82 Chestnut Park Road

Rosedale-Moore Park, Toronto, Ontario M4W 2R3

Overview

At a glance

Days on market147 days
ListedJun 2, 2026
UpdatedSep 9, 2026
Building age100+ years
Size5000 + sq ft
Lot85.55 x 142.88 Feet
Property taxes$52,794 (2025)
Parking4 spaces
BasementFinished
MLS® numberC13227720
Data sourcePropTx MLS® System
Listing brokerageCHESTNUT PARK REAL ESTATE LIMITED

About this home

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!

Details

Property

Style
3-Storey
Building age
100+
Fronting on
East
Cross street
Roxborough/Mount Pleasant
Community
Rosedale-Moore Park
Municipality
Toronto C09

Inside

Bedrooms above grade
4
Bedrooms below grade
1
Bathrooms
6
Kitchens
1
Basement
Finished
Family room
Yes
Fireplace
Yes
Interior features
Central Vacuum

Utilities

Heating
Water
Heating fuel
Gas
Cooling
Central Air
Sewer
Sewer

Building

Construction
Brick
Foundation
Unknown
Roof
Slate
Pool
Inground

Parking

Garage
Attached
Parking spaces
3
Total parking
4
Driveway
Private

Land

Frontage
85.55
Depth
142.88
Lot size units
Feet
Lot irregularities
West 56.37'
Waterfront
No
Property features
Public Transit, Park, Place Of Worship, School, Rec./Commun.Centre
Rooms (12)
RoomLevelSizeFeatures
FoyerMain2.31 x 1.7Hardwood Floor, Double Closet, Elevator
Living RoomMain5.18 x 4.88Fireplace, Bay Window, Hardwood Floor
Dining RoomMain5.31 x 4.88Hardwood Floor, Fireplace, Bay Window
Family RoomMain7.11 x 4.06Fireplace, Stone Floor, Walk-Out
KitchenMain5.79 x 3.48Eat-in Kitchen, Centre Island, B/I Appliances
BreakfastMain6.45 x 3.76Fireplace, French Doors, W/O To Terrace
Primary BedroomThird11.02 x 6.25Skylight, His and Hers Closets, 5 Pc Ensuite
Bedroom 2Second7.62 x 4.27Fireplace, Walk-In Closet(s), 5 Pc Ensuite
Bedroom 3Second4.11 x 3.58Hardwood Floor, Double Closet, 3 Pc Ensuite
Bedroom 4Second6.5 x 4.88Bay Window, Hardwood Floor, 4 Pc Bath
Bedroom 5Lower5.59 x 4.88Window, 3 Pc Bath
RecreationLower5.18 x 4.88Window
Value

What it’s worth

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Market read

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History

Listing history

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Compare

How it compares

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Neighbourhood

Around Rosedale-Moore Park

What’s nearby

Quiet streetBackyard faces north

  • Elementary schoolRosedale Junior Public Schoolabout 6 min walk
  • High schoolMsgr Fraser College - Isabella Campusabout 18 min walk
  • ParkDavid A. Balfour Parkabout 2 min walk
  • Playground about 4 min walk
  • TrailDavid Balfour Park Trailabout 4 min walk
  • River or lakeYellow Creekabout 4 min walk
  • Grocery storeHarvest Wagonabout 6 min walk
  • DowntownTorontoabout 2.9 km
  • LibraryToronto Public Library - Toronto Reference Libraryabout 12 min walk
  • Rec centre or arenaRosedale-Moore Park Community Associationabout 7 min walk
  • Golf courseDogleg Leftabout 3.3 km
  • HospitalSunnybrook Holland Centreabout 23 min walk
  • Highway on-ramp about 20 min walk
  • GO or train stationToronto Union Stationabout 3.9 km

Approximate: straight-line distances, and the backyard and street worked out from the map pin and map data © OpenStreetMap contributors. Check school boundaries with the school board.

On the map

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Community

The Rosedale-Moore Park market

Rosedale-Moore Park sale prices

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Costs

What it would cost

%
%
An example rate. Use the one your lender quotes.
Every monthEstimate
Mortgage payment$0
Property tax$0
Monthly total$0
At closing
Ontario land transfer tax$0

Estimates only, not financial advice. Uses Canadian semi-annual compounding, the minimum down payment and mortgage insurance rules, and Ontario’s land transfer tax brackets. Your lender and lawyer confirm the real numbers. Legal fees, title insurance and moving costs aren’t included.

Listing courtesy of CHESTNUT PARK REAL ESTATE LIMITED. Listing information from the PropTx MLS® System. Each listing shows the brokerage that represents it. The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate and may not be used for any commercial purpose or any other purpose. Information is deemed reliable but is not guaranteed accurate by PropTx. Last updated October 27, 2026 at 2:48 p.m.

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