82 Chestnut Park Road, Toronto, ON M4W 2R3, Toronto C09, ON
Bed 5
Bath 6
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!
Property Highlights
For Sale
MLS NO.
C13227720
Type
Residential Freehold
Sub Type
Detached
Bedrooms
5
Bathrooms
6
Parking
4.0
Garage
Yes
Complete Property Details
Property Type
Residential Freehold
Sub Type
Detached
Transaction Type
For Sale
Status
Active
Contract Status
Available
MLS® Number
C13227720
Living Area Range
5000 +
Total Bedrooms
5
Bedrooms Above Grade
4
Bedrooms Below Grade
1
Total Bathrooms
6
Total Kitchens
1
Kitchens Above Grade
1
Rooms Above Grade
10
Rooms Below Grade
2
Interior Features
Central Vacuum
Fireplace
Yes
Central Vacuum Yn
Yes
Construction
Brick
Roof
Slate
Lot Width
85.55
Parking Features
Private
Parking Total
4.0
Covered Spaces
2.0
Garage Type
Attached
Garage
Yes
Pool
Inground
Direction Facing
East
Cooling
Central Air
Heat Source
Gas
Heat Type
Water
Internet Address Display Yn
Yes
Internet Entire Listing Display Yn
Yes
Full Address
82 Chestnut Park Road, Toronto, ON M4W 2R3
City
Toronto C09
Neighbourhood
Rosedale-Moore Park
County / Region
Toronto
Province / State
ON
Postal Code
M4W 2R3
Cross Street
Roxborough/Mount Pleasant
Directions
North on Chestnut Park from Roxborough Street East
List Price
$12,500,000
Annual Taxes
$52,794
Tax Year
2025
Legal Description
See Schedule B
Possession Type
60-89 days
Possession Details
60 days / TBD
Listing Office
CHESTNUT PARK REAL ESTATE LIMITED
Board
Toronto Regional Real Estate Board
Original Entry
2026-06-02T14:42:26Z
Media Updated
2026-06-08T14:24:32Z
Photos Updated
2026-06-02T14:42:27Z
Last Modified
2026-06-08T14:26:05Z
System Modified
2026-06-08T14:26:15.468206Z
MLS Status
New
Architectural Style
3-Storey
Basement
Finished
Ddfyn
Yes
Expiration Date
2026-11-20
Foundation Details
Unknown
Heat Source Multi
Gas
Heat Type Multi
Water
Hstapplication
Included In
Link Yn
No
Occupant Type
Owner
Originating System Id
A00001796
Parcel Number
211190148
Parking Spaces
3
Property Features
Public Transit, Park, Place Of Worship, School, Rec./Commun.Centre
Public Remarks
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!
