West Windsor VT Homes $0 to $30000000
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Viewing 1 to 7 of 7 listings
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Price Change! reduced by $146,000 down 29% on September 1st 2026
Listed Thursday Jul 9, 2026
$499,000 | $234 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 2515 | Acres: 10.27 WEST WINDSOR VT
View Details & 35 images
Description:Quietly sited off a private secluded road, sits a finely hand-crafted family home and outbuildings on 10.27 acres. The lot features an open yard, gardens, stone walls, woodland trails & nearby brooks. The main house features post and beam construction with sweeping cathedral ceilings, 2 bedrooms, 1.5 baths, a loft, finished lower level, and many custom-built features. The kitchen is well appointed with custom cabinetry and stone counters. A stand-out bonus feature comprises a detached 2 bedroom in-law or rental apartment above an 1150 sq. foot office/woodworking shop prefect for hobbies or a commercial home business. This property is perfectly sited in close proximity to State Forest for hiking, biking trails on Mt Ascutney, easy access to Interstate 91, Woodstock VT, Hanover NH, Dartmouth, and all recreation.
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Price Change! reduced by $50,000 down 7% on August 20th 2026
Listed Wednesday Jul 29, 2026
$699,500 | $331 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 2112 | Acres: 5.01 WEST WINDSOR VT
View Details & 37 images
Description:Welcome to The Rock House! A beautiful hillside retreat set on a private, lush landscape with captivating views of Mount Ascutney. The home's spectacular great room is the heart of the property, featuring soaring cathedral ceilings, rich hardwood floors, a dramatic floor to ceiling stone fireplace, and walls of windows that flood the space with natural light while showcasing the breathtaking mountain vistas. Thoughtfully designed for both comfortable everyday living and effortless entertaining, this inviting gathering space perfectly captures the warmth, character, and natural beauty that make the Rock House so special. The beautifully updated kitchen features quartz countertops, quality cabinetry, and an efficient layout that makes meal preparation both functional and enjoyable. The spacious main-level primary suite offers a peaceful retreat, complete with an attached sunroom featuring radiant floor heat, an ideal spot to relax year-round while taking in the surrounding landscape. Two additional bedrooms and a three-quarter bath complete the main level, providing comfortable accommodations for family and guests. Privately tucked away on the upper level, an additional ensuite bedroom offers flexibility as a guest suite, home office, or secluded retreat. The exterior is landscaped with two stone patios and level lawn area with fire pit seating area perfect for relaxing and entertaining. Modern comforts and energy efficiency abound with mini-splits, new furnace, solar array, tesla battery, and heated two car garage. Combining timeless architectural appeal with thoughtful updates and an exceptional setting, The Rock House offers a rare opportunity to enjoy Vermont living at its finest.Take in multi-seasonal recreation and the arts just minutes away at Ascutney Outdoors and Brownsville Butcher & Pantry for some terrific local dining. Easy access to Woodstock, Killington and Okemo. Showings to begin at the
- Under Contract
Listed Tuesday Jul 7, 2026
$775,000 | $245 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 3168 | Acres: 2.5 WEST WINDSOR VT
View Details & 42 images
Description:Located in the heart of Sheddsville-West Windsor's earliest settlement, this lovingly stewarded historic Greek Revival Farmhouse imbues the true character of the Vermont vernacular. Improved over the centuries to accommodate modern living, all while preserving the the period detail and charm with original pine plank floors, 6/6 sash windows and hewn beams. The home was well built of solid and sound plank construction, providing insulation throughout. The beautiful Great Room addition is anchored by a handsome wood burning fireplace with custom cherry mantel, and connects to the exterior spaces through French doors stepping out to a covered porch and a spacious deck overlooking a sweeping level lawn, mature maple trees, established perennial beds, and a firepit at the edge of a four-season stream. Open concept eat in kitchen with farmer sink and butcher block counters, formal dining room, library- TV room, study with a half bathroom. Two mudrooms complete the main level. Moving upstairs, there's a generous primary bedroom ensuite with a wood stove, a laundry room, three additional bedrooms and a shared bathroom. Leased Tesla back up battery provides peace of mind in the event of a power outage. The ample three-bay barn can be used as parking, equipment storage, workshop, or for farm animals. Extensive dirt road, and trail systems (ideal for equine interests, hiking, cycling) are just out side your door. Easy access to all recreation, Interstate, Woodstock, Hanover NH. 2.25 Hours to Boston. 4.5 hours to NYC. Showings begin with an Open House on Saturday July 11 from 11:00 to 12:30
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Price Change! reduced by $50,000 down 4% on August 6th 2026
Listed Wednesday Jun 3, 2026
$1,295,000 | $255 per sq.ft. | 7 Beds | 6 Baths | Total Sq. Ft. 5774 | Acres: 5.51 VILLAGE OF BROWNSVILLE IN TOWN OF WEST WINDSOR VT
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Description:With sweeping views of Mount Ascutney, this exceptional home offers the Vermont lifestyle so many buyers dream of. A place where family and friends gather, traditions begin, and every season brings new adventures. Thoughtfully expanded over time, it blends two living spaces into one inviting home, offering generous room to be together while providing comfort and privacy for everyone. The newer addition features an open concept kitchen, dining, and living area anchored by a custom stone fireplace and dramatic floor to ceiling windows framing the mountain views. A sun-filled deck invites morning coffee, summer entertaining, or cozy après ski evenings. The primary suite is a private retreat with its own deck, ensuite bath, walk in closet, and dedicated office. The original wing offers four additional bedrooms, a kitchen, living area, and its own deck, creating an ideal space for guests or extended family. Whether enjoyed as one expansive residence, configured for private guest accommodations, or explored for its income-producing rental potential, the flexible layout adapts to a variety of lifestyles. Located in the heart of Brownsville. Just minutes from Mount Ascutney's trails and outdoor recreation, and within easy reach of Woodstock, Okemo, Killington, and the Upper Valley, this is a rare opportunity to own a true Vermont retreat where unforgettable memories are made all year long, with the added flexibility of potential rental income when you're away.
