An incredible opportunity awaits to own this elegant 1860 Greek Revival in Portland's desirable Munjoy Hill neighborhood, complete with a spacious yard, two-car garage, and income-generating apartment. Whether you're looking for a multi-generational home, rental income, or simply want to enjoy the entire space as your own retreat, this property offers flexibility and enduring value. The owner's unit, positioned at the front of the lot, is a fully independent residence rich with historic character and thoughtful updates, including a brand new furnace installed in February 2025. The first floor features a gracious entry, a formal drawing room, and a charming ''summer kitchen'' that opens directly to the backyard; ideal for guest suite use, with its own full bath. Upstairs, you'll appreciate the original tin ceilings, wainscoting, and hardwood floors. The updated kitchen flows into a south-facing, sun-filled double parlor with an open living & dining space, high ceilings and water views. An en-suite bedroom with a full bath completes this floor. The top level serves as a private primary suite with a full bathroom, a cozy library or office, and a spacious bedroom. The second unit is a bright and spacious five-room apartment with a private entrance, outdoor deck, and excellent rental history, ideal for income or guest accommodations. Outside, enjoy professionally landscaped grounds, harbor peaks from the deck, and room to garden and relax. Updated systems include air conditioning, high-efficiency windows, newer plumbing/electrical, a central vacuum system, full winterization for energy savings, and a whole-house generator. Ample storage in both the attic and basement completes the picture. All this in Portland's vibrant East End where you're just steps from the Eastern Prom, East End Beach, and favorites like BLVL Bakery, The Front Room, and Jing Yan Tavern. Come experience this hilltop beauty, and watch the ships sail by from your very own hilltop escape.