Welcome to 560 N. 2nd Avenue—a truly special home with an attached ADU in the heart of Historic Downtown Upland. Rich in character and thoughtfully updated, this beautifully maintained Craftsman offers the rare combination of timeless charm, flexible living space, and investment potential—all just moments from restaurants, coffee shops, breweries, boutique shopping, the weekly farmers market, and Upland's beloved annual Holiday Parade and year-round downtown festivities. Situated on an approximately 7,500-square-foot lot, the property features a spacious front residence plus an attached ADU with its own private entrance, making it ideal for multi-generational living, rental income, a private guest suite, or a dedicated home office. The front main house offers two spacious bedrooms, one beautifully updated bathroom, an open-concept living and dining area, and a huge upstairs loft that is set up to add an additional bathroom. This versatile space could easily serve as a third bedroom, game room, office, or creative studio. Hardwood flooring, granite countertops, stainless steel appliances, updated cabinetry, recessed lighting, a large laundry room, and central heating and air conditioning blend historic character with modern comfort. The attached ADU features one bedroom, one bathroom, its own kitchen, living area, private entrance, and separate gas and electric meters, creating an exceptional opportunity for extended family, guests, or supplemental rental income. Car enthusiasts will appreciate the impressive detached oversized four-car tandem garage and expansive alley-access driveway, providing abundant off-street parking with room for multiple vehicles, boats, RVs, recreational toys, or future workshop possibilities. An additional front driveway provides even more parking and convenience. The spacious backyard is perfect for entertaining, offering plenty of room for BBQs and gatherings. Whether you're relaxing around the fire pit, lounging beneath the pergola, or taking advantage of the expansive lawn, the outdoor space offers the perfect balance of hardscape and green space for year-round enjoyment. Whether you're searching for your forever home, an income-producing property, or the perfect setup for extended family, this one-of-a-kind property truly checks nearly every box.