19 properties for sale in West Rupert

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

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, entre

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 property is a circa 1850 Greek Revival home, rich with architectural character and topped by a classic slate roof. A substantial steel barn offers exceptional space for hobbies, equipment, vehicles, a workshop, or the projects you've always wanted room to pursue. Significant improvements have already been completed, including a new septic system, ductless mini-split heating and cooling, all new windows and exterior doors, a whole-house water filtration and softener system, an updated bathroom and a generator hookup. These investments provide a solid foundation while leaving room for the next owner to add their own visi

Charming Vermont Chalet on 3 Pastoral Acres Backing Up to Merck Forest! Embrace the ultimate Vermont lifestyle with this versatile 1970s chalet on +/-3 pristine acres of open pasture and woods. Located on a quiet country road bordering the 3,000+ acre Merck Forest and Farmland Center, this property offers incredible privacy and direct outdoor access. Perfectly suited as a year-round home, ski getaway, or mini-farm, it features some recent updates, including a propane furnace and electric hot water heater (both under 10 years old). The home does need some TLC, including new windows and a new sliding glass door, providing a great opportunity to build equity. Property Highlights: 3-Level Chalet Layout: Ground Floor: Mudroom/utility entry, open-concept kitchen and dining family room area with patio access, and a full bath. Main (2nd) Level: Light-filled living room with cathedral ceilings, wood stove, and deck access. Primary suite including a 3/4 bath plus a flexible space for an office o

Charming Vermont Chalet on 3 Pastoral Acres Backing Up to Merck Forest! Embrace the ultimate Vermont lifestyle with this versatile 1970s chalet on +/-3 pristine acres of open pasture and woods. Located on a quiet country road bordering the 3,000+ acre Merck Forest and Farmland Center, this property offers incredible privacy and direct outdoor access. Perfectly suited as a year-round home, ski getaway, or mini-farm, it features some recent updates, including a propane furnace and electric hot water heater (both under 10 years old). The home does need some TLC, including new windows and a new sliding glass door, providing a great opportunity to build equity. Property Highlights: 3-Level Chalet Layout: Ground Floor: Mudroom/utility entry, open-concept kitchen and dining family room area with patio access, and a full bath. Main (2nd) Level: Light-filled living room with cathedral ceilings, wood stove, and deck access. Primary suite including a 3/4 bath plus a flexible space for an office o

Turnkey, income-producing mixed-use investment opportunity with current gross rental income of $4,200 per month and potential for future income growth. The property has undergone extensive renovations, making this an attractive addition to any investment portfolio. The commercial space is currently leased to Matelli's Taverna, providing established rental income. Upstairs are two spacious, well-maintained apartments-one 2-bedroom unit and one 3-bedroom unit-offering additional residential income. With a strong mix of commercial and residential tenants already in place, this property offers immediate cash flow, multiple income streams, and room to increase returns. An excellent opportunity for investors seeking a renovated, established mixed-use property

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 property is a circa 1850 Greek Revival home, rich with architectural character and topped by a classic slate roof. A substantial steel barn offers exceptional space for hobbies, equipment, vehicles, a workshop, or the projects you've always wanted room to pursue. Significant improvements have already been completed, including a new septic system, ductless mini-split heating and cooling, all new windows and exterior doors, a whole-house water filtration and softener system, an updated bathroom and a generator hookup. These investments provide a solid foundation while leaving room for the next owner to add their own visi

Charming Vermont Chalet on 3 Pastoral Acres Backing Up to Merck Forest! Embrace the ultimate Vermont lifestyle with this versatile 1970s chalet on +/-3 pristine acres of open pasture and woods. Located on a quiet country road bordering the 3,000+ acre Merck Forest and Farmland Center, this property offers incredible privacy and direct outdoor access. Perfectly suited as a year-round home, ski getaway, or mini-farm, it features some recent updates, including a propane furnace and electric hot water heater (both under 10 years old). The home does need some TLC, including new windows and a new sliding glass door, providing a great opportunity to build equity. Property Highlights: 3-Level Chalet Layout: Ground Floor: Mudroom/utility entry, open-concept kitchen and dining family room area with patio access, and a full bath. Main (2nd) Level: Light-filled living room with cathedral ceilings, wood stove, and deck access. Primary suite including a 3/4 bath plus a flexible space for an office o

Home features 2 bedrooms, 1 bath, large kitchen, and open concept living/dining area. Located on a quiet street one block from Main St. Sold as-is

Nestled on a quiet side street in Salem, this 3-bedroom home offers an inviting place to call your own. Fresh interior paint, hardwood floors, a cute three-season room, and built in shelving in the living room add to the home's charm and character. While its convenient location keeps you close to local amenities, shops, schools and everything Salem has to offer. Whether you're looking for your first home, downsizing, or simply want the convenience of village living, this one is well worth a look! 40 minutes to Saratoga Springs & the ADK Region, 30 minutes to Manchester, VT

