Just 2 miles from Woodstock Village, this gracious brick cape on 6 open acres offers space, comfort, and classic Vermont charm. The expanded chef’s kitchen opens to a gracious gathering room ideal for entertaining, while 3 fireplaces—wood-burning, brick, and gas-ready—provide cozy warmth throughout. Upstairs, find 3–4 bedrooms including one with its own fireplace, plus a private guest room or

Keri Cole Williamson Group Sothebys Intl. Realty

The Richmond House – Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a distinguished brick Federal with a softly weathered, rose-hued patina and elegant architectural details. Set on over an acre behind a classic white picket fence, this historic property—reimagined under the direction of Laurence Rockefeller—comprises three luxurious residences

Zoe Hathorn Washburn Snyder Donegan Real Estate Group

Just minutes from the heart of Woodstock, this 3-bedroom, 3-bath home with a dedicated office/family room has been transformed from the ground up into a modern, energy-efficient retreat. Taken down to the studs, the renovation was comprehensive—every system replaced, with all new wiring, plumbing, insulation, and mechanicals, along with a new roof, Pella windows, central heating, and air

Keri Cole Williamson Group Sothebys Intl. Realty

An exquisite, private retreat for artists, writers, nature-lovers, composers or simply as a quiet, serene getaway gathering house on 66 stunningly beautiful acres with stone walls, gardens, patios, open lawns, a beautiful swimming pond, in-ground heated saltwater pool with stone patio, and a breathtakingly beautiful outdoor screened pergola. The residence was constructed using reclaimed frames

John Snyder Snyder Donegan Real Estate Group

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

Chris Lang

Set along the banks of Lakota Brook and framed by Vermont countryside, 31 Lakota Road is a storybook farmhouse reimagined for today. This 3-bedroom, 2-bath ranch offers single-level ease with every detail complete. Fashioned around a circa 1800’s schoolhouse, the home showcases vaulted ceilings, exposed hand-hewn beams, and a stone fireplace anchoring the living room. Sunlight pours through

Daniel Preston KW Vermont Woodstock

A rare opportunity to own a piece of Vermont history - The North Pomfret Store & Post Office, c.1830. This 3-story New Englander offers charm, character, and a solid income stream on 3.25 picturesque acres. With 5 total units, the property includes 3 residential apartments (one 2-bedroom, one 1-bedroom, and an Efficiency), a ground-floor commercial office space, and the historic U.S. Post Office

John Bassette Bassette Real Estate Group

Great location to both historic Woodstock and the Upper Valley. This charming cape has lots of antique characteristics with original wood floors and accented with hand hewn beams. The second floor was expanded with taller ceiling height, new windows and insulation. Kitchen flows to a large dining room with half bath and laundry on first floor. Large sunlit living room off the North end of the

Gretchjen Smith Williamson Group Sothebys Intl. Realty

Charming, Unique, and Ideally Located! Welcome to 100 Pomfret Road—a beautifully updated farmhouse set on four level, picturesque acres just a short walk from Mt. Tom, Billings Farm, and the heart of downtown Woodstock. This rare find blends timeless character with everyday convenience in a peaceful, brookside setting.Inside, you’ll find a sun-drenched home featuring four

Keri Cole Williamson Group Sothebys Intl. Realty

"LONG WAY HILL" - An elegant and beautifully constructed residence of the highest quality, privately situated on 54 acres with long-range views, lawns, gardens, fields and trails. Beautiful perennial and wildflower gardens offer charming, private views of woods and hills over a half-acre pond. Architect-designed in the style of a traditional New England country home, the main residence has 5

John Snyder Snyder Donegan Real Estate Group

NEW PRICE!! Discover classic Vermont charm at The Harry Emmons House, an antique brick cape located in the village of Taftsville, ideally situated on a level, open lot. A traditional covered farm porch leads to a gathering room with a brick fireplace. The main level features bright, airy living spaces with high ceilings and exposed beams, comfortable rooms, a country kitchen, a sunny dining room,

Scott Monahan Williamson Group Sothebys Intl. Realty

Airy, tranquil and quiet, this former yoga studio space has been converted into a two bedroom condo. Sweeping views through the Palladian window, large living area with soaring vaulted ceiling, newer kitchen with granite counters and newer bath with walk in shower. Spacious entry can accommodate bikes, skis and more. Walking distance to shops, restaurants, entertainment and recreation in the

Jane Darrach Martha E. Diebold/Hanover

Discover the possibilities with this beautifully crafted three bedroom, three and one half bath home and versatile Post and Beam barn/studio, set between Woodstock and Silver Lake in scenic Barnard. The main residence features an airy great room with vaulted ceilings, warm wood accents, and expansive windows that invite natural light and frame peaceful views. Thoughtful design and quality

Eric Johnston Four Seasons Sotheby's Int'l Realty

Erika Smith RE/MAX Upper Valley