Rosedale Property Management

Rosedale is bounded by the Canadian Pacific Railway corridor to the north, Bloor Street East to the south, Bayview Avenue to the east, and Yonge Street to the west. The neighbourhood occupies a ravine-laced plateau in midtown Toronto, split into North Rosedale and South Rosedale by the Rosedale Valley Road. Its residential stock ranges from nineteenth-century detached mansions on deep lots to boutique condominiums and co-operative apartment buildings along the southern and western perimeter streets. That housing profile makes Rosedale property management a discipline that requires both heritage-home oversight and condominium-unit coordination within a single portfolio.

The neighbourhood falls under TRREB district C09 (Rosedale-Moore Park) in the Toronto Regional Real Estate Board’s MLS system. Buttonwood Property Management has managed investment properties in the C09 corridor since 2011. Each lease 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 Rosedale

Rosedale takes its name from the estate of Sheriff William Botsford Jarvis, who purchased 120 acres of land north of Bloor Street in 1824. His wife Mary named the property “Rosedale” after the wild roses that grew across the hillsides. Jarvis was appointed High Sheriff of the Home District in 1827, and by 1835 he had expanded the estate with wings designed by architect John Howard, adding bedrooms, a morning room, a verandah, and a conservatory. The original Rosedale house stood at the intersection of Cluny Drive and Rosedale Road until 1905.

William Jarvis died in 1864 and the remaining estate was sold to David Macpherson, who subdivided the land into residential lots. Rosedale became Toronto’s first “garden suburb,” and it was the first area in Canada to incorporate curved streets into its subdivision plan. South Rosedale was largely built out by the early 1900s, while North Rosedale developed through the 1910s and 1920s. The neighbourhood’s ravine geography preserved much of its original tree canopy and determined the winding street layout that remains today.

The Housing Stock in Rosedale

The dominant housing types in Rosedale are two-storey and three-storey detached brick homes. Architectural styles span Victorian, Edwardian, Georgian, Tudor Revival, and Arts and Crafts, with most surviving homes dating from the 1880s to the 1930s. Lot sizes in North Rosedale are among the largest in the City of Toronto, with many properties exceeding 50 feet of frontage on streets like Cluny Drive, Elm Avenue, and Highland Avenue.

South Rosedale contains a number of condominium, co-operative, and co-ownership apartment buildings concentrated along Dale Avenue, Roxborough Street East, Park Road, and Bloor Street East. These buildings range from four-storey boutique residences to towers exceeding 20 storeys. A small number of purpose-built rental buildings also serve the neighbourhood, providing walk-up apartments and mid-rise units.

Rental inventory in Rosedale consists of whole-house rentals, and rental units in low-rise and mid-rise buildings. 

Residential Buildings in Rosedale

Rosedale’s housing stock is dominated by detached homes, but a collection of condominium and co-operative buildings along the neighbourhood’s perimeter streets provides the primary source of apartment-style inventory.

• The Rosedale on Bloor (395 Bloor Street East). A 52-storey condominium tower with 476 suites, developed by Gupta Group and completed in 2024. Suites range from 307 to 2,200 square feet. The building integrates a Canopy by Hilton hotel on its lower floors, with residential units occupying the upper storeys. Located at the Bloor and Sherbourne intersection on the neighbourhood’s southern edge.

• The Bellagio (300 Bloor Street East). A 24-storey condominium built in 2002 by Pinnacle International with approximately 279 suites. Unit sizes range from 515 to 3,100 square feet, including one-bedroom, two-bedroom, and three-bedroom layouts. Situated on the Bloor Street corridor near the Sherbourne Street intersection.

• 8 Park Road (8 Park Road). A 28-storey condominium developed by Minto Group Inc. and H&R Developments, completed in 2003. The first seven floors contain retail space, with approximately 297 residential suites occupying the upper storeys. Designed by Page & Steele Architects, the building sits one block north of Bloor and Yonge.

• No. 7 Rosedale (7 Dale Avenue). A 4-storey, 26-unit ultra-luxury condominium developed by Platinum Vista with architecture by Hariri Pontarini Architects and interiors by Studio Munge. Completed in 2024. Suites overlook the Rosedale ravine, with two-bedroom residences starting at $7,149,000.

• Two Roxborough East (2 Roxborough Street East). A 7-storey, 35-unit boutique condominium completed in 2001 by Diamante Development Corporation. Suites range from 799 to 2,544 square feet, with wraparound balconies overlooking Rosedale’s tree canopy. The building includes concierge, a fitness facility, and visitor parking.

• The Roxborough (66 Roxborough Street East). A 4-storey, 10-unit boutique condominium built in 1983. Suites range from approximately 700 to 1,300 square feet, offering one-bedroom and two-bedroom layouts on a quiet residential street in South Rosedale.

• Kensington Apartments (21 Dale Avenue). A 4-storey co-operative building on landscaped grounds in South Rosedale, with suites ranging from bachelor to three-bedroom layouts (400 to over 2,600 square feet). Amenities include indoor and outdoor swimming pools, a party room, and 24-hour concierge. Several suites offer ravine views.

Buildings Under Construction

Rosedale’s interior streets are fully built out, but development along the neighbourhood’s perimeter corridors is adding approximately 436 new residential units to the pipeline through pre-construction and active construction projects.

• 1 Marlborough (1140 Yonge Street, Toronto, ON M4W 0A8). A 13-storey, 58-unit luxury condominium by Devron and Dorsay Development Corporation, located at the Rosedale-Summerhill border. Suites start at 1,800 square feet, with prices beginning in the high $3 millions. The building incorporates heritage elements from the original Pierce-Arrow showroom on the site. Pre-construction, with launch anticipated in mid-2026 and completion targeted for 2029.

