82 Chestnut Park Rd
Rosedale-Moore Park, Toronto, Ontario M4W 2R3
- Bedrooms
- 4+1
- Bathrooms
- 6
- Size
- 5,000 +sq ft
- Lot
- 85.55 x 142.88 ft
- Tax a year
- $52,7942025 tax year
- Built
- 100+
- Parking
- 42 attached
- Days on market
- Members
The brief
About 82 Chestnut Park Rd
82 Chestnut Park Rd is a 4+1-bedroom, 6-bathroom detached house in Rosedale-Moore Park, Toronto, listed for sale at an asking price of $12,500,000 (MLS® C13227720).
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!
Insights
Condition Score
Good68/1006 condition-related facts documented
Source: Listing age, structured features and disclosed update language; not an inspection.
Cashflow Quality
Shortfall5/100−$51,477/mo against the cost of owning (20% down, 4.8%, 25 yrs)
Source: Median of 5 homes with 5 bedrooms for lease in Rosedale-Moore Park right now. Cost of owning counts the mortgage and property tax.
Condition uses listing-record signals, not an inspection.
The home
Key facts
- Tax
- $52,794 / 2025
- MLS® number
- C13227720
- Board
- TRREB MLS®
- Property Type
- Detached
- Building Age
- 100+
- Days on market
- Size
- 5000 + sqft
- Lot Size
- 85.55 x 142.88 ft
- Listed on
- Parking
- 2 Attached, 4 Parking
Property details
Property
- Property Type
- Detached
- Style
- 3-Storey
- Community
- Rosedale-Moore Park
- Municipality
- Toronto
Building
- Size
- 5000 + sqft
- Building Age
- 100+
- Construction
- Brick
Inside
- Bedrooms
- 4+1
- Bathrooms
- 6
- Bathroom Details
- 2 × 5pc, 1 × 4pc, 2 × 3pc, 1 × 2pc
- Basement Type
- Finished
- Kitchens
- 1
Parking
- Driveway
- Private
- Garage Type
- Attached
- Garage
- 2
- Additional Parking
- 2
- Total Parking
- 4
Utilities
- Water
- Municipal
- Cooling
- Central Air
- Heating Type
- Water
Land
- Sewer
- Sewers
- Frontage
- 85.55 ft
- Depth
- 142.88 ft
- Lot Size
- 85.55 x 142.88 ft
Additional
- Roof
- Slate
- Fireplace
- Yes
- Pool
- Inground
- Den
- Yes
- Family room
- Yes
Rooms
| Room | Size | Features | Level |
|---|---|---|---|
| Foyer | 1.7 × 2.31 m | hardwood floor, Double Closet, Elevator | Main |
| Living | 4.88 × 5.18 m | Fireplace, Bay Window, hardwood floor | Main |
| Dining | 4.88 × 5.31 m | hardwood floor, Fireplace, Bay Window | Main |
| Family | 4.06 × 7.11 m | Fireplace, Stone Floor, Walk-Out | Main |
| Kitchen | 3.48 × 5.79 m | Eat-In Kitchen, Centre Island, B/I Appliances | Main |
| Breakfast | 3.76 × 6.45 m | Fireplace, French Doors, W/O To Terrace | Main |
| Primary | 6.25 × 11.02 m | Skylight, His/Hers Closets, 5 Pc Ensuite | 3rd |
| 2nd Br | 4.27 × 7.62 m | Fireplace, W/I Closet, 5 Pc Ensuite | 2nd |
| 3rd Br | 3.58 × 4.11 m | hardwood floor, Double Closet, 3 Pc Ensuite | 2nd |
| 4th Br | 4.88 × 6.5 m | Bay Window, hardwood floor, 4 Pc Bath | 2nd |
| 5th Br | 4.88 × 5.59 m | Window, 3 Pc Bath | Lower |
| Rec | 4.88 × 5.18 m | Window | Lower |
Listing history
Buy/sell history for 82 Chestnut Park Rd, Toronto, Ontario
Sale history on this site covers the last 2 years, the window permitted under the TRREB MLS® VOW agreement.
| Date Start | Date End | List Price | Price | Event | Listing ID |
|---|---|---|---|---|---|
| Date StartN/A | N/A | $12,500,000 | N/A | For Sale | C13227720 |
Members see the full history. Prices are hidden from signed-out visitors.
