A rare investment opportunity on 1.43 acres inside the Winamac city limits, offering three distinct living spaces, multiple garages, and plenty of parking. This property provides excellent flexibility for investors seeking income potential, extended-stay arrangements, or multi-living configurations. The main residence includes a spacious main-level layout with four bedrooms, a full bath, large living room, formal dining or family room, and an updated kitchen featuring island seating space, built-in coffee bar, and included appliances. A rear mudroom/laundry area provides additional storage, utility sink, washer/dryer, and a convenient half bath. The upper level is accessible by an interior staircase as well as a separate exterior entrance, creating a natural second living area. The upper space includes a loft-style living room, kitchenette with breakfast nook, two bedrooms, and a full bath. This floor has operated independently in the past and offers excellent potential for a private suite or separate living quarters. An attached one-car garage, two additional storage bays, lean-to, and concrete side patio add on-site utility for tenants or owners. The deep 1.43-acre lot extends to the rear tree line with the Panhandle Pathway located just beyond the back of the property. A second detached dwelling further enhances income options. This single-story structure includes an open kitchen and living area (appliances included), two bedrooms, a full bath, and its own attached garage (no direct interior access). Previously leased, this dwelling offers immediate or long-term rental potential. With versatile living spaces, multiple entrances, separate electric meters, abundant parking, and a desirable in-town acreage setting, this property presents numerous configuration options for investors or owner-occupants seeking supplemental income. A unique opportunity to acquire a flexible multi-living property in Winamac with room to expand, customize, or optimize rental arrangements.