181

Bennington County VT Houses for Sale

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  • 3149 W Hill Dr, Readsboro, VT 05350
    3149 W Hill Dr, Readsboro, VT 05350
    3149 W Hill Dr, Readsboro, VT 05350
    /42

    $325,000

    • 2 Beds
    • 1 Bath
    • 976 Sq Ft

    3149 W Hill Dr, Readsboro, VT 05350

    A little piece of Vermont just waiting to be discovered! Tucked into nearly 13 surveyed acres of woods, this charming 1970s ranch offers the peace, privacy & simplicity so many look for. A stone wall outlines the parking area, with stone steps leading up & into the front screened in porch that overlooks the yard & meadows. Inside, you'll find 2 bedrooms, wood floors, built-in bookshelves, dining

    Colleen Zajac MONARCH REALTY, INC.

    3149 W Hill Dr, Readsboro, VT 05350
  • 1649 E Manchester Rd, Manchester Center, VT 05255
    1649 E Manchester Rd, Manchester Center, VT 05255
    1649 E Manchester Rd, Manchester Center, VT 05255
    /40

    $579,900

    $15K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,050 Sq Ft

    1649 E Manchester Rd, Manchester Center, VT 05255

    5 bedroom, 2 bath Manchester home in a highly functional ski location: about 8 minutes to Bromley and under 25 minutes to both Magic and Stratton, plus roughly 2 minutes to downtown Manchester and 1 minute to Route 7 for straightforward access in all conditions. The setting supports frequent winter use and works equally well for year-round occupancy. The house underwent a full gut renovation in

    Jonathan Minerick

    1649 E Manchester Rd, Manchester Center, VT 05255
  • 1675 Vermont 9, Searsburg, VT 05363
    1675 Vermont 9, Searsburg, VT 05363
    1675 Vermont 9, Searsburg, VT 05363
    /28

    $159,000

    $30K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 760 Sq Ft

    1675 Vermont 9, Searsburg, VT 05363

    Welcome to Peaceful Pines, your cottage in the woods near the entrance to the Green Mountain National Forest. The charming two-bedroom cottage/camp was lovingly maintained. Key updates include a completely rebuilt chimney and masonry work, a wood stove ( in addition to baseboard heat) to take the chill out of those fall and winter evenings, T11 siding, a newer roof, and a private back deck with

    Jacki Murano Southern Vermont Realty Group

    1675 Vermont 9, Searsburg, VT 05363
  • 25 Benson Fuller Dr, Bondville, VT 05340
    25 Benson Fuller Dr, Bondville, VT 05340
    25 Benson Fuller Dr, Bondville, VT 05340
    /38

    $795,000

    • 4 Beds
    • 3.5 Baths
    • 4,104 Sq Ft

    25 Benson Fuller Dr, Bondville, VT 05340

    Where Mountains Meet Modern Living: Perched just moments from the energy of Stratton Mountain Resort, this contemporary mountain home reimagines what a Vermont getaway feels like. From the moment you step inside, the design does exactly what a great contemporary home should: it steps back and lets nature take center stage. Massive, soaring windows act as living art pieces, framing sweeping,

    Robin Apps Four Seasons Sotheby's Int'l Realty

    25 Benson Fuller Dr, Bondville, VT 05340
  • 1625 Barnumville Rd, Manchester Center, VT 05255
    1625 Barnumville Rd, Manchester Center, VT 05255
    1625 Barnumville Rd, Manchester Center, VT 05255
    /25

    $550,000

    Open Mon 1PM - 3PM
    • 3 Beds
    • 2 Baths
    • 2,009 Sq Ft

    1625 Barnumville Rd, Manchester Center, VT 05255

    Offered for the first time in almost 40 years, this charming farmhouse is set on a picturesque 1.7 acre parcel of open land in Manchester, Vermont. Ideally located directly across from East of Equinox horse farm, the property offers a country setting just minutes from town.The main level features tall ceilings, a spacious kitchen with an adjoining dining area, and a generous living room

