Set within Poughkeepsie's sought-after historic South Side, this beautifully preserved circa-1900 Italianate Victorian offers a rare opportunity to own a four-unit property rich in architectural character and income potential. The freshly repainted exterior showcases classic Victorian detailing and an elegant wraparound verandah leading to a private backyard. Off-street parking and a substantial basement storage area add everyday convenience. Inside, thoughtfully renovated interiors blend historic charm with modern comfort. Original hardwood floors, soaring ceilings, and decorative marble fireplaces reflect the home's heritage, while updated kitchens and flexible layouts support a variety of living arrangements. The property is currently configured as four legal units with separate gas and electric meters, with the potential for easy conversion back to a single-family residence. The house is brick-insulated on all floors, including the attic space. Highlights: Unit 1 - Expansive one-bedroom residence featuring a formal dining room, 11-foot ceilings, hardwood floors, three decorative marble fireplaces, a full kitchen, and a bonus room ideal for office or studio use. Unit 2 - Bright one-bedroom unit with hardwood floors, two decorative fireplaces, and a full kitchen. Unit 3 - Two-bedroom residence spanning two levels, offering hardwood floors, a decorative fireplace, a full kitchen, and generous storage. Unit 4 - Garden-level studio with decorative fireplace and kitchenette, currently utilized as a common laundry center. The property is presently operated as mid-term furnished rentals and may be delivered furnished or unfurnished. Conveniently located near parks, historic homes, Metro North/Amtrak Train Station, Vassar, Marist, Culinary Institute, Walkway over the Hudson, Vassar Brothers Medical, this distinctive Victorian presents a versatile opportunity for investors or those seeking a historically significant residence with income flexibility. A standout offering in one of Poughkeepsie's most architecturally rich neighborhoods.