Listed for:Listed Jun 1, 2026
$12,500,000

82 Chestnut Park Road

Toronto (Rosedale-Moore Park), ON M4W 2R3

Detached House For Sale
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Sale & Price History for 82 Chestnut Park Road, Toronto, Rosedale-Moore Park

No listing history available

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*Sold prices and complete sale & price history are regulated data. Under the Trust in Real Estate Services Act, 2002 (TRESA) and the rules of the Real Estate Council of Ontario (RECO), and pursuant to the Multiple Listing Service® rules of the Canadian Real Estate Association (CREA) and the Toronto Regional Real Estate Board (TRREB), this information may be shown only to registered users who have agreed to the applicable terms of use (a Virtual Office Website, or "VOW," arrangement). HOMEH Inc., Brokerage therefore provides it to signed-in members only. Creating an account is free and takes under a minute.

About 82 Chestnut Park Road, Toronto, Rosedale-Moore Park

Summarized Description

  • Rare poolside paradise with 7-Star luxury.
  • Oversized pool ideal for family living.
  • Elegant Georgian residence with 8,000 sq ft.
  • Multiple terraces for entertaining and dining.
  • Private country estate in prestigious Rosedale.
  • Elevator and garage with lift for convenience.
  • Steps from subway and top schools.
  • Exceptional flexibility with ensuite bathrooms.

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 & Features

Property Costs

Annual Property Tax Amount
$52,794
Land Transfer Tax Fee
$692,950

Basement Type
Finished

Interior Features

Interior Extras
Central Vacuum
Fireplace/Stove
Yes
Elevator
Yes

Exterior Features

Pool
Inground
Property Features
Public Transit, Park, Place Of Worship, School, Rec./Commun.Centre

Building

Building Type
Detached
Building Style
3-Storey
Approx Age
100+

Construction

Exterior Finish
Brick
Roof
Slate
Foundation Details
Unknown
Special Designation
Unknown

Lot

Lot Front
85.55 ft
Lot Depth
142.88 ft

Parking & Garages

Garage Type
Attached
Garage Spaces
2
Parking Spaces
3
Total Garage And Parking Spaces
4

Heating & Cooling

Heat Source
Gas
Heat Type
Water
Air Conditioning
Central Air
Water
Municipal
Sewers
Sewer

Bedrooms
4 + 1
Washrooms
6
Kitchens
1
Family / bonus room
Yes

Room sizes

  • Foyer—
    Main level, Hardwood Floor, Double Closet, Elevator
  • Living Room—
    Main level, Fireplace, Bay Window, Hardwood Floor
  • Dining Room—
    Main level, Hardwood Floor, Fireplace, Bay Window
  • Family Room—
    Main level, Fireplace, Stone Floor, Walk-Out
  • Kitchen—
    Main level, Eat-in Kitchen, Centre Island, B/I Appliances
  • Breakfast—
    Main level, Fireplace, French Doors, W/O To Terrace
  • Primary Bedroom—
    Third level, Skylight, His and Hers Closets, 5 Pc Ensuite
  • Bedroom 2—
    Second level, Fireplace, Walk-In Closet(s), 5 Pc Ensuite
  • Bedroom 3—
    Second level, Hardwood Floor, Double Closet, 3 Pc Ensuite
  • Bedroom 4—
    Second level, Bay Window, Hardwood Floor, 4 Pc Bath
  • Bedroom 5—
    Lower level, Window, 3 Pc Bath
  • Recreation—
    Lower level, Window

Washrooms

  • 5-piece
  • 4-piece
  • 3-piece
  • 2-piece

Municipality
Toronto
Neighbourhood
Rosedale-Moore Park
Main cross streets
Roxborough/Mount Pleasant
Directions
North on Chestnut Park from Roxborough Street East

MLS® number
C13227720
Data source
Toronto Regional Real Estate Board
Listed on
2026-06-01
Updated on
2026-09-09
Days on market
141 days
Possession type
60-89 days
Co-op commission
2.5% + HST
Seller
Listed by
CHESTNUT PARK REAL ESTATE LIMITED

Home Market Value

Current home valuation for 82 Chestnut Park Road, Toronto, Rosedale-Moore Park, Toronto, ON. Listed for $12,500,000

HOMEH Estimate

?

$10,541,713

Estimated Sales Range

?

$6,325,028 - $14,758,398

HOMEH Estimate for 82 Chestnut Park Road, Toronto, Rosedale-Moore Park

Calculated with a real agent's CMA method — 45+ years of experience, codified. Not an AI guess.

$10,541,713Low confidence
Based on 3 comparable properties
+ $1,958,287 (19%) above our estimate
See the full analysisFree Every recent nearby sale behind this number

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Mortgage Payment Calculator

Compare up to 4 down payment scenarios

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Toronto, ON
Minimum Down Payment Required:20.0%

20% required for homes $1.5M or more

Minimum down payment

$2,500,000

Scenario 1 Scenario 2 Scenario 3 Scenario 4
−Down payment
%
$
%
$
%
$
%
$
+CMHC insurance
$0$0$0$0
=Total mortgage
$10,000,000$9,375,000$8,750,000$8,125,000
Amortization
Mortgage rate
%
%
%
%
Payment frequency
=Mortgage payment
$48,825monthly$45,773monthly$42,722monthly$39,670monthly
Are you a first time home buyer?

Land Transfer Tax

Provincial

$298,975

Municipal (Toronto)

$393,975

Total Land Transfer Tax

$692,950

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0/100Minimal Transit
0/100Not rated
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