    Tatsiana Clark Four Seasons Sotheby's Int'l Realty

    1625 Barnumville Rd, Manchester Center, VT 05255
  • 773 Oberdorf Rd, Readsboro, VT 05350
    773 Oberdorf Rd, Readsboro, VT 05350
    773 Oberdorf Rd, Readsboro, VT 05350
    /23

    $329,900

    $20K PRICE DROP
    • 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
  • 515 W Fields Rd, Manchester, VT 05254
    515 W Fields Rd, Manchester, VT 05254
    515 W Fields Rd, Manchester, VT 05254
    /40

    $3,995,000

    $3M PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 6,500 Sq Ft

    515 W Fields Rd, Manchester, VT 05254

    Enduring values expressed in stone and wood! VERMONT CRAFTMANSHIP...A WORK OF ART!! Offering a private haven just minutes from downtown, in the heart of Manchester Village, nestled in the foothills of Equinox Mtn. is this rareand exceptional 5-bedroom, 6-bathroom home....The creative designof Architect Ramsey Gourd and Master Builder Mark Breen, well knownas two of Southern Vermont's

    Sunny Breen Josiah Allen Real Estate, Inc.

    515 W Fields Rd, Manchester, VT 05254
  • 1629 Mann Hill Rd N, Pownal, VT 05261
    1629 Mann Hill Rd N, Pownal, VT 05261
    1629 Mann Hill Rd N, Pownal, VT 05261
    /47

    $795,000

    $50K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 3,875 Sq Ft

    1629 Mann Hill Rd N, Pownal, VT 05261

    Facing west to capture breathtaking mountain views and unforgettable sunsets from nearly every room, this exceptional modern farmhouse seamlessly blends timeless character with thoughtful updates. Rich hardwood floors, cozy alcoves, and original beams in the living room create a warm and inviting atmosphere throughout. The spacious floor plan features five generously sized bedrooms, each with its

    Kelley Mccarthy Mahar McCarthy Real Estate

    1629 Mann Hill Rd N, Pownal, VT 05261
  • 312 Beartown Rd, Manchester Center, VT 05255
    312 Beartown Rd, Manchester Center, VT 05255
    312 Beartown Rd, Manchester Center, VT 05255
    /56

    $1,775,000

    $425K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,000 Sq Ft

    312 Beartown Rd, Manchester Center, VT 05255

    Set on 24 private acres with sweeping mountain views, 312 Beartown Road offers a sense of complete escape while remaining moments from Manchester.Filled with natural light, the four-bedroom residence is thoughtfully designed to capture its extraordinary setting. Every room is oriented to the outdoors, with expansive windows that keep the Vermont landscape always in view.The chef's

    Christiane Carroccio TPW Real Estate

    312 Beartown Rd, Manchester Center, VT 05255
  • 498 Townline Rd, Bennington, VT 05201
    498 Townline Rd, Bennington, VT 05201
    498 Townline Rd, Bennington, VT 05201
    /54

    $460,000

    $35K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,312 Sq Ft

    498 Townline Rd, Bennington, VT 05201

    If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the

    Betty McEnaney Diamond Realty

    498 Townline Rd, Bennington, VT 05201
  • 2734 Mad Tom Rd, East Dorset, VT 05253
    2734 Mad Tom Rd, East Dorset, VT 05253
    2734 Mad Tom Rd, East Dorset, VT 05253
    /60

    $735,000

    $64K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,420 Sq Ft

    2734 Mad Tom Rd, East Dorset, VT 05253

    Vermont's rustic charm will welcome you in a warm embrace every time you enter this custom built post and beam home on 37.5 private acres. The home features 2 bedrooms plus loft and 2 baths with tons of natural woodwork. The property also includes a detached post and beam garage with additional space above, perfect for an art studio, writer's workshop or plenty of extra storage. The property

    David Citron RE/MAX Four Seasons

    2734 Mad Tom Rd, East Dorset, VT 05253
  • 87 B Hill Rd, Pownal, VT 05261
    87 B Hill Rd, Pownal, VT 05261
    87 B Hill Rd, Pownal, VT 05261
    /41

