$12,500,000
82 Chestnut Park Road, Toronto C09, ON M4W 2R3
5 Beds
6 Baths
4 Parking
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 home features stunning multiple terraces for sitting, dining, and entertaining, complete with an outdoor kitchen. Inside, discover serene, curated interiors & an exceptionally sumptuous sky-lit primary suite with lush treetop views, a sitting area with fireplace, his & her separate dressing rooms and spa-inspired ensuite. This trophy property blends timeless grace, 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 exceptional flexibility. Set beneath a treed canopy for total privacy, you are just steps from the subway, top 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!

Property Summary

Property Type Residential Freehold
Property Sub Type Detached
Transaction Type For Sale
Style 3-Storey
Approximate Age 100+
Bedrooms Above Grade 4
Bedrooms Below Grade 1
Bathrooms 6
Basement Finished
Exposure East
Possession 60 days / TBD

Building

Building Type Detached
Square Footage 5000 +
Exterior Brick
Foundation Unknown
Roof Slate
Heating Water
Heat Source Gas
Cooling Central Air
Fireplace Yes

Measurements

Lot Size 85.55 x 142.88
Lot Size Units Feet
Frontage 85.55
Depth 142.88
Total Living Area 5000 +

Land

Address 82 Chestnut Park Road, Toronto C09, ON M4W 2R3
City Toronto C09
Community Rosedale-Moore Park
County / Area Toronto
Cross Street Roxborough/Mount Pleasant
Sewer Sewer
Pool Inground
Parcel Number 211190148

Parking and Garage

Total Parking 4
Garage Spaces 2
Garage Type Attached
Parking Features Private

Taxes and Listing Info

List Price $12,500,000
Annual Taxes $52,794
Tax Year 2025
Status Active
Listing Date 2026-06-02T14:42:26Z
MLS Number C13227720
Local Market Insight

What Buyers Should Know About 82 Chestnut Park Road, Toronto C09, ON M4W 2R3

This editorial summary helps buyers look beyond the headline price and review the neighbourhood, transit, schools, rental demand, long-term value, and due-diligence items that often matter before booking a showing or submitting an offer.

Neighbourhood Analysis

82 Chestnut Park Road, Toronto C09, ON M4W 2R3 is positioned in Rosedale-Moore Park, a part of Toronto C09 where buyers should compare the street setting, nearby amenities, daily travel routes, and surrounding housing stock. For a 3-Storey, the strongest fit often depends on whether the location supports everyday routine as well as the numbers on paper.

School And Family Considerations

Families reviewing this Detached should confirm school boundaries directly with the local school boards before relying on listing notes. It is also worth checking walkability to parks, childcare, recreation centres, libraries, and community facilities because these details can influence both lifestyle value and future resale demand.

Transit And Access

The location should be assessed around commute patterns, access to Roxborough/Mount Pleasant, public transit options, parking availability, and drive times to employment areas. A property with 4 parking and practical road access can appeal to buyers who need convenience without giving up neighbourhood quality.

Investment Potential

At $12,500,000, buyers should compare recent nearby sales, days on market, condition, lot utility, and the cost of future repairs or upgrades. The property shows 5 bedrooms, 6 bathrooms, basement details marked as Finished, and a lot size of 85.55 x 142.88, all of which can affect value.

Rental Demand

If this property is being reviewed as a rental or investment, demand should be measured by bedroom count, transit access, employment access, nearby schools, parking, and the condition of the unit or home. In Toronto C09, rental appeal usually improves when a property is easy to maintain and simple for tenants to live in.

Local Attractions And Amenities

Buyers should look at grocery access, restaurants, trails, parks, shopping, medical services, and weekend amenities around Rosedale-Moore Park. These features do not always appear in the MLS data, but they can make a major difference in how the home feels after move-in and how future buyers compare it.

Builder, Condition, And Due Diligence

For resale homes, review renovations, permits, roof and mechanical age, exterior condition, inclusions, and rental items. For condo or newer properties, review building history, maintenance fees, reserve fund information, rules, amenities, and future cost exposure. A showing and document review should confirm anything not visible in the listing.

Nearby Infrastructure

Infrastructure matters because transit improvements, road projects, schools, parks, commercial growth, and employment nodes can change how an area performs over time. For 82 Chestnut Park Road, Toronto C09, ON M4W 2R3, buyers should check municipal plans, nearby construction, zoning context, and future projects that may affect enjoyment or resale value.

This section is informational only. Buyers should verify schools, measurements, rental rules, taxes, zoning, and property condition with the appropriate professionals before making a decision.

Listing data is provided through PropTx/MLS data services and is deemed reliable but not guaranteed. Listings are subject to change without notice.