Rupert, VT Classified Ad Listings

2664 US Route 7 S. Welcome home to this spacious four bedroom, two bathroom property set on 2.26 acres in Wallingford, Vermont. With nearly 2,000 square feet of living space, this 1800's home is full of character and offers an inviting open floor plan suited to both everyday living and entertaining. The acreage provides room to garden, play, gather outdoors, or simply enjoy the peaceful Vermont...

866 E Manchester Rd. BROOK FRONTAGE AND MOUNTAIN VIEWS If you are looking for a property with both mountain and water views, this exceptional five-bedroom Manchester home is must-see. Set on a remarkable lot featuring breathtaking vistas and approximately 400 feet of frontage along Bromley Brook, this home offers a rare combination of privacy, natural beauty, and convenience. Located just minut...

84 Overlook Rd. Commanding panoramic mountain views define this exceptional Dorset Overlook residence, where every room is designed to capture the beauty of Southern Vermont's ever-changing landscape. Bathed in natural light, the home's open floor plan creates an effortless flow between living, dining, and entertaining spaces, making everyday living as enjoyable as hosting family and friends. T...

1625 Barnumville Rd. Offered for the first time in almost 40 years, this charming farmhouse is set on a picturesque 1.7 acre parcel of open land in Manchester, Vermont. Ideally located directly across from East of Equinox horse farm, the property offers a country setting just minutes from town. The main level features tall ceilings, a spacious kitchen with an adjoining dining area, and a genero...

120 Summit Vw. Experience an exceptional combination of commanding Southern Vermont mountain views, refined luxury and extraordinary energy efficiency at this custom modern farmhouse just outside Manchester Village. Designed by Alan Benoit of Sustainable Design and built in 2017 by Gutbier and Albin of Red Mountain Builders, this beautifully proportioned 5 bedroom, 5 bath residence offers priva...

59 East St. This beautiful 1810, meticulously maintained, village home and 4 car barn have been lovingly restored from top to bottom and inside to out by the current talented owners. And yes, the heat pump is considered a heating system and has heated this home year-round. Air conditioning in the summer and heat source in the winter with the Harmon pellet stove for additional heat. The open kit...

96 Prospect St. Nestled in the quintessential village of Wallingford, Vermont, this charming three bedroom, one bathroom home is ready to welcome its new owners. Warm, inviting, and full of character, you'll appreciate the beautiful hardwood floors, classic wood trim, and cozy atmosphere throughout. The charming kitchen features a center island, creating the perfect space for meal preparation, ...

253 Perkins Rd. INTERIOR PHOTOS NOW ADDED. Tucked away on a quiet, town-maintained dead-end dirt road, this inviting Rupert, Vermont property offers the kind of peaceful country setting that's becoming increasingly hard to find. Set on 6.79+/- acres, it's a place where morning walks, afternoon bike rides, and evenings under the stars can become part of everyday life. At the heart of the propert...

39 Sage Hill Rd Unit 25. WINTER SEASONAL RENTAL: 12/1/26 to 3/31/2027 Location is everything, and Torbank's condominiums are the perfect choice! Just minutes from the heart of Manchester, Southern Vermont's premier destination, you'll have easy access to boutique shopping, dining, medical services, and year-round activities. In the winter, enjoy the convenience of nearby skiing at Bromley Mount...

168 Stones Throw Lane. Single Family Home for sale in Manchester, VT for $374,000 with 3 bedrooms and 1 full bath. This 931 square foot home was built in 1910 on a lot size of 2.3.. Set on 2.30 acres, this charming 1910 home offers a welcome sense of privacy in Manchester Village. Inside, hardwood floors, detailed woodwork, divided-light windows, built-in bookcases, and a wood-burning fireplace...

1174 N Main St. Set on 13.6 picturesque acres with sweeping mountain views and gently rolling fields, this beautifully updated farmhouse captures the essence of Vermont living. Offering 4 bedrooms and 3 bathrooms, the home seamlessly blends timeless character with modern updates, including a renovated kitchen and bathrooms, new flooring, fresh interior paint, a new boiler, water softener, a wea...

1310 Dorset Hill Rd. Perched on the side of Mount Aeolus and conveniently located near Manchester, this exceptional 4-bedroom, 3-bath contemporary retreat offers privacy, sophistication, and year-round natural beauty across 21 picturesque acres. Thoughtfully designed to embrace its surroundings, the property features rolling meadows, mature woodland, vibrant perennial gardens, and sweeping view...

69 Applewood Ln. Open concept 4 bedroom, 2 bath home in convenient location in Manchester Center. Nice stone fireplace, granite countertops, stainless appliances. Fresh paint throughout. Large covered deck and nice flat lawn, perfect for enjoying those beautiful Vermont days. Empty raised garden beds available, if you'd like to grow some veggies, along with perennial flower gardens. Partially f...

484 W Lake Rd. Nestled beside the tranquil waters of Lake St. Catherine, this year round lake home is move in ready and provides effortless single level living. Stepping through the back entry from the detached two car garage, you'll know immediately this is your dream home with views of paradise. Boasting Brazilian cherry flooring throughout, The Great Room, combining the kitchen, living room ...

203 Meader Road. Single Family Home for sale in Greenwich, NY for $299,000 with 1 bedroom and 2 full baths. This 900 square foot home was built in 2023 on a lot size of 2.35.. This one catches the eye and there's just as much to love once you step inside! Set on 2.35 acres in the Town of Greenwich, this custom home pairs fantastic curb appeal with an inviting open floor plan. Neat as a pin and ...

706 High Chapparal Rd. Set up off a publicly maintained gravel road, this lovingly cared for Cape offers beautiful western-facing mountain views and breathtaking sunsets, with a charming setting that feels like home from the moment you arrive. Step through the inviting front entry and you'll immediately appreciate the warmth and character this home has to offer. Beautiful oak floors run through...

446 Highland Ave. Looking for a unique opportunity for equity growth? This is it! Location, location, location. Highly desirable Highland Avenue is one of those rare streets with character homes that is literally only a few walking blocks to town. If you are lucky enough to own this charming 3- bedroom home offering 1,663 sq ft of living space, you will enjoy easy access to the library, local s...

26 W Broadway. Single Family Home for sale in Salem, NY for $249,900 with 4 bedrooms and 2 full baths. This 2,458 square foot home was built in 1878 on a lot size of 0.46.. Available for the first time in decades, this beautiful 1878 home offers over 2,400 square feet of living space filled with character and possibilities. Featuring 4 bedrooms, 2 full bathrooms, a formal dining room, a den, an...

2456 Vermont Route 30. Tucked away at the end of a privately maintained road, lined with a stonewall on each side, provides a beautiful entrance to this 2.70 acre parcel with a most private and peaceful setting that feels like a dream the moment you arrive. The beautiful yard continues with the stonewall boundary, mountain views and a luscious grassy yard. A perfect home for pets, gardeners, ch...

655 Squirrel Hollow Rd. This contemporary residence by acclaimed architect Jeff Barnes offers a versatile floor plan with abundant living options, set on 23 private acres that balance tranquility with equal proximity to Manchester Center and Dorset Village. A quick trip to Bromley Mountain and Stratton, the home is set amidst professional landscaping with sweeping Green Mountain views. The main...