So Many Highlights on Highbourne! Welcome to this rare gem, perfectly situated in a lovely pocket where Forest Hill, Chaplin Estates, and Yonge & St. Clair all come together. This legal triplex is the definition of turnkey: a smart investment with charm, flexibility, and location all wrapped in one. Set on a premium lot and offering undeniable curb appeal, this beautifully maintained and thoughtfully updated home features three spacious, separately metered units. Each unit has its own private entrance, generous layout, and updated kitchen. The main and second-floor suites each feature three large bedrooms, hardwood flooring in the principal rooms, bright bay windows, and stylish four-piece baths. Original woodburning fireplaces add warmth and character, and rear exits for both units provide extra privacy and functionality. The lower-level unit is spacious and inviting, with two bedrooms, an open-concept kitchen/living/dining area, a walk-in closet, a discreet side entrance, and a rare walk-out to a lovely backyard terrace. Enjoy a private driveway and ample covered parking under the oversized carport. Stroll down the peaceful tree-lined street to nearby cafes, shops, and restaurants. Nature lovers and fitness enthusiasts will appreciate the close proximity to the Beltline Trail, and families will love the access to top-notch public schools- Deer Park Jr. & Sr. PS and North Toronto CI, and to elite private options, such as UCC and BSS. A pleasant walk to both Davisville and St. Clair subway stations and an easy commute downtown.