82 Chestnut Park Road: A Rosedale-Moore Park Trophy Estate

Property Overview

Offered at $13,950,000, 82 Chestnut Park Road represents a rare opportunity to own a landmark residence in the heart of Rosedale-Moore Park, one of Toronto’s most prestigious and tightly held neighbourhoods. This elegant Georgian estate spans nearly 8,000 square feet and is positioned on an extraordinary 85-foot-wide tableland lot overlooking the Chestnut Park ravine.

Located just two blocks from Yonge Street yet surrounded by mature trees and parkland, the home delivers the perfect balance of privacy, luxury, and urban accessibility. This is refined Toronto living at its highest level.

Timeless Design & Luxury Interior Features

The residence showcases classic architectural grace paired with modern convenience. Every bedroom features its own ensuite bathroom, while a private elevator, full-home generator, and garage with lift ensure effortless daily living.

At the heart of the home is a truly sumptuous primary suite, complete with separate his-and-her dressing rooms and serene views over the ravine. Curated interiors throughout the home reflect understated luxury, designed for both elegant entertaining and comfortable family living.

Outdoor Living & Resort-Style Lifestyle

One of the most compelling features of this estate is its oversized inground pool, a virtually irreplaceable amenity in Rosedale. The landscaped grounds form a private garden oasis — an “endless summer” retreat rarely found in the city.

Multiple terraces, including an outdoor kitchen, create seamless indoor-outdoor living spaces ideal for dining, entertaining, and relaxing beneath the area’s iconic tree canopy.

The Prestige of Rosedale-Moore Park

Rosedale-Moore Park is synonymous with heritage, exclusivity, and lifestyle excellence. Residents enjoy immediate access to top private and public schools, subway transit, boutique shopping, tennis clubs, skating rinks, and scenic hiking and biking trails that extend all the way to Lake Ontario.

Just minutes away, Yorkville and Toronto’s downtown core offer world-class dining, luxury retail, and cultural destinations — all within a 10-minute drive.

Why 82 Chestnut Park Road Is Truly Rare

Opportunities to own a property of this scale, setting, and quality in Rosedale are exceedingly rare. With its ravine-top position, resort-style amenities, and timeless Georgian architecture, this estate stands apart as a true trophy property.

For discerning buyers seeking privacy, prestige, and long-term value in Toronto luxury real estate, 82 Chestnut Park Road is simply unmatched.

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