Bennington County VT Houses for Sale

• 

  

  

  /20

  $549,000

  $146K PRICE DROP

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

  27 Owls Head Hill Ln, Dorset, VT 05251

  Charming Raised Ranch on 2 Acres – Dorset, VTWelcome 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 GarageStep inside to find a bright living room that flows seamlessly into the eat-in kitchen, perfect for everyday

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  27 Owls Head Hill Ln, Dorset, VT 05251
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• 

  

  

  /53

  $1,695,000

  • 3 Beds
  • 2.5 Baths
  • 4,120 Sq Ft

  1944 Monument Ave, Bennington, VT 05201

  Set on 5.63 beautiful acres in one of Bennington's most desirable locations, this exceptional 1880 historic home has been thoughtfully renovated inside and out, blending timeless character with sophisticated modern amenities. The property includes approximately 3,200 square feet in the main residence, an attached two-car garage with a second kitchen, and a separate 1,000-square-foot one-bedroom

  Kelley Mccarthy Mahar McCarthy Real Estate

  1944 Monument Ave, Bennington, VT 05201
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  /32

  $315,000

  • 3 Beds
  • 1.5 Baths
  • 1,365 Sq Ft

  314 Chester Knoll Dr, Bennington, VT 05201

  There is something special about a home that has been truly loved, and you can feel it the moment you step inside. Exceptionally clean, beautifully cared for, and thoughtfully maintained, this inviting three-bedroom home is tucked into a peaceful little neighborhood with nearby walking trails and a stream that adds to the sense of calm and community.Inside, the home feels bright, comfortable,

  Faith Rhodes Maple Leaf Real Estate

  314 Chester Knoll Dr, Bennington, VT 05201
• 

  

  

  /36

  $609,900

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,250 Sq Ft

  23 Stonewall Ln, Dorset, VT 05251

  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

  Brian Hill Remax Summit

  23 Stonewall Ln, Dorset, VT 05251
• 

  

  

  /55

  $5,995,000

  New Construction $4M PRICE DROP

  • 6 Beds
  • 9 Baths
  • 10,993 Sq Ft

  551 West Fields, Manchester, VT 05254

  Discover "the pinnacle of luxury living" in the heart of Manchester Village! Crafted by Breen Builders and Ramsay Gourd Architect, every detail reflects superior craftsmanship and timeless elegance! From the very foundation to the finishing touches, attention to detail and commitment to quality shine through! Experience the perfect blend of luxury and convenience in this stunning 10,000 sq.ft

  Sunny Breen Josiah Allen Real Estate, Inc.

  551 West Fields, Manchester, VT 05254
• 

  

  /27

  $650,000

  $25K PRICE INCREASE

  • 4 Beds
  • 4.5 Baths
  • 3,864 Sq Ft

  6265 Vt Route 7a, Sunderland, VT 05250

  Extensively Renovated Classic Vermont ColonialThis beautifully updated 1935 Vermont Colonial offers the perfect blend of classic charm and modern convenience, with thoughtful additions completed in 1972 and 2016. With nearly 3,900 square feet of living space, this spacious home features 4 bedrooms, 4.5 bathrooms, two dedicated office spaces, and a versatile third-story bonus room, ideal for a

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  6265 Vt Route 7a, Sunderland, VT 05250
• 

  

  /11

  $169,900

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 848 Sq Ft

  302 U S 7 S, Woodford, VT 05201

  Over 3 acres, a brook and lots of woods for walking. Room for a terraced garden, tons of parking and minutes to Bennington! This 2 bedroom ranch style home has a huge eat in kitchen and a lovely big living room with lots of windows. There is a bonus sun room with laundry. Owners are using an attached shed as a chicken coop! Sweet find at this affordable price!

  Christine Lewis Brattleboro Area Realty

  302 U S 7 S, Woodford, VT 05201
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  /34

  $579,000

  • 3 Beds
  • 2 Baths
  • 2,501 Sq Ft

  856 Matteson Rd, Bennington, VT 05201

  Escape to your own private Vermont retreat with this beautiful log home, tucked away in a peaceful, secluded setting surrounded by several acres of thoughtfully landscaped grounds, yet minutes from shopping and dining. From the stamped concrete patio and charming fish pond with waterfall to your very own putting green, this property was designed for enjoying life both indoors and out.Step

  Lilli West Maple Leaf Real Estate

  856 Matteson Rd, Bennington, VT 05201
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  /52

  $230,000

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  113 Main St, Bennington, VT 05201

