
3
BathroomsBaths
1500-2000 sqft1500-2000
SizeSq ft
25 x 80 ft
Lot sizeLot

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ToShemeer AhmadVALERY REAL ESTATE INC.
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In short · from the listing record

27 Hillsboro Ave is a 5+1-bedroom, 3-bathroom duplex in Annex, Toronto, listed for sale at an asking price of $1,779,000 (MLS® C14144160).

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.

Listing readings

How it measures up

Scores from the listing record and the market around it.

  • 73Good

    Condition score

    1 documented update signal

    Listing age, structured features and disclosed update language; not an inspection.

  • 27Shortfall

    Cash flow quality

    −$2,965/mo against the cost of owning (20% down, 4.8%, 25 yrs)

    Median of 62 homes with 6 bedrooms for lease in Toronto right now. Cost of owning counts the mortgage and property tax.

Condition uses listing-record signals, not an inspection.

The data table

Every fact

Everything the board publishes for this home.

Tax
$10,173 / 2025
MLS® number
C14144160
Board
TRREB MLS®
Property Type
Duplex
Building Age
100+
Time on market
Size
1500-2000 sqft
Lot Size
25 x 80 ft
Listed on
Parking
None, 2 Parking

Listing history

Listing activity for 27 Hillsboro Ave, Toronto, Ontario

Date StartDate EndList PricePriceEventListing ID
Date StartN/AN/A$1,779,000N/AFor SaleC14144160

Inside

Room by room

From the listing.

Main5 rooms
  • Living3.02 × 4.5 mFireplace
  • Dining3.02 × 4.5 mWindow
  • Kitchen2.28 × 2.88 mWindow
  • Br2.52 × 3.19 mWindow
  • 2nd Br2.54 × 3.82 mWindow
Upper6 rooms
  • Living3.0 × 4.49 mWindow
  • Dining2.65 × 2.79 mWindow
  • Kitchen2.29 × 2.9 m
  • Primary3.0 × 4.49 mFireplace, W/O To Balcony
  • 2nd Br2.44 × 3.85 mWindow
  • 3rd Br2.49 × 3.19 mWindow
Lower4 rooms
  • Living2.74 × 4.67 mWindow
  • Kitchen2.78 × 3.95 mEat-In Kitchen
  • Br3.42 × 5.33 mWindow
  • Utility2.99 × 6.35 mCombined W/Laundry, Window

Property

Property Type
Duplex
Style
2-Storey
Community
Annex
Municipality
Toronto

Building

Size
1500-2000 sqft
Building Age
100+
Construction
Brick

Inside

Bedrooms
5+1
Bathrooms
3
Bathroom Details
1 × 4pc Bsmt, 1 × 4pc Main, 1 × 4pc Upper
Basement Type
Apartment
Kitchens
2

Parking

Driveway
Mutual
Garage Type
None
Additional Parking
2
Total Parking
2

Utilities

Water
Municipal
Cooling
Window Unit
Heating Type
Water

Land

Sewer
Sewers
Frontage
25 ft
Depth
80 ft
Lot Size
25 x 80 ft

Where it sits

The street and the area

Asking prices on the map.

Map and tour

Transit nearby

StationLinesDistance
Rosedale StationTTC subway: Line 1 Yonge-University350 m
Bay StationTTC subway: Line 2 Bloor-Danforth600 m
Bloor-Yonge StationTTC subway: Line 1 Yonge-University, Line 2 Bloor-Danforth700 m
Eglinton StationTTC subway: Line 1 Yonge-UniversityTTC light rail: Line 5 Eglinton3.4 km
Union StationTTC subway: Line 1 Yonge-UniversityGO Transit train: Barrie, Kitchener, Lakeshore East, Lakeshore West, Milton, Richmond Hill, StouffvilleUP Express train3.5 km

