$702,269Average Value$405Average Price per Sq Ft6Homes For Sale
Woods and farmland around Mount Ascutney in West Windsor, Vermont
West Windsor is a Vermont township located about 9 miles from the New Hampshire border and the Connecticut River. The largely rural and wooded area surrounds the village of Brownsville, near the base of Mount Ascutney, the tallest mountain in Windsor County. A strong community and outdoorsy spirit pervades, shown in the local Brownsville Butcher & Pantry, a volunteer-run ski area on the mountain and a 100-mile annual race. “It almost feels like we live in another time,” says Danny Kogut, associate broker with Williamson Group Sotheby’s International Realty, with over a decade and a half of experience. “It’s an enormous relief to come back here after being away.” Nearby towns such as Woodstock and Windsor have essentials and a variety of shopping and dining, with more just over the New Hampshire border. “West Lebanon and Claremont, New Hampshire, have the box stores and supermarkets,” Kogut says. “But these Vermont towns are well-suited to meeting people’s needs.”
West Windsor is mainly a rural area where residents value their privacy.
West Windsor kayakers have a tranquil paddle along the Connecticut River.
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Ranch-style homes and sweeping, secluded estates
Many properties can cost between $250,000 and $380,000, while large and elegant homes with sweeping mountain views or ample acreage can cost up to $1.7 million. The median price for a single-family home in West Windsor is about $610,000, higher than the national median. The small population and ample space mean many homes are well-spaced along state highways or small roads, some on broad fields of open farmland, others tucked among tall trees. Farm properties frequently have outbuildings, and many yards are expansive swaths of green. The density increases in Brownsville; residents there can even see their neighbors' houses. Half-stories and ramblers are common styles in the village. The area holds a CAP Index Crime Score of 1 out of 10, lower than the national average of 4.
The lots get larger as you move away from downtown West Windsor.
Country homes in West Windsor sit on expansive lots.
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Mount Ascutney offers a volunteer-run ski area and many hiking spots
Mount Ascutney provides much of the recreation in the area. “The anchor of the town was Ascutney Mountain Resort, which had been privately held by out-of-state investors,” Kogut says. “But the town got together, and with grants and donations, a group of local residents spearheaded the revival of the area.” Now the mountain has a volunteer-run ski area, Ascutney Outdoors, which has also partnered with the town to create programs and maintain facilities in West Windsor Town Forest. Additionally, the mountain is home to hiking trails and an eponymous state park, which can be accessed near Windsor. Residents can hike the mountain’s Summit Loop Trail, the Bicentennial Trail, Lower Quarry and the Weathersfield Trail, among others. “There’s a huge network of trails,” Kogut says. “Some go through private land, which shows something about how people think here.” Hikers are welcome to cross the private land, so long as they do so responsibly.
West Windsor bikers get air at Ascutney Trails Andrew Goulet Skills Park.
Lose yourself in thought as you wander the trails of West Windsor Town Forest.
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Outdoor races, a summer music festival and a holiday sale
The area’s outdoorsy culture shows in its annual events. “West Windsor hosts the Vermont 100, a hundred-mile race,” Kogut says. The town also hosts the Flow State Mountain Bike Festival at Ascutney Outdoors. West Windsor Music Festival takes place in the summer at Story Memorial Hall. Ascutney Outdoors puts on an annual holiday sale and solstice celebration.
Albert Bridge and Windsor Schools serve the community
Albert Bridge School in Brownsville is quite small, with under 100 students, and serves grades pre-kindergarten through sixth. It earns a B-minus from Niche. Students then move to Windsor School for grades seven through 12, which earns a C-plus. Windsor seniors complete a capstone research project and show their work at an exhibition that is open to the public.
Students of West Windsor begin their educational journey at Albert Bridge School.
West Windsor students are eager to learn as soon as they enter the doors at the Windsor School.
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Brownsville Butcher & Pantry and additional choices in Windsor
West Windsor’s community has rallied around Brownsville Butcher & Pantry. “Brownsville Butcher & Pantry used to be the general store,” Kogut says. “Like many places, it fell on hard times in 2008. Locals bought it and leased it to a young couple who created a destination. It’s really become the heart of the town in some ways.” In addition to produce, seafood and local beef, residents can enjoy breakfast, sandwiches and dinner entrees at the attached café. The Maple Kitchen serves upscale dinner fare in the Holiday Inn Mount Ascutney Resort. There is a Price Chopper supermarket in Windsor, about 6 miles east. Windsor is also home to additional shopping and dining, including Windsor Station Restaurant & Bar, which serves American cuisine in a former train depot.
Brownsville Butcher & Pantry is a convenient one-stop shop for all the shopping needs of West Windsor residents.
The residents of West Windsor make a quick trip to Windsor for more shopping options.
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State highways, nearby towns and Amtrak in Windsor
Main roads in West Windsor include Vermont Route 44, which runs from Windsor through Brownsville before intersecting with Vermont Route 106, which runs north to Woodstock, about 15 miles away, and south to Springfield, about 18 miles away. Both towns offer additional amenities and shops. Mount Ascutney Hospital and Health Center in Windsor is about 6 miles away. Amtrak’s Vermonter train stops daily in Windsor, and Interstate 91 and U.S. Route 5 also run near Windsor, though the interstate is only accessible near the towns of Hartland and Ascutney. The Burlington International Airport is about 105 miles away.
Written By
Ty Phelps
Photography Contributed By
Shawn Miller
Video By
Maurice Boone
Interested in learning more about homes in this area?
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On average, homes in West Windsor, VT sell after 40 days on the market compared to the national average of 58 days. The median sale price for homes in West Windsor, VT over the last 12 months is $535,000, up 34% from the median home sale price over the previous 12 months.
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
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
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.
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
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
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
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
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
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,
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
This inviting condo offers the perfect blend of comfort, convenience, and year-round outdoor access. Step right outside your back door to enjoy scenic hiking and biking trails, while world-class skiing and snowboarding are just moments away. This unique home features two separate floors, ideal for flexible living. The first floor offers its own private entrance, along with dedicated bedrooms and
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,
Newly renovated, 1-Bedroom, 1-Bath Apartment located on a secluded cul-de-sac near Hartland Four Corners, very convenient to Rte 91. Sunny entry room features large slider doors that lead out into garden area with views of Mt. Ascutney. Spacious Living Room, Galley Kitchen with Stainless-Steel refrigerator and electric stove, Large Bathroom with new vanity and extra-large Storage/Pantry. Brand
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