Set on one of downtown Orangeville's most sought-after historic streets, this extraordinary red brick century home w/ unmistakable personality blends Edwardian architecture w/ a refined, modern aesthetic that feels both elevated & inviting. Rich in texture & layered w/ thoughtful detail, it offers a moodier, more tailored feel rarely found in historic homes. Unforgettable curb appeal w/ original brickwork, stone accents, steep rooflines & mature trees for a timeless presence. Inside, engineered hardwood floors, oversized windows & dramatic lighting bring warmth & designer style throughout. Formal living & dining spaces honour the home's original character while flowing effortlessly into the updated kitchen & rear addition for a layout that feels far more contemporary than expected. Kitchen balances beauty & function w/ quartz countertops, custom cabinetry, herringbone backsplash, pantry storage, high-end appliances & peninsula island that naturally becomes the centre of every gathering. Heated stone floors in foyer & powder room add everyday luxury, while major updates incl roof, furnace, AC & electrical panel provide peace of mind behind the scenes. Family room completely transforms the atmosphere. Bright & expansive w/ detailed wall mouldings & oversized black-framed sliding doors, it's polished yet relaxed while opening seamlessly to the backyard. Outside, a sprawling deck surrounds the impressive 10-person swim spa w/ multiple lounge spaces, mature trees, warm wood tones & private setting that feels tucked away from the rest of downtown. Upstairs fts calming bedrooms, oversized windows, updated lighting & beautifully finished bath w/ classic subway tile, warm wood & brass accents for a timeless finish. Bonus lower level feels elevated w/ acoustic fluted wall detailing, oversized mirrors & boutique fitness aesthetic. The loft = ultimate retreat w/ vaulted wood-clad ceilings, dark floors, gas fireplace, built-in desk & updated 3pc bath.