Newfane, VT | 66 Upper Oak Hill Road

Steeped in Vermont history and surrounded by more than 80 acres of fields, woods, and walking trails, this beautifully preserved Newfane farmhouse offers the rare opportunity to own a property where timeless character and modern comfort come together. Whether you're looking for a full-time residence, country retreat, or recreational property, this is a place to slow down and enjoy the beauty of every season. The home features 3 bedrooms, 2 bathrooms, wide plank wood floors, exposed hand-hewn beams, and thoughtfully updated living spaces that remain true to the home's historic roots. The renovated kitchen offers granite countertops, custom cabinetry, stainless steel appliances, and a spacious center island that naturally becomes the gathering place for family and friends. Three original working fireplaces create warmth and character throughout the home. One of the home's most remarkable features is its fully functional beehive oven, a rare piece of early New England craftsmanship that continues to be used today. Traditionally heated by a wood fire, these domed brick ovens retain their heat long after the embers are removed, making them ideal for baking and slow roasting. The current owners still enjoy using the oven to bake fresh homemade breads, pies, and even batches of granola as the oven gently cools, carrying on a tradition that has been part of Vermont farmhouses for generations. It is a truly special feature that connects the home's rich history with everyday living. Outside, the property is equally inviting. Wander through the simple perennial gardens, tend to the established vegetable gardens, relax beside the small pond, or explore the extensive acreage that offers exceptional privacy and endless opportunities for hiking, snowshoeing, wildlife watching, hunting, maple sugaring, or simply enjoying the peaceful Vermont landscape. Located just minutes from the historic village of Newfane, with easy access to Brattleboro, Mount Snow, and Stratton Mountain.

180° +/- views, end of the road, top of the hill privacy. 12 acres,4 beds,2 baths,brick,beams,built-ins,custom features,screen room, bonus space! A combination increasingly difficult to find, especially minutes from Newfane Village, Rock River, Brattleboro, vibrant arts community, farm-to-table dining, local galleries, garden shops, farm markets, outdoor recreation that define this special corner of Southern Vermont. Tucked away,this 4 bed, 2 bath Gambrel-style home offers the kind of privacy that has become a luxury in its own right w/wooded & open land, rock gardens, panoramic mountain views,room to explore, relax, or simply enjoy the peace & quiet. With more clearing, the already impressive views offer the opportunity to become even more expansive. Whether you're looking for a full-time Vermont home, weekend retreat, place to work remotely while surrounded by nature, this property offers remarkable flexibility. Enjoy your morning coffee overlooking the mountains, spend the afternoon exploring your land, or gather w/friends in the screened gazebo while watching the sunset. Inside, beams,window seat, custom built-ins & a striking brick accent wall create inviting spaces filled w/warmth & character. Spacious kitchen open to dining room, formal and mudroom entries, full laundry, easily accessible mechanicals. Four bedrooms PLUS multiple flexible bonus spaces provide exceptional versatility for a home office, studio, library, fitness room, guest overflow. Whole-house generator, Wi-Fi & reliable cell service provide modern convenience, while additional utility buildings offer abundant storage, workshop space & room for outdoor gear, equipment or hobbies. Private yet close enough to everything that makes Newfane one of Southern Vermont's most beloved villages. Spend the afternoon at the Rock River, explore galleries, garden shops, linger over farm-to-table dining, hike, or enjoy a night out in Brattleboro before returning home to the rare luxury of complete privacy.

Beautiful Cape style home nestled in a private country setting, surrounded by mature trees in desirable Newfane and just a short drive to skiing, hiking and other outdoor recreation. Offering exceptional flexibility, the property features an in-law apartment in addition to a separate living quarter, both are currently generating rental income, ideal for multigenerational living, extended family, guests, or supplemental income. A charming she shed/VIP lounge with electricity provides the perfect home office, studio, or creative workspace. The main part of the home is spacious, offering an open-concept kitchen with stainless steel appliances, a center island, a stunning fireplace and direct access to the back deck. The first floor also features a formal dining room, a comfortable living room, and a cozy den with a second fireplace. Upstairs, you'll find several generously sized bedrooms and bathrooms, providing plenty of room for family and guests. Additional outbuildings include an attached garage currently used to store equipment and wood along with two detached buildings which offer ample storage or workshop space. Designed with entertaining in mind, the expansive back deck features a custom-built outdoor fireplace, creating the perfect setting for gatherings throughout the seasons. With its spacious layout, multiple living areas, income potential, and peaceful country setting, this exceptional property offers endless possibilities. Showings begin 7/27/2026

This is your chance to be part of the historic and lively community in the center of Newfane. This home underwent a complete overhaul in the early 2000s, including a new slate roof, a relocated fireplace for a more practical layout, a reinforced stone foundation with a poured concrete floor, new windows, boiler, cement clapboard, and new kitchen countertops. The main level features radiant heating, an open-concept living and dining area, a modern kitchen, and the primary bedroom with an ensuite full bath. It also includes a large bonus room with its own egress, perfect for a mudroom, office, studio, or playroom. The second floor offers two additional bedrooms, a unique bathroom, and a large attic space with great potential to be finished. Outside, the yard boasts beautiful stonework and plenty of flat, green space for gardening or activities. The property is also within walking distance to the country store, bank, restaurants, and yoga studios. You can rest easy knowing all the heavy lifting has already been done!