82 Chestnut Park Road
Rosedale-Moore Park · Toronto C09 · ON · M4W 2R3
On market 110 days
About this property
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!
Key facts
Property details
Rooms & baths
Building & utilities
Parking
Lot
Financial
Features & amenities
Interior
Rooms
12 rooms on 4 level s
| Type | Dimensions | Features |
|---|---|---|
| Main | ||
| Foyer | 7'7" × 5'7" | Hardwood FloorDouble Closet |
| Living Room | 17' × 16' | FireplaceBay Window |
| Dining Room | 17'5" × 16' | Hardwood FloorFireplace |
| Family Room | 23'4" × 13'4" | FireplaceStone Floor |
| Kitchen | 19' × 11'5" | Eat-in KitchenCentre Island |
| Breakfast | 21'2" × 12'4" | FireplaceFrench Doors |
| Second | ||
| Bedroom 2 | 25' × 14' | FireplaceWalk-In Closet(s) |
| Bedroom 3 | 13'6" × 11'9" | Hardwood FloorDouble Closet |
| Bedroom 4 | 21'4" × 16' | Bay WindowHardwood Floor |
| Third | ||
| Primary Bedroom | 36'2" × 20'6" | SkylightHis and Hers Closets |
| Lower | ||
| Bedroom 5 | 18'4" × 16' | Window |
| Recreation | 17' × 16' | Window |
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Location
Market Overview
Toronto C09
Listing data provided by the Toronto Regional Real Estate Board (TRREB).
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The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The listing data is deemed reliable but is not guaranteed accurate by TRREB. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA.
Last updated: September 20, 2026.