21 York Street, Orangeville, ON

Finally, a way into one of downtown Orangeville's most coveted streets without needing a $1.5M budget. Built in 1938 and set on a massive mature lot, this home is full of character, flexibility, and future potential. Offering 5 bedrooms above grade, multiple walkouts, ample parking, a detached shop with hydro, original hardwood floors, and crystal hardware throughout, every inch of this property tells a story. The upper level once functioned as its own living space, with the 5th bedroom featuring a kitchenette, while the basement walks out directly to the backyard creating endless possibilities for multigenerational living, income potential, or a forever family home with room to evolve over time. Thoughtfully updated where it counts, including a newer furnace, A/C and hot water tank, water softener with carbon filtration (1 year old), reverse osmosis system (2.5 years old), newer appliances including stove (5 years old), fridge, dishwasher, and washing machine (all 1 year old), plus a new kitchen and living room ceiling and brand-new eaves (2026). Located just steps from the infamous Christmas in the Park and Kay Cee Gardens, this is the kind of property that rewards creativity, vision, and care all while getting you into one of Orangeville's most sought-after neighbourhoods.