The numbers
Mortgage Calculator
Plan with the current asking price
CMHC insurance: not required at 20% down. Payments use Canadian semi-annual compounding.
Mortgage Details
4.8% · 5-year term · 25-year amortization · 20% down
- Total down payment
- $2,500,000
- Total mortgage amount
- $10,000,000
- Total interest payment
- $7,108,400
- Total purchase cost
- $19,608,400
- Mortgage payment
- $57,028/mo
Cash Flow Analysis
If you rented this home out at 20% down
Break-even down payment
92%Monthly carrying cost
$61,427- Rent $9,950
- Shortfall $51,477
Rental income opens at $9,950, the median asking rent of 5 comparable homes for lease in Rosedale-Moore Park. Type over it with the rent you expect. This is a planning tool, not advice.
Land transfer tax on this home
- Ontario land transfer tax
- $298,975
- Toronto municipal land transfer tax
- $578,975
- Total land transfer tax
- $877,950
- First-time buyer rebates (Ontario up to $4,000 + Toronto up to $4,475)
- −$8,475
- Total for first-time buyers
- $869,475
See how this is worked out
- 0.5% on the first $55,000
- $275
- 1.0% from $55,000 to $250,000
- $1,950
- 1.5% from $250,000 to $400,000
- $2,250
- 2.0% from $400,000 to $2,000,000
- $32,000
- 2.5% from $2,000,000 to $12,500,000
- $262,500
- Ontario total
- $298,975
Toronto’s municipal tax has its own higher brackets at this price, so it adds $578,975.
An estimate at the asking price, for a home with one or two single-family residences. Your lawyer confirms the exact amount.
Estimate
Estimated value requires sign in
Market estimates use sold comparables and are available after you sign in and accept MLS® VOW terms.
The estimate is an automated value built from public and MLS® data. It is not an appraisal; ask Kassaundra Dobson, Broker of Record for a full comparative market analysis.
Comparable sales
Comparable sales require sign in
Closing prices and sold comps are available to registered visitors who accept MLS® VOW terms on this site.
The land
Lot
- Street frontage
- 85.55 ft26.1 m
- Depth
- 142.88 ft43.5 m
The record marks this lot irregular, so its area is not the frontage multiplied by the depth. It is not given here. Confirm with a survey before you buy.
Source: the MLS® listing record.
Land and environment
Public records about this location. Not part of the MLS® listing and not provided by the listing brokerage.
Water and conservation3
- Not in Toronto and Region Conservation Authority’s mapped regulated areaAt the address
- No mapped wetland within 120 m120 m
- No water-supply well recorded within 250 m4 test or monitoring holes also recorded.250 m
Toronto and Region Conservation Authority · Province of Ontario open data
Planning and building activity4
- Outside the Greenbelt, Oak Ridges Moraine and Niagara Escarpment plan areasAt the address
- 30 building permits issued within 250 m in the last 2 years250 m
- Nearest airport: 5.1 km5.1 km
- Mapped parcel: about 9,670 sq ftMeasured from the municipal parcel map, which can differ from the survey and from the lot size in the listing.At the address
Province of Ontario open data · Municipal building permits · toronto.parcels
Around the home2
- Nearest rail line: 430 m430 m
- A trail on the Ontario trail network within 1 km1 km
Province of Ontario open data
Environmental records4
- No licensed pit or quarry within 2 km2 km
- No recorded oil, gas or salt well within 250 m250 m
- No facility within 1 km reports pollutant releases to Environment CanadaThe nearest is The Governing Council of the University of Toronto — St George Campus, 2.4 km away. Only facilities above the inventory’s reporting thresholds are listed.1 km
- No federal contaminated site within 1 kmThe federal inventory covers federal land only; it says nothing about provincial or private sites.1 km
Province of Ontario open data · Government of Canada open data
Power and internet3
- Electricity is distributed here by Toronto Hydro-Electric System LimitedAt the address
- Wired internet 50/10 Mbps or faster is listed at this locationFixed wireless 50/10 Mbps or faster. LTE mobile coverage listed. ISED’s National Broadband Data at the nearest household point (20 m from the listing); 50/10 Mbps is its top category and includes faster plans. Confirm with a provider for this address.At the address
- Across the surrounding area: fibre to the home, cable, DSL internet listedFibre to the home: Beanfield Metroconnect, Bell, Dotto One, FibreStream, Rogers. Cable: Rogers. DSL: Bell. Fixed wireless: Bell, Rogers, Routcom, SkyChoice Communications. Mobile: Bell, Freedom Mobile, Rogers, Telus. Satellite: Xplore. ISED’s list for the surrounding ~25 km² area; check with a provider for this address.Area-wide
Ontario Energy Board · Innovation, Science and Economic Development Canada
Each record is placed at the distance its own line states. None of it is an inspection of the property. Confirm anything that matters to you with the municipality, Toronto and Region Conservation Authorityor the record’s publisher.
