First time on the market, this rare Upland opportunity offers TWO DETACHED HOMES on one property at 505 N. Eighth Ave and 763 N. Arrow Highway. This is the kind of property buyers wait for and rarely find. Perfect for multi-generational living, extended family, parents and adult children, or anyone looking for two separate homes that allow loved ones to stay close without giving up privacy or independence. Together, the homes offer approximately 2,416 total square feet with a combined 5 bedrooms and 2 bathrooms. Home 1 with great front porch at 505 N. Eighth Ave features 3 bedrooms, 1 bathroom, and a small backyard. The SECOND home at 763 N. Arrow Highway offers 2 bedrooms, 1 bathroom, and a carport enclosed for a garage-like experience. One home in front, one home right behind it, both detached, both full of possibility. This property is more than a real estate purchase. It is a chance to create a lifestyle that works for real life. Imagine aging parents nearby, adult children building independence while staying connected, or loved ones close enough to share everyday moments while still having a place of their own. Setups like this are hard to find and even harder to replace. The property has been cared for over the years with improvements that add value and peace of mind, including kitchen and bathroom plumbing updates in the front home, a sprinkler system, and a newer sewer line running from the back house to the street. Both homes are connected to one sewer line. The rear home also features a bathroom remodel completed approximately 8 years ago and exterior paint completed approximately 4 years ago. Currently tenant occupied and never before offered on the market, this is a unique opportunity with flexibility for today and potential for tomorrow. Located in the desirable City of Upland, near shopping, dining, schools, parks, and commuter access, this property offers convenience, function, and long-term appeal. Opportunities like this do not come around often. Two detached homes. One special property. Endless possibilities. So schedule your private tour today because home starts with you!