A distinguished offering in the heart of Winter Harbor, this exceptional property encompasses two turnkey residences on a single parcel, thoughtfully positioned to capture views of the harbor while enjoying the convenience of village living. Held by the same owners for more than two decades, the property presents a compelling opportunity for investment, multi-generational living, or a private coastal retreat with income-producing potential. The primary residence is a beautifully maintained turn-of-the-century home offering three bedrooms and two baths, rich in character and timeless New England charm. Complementing the main house is a separate two-bedroom, two-bath residence that has generated a strong and consistent vacation rental history over the past fifteen years. Just a short stroll from the village's shops, restaurants, public boat launch, and everyday conveniences, both residences offer an enviable lifestyle in one of Downeast Maine's most authentic coastal communities. Live in one home and rent the other, establish a family compound, or continue operating both as income-producing properties. This residence is ideally situated near the Schoodic Peninsula and Acadia National Park, with access to miles of scenic hiking trails, rugged granite shoreline, and some of Maine's most breathtaking coastal scenery. As a turnkey offering in one of Downeast Maine's most desirable waterfront communities, it combines historic character, proven income potential, and an exceptional location. This is a legacy property ready for its next chapter.