Nestled on 18+ secluded acres along one of Hillsdale's most bucolic and sought-after roads, this solidly built country home offers endless potential. Located just minutes from the Massachusetts border on the edge of the Berkshires and only 15 minutes from Great Barrington, this property provides the perfect balance of peaceful rural living and convenient access to the region's renowned cultural, dining, and outdoor attractions. The home is filled with warmth and character with beautiful natural wood details throughout. A spacious through-house living room serves as the heart of the home, anchored by a striking stone wood-burning fireplace complete with an indoor grill. A large sunroom extends the living space, offering the perfect spot to enjoy the surrounding landscape in every season. The residence features two bedrooms, two full bathrooms and a half bath, as well as a freshly painted 400+sf attic with heat and air conditioning and 5 windows, providing flexibility for guests and home office space. Approached by a long, meandering gated driveway, the property offers exceptional privacy. The entire acreage is enclosed with deer fencing, creating a secure environment for gardens, pets, or livestock. Outdoor enthusiasts will appreciate the property's many unique features, including a large fenced dog run that could easily accommodate horses or other animals. A picturesque pond, once a beloved local swimming hole, adds to the property's appeal. On the water's edge is a grand double-sided stone fireplace, presenting a remarkable opportunity to create outdoor entertaining and dining overlooking the water. There is a full basement with an integrated garage space currently used as a workshop, a detached two-car garage with substantial storage and extra square footage previously utilized for animals, and a charming pole barn ideal for lawn equipment, hobbies, or additional storage. Recently trenched and updated power and fiber optic and new septic piping. A truly special Hillsdale property offering privacy, natural beauty, and the opportunity to create your own Hudson Valley and Berkshires retreat.