For Sale | $2,295,000

95 Highbourne Road

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Property Description

Offered for the first time in 47 years, 95 Highbourne Road presents a truly rare opportunity in the heart of Chaplin Estates. Situated on one of the neighbourhood’s most desirable, quiet, tree-lined streets, this classic detached home sits among beautifully maintained residences on larger lots in a setting defined by low traffic and midtown Toronto charm. 

Set on a 40 x 130 ft lot, the home showcases its original character through spacious principal rooms and timeless architectural details. The living room, centred around a wood-burning fireplace, is enhanced by a large bay window that fills the space with natural light and flows seamlessly into the dining room, ideal for both everyday living and entertaining.

At the rear, the kitchen and adjoining sitting room open directly to a quiet and private garden, creating a natural extension of the living space and a tranquil backdrop for outdoor living. A main floor powder room adds convenience. Upstairs, four well-sized bedrooms and a full family bathroom provide comfortable accommodation for growing families.

Perfectly positioned just moments from Yonge & Eglinton, this location offers exceptional access to the subway and the new Eglinton LRT, along with an array of neighbourhood shops, cafés, and restaurants (Little Sister and Oretta!). Steps to Oriole Park  Kay Gardner Beltline Trail along with access to some of Toronto’s most respected schools (UCC, BSS, Oriole Park JPS, Hodgson MS and North Toronto CI) further enhance the appeal.

Whether reimagined, renovated or rebuilt, this is a remarkable opportunity to create a lasting home in one of midtown Toronto’s most established and coveted communities.

A warm and inviting principal space, the living room is anchored by a classic wood-burning fireplace and framed by a large bay window that fills the room with natural light—perfect for both quiet evenings and relaxed entertaining.

Flowing seamlessly from the living room, the dining area offers an elegant setting for hosting, with generous proportions that easily accommodate both intimate dinners and larger gatherings.

Positioned at the rear of the home, the kitchen and adjoining sitting area overlook the garden, creating a bright, connected space with effortless indoor-outdoor flow—ideal for everyday living.

A private and peaceful outdoor retreat, the garden offers a tranquil setting surrounded by mature greenery—an ideal backdrop for summer dining, lounging, and entertaining.

A spacious and serene retreat, the primary bedroom offers ample room to unwind, with large windows that invite in soft natural light.

Three well-proportioned bedrooms provide flexibility for growing families, guest accommodations, or a dedicated home office—each offering comfort and versatility.

Thoughtfully positioned for everyday convenience, including a main floor powder room and a full family bathroom on the upper level.

Set on a quiet, tree-lined street in Chaplin Estates, the home is surrounded by beautifully maintained properties, offering a sense of calm, privacy, and timeless neighbourhood charm.

Moments from Yonge & Eglinton, with easy access to transit, parks, top schools, and a vibrant mix of local cafés and restaurants—this is midtown living at its best.

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