Available for the first time in 25 years! This exceptional West Roxbury two-family at 42-44 Sanborn Ave offers a rare opportunity on a quiet, tree-lined street near Centre Street shops, commuter rail, and Millennium Park. Set on a 5,663 sq ft lot with 4-car parking and over 3,100 sq ft of versatile living space, this charming yellow shingle-style property features a covered portico and high ceilings. It is ideal for an owner-occupant looking to offset the mortgage or an investor seeking a strong asset with a projected 6% cap rate. The first-floor unit features 2 bedrooms plus an office, gleaming hardwood floors with original dark wood trim, and a classic fireplace living room. The upper unit offers 3 bedrooms plus a sunroom and finished oversized attic, featuring beautiful hardwood floors, an updated eat-in kitchen with newer white cabinetry and stainless steel gas range, plus a renovated main bath. A rare blend of space, character, income potential, and location!