Bennington County VT Homes for Sale

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  /46

  $399,900

  • 3 Beds
  • 2.5 Baths
  • 1,920 Sq Ft

  735 Granger Hollow Rd, North Bennington, VT 05257

  Set privately on 25.34 acres, this 3BR/2BA contemporary-style home offers expansive views and a peaceful setting just 15 minutes from Bennington. Kitchen with breakfast nook opens out onto a back deck and the spacious living room features a cathedral ceiling and dramatic floor-to-ceiling fieldstone fireplace, creating an impressive focal point and inviting gathering space. First floor also

  Vicki Wilson Maple Leaf Real Estate

  735 Granger Hollow Rd, North Bennington, VT 05257
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  /30

  $499,000

  • 4 Beds
  • 3.5 Baths
  • 2,345 Sq Ft

  4910 Vaughn Farm Rd Unit 10, Manchester, VT 05255

  There is something special about reaching the top of Torbank and looking west. From this exceptional end unit, the view opens across Manchester toward the broad face of Mt. Equinox, changing with the light from morning sunrise to golden afternoon and dramatic evening skies.Once the home of Torbank’s original developer, this three-level condominium occupies one of the property’s highest

  Derryl Lang Four Seasons Sotheby's Int'l Realty

  4910 Vaughn Farm Rd Unit 10, Manchester, VT 05255
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  /44

  $1,375,000

  • 3 Beds
  • 3 Baths
  • 2,457 Sq Ft

  1474 Dorset West Rd, Dorset, VT 05251

  "Spring Meadow" is textured with history and offers 10 acres of idyllic landscaping featuring the Ethan Allen Spring, a refreshing brook, perennial and vegetable gardens, wild flower meadow, orchard trees, trails throughout 10 acres, and a house that was moved to the site in the 1920's and lovingly added onto creating 2457 SF of one floor living with a separate guest cottage that is privately set

  Laura Beckwith Josiah Allen Real Estate, Inc.

  1474 Dorset West Rd, Dorset, VT 05251
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  /53

  $949,000

  Open House 9/05

  • 3 Beds
  • 3 Baths
  • 1,823 Sq Ft

  40 Kelleher Rd, Dorset, VT 05251

  Where Vermont Living Feels EffortlessDorset Home, Guest Cottage, Pond & Mountain ViewsSettle into the beauty of Dorset with a property that feels like a true Vermont retreat. This lovingly maintained offering pairs a welcoming main residence with a separate one-bedroom cottage, 4.5 acres of open land, a private pond, and beautiful views creating a rare opportunity to enjoy space,

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  40 Kelleher Rd, Dorset, VT 05251
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  /25

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,688 Sq Ft

  171 Garbrooke Dr, Bennington, VT 05201

  Welcome to this inviting Cape-style home offering 3 bedrooms, 2 baths and a comfortable layout designed for both everyday living and entertaining. The main level features an open-concept kitchen and dining area that flows directly onto a huge back deck—an ideal spot for summer dinners, gatherings or simply relaxing while overlooking the secluded, wooded backyard. With both a living room and

  Lilli West Maple Leaf Real Estate

  171 Garbrooke Dr, Bennington, VT 05201
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  /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
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  /36

  $349,900

  • 2,584 Sq Ft

  219-221 Washington Ave, Bennington, VT 05201

  Side-by-side duplex in a sought-after area in the heart of Bennington, offering the charm of yesteryear with modern conveniences. This well-maintained property presents an excellent investment opportunity, whether you're looking for a rental property generating substantial income or the option to owner-occupy one unit while renting the other to help offset your mortgage. Boasting many tasteful

  Matt Waddington Hoffman Real Estate

  219-221 Washington Ave, Bennington, VT 05201
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  /22

  $74,500

  • 1 Bed
  • 586 Sq Ft

  845 Bailey Hill Rd, Readsboro, VT 05350

  Discover the charm of this traditional Vermont Camp. Bring your ATV and explore the trails right from your own property. Equipped with a generator and a 300-gallon water holding tank, you'll have access to running water for the kitchen sink and an outdoor shower. Cooking is made easy with a propane stove and lights powered by propane. Rooftop solar panels charge four batteries, which operate the

