Rupert, VT Classified Ad Listings

712 VT Route 30. Nestled in a picturesque Dorset, Vermont setting, this classic 1850 farmhouse offers an affordable opportunity to create the home of your dreams. Situated on a manageable quarter-acre lot, the property features a detached two-car garage, two additional outbuildings, screened in porch, enclosed three season porch and established perennial plantings with classic New England chara...

3269 Route 30. Historic District, Dorset Village 4 Bedroom Colonial Farmhouse located with both residential and commercial zoning walk to every village amenity such as the Dorset Inn, Barrows House and Pool, Dorset Bakery, The Union Store, The Field Club, Dorset Library, Theater, Historic Society, and the Pinnacle walking trail. Recently restored this residence lives comfortably with extensive ...

809 Gorhamtown Rd. Welcome to 809 Gorhamtown Road, where historic charm and modern updates meet on a peaceful 1.1-acre lot just outside the village of Poultney. The spacious three bedroom, 2 bath home offers 2,228 square feet, including a 1-bedroom accessory apartment, ideal for multigenerational living, guest space or rental income. The main house has a recently renovated first floor with ensu...

84 Frost Pond Rd. **Privacy. Design. Nature. Possibility.** Tucked away on 12.3 acres, this exceptional contemporary retreat is the kind of property that makes you slow down the moment you arrive. A peaceful pond, mature woodlands, and complete privacy create an extraordinary setting, while the home's thoughtful architecture brings the beauty of the outdoors into every room. Wrapped in beautifu...

1060 Upper Hollow Rd. 'MOONLIGHT REFLECTIONS ON AN UPPER HOLLOW SANCTUARY'... This stunning rare estate sits on 66 secluded acres of unspoiled beauty, offering breathtaking sweeping views of two luminous ponds, where moonlight reflections shimmer across the water each evening, creating a truly magical feeling. Inside you will find a contemporary open layout anchored by a dramatic stone fireplac...

73 South St. Discover an outstanding opportunity in the heart of the vibrant and picturesque community of Middletown Springs. This versatile 0.30-acre commercial lot offers incredible potential for a variety of uses-whether you're looking to establish a business, create a mixed-use space, or develop your own vision from the ground up. Conveniently located with electricity at the street, this pr...

Fox Ln Lot 3. The last lot located in a quaint Dorset cul de sac. One of the few building lots left in the most coveted Dorset village, abutting national forest on the marsh. This lot is the only available lot in Dorset Village. Home Owners Association, organized and fully functional by the residents of Fox Lane. Take a walk, create a bench from a fallen tree, in the 18 acre common forested lan...

543 Lower Hollow Rd. A Serene Dorset Hollow Retreat Along the Mettowee River Tucked into the storied Dorset Hollow, this 4.6-acre retreat enjoys 488 feet of Mettowee River frontage, offering a rare blend of tranquility, comfort, and timeless Vermont charm. Expansive mountain views and the soothing sounds of the river surround you-fall asleep each night to its calming presence. Multiple outdoor ...

38 North College Street. Single Family Home for sale in Poultney, VT for $249,000 with 3 bedrooms and 2 full baths. This 2,245 square foot home was built in 1850 on a lot size of 0.23.. Historic Village Home with Timeless Charm & Endless Potential! Step back in time and discover the character and charm of this classic 1800s village home! Ideally located near local amenities, shopping, and nearb...

131 School St #1R. This is a NO SMOKING, NO PET property.Newly constructed one bedroom ground-level luxury apartment now available for occupancy in Manchester's historic downtown core. The open concept apartment is located on School Street, less than a block from shopping, restaurants, pharmacy, bank and library.The 1,200 square foot apartment features finely appointed kitchen, bath and living ...

100 New St. Welcome to 100 New Street, a beautifully updated, move-in-ready home sitting on a generously-sized lot in the heart of the village of West Pawlet. Originally built in 1900, this charming residence blends classic character with modern upgrades. First floor laundry in the mudroom is convenient, and the open floor plan is light and airy. There are three bedrooms, including one on the f...

43 North St. Set at the highest point of the property, Higher Ground looks south across open fields and a gently rolling valley toward distant Vermont mountains. Originally constructed as a barn in the 1840s, the post-and-beam structure was moved from the lowest point of the property to its highest and reimagined by the current owners. Original timber framing and authentic barn elements remain ...

40 Kelleher Rd. Where Vermont Living Feels Effortless Dorset Home, Guest Cottage, Pond and Mountain Views Settle into the beauty of Dorset with a property that feels like a true Vermont retreat. This lovingly maintained offering pairs a welcoming main residence with a separate one-bedroom cottage, 4.5 acres of open land, a private pond, and beautiful views creating a rare opportunity to enjoy s...

397 Fern Hl. Take a drive up Nichols Hill Road to Fern Hill and head to the very top of the long bending driveway to find a serene, picturesque artist's retreat 3 minutes from historic Dorset Village. Refreshingly private, quiet and secluded, drenched in natural light. With broad mountain vistas of Mother Myrick and Merck Forest, the top of the property backs gently into a beautiful private for...

3039 Route 30. Tucked away at the end of a long, winding driveway, this remarkable Dorset Village estate sits on one of the area's largest parcels-over six private acres. A rare blend of privacy, history, and elegance, the home features four stunning stone fireplaces, exposed antique beams, reclaimed wood details, and abundant natural light throughout its flowing layout. Designed for gathering ...

42 Mountain Rd. Nestled alongside a quiet town gravel road on almost 7 acres, this newly built two plus (loft/bedroom and permitted as a 4 bedroom) bedroom, one bath timber frame home is perfect to hang your hat and enjoy nature, peace and quiet. Ideally designed with a full length back porch looking west over the meadow and beautiful wetland area set down below the meadow - Could be perfect fo...

31 Amerio Rd. Step into the cozy cottage core farmhouse you've been dreaming of! Nestled on the outskirts of Poultney, just over the Castleton line, this charming 1840s farmhouse offers the perfect blend of timeless character, thoughtful updates, and country living on approximately 3 beautiful acres. The heart of the home is the sun-filled kitchen, where oversized windows flood the space with n...

61 Norton Ave. Welcome to this charming village home tucked away on a quiet side street in Poultney, offering the perfect blend of convenience, comfort, and inviting indoor and outdoor living! Within walking distance to Poultney Elementary School and the nearby Rail Trail, you'll enjoy easy access to walking, biking, and snowmobiling while still appreciating the peaceful setting and minimal tra...

27 Owls Head Hill Ln. Charming Raised Ranch on 2 Acres - Dorset, VT Welcome to your new home in the heart of Dorset! Nestled on a beautifully landscaped 2-acre corner lot, this inviting raised ranch offers privacy, comfort, and versatile living space. 3 Bedrooms | 2 Full Baths | 2-Car Attached Garage Step inside to find a bright living room that flows seamlessly into the eat-in kitchen, perfect...

321 Bentley Ave. Welcome to this income-producing gem! Located in the heart of Poultney and within walking distance to schools, shopping, and public transportation, this charming 3-unit property presents a fantastic opportunity for both investors and owner-occupants alike. Each unit is bright, inviting, and full of character. The front unit features a classic covered porch, two bedrooms, and a ...