82 Chestnut Park Road, Toronto, ON
Rosedale-Moore Park, Toronto · MLS® C13227720
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!
Key facts
- Property type
- Detached, 3-Storey
- MLS®
- C13227720
- Bedrooms
- 5 (4 + 1)
- 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
- 45
- 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
Heads up: the asking price here sits well above what comparable listings suggest. That can point to premium finishes, a bigger lot, or simply an ambitious ask, so it is worth a close look before you offer. I would not put an automatic figure on this one. 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.
Ask Moe if this price is fairIts public catchment (Rosedale Junior Public School) tests around the provincial average, a steady, family-friendly draw. The full EQAO breakdown is below.
On location, this is a very walkable address with everyday errands close by. Crescent Rd at South Dr is about a 2-minute walk away. Walkable, transit-friendly spots tend to hold value and widen your resale pool.
What the listing highlightsThese are claims from the listing. The only way to know for sure is to see it in person, and I am happy to book you a private showing.
- Ravine lot: privacy and premium value, but confirm the buildable area and any conservation limits.
- Pool: lifestyle appeal, but adds maintenance, insurance, and resale is mixed.
- Elevator: rare and valuable for accessibility and resale.
- Sold as-is / needs work: budget for renovation, the price should reflect the condition.
- Worth verifying
- Weigh carefully
- Lifestyle
The closest active listings by size, beds, and price, so you can see what this home is up against.
The 3 closest active listings nearby.
See all comparable homes44 days longer than the Toronto average (1 days).
View comparable listingsPrice per square foot vs the area average.
Neighbourhood & 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.
Getting around
Very WalkableA walkability read built from the amenities around this home: how close the nearest transit stop is, and how many grocery, dining, park, and pharmacy destinations fall within a 15-minute walk. It is a guide, not a guarantee. Places data from Google.
Most daily errands can be done on foot.
🚉 Nearest transit: Crescent Rd at South Dr, about 187 m away
Within a 15-minute (1.5 km) walk.
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.
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 3.99% via Ratehub.ca (as of July 17, 2026); conventional rates run a little higher.
Mortgage amount $10,000,000 · 4.14% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $53,364
- Property tax
- $4,400
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $57,763
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
- $3,201,823
- Principal paid down
- $1,273,502
- Interest paid
- $1,928,320
- Balance remaining
- $8,726,498
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 numbersEstimates only. Rent is modelled on above-grade size and local norms, so a finished basement or second suite (a separate entrance often means one) can push real rent well above this. Taxes, fees, and vacancy vary by property, and cap rate is before financing. A starting point, not a final number, let us run the real ones with you.
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.