There are properties that offer acreage, and then there are properties that offer a way of life. Set along one of the region's most picturesque and peaceful country roads, this extraordinary 153+ acre estate is a place where summer afternoons are spent fishing at the pond, tennis matches stretch into golden evenings, and loved ones gather beneath vast mountain skies. With extensive road frontage along Goshen Street and Crammer Road, this rare residential compound features two separate homes thoughtfully positioned on opposite sides of the road. Ideal for guests, extended family, a caretaker, or events, each residence enjoys privacy while remaining part of one cohesive estate. The main house offers an immediate feeling of comfort the moment you step inside. Its inviting living room features a vaulted ceiling with exposed beams, a wood-burning fireplace with insert, and windows framing gorgeous, direct views of Hunter Mountain's ski slopes and the property's picturesque pond. A covered porch and stone patio extend the living space outdoors, creating peaceful places to enjoy the remarkable scenery. The home offers three bedrooms, including a convenient first-floor primary suite. Across the road, the Cape-style residence features three bedrooms, two bathrooms, and an oversized garage, with the private tennis court nearby. Rolling meadows framed by classic white picket fencing sweep across the landscape, while the shimmering fishing pond reflects the changing sky. A beautiful and structurally sound two-story dairy barn (FB3), measuring approximately 55' x 31', adds character, history, and exciting possibilities for future use. The property also offers substantial acreage with the potential to build additional homes. Possible building areas may provide pond and mountain views, with the potential for views of Hunter Mountain's ski slopes as well. Extensive road frontage, varied terrain, and an exceptional natural setting create opportunities to realize a broader vision while preserving the property's privacy and beauty. Perfectly positioned between Hunter Mountain and Windham Mountain, the estate offers complete tranquility with convenient access to skiing, golf, hiking, dining, and year-round recreation. Properties of this scale, beauty, and versatility rarely become available. More than a home, this is a legacy estate - a place where holidays become traditions, summers seem endless, and loved ones return year after year. 3D virtual walkthroughs of both homes and drone video of the property are linked. Please request them if they are not visible on the listing website.