Ossington Strip Property Management

The Ossington Strip runs along Ossington Avenue between Queen Street West to the south and Dundas Street West to the north, with the surrounding residential blocks extending roughly one block east and west of the avenue. The corridor evolved from a working-class commercial street into one of Toronto’s most recognized dining, bar, and gallery destinations over the past two decades. Its housing stock combines Victorian and Edwardian-era row houses and semi-detached homes with a small number of boutique loft and mid-rise condominium buildings constructed since the mid-2010s. Successful Ossington Strip property management requires understanding both the heritage residential fabric that defines the side streets and the premium rents that the corridor’s commercial reputation supports.

The neighbourhood falls under TRREB district C01 (Toronto C01) in the Toronto Regional Real Estate Board’s MLS system. Buttonwood Property Management has managed investment properties in the Ossington Strip since 2011. Every tenancy we manage in the neighbourhood is subject to:

• Ontario Residential Tenancies Act

• Real Estate Council of Ontario (RECO)

• Ontario Human Rights Tribunal

• Ontario Building Code

• Ontario Fire Code

• Vacant Home Tax (City of Toronto)

• CRA’s Non-resident Tax Withholding on Rental Income (NR4/NR6)

History of the Ossington Strip

Ossington Avenue was a quiet residential and commercial street through much of the twentieth century, anchored by the Portuguese and Italian immigrant communities that settled in the surrounding blocks after the Second World War. Portuguese bakeries, fish shops, and social clubs defined the commercial character of the strip through the 1970s, 1980s, and 1990s. The stretch between Queen and Dundas functioned as a neighbourhood-serving retail corridor, distinct from the higher-profile commercial activity on Queen Street West to the south.

The transformation began in the early 2000s. Rising rents on Queen Street West pushed artists, gallery operators, and independent restaurateurs north to Ossington, where commercial rents were significantly lower and the building stock offered raw, adaptable spaces. By 2008 and 2009, the corridor had established a critical mass of cocktail bars, restaurants, and galleries that attracted citywide attention. The City of Toronto’s 2008 moratorium on new bar and restaurant liquor licences along the strip (which lasted until 2015) paradoxically solidified Ossington’s reputation as a destination, limiting supply while demand continued to grow.

The Portuguese community has gradually dispersed, though vestiges remain in the businesses and social organizations along the avenue. Today the Ossington Strip is recognized as one of Toronto’s premier dining and nightlife corridors, with a residential tenant base that values walkability, independent retail, and proximity to Trinity Bellwoods Park.

The Housing Stock in the Ossington Strip

The dominant housing types along the Ossington Strip’s side streets are Victorian and Edwardian semi-detached homes, row houses, and detached workers’ cottages from the late 1800s and early 1900s. Many of these homes have been converted into multi-unit rental properties with basement suites, upper-floor apartments, and laneway housing. The housing character is low-rise and streetwall-oriented, consistent with the broader west end pattern.

Condominium development along the strip has been boutique in scale, reflecting the neighbourhood’s low-rise zoning and heritage sensibility.

• 109OZ Lofts (109 Ossington Avenue). A 6-storey loft-style building containing 85 condo units, developed by Reserve Properties. Completed in 2016. The building sits on the strip between Queen and Dundas with an industrial-inspired design that reflects the corridor’s gallery and studio character.

• Motif Lofts and Towns (41 Ossington Avenue). A 5-storey boutique building containing 28 condo units and townhomes, developed by Reserve Properties. Completed in 2016. Located at the southern end of the strip near Queen Street West.

Rental inventory beyond the condo buildings consists primarily of apartments in converted Victorian homes, upper-floor units above commercial storefronts, and basement suites. Managing these property types requires direct coordination with contractors for building systems, roofing, and seasonal maintenance, as responsibility falls to the landlord rather than a condo corporation.

Buildings Under Construction

The Ossington Strip has limited new development activity, consistent with the corridor’s low-rise zoning, though the intersection with Dundas Street West has attracted mid-rise investment.

• The Twelve Hundred (1200 Dundas Street West, Toronto, ON M6J 1X2). An 8-storey mid-rise containing 115 condo units, developed by Fieldgate Urban. Under construction at the corner of Dundas Street West and Ossington Avenue, with completion expected in 2025.

Market Prices: Renting and Buying in the Ossington Strip

Rental prices. The average monthly rent for a one-bedroom unit near the Ossington Strip ranges from $2,200 to $2,600, with two-bedroom units ranging from $2,800 to $3,200. The corridor commands a premium over comparable west end addresses, driven by its restaurant and bar scene, proximity to Trinity Bellwoods Park, and high walkability. The tenant base skews toward young professionals in creative industries, tech, and media who prioritize neighbourhood character over unit size.

Sale prices. Condo units in the Ossington Strip’s boutique buildings sell at approximately $900 to $1,050 per square foot, with one-bedroom units typically priced between $550,000 and $720,000 in early 2026. Freehold homes on the surrounding residential streets trade at significantly higher price points, generally $1.3 million to $2.2 million depending on lot size, condition, and proximity to the strip.