  Charming downtown family home with modern upgrades and timeless appeal. This beautifully updated 3-bedroom home is perfectly situated on a corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, the home features a recently added first-floor primary bedroom and a new mudroom entry.Step inside to find gleaming newly upgraded flooring, a warm and inviting

  Lindsey Martin Maple Leaf Real Estate

  113 Main St, Bennington, VT 05201
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  /48

  $429,000

  • 2 Beds
  • 2 Baths
  • 7,000 Sq Ft

  3310 Vermont 346, Pownal, VT 05260

  Former Church Offers So Many Opportunities. What might be your dream or requirements? This 1889 Church located in the quiet country village of North Pownal, Vermont, could fill them, however big or small. A single family home for all seasons and celebrations? A wedding venue? A place to live and work, rolled into one with plenty of space no matter what you do, from sculpting to computer imaging?

  Paul Harsch HARSCH ASSOCIATES

  3310 Vermont 346, Pownal, VT 05260
• 

  

  /45

  $525,000

  $40K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,594 Sq Ft

  191 Pleasant Street Extension, East Dorset, VT 05253

  "COME TAKE A PEEK, IT'S JUST ACROSS THE CREEK.....Enjoy an inviting front porch to unwind and breathe in the serene surroundings! Unwind and take in the lovely mountain views, all set on the scenic Tom River in East Dorset! Charming saltbox style (1982 circa), the design is open living spaces with abundant light through out... As an added bonus this property boasts an over sized two car garage

  Sunny Breen Josiah Allen Real Estate, Inc.

  191 Pleasant Street Extension, East Dorset, VT 05253
• 

  

  /20

  $835,000

  • 3 Beds
  • 2.5 Baths
  • 2,780 Sq Ft

  232 Powderhorn Rd, Manchester Center, VT 05255

  Single family home on private, family-oriented street 5 minutes from town/schools.Excellent school system.30 minutes from ski slopes.New roof within 3 years.Updated appliances.

  David White OwnerEntry.com

  232 Powderhorn Rd, Manchester Center, VT 05255
• 

  

  /23

  $695,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  57 Pearl Buck Dr, Bondville, VT 05340

  Perched high on Pearl Buck Drive, this distinctive Vermont home is all about location—and the scenery is truly exceptional. Sweeping mountain vistas capture both Stratton and Bromley, creating a dramatic backdrop in every season, from autumn color and snow-covered peaks to long summer sunsets. The road also carries a special local connection to Pearl S. Buck, the Pulitzer- and Nobel Prize-winning

  Carrie Mathews Winhall Real Estate

  57 Pearl Buck Dr, Bondville, VT 05340
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  /43

  $319,900

  $20K PRICE DROP

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

  683 Water St, North Bennington, VT 05257

  Much larger than it looks and 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

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  683 Water St, North Bennington, VT 05257
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  /53

  $205,000

  • 3 Beds
  • 1.5 Baths
  • 1,632 Sq Ft

  305 Weeks St, Bennington, VT 05201

  Experience refined living in this beautifully appointed tri-level townhouse-style condominium, ideally situated just moments from downtown, the hospital, shopping, and dining. Rich in vintage character while thoughtfully updated for modern living, this exceptional residence showcases elegant quartz and butcher block countertops, a designer tile backsplash, and striking marble flooring that create

  Lindsey Martin Maple Leaf Real Estate

  305 Weeks St, Bennington, VT 05201
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  /36

  $1,075,000

  • 4 Beds
  • 5 Baths
  • 3,982 Sq Ft

  844 E Manchester Rd, Manchester Center, VT 05255

  Steeped in history and surrounded by natural beauty, this magnificent 1850 antique estate offers a rare blend of timeless character and modern luxury. Set well back from the road, the home occupies a peaceful setting that seamlessly pairs total privacy with ultimate convenience, sitting just minutes from downtown and premier ski mountains while capturing breathtaking views of the Green Mountains.