    $425,000

    • 3 Beds
    • 2.5 Baths
    • 2,760 Sq Ft

    87 B Hill Rd, Pownal, VT 05261

    Welcome to your own private Vermont retreat. Nestled on 3.2 acres in the mountains of Pownal, this Adirondack-style home offers the perfect blend of rustic charm, thoughtful craftsmanship, and everyday comfort.Surrounded by walking trails, blueberry and raspberry bushes, fruit trees, and abundant wildlife, the property is designed for those who appreciate the outdoors. Enjoy mountain views

    Lilli West Maple Leaf Real Estate

    87 B Hill Rd, Pownal, VT 05261
  • 109 Winhall Hollow Rd, Winhall, VT 05340
    109 Winhall Hollow Rd, Winhall, VT 05340
    109 Winhall Hollow Rd, Winhall, VT 05340
    /31

    $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
  • 686 Route 30, Dorset, VT 05251
    686 Route 30, Dorset, VT 05251
    686 Route 30, Dorset, VT 05251
    /27

    $369,000

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

    686 Route 30, Dorset, VT 05251

    Village Mixed Use zoned Residence and Separate cottage located in the Hamlett of South Dorset...nearby Dorset's elementary School and Sheldon's Market. Conveniently located 3 miles from Manchester Ctr to the South or Dorset Village to the North. The main house offers 1350 SF, 2 bedrooms with overflow room, large closet, and sunroom entrance... The cottage is 675 SF with one bedroom and a

    Laura Beckwith Josiah Allen Real Estate, Inc.

    686 Route 30, Dorset, VT 05251
  • 72 Benson Fuller Dr, Winhall, VT 05340
    72 Benson Fuller Dr, Winhall, VT 05340
    72 Benson Fuller Dr, Winhall, VT 05340
    /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
  • 51 Pageant St, Bennington, VT 05201
    51 Pageant St, Bennington, VT 05201
    51 Pageant St, Bennington, VT 05201
    /38

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    51 Pageant St, Bennington, VT 05201

    There is something special about a home with character, and this charming 3BR property has it in abundance! Set in an established neighborhood within sight of the Mt. Anthony Country Club, this inviting home offers the warmth and craftsmanship of an earlier era combined with the comforts buyers are looking for. From the moment you arrive, the covered front porch welcomes you home. With generous

    Angela Bevin Maple Leaf Real Estate

    51 Pageant St, Bennington, VT 05201
  • 1 Beaver St, Bondville, VT 05340
    1 Beaver St, Bondville, VT 05340
    1 Beaver St, Bondville, VT 05340
    /38

    $605,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,288 Sq Ft

    1 Beaver St, Bondville, VT 05340

    Ideally located between Manchester and the mountains, this home offers the perfect blend of convenience, comfort, and Vermont charm. Just 10 minutes to Stratton, 5 minutes to Bromley, and 12 minutes to Manchester, you’ll enjoy easy access to skiing, dining, shopping, and year-round recreation.Inside, the home features a spacious living room filled with natural light, creating a warm and

    Carrie Mathews Winhall Real Estate

    1 Beaver St, Bondville, VT 05340
  • 100 McCarthy Acres, North Bennington, VT 05257
    100 McCarthy Acres, North Bennington, VT 05257
    100 McCarthy Acres, North Bennington, VT 05257
    /37

    $329,000

    $70K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,938 Sq Ft

    100 McCarthy Acres, North Bennington, VT 05257

    Nearly Lakefront Living in the Heart of North Bennington!Come for the space, stay for the location! This spacious home offers over 2,500 sq. ft. of living space, including 5 bedrooms, 3 full bathrooms, a large home office in the finished basement, and a versatile 250 sq. ft. bonus room attached to one of the upstairs bedrooms. The original garage has been thoughtfully transformed into a 600

