Bennington County VT Houses for Sale

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  /38

  $502,900

  • 3 Beds
  • 1 Bath
  • 2,400 Sq Ft

  1059 Bailey Hill Rd, Readsboro, VT 05350

  Welcome to Bailey Hill Road in Readsboro, Vermont — a spacious retreat tucked away in the Green Mountains. With 2,400 square feet of finished living space, this home sits on a beautiful, private parcel of land that offers plenty of room to explore, garden, or simply soak in the peace and quiet of Vermont countryside. The interior features warm wood accents throughout, including exposed beams,

  The Hammond Team KW Vermont

  1059 Bailey Hill Rd, Readsboro, VT 05350
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• 

  

  

  /33

  $159,900

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft

  229 Division St, Bennington, VT 05201

  Welcome to this charming 1900's cottage, ideally situated in the heart of Bennington Village! This delightful home offers the perfect blend of historic charm and modern convenience, though it is well-loved and awaits your personal touch and some TLC to truly shine. Enjoy easy access to local shopping and schools, making daily errands and commutes a breeze. For outdoor enthusiasts, nearby trails

  Lilli West Maple Leaf Realty

  229 Division St, Bennington, VT 05201
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  /37

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 2,355 Sq Ft

  790 Maple Hill Rd, Arlington, VT 05250

  Experience the perfect Vermont country home - whether as a peaceful retreat or full-time residence - nestled on 13 private acres of open fields and woods with breathtaking mountain views. Thoughtfully updated, this inviting property features a brand-new modern kitchen with quartz countertops, a Bosch refrigerator and dishwasher, a Cafe induction stove, and a new chimney, blending elegance with

  Andy Reed Four Seasons Sotheby's Int'l Realty

  790 Maple Hill Rd, Arlington, VT 05250
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  /30

  $550,000

  • 2 Beds
  • 2 Baths
  • 2,218 Sq Ft

  1439 Main St, Manchester Center, VT 05255

  Purdy School House, est. 1850 - Step into history with this lovingly preserved former schoolhouse, offering timeless character with modern comfort. Featuring 2 bedrooms, 2 baths, and a striking stone fireplace, this home blends warmth and charm. A full basement and attached one-car garage provide practical convenience. Set on 2.01 acres, the property includes a fenced dog yard and plenty of space

  Richard Slocum Four Seasons Sotheby's Int'l Realty

  1439 Main St, Manchester Center, VT 05255
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  /43

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  683 Water St, North Bennington, VT 05257

  Completely redone in 2022, with the only evidence remaining of the 1934 construction being a crawlspace through a hatch in the rear of the basement. Offering 3 bedrooms and 2 bathrooms this home is very much "like new". All the systems are modern. Living room/dining room/kitchen, mud room with laundry and bedroom on the main level. Upstairs is the primary bedroom with private bathroom and an

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  683 Water St, North Bennington, VT 05257
• 

  

  /29

  $395,000

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft

  26 College Rd, North Bennington, VT 05257

  Here's the house you have been waiting for! An attractive 3-bedroom, 2-bath, brick-veneer cape, situated on a pretty corner lot, just a skip away from downtown North Bennington, with all its amenities, and next door to Bennington College. There's room for the family, with a flexible layout that offers lots of possibilities, including first-floor living, with a full bathroom on the first floor.

  Phil Lewis Mahar McCarthy Real Estate

  26 College Rd, North Bennington, VT 05257
• 

  

  /21

  $465,000

  • 4 Beds
  • 2 Baths
  • 1,337 Sq Ft

  3 Old Town Rd, Bondville, VT 05340

  This house is a must see for anyone looking for a small home in Vermont. Located between Stratton and Bromley and just minutes away from Magic Mountain, the location is prime ski country often referred to as the Golden Triangle.With four bedrooms and an open concept living room and kitchen, this home is cozy and inviting. Fully renovated and turnkey. Fenced in yard with hot tub. Fire

  Andrew King Stratton Real Estate

  3 Old Town Rd, Bondville, VT 05340
• 

  

  /41

  $285,000

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft

  3264 Route 153, West Rupert, VT 05776

  This neat and tidy single story home has been completely renovated from top to bottom, offering comfort, efficiency, and style. Updates include all new metal roof, vinyl siding, thermopane windows, propane hot-air heating system with heat pump central air conditioning, appliances, kitchen cabinets, counters, and hardwood flooring. Also updated plumbing, fiber optic internet, new electrical

  Scott McChesney McChesney RE, Inc.

