Set atop the sought-after heights of Caterpillar Hill, this exceptional 20? acre estate enjoys sweeping views across Eggemoggin Reach and offers a rare combination of privacy, acreage, and timeless Maine craftsmanship. Built by acclaimed local builder Michael Hewes, the residence encompasses over 3,800? square feet of thoughtfully designed living space with 4 bedrooms, 3 full baths, and 2 half baths across three levels. The home's dramatic central staircase and soaring wall of glass frame water views and fill the interior with natural light. Rich wood finishes, custom built-ins, and warm architectural details create an inviting atmosphere throughout. Multiple living and entertaining spaces include formal and informal gathering rooms, a dining room, library, and lower-level recreation room, offering flexibility for both everyday living and hosting guests. The spacious primary suite provides a private retreat with elevated views, while additional bedrooms and guest accommodations comfortably welcome family and friends. Radiant heat, extensive storage, and an attached two-car garage provide year-round comfort and functionality. Outside, the landscape captures the essence of Downeast Maine with a blend of open meadows, mature forest, and established blueberry grounds. Stone walls, multiple decks, and a screened porch create inviting spaces to enjoy summer sunsets over Eggemoggin Reach, abundant wildlife, and the changing seasons. Perched high above the coast, the property offers remarkable privacy while embracing the beauty of its natural surroundings. Ideally located just minutes from the villages of Sedgwick, Blue Hill, and Deer Isle, this custom and private estate places world-class sailing, protected harbors, acclaimed arts communities, fine dining, and endless outdoor recreation within easy reach. A rare opportunity to own a substantial legacy property with commanding water views in one of Maine's most coveted coastal settings.