    Nicholas Charest Maple Leaf Real Estate

    100 McCarthy Acres, North Bennington, VT 05257
  • 13 Golden Triangle Rd, Winhall, VT 05340
    13 Golden Triangle Rd, Winhall, VT 05340
    13 Golden Triangle Rd, Winhall, VT 05340
    /22

    $430,000

    • 5 Beds
    • 2 Baths
    • 1,664 Sq Ft

    13 Golden Triangle Rd, Winhall, VT 05340

    The ideal opportunity in a prime location, minutes from Stratton Mountain, Bromley Mountain, and the charming town of Manchester, this 5-bedroom, 2-bathroom home has what you need for your primary Vermont residence or a quiet place to getaway. The spacious living room and dining area is complimented by a wrap around porch. This home is low maintenance and setup well for those who want a

    Mike England Michael England Real Estate

    13 Golden Triangle Rd, Winhall, VT 05340
  • 11 W Round Rd, Winhall, VT 05340
    11 W Round Rd, Winhall, VT 05340
    11 W Round Rd, Winhall, VT 05340
    /40

    $1,325,000

    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft

    11 W Round Rd, Winhall, VT 05340

    11 Round Tree Road, Winhall, VT 05340A landmark on Round Tree Road, this house has inviting curb appeal with its stone façade and archway. With 1.83 acres the house has a very private setting in back for the patio, fire pit and hot tub. Unique U-shaped driveway has plenty of room for friends and family. Appropriately sized mud room for all the gear. Downstairs family room with fireplace and

    Andrew King Stratton Real Estate

    11 W Round Rd, Winhall, VT 05340
  • 145 White Farm Ln, Shaftsbury, VT 05262
    145 White Farm Ln, Shaftsbury, VT 05262
    145 White Farm Ln, Shaftsbury, VT 05262
    /54

    $940,000

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

    145 White Farm Ln, Shaftsbury, VT 05262

    Nestled in a peaceful five acre setting just minutes from the shopping, dining, and everyday conveniences of both Bennington and Manchester, this beautifully maintained home offers privacy, comfort, and accessibility.Thoughtfully updated, this home offers a timeless, inviting style designed to feel welcoming for years to come. The newly renovated high end kitchen is both beautiful and

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    145 White Farm Ln, Shaftsbury, VT 05262
  • 21 Jameson Flats Unit Duplex Unit B, Manchester, VT 05255
    21 Jameson Flats Unit Duplex Unit B, Manchester, VT 05255
    21 Jameson Flats Unit Duplex Unit B, Manchester, VT 05255
    /17

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 1,368 Sq Ft

    21 Jameson Flats Unit Duplex Unit B, Manchester, VT 05255

    THE PROGRAM: Purchase Price Assistance/ Mortgage Payment Reduction:Eligibility Requirements: * Vermont Residency or Residency at time of Purchase * First Time Vermont Homebuyer * Household Income at or Below $178,735* * Qualify for a Bank Mortgage * 10% Down Payment The developer will offer Gifted Equity and Paid Points at closing that will reduce the purchase price of the real estate and

    Britt Wohler

    21 Jameson Flats Unit Duplex Unit B, Manchester, VT 05255
  • 760 W Mountain Rd, Shaftsbury, VT 05262
    760 W Mountain Rd, Shaftsbury, VT 05262
    760 W Mountain Rd, Shaftsbury, VT 05262
    /36

    $440,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,343 Sq Ft

    760 W Mountain Rd, Shaftsbury, VT 05262

    Tucked away in a private setting in Shaftsbury, this inviting home sits on 2.12 acres, offering both tranquility and convenience-just a short drive to both Manchester and Bennington. With 2,350 square feet of living space, the home features 3 bedrooms and 2.5 baths, thoughtfully designed for comfort and functionality. Many upgrades were completed in 2006, enhancing both efficiency and livability.

