This meticulously updated home blends timeless character with modern comfort, offering flexibility as a two-family or multi-generational single-family residence. Prior owners embraced multi-generational living, appreciating the spacious layout and exquisite built-ins that grace both living and dining rooms with elegance and timeless appeal. A grand central staircase links all 3 levels, while sun-drenched living areas flow seamlessly onto expansive, covered front porches. The first floor features a gas fireplace, and the second is warmed by a wood-burning Yodel stove. Both kitchens are thoughtfully renovated with vintage flair and include butler’s pantries. Thoughtful upgrades to all major systems ensure preserved historic integrity without compromising convenience. Lush landscaping with mature fruit trees, a generous backyard, & a two-car garage enhance the property’s appeal. Just steps from Winchester Center and the commuter rail, this home offers refined living in a prime location.