Bennington County VT Homes for Sale

• 

  

  

  /19

  $310,000

  $15K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,199 Sq Ft

  80 Murray Hill South Rd Unit 13, Manchester, VT 05255

  Imagine yourself enjoying all that Manchester has to offer in this 2-bedroom, 2.5-bath condominium, ready for its new owner.The inviting open living room features a soaring cathedral ceiling and a cozy wood-burning fireplace, creating the perfect space for relaxing or entertaining. The spacious kitchen offers plenty of room for cooking and gathering with family and friends.Conveniently

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  80 Murray Hill South Rd Unit 13, Manchester, VT 05255
• 

  

  

  /37

  $549,900

  • 4 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  811 Middle Pownal Rd, Bennington, VT 05201

  Thoughtfully crafted with a distinctive European-inspired character and beautifully updated throughout, this custom-built 4-bedroom, 3-bath home offers the perfect blend of quality craftsmanship, privacy, and convenience on a picturesque, landscaped lot just minutes from downtown Bennington. The bright and inviting interior features a beautifully renovated kitchen, spacious living areas with

  Jeffrey Dorman

  811 Middle Pownal Rd, Bennington, VT 05201
• 

  

  

  /14

  $125,000

  • 3 Beds
  • 1 Bath
  • 768 Sq Ft

  347 Hickory Rd, Bennington, VT 05201

  Your wait is over—an exceptional opportunity to own in the highly sought-after Woodford Lake Estates! This unique property offers direct access to the beauty of the surrounding Green Mountain National Forest and is ideally located near VAST snowmobile trails, making it a year-round haven for outdoor enthusiasts. Enjoy cross-country skiing just minutes away at Prospect Mountain, along with beach

  Faith Rhodes Maple Leaf Real Estate

  347 Hickory Rd, Bennington, VT 05201
• 

  

  

  /20

  $495,000

  $105K PRICE DROP

  • Land
  • 28 Acres
  • $17,679 per Acre

  00 Vermont 11, Peru, VT 05152

  Sweeping views of Stratton, Bromley, and Magic Mountains define this 28 +/- acre offering in Peru, Vermont, where rare east, south, and westerly exposure provides exceptional natural light and solar orientation throughout the day. The surrounding landscape combines open mountain vistas, varied terrain, and connection to the Green Mountains in a setting shaped by Southern Vermont’s four-season

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  00 Vermont 11, Peru, VT 05152
• 

  

  

  /38

  $1,795,000

  $80K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,370 Sq Ft

  1310 Dorset Hill Rd, East Dorset, VT 05253

  Perched on the side of Mount Aeolus and conveniently located near Manchester, this exceptional 4-bedroom, 3-bath contemporary retreat offers privacy, sophistication, and year-round natural beauty across 21 picturesque acres. Thoughtfully designed to embrace its surroundings, the property features rolling meadows, mature woodland, vibrant perennial gardens, and sweeping views of the Green

  Annette Gallo Real Broker LLC

  1310 Dorset Hill Rd, East Dorset, VT 05253
• 

  

  /59

  $210,000

  • 5 Beds
  • 2 Baths
  • 2,200 Sq Ft

  118 Foster Dr, Bennington, VT 05201

  Set on over 5.5 acres of private, natural surroundings, this unique split-level ranch with an auxiliary dwelling unit offers an exceptional opportunity for multi-generational living, rental income, or a private guest retreat. Surrounded by peaceful woodlands, the property provides a tranquil rural setting while remaining just a short drive from town amenities.The main residence features three

  Lindsey Martin Maple Leaf Real Estate

  118 Foster Dr, Bennington, VT 05201
• 

  /2

  $65,000

  • Land
  • 17.3 Acres
  • $3,757 per Acre

  0 Hidden Valley Rd Unit 5055076, Shaftsbury, VT 05262

  Ready to build 17 acer lot with wastewater permit for a 4 bedroom single family residence. Great potential for a pond site and the trails on the lot make it a great opportunity for a horse paddock.

  Dan Mason Perrott Realty

  0 Hidden Valley Rd Unit 5055076, Shaftsbury, VT 05262
• 

  

  /25

  $1,425,000

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

  1058 Granger Hollow Rd, North Bennington, VT 05257

  A private Vermont sanctuary set on over 40 acres of meadows, rolling hills, stone walls, and mature forest. This sophisticated modern farmhouse offers rare peace, privacy, and natural beauty, and sweeping seasonal views from every room.Designed to blend seamlessly into the land, the light-filled home features expansive Marvin windows and refined custom finishes throughout. The chef’s kitchen

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  1058 Granger Hollow Rd, North Bennington, VT 05257
• 

  

  /25

  $1,997,000

  • 4 Beds
  • 2.5 Baths
  • 4,125 Sq Ft

  655 Squirrel Hollow Rd, East Dorset, VT 05253

  Set on 23 private acres with sweeping Green Mountain views, this contemporary residence by acclaimed architect Jeff Barnes is thoughtfully composed to engage its landscape at every turn. Walls of glass, soaring ceilings, exposed timber trusses, and stone fireplaces bring scale and warmth to the interiors, while broad windows draw in light and long views from nearly every principal room.