  Stephanie Sugden Real Broker LLC

  844 E Manchester Rd, Manchester Center, VT 05255
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  /27

  $1,200,000

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  233 Squires Rd, Manchester Center, VT 05255

  Tucked into the picturesque countryside of Manchester, this nearly 19-acre Vermont property offers a rare blend of privacy, income potential, and endless opportunity. Just minutes from downtown Manchester, the location provides easy access to the Orvis Fly Fishing School, Equinox Mountain, the Batten Kill River, and year-round recreation at Bromley Mountain Ski Resort. Surrounded by natural

  Mark Triller Real Broker LLC

  233 Squires Rd, Manchester Center, VT 05255
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  /51

  $1,795,000

  • 3 Beds
  • 3 Baths
  • 5,228 Sq Ft

  2167 Myers Rd, Shaftsbury, VT 05262

  Welcome to Hidden Ponds Farm - a breathtaking retreat set on 40 sprawling acres where history and refined country living meet in perfect harmony. This extraordinary early 1800s post-and-beam converted barn has been thoughtfully reimagined, preserving its authentic character while seamlessly integrating modern comforts. A magnificent 1,000-foot hand-placed stone wall winds gracefully across the

  Kelley Mccarthy Mahar McCarthy Real Estate

  2167 Myers Rd, Shaftsbury, VT 05262
• 

  

  /50

  $330,000

  $15K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,750 Sq Ft

  1141 Burgess Rd, Bennington, VT 05201

  Completely renovated, turnkey single-level home offering mountain views, modern finishes, and a beautiful country setting. All major systems and cosmetic updates were completed within the last year, including a brand-new roof and new windows.The light-filled interior layout features 2 bedrooms, 2 full bathrooms, brand-new wood flooring across all main living areas, plush new bedroom

  Kate Barry EXP Realty

  1141 Burgess Rd, Bennington, VT 05201
• 

  

  /25

  $1,200,000

  Open House 10/10

  • 6 Beds
  • 3.5 Baths
  • 4,017 Sq Ft

  11 Founders Hill Rd, Winhall, VT 05360

  Selling very close to the assessed value of $1,126,100!!! This 2026 town assessment just made this property a REAL DEAL because the Owner wants 1,200,000. This property can be sold furnished or unfurnished with closing before the ski season is here. 6 bedrooms and 3.5 bathrooms to accommodate your family and guests. Enjoy 2 primary suites with attached baths and one is on the main floor. Walk in

  Derek Greene Derek Greene

  11 Founders Hill Rd, Winhall, VT 05360
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  /49

  $399,000

  $50K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 3,096 Sq Ft

  928 Main Rd, Stamford, VT 05352

  Welcome to the heart of Stamford, Vermont, where small-town charm meets endless opportunity. Set on 3.99 level acres with beautiful mountain views, this former historic general store has been transformed into a spacious 3,096 sq. ft. residence designed for today's flexible lifestyle. The main home offers 3 bedrooms, open living spaces, and room for everyone, while the separate second-floor

  Christine Girard Lamacchia Realty, Inc. - North Adams

  928 Main Rd, Stamford, VT 05352
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  /60

  $4,995,000

  $255K PRICE DROP

  • 9 Beds
  • 10 Baths
  • 7,900 Sq Ft

  1184 E Manchester Rd, Manchester, VT 05255

  Peacock Hollow, a c.1790 completely private estate, is gracefully sited on 29.9 acres surrounded by sweeping mountain views, a running stream, and bordered by the forest. This rare offering combines historic character with refined updates, creating a legacy property designed for both intimate living and grand entertaining. The 5,500 square foot main residence offers five beautifully appointed

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  1184 E Manchester Rd, Manchester, VT 05255
• 

  

  /40

  $1,699,000

  • 4 Beds
  • 4 Baths
  • 2,951 Sq Ft

  1949 South Rd, Peru, VT 05152

  Discover Berry Hill Farm, an exceptional Vermont estate where inspired design, extraordinary craftsmanship, and natural beauty come together in one remarkable setting. Offering privacy, versatility, and a deep connection to the landscape, this unique property encompasses 15.52 acres across two separately deeded parcels, creating a rare offering for a Southern Vermont retreat. The contemporary

  Helen Nault

  1949 South Rd, Peru, VT 05152
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  /52

  $2,285,000

  • 5 Beds
  • 4.5 Baths
  • 4,647 Sq Ft

  543 Lower Hollow Rd, Dorset, VT 05251

  A Serene Dorset Hollow Retreat Along the Mettowee RiverTucked 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 spaces include a

  Britt Wohler

  543 Lower Hollow Rd, Dorset, VT 05251
• 

  

  /39

  $175,000

  • 2 Beds
  • 1 Bath
  • 810 Sq Ft

  220 Gage St, Bennington, VT 05201

  Tired of renting? Discover the charm, convenience, and value of this adorable two-bedroom bungalow - an ideal opportunity for first-time buyers, downsizers, investors, or anyone looking for a cozy second home in town.Tucked away from the hustle and bustle, this historic home is just a short walk from downtown shopping, restaurants, transportation, and everyday conveniences. Inside, you'll

