Listings by Dia Jenks

The John Arnold Cottle House is a landmark residence in the heart of South Woodstock, a rare blend of village convenience and country living. Built in 1811 by one of the area's earliest settlers, this stately Federal-style brick home has been thoughtfully restored to honor its historic charm while integrating modern comforts. Set on 2.7 acres, the property features 450 feet of frontage on Kedron Brook, along with a firepit, a barn, and a river meadow. The barn—currently used for storage—could easily be converted to accommodate a couple of horses or sheep. The three-bedroom main house has elegant 12-over-12 windows, high ceilings, and beautifully preserved period details, including a second-floor ballroom with a coved ceiling and fiddler’s stage—a nod to its past as a lively gathering space. The newer addition overlooking the brook has a magnificent great room with 17' cathedral ceilings and a gourmet kitchen and wood burning brick fireplace. The renovated Kingsley Barn guest house offers two bedrooms, a loft, and a deck overlooking the brook. Below there is a heated workshop, ideal for puttering, creating, and getting lost in a project. A timber bridge spans the waterway, connecting the property’s field, barn and trails. With direct access to the Upwey Trail system and equestrian paths leading to the Green Mountain Horse Association, this property is ideal for outdoor enthusiasts. Located along South Road in the South Woodstock Historic District, the home is part of a landscape of preserved 19th-century architecture and pastoral beauty.

Chase Brook Farm is at the end of a quiet country road, offering complete privacy on 52+/- acres and yet just 10 miles from Okemo Ski Resort, fine dining, and shopping. The views are punctuated by bucolic vistas of the Green Mountains including Steadman Hill, the highest peak in Chester. At the center of this property is a 2,941 sq. ft. farmhouse, built in 2008 and inspired by countless visits to Sturbridge Village. Thoughtfully designed to evoke the charm of a historic home, it features hand-planed boards, painted wide pine floors, wrought iron latches, and soapstone countertops—while providing the comfort of modern amenities, including new mechanicals, updated wiring, and a large, dry basement. This property invites year-round enjoyment. In winter, sled down hills out back, or clear the pond for skating parties. Snowmobilers, skiers, and snowshoers will appreciate the room to roam and easy access to the VAST trail for extended adventures. After a day in the snow, warm up by one of the two cozy fireplaces or take a soak in the hot tub out on the deck. In summer, enjoy a swim or cast a line in the stocked pond, or gather berries from the 80+ blueberry bushes and raspberry patch. The fall season brings apple picking, perfect for homemade pies and sauces. The land is also suitable for livestock, offering versatility for a variety of uses. Chase Brook weaves in and out along the border to the East. Additional features include an attached one-bay garage for the main house, a three-bedroom caretaker’s house with a three-bay garage, and fiber optic internet. 19 min from Weston Playhouse; 40 min from Killington and Bromley; 57 min from Vermont Summer Festival (equestrian event in Dorset); 2h 15m from Hartford; 2h 45m from Boston.

In the 1940s, the farm became home to Camp William James, a base for the Civilian Conservation Corps (CCC). Inspired by William James' essay The Moral Equivalent of War, the camp brought together in winter Dartmouth and Harvard students for apprenticeships with local farm youth, promoting national service in peacetime. This ethos later influenced the creation of the Peace Corps in 1961. It is said that Eleanor Roosevelt visited the camp one winter and famously used the two-holer outhouse in the backyard. Tunbridge is the home of the Tunbridge World's Fair and The Ranger, a gravel bike ride. 39 minutes from Dartmouth College, and less than 2.5 hours from Boston.