  3264 Route 153, West Rupert, VT 05776
• 

  

  /43

  $185,000

  • 1 Bed
  • 400 Sq Ft

  634 Wiley Mountain Dr, Readsboro, VT 05350

  Escape to your own slice of paradise! This stunning vacation property, nestled within a serene tree farm, offers unparalleled privacy and tranquility. Fully furnished and move-in ready, it serves as a perfect vacation home or a lucrative Airbnb rental. Boasting ample land for recreation and potential expansion, this property is ideal for nature lovers and adventure seekers alike. Enjoy

  Cyd Scott Cohn & Company

  634 Wiley Mountain Dr, Readsboro, VT 05350
• 

  

  /26

  $249,900

  • 4 Beds
  • 2 Baths
  • 1,278 Sq Ft

  215 Maple St, Bennington, VT 05201

  Enjoy the charm and comfort of this beautifully renovated home, ideally nestled in the heart of Bennington. As you arrive, you'll be greeted by a spacious front porch, perfect for relaxation, entertaining, and enjoying cool breezes. This property has undergone a complete transformation from a two-family to a stunning single-family home. It now offers convenient one-floor living. The first floor

  Matt Waddington Hoffman Real Estate

  215 Maple St, Bennington, VT 05201
• 

  

  /22

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  3 Kimball Hill Rd Unit 1, Winhall, VT 05340

  Escape to the mountains in this charming A-frame, ideally located between the bustling town of Manchester and the area's best ski mountains. This home is your perfect base for year-round adventure, putting you just minutes from world-class skiing, hiking, mountain biking, and shopping.Inside, you'll find a comfortable layout featuring 3 bedrooms, 2 bathrooms, and a home office that can

  Robin Apps Four Seasons Sotheby's Int'l Realty

  3 Kimball Hill Rd Unit 1, Winhall, VT 05340
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  /36

  $959,000

  • 3 Beds
  • 2.5 Baths
  • 1,946 Sq Ft

  109 Nichols Hill Ln, Dorset, VT 05251

  This charming home with three acres is tucked in one of the lushest neighborhoods in Dorset, Nichols Hill Road is just two miles from the Dorset Green. The renovated kitchen features hand crafted maple cabinets, quartz counters, and a new downdraft range. The kitchen flows into a dining area and a sitting room with a wood-burning fireplace and a 7ft long window seat. The downstairs flooring is

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  109 Nichols Hill Ln, Dorset, VT 05251
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  /36

  $224,500

  • 5 Beds
  • 2 Baths
  • 2,212 Sq Ft

  1138 Main Rd, Stamford, VT 05352

  Stamford, VT - A country drive less than 10 minutes North Adams, MA- home of Mass MoCA. Dating back to 1850 this spacious home boasts 4 bedrooms & 2 baths. 1st floor bedroom, bath, laundry, kitchen, dining, living room, den & sunroom. Nestled on almost and acre of land and bordering a babbling brook this property offers a privacy sanctuary. Come take a look for yourself! Located close to

  Colleen Zajac MONARCH REALTY, INC.

  1138 Main Rd, Stamford, VT 05352
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  /37

  $999,000

  • 4 Beds
  • 3.5 Baths
  • 2,280 Sq Ft

  17 Roundtree Rd, Winhall, VT 05340

  Contemporary ski chalet on shuttle route located on a short cul-de-sac in the coveted North Brookwood neighborhood, a stone's throw from the Stratton base lodge. This 4 bedroom, 3 1⁄2 bath home boasts an open plan, walls of windows, and floor-to-ceiling stone fireplace in the Great Room. The pass-through kitchen was fully renovated in 2021 in addition to many other upgrades. Test your skills at