Current Listings Managed by Buttonwood

Buttonwood manages rental properties along the Ossington Strip, from loft units at 109OZ to converted heritage apartments on the surrounding residential streets. Current availability changes throughout the year; visit the Buttonwood listings page for up-to-date inventory.

How Tenants Commute from the Ossington Strip

Walk Score data rates the Ossington Strip at 99 out of 100 for walkability (Walker’s Paradise), 93 out of 100 for transit (Rider’s Paradise), and 92 out of 100 for cycling (Biker’s Paradise).

Public transit. The 63 Ossington bus runs north-south along Ossington Avenue, connecting to Ossington Station on Line 2 (Bloor-Danforth) to the north. The 363 Ossington provides overnight service along the same route. The 501 Queen streetcar runs east-west along Queen Street West at the southern end of the strip, and the 505 Dundas streetcar serves the northern end along Dundas Street West.

Cycling. Dedicated cycling infrastructure on Dundas Street West and the surrounding residential grid connects the Ossington Strip to the downtown core and High Park to the west. Trinity Bellwoods Park, two blocks east, provides additional north-south cycling routes.

Driving. The Gardiner Expressway is accessible via Dufferin Street or Strachan Avenue to the south. Highway 401 is reachable via the Allen Road expressway from Eglinton Avenue to the north.

Schools in the Ossington Strip

Families renting in the Ossington Strip have access to TDSB schools within the neighbourhood and its surrounding blocks.

Ossington/Old Orchard Junior Public School (380 Ossington Avenue, JK-6) is located directly on Ossington Avenue and serves the core of the strip’s residential area.

Alexander Muir/Gladstone Avenue Junior Public School (8 Gladstone Avenue, JK-6) is located west of Ossington on Gladstone Avenue and serves portions of the surrounding neighbourhood.

Central Technical School (725 Bathurst Street, Grades 9-12) is one of Toronto’s largest secondary schools, located east of the strip on Bathurst Street with specialized programs in visual arts and technology.

How Buttonwood Manages Ossington Strip Properties

Tenant screening is where outcomes are determined. The process Buttonwood uses was developed across thousands of tenancies throughout the GTA since 2011, and the result is six evictions in that entire period for non-payment of rent. These results are driven by proprietary tenant screening processes and procedures that Buttonwood perfected over time.

Once a qualified tenant is placed, management covers rent collection, maintenance coordination, lease renewal tracking, and annual rent increase notices issued under the Ontario Residential Tenancies Act. Property owners based outside Canada benefit from our non-resident tax compliance services, including CRA withholding obligations and NR4/NR6 reporting on rental income.

The Ossington Strip’s rental inventory includes a significant share of converted heritage homes and above-retail apartments. These property types require hands-on building oversight: Buttonwood coordinates directly with contractors for plumbing, electrical, HVAC, roofing, and seasonal maintenance rather than deferring to a condo board.

Working with Ossington Strip Landlords

Landlords who own a rental property on the Ossington Strip, whether a loft unit at 109OZ, a converted Victorian duplex on a side street, or an above-retail apartment on the avenue itself, need a management partner who understands the premium rental market that the corridor’s commercial reputation supports.

Buttonwood delivers a value proposition that is affordable, carries the best reputation within the industry, and applies an uncommon level of expertise and ethical standard that both landlords and tenants deserve. More than 70% of our business comes through referrals.

• #1 Individual Associate – Units KW Canada 2025 – Top 5 Individuals (Keller Williams Portfolio Realty)
• Platinum Award 2024 (iPro Realty Ltd.)
• Platinum Award 2023 (iPro Realty Ltd.)
• Platinum Award 2022 (iPro Realty Ltd.)
• President’s Award 2021 (iPro Realty Ltd.)
• Platinum Award 2020 (iPro Realty Ltd.)
• President’s Award 2019 (iPro Realty Ltd.)
• Executive’s Club Award 2017 (Kingsway Real Estate Brokerage)
• 100 Percent Club Award 2016 (Kingsway Real Estate Brokerage)

Those are not marketing claims; they are measurable results over 14 plus years of rental and management services in The Greater Toronto Area.

A Neighbourhood That Rewards Careful Management

Trinity Bellwoods Park sits two blocks east of Ossington Avenue and serves as the neighbourhood’s primary green space. The park’s 14.6 hectares provide tennis courts, a swimming pool, a dog park, and an ice rink, all of which contribute to tenant retention among the young professional and family renters who dominate the Ossington Strip’s tenant base. The corridor’s restaurant and gallery scene provides the neighbourhood identity that draws tenants in the first place; the park and the residential street character are what keep them.

Our west end portfolio extends beyond the Ossington Strip. We manage investment properties in Trinity Bellwoods to the east, Palmerston – Little Italy to the north, Queen West to the southeast, and Dundas Street West to the west.

Contact Buttonwood to discuss management of your Ossington Strip investment property. Whether you own a loft unit in one of the corridor’s boutique buildings, a converted heritage home on a side street, or a rental property above a storefront on the avenue, we can provide a direct assessment of what your property requires.