82 Chestnut Park Road, Toronto, ON
Rosedale-Moore Park, Toronto · MLS® C13227720
About this home
In short
- Extremely rare endless summer escape in a poolside paradise with 7-Star resort-style luxury.
- Embraced by mature trees and manicured lawns, this extraordinarily expansive 85-foot-wide tableland property sits atop the exclusive Chestnut Park ravine, overlooking...
- A true garden oasis, the stunning oversized pool is virtually irreplaceable in this area, creating an idyllic opportunity for captivating family living and...
- 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.
- Additional highlights include an ELEVATOR, generator, garage with lift & ensuite bathrooms in all bedrooms for superb flexibility.
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
- Property type
- Detached, 3-Storey
- MLS®
- C13227720
- Bedrooms
- 4+1 (5 total)
- Bathrooms
- 6 (1 half)
- Size
- 5,000 sq ft
- Lot
- 85.55 × 142.88 ft
- Cross streets
- Roxborough/Mount Pleasant
- Parking
- 2 garage · 4 parking (attached)
- Driveway
- Private
- Basement
- Finished
- Heating
- Water
- A/C
- Central Air
- Exterior
- Brick
- Foundation
- Unknown
- Roof
- Slate
- Sewer
- Sewer
- Pool
- Inground
- Property tax
- $52,794 / 2025
- Days on market
- 101
- Listing brokerage
- CHESTNUT PARK REAL ESTATE LIMITED
Rooms
window · 3 pc bath
fireplace · stone floor · walk-out
eat-in kitchen · centre island · b/i appliances
skylight · his and hers closets · 5 pc ensuite
Window
fireplace · french doors · w/o to terrace
fireplace · walk-in closet(s) · 5 pc ensuite
hardwood floor · fireplace · bay window
hardwood floor · double closet · 3 pc ensuite
hardwood floor · double closet · elevator
bay window · hardwood floor · 4 pc bath
fireplace · bay window · hardwood floor
Listed at $12,500,000. My estimate lands at $5.39M, so the ask sits about 132% above what comparable sales suggest. A gap that wide can point to premium finishes, a bigger lot, or simply an ambitious ask, so it is worth a close look at what justifies it before you offer. Treat the figure as a starting point: tell me you are interested and I will pull the most comparable recent sales and give you a straight answer on what it will really take.
A price cut is the likelier next move. 101 days on the market against about 38 for homes like it here, and asking 132% above where comparable closings put it. That is leverage for a buyer: offer with it in mind rather than waiting for the cut, since a reduction brings new eyes with it.
Second read, from the city assessment: $12.10M. That is about 125% above the comparable-sales figure. When my two methods disagree this much, the answer usually sits between them and something about this home is not in the comparables (the lot, the condition, a rebuild). I would want to see it before leaning on either number.
Total price vs nearby homes. Fair value about $5.39M, median of 45 comparables.
The market behind the math:
About 1.3 months of inventory: 8 detached homes for sale in the area against 18 closings in the last 90 days. Under two months favours sellers, over four favours buyers.
Price per square foot: this home lists at $2,500/sqft against an area asking average of $1,616/sqft. Size and $/sqft both feed the estimate above.
- Ravine / green setting. This home is described as backing onto a ravine or green setting. A premium that comparable-sales math under-prices, so read the estimate as a floor.
- Inground pool. Priced into the comparison on the assumption it is clean and modern. A pool costs more to build than resale pays back, and condition is the in-person call.
How this estimate is builtthe short version
I take the 45 most comparable recent sales nearby and adjust each one to this home for the real differences (size, beds, baths, garage, lot frontage, a ravine backing, an inground pool), then use the median, which is steadier than leaning on any single sale.
It’s grounded in recent closing prices, not asking prices. Lot, condition, and finishes are my in-person call, and the city (MPAC) assessment points to about $12.10M, higher than the comparables and worth a second look.
What the listing highlights4 points to weigh
Claims from the listing, worth confirming in person. I can book you a private showing.
