Gilbert's Hill, the very best of Vermont living - Iconic, 112-acre estate with a storybook history as the first “modern” ski run in the US. Located two miles from the village center of Woodstock, the “prettiest small town in America", experience rural peace with convenient access to great restaurants and shops. Turnkey, fully-restored Vermont farmstead - a picturesque family compound with 7 historic structures including: 1830s Greek-revival farmhouse with bright natural light (4BR, 2 bathrooms with showers, 11 rooms total, including custom-built modern farmhouse kitchen); authentic ski lodge/guest house (2BR, 1 full bath, 6 rooms total); 1700s sleigh barn/family room with floor-to-ceiling glass, full kitchen, half bath, private deck and fireplace; restored original dairy barn with bar, dance floor and loft; modern greenhouse conservatory with its own half bath, wood stove and outdoor pavilion; farmhouse extension with garage, loft, and mudroom; detached, 5-bay shed for cars and equipment; and vintage milk house (all with ample room for expansion). A natural paradise - with stunning, unspoiled views, a huge sugar maple grove, stone walls, vineyards and acres of wildflower meadows, this property offers serene trails and expansive outdoor space. Onsite opportunities include: ski-in/ski-out, snowboarding and sledding (install your own private lift); hiking; trail running; wildlife watching; horseback riding; maple syrup production (sugaring), and the finest fall foliage, star gazing and firefly shows in New England. Nearby is the Woodstock Country Club with golf, tennis, spa and pool; multiple streams, rivers and lakes for fishing/swimming; the Green Mountain Horse Association with miles of trails; the Marsh-Billings-Rockefeller National Park carriage paths; quaint general stores, and easy access to world-class downhill skiing/mountain biking at Saskadena Six and Killington. Flood Data incorrect: Minimal/Low Flood Risk.