Presenting a truly exceptional and rare offering in Pasadena's highly coveted Madison Heights neighborhood: an opportunity to acquire two distinct residences on a single expansive lot. This unique property caters to a variety of lifestyles, whether you're an astute investor seeking dual income streams or a homeowner desiring a supplemental rental income while residing in one of the homes. The Front House, a graceful 1,361 SF Craftsman, immediately captivates with its welcoming wrap-around front porch and sturdy clinker brick and stone piers. Step inside to discover gleaming hardwood floors that extend throughout the home, highlighting the elegant craftsmanship of the era. The spacious layout includes three charming bedrooms and a newly renovated full bathroom showcasing modern fixtures and finishes. The heart of this home is its updated eat-in kitchen, boasting an array of stainless steel appliances that cater to culinary enthusiasts. Adjacent to the kitchen, the formal dining room is a true entertainer's delight, complete with original built-in cabinets that offer both aesthetic appeal and practical storage. This front house is truly move-in ready, having undergone significant enhancements, including a new roof, the convenience of central heating and air conditioning, new copper plumbing (2025), and fresh paint throughout the interior and exterior, ensuring a pristine living environment. Outside, the property offers both a private front and rear yard, providing idyllic spaces for entertaining guests or simply savoring your morning coffee in tranquility. The private rear yard features newly installed sod and new irrigation, in addition to a tall privacy hedge and mature fruit trees. The Back House is a charming 705 SF Cottage-style home, currently tenant-occupied, with 2 bedrooms and a pristine full bath. Adding appeal to this home is central air, hardwood floors throughout, and a lovely eat-in kitchen. The two-car garage was rebuilt; each home uses one garage space. The roofs on all structures were updated in 2023. This versatile setup presents an ideal scenario for an investor to have two income streams from two independent homes on one property. This is an extraordinary chance to own a classic in one of Pasadena's most desirable neighborhoods.