Welcome to 44 Indian Rd Cres, a character-filled sanctuary on a rare, private ravine lot extending to the bottom of the hill in coveted High Park N. Blending timeless architectural charm with thoughtful modern updates, this residence showcases exquisite craftsmanship throughout. A flagstone walkway, majestic birch tree, & perennial gardens frame stunning curb appeal, while the private rear oasis features a covered deck (23') with skylights & privacy screens, plus a shady, secluded deck hidden at the bottom of the garden-surrounded by blooming flora & access to the 1-car garage.The main level is built for effortless entertaining. A formal dining room boasts rich hardwood, a turn-of-the-century chandelier, & slab radiator covers. The light-filled living room features an original wood-burning fireplace & double doors to the deck. The renovated chef's kitchen (07') offers cork flooring, quartz counters, a farmhouse sink, glass backsplash, & premium appliances with an upgraded dishwasher (24'). Accentuated by solid front & back doors (08') & custom windows (13'), comfort is guaranteed year-round with an updated furnace, chimney liner, & water heater (24-25'), plus central AC (10') & roof replaced (19').Upstairs, the primary retreat includes hardwood floors & a W/I closet. A 2nd bedroom with a W/I closet connects via French doors to a flexible 3rd room-ideal as a nursery, study, or standard bedroom. All upstairs rooms feature custom blinds (25'). The fully renovated 4-pc bath (19') offers a deep soaker tub, rain showerhead, niche, & subway tile.The finished lower level (13') maximizes space with a cozy rec room, plush broadloom, pot lights, 3 above-grade windows with custom blinds (22'), extensive custom built-ins, cedar closet, & utility room workbench. A spa-inspired 3-pc bath features heated floors & rain shower beside a stacked LG laundry suite (washer 24').Steps from top schools (Indian Road Crescent Jr PS, Humberside CI), High Park, BWV, & Keele station.