Tucked down a private road and high in the hills of northern Hillsdale, this well-built home offers sweeping mountain views, a beautiful pool, and more than 12 completely private acres--all within 10 minutes of town and 15 minutes from Great Barrington. The house is outfitted with thoughtful details that make country living comfortable and easy--central cooling, ample storage in all the right places, a two-car garage that opens into a mudroom and laundry room, en-suite baths in every bedroom, and a whole-house generator. The first-floor layout flows seamlessly, with two separate living rooms: one with a gas fireplace just off the dining room, and another farther down the hall with easy access to the guest bath. The kitchen is appointed with beautiful new soapstone countertops, a deep fireclay sink from Limoges, France, and a new gas range. At the end of the hall, the spacious and serene primary suite features a walk-in closet designed for two and a full bath with a walk-in shower and oversized soaking tub. The second floor opens to another sitting area and workspace, with two additional suites positioned at opposite ends for privacy. Each bedroom is generously sized, with ample storage and its own full bath. Throughout the home, every window frames a different perspective of the surrounding landscape, from far-reaching mountain views to layered shades of lush greens. On the lower level, a full basement offers abundant storage and workshop opportunities as is, or the opportunity to create additional living or entertainment rooms. Outside, the setting feels entirely its own. A fenced-in pool is surrounded by generous space for lounging and dining, while 12 acres of rolling hills and wooded forest invite exploration. The house sits at approximately 1,200 feet in elevation, with the property rising to nearly 2,300 feet, creating miles of private hiking and mountain biking with rewarding views from the summit. Located just 10 minutes from the center of Hillsdale, 15 minutes from Great Barrington, and 30 minutes from Hudson-- all while feeling a world away. Shepherd Hill is everything one might want in a home, set in a place everyone wishes to be.