Distinctive architectural character meets modern comfort in coveted Chaplin Estates. Situated on a30' x 124' lot on a quiet, tree-lined avenue, this handsome detached two-storey residence showcases rich period details and exceptional lifestyle flexibility. A welcoming covered front porch opens to gracious principal rooms featuring warm natural gumwood trim, plate rails, beamed/wainscoted millwork, authentic stained-glass windows, and rich (new) hardwood flooring. The generous living room is anchored by a classic brick fireplace with raised hearth and a deep bay window framing views of the front yard. Host memorable gatherings in the formal, full-panelled dining room framed by French doors. The updated kitchen boasts quartz countertops, custom white cabinetry, ceramic backsplash, Miele refrigerator plus secondary bar fridge, and a convenient breakfast pass-through bar. At the rear, an inviting family room and breakfast area features French doors opening out to a private sun deck and a deep, fully fenced backyard. Upstairs offers 3 bedrooms, upper hallway built-in linen storage, a convenient laundry shoot and an updated 3-pc family bath with quartz-topped vanity and glass walk-in shower. The spacious primary bedroom includes wall-to-wall closets and built-in cabinetry. The second and third bedrooms have double closets plus direct walk-out access to a massive private rooftop deck overlooking backyard. The finished lower level (813 sq ft) offers outstanding in-law or guest suite versatility with a separate side entrance, full kitchenette, bright recreation room, den/potential 4th bedroom with double closets, 3-pc bath and large laundry/utility room. Detached 1-car garage plus driveway parking (legal parking is 1 car in garage; homeowner and neighbour currently both park a 2nd car in the driveway without issue). Steps to top-ranked public/private schools, beltline trail, parks, libraries, dining, boutique shops, and TTC Subway/Eglinton Crosstown LRT.