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Detached for sale at 82 Chestnut Park Road, Toronto C09 - 5 bedroom, 6 bathroom - Photo 1 of 31
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$13,950,000

82 Chestnut Park Rd

Toronto C09, ON M4W 2R3

82 Chestnut Park Rd, Toronto C09 — Listed at $13,950,000. 5 bedroom, 6 bathroom 3-Storey Detached. MLS® C12178239.

5Beds
6Baths
5000 +sqft
Detached
3-Storey
4Parking
$52,793.63Taxes/yr · 2025
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Description

Endless Summer in a Poolside Paradise with 7-Star Resort-Style Luxury! Experience the ultimate retreat in the highly sought-after Rosedale neighborhood, west of Mt. Pleasant. This expansive 85-foot-wide tableland property sits atop the exclusive Chestnut Park ravine, overlooking serene parkland below. A true garden oasis, the stunning oversized pool is virtually irreplaceable in this area, creating an idyllic opportunity for a captivating & private escape. 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 home features stunning multiple terraces for sitting, dining, and entertaining, complete with an outdoor kitchen. Inside, discover serene, curated interiors & an exceptionally sumptuous primary suite with his & her separate dressing rooms. This trophy property blends timeless grace, alluring charm, & unparalleled privacy with the convenience of everyday luxury in a prized neighborhood. Additional highlights include an ELEVATOR, generator, garage with lift, & ensuite bathrooms in all bedrooms. Set beneath a lush, treed canopy, you are just steps from the subway, top private & public schools, premier shopping, area parks, tennis, skating & hiking & biking trails extending to the lake. Plus, Yorkville & the city center are only a 10-minute drive away.

Property Details

Property TypeDetached
Style3-Storey
CommunityRosedale-Moore Park
Approximate Age100+
Rooms10+2
Kitchens1
Washrooms6
Square Feet5000 + sqft
Lot Dimensions56.37 × 142.88 ft
Fronting OnEast
Dir/Cross StRoxborough/Mount Pleasant
Garage TypeAttached
Garage Parking Spaces2
DrivePrivate
Parking Drive Spaces2
Total Parking Spaces4
ExteriorBrick
RoofSlate
FoundationUnknown
BasementFinished
Fireplace FeaturesYes
Heating TypeWater
Heating SourceGas
A/CCentral Air
SewersSewer
PoolInground
Taxes (2025)$52,793.63
HSTIncluded In
Listed Date5/28/2025
Days on Market533 days
Possession60 Days / TBD

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Listing Courtesy of: CHESTNUT PARK REAL ESTATE LIMITED

MLS® #C12178239

TRREBMLS®

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 REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.

© 2026 Toronto Regional Real Estate Board. All rights reserved.

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HouseIndex Take: 82 Chestnut Park Road

This detached (3-Storey) is located in the Rosedale-Moore Park neighbourhood of Toronto.

The home offers 5+1 bedrooms, 6 bathrooms.

Features include a finished basement, 4 parking spaces including a 2-car garage, a fireplace.

Additional details: lot dimensions of 56.37 × 142.88 feet.

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About Toronto Real Estate

This Detached is located in the Rosedale-Moore Park community in Toronto. Toronto is Canada's largest city and the economic hub of the Greater Toronto Area. With world-class transit, diverse neighbourhoods from the Annex to Scarborough, and proximity to major employers in the Financial District, it remains the most sought-after real estate market in Ontario. Buyers benefit from extensive GO Transit and TTC subway connectivity. Detached homes in Toronto are in high demand among families seeking space, privacy, and long-term equity growth.

TTC subway & streetcar networkWorld-class dining & entertainmentUniversity of Toronto & major hospitals nearbyWaterfront trails & ravine parks
Walkability: Highly walkable — many neighbourhoods score 80+ on Walk Score
View full Toronto neighbourhood guide →