Summer view street
Front Street view
Entrance
Front porch Main level
View of Ramsden Park Lv 1
Main Bath level 1
Bedroom Lv 1
Bedroom Lv 1 virtual option
Bedroom Upper
Shared drive
Kitchen Lv 1
Living/Dining Lv 1
Lv 1 living and Dining
Main flor living and dining. Virtual Option
Level 1 Dining
View of Park Level 2
Reae entrance to In-Law suite
Rear Parking 2 vehicles
Rear Parking
Entry stairs for upper level
Primary Level 2
Staged Lv 2 Bedroom - Virtual options
Primary w/FP Lv 2
Dining Lv 2 virtual Option
Sunroom/dining Lv 2
Sunroom/ dining 2 of 2
Sunroon/dining Lv 2 Virtual option
Upper Level Kitchen
Upper level Bath
Upper Level Porch
Upper Level Porch 2
Summer view
Basement kitchen
Basement eating area
Basement living area
Basement sleeping area
Basement bath, with tub/shower

27 Hillsboro Avenue

Toronto C02, ON M5R 1S6

Off-Market
6 Beds
3 Baths
1,500 Sq Ft
Multi-Family
This listing is no longer active on the MLS® and is not currently for sale. Interested in something similar? Ask Filipe →

About This Property

27 Hillsboro Avenue Opportunity Meets Lifestyle in the Heart of Ave & Dav. 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. The home features a shared (skinny) driveway with parking for two vehicles a true bonus for this location. All units are vacant. Upper two units are 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 is vacant as well. Laundry and utilities are shared, keeping operations straight forward.From a future-planning perspective, the options here are compelling: Keep the current duplex configuration, Restore to a stunning single-family home, or Upgrade or reposition the property to maximize its potential An initial zoning review by Property Pathways indicates potential 6-plex compliance (buyers t 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.

Property Details

StatusOff-Market
Property TypeMulti-Family
Listing TypeSale
Interior Size1,500 sq ft
Bedrooms6
Bathrooms3
Postal CodeM5R 1S6
Last UpdatedOct 8, 2026 · 8:47 a.m.

Sign in for full listing history and the exact list date.

Features & Amenities

  • View
  • Fireplace
  • Air Conditioning
  • Basement

Buying or selling in Toronto?

Filipe & Isabel Ferreira and the Team Filipe (RE/MAX Ultimate Realty Inc., Brokerage) represent buyers and sellers here. Local guides and live listings below.

Talk to Filipe & Isabel Ferreira →

TRREB MLS® Attribution

MLS® C12722748

Listed by ROYAL LEPAGE SIGNATURE REALTY

The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA. The trademarks REALTOR®, REALTORS® and the REALTOR® logo are controlled by CREA and identify real estate professionals who are members of CREA. Listing data provided by the Toronto Regional Real Estate Board (TRREB). The information contained herein is from sources believed to be reliable but is not guaranteed. Information deemed reliable but not guaranteed accurate by TRREB or Team Filipe / RE/MAX.

$1,899,000

last list price — no longer for sale

MLS®C12722748
TypeMulti-Family
CityToronto C02
Search Active Listings

Team Filipe · RE/MAX · (647) 210-6070

Listed By

ROYAL LEPAGE SIGNATURE REALTY