  Michelle O'Neil Deerfield Valley Real Estate

  845 Bailey Hill Rd, Readsboro, VT 05350
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  /47

  $685,000

  • 3 Beds
  • 3 Baths
  • 3,153 Sq Ft

  262 Timber Trail Rd, Shaftsbury, VT 05262

  Vermont Home with Mountain, Meadow and Garden viewsNestled in the Green Mountains of Vermont, this 3 bedroom 3 bath home offers scenic views, open spaces, and the tranquility of Vermont living. Situated on three separately surveyed lots, the beautifully maintained property features Heirloom apple trees, park like forests and lush perennial gardens bursting with color throughout the

  

  Margretta Fischer

  Wohler Realty Group

  262 Timber Trail Rd, Shaftsbury, VT 05262
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  /39

  $189,900

  • 2 Beds
  • 1 Bath
  • 462 Sq Ft

  301 Beech St, Bennington, VT 05201

  Cute, cozy, and move-in ready! This freshly renovated 2-bedroom, 1-bath home has been updated from the ground up and offers comfortable, low-maintenance living in a convenient Bennington location. Recent improvements include a brand-new kitchen and bathroom, new flooring, fresh paint, new baseboards, new roof, front porch and expanded driveway. The home features electric baseboard heat along with

  Floyd Amidon Maple Leaf Real Estate

  301 Beech St, Bennington, VT 05201
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  /59

  $199,900

  • 3 Beds
  • 1 Bath
  • 1,132 Sq Ft

  12 Hurley Ln, Bennington, VT 05201

  Discover the potential of this charming 3-bedroom, 1-bath cabin situated on 2.17 private acres. Offering a peaceful and secluded setting while still conveniently located close to town, this property provides the best of both worlds. The property also includes a barn, providing additional space for storage, hobbies, or other possibilities. The home is served by an existing well and septic system,

  Floyd Amidon Maple Leaf Real Estate

  12 Hurley Ln, Bennington, VT 05201
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  /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
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  /26

  $599,000

  Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  33 Burnt Hill Ln, Winhall, VT 05340

  Coming Soon....showings begin Saturday, August 29, 2026. Experience four season Vermont living at 33 Burnt Hill Road in Strattonwald, a recreational community in Winhall just minutes from Stratton Mountain. Set on 1.09 wooded acres, this three bedroom, two bath mountain home combines privacy and Vermont character with access to the Strattonwald swimming pond and beach, tennis courts and winter

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  33 Burnt Hill Ln, Winhall, VT 05340
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  /50

  $345,000

  • 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
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  /7

  $108,000

  • Land
  • 1 Acre
  • $108,000 per Acre

  0 Sylvan Ridge Rd Unit 5106244, Winhall, VT 05340

  Discover the opportunity to create your own Vermont getaway on this beautiful 1-acre parcel on Sylvan Ridge Road in Winhall. Ideally situated between Stratton Mountain and Bromley Mountain, this location offers easy access to some of Southern Vermont's best year-round recreation. In winter, enjoy skiing and snowboarding at nearby Stratton and Bromley. During spring summer and fall, the area comes

  David Shehadi Josiah Allen Real Estate, Inc.

  0 Sylvan Ridge Rd Unit 5106244, Winhall, VT 05340
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  /34

  $345,000

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  19 Winhall Condo Rd Unit 4, Winhall, VT 05340

  Tucked at the end of a quiet back road less than one mile from the Stratton Access Road, The Winhall Condos offer a charming mountain retreat with easy access to both Stratton and Manchester. This updated 2-bedroom, 2-bath unit features an open-concept kitchen, living, and dining area, two elevated decks, and amazing views of Stratton Mountain. Offered furnished and ready to enjoy, it’s an ideal