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Listed Wednesday Apr 29, 2026
$1,325,000 | $519 per sq.ft. | 4 Beds | 2 Baths | Total Sq. Ft. 2554 | Acres: 26.72 WEST WINDSOR VT
View Details & 46 images
Description: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 pine and maple floors run throughout, adding classic farmhouse character. The equestrian amenities are outstanding: a 3,024-square-foot stable with seven spacious stalls, a heated tack room, wash stall, bathroom, and laundry area. The 100' x 200' riding arena features a state-of-the-art, eco-friendly footing made from recycled sneakers, offering outstanding drainage, low dust, and excellent footing. Outdoor facilities also included are a round pen, four grass paddocks, and one dirt paddock. Quiet gravel roads invite walking and riding, with access to the Green Mountain Horse Association trail system. A stream winds along the property's West border, while apple and pear trees provide seasonal bounty. High-speed internet ensures fast connectivity. Ascutney Outdoors, with 40 miles of trails for horseback riding, mountain biking, skiing, and hiking, is nearby, and the popular Brownsville Butcher and Pantry is less than two miles away. (Horses not included)
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Price Change! reduced by $200,000 down 6% on August 12th 2026
Listed Wednesday Apr 15, 2026
$3,150,000 | $981 per sq.ft. | 5 Beds | 5 Baths | Total Sq. Ft. 3212 | Acres: 98 WEST WINDSOR VT
View Details & 60 images
Description: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, enrolled in Current Use. The main floor offers a new kitchen which boasts a beautiful 11' quartzite island & counters. Dining & Family Room with soapstone woodstove, Living Room with a new Rumford Fireplace with rod iron & glass doors for efficiency. A large Sunroom with slate floor, more than an entry it's a nice transitional space to enjoy, 3 BR/3 BA and a Sitting area on the 2nd floor with a tranquil view of the back fields. 2 additional BRs and a half bath on the 3rd floor. All new wiring, plumbing, new Bosch propane furnace supplies radiant heat, triple pane, Anderson low-E4 windows, sheetrock, DaVinci slate-like rubber roof & cherry floors. Fully insulated, extremely efficient. Custom built trim, wide baseboards, wainscoting & cabinets. 200+ year old pine boards from the house were used to craft bathroom vanities, 3rd floor stairs & beautiful doors. Outdoor amenities include in ground pool, gardens & lovely stone patio. A large-3600 sq ft former dairy barn with new wiring & FHA furnace & oil tank. Now used as a garage, workshop & abundant storage space offers ENDLESS possibilities!
- New Listing!
Listed Friday Sep 4, 2026
$3,975,000 | $906 per sq.ft. | 4 Beds | 7 Baths | Total Sq. Ft. 6450 | Acres: 21.52 WEST WINDSOR VT
View Details & 55 images
Description:Sheep Run Farm takes its name from the stone-walled lanes where a prosperous 19th-century farmer once moved his sheep between the barn and upper meadows. Nearly two centuries later, those walls still trace the landscape, framing a beautifully reimagined Vermont farmstead on 21± acres in West Windsor, 3 miles from South Woodstock and 8 miles from Woodstock Village. Drawing on the traditional forms of Vermont architecture, the 2017 residence introduces a lighter, more contemporary way of living, with large windows and an open main level overlooking the Rush Meadow Valley and Mount Ascutney. A series of connected buildings includes a two-bay garage, carriage barn, wood room, yoga studio, and private guest suite. The three-season carriage barn is an exceptional gathering space, with a massive stone fireplace and an oversized glass door opening to a stone terrace, pergola and gardens. The land unfolds through rolling meadows, orchards, extensive stone walls, a cascading brook, and two ponds, including a swimming pond with a small beach. Additional buildings include a heated detached garage, equipment barn, and run-in shed at the top of the meadow. Located near GMHA, an extensive network of equestrian trails, and quiet country roads well suited to gravel riding, Sheep Run Farm combines the character of an established Vermont farmstead with the ease and systems of a modern country home. High-speed EC Fiber supports integrated lighting, climate, security, video, and property-access controls. Showings start September 11th.
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Data last updated September 11th, 2026
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