Bennington County VT Homes for Sale

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  /50

  $465,000

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  1284 Granger Hollow Rd, Shaftsbury, VT 05262

  Magnificent setting on 4 scenic acres in rural Shaftsbury, this classic 1979 Saltbox offers the perfect blend of Vermont charm, functional space, and meaningful updates. Surrounded by rolling landscape and mountain views, the vibe is peaceful and inviting—ideal for those seeking privacy without sacrificing convenience. Inside, the home features a warm and welcoming layout highlighted by natural

  Jenifer Prouty Hoffman Hoffman Real Estate

  1284 Granger Hollow Rd, Shaftsbury, VT 05262
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  /55

  $239,500

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft

  38 Cyr Ct, Bennington, VT 05201

  This classic 1975 ranch offers comfortable single-level living with great potential to make it your own. Featuring three bedrooms, including a primary with its own bath. The home provides a functional layout suited to a variety of lifestyles. A spacious living area and eat-in kitchen create a welcoming foundation for everyday living and entertaining. While the home could benefit from some

  Catherine Cairns Maple Leaf Realty

  38 Cyr Ct, Bennington, VT 05201
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  /60

  $875,000

  • 4 Beds
  • 3 Baths
  • 2,462 Sq Ft

  636 Dexter Rd, Shaftsbury, VT 05262

  In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic local backroads to write “Stopping by the Woods on a Snowy Evening." The Dexter Road Farmhouse, dating back 225 years, remains a testament to the enduring charm of Vermont and the simpler rhythms of country life. Nestled at the end of a serene, tree-lined town road, this charming 1800 farmhouse captures the

  

  Kristin Comeau

  TPW Real Estate

  (802) 727-7584

  636 Dexter Rd, Shaftsbury, VT 05262
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  /51

  $750,000

  • 3 Beds
  • 3 Baths
  • 3,498 Sq Ft

  360 Mending Walls Rd, Manchester Center, VT 05255

  Mending Walls on the cul-de-sac, a three bedroom family residence that provides a quiet location in a great neighborhood... There are three finished floors. Open great-room kitchen with propane fireplace and comfy sitting area that extends to a very large deck system with attached screen porch. There is a formal dining room if needed or office and den on the main level, the expansive mudroom area

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 215-5395

  360 Mending Walls Rd, Manchester Center, VT 05255
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  /36

  $395,000

  • 3 Beds
  • 2 Baths
  • 1,808 Sq Ft

  1768 Barnumville Rd, Manchester Center, VT 05255

  The Valley is Calling! This charming Cape-style home features three bedrooms and two bathrooms, including a convenient first-floor bedroom and a beautifully updated full bath. Take in scenic views of the Battenkill and enjoy the calming sound of flowing water right from your private back deck.Perfectly situated on Barnumville Road, you’re just minutes from all that Manchester has to

  

  Kristin Comeau

  TPW Real Estate

  (802) 613-9625

  1768 Barnumville Rd, Manchester Center, VT 05255
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  /56

  $925,000

  • 3 Beds
  • 4.5 Baths
  • 3,718 Sq Ft

  171 Mending Walls Rd, Manchester Center, VT 05255

  Looking for "NEW"? This is as close to new as any residence can be since it was "gutted to studs" and completely tastefully renovated on three levels! New quartz island kitchen, all new stainless appliances, new soft gray painted cabinetry, and completely open to dining and living areas. The foyer is two stories tile entrance with powder room. Peer through from the foyer, and a spacious vaulted

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 736-7720

  171 Mending Walls Rd, Manchester Center, VT 05255
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  /45

  $565,000

  • 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
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  /28

  $550,000

  • 2 Beds
  • 2 Baths
  • 1,992 Sq Ft

  2936 Hapgood Pond Rd, Peru, VT 05152

  This is Vermont the way it's supposed to feel. Escape the ordinary and settle into something slower. Nestled on 30 private acres in the heart of Vermont's Green Mountains, this charming 2-bedroom, 2-bath cabin is the kind of place where the outside world fades away. Inside you will find a cozy living room with a wood burning fireplace, 2 good sized bedrooms and a bonus room. The lower walk out

  Jamie Wylie Stratton Real Estate

  2936 Hapgood Pond Rd, Peru, VT 05152
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  /13

  $875,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  43 Middle Ridge Rd Unit 209, Winhall, VT 05155

  Beautiful corner three bedroom, two bath condominium in one Stratton Mountain's most desirable neighborhoods. Heated parking garage, with two assigned spaces. Locker room for ski storage. Heated year round pool, hot tubs, sauna for Rising Bear and Hearthstone. Private shuttle to skier drop off area, or walk directly across street. Excellent potential as a rental property. Sold fully furnished.