  Cheyanne Pugliese

  19 Winhall Condo Rd Unit 4, Winhall, VT 05340
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  /58

  $2,399,000

  • 4 Beds
  • 3.5 Baths
  • 4,536 Sq Ft

  33 Stone Lodge Rd, Winhall, VT 05340

  Experience Premiere Luxury living in this newly built mountain residence with extraordinary panoramic views . Just minutes to Stratton Mountain's Trails and move in ready, no detail has been overlooked with superior craftsmanship, energy efficiency and contemporary design. The handcrafted Timber Frame great room , defined by cathedral ceilings, wood burning stone hearth and expansive windows,

  Kim Morgan-Wohler Wohler Realty Group

  33 Stone Lodge Rd, Winhall, VT 05340
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  /48

  $449,000

  • 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

  928 Main Rd, Stamford, VT 05352
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  /27

  $995,000

  • 5 Beds
  • 2 Baths
  • 3,522 Sq Ft

  2529 Main St, Manchester, VT 05254

  Light, bright, & thoughtfully updated, this charming Manchester village home offers the perfect blend of antique character, modern convenience, & exceptional outdoor space. Set on nearly five acres of level, usable land with beautiful views toward Mount Equinox, the property provides room to spread out & enjoy everything Vermont living has to offer—whether gathering with family & friends,

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  2529 Main St, Manchester, VT 05254
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  /60

  $4,995,000

  • 5 Beds
  • 6.5 Baths
  • 7,455 Sq Ft

  440 Marcia Ln, Dorset, VT 05251

  A rare opportunity awaits at this exceptional Dorset Hollow estate, privately situated at the end of exclusive Marcia Lane. Perched high on Dorset Mountain across 16.74 acres, the property captures breathtaking long-range views of Owls Head, Equinox Mountain, and beyond.Built in 2005 by renowned craftspeople, this 7,451-square-foot, five-bedroom, seven-bath estate has undergone a

  David Halligan Four Seasons Sotheby's Int'l Realty

  440 Marcia Ln, Dorset, VT 05251
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  /40

  $989,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  3542 North Rd, Arlington, VT 05250

  Modern Four-Season Home with Exceptional Views & Workshop Space.Built in 2022, this modern home offers easy one-floor living, beautiful four-season views, and a convenient location close to Manchester’s amenities.The bright, open and airy main level features 3 bedrooms and 2 bathrooms, with comfortable living spaces designed to take full advantage of the surrounding views. The

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  3542 North Rd, Arlington, VT 05250
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  /2

  $245,000

  • Land
  • 3 Acres
  • $81,667 per Acre

  0 Fox Ln Unit 5105566, Dorset, VT 05251

  The last lot located in a quaint Dorset cul de sac. One of the few building lots left in the most coveted Dorset village, abutting national forest on the marsh. This lot is the only available lot in Dorset Village. Home Owners Association, organized and fully functional by the residents of Fox Lane. Take a walk, create a bench from a fallen tree, in the 18 acre common forested land adjoining the

  Laura Beckwith Josiah Allen Real Estate, Inc.

  0 Fox Ln Unit 5105566, Dorset, VT 05251
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  /40

  $595,000

  $20K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft

  23 Loop Rd Unit 10, Bondville, VT 05340

  Set among sun-dappled woodlands along a peaceful country road, this distinctive post-and-beam home captures the charm of a Vermont sugar shack with the warmth of a classic ski-country retreat. This furnished three bedroom, two bath home offers 1,416 sq ft of inviting living space, thoughtfully designed for both full-time living and memorable getaways. Inside, the vaulted Great Room immediately

  Diana Stugger Four Seasons Sotheby's Int'l Realty

  23 Loop Rd Unit 10, Bondville, VT 05340
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  /8

  $239,000

  • Land
  • 5.35 Acres
  • $44,673 per Acre

  01 Old Depot Rd, West Arlingtn, VT 05250

  Big views, open land, and room to make it your own. Offered as two lots under a single listing, this 5+ acre property is an inviting piece of the Arlington countryside, with sweeping views of both the Taconic and Green Mountains. The open field overlooks a privately maintained pond and enjoys a peaceful setting just down the road from one of Southern Vermont's most charming farms. An approved