The nearest subway, light rail, train, bus rapid transit stations 5 km, as the crow flies. Source: TTC schedule data (GTFS) from the Toronto Transit Commission under the Open Government Licence – Toronto; GO Transit and UP Express schedule data (GTFS) from Metrolinx under the Open Government Licence – Ontario – Metrolinx, downloaded October 18, 2026. Contains information licensed under the Open Government Licence – Toronto. Data used in this product or service is provided with the permission of Metrolinx. Metrolinx makes no representations or warranties of any kind, express or implied, with respect to the Data and assumes no responsibility for the accuracy or currency of the data used in this product or service. Contains information licensed under the Open Government Licence – Ontario – Metrolinx.

Site report

What the record says

What the City and the conservation authority have on file for this address.

  • Heritage and ravineNone foundNot found on the Heritage Register
  • Heritage and ravineNone foundNot in a mapped Heritage Conservation District
  • Heritage and ravineNone foundNot in the mapped ravine protection area
  • ZoningR (f5.0; d1.0) (x485)Residential zone (R) · Chapter 10, section 10.10 of By-law 569-2013 · Exception 900.2.10(485)
  • PermitsNone on fileNo building permits on file at this address.
  • Signals nearby6 to note100 DAVENPORT RD, Site plan, 200 m away · 100 DAVENPORT RD, Condominium, 200 m away · 109 PEARS AVE, Site plan, 310 m away · 111 PEARS AVE, Site plan, 320 m away · 185 AVENUE RD, Site plan, 320 m away · 183 AVENUE RD, Site plan, 330 m away
  • ca regulatedNone in rangeNot in Toronto and Region Conservation Authority’s mapped regulated area
  • provincial plansNone in rangeOutside the Greenbelt, Oak Ridges Moraine and Niagara Escarpment plan areas
  • wetlandNone in rangeNo mapped wetland within 120 m
  • aggregateNone in rangeNo licensed pit or quarry within 2 km
  • wellsNone in rangeNo recorded oil, gas or salt well within 250 m
  • railOn recordNearest rail line: 490 m
  • trailOn recordA trail on the Ontario trail network within 1 km
  • permitsOn record49 building permits issued within 250 m in the last 2 years
  • devappsOn record2 open development applications within 250 m An application is a proposal: it may change, be refused or never be built.
  • airportOn recordNearest airport: 4.5 km
  • parcelOn recordMapped parcel: about 1,680 sq ft Measured from the municipal parcel map, which can differ from the survey and from the lot size in the listing.
  • water wellsNone in rangeNo water-supply well recorded within 250 m 21 test or monitoring holes also recorded.
  • groundwaterOn recordGroundwater recorded about 15.1 m below ground nearby The middle water level in the well records within 500 m (256 records). It changes with the season and from spot to spot.
  • npriNone in rangeNo facility within 1 km reports pollutant releases to Environment Canada The nearest is The Governing Council of the University of Toronto — St George Campus, 1.6 km away. Only facilities above the inventory’s reporting thresholds are listed.
  • fcsiNone in rangeNo federal contaminated site within 1 km The federal inventory covers federal land only; it says nothing about provincial or private sites.
  • electricityOn recordElectricity is distributed here by Toronto Hydro-Electric System Limited
  • internet speedOn recordWired internet 50/10 Mbps or faster is listed at a household 40 m away Fixed wireless 50/10 Mbps or faster. LTE mobile coverage listed. ISED’s National Broadband Data at the nearest household point (40 m from the listing); 50/10 Mbps is its top category and includes faster plans. Confirm with a provider for this address.
  • broadbandOn recordAcross the surrounding area: fibre to the home, cable, DSL internet listed Fibre to the home: Beanfield Metroconnect, Bell, Dotto One, FibreStream, Rogers. Cable: Rogers. DSL: Bell. Fixed wireless: Bell, Rogers, Routcom, SkyChoice Communications. Mobile: Bell, Freedom Mobile, Rogers, Telus. Satellite: Xplore. ISED’s list for the surrounding ~25 km² area; check with a provider for this address.