    Kelley Mccarthy Mahar McCarthy Real Estate

    760 W Mountain Rd, Shaftsbury, VT 05262
  • 3039 Vermont 30, Pawlet, VT 05761
    3039 Vermont 30, Pawlet, VT 05761
    3039 Vermont 30, Pawlet, VT 05761
    /44

    $2,495,000

    • 4 Beds
    • 5.5 Baths
    • 4,506 Sq Ft

    3039 Vermont 30, Pawlet, VT 05761

    Tucked away at the end of a long, winding driveway, this remarkable Dorset Village estate sits on one of the area's largest parcels—over six private acres. A rare blend of privacy, history, and elegance, the home features four stunning stone fireplaces, exposed antique beams, reclaimed wood details, and abundant natural light throughout its flowing layout. Designed for gathering and making

    Carrie Mathews Winhall Real Estate

    3039 Vermont 30, Pawlet, VT 05761
  • 1253 Old West Rd, Arlington, VT 05250
    1253 Old West Rd, Arlington, VT 05250
    1253 Old West Rd, Arlington, VT 05250
    /38

    $399,000

    $11K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,648 Sq Ft

    1253 Old West Rd, Arlington, VT 05250

    Enjoy beautiful Green Mountain views from this exceptionally well-maintained home offering the perfect blend of comfort, space, and Vermont country living. The bright, inviting floor plan features a spacious living room with a gas fireplace, a well-appointed kitchen with abundant cabinetry, center island, gas range, stainless steel appliances, and direct access to the expansive rear deck

    Jeffrey Dorman

    1253 Old West Rd, Arlington, VT 05250
  • 99 Holly's Way, Rupert, VT 05776
    99 Holly's Way, Rupert, VT 05776
    99 Holly's Way, Rupert, VT 05776
    /33

    $925,000

    $175K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,403 Sq Ft

    99 Holly's Way, Rupert, VT 05776

    Imagine waking to the quiet rhythm of the Vermont countryside, where morning light stretches across open meadows, woodland trails begin just beyond your door, and the pace of life slows to match the landscape. Set on 26 acres in Rupert, this exceptional property offers a rare combination of privacy, craftsmanship, and room to pursue the life you've imagined. The home is designed to feel connected

    Derryl Lang Four Seasons Sotheby's Int'l Realty

    99 Holly's Way, Rupert, VT 05776
  • 777 McCooey Dr, Manchester Center, VT 05255
    777 McCooey Dr, Manchester Center, VT 05255
    777 McCooey Dr, Manchester Center, VT 05255
    /26

    $1,575,000

    • 3 Beds
    • 2.5 Baths
    • 3,264 Sq Ft

    777 McCooey Dr, Manchester Center, VT 05255

    Set back from a quiet country road in Manchester, Vermont, this spaciousFederal farmhouse style home offers a wonderful blend of comfort, privacyand Vermont charm. The classic white exterior with its attached red barncreates a welcoming first impression, while the home’s thoughtful designprovides plenty of space for everyday living, entertaining and enjoying thepeaceful

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

    777 McCooey Dr, Manchester Center, VT 05255
  • 7 Roundtree Rd, Winhall, VT 05340
    7 Roundtree Rd, Winhall, VT 05340
    7 Roundtree Rd, Winhall, VT 05340
    /41

    $910,000

    $40K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,031 Sq Ft

    7 Roundtree Rd, Winhall, VT 05340

    Discover the perfect mountain retreat at 7 Roundtree Road, a contemporary and beautifully designed 4-bedroom home set on 1.37 private acres in one of Stratton’s most sought-after neighborhoods. Ideally located just a quick drive to the Base Lodge—or simply hop on the convenient shuttle for effortless access to the slopes, this property offers the best of Stratton living in every season.Step

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    7 Roundtree Rd, Winhall, VT 05340
  • 145 Oberdorf Rd, Readsboro, VT 05350
    145 Oberdorf Rd, Readsboro, VT 05350
    145 Oberdorf Rd, Readsboro, VT 05350
    /45