  John Sikes Stratton Real Estate

  43 Middle Ridge Rd Unit 209, Winhall, VT 05155
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  /10

  $150,000

  • Land
  • 4 Acres
  • $37,500 per Acre

  0 Rocky Ln Unit 5082777, Dorset, VT 05253

  'THE GROUND BENEATH AN APRIL SNOWSTORM IS NOT DORMANT... IT IS AWAKENING!".... Come discover the perfect opportunity to craft the home of your dreams!! With Spring ready to bloom, this very special lot is vibrant and quite ready for your vision!Fully permitted for a five bedroom residence, this property combines privacy, natural beauty and convenience!Imagine waking up to serene views,

  Sunny Breen Josiah Allen Real Estate, Inc.

  0 Rocky Ln Unit 5082777, Dorset, VT 05253
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  /38

  $475,000

  • 4 Beds
  • 2 Baths
  • 1,823 Sq Ft

  49 Limerick Ln, Arlington, VT 05250

  OPEN House Saturday, April 11, 10-12:30!Mountain Views. Battenkill River Access. Effortless Vermont Living.Welcome to this freshly updated 4-bedroom, 2-bath home with new roof set in the heart of the Green Mountains, where comfort meets outdoor beauty. Enjoy stunning mountain views and direct access to the Battenkill River—featuring one of the widest and deepest stretches in the

  

  Margretta Fischer

  Wohler Realty Group

  (802) 278-9802

  49 Limerick Ln, Arlington, VT 05250
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  /49

  $275,000

  • 2 Beds
  • 1 Bath
  • 1,124 Sq Ft

  42 Overlook Rd, Pownal, VT 05261

  Tucked away in a rural setting, this 2 bedroom, 1 bath, ranch style home offers spectacular views overlooking Barber Pond. Inside, you’ll find a warm and inviting cabin style interior, complete with natural wood accents and a Vermont Castings wood stove set on a stunning stone hearth for cozy ambiance during the colder seasons. The galley style, eat-in kitchen has rustic cabinetry, water views, a

  Casey Scott Southern Vermont Realty Group

  42 Overlook Rd, Pownal, VT 05261
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  /34

  $579,000

  • 3 Beds
  • 2 Baths
  • 1,455 Sq Ft

  4 Pearl Buck Dr, Winhall, VT 05340

  Just minutes from the slopes of Stratton Mountain Resort, this three bedroom plus den, two bath home offers an easy four season retreat with stunning views of Stratton Mountain. Set on 2 acres, it gives you convenient access to everything the area is known for, from winter ski days to summer mountain biking, golf, hiking, and village events. The home has been thoughtfully improved over time,

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  4 Pearl Buck Dr, Winhall, VT 05340
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  /34

  $259,000

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  1808 East Rd, Bennington, VT 05201

  Well-maintained 3-bedroom, 1-bath ranch set on a beautifully landscaped half-acre in Bennington. This inviting home offers easy single-level living with a bright picture window framing peaceful views, an attached heated two-car garage, and a convenient shed for additional storage. Pride of ownership is evident throughout, with solid systems and thoughtful care over the years, while offering an

  Abi Gregorio

  1808 East Rd, Bennington, VT 05201
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  /37

  $525,000

  • 3 Beds
  • 3 Baths
  • 3,182 Sq Ft

  4 Stonehedge Dr, Bennington, VT 05201

  Beautiful 3-bedroom, 3-bath home offering stunning views from a spacious two-tier deck-perfect for relaxing or entertaining. Designed for comfortable main-level living, the home features a generous primary suite and an open, light-filled living room with a dramatic wall of windows that captures the surrounding scenery. Warm and inviting, the home includes two gas fireplaces, gleaming wood floors,

  Kelley Mccarthy Mahar McCarthy Real Estate

  4 Stonehedge Dr, Bennington, VT 05201
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  /59

  $3,475,000

  • 5 Beds
  • 4.5 Baths
  • 5,905 Sq Ft

  220 Camptown Rd, Manchester Center, VT 05255

  Set high on a hillside overlooking a picturesque horse farm, this exceptional Manchester property captures far-reaching mountain views and covetous privacy. Nearly 39 acres of sweeping lawn and open meadow transition into wooded terrain, with direct access to over 1,000 acres of conserved land leading to Mount Equinox and Myrick Mountain in the Equinox Highlands. Trails on the property and

