Bennington County VT Homes for Sale

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  /60

  $397,000

  $8K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,729 Sq Ft

  1260 Cider Mill Rd, Shaftsbury, VT 05262

  Tucked away on a peaceful country road in Shaftsbury, this 2-bedroom, 2-bath contemporary ranch offers the perfect balance of privacy and convenience—just 10 minutes to Bennington. Set on 1.5 acres, the home features easy one-level living with an open, light-filled layout. The heart of the home is the bright, sunny kitchen with ample workspace and modern finishes. The spacious primary suite

  Vicki Wilson Maple Leaf Realty

  1260 Cider Mill Rd, Shaftsbury, VT 05262
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  /60

  $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
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  /40

  $735,000

  • 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
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  /37

  $315,000

  • 3 Beds
  • 2 Baths
  • 1,729 Sq Ft

  105 Albe Dr, Bennington, VT 05201

  Tucked into an established and desirable neighborhood, this well-maintained 3-bedroom, 2-bath home offers the kind of easy, low-maintenance living that’s increasingly hard to find. Built in 1999 and thoughtfully designed with comfort and practicality in mind. The layout provides flexibility for a variety of lifestyles with approximately 1,700 square feet of finished living space, generous room

  Jenifer Prouty Hoffman Hoffman Real Estate

  105 Albe Dr, Bennington, VT 05201
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  /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
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  /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
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  /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
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  /10

  $1,950,000

  • Land
  • 7 Acres
  • $278,571 per Acre

  720 N Branch St, Bennington, VT 05201

  Discover the potential at 720 & 702 North Branch Street—a rare 7-acre offering in a prime Bennington location. With level land, generous frontage, and easy access, this property is perfectly positioned for residential or mixed-use development, with municipal water and sewer available at the street. The sale includes a well-maintained duplex at 702 North Branch, featuring a 3-bedroom unit on the

  Paul Carroccio TPW Real Estate

  720 N Branch St, Bennington, VT 05201
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  /60

  $269,000

  • 3 Beds
  • 1.5 Baths
  • 1,934 Sq Ft

  508 Barney Rd, Bennington, VT 05201

  WOW CHECK OUT THIS Country Cutie on the edge of town. The home has been updated while keeping the period Charm. Large level nicely landscaped yard enclosed by hedges. The lager living room has a fireplace with insert and lots of built-ins. The walkout basement has a large room that has been used as a bedroom with a stone fireplace and a half bath in the heated workshop area.The septic was

  Dan Mason Perrott Realty

  508 Barney Rd, Bennington, VT 05201
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  /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
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  /57

  $1,495,000

  • 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
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  /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
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  /60

  $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
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  /12

  $750,000

  • Land
  • 279.97 Acres
  • $2,679 per Acre

  0 Klondike Rd Unit 5085248, Stamford, VT 05352

  Beautiful acreage with mountain views! Roughly 40% open land with the rest wooded. There is a gravity fed pond on the property. Also, the sellers have put 2 cabins on the open part. Each has a kitchenette and a bedroom. A large barn is also on the property and recently had a new floor installed. Very quiet road and perfect for someone looking for a peaceful setting. Timber consists of some sugar

  Michael Jarvis United Country Real Estate Mike Jarvis Group Inc

  0 Klondike Rd Unit 5085248, Stamford, VT 05352
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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

  $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
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  $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
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  /47

  $1,225,000

  Open Sat 12PM - 2PM Coming Soon

  • 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
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  /4

  $29,900

  • Land
  • 1.2 Acres
  • $24,917 per Acre

  270 Bergabhang Dr, Stamford, VT 05352

  Nestled among the trees on a quiet dirt road in Alpenwald Village, this level 1-acre parcel has already been cleared and is ready to build. Fully engineered, it includes state permits for a 3-bedroom home. Enjoy Southern Vermont living near VASA and VAST trails, beautiful rivers, and Harriman Reservoir. Dutch Hill—once a historic ski area—now offers backcountry skiing and hiking. For downhill

  Melissa Nebelski Real Broker LLC

  270 Bergabhang Dr, Stamford, VT 05352
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  /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
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  $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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  /23

  $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
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  /40

  $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
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  /16

  $96,406

  New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  32 Cassie Ln, Bennington, VT 05201

  Welcome to 32 Cassie Lane, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  32 Cassie Ln, Bennington, VT 05201
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  $349,000

  • 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
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  /21

  $249,000

  • Land
  • 3.42 Acres
  • $72,807 per Acre

  0 Havoc Hill Unit 29, Dorset, VT 05253

  Tranquility and Adventure Await on Havoc Hill. Discover 3.42 plus private, wooded acres nestled atop storied Havoc Hill in charming East Dorset, Vermont. Known for its beauty and historic ties to early Vermont logging and farming communities, Havoc Hill offers a rare opportunity to own land rich in character and natural serenity. Set off the picturesque Mad Tom Road, this secluded parcel is fully