  Laura Kottler LandVest, Inc/Woodstock

  655 Squirrel Hollow Rd, East Dorset, VT 05253
• 

  

  /5

  $375,000

  $90K PRICE DROP

  • Land
  • 5.54 Acres
  • $67,690 per Acre

  Lot #4 Margeaux Ln, Stratton, VT 05155

  Nestled along a peaceful babbling brook, this 5.54-acre parcel offers an idyllic setting for building the home of your dreams. Surrounded by a serene wooded landscape, the property provides both privacy and tranquility, while still being just moments from the Sun Bowl at Stratton. With a septic permit already approved for a 4-bedroom home, this lot is ready for construction, allowing you to begin

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  Lot #4 Margeaux Ln, Stratton, VT 05155
• 

  

  /52

  $88,800

  $10K PRICE DROP

  • 1 Bed
  • 586 Sq Ft

  845 Bailey Hill Rd, Readsboro, VT 05350

  Wonderful little getaway for some ''EZ'' living—be one with nature with all the essentials in place! It’s common to see wildlife in this rural setting, making it perfect to create your ideal Vermont retreat. Nestled among the trees, you’ll relish the peaceful ambiance and natural beauty that surrounds you, offering a true sense of escape from the everyday hustle. A tidy, compact getaway with a

  Dan Mason Perrott Realty

  845 Bailey Hill Rd, Readsboro, VT 05350
• 

  

  /55

  $995,000

  • 4 Beds
  • 5.5 Baths
  • 4,502 Sq Ft

  3373 Main St, Manchester, VT 05254

  In the heart of Manchester Village, this four-bedroom, six-bath colonial blends classic New England charm with the kind of space and flexibility that fits modern living. Set on a level 0.85-acre lot with mountain views, the property offers both privacy and easy access to everything the village has to offer. Inside, you'll find character you can't replicate - spruce and pine floors, exposed beams,

  David Halligan Four Seasons Sotheby's Int'l Realty

  3373 Main St, Manchester, VT 05254
• 

  

  /59

  $979,000

  • 4 Beds
  • 3.5 Baths
  • 5,248 Sq Ft

  41-43 Cranberry Hill Rd, Winhall, VT 05340

  This is the ultimate modern Alpine chalet, fully renovated yet boasting the classic flat-sawn balusters characteristic of mountain homes in the Alps. Three expansive floors offer sunny, well-appointed space, beginning with a roomy mudroom, three bedrooms and two bathrooms (one en-suite). Head upstairs to join your friends and family in the open-concept European kitchen/living/dining room with

  Jamie Luke TPW Real Estate

  41-43 Cranberry Hill Rd, Winhall, VT 05340
• 

  

  /22

  $1,425,000

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

  B Prospect St, Manchester, VT 05254

  A rare opportunity to own 38 stunning acres in the heart of Manchester Village, offering the perfect balance of seclusion, natural beauty, and convenience. A long, winding serpentine driveway gracefully leads to a beautifully manicured and ready-to-build homesite, creating a dramatic and private approach. Thoughtfully improved with underground power brought directly to the building site, a well,

  Sunny Breen Josiah Allen Real Estate, Inc.

  B Prospect St, Manchester, VT 05254
• 

  

  /40

  $720,000

  $15K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,317 Sq Ft

  B2 Maple Ridge Rd, Winhall, VT 05155

  The Highgate Piper Ridge Townhome is ideally located just a short stroll from the exclusive sports center and provides convenient shuttle service to Stratton’s ski lifts during the winter season. This residence is filled with natural light and features a contemporary kitchen and bathrooms, polished hardwood floors, and elegant tile accents throughout. The one-car garage has been ingeniously

  Mike England Michael England Real Estate

  B2 Maple Ridge Rd, Winhall, VT 05155
• 

  

  /60

  $1,495,000

  • 4 Beds
  • 3.5 Baths
  • 4,023 Sq Ft

  1268 Myers Rd, Shaftsbury, VT 05262

  Welcome to your paradise! This exquisite 30 acre estate offers extreme privacy, a custom home with architectural details throughout, a modern 1 BR guest apartment, an oversized 2 car garage, top notch equestrian facilities, a trout pond, playhouse and the list goes on and on. The winding driveway leads one to an enchanting compound, as it opens to overlook the exclusive estate in all of it's

  Laura Beckwith Josiah Allen Real Estate, Inc.