  Sarah Nichols Winhall Real Estate

  17 Roundtree Rd, Winhall, VT 05340
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  /44

  $399,000

  • 3 Beds
  • 1 Bath
  • 1,432 Sq Ft

  231 Bergrucken Ln, Readsboro, VT 05350

  Discover the perfect balance of privacy, outdoor adventure, and scenic beauty in this recently updated 3-bedroom, 1-bath home nestled in the heart of Vermont’s Green Mountains. Set on one of the largest lots in Alpenwald Village—approximately 6.8 acres—this rare gem is one of the few properties in the community offering mountain views and a true sense of tranquility.The property features

  Kristen Breeden Southern Vermont Realty Group

  231 Bergrucken Ln, Readsboro, VT 05350
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  /43

  $449,500

  • 4 Beds
  • 2 Baths
  • 2,374 Sq Ft

  464 Forest Mountain Rd, Peru, VT 05152

  Tucked within a serene wooded community, this home enjoys an intimate setting alongside a mountain brook. Outdoor adventure is at your doorstep - ski at Bromley, Stratton, or Magic, explore Wild Wings cross-country center, or wander countless hiking trails. An association trail just across from the driveway meanders alongside the brook for instant nature mindfullness time. Inside, warm knotty

  Nancy Jensen Four Seasons Sotheby's Int'l Realty

  464 Forest Mountain Rd, Peru, VT 05152
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  /37

  $399,000

  • 3 Beds
  • 1 Bath
  • 1,398 Sq Ft

  2566 Rupert Rd, Arlington, VT 05250

  Charming Cape on 5 Private Acres in Serene SandgateNestled amidst hundreds of acres of peaceful surroundings, this well-maintained 3-bedroom, 1-bath Cape offers the perfect blend of nature-inspired living and modern comfort. Set on five private acres, the property features lush gardens with thriving vegetables and herbs, a cozy outdoor fire pit, and a harmonious mix of open lawn and

  Faith Rhodes Maple Leaf Realty

  2566 Rupert Rd, Arlington, VT 05250
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  /60

  $2,995,000

  • 5 Beds
  • 4.5 Baths
  • 6,567 Sq Ft

  564 Overlook Rd, Manchester Center, VT 05255

  Tucked into the hills of Manchester on over 13 private acres, this mountain-modern home captures long-range views, refined interiors, and room to breathe. This light-filled 5-bedroom, 5-bath home offers an ideal blend of space and comfort just minutes from dining, shopping, and year-round recreation. The main level features a spacious primary suite with a large walk-in closet, en-suite

  Christiane Carroccio TPW Real Estate

  564 Overlook Rd, Manchester Center, VT 05255
• 

  

  /30

  $595,500

  • 3 Beds
  • 2.5 Baths
  • 1,850 Sq Ft

  93 Mountain Ridge Rd, Peru, VT 05152

  Looking for a cozy Cape-style home near skiing, top-rated schools, and year-round outdoor activities? This charming yet modern residence, just minutes from Bromley, Magic, and Stratton Mountains and close to Londonderry and Manchester, offers the perfect blend of solid construction and timeless character. Built from the ground up in 2002, it features wide pine floors with radiant heat throughout,

  Andy Reed Four Seasons Sotheby's Int'l Realty

  93 Mountain Ridge Rd, Peru, VT 05152
• 

  

  /29

  $379,000

  • 3 Beds
  • 1.5 Baths
  • 2,831 Sq Ft

  535 Red Mountain Rd, Arlington, VT 05250

  This beautifully updated farmhouse blends classic charm with modern convenience on a picturesque 3.6-acre lot. Featuring 3 bedrooms and 2 baths, including a first-floor bed and bath, this home offers flexible living space for guests, multigenerational living, or a home office setup. Enjoy the open kitchen/living area with a cozy woodstove (2022), a spacious great room ideal for entertaining, a

  Annette Gallo Real Broker LLC

  535 Red Mountain Rd, Arlington, VT 05250
• 

  

