Annex Property Management

The Annex sits in midtown Toronto, bounded by Bloor Street West to the south, Dupont Street and the rail corridor to the north, Avenue Road to the east, and Bathurst Street to the west. The neighbourhood contains one of the largest collections of heritage-designated Victorian and Edwardian houses in the city, alongside boutique condominium buildings and heritage conversions that have been integrated into the original residential fabric. The University of Toronto campus borders the neighbourhood to the south and east, shaping its academic and cultural identity. Successful The Annex property management needs to take all that into consideration when working on rental and management on behalf of investors.

The neighbourhood falls under TRREB district C02 (Toronto C02) in the Toronto Regional Real Estate Board’s MLS system. Buttonwood Property Management, a Toronto property management company, has managed investment properties in The Annex 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 Annex

Developer Simeon Janes created the “Toronto Annex” subdivision in 1886. The area was annexed to the City of Toronto the following year. Wealthy residents settled along the tree-lined streets, including Timothy Eaton of the Eaton’s department store family and George Gooderham Sr., president of Gooderham and Worts Distillery. Architect E.J. Lennox’s 1887 residence at 37 Madison Avenue established the template for what became known as the “Annex style” house, a distinctive blend of American Richardsonian Romanesque and British Queen Anne Revival, characterized by large rounded arches, turrets, and ornamental detailing.

By the early twentieth century, the upper classes had migrated northward to Forest Hill and Lawrence Park, and many Annex mansions were subdivided into rooming houses or acquired by the University of Toronto. The university’s expanding campus along the southern and eastern edges brought a student population that has shaped the neighbourhood’s demographics and cultural character ever since.

The defining moment in The Annex’s history came in the 1960s and early 1970s, when the proposed Spadina Expressway threatened to bisect the neighbourhood. Residents including urban theorist Jane Jacobs, who lived in The Annex, organized the “Stop Spadina Save Our City” campaign. Premier Bill Davis cancelled the expressway in 1971 in what is now considered a landmark moment in Canadian urban planning. Over 500 buildings in The Annex are currently protected by heritage designation, and the neighbourhood’s Victorian and Edwardian streetscape remains largely intact.

Residential Buildings in The Annex

The Annex’s condo inventory blends heritage conversions with boutique new-build condominiums. Large tower developments are limited by the neighbourhood’s heritage protections.

• One Bedford (1 Bedford Road). A 32-storey tower containing 254 condo units, developed by Lanterra Developments. Completed in 2011, designed by KPMB and Page and Steele, with pre-cast concrete and limestone. Penthouse units reach over 4,000 square feet.

• Exhibit Residences (200 Bloor Street West). A 32-storey tower containing 200 condo units, developed by Bazis International with Metropia and Plaza. Completed around 2016, designed as four stacked “boxes,” each slightly rotated.

• B.Streets Condos (783 Bathurst Street). A 9-storey building containing 195 condo units, developed by Lindvest. Completed in 2014, designed by Hariri Pontarini Architects at the Bloor and Bathurst intersection.

• The Loretto (385 Brunswick Avenue). A 5-storey heritage conversion of the 1914 Loretto Abbey Day School, containing 50 condo units, developed by Context Development. Completed in 2007 with units ranging from 586 to 5,570 square feet.

• Madison Avenue Lofts (380 Macpherson Avenue). A 6-storey building containing 211 condo units, developed by Burnac Corporation. Completed in 2009 as a conversion of a 1950s Toronto Hydro warehouse with art deco styling.

• Schoolhouse Residences (391 Brunswick Avenue). A 4-storey boutique building containing 19 condo units, developed by Empire Communities. Completed in 2011 as a conversion of the former Loretto College School building.

Buildings Under Construction

New development in The Annex navigates the neighbourhood’s heritage protections through adaptive reuse and contextual design.

• Cielo Condos (300 Bloor Street West, Toronto, ON M5S 1W3). A 29-storey, 349-unit development by Collecdev and Northrop Development, designed by KPMB. Incorporates the restored Bloor Street United Church, a neo-Gothic heritage building, connected via a low-rise atrium. Under construction, with estimated completion in 2026.

• The Bedford (287 Davenport Road, Toronto, ON M5R 1J9). A 13-storey, 64-to-90-unit development by Burnac, designed by AUDAX with interiors by Studio Paolo Ferrari. Parisian Haussmann-inspired design with units ranging from 1,295 to 4,251 square feet. Under construction, with estimated completion in 2027 to 2028.

