Woodstock, VT —
"Prettiest Small Town in America"

Welcome to Woodstock, Vermont. This stunning country town is just waiting to be explored, with its wealth of beautiful hiking trails, museums and historic landmarks as well as enough events to fill any schedule, no matter the interests of its owner. The endless opportunities for tranquility and activity make this town perfect for any visitor or potential resident. Come, relax, unwind and let Woodstock lead the way.

A town in the Green Mountains of Windsor County
A 2 hour and 20 minute drive to or from Boston, MA
Getting Here
Follow I-93 N until the merge onto I-89 N into Vermont. Exit 1 onto US-4/Woodstock Road will lead you to your destination

"The beautiful Rockefeller Mansion offers tours from Spring through Foliage."

The beautiful Rockefeller Mansion, which has an outstanding collection of paintings from Hudson Valley Artists, offers tours from Spring through Foliage. A visit to the Billings Farm is a must. The farm offers sleigh rides during the winter months and an informative tour year round. A feature documentary on most Saturday afternoons attracts many.

Cloudland Farm, located on the edge of Pomfret, Vermont, offers Farm to Table dinners Friday and Saturday evenings. Feel like cooking at home? The Woodstock Farmer’s market has the best selection of local meats, seafood and produce along with an extensive wine, cheese and beer selection.

"Outdoor activities are numerous!"

Outdoor activities are numerous! The winter months offer the opportunity to Cross Country ski, snowshoe or ride Fat Bikes on the Woodstock Inn golf course or Downhill at Suicide Six. Killington is within twenty minutes to the west and Okemo is a 30 minute drive away. If you prefer a massage or a place to relax, the Woodstock Inn Spa or the Strong House Spa in Quechee both offer many treatment options. Golfing, tennis, fly fishing, falconry, and biking are all available. The renowned Green Mountain Horse Association is active with shows from April through November.
For primary or secondary home-owners, Woodstock is an active community for all ages!

Featured Listings

58 Pleasant Street, Woodstock, VT 05091

$2,000 per month
Rejuvinated East End of Woodstock Village! The Main level of this building is ready to be utilized. A store, a restaurant, a bakery, an art gallery, bike rental, kayak rental, etc - the possibilities are endless. The building complies with ADA regulations. There is a room to be converted to a kitchen if one chooses to use the space in that manner, along with plenty of storage upstairs. Tenant can put their finishing touches on the space. Heat and Electricity included in rental amount

45 Elm Street, Woodstock, VT 05091

An unexpected opportunity, to acquire the prime undeveloped parcel of land along the banks of the Ottauquechee River, within the very heart of Woodstock Village! The 2.5 +/- acres benefit from an extensive, level, and quiet location along an accessible, wide and beautiful expanse of the river. With frontage at 45 Elm Street, there is presented an address with well deserved prestige! This Elm Street access can provide the site for an highly visible and substantial residence, or it can be the graceful entry to a quiet, privately situated residence, with full river views. On the edge of the parcel is a classic bungalow, in need of renovation, which may be removed if the river view site is desired for another structure. This 2.5 +/- acre river front parcel, in the heart of Woodstock, is an opportunity which can't be duplicated!

336 Stone Bridge Way, Woodstock, VT 05091

Magnificent South Woodstock family compound! The estate is composed of a main residence, substantial guest home and 22.5 acres with long views. The Adirondack style main residence is constructed to the highest standard, by one of Woodstock's premier builders. A well conceived floor plan presents both generously sized common gathering areas as well as quieter private spaces. Family members, of multiple generations, are comfortably accommodated. Large bedroom suites, on 2 levels, can provide adult guests with privacy. All the expected amenities! On the lower level is the truly extraordinary private bar/entertainment area, a large 40x12 exercise room, a hot tub room, with shower, and a workshop, with space for all the motorized toys! The detached 9 room, 3 bedroom guest house is private and substantial. A beloved family compound! well sited, on 20 acres of land, at the end of a private lane, with long views of distant mountains.

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