Exceptional 8 bedroom, 5.5 bath home located in the city of Winchester, offering space, luxury, and thoughtful updates throughout. The 3-car side-entry garage includes a convenient half bath. Enjoy outdoor living with covered front and side porches, a spacious covered rear deck, and a lawn sprinkler system in the front yard. The gourmet kitchen featuring Jenn-Air appliances, upgraded cherry cabinetry, a center island, and a walk-in pantry. Hardwood and tile floors flow throughout the main levels, while the lower level recreation room boasts durable waterproof laminate flooring. The expansive primary suite includes a gas fireplace and a private mini bar/coffee bar with a sink—perfect for added comfort. The bedroom-level laundry room is fully equipped with cabinets and a utility sink. Modern systems include two furnaces, three heat pumps, a sump pump, a central vacuum, and an AM/FM intercom system. Recent updates include: roof (2023), HVAC systems serviced and updated (attic 2024, basement 2021), and a water softener (2025). This home offers ideal multi-generational or large family living with thoughtful upgrades in every corner. See the virtual tour attached to this listing!