- Ravine lot: privacy and premium value, but confirm the buildable area and any conservation limits. Worth verifying
- Pool: lifestyle appeal, but adds maintenance, insurance, and resale is mixed. Weigh carefully
- Elevator: rare and valuable for accessibility and resale. Lifestyle
- Sold as-is / needs work: budget for renovation, the price should reflect the condition. Weigh carefully
Schools & getting aroundcatchment and transit
Its public catchment (Rosedale Junior Public School) tests around the provincial average, a steady, family-friendly draw. The full EQAO breakdown is below.
Read this with carewhy it’s an estimate, not an appraisal
There were not many closely comparable homes right in Rosedale-Moore Park, so I widened the search to the surrounding area.
Based on 45 comparable homes that sold in Rosedale-Moore Park over the past two years, from 151 closings there.
Nothing closely matching this home is listed nearby right now, so these are the nearest detached listings on the market. Homes like this one have recently closed around $5.39M, which is where my estimate comes from.
Per square foot, these ask about $1,611/sqft; this home lists at $2,500/sqft. Size is part of the price story, not just the sticker.
The 3 closest active listings nearby.
See all comparable homesNeighbourhood & location
Rosedale-Moore Park, Toronto, ON
Enter a workplace or destination and we’ll show the door-to-door time by car, transit and bike.
How asking prices compare in the closest areas to this home. Longer bars mean a pricier market.
Typical asking price of active listings of the same type, per area (outliers removed). Toronto.
Get the full neighbourhood report (schools, parks, transit & safety) →
The public and Catholic schools this address is zoned for, with EQAO results (the share of students meeting Ontario's provincial standard).
School attendance boundaries and EQAO results are Ontario government data and can change. Confirm the current catchment with the school board before relying on it.
Also nearby: 12 more schools within 2.5 km
Not the assigned catchment: schools a family here could reach, with EQAO results where published.
Affordability & Mortgage
Income needed assumes a ~32% GDS ratio; weekly is mortgage principal & interest only. Price ÷ income is the home price over the income needed. Fixed reference assumptions so listings compare on equal footing, not a lending decision.
Calculate and customize your mortgage and other expenses
Adjust the down payment, rate, and amortization, and add property tax, condo fees, and heating to see your true monthly cost.
Your numbers
Homes over $1.5M can't be insured, so 20% down or more is required.
Conventional (20%+ down). Best insured 5-year fixed 4.09% via Ratehub.ca (as of September 11, 2026); conventional rates run a little higher.
Mortgage amount $10,000,000 · 4.24% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $53,911
- Property tax
- $4,400
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $58,311
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $298,975
- Toronto municipal land transfer tax
- $578,975
- Estimated closing costs
- $877,950
Plus your down payment of $2,500,000. Legal fees, title insurance, and adjustments are extra and vary by deal.
Mortgage stress test
Lenders qualify you at the greater of your rate plus 2% or 5.25%. You do not pay this rate. It just shows you could still handle payments if rates rose, so aim to stay comfortable at this higher number.
Over the full 25 years
At the end of your 5-year term
- Total paid over the term
- $3,234,667
- Principal paid down
- $1,258,578
- Interest paid
- $1,976,090
- Balance remaining
- $8,741,422
Talk to Team Asgarian about your options
Rates and programs change often. We will connect you with a trusted mortgage professional and build a plan that fits your budget and goals.
Estimates only, not a mortgage quote or pre-approval. Figures use Canadian semi-annual compounding, current minimum down-payment rules, CMHC premium tiers, and Ontario (plus Toronto, when selected) land transfer tax. Actual rates, taxes, insurance, and closing costs vary by lender and property. Confirm every number with your mortgage professional.
Investor snapshot
Thinking of this home as an investment? We will pull real comparable rents and run the full numbers with you.
Talk about the numbersThe last 16 whole-home leases in Rosedale-Moore Park signed at a median of $15,775 a month; adjusted to this home for size, beds and baths, and for where rents stood the month each signed, that is $17,320. The gross yield above is on the asking price, before taxes and upkeep; the cap rate is after them. A finished basement or second suite can push real rent above it. Taxes, fees, and vacancy vary by property, and cap rate is before financing.
Helpful resources
All information deemed reliable but not guaranteed. For personal, non-commercial use only. Listing courtesy of CHESTNUT PARK REAL ESTATE LIMITED. MLS®/PropTx.