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!
About this home
Photos of 82 Chestnut Park Road
Facts and features of 82 Chestnut Park Road
| Type | Detached |
|---|---|
| Style | 3-Storey |
| Bedrooms | 4 + 1 |
| Bathrooms | 6 |
| Size | 5000 + sq ft |
| Lot | 85.55 x 142.88 Feet |
| Parking | 4 |
| Garage | Attached |
| Heating | Water |
| Cooling | Central Air |
| Basement | Finished |
| Exterior | Brick |
| Age | 100+ |
| Taxes | $52,794 (2025) |
| Days on market | 149 |
| Listing brokerage | CHESTNUT PARK REAL ESTATE LIMITED |
Rooms
12 rooms, with sizes
| Room | Level | Size | Features |
|---|---|---|---|
| Bedroom 5 | Lower | 18′ 4″ × 16′ 0″ 5.59 × 4.88 m | window, 3 pc bath |
| Family Room | Main | 23′ 4″ × 13′ 4″ 7.11 × 4.06 m | fireplace, stone floor, walk-out |
| Kitchen | Main | 19′ 0″ × 11′ 5″ 5.79 × 3.48 m | eat-in kitchen, centre island, b/i appliances |
| Primary Bedroom | Third | 36′ 2″ × 20′ 6″ 11.02 × 6.25 m | skylight, his and hers closets, 5 pc ensuite |
| Recreation | Lower | 17′ 0″ × 16′ 0″ 5.18 × 4.88 m | Window |
| Breakfast | Main | 21′ 2″ × 12′ 4″ 6.45 × 3.76 m | fireplace, french doors, w/o to terrace |
| Bedroom 2 | Second | 25′ 0″ × 14′ 0″ 7.62 × 4.27 m | fireplace, walk-in closet(s), 5 pc ensuite |
| Dining Room | Main | 17′ 5″ × 16′ 0″ 5.31 × 4.88 m | hardwood floor, fireplace, bay window |
| Bedroom 3 | Second | 13′ 6″ × 11′ 9″ 4.11 × 3.58 m | hardwood floor, double closet, 3 pc ensuite |
| Foyer | Main | 7′ 7″ × 5′ 7″ 2.31 × 1.7 m | hardwood floor, double closet, elevator |
| Bedroom 4 | Second | 21′ 4″ × 16′ 0″ 6.5 × 4.88 m | bay window, hardwood floor, 4 pc bath |
| Living Room | Main | 17′ 0″ × 16′ 0″ 5.18 × 4.88 m | fireplace, bay window, hardwood floor |
Around this home
What’s near 82 Chestnut Park Road
From 82 Chestnut Park Road, the nearest station is Rosedale station (Line 1 Yonge-University), about 600 m away; the nearest grocery store is Harvest Wagon, about 600 m away; the nearest TDSB elementary school is Rosedale Junior Public School, about 300 m away; and the nearest park is Roxborough Parkette, about 150 m away.
Transit
- Rosedale station Line 1 Yonge-University about 600 m
- Summerhill station Line 1 Yonge-University about 600 m
- Sherbourne station Line 2 Bloor-Danforth about 1.0 km
Groceries and pharmacies
- Shoppers Drug Mart Pharmacy about 550 m
- Harvest Wagon Grocery about 600 m
- Marshall's Drugs Pharmacy about 850 m
- Rabba Grocery about 900 m
- Summerhill Market Grocery about 950 m
Parks
- Roxborough Parkette Park about 150 m
- Alex Murray Parkette Park about 200 m
- Pricefield Road Playground Park about 450 m
Schools
- Rosedale Junior Public School TDSB elementary · JK-6 EQAO 2024-25: Gr 6 reading 100% · Gr 6 math 100% about 300 m
- Whitney Junior Public School TDSB elementary · JK-6 EQAO 2024-25: Gr 6 reading 100% · Gr 6 math 88% about 900 m
- Spectrum Alternative Senior School TDSB middle school · 7-8 about 2.3 km
- Our Lady of Perpetual Help Catholic School Catholic elementary · JK-8 EQAO 2024-25: Gr 6 reading 100% · Gr 6 math 80% about 750 m
- Rosedale Heights School of the Arts TDSB secondary · 9-12 EQAO 2024-25: Gr 9 math 66% · Gr 10 literacy 95% about 1.6 km
- Msgr Fraser College (Isabella Campus) Catholic secondary · 9-12 about 1.3 km
Nearest schools, not necessarily the ones that serve this address. Check with the TDSB and TCDSB school locators.
Community
- Rosedale-Moore Park Community Association Community centre about 300 m
- Toronto Reference Library Library Library about 950 m
- Aquatic Centre Pool or arena about 1.5 km
Private schools
- Girls
- Branksome Hall JK to Grade 12 about 650 m
- The Bishop Strachan School JK to Grade 12 about 2.4 km
- Boys
- Upper Canada College JK to Grade 12 about 2.0 km
- Royal St. George's College Grades 3 to 12 about 2.5 km
- St. Michael's College School Grades 7 to 12 about 2.8 km
- Co-ed
- De La Salle College "Oaklands" Grades 5 to 12 about 1.2 km
- The Rosedale Day School JK to Grade 8 about 1.5 km
- The York School JK to Grade 12 about 1.6 km
- The Mabin School JK to Grade 6 about 1.6 km
Within a 40-minute walk, from our list of private schools in central Toronto (checked October 2026). Fees and admissions on each school’s site. See all private schools
Restaurants
- Mineral Google reviews about 550 m
- Terroni Google reviews about 550 m
- Bar Centrale Google reviews about 600 m
- Avant Goût Google reviews about 600 m
- Quanto Basta Google reviews about 600 m
Places: OpenStreetMap contributors, October 2026. Straight-line distances. Schools: EQAO 2024-25, Ontario Ministry of Education.
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Rosedale
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82 Chestnut Park Road
Listing information is deemed reliable but is not guaranteed accurate by PropTx or the Toronto Regional Real Estate Board. Data source: PropTx. Listings are refreshed from the MLS® at least daily.
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.
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MLS® C13227720 Data source: PropTx Listed June 2, 2026