  Marek Kovac TPW Real Estate

  01 Old Depot Rd, West Arlingtn, VT 05250
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  /9

  $159,900

  • 5 Beds
  • 1 Bath
  • 1,593 Sq Ft

  493 Main Rd, Stamford, VT 05352

  Bring your imagination to this over 1500 sq. ft. 5 bedroom, New England farmhouse and let it go wild! Level one acre lot with attached shed and small outbuilding for animals or projects. Very easy main route access, close to downtown and Stamford Elementary school. Stamford Golf & Country Club is around the corner, and skiing is a short drive away! Just 10 minutes to North Adams, and under 30

  Pauline Green Lamacchia Realty, Inc. - Adams

  493 Main Rd, Stamford, VT 05352
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  /20

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,225 Sq Ft

  16B Bromley Knolls Rd Unit B, Winhall, VT 05340

  TURN-KEY VERMONT MOUNTAIN RETREAT JUST MINUTES FROM BROMLEY & STRATTON!Beautifully renovated in 2021, this fully furnished 3-bedroom, 2-bath condominium offers the perfect combination of Vermont charm, modern comfort, and year-round recreation. Located just one minute from Bromley Mountain and approximately ten minutes from Stratton, this property is ideally situated for skiing, hiking,

  Jason Saphire www.HomeZu.com

  16B Bromley Knolls Rd Unit B, Winhall, VT 05340
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  /4

  $20,000

  • Land
  • 1.2 Acres
  • $16,667 per Acre

  0 Bergrucken Ln Unit 377, Stamford, VT 05352

  Trade city sirens for wind-rustled maples on this gently wooded 1.2-acre lot tucked inside Alpenwald Village. Alpenwald, although deed restricted, the light protective covenants keep the area tidy without cramping your architectural imagination. Think A-Frame, modern farmhouse, or a passive solar cottage. Beyond the lot is access to trails that lace through the Green Mountain National Forest.

  Kelly Agrillo Southern Vermont Realty Group

  0 Bergrucken Ln Unit 377, Stamford, VT 05352
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  /32

  $675,000

  • 3 Beds
  • 1 Bath
  • 1,575 Sq Ft

  221 Landgrove Rd, Londonderry, VT 05148

  With more than 80 acres spanning the towns of Landgrove and Peru, this spectacular property is ripe for your imagination and offers several options for new construction, multi-family or generational development, or renovation! Be it choosing the perfect building site for the construction of your Vermont dream house, a total renovation of the existing three-bedroom cottage, or continuing to use

  Claudia Harris Mary Mitchell Miller Real Estate

  221 Landgrove Rd, Londonderry, VT 05148
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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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  /30

  $489,000

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  1180 North Rd, Arlington, VT 05250

  A little bit of Vermont country living, tucked into 3.05 acres in Sunderland! This 4-bedroom, 2.5 bath Colonial offers a great mix of traditional and open concept living, with wood floors, large windows, granite countertops, open kitchen/dining, spacious living room, den/office, mudroom, and first floor laundry. The primary suite features a private bath with soaking tub and walk in closet. Step

  Abi Gregorio

  1180 North Rd, Arlington, VT 05250
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  /32

  $765,000

  • 3 Beds
  • 3 Baths
  • 2,322 Sq Ft

  72 Benson Fuller Dr, Winhall, VT 05340

  Set among the trees just minutes from Stratton Resort, this spacious 3-bedroom, 3-bath mountain home combines beautiful views, flexible living spaces and plenty of room for family and friends. The dramatic main living area features soaring vaulted ceilings, warm wood accents, a floor-to-ceiling stone fireplace and an impressive wall of windows that fills the home with natural light and brings the

  Christine Chovan

  72 Benson Fuller Dr, Winhall, VT 05340
• 

  