Contains information licensed under the Open Government Licence – Canada. Contains information licensed under the Open Government Licence – Ontario. Contains information licensed under the Open Government Licence – Toronto. Contains information made available under the Toronto and Region Conservation Authority Open Data Licence v1.0.
Heritage and ravine protection
- Not found on the Heritage Register
- In the Rosedale South Heritage Conservation District, by-law 115-2003
- Not in the mapped ravine protection area
What this means: Changes outside the house, and tree removal, may need the City’s review on top of the usual permits. Ask the City before you plan work.
City of Toronto Heritage Register, Heritage Conservation Districts and the Ravine and Natural Feature Protection by-law, read at this address from the City’s maps. Contains information licensed under the Open Government Licence – Toronto.
Zoning
Zone
RD (f15.0; d0.6) (x1435)By-law
569-2013Municipality
Toronto1 f15.0
Frontage: at least 15.0 m.
2 d0.6
Density: floor area is capped at 0.6 times the lot area.
3 x1435
Site-specific exception 1435: this site has rules of its own, written in the by-law.
4 Where this is written
Chapter 10, section 10.20 of By-law 569-2013 · Exception 900.3.10(1435)
5 What that means in practice
These are the zone’s rules, not permission for this lot. What can be built also depends on the exceptions, overlays and setbacks that apply here. Confirm with the City before you plan.
City of Toronto Zoning By-law 569-2013, read at this address from the City’s zoning map. Open the City’s zoning map. Contains information licensed under the Open Government Licence – Toronto.
Permit history
No building permits on file at this address.
Signals around this home
Changing nearby. 6 open development applications within 800 m of this home.
9 PRICE STSite planUnder Review
Site Plan Approval for a 19-storey mixed-use building having a non-residential gross floor area of 1569 square metres, and a residential gross floor area of 10,189 square metres. 143 residential dwelling units are proposed.
540 m away9 PRICE STOfficial plan or zoning amendmentUnder Review
Official Plan and Zoning By-law Amendment application to permit a 35-storey mixed-use building, containing 235 dwelling units and 1,645 square metres of non-residential gross floor area.
540 m away1087 YONGE STOfficial plan or zoning amendmentUnder Review
Official Plan and Zoning By-law Amendment application to permit a 35-storey mixed-use building, containing 235 dwelling units and 1,645 square metres of non-residential gross floor area.
560 m away1087 YONGE STSite planUnder Review
Site Plan Approval for a 19-storey mixed-use building having a non-residential gross floor area of 1569 square metres, and a residential gross floor area of 10,189 square metres. 143 residential dwelling units are proposed.
560 m away1091 YONGE STSite planUnder Review
Site Plan Approval for a 19-storey mixed-use building having a non-residential gross floor area of 1569 square metres, and a residential gross floor area of 10,189 square metres. 143 residential dwelling units are proposed.
