266 Douglas Drive
Toronto C09, ON
- 5 bed
- 6 bath
- approx. 3500-5000 sqft
- Detached
- 4 days on market
One of North Rosedale's most admired and coveted estate residences, originally built in 1921, has undergone a complete transformation and expansion under the meticulous care of Karen Kayne Design. Directly facing the lawns and lush mature trees of Chorley Park, this magnificent residence sits on an extraordinary 62 by 235-foot lot spanning a full one-third of an acre. A large covered front verandah offers a peaceful vantage point to enjoy the surrounding green landscape. Inside, approximately 5,825 sq ft of total living space (across all levels) gracefully combines classic architecture with a warm atmosphere of refinement. Top-tier finishes abound. The chef's kitchen has a La Cornue range at its centre, along with 2 Sub Zero fridges and 2 Miele dishwashers. Formal and casual dining can be enjoyed both indoors and out. The ultra-private and exceptionally deep back garden (with magnificent trees, hedges and plantings) serves as a remarkable outdoor oasis, carefully crafted for both quiet relaxation and formal entertaining. Square-cut Hampton limestone terraces and stone patios frame a heated inground concrete pool, complete with an integrated hot tub and two dedicated change rooms. An intimate covered dining terrace overlooks the pool. Stellar construction standards are evident throughout, highlighted by exceptional windows and doors. Winters are managed easily thanks to 2 fireplaces and the attached heated garage (with custom built-ins) for 2 tandem cars, paired with a heated concrete driveway accommodating four additional vehicles. In-floor heating in every room. Coveted public and Catholic schools are within easy walking distance, as is top rated K-12 Branksome Hall for girls. Daily errands and gourmet provisions are a short walk away to Summerhill Market. Step onto the Beltline Trail to jog or walk the dog through scenic nature trails, taking you straight down to the vibrant Saturday farmers' market at Evergreen Brick Works.
Listing Details
- Taxes (2026)
- $32,480
- Listed
- September 14, 2026
Price History
Property
- Style
- 2-Storey
- Age
- 100+
- Construction
- Brick, Stucco (Plaster)
- Roof
- Asphalt Shingle
- Foundation
- Poured Concrete, Slab
- Interior
- Carpet Free, Generator - Partial
- Lot Size
- 62.25 x 235 Feet
Parking
- Garage
- Attached
- Covered Spaces
- 2
- Total Parking
- 6
Utilities
- Sewer
- Sewer
- Heat Source
- Gas
Location & Legal
- Cross Street
- East of Mt Pleasant
- Zoning
- Residential
- Parcel Number
- 103931307
- Possession
- Other
- Occupancy
- Owner
Included
- Inclusions
- See Schedule B
- Exclusions
- See Schedule B
- Rental Items
- NONE
Schools
Elementary
- Whitney Junior Public School0.6 km
Public · Toronto DSB · 420 students
Grade 3 reading: 93% met the provincial standard · Grade 6 math: 88% met the provincial standard
- Bennington Heights Elementary School0.9 km
Public · Toronto DSB · 160 students
Grade 3 reading: 67% met the provincial standard · Grade 6 math: 74% met the provincial standard
- Our Lady of Perpetual Help Catholic School1 km
Catholic · Toronto CDSB · 330 students
Grade 3 reading: 90% met the provincial standard · Grade 6 math: 80% met the provincial standard
Secondary
- CALC Secondary School1.5 km
Public · Toronto DSB · 565 students
- Rosedale Heights School of the Arts1.5 km
Public · Toronto DSB · 945 students
Grade 10 literacy: 95% met the provincial standard
- Msgr Fraser College (Isabella Campus)1.9 km
Catholic · Toronto CDSB · 345 students
Straight-line distance. Nearby schools are not necessarily the assigned schools — confirm catchment with the school board. Scores are EQAO provincial test results for 2024-2025.
Community
Postal area M4W
- Population
- 15,296
- Private dwellings
- 9,238
- Median age
- 44.8
- Average household size
- 1.9
- Median household income
- $104,000
Source: Statistics Canada, 2021 Census of Population, catalogue 98-401-X2021013. Adapted from Statistics Canada. This does not constitute an endorsement by Statistics Canada of this product.
Local market
Residential Freehold in Toronto C09 · last 12 months
- Median sold price
- $1,820,000
- Homes sold
- 232
- Median days on market
- 25
- Sale-to-list price
- 95.9%
Based on 232 recorded sales of residential freehold properties in Toronto C09 over the last 12 months.
Listed by
SOTHEBY'S INTERNATIONAL REALTY CANADA
Walk Score
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Location
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Mortgage Calculator
$2,199,000
Estimated Monthly Payment
$54,015
Land transfer tax
Ontario land transfer tax only. An estimate — not legal or financial advice. Municipal land transfer tax applies in Toronto and is not included.
Investment Analysis
No recent nearby lease data. Enter a rent to see the numbers.
Mortgage: $54,015/mo (20% down, 5.5%)
Taxes: $2,707/mo · Insurance: $2,749/mo
Estimates only. Consult a financial advisor.
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