• 171 Lowther Avenue (171 Lowther Avenue, Toronto, ON). An 11-storey, 64-unit development by Raleigh Residences. Features a “finned” balcony design inspired by architect Uno Prii and adaptive reuse of a heritage house at the podium level. Pre-construction.

Each new building adds rental inventory that requires professional oversight from day one. For landlords purchasing pre-construction units as investments, the management partner they select before occupancy will determine how the first year of tenancy unfolds.

Market Prices: Renting and Buying in The Annex

What does it cost to rent or own in The Annex? MLS activity tracked through TRREB district C02 provides a clear picture for investors evaluating yield against acquisition cost.

Rental prices. The average monthly rent for a condo unit in The Annex ranges from $2,250 for a one-bedroom to approximately $3,500 for a two-bedroom. The neighbourhood commands a significant premium over the Toronto-wide average, driven by its heritage character, walkability, transit access, and proximity to the University of Toronto. Heritage loft conversions and larger units in buildings like The Loretto and One Bedford command the upper end of the range.

Sale prices. The average condo price per square foot in The Annex sits at approximately $972 in early 2026. The neighbourhood’s boutique condo inventory and heritage conversions skew the average listing price higher than the Toronto-wide condo average. For investors, the Annex’s constrained development pipeline and heritage protections limit new supply, which supports both rental demand and resale value over time.

Current Listings Managed by Buttonwood

Buttonwood manages rental properties across The Annex’s residential buildings, from heritage conversions at The Loretto to established condo buildings at One Bedford and B.Streets. Current availability changes throughout the year; visit the Buttonwood listings page for up-to-date inventory.

How Tenants Commute from The Annex

Walk Score data rates The Annex at 94 out of 100 for walkability (Walker’s Paradise), 97 out of 100 for transit (Rider’s Paradise), and 90 out of 100 for cycling (Biker’s Paradise). Three subway stations within the neighbourhood contribute to the near-perfect transit score.

Public transit. Spadina Station serves both Line 1 (Yonge-University) and Line 2 (Bloor-Danforth), providing connections in all four directions. St. George Station, also serving both lines, anchors the eastern edge. Bathurst Station on Line 2 anchors the western edge. The 7 Bathurst bus provides north-south service along the western boundary, and the 127 Davenport bus runs east-west along the northern edge.

Cycling. Dedicated cycling infrastructure on Bloor Street West provides protected east-west access through the neighbourhood.

Driving. Avenue Road and Bathurst Street provide north-south access to Highway 401 and the Gardiner Expressway.

Schools in The Annex

Families renting in The Annex have access to TDSB schools within the neighbourhood.

Huron Street Junior Public School (541 Huron Street, JK-6) is located in the heart of The Annex.

Jesse Ketchum Junior and Senior Public School (61 Davenport Road, JK-8) serves the northeastern portion of the neighbourhood near Avenue Road and Davenport.

Harbord Collegiate Institute (286 Harbord Street, Grades 9-12) is located at the southern edge of The Annex and has served the neighbourhood since its founding.

Toronto Western Hospital (University Health Network, 399 Bathurst Street), a full-service teaching hospital with an emergency department, is located at the southwestern corner of the neighbourhood at Bathurst and Dundas.

How Buttonwood Manages Annex 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 phenomenal 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 Annex’s rental market draws a mix of university-affiliated professionals, academics, and established residents who value the neighbourhood’s heritage character and central location.

Working with Annex Landlords

Landlords who own a condo unit in The Annex, whether at One Bedford, a heritage conversion at The Loretto, or a loft at Madison Avenue Lofts, are managing a premium asset in one of Toronto’s most established and heritage-protected neighbourhoods. The management partner they choose should reflect that.

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

The heritage streetscape, the University of Toronto campus, the Bloor Street commercial corridor, three subway stations, and over 500 heritage-designated buildings all contribute to a quality-of-life profile that draws tenants who stay. The Annex’s appeal is structural, rooted in academic culture, transit access, and architectural character that are not moving.

Heritage protections limit new development, which means rental inventory in The Annex grows slowly. That scarcity supports both rental rates and occupancy for well-managed properties. Buttonwood has spent 14 years developing the processes that keep vacancy low and tenancy outcomes predictable across the GTA.

Our midtown portfolio extends beyond The Annex. We manage investment properties in Yorkville to the east, Summerhill to the northeast, Casa Loma to the north, and Trinity Bellwoods to the south.

Contact Buttonwood to discuss management of your Annex investment property. Whether you own a heritage loft conversion or a condo unit in one of the neighbourhood’s newer buildings, we can provide a direct assessment of what your property requires.