  1268 Myers Rd, Shaftsbury, VT 05262
• 

  

  /45

  $380,000

  • 2 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  553 Roaring Branch Rd, Arlington, VT 05250

  Welcome to Beaver Cabin! Perched upon a bluff overlooking the renown Battenkill River, the Roaring Branch community of log cabins is a much coveted getaway in the Green Mountains of Vermont. Tucked within the forest with trails and access down to the riverside, you'll enjoy the privacy and solitude of being quietly situated among the trees with the calming sound of the flowing Battenkill. Whether

  Kim Morgan-Wohler Wohler Realty Group

  553 Roaring Branch Rd, Arlington, VT 05250
• 

  

  /6

  $395,000

  $100K PRICE DROP

  • Land
  • 6.93 Acres
  • $56,999 per Acre

  lot#2 Margeaux Ln, Stratton, VT 05155

  This stunning 6.93-acre parcel offers the perfect setting to build the home of your dreams, just moments from the Sun Bowl at Stratton. Nestled in a serene wooded landscape, the property provides both privacy and tranquility while being ideally located for easy access to all that Stratton has to offer. With a septic permit already approved for a 4-bedroom home, this lot is ready for you to begin

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  lot#2 Margeaux Ln, Stratton, VT 05155
• 

  

  /15

  $99,500

  • Land
  • 1.2 Acres
  • $82,917 per Acre

  23 Moose Hollow Rd, Winhall, VT 05340

  Beautiful parcel located in a highly desirable Winhall neighborhood, just minutes to Bromley and Stratton Mountains, and a short drive to Manchester’s shops and dining. This property offers a State of Vermont potable water supply and wastewater permit in place for a 4-bedroom home. The lot is cleared and ready for construction—an ideal opportunity to build your Vermont retreat.

  Carrie Mathews Winhall Real Estate

  23 Moose Hollow Rd, Winhall, VT 05340
• 

  

  /32

  $750,000

  $45K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,696 Sq Ft

  130 Ipan Rd, North Bennington, VT 05257

  Tucked away on a private road, this stunning brick colonial offers over 30 acres of peaceful Vermont countryside-yet is less than 2 miles from the Village of North Bennington and Bennington College. A classic barn and separate studio provide endless possibilities for hobbies, storage, or creative space. The main level features a spacious living room with a fireplace, warm pine floors, and plenty

  Kelley Mccarthy Mahar McCarthy Real Estate

  130 Ipan Rd, North Bennington, VT 05257
• 

  

  /60

  $1,450,000

  $45K PRICE DROP

  • 6 Beds
  • 5.5 Baths
  • 4,864 Sq Ft

  557 Bennett Hill Rd, Shaftsbury, VT 05262

  Gorgeous, renovated Colonial offering exceptional flexibility, thoughtful design, and timeless charm. This beautifully updated property features a spacious main residence along with a stunning addition that includes a full in-law suite and a private studio above ideal for guests, extended family, a home office, or potential rental income. Solar panels installed above the garage power efficient

  Kelley Mccarthy Mahar McCarthy Real Estate

  557 Bennett Hill Rd, Shaftsbury, VT 05262
• 

  

  /14

  $649,000

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft

  792 Stratton Mtn Access Rd Unit 4310, Stratton, VT 05155

  Imagine Friday evening: you pull through the private gate, the tires of your car crunching over the paved lot, and you find that perfect spot right near the entrance. As you turn off the engine, a quiet stillness settles in. You won’t be reaching for those keys again until Monday.Welcome to your retreat at Village Watch. The ArrivalStep inside the dedicated mudroom, where there’s a place

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  792 Stratton Mtn Access Rd Unit 4310, Stratton, VT 05155
• 

  

  /52

  $5,600,000

  • 5 Beds
  • 5.5 Baths
  • 4,674 Sq Ft

  1060 Upper Hollow Rd, Dorset, VT 05251

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

  Sunny Breen Josiah Allen Real Estate, Inc.