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  0 Havoc Hill Unit 29, Dorset, VT 05253
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  /29

  $149,900

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft

  256 Union St, Bennington, VT 05201

  Opportunity awaits in this classic New England-style home conveniently located near downtown Bennington and local amenities. Offering 3 bedrooms, 1 bathroom, spacious living areas, and plenty of natural light throughout, the property features a newer roof, low-maintenance vinyl siding, covered front porch, corner lot location, and off-street parking. Inside, the home offers an eat-in kitchen,

  Jeffrey Dorman

  256 Union St, Bennington, VT 05201
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  /31

  $495,000

  • 7 Beds
  • 4 Baths
  • 2,494 Sq Ft

  190 Cemetery Rd, Arlington, VT 05250

  This is a RARE two lot offering!! It is located on Cemetery Rd in Arlington,VT with quiet, secluded lots. Great opportunity for multi-generational living, guest house, rental income, air bnb, extra space or great resale opportunity. House #1 is a two story house on 2.29 surveyed acres with 4 bedrooms and 1 3⁄4 bathrooms. The living room features a cathedral ceiling with skylights and a wood

  Trent Stephens Wohler Realty Group

  190 Cemetery Rd, Arlington, VT 05250
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  /39

  $359,900

  $10K PRICE DROP

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

  38 Oak Ridge Ln, Bennington, VT 05201

  Convenient one-level living meets modern style and design in this beautifully crafted ranch home, situated on a spacious 1.4-acre lot within a newer, private four-home subdivision. Relax on the impressive 52-foot farmer’s porch—perfect for enjoying cool summer breezes, stunning sunsets, entertaining guests, or simply taking in the expansive yard and thoughtfully designed plantings. Inside the

  Matt Waddington Hoffman Real Estate

  38 Oak Ridge Ln, Bennington, VT 05201
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  /2

  $425,000

  • Land
  • 3 Acres
  • $141,667 per Acre

  lot A Forest Pond Rd, Dorset, VT 05251

  Private Dorset West Road Location... private road... nearby Manchester and Dorset. Ready to build. Waste Water permit in place for 5 BR, 8 person occupancy.

  Charles Mauro Josiah Allen Real Estate, Inc.

  lot A Forest Pond Rd, Dorset, VT 05251
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  /52

  $225,000

  • 3 Beds
  • 1 Bath
  • 1,047 Sq Ft

  99 Coolidge Ave, Bennington, VT 05201

  This cute 3-bedroom, 1-bath cape offers comfortable in-town living with a fully fenced yard and recently renovated kitchen and bath. The laundry hookups are on the first floor which adds everyday convenience. Enjoy morning coffee or evening relaxation in the enclosed 3-season porch with outdoor fenced space perfect for pets, play, or gardening. The upstairs bedroom features unique built-ins that

  Catherine Cairns Maple Leaf Realty

  99 Coolidge Ave, Bennington, VT 05201
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  /46

  $3,000,000

  • 2 Beds
  • 3.5 Baths
  • 5,731 Sq Ft

  2334 Morse Hill Rd, Dorset, VT 05251

  Beautiful Dorset Contemporary Offering Privacy, Comfort, and Easy Living. If you’ve been looking for a private Vermont retreat with room to relax, entertain, and enjoy the beauty of every season, this exceptional custom home may be the perfect fit. Built in 1996 by respected Dorset builder Keith Dodson, this thoughtfully designed 5,731 sq. ft. contemporary sits on 12.15 peaceful acres with a pond

  David Halligan Four Seasons Sotheby's Int'l Realty

  2334 Morse Hill Rd, Dorset, VT 05251
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  /42

  $499,000

  Open Sun 2PM - 4PM Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  366 Kirby Hollow Rd, Dorset, VT 05251

  Set in a premier Dorset country setting with sweeping 360-degree views of rolling pastures, mountains, and neighboring farmland, this charming single-level ranch offers a rare opportunity to enjoy the beauty and tranquility of Southern Vermont. The home offers over 1,568 square feet of comfortable living space, including an open-concept kitchen, dining, and living area, an office, three bedrooms,

  Britt Wohler

  366 Kirby Hollow Rd, Dorset, VT 05251
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  /23

  $235,000

  • 5 Beds
  • 2 Baths
  • 1,860 Sq Ft

  205 County St, Bennington, VT 05201

  This well maintained 2-unit home exceptional flexibility for buyers, allowing for a variety of living arrangements to suit your needs. Whether you choose to enjoy it as a spacious two-story single family. use it as an owner-occupied property with a rental unit to help offset your mortgage, or maximize rental income with separate 2-bedroom and 3-bedroom units, this property is designed to adapt to

  Dan Mason Perrott Realty

  205 County St, Bennington, VT 05201

Showing Results 201 - 234, Page 6 of 6