This beautifully preserved New Englander home blends classic architecture with thoughtful updates in one of Greater Portland's most sought-after locations. A welcoming front hall showcases the home's original character with an elegant staircase and period millwork, inviting you inside to explore the expansive and flexible layout. The formal living room is anchored by a gas fireplace, while the comfortable family room overlooking the rear yard features a cozy heat stove. The updated kitchen includes a walk-in pantry and adjacent dining area. A full bath and additional room currently used as a bedroom complete the first floor. All of this flows seamlessly to an expansive tiered deck with hot tub, overlooking the private backyard and pool area. A spacious bonus room with half bath reached by its own staircase from the family room functions as a home office, playroom, guest space or future primary ensuite with conversion of the existing half bath to a full bath. Follow the original staircase from the front hall to the second and third floors, with each level offering a full bath and multiple bedrooms. Outside, the pool area calls for relaxation. The pool house is a legal ADU with kitchenette, sitting area, half-bath and laundry opening onto the pool deck, plus a bedroom and full bath upstairs, offering 864 sf of additional living space. Whether used for guests, entertaining, or rental income, it offers endless possibilities. Many improvements--heat pumps, whole-house automatic generator, solar panels, irrigation system, and more--enhance comfort, efficiency, and peace of mind. Life in Cumberland offers the best of coastal Maine, with award-winning schools, a welcoming community, and abundant outdoor recreation. Nearby Broad Cove Reserve offers 23 acres of protected shoreline with sandy beach, pier, and walking trails just steps from your door. Enjoy the beauty of the Foreside with Portland's acclaimed restaurants, shopping, and arts scene just a short drive away.