Welcome to one of the most unique and versatile multi-family properties to ever hit the market in Sanford. At first glance, 106 High Street offers a rock-solid, highly functional duplex setup that is absolutely perfect for an investor or an owner-occupant looking to have their mortgage offset by rental income. The first-floor unit features two bedrooms, an updated bathroom, spacious living areas, and a cozy enclosed porch. Moving upstairs, the second-floor unit expands into a three-bedroom layout with a larger kitchen, separate laundry, dedicated attic storage, and its own enclosed porch. If this were just a standard duplex, it would already be a fantastic opportunity, but this property completely redefines the category with what is hiding right behind the main house. Tucked privately off High Street, the property boasts a massive secondary gated access point from Grammar Avenue, opening up a world of possibilities for a hobbyist, contractor, or car enthusiast. The backyard reveals an incredible, oversized garage setup, including a single-car bay and a massive two-car bay connected to a dedicated workshop space that leads directly into the home. Adjacent to the workshop is an absolutely massive three-season bonus room that offers an incredible footprint for entertaining, a home business, or the ultimate recreational hangout. To top off this property's extensive list of surprises, the home features a fully functional exterior elevator, providing effortless accessibility and convenience for moving groceries, furniture, or accessing the main floor without stairs. This is not just a multi-family home, it is a private hobby headquarters and a lifestyle compound all rolled into one. This very well could be one of the best deals currently available in the Sanford market. Schedule your private showing today to experience this one-of-a-kind property in person.