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For saleNew listingMLS® C14144160

27 Hillsboro Avenue, Toronto, ON M5R 1S6

Annex · C02 · M5R 1S6

$1,779,000

$1,186 / sq ft

Listed yesterday

Bedrooms
5+1
Bathrooms
3
Interior
1,500 sf
Parking
2
Lot
25 × 80 ft
Age
100+ years

What's special

  • 2 parking spaces
  • Window unit(s)
  • Basement apartment
  • 2 fireplaces
  • In-law capability
  • Water heater owned

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About this property

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.

Rooms

15 rooms. Dimensions as published by the listing brokerage.

Room dimensions and features
RoomLevelDimensionsFeatures
Living RoomMain4.50 × 3.02 m14.8 × 9.9 ftFireplace
Dining RoomMain4.50 × 3.02 m14.8 × 9.9 ftWindow
KitchenMain2.88 × 2.28 m9.4 × 7.5 ftWindow
BedroomMain3.19 × 2.52 m10.5 × 8.3 ftWindow
Bedroom 2Main3.82 × 2.54 m12.5 × 8.3 ftWindow
Living RoomUpper4.49 × 3.00 m14.7 × 9.8 ftWindow
Dining RoomUpper2.79 × 2.65 m9.2 × 8.7 ftWindow
KitchenUpper2.90 × 2.29 m9.5 × 7.5 ft—
Primary BedroomUpper4.49 × 3.00 m14.7 × 9.8 ftFireplace · W/O To Balcony
Bedroom 2Upper3.85 × 2.44 m12.6 × 8.0 ftWindow
Bedroom 3Upper3.19 × 2.49 m10.5 × 8.2 ftWindow
Living RoomLower4.67 × 2.74 m15.3 × 9.0 ftWindow
KitchenLower3.95 × 2.78 m13.0 × 9.1 ftEat-in Kitchen
BedroomLower5.33 × 3.42 m17.5 × 11.2 ftWindow
Utility RoomLower6.35 × 2.99 m20.8 × 9.8 ftCombined w/Laundry · Window

Features

  • In-Law Capability
  • Water Heater Owned

Property details

Property

Property type
multiplex
Bedrooms
5 + 1
Bathrooms
3
Interior size
1,500 sq ft
Year built
100+
Lot size
25 × 80 ft
Possession
Immediate

Interior

Basement
Apartment, Finished, Separate Entrance, Full
Heating
Water · Gas
Cooling
Window Unit(s)
Fireplaces
2
Exposure
South

Exterior & services

Construction
Brick
Parking spaces
2
Sewer
Sewer

Costs

List price
$1,779,000
Property taxes
$10,173 / year (2025)
Price per sq ft
$1,186
Rental items
Hot water heater

Listing

MLS® number
C14144160
Status
For sale
Listed
November 3, 2026
Days on market
1
Last updated
November 3, 2026
Listing brokerage
ROYAL LEPAGE SIGNATURE REALTY

Price & sale history

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Before you make an offer

What this home costs beyond the asking price, and how that price compares to what else is on the market.

How this price compares

This home is priced below most comparable listings — about 22% of comparable multiplex listings in Annex are asking less.

$1.62MMedian $2.39M$4.40M
This home
$1,186 / sq ft
Comparable median
$800 / sq ft

Based on 9 comparable active multiplex listings in Annex. These are asking prices, not sale prices.

Mortgage estimate

Down payment20.0% · minimum $355,800
$355,800
Interest rate5-year fixed, illustrative only
4.49%
Amortization
Principal & interest
$7,869.12
Property tax (est.)
$847.75
Estimated monthly
$8,717

Estimate only. Excludes CMHC insurance premiums, which apply below 20% down, and does not constitute a mortgage approval or an offer of credit.

Land transfer tax

Payable on closing, on top of the purchase price.

Ontario
$32,055
Toronto municipal
$32,055
Total due on closing
$64,110

An estimate on the asking price of $1,779,000. Rates current as of September 2026; confirm the final figure with your real estate lawyer.

Listing courtesy of ROYAL LEPAGE SIGNATURE REALTY. Listing data is provided in part by the Toronto Regional Real Estate Board (TRREB) and is deemed reliable but is not guaranteed accurate. Information is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties. Data is updated every 15 minutes.

$1,779,000

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