570 m away1091 YONGE STOfficial plan or zoning amendmentUnder Review
Official Plan and Zoning By-law Amendment application to permit a 35-storey mixed-use building, containing 235 dwelling units and 1,645 square metres of non-residential gross floor area.
570 m away
City of Toronto Open Data — Development Applications and Building Permits (cleared permits since 2017). An application is a proposal: it may change, be refused or never be built. Contains information licensed under the Open Government Licence – Toronto.
The market
Detached homes for sale in Rosedale-Moore Park right now
- For sale now
- 44
- Median asking price
- $5.07M
- New in 7 days
- 9
- Price cuts
- 7%
Middle half: $2.94M to $7.6M
15 in 28 days
3 listings
This home is asking 146% above the median, higher than three quarters of them.
See all homes in Rosedale-Moore ParkAsking prices and counts of the MLS® listings on this site as of today. Asking figures only, never sold or leased prices.
Market area · filters apply to the charts below
The street
Map and tour
Transit nearby
| Station | Lines | Distance |
|---|---|---|
| Rosedale Station | TTC subway: Line 1 Yonge-University | 550 m |
| Summerhill Station | TTC subway: Line 1 Yonge-University | 700 m |
| Bloor-Yonge Station | TTC subway: Line 1 Yonge-University, Line 2 Bloor-Danforth | 1 km |
| Eglinton Station | TTC subway: Line 1 Yonge-UniversityTTC light rail: Line 5 Eglinton | 3 km |
| Union Station | TTC subway: Line 1 Yonge-UniversityGO Transit train: Barrie, Kitchener, Lakeshore East, Lakeshore West, Milton, Richmond Hill, StouffvilleUP Express train | 3.9 km |
The nearest subway, light rail, train, bus rapid transit stations 5 km, as the crow flies. Source: TTC schedule data (GTFS) from the Toronto Transit Commission under the Open Government Licence – Toronto; GO Transit and UP Express schedule data (GTFS) from Metrolinx under the Open Government Licence – Ontario – Metrolinx, downloaded October 18, 2026. Contains information licensed under the Open Government Licence – Toronto. Data used in this product or service is provided with the permission of Metrolinx. Metrolinx makes no representations or warranties of any kind, express or implied, with respect to the Data and assumes no responsibility for the accuracy or currency of the data used in this product or service. Contains information licensed under the Open Government Licence – Ontario – Metrolinx.
Schools nearby
| Elementary | Type | Distance | EQAO average 2024–25 |
|---|---|---|---|
| Rosedale Junior Public SchoolToronto DSB | Public · grades JK–6 | 300 m | 100%Grade 6 average |
| Our Lady of Perpetual Help Catholic SchoolToronto CDSB | Catholic · grades JK–8 | 750 m | 92%Grade 6 average |
| Whitney Junior Public SchoolToronto DSB | Public · grades JK–6 | 900 m | 96%Grade 6 average |
| École élémentaire Gabrielle-RoyConseil scolaire Viamonde | French-language public · grades JK–6 | 2.8 km | 96%Grade 6 average |
| Secondary | Type | Distance | Grade 9 math 2024–25 |
|---|---|---|---|
| Msgr Fraser College (Isabella Campus)Toronto CDSB | Catholic · grades 9–12 | 1.3 km | — |
| Rosedale Heights School of the ArtsToronto DSB | Public · grades 9–12 | 1.6 km | 66%Grade 9 math |
| Jarvis Collegiate InstituteToronto DSB | Public · grades 9–12 | 1.7 km | 34%Grade 9 math |
| Collège français secondaireConseil scolaire Viamonde | French-language public · grades 9–12 | 2 km | 86%Grade 9 math |
EQAO: share of students at or above the provincial standard, 2024–25 (Ontario open data). These are the schools nearest this home, not the schools it is assigned to: boundaries change, and some schools take students by application. Confirm with the board before you buy. Contains information licensed under the Open Government Licence – Ontario.
The verdict
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Recently sold nearby
Sold prices in Rosedale-Moore Park are shown to signed-in members.