  1060 Upper Hollow Rd, Dorset, VT 05251
• 

  

  /6

  $199,900

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  631 Oberdorf Rd, Readsboro, VT 05350

  Bring your vision and transform this 3-bedroom, 2-bathroom home into the Vermont getaway you've always wanted. Located in the private Alpenwald Village community, this fixer-upper offers a fantastic opportunity for investors, vacation home buyers, or anyone looking to build equity in a scenic mountain setting.Surrounded by the Green Mountain National Forest, the property provides direct

  Kristen Breeden Southern Vermont Realty Group

  631 Oberdorf Rd, Readsboro, VT 05350
• 

  

  /50

  $775,000

  • 4 Beds
  • 2.5 Baths
  • 2,220 Sq Ft

  392 Powderhorn Rd, Manchester Center, VT 05255

  Set on two private acres in a desirable Manchester location, this renovated four-bedroom, three-bath Colonial balances privacy and convenience with easy access to both Manchester and Dorset. Wide-plank pine floors, abundant natural light, and inviting living spaces define the interiors. The main level features a spacious living room anchored by a stone fireplace, a formal dining room, and an

  Alexandra Crowley Four Seasons Sotheby's Int'l Realty

  392 Powderhorn Rd, Manchester Center, VT 05255
• 

  

  /12

  $95,000

  • Land
  • 1 Acre
  • $95,000 per Acre

  41 Moose Hollow Rd, Winhall, VT 05340

  Build your dream home on this ready-to-go 1-acre lot in the Green Mountains. Located on a private gravel road in Winhall, this mostly cleared parcel offers a gentle slope, power at the road, a nearby stream, and a state-issued 4-bedroom septic permit already in place. The setting provides a peaceful, natural feel while keeping you close to the best of Southern Vermont. Bromley Mountain is about

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  41 Moose Hollow Rd, Winhall, VT 05340
• 

  

  /36

  $219,000

  • 2 Beds
  • 1 Bath
  • 753 Sq Ft

  16 Old Farm Rd Unit 4, Winhall, VT 05340

  Tucked into the Old Farm community in Winhall, this inviting condominium offers classic Vermont character with the ease of association living. The main building has pre-1900 roots, with later additions that help create a warm and practical mountain-town retreat. A hydronic electric baseboard heating system, replaced when the current owners purchased the property, is complemented by a pellet stove

  Trent Stephens Wohler Realty Group

  16 Old Farm Rd Unit 4, Winhall, VT 05340
• 

  

  /37

  $399,000

  $31K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,663 Sq Ft

  446 Highland Ave, Manchester Center, VT 05255

  Looking for a unique opportunity for equity growth? This is it! Location, location, location. Highly desirable Highland Avenue is one of those rare streets with character homes that is literally only a few walking blocks to town. If you are lucky enough to own this charming 3- bedroom home offering 1,663 sq ft of living space, you will enjoy easy access to the library, local shops, coffee spots,

  Sunny Breen Josiah Allen Real Estate, Inc.

  446 Highland Ave, Manchester Center, VT 05255
• 

  

  /54

  $1,990,000

  • 6 Beds
  • 6.5 Baths
  • 5,896 Sq Ft

  27 Mountain View Rd, Winhall, VT 05360

  Direct views of Stratton Mountain set the stage for this exceptional post-and-beam residence, offering a rare combination of luxury living, entertaining space, and rental flexibility. Handcrafted timber framing creates warmth and character throughout, while four fireplaces including a gas fireplace in the primary suite enhance the home's mountain atmosphere. Designed for gathering, the lower

  Jamie Wylie Stratton Real Estate

  27 Mountain View Rd, Winhall, VT 05360
• 

  

  /3

  $74,900

  • Land
  • 2.25 Acres
  • $33,289 per Acre

  0 Brambley Ln, Bennington, VT 05201

  Expansive 2.25-acre level lot situated on a quiet, private dead-end street. This is an amazing opportunity to build a dream home, a weekend retreat, or a spec house for investment. The property features 306 feet of road frontage, has been perc tested, and includes septic plans for a three-bedroom system. Located on the outskirt of town, but still close proximity to historic downtown Bennington

  Matt Waddington Hoffman Real Estate

  0 Brambley Ln, Bennington, VT 05201
• 

  

  /47

  $1,225,000

  • 4 Beds
  • 3 Baths
  • 3,357 Sq Ft

  153 High Meadow Rd, Winhall, VT 05340

  Located in Stratton Resort’s sought-after High Meadow community, this beautifully maintained and turnkey home offers the perfect blend of comfort, convenience, and mountain charm. Filled with natural light, the home features four bedrooms and three recently updated full baths, along with hardwood floors, cathedral ceilings, skylights, and a stunning floor-to-ceiling brick fireplace. Recent

  Britt Wohler

  153 High Meadow Rd, Winhall, VT 05340
• 

  