• 1087 Yonge Street (1087 Yonge Street, Toronto, ON M4W 2L5). A 35-storey, 235-unit condominium by Zinc Developments at the Yonge Street and Summerhill corridor. The building includes a six-storey podium base with stepped-back upper floors. Pre-construction.

• Park Road Condos (Park Road at Bloor Street East). A pre-construction residence by Capital Developments on the eastern edge of Yorkville, overlooking the Rosedale Valley Ravine. Architecture by Diamond Schmitt with interiors by Cecconi Simone. Pre-construction.

For those buyers, the management partner selected before occupancy will shape how the real estate asset performs over time to ensure optimal return on investment.

Market Prices: Renting and Buying in Rosedale

Whole-house rentals for detached homes in Rosedale typically range from $5,000 to $12,000 per month depending on size, condition, and ravine proximity. The median rent in Rosedale sits approximately 44% above the national average. One-bedroom condominium units generally command $2,200 to $2,800, while two-bedroom units range from $2,800 to $3,800.

The purchase market in Rosedale’s TRREB C09 district averaged approximately $2.85 million across all property types in late 2024, with the detached benchmark price reaching $3,687,200 in 2025. Renovated homes on ravine-backing lots in North Rosedale routinely trade above $5 million. The neighbourhood’s household income base supports stable property values and a tenant pool composed primarily of established professionals, senior executives, and families with school-age children.

How Tenants Commute from Rosedale

Walk Score rates central Rosedale at 93 out of 100, classifying the neighbourhood as a “Walker’s Paradise.”

Public transit. Rosedale Station on TTC Line 2 (Bloor-Danforth) is located at the intersection of Crescent Road and Rosedale Valley Road, providing direct subway access to downtown and the east end. Sherbourne Station on Line 2 serves the neighbourhood’s southeastern corner at Bloor and Sherbourne. The 82 Rosedale bus connects interior residential streets (South Drive, Crescent Road, Glen Road, Elm Avenue) to Rosedale Station and Castle Frank Station. The 75 Sherbourne bus runs north-south along Sherbourne Street, and the 97 Yonge bus provides service along the western boundary.

Cycling. The Rosedale Valley Road bike lane connects the neighbourhood directly to the Don Valley trail system and Bayview Avenue. Cyclists heading downtown can reach the Financial District in under 20 minutes via the ravine route.

Driving. Bayview Avenue provides direct access to the Don Valley Parkway for commuters heading to Highway 401 or downtown. Mount Pleasant Road connects north to Eglinton Avenue, and Jarvis Street runs south through the downtown core.

Schools in Rosedale

Families renting in Rosedale have access to TDSB schools that consistently rank among the top in the city.

Rosedale Junior Public School (22 South Drive, JK-6) has served the neighbourhood since 1891, providing over a century of academics, arts enrichment, and community involvement. The school draws families specifically to South Rosedale.

Whitney Junior Public School (119 Rosedale Heights Drive, JK-6) serves both Rosedale and Moore Park. The school is located on the elevated ridge between the two neighbourhoods and is a primary draw for families with young children.

Rosedale Heights School of the Arts (711 Bloor Street East, Grades 9-12) is a TDSB secondary school with a specialized arts program offering dance, dramatic arts, instrumental and vocal music, visual arts, and media arts. The school does not audition for entry, making it accessible to all secondary students in the catchment.

How Buttonwood Manages Rosedale Properties

Tenant screening is where outcomes are determined. The process Buttonwood uses was developed across thousands of tenancies throughout the GTA since 2011. That track record reflects the precision of our screening processes and procedures. Rosedale attracts established professionals, senior executives relocating to Toronto, young families drawn by the TDSB schools, and international investors purchasing heritage properties as long-term investors.

Once a qualified tenant is placed, management covers rent collection, maintenance coordination, lease renewal tracking, and annual rent increase notices 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.

Managing detached houses and condo units in Rosedale requires direct oversight: this requires deep expertise and Buttonwood offers a comprehensive end-to-end solution to real estate investors.

Working with Rosedale Landlords

Rosedale’s mix of heritage detached homes, boutique co-operatives, and condominium towers creates a landlord base with varied management needs. Whether the property is a whole-house rental on Cluny Drive, a co-operative suite on Dale Avenue, or a condo unit in a high-rise along Bloor Street East, the management principles are the same: rigorous screening, transparent reporting, and direct open communication.

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 Built on Ravines and Legacy

Rosedale’s park system is its most defining residential feature. Craigleigh Gardens, a secluded eight-acre park on the former estate of Sir Edmund Boyd Osler, was donated to the City of Toronto in 1924 and opened to the public in 1926. Chorley Park, the site of Ontario’s fourth Government House (built 1915, demolished 1961), now serves as public parkland overlooking the Don Valley. David A. Balfour Park follows Yellow Creek through the ravine system, connecting to the Rosedale Valley Trail and the broader Don Valley path network. Rosedale Park, the neighbourhood’s central green space, hosted the first Grey Cup game in 1909 and remains a community gathering point with sports fields and a playground.

Renters in Rosedale stay longer than the Toronto average because the combination of green spaces and ravine access, top-ranked schools, and walkable transit creates residential quality that is difficult to replicate elsewhere in the city.

Our midtown portfolio extends beyond Rosedale. We manage investment properties in Moore Park to the north, Summerhill along the Yonge corridor, and Deer Park to the west.

Contact Buttonwood to discuss management of your Rosedale investment property.