  /23

  $360,000

  • 3 Beds
  • 2 Baths
  • 1,590 Sq Ft

  22 Carlen St, Manchester Center, VT 05255

  Live in one and rent the other. Discover the charm and value of this affordable starter home with rental option. Located in a quiet, residential area of Manchester. This spacious ranch-style property offers a rare combination of flexibility, space, and opportunity, perfect for first-time buyers, investors, or anyone looking to create their dream home with a few finishing touches. The main level

  Andy Reed Four Seasons Sotheby's Int'l Realty

  22 Carlen St, Manchester Center, VT 05255
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  /28

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  139 Bergwelt Ln, Readsboro, VT 05350

  Charming Country Retreat with Scenic Views and Timeless Character.Welcome to your dream country escape! Nestled on a peaceful, tree-lined lane, this beautifully maintained 3-bedroom, 2-bathroom home offers the perfect blend of rustic charm and modern comfort. Set on a spacious 3.6 acre lot, the property boasts serene views, mature gardens, and ample privacy — ideal for relaxing weekends or

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  139 Bergwelt Ln, Readsboro, VT 05350
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  /30

  $349,995

  • 3 Beds
  • 2 Baths
  • 1,753 Sq Ft

  374 Overlea Rd, North Bennington, VT 05257

  A stunning three bedroom, two bath home on a wooded lot with mountain views and bordered on several sides by serene farm pastures! Just a few minutes from downtown Bennington and even closer to the village of North Bennington! Tons of natural light inside that compliments the updated kitchen and open dining / living room areas. First floor includes enclosed rear sun porch/mudroom, laundry and

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  374 Overlea Rd, North Bennington, VT 05257
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  /60

  $369,900

  • 0.5 Baths
  • 4,220 Sq Ft

  6828 Main St, Readsboro, VT 05350

  Don’t miss your chance to own a piece of Vermont history in the heart of Readsboro. The iconic Readsboro General Store is now available and ready for your vision. Perfectly positioned on Main Street, just steps from the town green, this high-visibility property has long been a favorite stop for locals, visitors, and nearby trail users alike. Currently configured for mixed-use, the building

  Flex Realty Group Flex Realty

  6828 Main St, Readsboro, VT 05350
• 

  

  /17

  $485,000

  • 2 Beds
  • 1 Bath
  • 1,144 Sq Ft

  1376 Shaftsbury Hollow Rd, Shaftsbury, VT 05262

  Discover a true Vermont lifestyle at this meticulously maintained charming farmhouse nestled on picturesque Shaftsbury Hollow Road. This property combines historic character with thoughtful modern updates, offering a serene retreat with breathtaking mountain views across a just shy of 10-acre lot where the White Creek gracefully runs along one side and the entire back boundary. Step out onto the

  Lori Hurley Four Corner Properties LLC

  1376 Shaftsbury Hollow Rd, Shaftsbury, VT 05262
• 

  

  /44

  $499,000

  • 4 Beds
  • 2 Baths
  • 1,708 Sq Ft

  144 Oberdorf Rd, Readsboro, VT 05350

  Charming 4-Bedroom Chalet on 2 Acres in Scenic Readsboro, VermontEscape to the beauty of southern Vermont. Whether you're looking for a full-time residence or the perfect vacation getaway, this beautifully updated home offers comfort, style, and proximity to all-season recreation.Step inside to discover thoughtful upgrades throughout, including fully renovated bathrooms and a

  Evan Russell Real Broker LLC

  144 Oberdorf Rd, Readsboro, VT 05350
• 

  

  /59

  $2,800,000

  • 3 Beds
  • 3.5 Baths
  • 3,938 Sq Ft

  23 Valley View Rd, Winhall, VT 05340

  Set at the end of a long, private driveway, this remarkable property unveils dramatic panoramic vistas that stretch nearly 40 miles. Offering a rare sense of seclusion & grandeur, the home is an ideal retreat where nature, privacy, and beauty converge.Designed w/a modern aesthetic,an expansive open-concept layout, the main floor features a stunning stone fireplace , enhanced by soaring ceilings

