82 Chestnut Park Road
Toronto C09, ON
- 5 bed
- 6 bath
- approx. 5000 + sqft
- Detached
- 102 days on market
Extremely rare endless summer escape in a poolside paradise with 7-Star resort-style luxury! Experience the ultimate retreat in the most sought-after and prestigious Rosedale neighborhood, west of Mt. Pleasant. Embraced by mature trees and manicured lawns, this extraordinarily expansive 85-foot-wide tableland property sits atop the exclusive Chestnut Park ravine, overlooking serene parkland below and feels like a private country estate. A true garden oasis, the stunning oversized pool is virtually irreplaceable in this area, creating an idyllic opportunity for captivating family living and exceptional entertaining. Spanning nearly 8,000 square feet, this elegant Georgian residence is in a picture-perfect position on this magically lamp-lit street just 2 blocks from Yonge. The garden features sprawling multiple terraces for sitting, dining, and entertaining, complete with an outdoor kitchen. Inside, discover gracefully curated interiors & a truly sumptuous sky-lit primary suite with lush treetop views, a sitting area with fireplace, his & her separate dressing rooms and spa-inspired ensuite. This sleek trophy property blends transitional modernity, alluring charm & unparalleled privacy with modern convenience and spectacular luxury in a truly prized neighborhood. Additional highlights include an ELEVATOR, generator, garage with lift & ensuite bathrooms in all bedrooms for superb flexibility. Set beneath a treed canopy for total privacy, you are just steps from the subway, excellent private & public schools, premier shopping, area parks, tennis, skating & hiking & biking trails extending to the lake with Yorkville & the city center only a 10-minute drive away. For those who value permanence, treasured memories will resonate for all in this enduring and stable investment!
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Listing Details
- Taxes (2025)
- $52,794
- Listed
- June 1, 2026
Price History
Listing history
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Property
- Style
- 3-Storey
- Age
- 100+
- Construction
- Brick
- Roof
- Slate
- Foundation
- Unknown
- Interior
- Central Vacuum
- Lot Size
- 85.55 x 142.88 Feet
Parking
- Garage
- Attached
- Covered Spaces
- 2
- Total Parking
- 4
Utilities
- Sewer
- Sewer
- Heat Source
- Gas
Location & Legal
- Cross Street
- Roxborough/Mount Pleasant
- Parcel Number
- 211190148
- Possession
- 60-89 days
- Occupancy
- Owner
Schools
Elementary
- Rosedale Junior Public School0.3 km
Public · Toronto DSB · 220 students
Grade 3 reading: 95% met the provincial standard · Grade 6 math: 100% met the provincial standard
- Our Lady of Perpetual Help Catholic School0.8 km
Catholic · Toronto CDSB · 330 students
Grade 3 reading: 90% met the provincial standard · Grade 6 math: 80% met the provincial standard
- Whitney Junior Public School0.9 km
Public · Toronto DSB · 420 students
Grade 3 reading: 93% met the provincial standard · Grade 6 math: 88% met the provincial standard
Secondary
- Msgr Fraser College (Isabella Campus)1.3 km
Catholic · Toronto CDSB · 345 students
- Rosedale Heights School of the Arts1.6 km
Public · Toronto DSB · 945 students
Grade 10 literacy: 95% met the provincial standard
- Jarvis Collegiate Institute1.7 km
Public · Toronto DSB · 610 students
Grade 10 literacy: 80% met the provincial standard
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
- 234
- Median days on market
- 25
- Sale-to-list price
- 95.9%
Based on 234 recorded sales of residential freehold properties in Toronto C09 over the last 12 months.
Rooms
2 × 5-piece, 4-piece, 2 × 3-piece, 2-piece
Third
- Primary Bedroom
Second
- Bedroom 225' x 14'
- Bedroom 313'6" x 11'9"
- Bedroom 421'4" x 16'
Main
- Breakfast21'2" x 12'4"
- Dining Room17'5" x 16'
- Family Room23'4" x 13'4"
- Foyer7'7" x 5'7"
- Kitchen19' x 11'5"
- Living Room17' x 16'
Lower
- Bedroom 518'4" x 16'
- Recreation17' x 16'
Listed by
CHESTNUT PARK REAL ESTATE LIMITED
Walk Score
Walk
Transit
Bike
Scores by Walk Score®
Location
Street View
Mortgage Calculator
$2,500,000
Estimated Monthly Payment
$61,409
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: $61,409/mo (20% down, 5.5%)
Taxes: $4,399/mo · Insurance: $3,125/mo
Estimates only. Consult a financial advisor.
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