  /20

  $535,000

  • 4 Beds
  • 3 Baths
  • 1,974 Sq Ft

  286 Green Mountain Rd, Manchester Center, VT 05255

  Discover comfort, style, and mountain views at Green Mountain Estates. This meticulously maintained split-level ranch offers four bedrooms, three bathrooms, and a flexible floor plan designed for everyday living. The bright upper level features 3 bedrooms an open-concept kitchen with new appliances and dining area that flows seamlessly into a cozy living room. Sliding door lead to a spacious and

  Andy Reed Four Seasons Sotheby's Int'l Realty

  286 Green Mountain Rd, Manchester Center, VT 05255
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  /6

  $19,500

  • Land
  • 1.1 Acres
  • $17,727 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  The land lots on Heartwelleville View Road offer an idyllic setting for your dream home or getaway retreat. These lots are perfectly situated less than 30 minutes from the renowned Mt. Snow, providing easy access to world-class skiing and snowboarding. Just 20 minutes away, you can explore the vibrant cultural scene of North Adams and the acclaimed MASS MoCA.Outdoor enthusiasts will

  Colt Hazell Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
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  /6

  $39,500

  • Land
  • 2.1 Acres
  • $18,810 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  The land lots on Heartwelleville View Road offer an idyllic setting for your dream home or getaway retreat. These lots are perfectly situated less than 30 minutes from the renowned Mt. Snow, providing easy access to world-class skiing and snowboarding. Just 20 minutes away, you can explore the vibrant cultural scene of North Adams and the acclaimed MASS MoCA.Outdoor enthusiasts will

  Colt Hazell Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
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  /8

  $15,500

  • Land
  • 1.2 Acres
  • $12,917 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  The land lots on Heartwelleville View Road offer an idyllic setting for your dream home or getaway retreat. These lots are perfectly situated less than 30 minutes from the renowned Mt. Snow, providing easy access to world-class skiing and snowboarding. Just 20 minutes away, you can explore the vibrant cultural scene of North Adams and the acclaimed MASS MoCA.Outdoor enthusiasts will

  Colt Hazell Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
• 

  /2

  $58,000

  • Land
  • 20,908 Sq Ft
  • $120,833 per Acre

  33 Asa's Way, Bennington, VT 05257

  This lot in beautiful North Bennington is ready to go! Building plans have been drawn up and available to come with the property for an approx. 2200 sq ft 3 bed, 2 bath home with decks facing the mountains. This lot has the electric, water, and sewer available at the street. Beyond having school choice for the elementary it also boasts being the second highest elevation lot in the development,

  William Paquin Maple Leaf Real Estate

  33 Asa's Way, Bennington, VT 05257
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  /32

  $595,000

  • Land
  • 23.62 Acres
  • $25,191 per Acre

  3213 West Rd, Bennington, VT 05201

  Some properties offer acreage, some offer breathtaking views, very few offer both along with a rich history worth preserving and a future waiting to be imagined. For generations, this rare south-facing farm has looked across the valley enjoying sunlight from dawn until dusk & panoramic views that are exceptional! More than productive farmland, it became a place where neighbors and families

  

  Monique Geannelis

  Mahar McCarthy Real Estate

  3213 West Rd, Bennington, VT 05201
• 

  

  /21

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  112 Aldrich Rd, Peru, VT 05152

  Opportunity awaits in this three-bedroom, two-bath home set in a peaceful Vermont location near Bromley Mountain, Hapgood Pond, and the Catamount Trail. The single-level floor plan offers a comfortable living room with a brick fireplace, a separate dining area, and plenty of natural light. A new roof provides an important recent improvement, while the interior is ready for updates and a new

  Christine Chovan

  112 Aldrich Rd, Peru, VT 05152
• 

  

  /33

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,911 Sq Ft

  21 Russett Dr, Bennington, VT 05201

  Tucked into a beautifully maintained neighborhood, 21 Russett Drive is the kind of home that feels welcoming the moment you arrive. Beautiful landscaping, a charming Dutch door, and a thoughtfully cared for yard give this property an almost secret garden feel private, inviting, and full of character.Inside, the versatility of this home truly shines. The main level offers a comfortable living

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  21 Russett Dr, Bennington, VT 05201
• 

  

  /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

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