West Windsor, VT Homes for Sale with Acreage

Experience Vermont living at its finest in this custom-built home, thoughtfully designed by the builder for exceptional energy efficiency and year-round comfort. Perfect as a relaxing getaway, this property offers expansive sleeping spaces ideal for hosting family and friends. Spend your days exploring the nearby VAST Trail system or Ascutney Mountain, and your evenings unwinding by the

Katie Ladue Gilbert BHHS Verani Upper Valley

Wonderful unfinished 24'x34' pole building, a rare opportunity to shape a home or getaway that fits your lifestyle perfectly on 9.4 tranquil acres on W Rowe Hill Rd. On VAST trail, great trail location for year round recreation. Close to GMHA & Ascutney Outdoors, ride your horse, bike or sled right from your door! A short drive to Okemo or Killington. Easy access to I91 and the Upper Valley.

Dana Waters Dark Horse Realty

Farm at Gaelic Crossing is an equestrian property set on 26.72± acres, has dramatic views of Mount Ascutney and, after summer showers, the frequent and magical appearance of rainbows—often even double rainbows—across the wide, open sky. This updated c.1842 New England Cape offers 2,554 square feet of finished living space, including four bedrooms—two conveniently located on the first floor. Wide

Story Jenks LandVest, Inc/Woodstock

They say land remembers. On Rush Meadow Road—where rolling fields meet the quiet rhythm of the seasons—there is a place that has been held, cared for, and passed down for over a century. This 103-acre estate is not something that was assembled. It was lived. Worked. Protected. For generations, it operated as a dairy farm, and the land still reflects that stewardship—lush hayfields, a ready-to-tap

Katie Ladue Gilbert BHHS Verani Upper Valley

Set against sweeping views of Mount Ascutney, this distinctive property offers the kind of Vermont escape buyers rarely find—private, spacious, and designed for gathering. Thoughtfully expanded over time, the home seamlessly blends two living spaces, creating an ideal setting for hosting extended family and friends while still offering comfort and privacy for all.The newer portion of the home

Gary Coger Four Seasons Sotheby's Int'l Realty

This is a MUST SEE to appreciate! Breathtaking Views of Mt. Ascutney & the Valley Beyond!Welcome to this stunning custom-built 4-bedroom, 3-bath home where every window frames a masterpiece. Sweeping, panoramic views of majestic Mt. Ascutney and the rolling hillsides create an awe-inspiring backdrop you'll never tire of — whether sipping morning coffee or watching the sunset paint the peaks

Katie Ladue Gilbert BHHS Verani Upper Valley

Constructed in 2025, and located in the desirable Rush Meadow region of West Windsor, this impeccably orchestrated Yankee Barn Post and Beam home features superb materials, old world craftsmanship and detailed fit and finish. Custom milled cabinetry and built-ins throughout. The rooms are filled with natural light with stunning bucolic views from every window. The home is centered by a dramatic

Danny Kogut Williamson Group Sothebys Intl. Realty

Adorable partially furnished 3 bedroom, 2 bath home on landscaped 1.53 acres corner lot in the heart of Ascutney Mt Resort! Many upgrades including Bosch High Efficiency Propane Boiler, Mitsubishi heat pump/AC, Rinnai on demand hot water heater, new well tank & centrifuge filtration system, new fireplace & chimney with Woodstock soapstone woodstove flanked by custom cabinets on each side. Decks,

Dana Waters Dark Horse Realty

Nice location in West Windsor, with a partially renovated 3BR 2 Bath manufactured home on 10.47a with 3 stall barn with hayloft, tack room, water & electricity; older fencing remains. Home has mudroom entry, utility room, & corrugated metal roof. It's been completely rewired, insulated, 3 Mitsubishi mini-splits, soapstone woodstove, GE kitchen appliances, some new windows & flooring. There will

Dana Waters Dark Horse Realty

Stately hilltop home built by Silas Banister c.1800, recently undergone a complete restoration. Quality materials & craftsmanship throughout. It has gorgeous views of nearby Ascutney Mountain & long-range views of NH. The property consists of 98 acres made up of fields, hard & softwoods, trails, a large sugarbush (potential for a future boiling operation). Conserved by Upper Valley Land Trust,

Dana Waters Dark Horse Realty