MULTI-GENERATIONAL LIVING ... Character, space & versatility come together at 287 Main St E in Grimsby, a charming 2-storey (legal duplex) home offering thoughtfully designed living across 2,874+ sq ft on a generous 54' x 164' property w/POOL & mature trees. Ideal for extended families or those seeking flexible living arrangements or potential income, this home provides distinct yet connected spaces for everyday comfort. The BEAUTIFULLY UPDATED main level blends classic charm w/modern function. Welcoming 3-season/mudRm leads into a bright livRm featuring engineered hdwd flooring, large windows, crown moulding & electric fireplace. Approx. 10' ceilings & original trim preserve the timeless character of this CENTURY HOME. The spacious dining/great room is perfect for family gatherings, while a large 4-pc bath w/skylight adds natural light. Kitchen offers vinyl flooring, accent wall & access to bsmt. Just beyond, a versatile famRm (or bedRm) sits alongside the MF primary bedRm w/WALK-IN closet. Patio doors lead to composite deck connecting to an upper deck overlooking fully fenced yard, patio area & AG POOL. Private upper-level is ideal for extended family or independent living. This space features a large primary bedRm w/WALK-IN closet (currently a livRm), add'l bedRm, third bedRm (currently sitting room) & 4-pc bath. A retro VINTAGE kitchen w/island & dining area adds charm, complete w/window overlooking deck. FULLY FIN'D LOWER LEVEL offers additional living flexibility w/SEPARATE ENTRY, O/C living area, full kitchen w/potlights, 3-pc bath w/updated shower, laundry access, spacious bedRm & WALK-UP to exterior - perfect for in-laws, adult children, guests, or growing families. Mechanical highlights include 2 metres, owned furnace & A/C, reinsulated attic, roof & eaves (approx. 2013), mostly newer windows & bsmt utility/storage w/second 100-amp panel. Conveniently located close to schools, hospital & HWY access. CLICK ON MULTIMEDIA for virtual tour, floor plans & more.