Imagine waking to the quiet rhythm of the Vermont countryside, where morning light stretches across open meadows, woodland trails begin just beyond your door, and the pace of life slows to match the landscape. Set on 26 acres in Rupert, this exceptional property offers a rare combination of privacy, craftsmanship, and room to pursue the life you've imagined. The home is designed to feel connected to its surroundings, with warm wood finishes, expansive windows, and comfortable living spaces that invite both gathering and relaxation. Throughout the property, extraordinary stonework, all from the quarry on-site, reflects a level of artistry and care rarely found today. Beyond the home, a fully equipped 3,100-square-foot heated garage and workshop creates endless possibilities. Featuring radiant heat, a commercial-grade car lift, office space, bathroom, heat pumps, central vacuum, air lines, and oversized 12' x 12' doors, it is an ideal setting for automotive enthusiasts, collectors, entrepreneurs, craftspeople, or anyone seeking exceptional workspace. The land itself is a destination. Explore private trails through mature woods, enjoy open fields, snowshoe after a fresh snowfall, or take advantage of the nearby D&H Rail Trail. Every season brings new opportunities to experience the beauty of Vermont. Additional storage buildings provide ample space for equipment, recreational gear, and the practical needs of country living. Both the home and workshop benefit from updated high-efficiency heating systems for year-round comfort. Conveniently located within easy reach of Manchester, Dorset, regional ski areas, and the Adirondacks, this property offers the perfect balance of seclusion and accessibility. Whether you're seeking a full-time residence, a weekend retreat, a live-work property, or a place to gather family and friends for years to come, this Rupert estate offers a lifestyle defined by space, creativity, and connection to the land. Schedule your private tour today.
Beautiful country farmhouse with meadow views. Come see this 3 bedroom one bath home on half an acre surrounded by country views and meadows. Built in 1865 this Vermont homestead has a wonderful sunny garden area and attached one car garage. The main level has everything you need; a generous first floor bedroom and large bathroom, spacious living and dining areas and eat in kitchen with newer appliances. Oversized bonus room with separate enterance perfect for a home office or workshop. The second floor features two additional bedrooms and space enough for a second bathroom. Don't miss the famous Sugar Shed and Come make this well maintained property your home. General Store, post office and the rail trail are all close by. Only 15 minutes to Dorset Green and 10 minuted to Salem NY for all your shopping needs. Priced to sell! Grades 7-12 School Choice! Call today! Don't let this affordable option get away.
Luxury move in ready fully renovated 1909 Federal home on 5+ peaceful acres, protected mountain views and stream frontage, but just 5 minutes from the activities on the Dorset Green and the Dorset Field Club. A 3 year renovation by the areas most skilled workmen includes a custom walnut kitchen with high end appliances, island bar seating opening to dining room for entertainment and family life. New hickory floors and walnut railings throughout accentuate this light filled home. The new custom stone fireplace and chimney in the living room opens to a spacious private covered porch. The first floor primary bedroom incudes a bathroom with spa like vibe and includes spectacular views to wake up to. Upstairs has 3 bedrooms, including a second primary suite with bathroom, walk in closet and 2 additional bedrooms with bathroom and a bonus television or recreation room. Outdoor space includes an elegant custom stone deck that is perfect for quiet morning coffee, drinks or evening dinners. A fully renovated living cottage with cathedral ceilings provides privacy with its own driveway and address which could be flex space for guests, office or studio, or as a rental. Add a Airstream trailer for additional quiet space down by the stream. Both homes have new or newer septic systems; with every aspect improved including new siding; roofs; IPE decks, Marvin windows, propane tanks, and Generac generators for many years of worry free living. Landscaping improvements are still underway! Back up offers accepted.
Rupert is located in Vermont. Rupert, Vermont has a population of 685. Rupert is more family-centric than the surrounding county with 26.87% of the households containing married families with children. The county average for households married with children is 22.94%.
The median household income in Rupert, Vermont is $61,471. The median household income for the surrounding county is $63,448 compared to the national median of $69,021. The median age of people living in Rupert is 50.4 years.
The average high temperature in July is 78.8 degrees, with an average low temperature in January of 8.4 degrees. The average rainfall is approximately 48.2 inches per year, with 93.7 inches of snow per year.