  Justine Curry Maple Leaf Real Estate

  220 Gage St, Bennington, VT 05201
• 

  

  /30

  $899,000

  • 4 Beds
  • 3 Baths
  • 2,421 Sq Ft

  45 Benson Fuller Dr, Bondville, VT 05340

  Shred Shack: the portfolio's workhorse. A post-and-beam Stratton ski house with mountain views on 2.2 private acres, about 6 minutes to the base. Soaring timber great room with stone wood-burning fireplace and indoor swing, knotty-pine kitchen with bar seating, big farm-table dining, wrap-around deck with hot tub, indoor barrel sauna, outdoor fireplace and Level 2 EV charger. 4 bedrooms (bunk

  David Powers 42 North LP

  45 Benson Fuller Dr, Bondville, VT 05340
• 

  

  /59

  $989,900

  • 4 Beds
  • 3 Baths
  • 5,697 Sq Ft

  66 Somerset Rd, Searsburg, VT 05363

  LOW TAXES! Six oversized garage bays across two multi-level outbuildings, direct access to National Forest, backyard waterfalls, and 5.4 private acres make this gated Southern Vermont retreat unlike anything else near Wilmington. Just five miles from downtown Wilmington and less than 12 miles from Mount Snow, the property combines substantial space for living and entertaining with exceptional

  Erica Reynolds Southern Vermont Realty Group

  66 Somerset Rd, Searsburg, VT 05363
• 

  

  /50

  $449,900

  • 4 Beds
  • 2.5 Baths
  • 2,396 Sq Ft

  18 Greenview Dr, Bennington, VT 05201

  Come home to the warmth and character of this inviting 4-bedroom, 2.5-bathroom log cabin, tucked into a desirable Bennington neighborhood on .46 acres. From the welcoming front porch to the cozy interior, this home offers the charm of log construction with plenty of space for comfortable everyday living. The living room is the heart of the home, featuring a fireplace and sliding doors that open

  Julie Glover Mahar McCarthy Real Estate

  18 Greenview Dr, Bennington, VT 05201
• 

  

  /60

  $999,000

  • 4 Beds
  • 3.5 Baths
  • 7,102 Sq Ft

  134 Grapevine Ln, Pownal, VT 05261

  Custom-built and truly exceptional, this phenomenal home is set on 5.81 wooded acres, offering privacy, space, and room for everyone. With 12 rooms, 4 bedrooms, and 4 bathrooms, this spacious home is designed for comfortable living and effortless entertaining. The first-floor primary suite features a beautiful private bath, and adjacent laundry room. The inviting family room offers cathedral

  Moira Spivey Four Seasons Sotheby's Int'l Realty

  134 Grapevine Ln, Pownal, VT 05261
• 

  

  /42

  $180,000

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft

  105 Hicks Ave, Bennington, VT 05201

  Back on the market- This one is for the buyer that sees potential, not perfection! Opportunity awaits at this unique property with an exceptional setting along the Walloomsac River. A true Vermont farmhouse offering three bedrooms and two bathrooms, situated on a flat, park-like lot with mature landscaping, open green space, and beautiful river frontage. The serene setting creates a peaceful

  Angela Bevin Maple Leaf Real Estate

  105 Hicks Ave, Bennington, VT 05201
• 

  

  /60

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 3,295 Sq Ft

  142 Schenkar Rd, Pownal, VT 05261

  Welcome to your own private oasis! Set on 30 private wooded acres, this well-maintained three-bedroom, 2.5-bath Colonial presents a rare opportunity to enjoy expansive acreage, exceptional mountain views (including the Bennington Battle Monument!), and peaceful surroundings in a highly versatile tri-state location near the Vermont, Massachusetts, and New York borders. The 2,083 square-foot home

  Erin McCormick KW Vermont

  142 Schenkar Rd, Pownal, VT 05261
• 

  

  /30

  $395,000

  • 4 Beds
  • 1.5 Baths
  • 1,816 Sq Ft

  2 Bromley Ln, North Bennington, VT 05257

  Charming 4-bedroom, 1.5 bathroom house on private lane in desirable North Bennington, steps from Bennington College and a short walk to the Village center's restaurants, library, and shops. The home's first floor features an updated eat-in kitchen with granite countertops, dining room, living room with fireplace, half bath, and study with built-in bookcases, as well as a sun room which leads to