  Christiane Carroccio TPW Real Estate

  220 Camptown Rd, Manchester Center, VT 05255
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  /55

  $975,000

  • 4 Beds
  • 4 Baths
  • 4,184 Sq Ft

  520 Moose Hollow Rd, Winhall, VT 05340

  This custom-built contemporary home was designed with large gatherings of family and friends in mind, offering a spacious layout and plenty of room to relax and entertain. You can’t beat the location - just minutes to Manchester, Bromley, and Stratton, and nestled in the heart of year-round recreation. The private setting has views of Bromley’s trails and is bordered by the National Forest. This

  Karin Hardy Berkshire Hathaway HomeServices Stratton Home

  520 Moose Hollow Rd, Winhall, VT 05340
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  /48

  $3,285,000

  • 5 Beds
  • 6 Baths
  • 6,900 Sq Ft

  68 Green Peak Orchard S, East Dorset, VT 05253

  Located in the desirable Green Peak Orchard, this exceptional custom Greek Revival residence is set on 9.9 private acres surrounded by mature landscaping, stone walls, and terraces. Thoughtfully designed with timeless craftsmanship, the home features wide-plank floors, hand-plastered walls and ceilings, custom moldings, historic reproduction lighting, and finely crafted wainscoting and cabinetry.

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

  68 Green Peak Orchard S, East Dorset, VT 05253
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  /32

  $275,000

  • 1,680 Sq Ft

  318 North St, Bennington, VT 05201

  Versatile mixed-use property with strong potential as a duplex or owner-occupied investment in a highly visible downtown North Street location. Currently configured with a beautifully renovated 1-bedroom, 1-bath apartment on the second floor and a spacious first-floor commercial unit, this property offers multiple paths for income and future use. Zoning supports multi-family, single-family, and a

  Jenifer Prouty Hoffman Hoffman Real Estate

  318 North St, Bennington, VT 05201
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  /40

  $795,000

  • 6 Beds
  • 5 Baths
  • 5,689 Sq Ft

  2677 Route 30, Dorset, VT 05251

  Step into the timeless charm of this beautifully preserved Dorset farmhouse, where historic character meets the ease of modern living. Set on 1.79 scenic acres with sweeping mountain views, this inviting six-bedroom home with additional apartment offers space, flexibility, and classic Vermont appeal.A bright and welcoming mudroom greets you upon entry, featuring wide-plank original flooring,

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  2677 Route 30, Dorset, VT 05251
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  /29

  $1,200,000

  • 1 Bath
  • 950 Sq Ft

  109 Winhall Hollow Rd, Winhall, VT 05340

  Experience the pinnacle of Green Mountain living on this extraordinary 23.5-acre property. Perfectly positioned to capture a stunning, direct-line-of-sight view of Stratton Mountain, this property is more than just a home—it is a private outdoor sanctuary meticulously designed by The Wadsworth Company for the modern adventurer. The centerpiece of the property is a striking, contemporary dwelling

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  109 Winhall Hollow Rd, Winhall, VT 05340
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  /40

  $289,000

  • 6 Beds
  • 4 Baths
  • 2,520 Sq Ft

  111 Booth Terrace, Bennington, VT 05201

  Exceptional opportunity to own a beautifully maintained duplex in the heart of Bennington. Each spacious unit offers 3BR and 1.5BA, featuring warm wood floors, generous living space, and thoughtful layouts that appeal to both tenants and owner-occupants alike. Renovated and updated through the years, the property has been meticulously cared for and has an organized, efficient setup throughout.

  Abi Gregorio

  111 Booth Terrace, Bennington, VT 05201
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  /7

  $997,000

  • Land
  • 0.53 Acre
  • $1,881,132 per Acre

  153 Northside Dr, Bennington, VT 05201

  Level, .53-acre lot situated in Bennington’s high-traffic Planned Commercial (PC) District. This site offers a rare opportunity to save significantly on demolition costs and move straight into the design and permitting phase for a new commercial project. This busy corridor lot is located entirely outside of the flood zone, providing a clean slate for development and a more streamlined path for

  Lori Hurley Four Corner Properties LLC

  153 Northside Dr, Bennington, VT 05201
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  /12

  $865,000

  • 12 Beds
  • 8 Baths
  • 5,568 Sq Ft

  1931 Vermont Route 67 E, Shaftsbury, VT 05262

  Rare investment opportunity in one of the area’s most desirable neighborhoods! This unique offering includes two historic buildings set on a spacious 1-acre lot, featuring a total of 8 well-maintained units—comprised of (4) two-bedroom apartments and (4) one-bedroom apartments. Each building offers shared covered front porches, perfect for enjoying the charm of this pleasant street setting. The

