Properties Near 1362 Barnard Road Woodstock, VT

2 PLEASANT STREET- This stately brick Federal is a historic landmark property in the heart of Woodstock Village, home to many storied families in the town and state’s history, notably Julius Converse, Governor of Vermont in 1872, and Laurance Rockefeller. Though it has been well-renovated and maintained over the years, it retains many of its historic features to beautifully blend modern convenience with original charm. The first floor features oversized, recently updated windows and several spacious high ceiling gathering rooms including a formal living room, dining room, library, and central family room. A cozy eat-in kitchen with fireplace on the north side of the house opens to a lovely landscaped yard shaded by mature maple trees. The second floor, also punctuated by high ceilings and windows to give it a bright and spacious feel, features a primary bedroom on the front side of the house with an adjoining dressing area, walk in closets, and full bath. Adjacent the primary is another sizable bedroom with its own bath, while two additional bedrooms with shared bath round out the level. The detached barn garage has space for one car and plenty of additional storage. Idyllically sited and within walking distance of local shopping, dining, schools, hiking trails, and Marsh-Billings-Rockefeller National Historic Park, this iconic Woodstock home is a rare gem.

Gilbert’s Hill is one of Vermont’s most celebrated properties and a national landmark for its contribution to the sport of alpine skiing. Spanning 112.88± acres in Woodstock (79.31 acres) and Pomfret (33.57 acres), the farm is recognized as the birthplace of lift-served skiing in America, where the first rope tow was installed in 1934. Today, its open pastures, rolling terrain, and historic ski hill remain wonderfully intact — a living landscape that forever changed the trajectory of winter sport and the development of recreational skiing in the United States. At the heart of the property is a restored circa 1855 Greek Revival brick farmhouse with four bedrooms, two bathrooms, and a classic mid-19th-century clapboard addition with kitchen and garage. Original details have been thoughtfully preserved, blending historic integrity with comfort and charm. Surrounding the main house is a collection of restored historic buildings, including: a 1934 ski hut, now a cozy two-bedroom cottage with full kitchen and bathroom; a carriage barn with full kitchen and half bathroom; a dairy barn with milking parlor and six stanchions; and the original milk house. There is also a modern greenhouse pavilion with half bathroom and a detached 4-bay equipment shed. The land, which includes a vineyard with 700 vines, is conserved with the Vermont Land Trust. The house, dairy barn, milk house and 1934 ski hut are also protected by a historic preservation easement.

This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont’s most beloved communities. Woodstock is often hailed as “the prettiest small town in America,” and for good reason. The village is a vibrant resort town with maple-lined streets, stately homes, artisanal boutiques, and a warm and welcoming spirit. The town and assorted local organizations offer cultural and family fun activities offered throughout the year. Currently being used as a 7-room Inn boasting an additional 2-bedroom owner’s quarters, this property could be returned to operating as a private residential property with zoning permit. Please contact for more information on making this beautiful place your dream home!