  Allison Pacelli PACELLI ZEPKA

  2 Bromley Ln, North Bennington, VT 05257
• 

  

  /52

  $179,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  130 Morgan St, Bennington, VT 05201

  200 feet of Walloomsac River front .There is a second kitchen for a possible in-law or AB&B. RV parking for those visitors who travel listing to the sounds of the stream for the nomadic visitors. New replacement windows were just done. Bring your imagination and see the possibilities. Showings start 8/18/2026

  Dan Mason Perrott Realty

  130 Morgan St, Bennington, VT 05201
• 

  

  /60

  $1,500,000

  $350K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,828 Sq Ft

  400 Spring Brook Rd, Arlington, VT 05250

  Tucked at the end of a private, town-maintained road at the base of Red Mountain, this exceptional property offers privacy and flexibility: two fully independent residences, beautiful grounds and a peaceful setting just minutes from the heart of Arlington and an easy drive to Manchester. Surrounded by gardens, orchards, terraces, and forest, this is a true Vermont retreat. The 2,676-square-foot

  Emily Heyer Hoffman Real Estate

  400 Spring Brook Rd, Arlington, VT 05250
• 

  

  /34

  $1,500,000

  • 5 Beds
  • 4 Baths
  • 4,173 Sq Ft

  180 High Meadow Rd, Winhall, VT 05340

  First Chair Lair: a proven, turnkey Stratton rental on High Meadow, on the complimentary winter-weekend Stratton shuttle route and about 5 minutes to the base. Two-story great room with brick wood-burning fireplace and cathedral pine ceilings, renovated 2024-25 kitchen and baths, dining for 12, private hot-tub deck, and a lower-level game room (pool table, arcade, darts, foosball). Five bedrooms

  David Powers 42 North LP

  180 High Meadow Rd, Winhall, VT 05340
• 

  

  /52

  $299,000

  $10K PRICE INCREASE

  • 3 Beds
  • 1.5 Baths
  • 1,411 Sq Ft

  262 Union St, Bennington, VT 05201

  Just a short walk to downtown shopping and dining you can move right into this well-maintained and thoughtfully updated 3-bedroom, 2-bath home offering comfortable living spaces, modern conveniences, and plenty of room to spread out both inside and out.The heart of the home is the spacious, updated kitchen featuring a center island, abundant counter top space, and generous cabinetry, and even

  William Paquin Maple Leaf Real Estate

  262 Union St, Bennington, VT 05201
• 

  

  /26

  $165,000

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  128 Burgess Rd, Bennington, VT 05201

  Affordable homeownership awaits at 128 Burgess Road in Bennington! This compact 2-bedroom, 1-bath home offers approximately 840 square feet of living space with a practical layout and low utility costs. Several recent exterior improvements include brand-new siding, new rear entry stairs and a new electrical meter board in Spring 2026. The home also features vinyl replacement windows, including

  Emily Heyer Hoffman Real Estate

  128 Burgess Rd, Bennington, VT 05201
• 

  

  /24

  $1,250,000

  • 3 Beds
  • 2.5 Baths
  • 2,035 Sq Ft

  84 Overlook Rd, East Dorset, VT 05253

  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.The thoughtfully

  Carol O`Connor Four Seasons Sotheby's Int'l Realty

  84 Overlook Rd, East Dorset, VT 05253
• 

  

  /50

  $279,500

  • 2 Beds
  • 2 Baths
  • 1,128 Sq Ft

  257 Watrous Rd, Rupert, VT 05768

  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 & Farmland Center, this property offers incredible privacy and direct outdoor access. Perfectly suited as a year-round home,

  Scott McChesney McChesney RE, Inc.

  257 Watrous Rd, Rupert, VT 05768
• 

  

  /40

  $434,500

  $45K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,861 Sq Ft

  120 Village St, East Dorset, VT 05253

  Antique charmer in the village of East Dorset was originally built in the 1850s by famous lumberman, F.G. Harwood. . An addition followed in 1900, and thoughtful improvements over the years have created a gracious Colonial farmhouse with approximately 3,861 square feet of living space, an oversized two-car garage, and 1.1 acres. The expansive floor plan offers a primary suite with an oversized

  Dana Kingsley Josiah Allen Real Estate, Inc.

  120 Village St, East Dorset, VT 05253

Showing Results 41 - 80, Page 2 of 5