  Kim Morgan-Wohler Wohler Realty Group

  23 Valley View Rd, Winhall, VT 05340
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  /36

  $399,000

  • 5 Beds
  • 3 Baths
  • 3,118 Sq Ft

  100 McCarthy Acres, North Bennington, VT 05257

  Nearly Lakefront Living in the Heart of North Bennington!Come for the space—stay for the location! This spacious home offers over 2,500 sq. ft. of living space, including 5 bedrooms, 3 full bathrooms, a large home office in the finished basement, and a versatile 250 sq. ft. bonus room attached to one of the upstairs bedrooms. The original garage has been thoughtfully transformed into a 600

  Nicholas Charest Maple Leaf Realty

  100 McCarthy Acres, North Bennington, VT 05257
• 

  

  /32

  $368,000

  • 3 Beds
  • 2 Baths
  • 1,337 Sq Ft

  78 Carbonti Cir, Arlington, VT 05250

  Easy single-level living! Welcome to Arlington's Carbonti Circle. Updated three-bedroom, two-bath ranch nestled in a quiet neighborhood setting just minutes from downtown Arlington and the famous Battenkill River. Set on a .30-acre lot, this home offers the perfect blend of comfort, character and convenience. Experience easy living in this beautifully maintained single-level home! Enjoy a

  Margretta Fischer Wohler Realty Group

  78 Carbonti Cir, Arlington, VT 05250
• 

  

  /41

  $365,000

  • 2 Beds
  • 2 Baths
  • 1,542 Sq Ft

  509 Thompson Pond Rd, Pownal, VT 05261

  Discover Your Perfect Getaway at Verdmont If you're a nature enthusiast, a rare and exclusive opportunity awaits at the Verdmont Outing Club. Nestled in the heart of the Green Mountain Preserve, this gated community spans nearly 500 acres of unspoiled wilderness-a true haven for outdoor living.As a shareholder, you'll enjoy a wealth of amenities: Water & Land Privileges: Two stunning

  Kelley Mccarthy Mahar McCarthy Real Estate

  509 Thompson Pond Rd, Pownal, VT 05261
• 

  

  /20

  $225,000

  • 6 Beds
  • 1.5 Baths
  • 2,082 Sq Ft

  266 Robillard Rd, Stamford, VT 05352

  SOUTHERN VERMONT!~ Great country location with over a 1/2 acre of beautiful lawns & perennial flower. Sitting porch, large kitchen with pantry opens to dining & living room. Oak hardwood floors on 1st floor. 2nd level has 4 good sized rooms & 3rd level has 2 very nice rooms & a 1/2 bath. Laundry is in basement. Basement appears to be dry. Oil boiler & wood burning furnace in the basement. Lots of

  Colleen Zajac Monarch Realty

  266 Robillard Rd, Stamford, VT 05352
• 

  

  /37

  $2,400,000

  • 5 Beds
  • 4.5 Baths
  • 3,252 Sq Ft

  115 Benson Fuller Dr, Jamaica, VT 05343

  Perched on 3.5 private acres with commanding views from Stratton’s iconic slopes to Bromley’s trails, this architecturally striking residence blends the serenity of the mountains with sophisticated modern design. A dramatic central staircase anchors the home, leading to a sleek custom kitchen and a vaulted great room where walls of glass frame panoramic vistas. A floor-to-ceiling stone fireplace

  Carrie Mathews Winhall Real Estate

  115 Benson Fuller Dr, Jamaica, VT 05343
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  /36

  $498,000

  • 3 Beds
  • 2 Baths
  • 1,671 Sq Ft

  6 Dwyers Camp Rd, Shaftsbury, VT 05262

  Discover quintessential Vermont living in this charming home, ideally situated on 6.9 serene acres in scenic Shaftsbury, a picturesque town in Southern Vermont. This meticulously maintained residence offers a blend of rustic charm and modern sophistication, providing a tranquil retreat with convenient access to area amenities and attractions. Thoughtful renovations have elevated its interior,

  Lori Hurley Four Corner Properties LLC

  6 Dwyers Camp Rd, Shaftsbury, VT 05262
• 

  

