Newfane, VT | 66 Upper Oak Hill Road

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