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 by 130 foot 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 and 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 and the 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.