Woodstock, VT | 2033 South Road

New price! Discover the possibilities at Wise Pines, an extraordinary 40± acre property in the heart of Hartland, Vermont, ideally located between Woodstock and Quechee. Surrounded by rolling hills, mature forests, and tranquil walking trails, this unique property was thoughtfully created as a sustainable wellness retreat and offers an exceptional opportunity for its next owner. Wise Pines began its journey hosting Appalachian Trail hikers but has quickly evolved into a destination for outdoor enthusiasts of all types. Truly unique accommodations for up to 16 guests, including two extraordinary tree houses, a bunk house with two private rooms and an eight bed bunk room in the second story. The new lodge building has a full kitchen, a lounge, laundry and a large 2nd story open yoga/recreation space. Whether your vision includes a retreat center, boutique inn, vacation rental business, educational campus, event venue, or private estate, the infrastructure is already in place to support a wide range of possibilities. The property benefits from an existing Act 250 permit and a septic system designed to accommodate occupancy of the primary residence and up to 16 guests, adding tremendous value for a host of potential uses. Enjoy easy access to skiing, hiking, golf, dining, shopping, and all the outdoor recreation that the Upper Valley is known for. A truly one-of-a-kind Vermont property where natural beauty, privacy, and opportunity come together. Please join us for an open house Saturday, July 11, 2026 from 1 to 5 pm.

Historic character, beautifully reimagined for modern Vermont living. Minutes from Woodstock Village, this extensively renovated four-bedroom home pairs the warmth and authenticity of its 150-year-old wide-pine floors and exposed beams with a remarkable collection of recent improvements. At the heart of the home is a brand-new, high-end kitchen with Bosch appliances and newly installed natural bluestone radiant heat flooring, complemented by thoughtfully updated baths, including one with a beautifully executed marble walk-in shower. A dramatic new three-story addition, wrapped in oversized casement windows, introduces abundant natural light and generous new living space while creating a compelling architectural counterpoint to the original home. Nearly every major element has been addressed: new ultra-durable Everlast Advanced Composite siding, interior paint, new roof, all new windows, heat and AC pumps throughout, and a whole-house generator provide the comfort, efficiency, and peace of mind of a thoroughly updated property. Outside, the setting is quintessential Vermont. A new natural bluestone patio and walkway open to an expansive, level lawn bordered by the Kedron Valley Brook, where natural swimming holes invite summer afternoons by the water. Established landscaping, a pond, firepit, and the sound of the brook create an unexpectedly private retreat remarkably close to town. The property also features a historic 2,100-square-foot classic red barn with approved septic plans, offering incredible potential for unique expansion. Just minutes from Woodstock Village, with excellent proximity to the Mt. Peg trail system, Woodstock Inn & Resort amenities, and GMHA, this is a rare opportunity to enjoy the soul and craftsmanship of an historic Vermont home with the ease, light, and livability of a comprehensive modern renovation. Old Vermont soul. Entirely new chapter. Showings begin Saturday, 9/19/2026, with an open house from 1-3:30.

Dual residential hilltop with a river view and commercial property located on US Route 4 in Vermont - the scenic east-west crossroad carrying travelers from the New York border, across the Green Mountains, to the Connecticut River at the New Hampshire border. The property boasts a 1.5 story Cape (3 bedrooms, large first floor office/sitting room, or B & B room with quaint clawfoot tub private bath); upstairs office, and more! Built in the 1850's, the residence has 2,334 sq ft. A successful farmers market for many years, the property has greenhouse capabilities, two large barns, a farmer’s garage, milkhouse, dairy milking parlor, and a shed for ducks next to the pond, as well as additional farmstand space. Close proximity to the Killington Ski Area - with highway frontage between Quechee and Woodstock - and minutes from Dartmouth College in Hanover, NH; the intersection of I-89 and 91 at the Connecticut River; as well as Northern New England’s major DH Medical complex and Cancer Center in Lebanon, NH, and the VA Hospital in White River Junction. Professional design plans for a Vermont-style Inn and restaurant could be available with a Buyer Agreement. On the hilltop above Route 4, with a great view of a bend in the Ottauquechee River, this truly is a ‘must see’ home and business opportunity.