82 Chestnut Park Road, Toronto, ON

Toronto, Central Toronto, Rosedale-Moore Park Hood
Roxborough/Mount Pleasant
4+1 Br | 6 Bath | 5000 + Sqft
$12,500,000 For Sale

Property Overview

  • Detached — 3-Storey
  • SqFt: | 5000 + Sqft
  • Lot Size: 85.55 x 142.88 Feet
  • Age: 100+ Years
  • Basement: Finished
  • Exterior: Brick
  • Taxes: 52,794 / 2025
  • Zoning: n/a
  • MLS #: C13227720
  • Sewer: Sewer
  • Heat Source: Gas , Water

Property Description

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 home features stunning multiple terraces for sitting, dining, and entertaining, complete with an outdoor kitchen.

Inside, discover serene, curated interiors & an exceptionally sumptuous sky-lit primary suite with lush treetop views, a sitting area with fireplace, his & her separate dressing rooms and spa-inspired ensuite. This trophy property blends timeless grace, 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 exceptional flexibility.

Set beneath a treed canopy for total privacy, you are just steps from the subway, top 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

  • For: For Sale
  • Type: Detached
  • Style: 3-Storey
  • Lot: 85.55 x 142.88 Feet
  • Region: Toronto
  • Hood: Rosedale-Moore Park
  • Zoning: n/a
  • Lot Irreg: West 56.37'
  • Fronting On: East

Building Details

  • Age: 100+ Years
  • Exterior: Brick
  • Heat: Gas , Water
  • A/C: Central Air
  • Interior Features: Central Vacuum
  • Pool: Inground
  • Sewer: Sewer
  • Garage: Attached
  • Total Parking: 4.00
  • Driveway: Private

Property Interior

  • Sqft: 5000 + Sqft
  • Bed: 4 +1
  • Bath: 6
  • Kitchen: 1
  • Family Room: No
  • Basement: Finished
Rooms Details

Foyer

Main Level

2.31 x 1.7

Hardwood Floor, Double Closet, Elevator

Living Room

Main Level

5.18 x 4.88

Fireplace, Bay Window, Hardwood Floor

Dining Room

Main Level

5.31 x 4.88

Hardwood Floor, Fireplace, Bay Window

Family Room

Main Level

7.11 x 4.06

Fireplace, Stone Floor, Walk-Out

Kitchen

Main Level

5.79 x 3.48

Eat-in Kitchen, Centre Island, B/I Appliances

Breakfast

Main Level

6.45 x 3.76

Fireplace, French Doors, W/O To Terrace

Primary Bedroom

Third Level

11.02 x 6.25

Skylight, His and Hers Closets, 5 Pc Ensuite

Bedroom 2

Second Level

7.62 x 4.27

Fireplace, Walk-In Closet(s), 5 Pc Ensuite

Bedroom 3

Second Level

4.11 x 3.58

Hardwood Floor, Double Closet, 3 Pc Ensuite

Bedroom 4

Second Level

6.5 x 4.88

Bay Window, Hardwood Floor, 4 Pc Bath

Bedroom 5

Lower Level

5.59 x 4.88

Window, 3 Pc Bath

Recreation

Lower Level

5.18 x 4.88

Window

Property Listed by: CHESTNUT PARK REAL ESTATE LIMITED
Virtual Tour: n/a

Home Valuation Estimate

What is 82 Chestnut Park Road, Toronto, ON worth in today’s Rosedale-Moore Park, Central Toronto market?

This HomeZira valuation preview helps buyers and sellers think through the asking price for this 4-bedroom Detached with 5000 + sq. ft. in Rosedale-Moore Park, Central Toronto. The full estimate reviews the property’s location, home type, bedroom count, size range, age, and nearby comparable market activity after sign-in.

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Location

  • Address: 82 Chestnut Park Road
  • Neighborhood: Rosedale-Moore Park
  • Zip/Postal Code: M4W 2R3
  • Nearby Amenities: Public Transit, Park, Place Of Worship, School, Rec./Commun.Centre
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About 82 Chestnut Park Road, Toronto C09, ON M4W 2R3, Central Toronto

Located at 82 Chestnut Park Road, Toronto, ON in Central Toronto (Rosedale-Moore Park neighbourhood), near Roxborough/Mount Pleasant. This freehold home offers Detached, ["3-Storey"], 4 bedrooms, 6 bathrooms and 5000 + sq.ft. (approx.) in a layout suited to everyday family living. Basement: Finished • 4 parking spots • Garage: Attached • Heating: Gas Water • Cooling: Central Air. Property taxes are approximately $52,794 for 2025. 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-.

FAQs for 82 Chestnut Park Road, Toronto, ON , Rosedale-Moore Park , Central Toronto

What are the listing details for 82 Chestnut Park Road, Toronto, ON?
82 Chestnut Park Road, Toronto, ON is a Detached for sale in Central Toronto, in the Rosedale-Moore Park neighbourhood, Toronto. The current list price is $12,500,000. MLS number: C13227720.
How many bedrooms and bathrooms does this home have?
82 Chestnut Park Road, Toronto, ON is listed as a Detached with a ["3-Storey"] style, featuring 4+1 bedroom(s) and 6 bathroom(s). The listed interior size range is 5000 + sq. ft..
What lot, basement, garage, or parking details are listed?
The lot size is listed as approximately 85.55 x 142.88 Feet. The basement is listed as: Finished. Garage type: Attached. Total parking: 4 space(s).
What heating, cooling, and exterior details are shown?
Heating is listed as: Gas, Water. Cooling is listed as: Central Air. Exterior/construction materials are listed as: Brick.
Where is this property located?
82 Chestnut Park Road, Toronto, ON is located in the Rosedale-Moore Park neighbourhood of Central Toronto. The listed cross street is Roxborough/Mount Pleasant.
What information is available on this public listing page?
The public listing page shows current active listing information, property photos, room details when available, map location, listed price, property features, and contact options. Annual taxes are listed as $52,794 / 2025. Valuation tools and similar sold-property previews are available after sign-in where applicable, without displaying sold data in this public FAQ.

FAQ content is based on current active listing fields shown on this page. Sold prices, sold comparables, and VOW-only details are not included in this public FAQ.