None of these City records was found at this address. That does not rule out other approvals, such as a conservation authority permit, so check before you plan work.

Each record is the map at the home’s location, not an inspection. Confirm anything that matters with the municipality, Toronto and Region Conservation Authority or the record’s publisher.

City of Toronto Open Data and zoning map, read at this address. Contains information licensed under the Open Government Licence – Toronto. City of Toronto Open Data — Development Applications and Building Permits (cleared permits since 2017). An application is a proposal: it may change, be refused or never be built. Contains information licensed under the Open Government Licence – Toronto. Contains information licensed under the Open Government Licence – Canada. Contains information licensed under the Open Government Licence – Ontario. Contains information licensed under the Open Government Licence – Toronto. Contains information made available under the Toronto and Region Conservation Authority Open Data Licence v1.0.

Lot

Lot area
2,000 sq ft186 m²
Street frontage
25 ft7.6 m
Depth
80 ft24.4 m
25 × 80 ftHILLSBORO AVE

The area is the frontage multiplied by the depth, so boundaries are approximate. Confirm with a survey before you buy.

Source: the MLS® listing record.

Land transfer tax on this home

Ontario land transfer tax
$32,055
Toronto municipal land transfer tax
$32,055
Total land transfer tax
$64,110
First-time buyer rebates (Ontario up to $4,000 + Toronto up to $4,475)
−$8,475
Total for first-time buyers
$55,635
See how this is worked out
0.5% on the first $55,000
$275
1.0% from $55,000 to $250,000
$1,950
1.5% from $250,000 to $400,000
$2,250
2.0% from $400,000 to $1,779,000
$27,580
Ontario total
$32,055

Toronto’s municipal tax uses the same brackets at this price, so it adds another $32,055.

An estimate at the asking price, for a home with one or two single-family residences. Your lawyer confirms the exact amount.

Schools

Nearest schools

Straight-line distances. Check catchments with the board.

ElementaryEQAO average 2024–25

  • Jesse Ketchum Junior and Senior Public SchoolToronto DSBPublic · grades JK–889%Grade 6 average250 m
  • Cottingham Junior Public SchoolToronto DSBPublic · grades JK–6100%Grade 6 average600 m
  • Our Lady of Perpetual Help Catholic SchoolToronto CDSBCatholic · grades JK–892%Grade 6 average1.5 km
  • École élémentaire Gabrielle-RoyConseil scolaire ViamondeFrench-language public · grades JK–696%Grade 6 average2.7 km

SecondaryGrade 9 math 2024–25

  • St Joseph's College SchoolToronto CDSBCatholic · grades 9–1266%Grade 9 math1.3 km
  • Msgr Fraser College (Isabella Campus)Toronto CDSBCatholic · grades 9–12—1.4 km
  • Jarvis Collegiate InstituteToronto DSBPublic · grades 9–1234%Grade 9 math1.6 km
  • Collège français secondaireConseil scolaire ViamondeFrench-language public · grades 9–1286%Grade 9 math1.9 km

EQAO: share of students at or above the provincial standard, 2024–25 (Ontario open data). These are the schools nearest this home, not the schools it is assigned to: boundaries change, and some schools take students by application. Confirm with the board before you buy. Contains information licensed under the Open Government Licence – Ontario.

Searches this home is in

Keep looking

The ledger

What it costs to own

Worked out for this home. Change any number.

Price$1,779,000

A month, all in

$8,965

  • Mortgage$8,117
  • Property tax$848

A planning figure, not a quote.

Land transfer tax

$64,110

$55,635 for first-time buyers; Toronto adds its own tax.

Rent, similar homes

$6,000

a month, median asking rent of 62 similar homes in Toronto.

Community

Who lives around it

Similar homes

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Shemeer Ahmad

Shemeer AhmadVALERY REAL ESTATE INC.

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(647) 554-7436

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