Set on 20 picturesque acres, this beautifully updated 1896 Farmhouse offers the perfect blend of timeless New England character, modern comfort, and peaceful country living! Featuring 4 bedrooms, 2 full bathrooms, and a massive multi-level barn, this property provides plenty of room to spread out while maintaining the warmth and charm of its farmhouse roots. The gorgeous, updated main level features a light and bright kitchen with granite countertops, a large island/breakfast bar, and access to the partial wraparound deck overlooking the beautiful surrounding landscape. Abundant wildlife, an orchard with apple and pear trees, expansive open space, and endless opportunities for gardening and recreation create an incredible country setting. An expansive barn adds even more character and versatility, with plenty of room for animals, storage, hobbies, or agricultural use. Horse stalls built in 2024. Barn doors open for direct hay access; no hay elevator needed! Inside, the main level also offers a full bathroom, spacious sunroom, dining area, living room, family room, and a laundry/mudroom with access to the second floor. Upstairs, you'll find all 4 bedrooms and an additional full bathroom, along with a walk-up attic offering exciting potential for future expansion and customization. The property also includes a separate additional structure with Certificate of Occupancy, offering exciting potential to be renovated into guest accommodations, a short-term rental, studio space, or other flexible use, subject to obtaining the appropriate permits and approvals. Additional features include two high-efficiency propane furnaces, new HVAC and Tesla battery and numerous updates throughout. Otis Reservoir is approximately five minutes away for boating and beach days, while skiing, hiking, and access to the Appalachian Trail are all nearby. Enjoy easy access to Great Barrington and many of Western Massachusetts' renowned cultural destinations, including Tanglewood, Jacob's Pillow, the Norman Rockwell Museum, Chesterwood, and Hancock Shaker Village. Approximately two hours from Boston and three hours from New York City, this one-of-a-kind property offers a truly special country retreat. Schedule your showing today!