Welcome home to this spacious, inviting 4-bedroom, 2-bath home with 1,920 square feet of living space, classic architectural details, and thoughtful updates throughout. Freshly painted with new luxury vinyl plank flooring and beautiful hardwood floors, this home is full of warmth and character. A generous entryway welcomes you into a bright, sun-filled living room featuring low-profile coffered ceilings and decorative columns that create a charming transition into the dining room. The spacious eat-in kitchen offers plenty of room to gather, with built-in cabinetry, a walk-in pantry, and a large window overlooking the yard. A convenient mudroom and first-floor laundry add everyday practicality. Four generously sized bedrooms offer comfortable living, with details including walk-in closets, decorative ceilings, and ceiling fans. Two full bathrooms feature tilework, built-in storage, and a walk-in shower with a glass door. Outside, enjoy a fully fenced yard with gated access, attractive l

This 439 acre property includes trails, extensive road frontage, includes several water features that include frontage on the West Beaver Brook, the Black Creek, a few different small tributary streams, and frontage on a large pond. Though mostly wooded the property does have a couple of small meadows. There is a stately 1830's colonial that is currently just a shell and is waiting to be restored to its full potential. The home has been recently vinyl sided, features replacement windows, includes a combination of blown-in and spray foam insulation, and offers a newer roof. The majority of the acreage (356.9 acres) is enrolled in the 480 Fisher Forestry Program

Off-Grid Retreat on the Vermont Border. Escape to your own private woodland retreat on 5.22 secluded acres, with the eastern property line marking the Vermont state border. Well-built and lovingly maintained, this charming off-grid cabin offers the perfect blend of comfort, self-sufficiency, and outdoor recreation. The cozy cabin features a dining area, kitchenette with propane range, spacious living room with woodstove, sleeping loft, and a wonderful side porch for relaxing and enjoying the peaceful surroundings. Solar panels provide lighting and basic electrical needs, while propane lights and generator wiring offer dependable backup. A spacious storage shed houses the solar batteries and provides plenty of room for equipment and supplies. Listen to the sounds of the cascading creek across the road, explore your wooded acreage, and enjoy excellent opportunities for hiking, hunting, and homesteading. Whether you're seeking a weekend getaway or a quiet place to unplug and reconnect wit

Tucked away on a privately maintained lane, this secluded off-grid cabin offers the perfect setting for self-reliant living on 5.39 wooded acres. Pride of ownership shines throughout this well-constructed and meticulously maintained 1 bedroom, 1.5 bath retreat. The first floor features gleaming wood floors, a cozy open floor plan, well-appointed kitchen, woodstove, shiplap paneled walls, laundry area, and full bathroom. Upstairs, the spacious bedroom offers vaulted ceilings and a half bath. Rustic charm and thoughtful comforts blend seamlessly throughout. Relax on the rocking chair front porch overlooking the manicured lawn and perennial gardens, while a seasonal stream and pond add to the property's natural beauty. A surrounding hardwood forest provides outstanding privacy along with a steady source of firewood. The home is equipped with a 200 amp electrical panel powered by either a whole-house generator or photovoltaic battery bank, with optional propane lighting as an additional fe

Tucked away along the quiet dirt roads of Hebron, this extraordinary 506-acre property offers the kind of privacy, beauty and versatility that is increasingly difficult to find. Open tillable fields blend with extensive woodlands, a pond, apple trees and sweeping views across the Washington County countryside & Vermont Green Mountains and beyond At the heart of the property is a spacious 5-bedroom home offering plenty of room to gather, with a game room, dedicated office, updated kitchen and updated mechanicals. A second home, currently used as a rental, adds another layer of flexibility-whether for income, extended family, guests or a caretaker. The land itself is what makes this offering truly special. Farm the fields, explore the woods, hunt, hike, enjoy the pond and wildlife, or simply appreciate having an incredible amount of space and seclusion around you. The mix of open and wooded acreage also creates possibilities for agricultural, recreational, investment or family-compound u

Welcome to 234 S Grimes Rd in Hebron-a true country escape where serenity, peace, and quiet surround you at every turn. Set on 3.49 acres of gorgeous countryside, this remarkable country estate retreat offers breathtaking views for miles stretching toward the Green Mountains, creating a setting that feels like your own private sanctuary. Inside, you'll find an updated kitchen designed for both everyday living and entertaining, a formal dining room perfect for gathering with family and friends, and a spacious living room anchored by a cozy wood-burning fireplace-ideal for relaxing on crisp country evenings. With seven bedrooms, there is plenty of space for extended family, guests, or the flexibility to create home offices, hobby rooms, or private retreats. Step outside to the covered side porch overlooking the beautiful slate patio, where you can unwind, entertain, or simply take in the stunning natural surroundings & abundant wildlife. Offering privacy, endless beauty, and room to brea

