Hartland, VT | 184 Hartland Hill Road

Currently operating as an award winning B&B, this thoughtfully designed, flexibly configured income property is also ideal as a primary residence. Situated at 45 Pleasant Street, just a short stroll from the shops, restaurants and galleries of Woodstock Village, the property overlooks East End Park and the Ottauquechee River Trail, offering an exceptional blend of village convenience as well as natural beauty and outdoor recreation. Inside, historic Vermont charm meets sophisticated contemporary design, with rich finishes, warm hardwood floors, dramatic tilework, custom built-ins and thoughtfully designed lighting throughout. Beautifully appointed baths feature contemporary tile, glass-enclosed showers and upscale finishes reminiscent of a luxury boutique hotel. Guest accommodations offer comfort and privacy, with each principal guest room featuring a king bed, private bath and wet bar equipped with refrigerator, microwave and coffee maker. The expansive 420-square-foot suite includes a separate living room and spa-inspired bath with double vanity, heated floors, heated towel rack and jetted tub. Inviting common areas, a guest lounge, wraparound porch, decks, gardens and fire-pit areas create wonderful spaces for entertaining or relaxation. A dedicated yoga/Pilates studio offers additional flexibility for wellness activities or personal enjoyment. The private upper-level owner's quarters feature two bedrooms, two beautifully appointed baths, a full eat-in kitchen and finished attic space, providing exceptional flexibility for an owner/operator, extended family or full-time residence. Enjoy Woodstock's four-season lifestyle, from skiing and snowshoeing to hiking, golf, cycling and exploring Vermont's scenic countryside. Whether envisioned as a private residence, hospitality venture or investment property, this distinctive offering combines an established rental platform, exceptional location and versatile living spaces. A rare opportunity to make it your own!

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.

15 Central Street is one of the finest commercial locations in Woodstock with two of the most creative and successful businesses as the anchor tenants. The historic building has adapted to changes over the course of its long history of uses including residential, barber shop, a dance & pool hall, law office, architectural services and a variety of mercantile endeavors. Notably, the building was the headquarters of Lt Colonel Peter T. Washburn, who led the 1st Vermont Regiment troops in their crucial role at Gettysburg. He returned to the roles of Adjutant and Inspector General to organize and direct Vermont’s military efforts through the rest of the Civil War from his offices at 15 Central Street. The current owners, recognizing it was time to adapt the building to the 21st Century, developed plans to upgrade and modernize the second and third floors for mixed use including an incredible residential unit with exposed brick walls and timber framing. The story high historic windows have been restored, and the second level has been reframed with new sheetrock. The third level partition walls have been removed to create a dramatic open area with views over the village to the north and south leaving the finishes and uses of the two levels up to your imagination. This is a once-in-a-lifetime opportunity to acquire a property with a remarkable history and become part of creating Woodstock’s future. Note: Gross income reduced in 2024 due to renovation