  /60

  $1,825,000

  • 3 Beds
  • 4 Baths
  • 2,872 Sq Ft

  36 Beaver St, Bondville, VT 05340

  Your Ultimate Vermont Mountain Retreat Awaits! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape—crafted for adventure, relaxation, and making lasting memories in every season. Whether you’re hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage, this property delivers! Plus, it's only a 10-minute

  MaryKate Grey Stratton Real Estate

  36 Beaver St, Bondville, VT 05340
• 

  

  /16

  $145,000

  • 3 Beds
  • 1.5 Baths
  • 1,485 Sq Ft

  755 Main St, Bennington, VT 05201

  Many possibilities with this property located on Main Street in Bennington. Zoned village commercial but currently a 3 bedroom 1 and a half bath home. Nice kitchen, dining room, living room, main level primary with half bath, main level laundry and more. Needs some TLC. Won't qualify for first time homebuyer programs.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  755 Main St, Bennington, VT 05201
• 

  

  /42

  $364,900

  • 4 Beds
  • 1.5 Baths
  • 1,728 Sq Ft

  639 Wiley Mountain Rd, Readsboro, VT 05350

  Updated mountain home on 13.63 flat, usable acres bordering the Green Mountain National Forest and offering an outdoor paradise in every season. Tucked at the top of a quiet road, this property blends comfort, space, and access to Vermont’s best year-round recreation.Inside, you’ll find new hardwood floors, a renovated kitchen and bathrooms, a main-level bedroom, a full bath, main-level

  Melissa Nebelski Skihome Realty

  639 Wiley Mountain Rd, Readsboro, VT 05350
• 

  

  /55

  $2,225,000

  • 4 Beds
  • 4.5 Baths
  • 5,000 Sq Ft

  16 Hunter Ridge Rd, Bondville, VT 05340

  Custom built Wadsworth Design Build timber-frame mountain retreat blends luxury, craftsmanship, and convenience just minutes from Stratton Mountain Resort. Set on 2.66 acres and spanning 5,000± square feet, this 4-bedroom, 5-bath home includes two additional sleeping space ideal for hosting friends and family. A grand entry framed by oversized Douglas fir posts welcomes you into a lodge style

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  16 Hunter Ridge Rd, Bondville, VT 05340
• 

  

  /57

  $1,795,000

  • 5 Beds
  • 4.5 Baths
  • 3,218 Sq Ft

  5491 Vt Route 315, Rupert, VT 05776

  Luxury home, move-in ready, on 5+ peaceful acres with protected panoramic mountain views and stream frontage, this fully renovated 1909 Federal offers timeless character with a like-new feel—just 2.5 miles from the Dorset Green and dining but away from the bustle. Every inch of the main home has been meticulously updated with premium materials and workmanship. A custom walnut kitchen with

  Annette Gallo Real Broker LLC

  5491 Vt Route 315, Rupert, VT 05776
• 

  

  /36

  $1,790,000

  • 4 Beds
  • 3 Baths
  • 2,545 Sq Ft

  1949 South Rd, Peru, VT 05152

  Nestled in a serene and picturesque setting, Berry Hill Farm offers a rare opportunity to own an exceptional Vermont estate blending charm, versatility, and natural beauty. Spanning 15.52 acres across two separately deeded lots, the property combines inspired design with modern comfort. At its heart is a beautifully crafted contemporary home featuring three spacious bedrooms, sunlit living

  Kim Morgan-Wohler Wohler Realty Group

  1949 South Rd, Peru, VT 05152
• 

  

  /45

  $3,600,000

  • 4 Beds
  • 3.5 Baths
  • 2,338 Sq Ft

  198 Church St, Dorset, VT 05251

  Nestled in the heart of the iconic Dorset village, just steps from the Dorset Field Club and the beloved local theater, this enchanting historic home has been meticulously renovated, rejuvenated, and reimagined with no expense spared. From the moment you arrive, the home's timeless charm and thoughtful updates are evident. A complete reengineering of the roof and replacement of all major systems

  Adrienne Sherwood Four Seasons Sotheby's Int'l Realty

  198 Church St, Dorset, VT 05251

Showing Results 41 - 80, Page 2 of 4