Tucked away amid the rolling hills of Hebron, this enchanting two-bedroom cottage retreat offers an exceptional opportunity to embrace the beauty and tranquility of Washington County. Set on more than 16 picturesque acres, the property is a haven of privacy where sweeping countryside views, open meadows, and peaceful natural surroundings create an extraordinary escape from everyday life. Thoughtfully designed with an open floor plan, the home is warm and inviting, featuring efficient mini-split heating and cooling, a cozy wood stove, and effortless indoor-outdoor living with a spacious front deck perfectly positioned to take in the breathtaking vistas. A detached insulated two-car garage provides year-round convenience, while the small barn with chicken coop, pond, and expansive acreage make this a true homesteader's dream. Whether you envision hobby farming, gardening, keeping animals, or simply enjoying the abundant wildlife and serene landscape, the possibilities are endless. Perfec

Motivated Sellers. Offers encouraged! Warm and inviting lakefront retreat on tranquil Scott Lake! Nestled along the shores of a pristine 30-acre spring-fed lake in scenic Washington County, this charming Lakehouse offers the perfect escape for relaxation and recreation. Enjoy swimming, fishing, boating, and peaceful days on the water from your own private lake frontage with dock and lakeside deck. Filled with rustic charm, the home features a cozy great room with pellet stove and propane heater, a well-equipped kitchen, and a dining room with beautiful waterfront views. The spacious layout includes a primary bedroom with a full bath and private access to the rear deck, plus three additional bedrooms, a loft, and a second full bathroom, providing ample space for family and guests. Offered mostly furnished, and comes with a small fishing boat with a trolling motor a paddleboat and kayaks, this delightful lake home is ready for immediate enjoyment. The property extends to both sides of th

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Consider Stebbins Bardwell's Legacy: A rare opportunity to own a storied 300-acre Vermont farm rooted in American agricultural history. Established in 1863 as Vermont's first cheesemaking co-op by Consider Stebbins Bardwell, this remarkable property has been thoughtfully revived for modern use. From 2004-2020 the current owners revived and reinvented the farm's cheesemaking tradition, producing award-winning artisan cowandgoat cheeses recognized by major nationalandinternational publications and competitions. This cheese making facility continues to operate and is currently leased out for additional monthly income. This is more than a historic farm, it's a lifestyle property with extraordinary versatility and income potential. Continue the celebrated cheesemaking operation with a fully equipped, FDA-inspected facility and five custom aging caves, or reimagine the infrastructure for grass-fed beef, dry-aged steaks, organic hay production, or a farm-to-table event venue for weddings and

This 4 unit multi family property located in Manchester's Depot district has been owned and managed by the same partnership group for almost 40 years. The property is fully occupied with good tenants and is in excellent condition. There are two apartments on the first floor and two apartments on the second floor. There is ample off street parking behind the building. Each apartment has its own energy efficient propane heater. Backup electric baseboard heat is also available. Each apartment has it's own electric hot water tank which is on the tenant's electric service. Each apartment is separately metered and has a separate service panel. Almost all the windows are energy efficient replacements. The in town location provides tenants with easy access to all the amenities that Manchester has to offer. The listing agent is related to one of the owners of the property

Welcome home to this spectacular, multi-level property in Bromley Village, a private slopeside community in Peru. Conveniently located just a short walk to/from Bromley Mountain's ski slopes, the Village Clubhouse, and across from the Village pond. A well designed layout which features 5 Bedrooms (including two En-suites), a total of 5 Bathrooms, multiple spacious Living areas, and a fabulous 2-story Deck with outdoor shower. This property is the ultimate vacation or year-round residence with no detail overlooked. A Fabulous, grand Main Living area with high ceilings features a wood-burning Fireplace in the Living room which is open to the large Dining room w/ sitting area, wet bar and sliders to the expansive, 2-level Deck with lovely mountain views. The chef's Kitchen has professional appliances (Thermador gas cooktop and dual ovens, Sub-Zero refrigerator, and Bosch dishwasher), custom cabinetry, and gorgeous soapstone counters. The two En-suites are located off the main living area,

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 space, privacy, and flexibility in one memorable setting. The main home welcomes you with a light-filled sunroom, a wonderful place to relax and enjoy the surrounding scenery. The renovated eat in kitchen with a fireplace features beautiful, leathered granite countertops, stainless steel appliances while the spacious living room offers a propane stove, creating a warm and inviting atmosphere on cozy Vermont winter evenings. A comfortable den on the first floor provides additional living or office space. Upstairs, the home features three charming bedrooms and two additional bathrooms, offering plenty of room for f