  Julie Glover Mahar McCarthy Real Estate

  1931 Vermont Route 67 E, Shaftsbury, VT 05262
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  /37

  $629,000

  • 5 Beds
  • 2 Baths
  • 2,050 Sq Ft

  1649 E Manchester Rd, Manchester Center, VT 05255

  The most desirable homes are the ones that feel both beautifully removed and effortlessly connected. Privately set just moments from Manchester's boutiques, dining, and year-round recreation, this five bedroom, two bath Cape offers a rare sense of ease, pairing a peaceful setting with exceptional proximity to town. Thoughtfully updated and move-in ready, the home is as inviting as it is

  Hayleyanne Van Der Kar Four Seasons Sotheby's Int'l Realty

  1649 E Manchester Rd, Manchester Center, VT 05255
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  /60

  $1,600,000

  • 5 Beds
  • 4.5 Baths
  • 4,243 Sq Ft

  397 Fern Hill, Dorset, VT 05251

  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 forest. The entire

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 347-9044

  397 Fern Hill, Dorset, VT 05251
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  /13

  $295,000

  • 4 Beds
  • 2 Baths
  • 2,022 Sq Ft

  124 S Branch St, Bennington, VT 05201

  Don’t miss this two-family gem! Each spacious unit features 2 bedrooms, eat-in kitchen, large living room with hardwood floors and tin ceiling throughout, spacious full bathroom, and in-unit laundry hookups—perfect for comfortable living or strong rental potential. The downstairs unit offers a side porch for sitting and both units get to enjoy a charming covered front porch on a side street. With

  Julie Glover Mahar McCarthy Real Estate

  124 S Branch St, Bennington, VT 05201
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  /9

  $295,000

  • 4 Beds
  • 2 Baths
  • 2,206 Sq Ft

  116 S Branch St Unit 118, Bennington, VT 05201

  Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car

  Julie Glover Mahar McCarthy Real Estate

  116 S Branch St Unit 118, Bennington, VT 05201
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  /23

  $90,000

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  15 Blake Dr, Pownal, VT 05261

  Brand-new construction! Excellent opportunity to get affordable housing in Southern Vermont. 2 bedrooms and 2 bathrooms. Full kitchen with dishwasher. Short drive to Bennington, VT or North Adams, MA, 1 hour or so to Albany. Act quick, properties like these sell fast!

  Zachary Zupan EXP Realty

  15 Blake Dr, Pownal, VT 05261
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  /12

  $239,995

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  240 Church St, Shaftsbury, VT 05262

  Ready for its next owner! This charming home offers a great opportunity for anyone looking to put their personal touch on a property with tons of potential. Sitting on an acre-sized lot, there’s plenty of room to expand. Inside, the home needs some TLC—but that’s where the value lies. With the right updates, you can truly bring your vision to life. The layout also provides potential for an in-law

  Derek Greene Derek Greene

  240 Church St, Shaftsbury, VT 05262
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  /44

  $815,000

  • 4 Beds
  • 4.5 Baths
  • 2,980 Sq Ft

  74 Pond View Rd, Winhall, VT 05340

  This spacious and well-maintained 4-bedroom, 4.5-bathroom condo in Stratton’s desirable Intervale community offers nearly 3,000 square feet of comfortable mountain living, just minutes from the Base Lodge with winter shuttle service. Nestled among the trees for added privacy, the home features an open-concept main level with cathedral ceilings, abundant natural light, a wood-burning fireplace,

  Christine Chovan

  74 Pond View Rd, Winhall, VT 05340
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  /44

  $199,000

  • 2 Beds
  • 2.5 Baths
  • 1,156 Sq Ft

  106 Park St Unit 2, Bennington, VT 05201

  Freshly updated 2-story townhouse in a convenient downtown Bennington location! This 2BR home features brand new stainless steel appliances, new vinyl plank flooring, and a fresh interior paint palette throughout. The open-concept main level offers a bright kitchen, dining, and living area—perfect for everyday living and entertaining—along with a pantry, half bath, and dedicated laundry room for

