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82 Chestnut Park Road — Detached

For Sale

Toronto C09, ON M4W 2R3

5 Bed · 6 Bath · Detached

MLS #C13227720

$12,500,000

Listed Price

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!

Property Details

Bedrooms

5

Bathrooms

6

Square Feet

5000 + sqft

Property Type

Detached

Style3-Storey
Approx. Age100+ years
Lot Size86 143 ft
Frontage85.5 ft
Depth142.9 ft
GarageAttached
BasementFinished
CoolingCentral Air
HeatingWater
FireplaceYes
PoolInground
Parking Spaces4
Listed OnMay 31, 2026
MLS Size5000 +
Property Tax$52,794/year

Rooms

NameSize (m)Size (ft)Features
Foyer(Main)2.31 x 1.77.6 x 5.6-
Foyer(Main)2.31 x 1.77.6 x 5.6-
Foyer(Main)2.31 x 1.77.6 x 5.6-
Living Room(Main)5.18 x 4.8817.0 x 16.0-
Living Room(Main)5.18 x 4.8817.0 x 16.0-
Living Room(Main)5.18 x 4.8817.0 x 16.0-
Dining Room(Main)5.31 x 4.8817.4 x 16.0-
Dining Room(Main)5.31 x 4.8817.4 x 16.0-
Dining Room(Main)5.31 x 4.8817.4 x 16.0-
Family Room(Main)7.11 x 4.0623.3 x 13.3-
Family Room(Main)7.11 x 4.0623.3 x 13.3-
Family Room(Main)7.11 x 4.0623.3 x 13.3-
Kitchen(Main)5.79 x 3.4819.0 x 11.4-
Kitchen(Main)5.79 x 3.4819.0 x 11.4-
Kitchen(Main)5.79 x 3.4819.0 x 11.4-
Breakfast(Main)6.45 x 3.7621.2 x 12.3-
Breakfast(Main)6.45 x 3.7621.2 x 12.3-
Breakfast(Main)6.45 x 3.7621.2 x 12.3-
Primary Bedroom(Third)11.02 x 6.2536.2 x 20.5-
Primary Bedroom(Third)11.02 x 6.2536.2 x 20.5-
Primary Bedroom(Third)11.02 x 6.2536.2 x 20.5-
Bedroom 2(Second)7.62 x 4.2725.0 x 14.0-
Bedroom 2(Second)7.62 x 4.2725.0 x 14.0-
Bedroom 2(Second)7.62 x 4.2725.0 x 14.0-
Bedroom 3(Second)4.11 x 3.5813.5 x 11.7-
Bedroom 3(Second)4.11 x 3.5813.5 x 11.7-
Bedroom 3(Second)4.11 x 3.5813.5 x 11.7-
Bedroom 4(Second)6.5 x 4.8821.3 x 16.0-
Bedroom 4(Second)6.5 x 4.8821.3 x 16.0-
Bedroom 4(Second)6.5 x 4.8821.3 x 16.0-
Bedroom 5(Lower)5.59 x 4.8818.3 x 16.0-
Bedroom 5(Lower)5.59 x 4.8818.3 x 16.0-
Bedroom 5(Lower)5.59 x 4.8818.3 x 16.0-
Recreation(Lower)5.18 x 4.8817.0 x 16.0-
Recreation(Lower)5.18 x 4.8817.0 x 16.0-
Recreation(Lower)5.18 x 4.8817.0 x 16.0-

82 Chestnut Park Road History

Complete transaction history for this property

Expired

Listed: May 27, 2025

$13,950,000

345 days on marketSale
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Home Features

Property TypeDetached
Style3-Storey
Approx. Age100+ years
Lot Size86 × 143 ft
Frontage85.5 ft
Depth142.9 ft
GarageAttached
BasementFinished
CoolingCentral Air
FireplaceYes
PoolInground

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About 82 Chestnut Park Road, Toronto C09, ON M4W 2R3

82 Chestnut Park Road, Toronto C09, ON M4W 2R3 is a 5-bedroom, 6-bathroom 3-storey detached with approximately 5000 + square feet of living space, situated on a 86 143 foot lot. This property is currently for sale at $12,500,000. The home features a attached garage and a finished basement, built approximately 100+ years ago.

Rosedale-Moore Park Neighbourhood

This home is located in Rosedale-Moore Park, part of Toronto C09 in the Toronto area. Explore more homes for sale and recently sold properties in this neighbourhood.

Whether you are looking to buy, sell, or lease in Rosedale-Moore Park, our team of experienced real estate professionals can help you navigate the market and find the perfect home. Contact us today for a free consultation.

82 Chestnut Park Road, Toronto C09, ON M4W 2R3

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