Nestled in one of Vermont's most coveted villages, this three-bedroom, two-bathroom home is a canvas waiting for your creative vision. Priced well below assessed value, this property represents a rare opportunity to build equity from day one while enjoying the charm of quintessential New England living. The generous lot gives you room to breathe, garden, or simply watch the seasons paint the Green Mountains in ever-changing color. A massive barn stands ready for transformation - imagine your dream workshop, art studio, or even a small business headquarters tucked into this idyllic setting. The property also includes an accessory dwelling unit, offering flexible options for guests, rental income, or additional living space that makes financial sense. The barn and ADU ready for your touches all cleaned out and ready for your toys and guests. The home itself invites renovation-minded buyers to roll up their sleeves and craft something truly special. Whether you envision a modern farmhouse

Village Mixed Use zoned Residence and Separate cottage located in the Hamlett of South Dorset. nearby Dorset's elementary School and Sheldon's Market. Conveniently located 3 miles from Manchester Ctr to the South or Dorset Village to the North. The main house offers 1350 SF, 2 bedrooms with overflow room, large closet, and sunroom entrance. The cottage is 675 SF with one bedroom and a great-room with 3/4 bath. The Hot Air furnace is a couple years old. there's also a wood stove. The Cottage is heated by propane. The cook's kitchens in both residences enjoy open great-room style living and have all appliances including gas ranges, refrigerators and dishwashers. there's laundry as well in both dwellings. See the Dorset Village Mixed Use zoning documents attached allowing retail, hospitality, home office services. etc. Please also note Dorset Short Term rental regulations. There are tenants and appts required with 24-48 hour notice

Some properties announce everything at once. Others reward the buyer w/ discernment to see what is quietly waiting to be realized. Set along the rise of Morse Hill Road, this Dorset home is a rare opportunity: a substantial residence on 10 acres where value extends beyond what exists today into what the land could become. Beyond a beautiful Vermont home, there is potential to shape an estate-scale setting w/ expanded lawns, layered gardens, paths, terraces, recreation areas and a more park-like relationship between house and land. Inside, the home is substantial and highly spacious. Numerous bedrooms, generous living areas, fireplaces, high ceilings, and a large family room designed for life's gathering. The layout suits quiet weekends, holidays, movie nights, guests, remote work, and longer Vermont stays. A enormous mudroom provides the practical transition every four-season home needs, w/ room for boots, coats, ski gear, and outdoor equipment. The full basement adds exceptional stora

Nestled in the small Vermont town of West Pawlet, this charming relic of yesteryear awaits your discovery. A proud testament to craftsmanship and heritage this Victorian built in 1910 exudes timeless appeal and offers a glimpse into a bygone era. Brimming with character, both the kitchen and dining room boast the century old built in wooden cabinets, living room with built in shelves and French doors. The gorgeous hardwood floors flow throughout the home adding warmth and elegance. Tray ceilings and the gorgeous original staircase whispers tales of generation past. Located on over a half acre with the Indian River meandering along your back yard offers that quintessential Vermont serenity. Charming Dorset hosting the Dorset Play house is merely in your back yard and the vibrant center of Manchester is only about about 25 minutes away. Start your new chapter and make this home your home! This vintage gem does need work but proves that Vermont living doesn't have to break the bank

Beautiful Dorset Contemporary Offering Privacy, Comfort, and Easy Living. If you've been looking for a private Vermont retreat with room to relax, entertain, and enjoy the beauty of every season, this exceptional custom home may be the perfect fit. Built in 1996 by respected Dorset builder Keith Dodson, this thoughtfully designed 5,731 sq. ft. contemporary sits on 12.15 peaceful acres with a pond and detached four-car garage. Inside, the home offers a welcoming and comfortable layout with 9 rooms, hardwood floors, radiant heat, central air with four zones, and a partial-house generator for added peace of mind. The kitchen features cherry cabinets, Corian countertops, a large island, cathedral ceiling, and easy access to the screened porch, an ideal spot for morning coffee or quiet summer evenings. The dramatic great room creates a wonderful gathering space, with its soaring two-story cathedral ceiling, skylights, exposed beams, built-ins, window seats, and balcony overlook. Throughout

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 for everyday living and entertaining. Enjoy the outdoors on your private deck, overlooking a fenced-in backyard ideal for kids, pets, or gardening. The lower level features a cozy family room with fireplace, creating a warm retreat for Vermont winters, plus a separate den/office - perfect for working from home or additional guest space. Additional Features: - Corner lot offering extra space and privacy - Attached two-car garage for convenience - Quiet, desirable Dorset location - Close to schools, shopping, and outdoor recreation This home is a perfect blend of function and charm - a must-see for anyone seeking space