  Vicki Wilson Maple Leaf Realty

  106 Park St Unit 2, Bennington, VT 05201
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  /60

  $220,000

  • Land
  • 54 Acres
  • $4,074 per Acre

  399 Bard Rd, Bennington, VT 05201

  Escape to your own private sanctuary on this sprawling 54+/- acre wooded retreat in beautiful Bennington, VT. Nestled among a lush mix of hard and softwoods teeming with wildlife, the property features a charming quarter-acre pond situated entirely within its southeastern boundary, perfect as a future homestead centerpiece. Enjoy easy access via a paved, town-maintained road leading to level

  Curtis Trousdale Preferred Properties

  399 Bard Rd, Bennington, VT 05201
• 

  

  /23

  $349,900

  • 4 Beds
  • 2 Baths
  • 2,030 Sq Ft

  773 Oberdorf Rd, Readsboro, VT 05350

  Discover cozy mountain living in this charming Alpenwald chalet, where rustic character meets thoughtful modern updates. Nestled among the trees, this inviting retreat offers a bright, open floor plan filled with natural light from expansive windows and sliding glass doors. Recently remodeled, the kitchen and both full bathrooms bring a fresh, updated feel, while a comfortable bar area adds the

  Sean Taylor Moresi Real Estate Partners

  773 Oberdorf Rd, Readsboro, VT 05350
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  /12

  $299,999

  • Land
  • 10.05 Acres
  • $29,851 per Acre

  00 Garden Loop Rd, Winhall, VT 05340

  The largest remaining vacant lot on the Stratton Mountain access road. Ten acres deeded for one magnificent home. The lot is wooded with some clearing on the east side. There's a roughed-in driveway here too, making it the best spot for construction. In the center of the property is a small pond--about a tenth of an acre--and west of that a scenic perennial creek winds its way downhill along the

  David White OwnerEntry.com

  00 Garden Loop Rd, Winhall, VT 05340
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  /48

  $780,000

  • 4 Beds
  • 5 Baths
  • 3,423 Sq Ft

  85 Limerick Ln, Arlington, VT 05250

  Vermont lifestyle meets income potential! Set in the scenic Taconic and Green Mountain valley along the Battenkill River, this spacious 4-bedroom, 5-bath home, built in 2001, offers peaceful country living with versatile use. The property features three living sections with separate entrances, each with at least one 3⁄4 bath—ideal for multi-generational living, guests, or rental opportunities.

  

  Margretta Fischer

  Wohler Realty Group

  (802) 500-7734

  85 Limerick Ln, Arlington, VT 05250
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  /33

  $649,000

  • 3 Beds
  • 3 Baths
  • 1,650 Sq Ft

  39 Pond View Rd Unit 39, Winhall, VT 05340

  Set in a prime location along Stratton Access Road, this Intervale townhouse offers an easygoing mountain lifestyle with everything you need close at hand—including weekend and holiday winter shuttle service to the base lodge. The 3-bedroom + loft, 3-bath layout provides plenty of space for guests, while the open living area brings everyone together with a seamless flow between the kitchen,

  Carrie Mathews Winhall Real Estate

  39 Pond View Rd Unit 39, Winhall, VT 05340
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  /5

  $350,000 New Construction

  • 2 Beds
  • 2 Baths
  • 1,190 Sq Ft

  525 Jennings Brook Dr, Bennington, VT 05201

  Brand new 2026 construction offering the ease of single-level living with thoughtful, ADA-compliant design throughout. This energy-efficient home features 2 bedrooms and 2 full bathrooms, including a well-designed primary suite, plus convenient in-unit laundry. The open-concept layout is highlighted by a spacious kitchen and a cathedral ceiling that brings in abundant natural light and an airy

  Lilli West Maple Leaf Realty

  525 Jennings Brook Dr, Bennington, VT 05201
• 

  

  /17

  $159,900

  • 2 Beds
  • 1.5 Baths
  • 852 Sq Ft

  432 South St Unit B2, Bennington, VT 05201

  Updated and ready to go. This 2 bedroom upstairs condo is perfect for those who don't want to rent, would like to build equity and would like low maintenance. A corner unit with great light and being upstairs means no neighbors overhead. 2 bedrooms, 2 bathrooms (one 3/4 and one half bath). With rents in the area rising this is a great option for most!

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  432 South St Unit B2, Bennington, VT 05201
• 

  

  /4

  $18,000

  • Land
  • 1.1 Acres
  • $16,364 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 1-acre lot offers the perfect blend of privacy and convenience. Power is available at the road. Whether you're seeking a peaceful retreat or a year-round residence, this spacious lot provides ample room for gardens, recreation, and more, all within a welcoming mountain community. Don't miss this opportunity to own a

  Colt Hazell Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350

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