  /41

  $429,000

  • 2 Beds
  • 2 Baths
  • 6,686 Sq Ft

  3310 Vt Route 346, Pownal, VT 05261

  Paul Harsch Harsch Associates

  3310 Vt Route 346, Pownal, VT 05261
• 

  

  /57

  $899,000

  • 4 Beds
  • 3 Baths
  • 4,112 Sq Ft

  2572 Morse Hill Rd, Dorset, VT 05251

  Set along the rise of Morse Hill Road, this Dorset home has the quiet gravity of a place that feels discovered rather than merely shown. It carries the attributes buyers most often hope to find here: privacy, scale, high ceilings, fireplaces, a substantial bedroom count, ski access, village proximity, and a layered mountain outlook beyond the road, where the ridgeline appears through the trees

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

  2572 Morse Hill Rd, Dorset, VT 05251
• 

  

  /3

  $475,000

  • Land
  • 12.82 Acres
  • $37,051 per Acre

  22 Morse Rd, Bennington, VT 05201

  Positioned in the heart of Bennington’s commercial corridor on 12.82 open acres, 22 Morse Road present a prime development opportunity. Offering excellent visibility and accessibility along one of the area’s primary commercial arteries, the property is ideally situated for a variety of commercial, retail, service, mixed-use, or redevelopment possibilities. The location provides convenient access

  Paul Carroccio TPW Real Estate

  22 Morse Rd, Bennington, VT 05201
• 

  

  /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
• 

  

  /34

  $125,000

  • Land
  • 2.9 Acres
  • $43,103 per Acre

  311 Beechwood Ln, Peru, VT 05152

  This lovely, nearly 3 acre parcel of land is located on Beechwood Lane, about 1 mile from the Town center of Peru. There is approximately 353' frontage on Beechwood Lane and approximately 271' frontage on Beechnut Drive. The land is gently sloped and nicely wooded for privacy. Xfinity high speed internet available. Peru features the J.J. Hapgood General store, Peru Congregational Church, Hapgood

  Dylan Gage Bromley Real Estate

  311 Beechwood Ln, Peru, VT 05152
• 

  

  /34

  $875,000

  • 4 Beds
  • 2.5 Baths
  • 2,746 Sq Ft

  2436 Mad Tom Rd, East Dorset, VT 05253

  Picture yourself on 12 private wooded acres along one of Vermont's most scenic country roads in a classic 4-bedroom, 3-bath Colonial offering the perfect blend of comfort, character, and outdoor adventure. Built in 1977 and thoughtfully maintained, the home welcomes you with warm hardwood floors, a beautifully renovated kitchen featuring soapstone countertops, abundant cabinetry, and a sunny

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  2436 Mad Tom Rd, East Dorset, VT 05253
• 

  

  /43

  $1,495,000

  • 4 Beds
  • 4.5 Baths
  • 5,170 Sq Ft

  50 Grouse Ln, Dorset, VT 05251

  Custom-built Dorset Hollow estate offered for the first time since 1998. Perfectly situated on 10 private acres abutting 3,200 acres of conservation land, this 5,100 sq ft residence combines timeless quality, fine finishes, and Vermont mountain charm. Designed for comfort and entertaining, the home features 4 bedrooms, 5 bathrooms, and an attached 2-car garage. Elegant details include four

  David Halligan Four Seasons Sotheby's Int'l Realty

  50 Grouse Ln, Dorset, VT 05251
• 

  

  /22

  $579,000

  • 3 Beds
  • 1.5 Baths
  • 2,048 Sq Ft

  560 New Ireland Rd, Manchester Center, VT 05255

  This charming two-story Colonial in Manchester offers a comfortable and functional layout with plenty of living space. The first floor features a kitchen with a wood burning fireplace, along with dining and living areas perfect for everyday living and entertaining. A mudroom provides convenient access to the attached garage. Upstairs, you’ll find three additional rooms offering flexibility for

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  560 New Ireland Rd, Manchester Center, VT 05255
• 

  

  /49

  $1,450,000

  • 5 Beds
  • 4.5 Baths
  • 4,376 Sq Ft

  39 Eagle Ridge, Dorset, VT 05251

  5.7 beautiful acres just off of Morse Hill Road where the southern exposures are to behold, a warm and inviting modern designed residence, post and beam barn and sweeping mountain views await your attention! The 5 Bedroom mostly ensuite house features the grand open concept where living areas are spacious and distinctive areas yet transition beautifully from space to space with newly finished

  Laura Beckwith Josiah Allen Real Estate, Inc.

  39 Eagle Ridge, Dorset, VT 05251

Showing Results 201 - 240, Page 6 of 7