27 Hillsboro Avenue, Toronto, ON

Toronto, Central Toronto, Annex Hood
Davenport and Avenue
5+1 Br | 3 Bath | 1500-2000 Sqft
$1,799,000 For Sale

Property Overview

  • Duplex — 2-Storey
  • SqFt: | 1500-2000 Sqft
  • Lot Size: 25.00 x 80.00 Feet
  • Age: 100+ Years
  • Basement: Apartment, Finished, Separate Entrance
  • Exterior: Brick
  • Taxes: 10,173 / 2025
  • Zoning: n/a
  • MLS #: C13437452
  • Sewer: Sewer
  • Heat Source: Gas , Water

Property Description

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.

All appliances where located in as is conditions. All ELF's and window covering where they exist. W/D in basement (new 2024/25) Window A/C units in place in upper unit. Main level units stored in basement area. New boiler 2022, Hot water heater leased $30/month.

Property Details

  • For: For Sale
  • Type: Duplex
  • Style: 2-Storey
  • Lot: 25.00 x 80.00 Feet
  • Region: Toronto
  • Hood: Annex
  • Zoning: n/a
  • Lot Irreg: Fronting on: South
  • Fronting On: South

Building Details

  • Age: 100+ Years
  • Exterior: Brick
  • Heat: Gas , Water
  • A/C: Window Unit(s)
  • Interior Features: In-Law Capability, Water Heater Owned
  • Pool: None
  • Sewer: Sewer
  • Garage: None
  • Total Parking: 2.00
  • Driveway: Mutual

Property Interior

  • Sqft: 1500-2000 Sqft
  • Bed: 5 +1
  • Bath: 3
  • Kitchen: 2 +1
  • Family Room: No
  • Basement: Apartment, Finished, Separate Entrance
Rooms Details

Living Room

Main Level

4.5 x 3.02

Fireplace

Dining Room

Main Level

4.5 x 3.02

Window

Kitchen

Main Level

2.88 x 2.28

Window

Bedroom

Main Level

3.19 x 2.52

Window

Bedroom 2

Main Level

3.82 x 2.54

Window

Living Room

Upper Level

4.49 x 3

Window

Dining Room

Upper Level

2.79 x 2.65

Window

Kitchen

Upper Level

2.9 x 2.29

Primary Bedroom

Upper Level

4.49 x 3

Fireplace, W/O To Balcony

Bedroom 2

Upper Level

3.85 x 2.44

Window

Bedroom 3

Upper Level

3.19 x 2.49

Window

Living Room

Lower Level

4.67 x 2.74

Window

Kitchen

Lower Level

3.95 x 2.78

Eat-in Kitchen

Bedroom

Lower Level

5.33 x 3.42

Window

Utility Room

Lower Level

6.35 x 2.99

Combined w/Laundry, Window

Property Listed by: ROYAL LEPAGE SIGNATURE REALTY
Virtual Tour: https://unbranded.youriguide.com/27_hillsboro_ave_toronto_on/

Home Valuation Estimate

What is 27 Hillsboro Avenue, Toronto, ON worth in today’s Annex, Central Toronto market?

This HomeZira valuation preview helps buyers and sellers think through the asking price for this 5-bedroom Duplex with 1500-2000 sq. ft. in Annex, Central Toronto. The full estimate reviews the property’s location, home type, bedroom count, size range, age, and nearby comparable market activity after sign-in.

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Location

  • Address: 27 Hillsboro Avenue
  • Neighborhood: Annex
  • Zip/Postal Code: M5R 1S6
  • Nearby Amenities: Library, Park, Place Of Worship, Public Transit, Rec./Commun.Centre, School
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About 27 Hillsboro Avenue, Toronto C02, ON M5R 1S6, Central Toronto

Located at 27 Hillsboro Avenue, Toronto, ON in Central Toronto (Annex neighbourhood), near Davenport and Avenue. This freehold home offers Duplex, ["2-Storey"], 5 bedrooms, 3 bathrooms and 1500-2000 sq.ft. (approx.) in a layout suited to everyday family living. Basement: Apartment, Finished, Separate Entrance • 2 parking spots • Garage: None • Heating: Gas Water • Cooling: Window Unit(s). Property taxes are approximately $10,173 for 2025. 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.

FAQs for 27 Hillsboro Avenue, Toronto, ON , Annex , Central Toronto

What are the listing details for 27 Hillsboro Avenue, Toronto, ON?
27 Hillsboro Avenue, Toronto, ON is a Duplex for sale in Central Toronto, in the Annex neighbourhood, Toronto. The current list price is $1,799,000. MLS number: C13437452.
How many bedrooms and bathrooms does this home have?
27 Hillsboro Avenue, Toronto, ON is listed as a Duplex with a ["2-Storey"] style, featuring 5+1 bedroom(s) and 3 bathroom(s). The listed interior size range is 1500-2000 sq. ft..
What lot, basement, garage, or parking details are listed?
The lot size is listed as approximately 25.00 x 80.00 Feet. The basement is listed as: Apartment, Finished, Separate Entrance. Garage type: None. Total parking: 2 space(s).
What heating, cooling, and exterior details are shown?
Heating is listed as: Gas, Water. Cooling is listed as: Window Unit(s). Exterior/construction materials are listed as: Brick.
Where is this property located?
27 Hillsboro Avenue, Toronto, ON is located in the Annex neighbourhood of Central Toronto. The listed cross street is Davenport and Avenue.
What information is available on this public listing page?
The public listing page shows current active listing information, property photos, room details when available, map location, listed price, property features, and contact options. Annual taxes are listed as $10,173 / 2025. Valuation tools and similar sold-property previews are available after sign-in where applicable, without displaying sold data in this public FAQ.

FAQ content is based on current active listing fields shown on this page. Sold prices, sold comparables, and VOW-only details are not included in this public FAQ.