Mountain town living in Winhall between Bennington County ski resorts
Winhall is a southwestern Vermont town that ranges among the Green Mountains, and the resort-style reasons that seasonal and year-round residents call it home coat slopes that surround it in every direction. “If you move to Winhall, you have Bromley, Stratton and Magic Mountain ski resorts making a sort of triangle around you. It’s a mountain town. That gives it a different way of life, where things are associated with recreation on the mountains from the winter through the summer,” says Kristin Comeau, a sales associate at TPW Real Estate Sales who specializes in Bennington County and lives in Winhall. A love for rural traditions and outdoor recreation creeps into all facets of life in Winhall, from the programming at local private schools to the agricultural awards given out at Vermont’s longest-running annual fair.
Nearby alpine skiing, national forest recreation and community arts
Alpine skiers have their pick of Green Mountain range slopes; Bromley Mountain and Stratton Mountain ski resorts are to the town’s immediate north and south, while Magic Mountain Ski Area is just a little farther away to the northeast. A 27-hole course also draws golfers to Stratton Mountain, along with other amenities like a mountain bike park and tennis courts. The region is rich with opportunities for less structured recreation, from hiking the ridgeline-spanning Long Trail, to pitching a tent at multiple campsites scattered around the Green Mountain National Forest to casting into streams and ponds like the ones in the Gale Meadows Wildlife Management Area. In the small village section of town called, the Winhall Community Arts Center is a gallery space for local artists and a venue for weekly art and exercise classes run by volunteers.
Single-family homes on rural lots and condos near Stratton Mountain
Set in forested foothills, Winhall’s single-family homes range from classic A-frame chalets to luxury New Traditional construction to simple cabins hiding back on country roads. That diversity of styles means that homes set on small acreages and suburban-sized lots can sell for around $400,000 to more than $2.5 million. Homes hidden on much larger lots can go for $1.3 million to $6.5 million depending on whether they’re closer to 20 acres or more than 100 in size. Condos can sell for $285,000 to over $2 million depending on their size, luxury amenities and proximity to Stratton Mountain Ski Resort. Although some residents have chosen to move to Winhall full-time thanks to the rise of remote work, many homes are still primarily occupied during ski season or on vacation weekends. “Winhall instituted some short-term rental ordinances recently. Not to say that you can’t do it, but if you’re purchasing to make an Airbnb, it’s important to check that out,” Comeau says. Waterways like the Winhall River give many properties waterfront views in addition to Green Mountain vistas. Buyers can consult maps to understand their potential flood risk and need for insurance.
Shopping and dining in Bondville
Though commercial life is somewhat limited in Winhall, a handful of specialty businesses collect along State Route 30 in Bondville. The Winhall Market supplies groceries and prepared deli foods across the street from the post office and a 7-Eleven. Down the road, diners pick up sandwiches from Workhorse Cafe. The town's surrounding ski resorts have on-site restaurants and retailers of their own. More independent and outlet shops line a walkable stretch of State Route 7A in Manchester, the northshire county seat that's a roughly 10-minute drive from Winhall.
Historic fun at the modern Bondville Fair
The annual three-day Bondville Fair harkens back to a time when Winhall’s mountain settlements were dominated by farmland rather than winter sports destinations. “The town of Winhall was incorporated in 1796. The first Bondville Fair was held the following year,” Comeau says. “It’s morphed a lot, but it still holds some of those old county fair kinds of traditions – quilt making, a floral hall, produce judging kinds of things.” Thousands return each year to the state’s oldest fair, ready for carnival rides, fair foods and livestock pulls. The fairgrounds also host a series of free concerts and farmers market throughout the summer.
Attending independent schools in and around Winhall
Winhall is not served by any public schools. Families can choose from multiple independent schools in the region and receive full or partial tuition coverage through the state’s school choice system. For kindergarten through sixth grade, students can attend The Mountain School at Winhall, an independent school that is not currently rated by Niche. Stratton Mountain School serves seventh through 12th grades and earns an A-plus from Niche and is known for an exceptional winter sports program that has turned dozens of student athletes into Olympians.
Traveling between cities and regional hubs on State Route 30
Those that use Winhall as a seasonal home have an upward of three-hour drive to places like Boston and New York City. Regional travelers take State Route 30 more than 35 miles to Brattleboro Memorial Hospital or head the opposite direction to find State Route 7, a major connector between Bennington County’s two shire towns. While most residents rely on a personal vehicle to get around, cow-printed MOOver! buses do run free, limited regional routes through the winter. Albany International Airport is about 70 miles away.
Mud season and maple sugaring in Winhall
All of Vermont is familiar with the transition from a snow-covered winter into a snowmelt-fueled mud season. Many miles of dirt roads make the town of Winhall susceptible to springtime slowdowns that go beyond shuttered hiking trails. “The dirt roads are very well-maintained, but mud season can wreak havoc on some of them. The school bus might not run on certain roads for a while because they’re so heavy, and the town wants to avoid towing them,” Comeau says. She also notes that mud season and maple sugaring season tend to overlap, so there’s at least some time-intensive sap boiling to get up to when mud makes it hard to get around.
Written By
Julia Szymanski
