Step back in time and experience the maritime heritage of Waldoboro in this beautifully maintained 1850 Cape Cod-style home, ideally situated in the town's historic ''Shipyard'' district—once home to the construction of the famed five-masted schooners. Just minutes from downtown & the town landing, this property offers a perfect blend of historic charm & modern comfort. A welcoming covered porch invites you to relax and enjoy the salty coastal breeze. Inside, a functional mudroom provides the ideal space to kick off boots and hang coats. The updated kitchen combines timeless character with modern convenience, featuring newer flooring and appliances, granite countertops, a moveable center island, and a spacious pantry—perfect for a coffee station or prep area. The kitchen opens to a cozy living room warmed by a Hearthstone cast iron and soapstone wood stove, with pine floors, built-in cabinetry, and a ceiling fan adding to the inviting atmosphere. At the front of the home, two elegant parlors reflect its historic roots. The formal dining room boasts wide pine flooring, built-ins, and ornate tin ceilings, while the adjacent sitting room features wood floors, two closets, and a stunning Thomaston marble fireplace. A full bath and a flexible first-floor bedroom or bonus room enhance the home's functionality. Upstairs, you'll find 3 additional bedrooms, including a primary suite w/ practical cork flooring & cozy knotty pine walls & ceiling. Adjacent to the primary bedroom is a full bathroom and a convenient laundry room. The attached barn provides additional space, with a large second-floor area and a cedar closet. The home is also equipped w/ a 13KW on-demand Generac generator for added peace of mind. Set on .53 acres of lovely landscaped grounds w/water views of the Medomak River, the property features 2 additional decks—ideal for alfresco dining or gatherings around a fire pit. This is a wonderful opportunity to own a piece of Waldoboro's seafaring past!