    $490,642

    $8K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,708 Sq Ft

    145 Oberdorf Rd, Readsboro, VT 05350

    Welcome to Alpenwald Village, a peaceful mountain community in scenic Readsboro, Vermont. This charming 4 bedroom chalet sits on 2 private acres and offers the perfect blend of comfort, style, and access to Vermont’s four-season lifestyle. Whether you're searching for a full-time residence or the ideal vacation getaway, this beautifully updated home delivers. Step inside to discover thoughtful

    Evan Russell Real Broker LLC

    145 Oberdorf Rd, Readsboro, VT 05350
  • 33 Burnt Hill Ln, Winhall, VT 05340
    33 Burnt Hill Ln, Winhall, VT 05340
    33 Burnt Hill Ln, Winhall, VT 05340
    /26

    $599,000

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

    33 Burnt Hill Ln, Winhall, VT 05340

    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 shuttle service to Stratton.Inside, natural wood,

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    33 Burnt Hill Ln, Winhall, VT 05340
  • 515 Quarry Rd, Bennington, VT 05201
    515 Quarry Rd, Bennington, VT 05201
    515 Quarry Rd, Bennington, VT 05201
    /60

    $695,000

    • 4 Beds
    • 2 Baths
    • 1,614 Sq Ft

    515 Quarry Rd, Bennington, VT 05201

    Peaceful, private, and completely surrounded by nature, this beautifully renovated contemporary home offers the perfect mountain retreat nestled on 14.7 acres on the side of Mt. Anthony with seasonal views and unmatched tranquility. Enjoy direct access to miles of hiking trails, abundant wildlife, and the rare protection of no future development permitted above this elevation, preserving the

    Vicki Wilson Maple Leaf Real Estate

    515 Quarry Rd, Bennington, VT 05201
  • 159 Winhall Hollow Rd, Bondville, VT 05340
    159 Winhall Hollow Rd, Bondville, VT 05340
    159 Winhall Hollow Rd, Bondville, VT 05340
    /60

    $5,575,000

    • 7 Beds
    • 9.5 Baths
    • 9,915 Sq Ft

    159 Winhall Hollow Rd, Bondville, VT 05340

    Privately situated in a most beautiful setting, this grand Vermont estate commands a remarkable landscape, with Stratton Mountain rising majestically beyond the tree line. A sweeping private drive sets the tone for an extraordinary arrival; open meadows, a serene pond, and beautifully preserved grounds before revealing the 9915 SF residence itself and massive barn. There's an immediate sense of

    Kim Morgan-Wohler Wohler Realty Group

    159 Winhall Hollow Rd, Bondville, VT 05340
  • 3530 Vt Route 346, Pownal, VT 05261
    3530 Vt Route 346, Pownal, VT 05261
    3530 Vt Route 346, Pownal, VT 05261
    /34

    $249,900

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,810 Sq Ft

    3530 Vt Route 346, Pownal, VT 05261

    This historic house, built in 1880, is nestled in the quiet village of North Pownal. It is situated on a large, level lot and offers the timeless charm of yesteryear. The first floor features a roomy kitchen with Kenmore Plus Stainless-Steel appliances, an open-concept living room and dining room, an updated bathroom, and a convenient first-floor laundry room. The back porch has been partially

    Matt Waddington Hoffman Real Estate

    3530 Vt Route 346, Pownal, VT 05261
  • 68 Green Peak Orchard S, East Dorset, VT 05253
    68 Green Peak Orchard S, East Dorset, VT 05253
    68 Green Peak Orchard S, East Dorset, VT 05253
    /48

    $2,950,000

    $335K PRICE DROP
    • 5 Beds
    • 6 Baths
    • 6,900 Sq Ft

    68 Green Peak Orchard S, East Dorset, VT 05253

    Welcome to Green Peak Orchard in Dorset, Vermont, where timeless architecture and exceptional craftsmanship define this custom Greek Revival residence on 9.9 private acres. Surrounded by mature landscaping, stone walls, and slate terraces, this remarkable home blends classic New England elegance with modern comfort. Designed with meticulous attention to detail, the home features wide-plank

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

    68 Green Peak Orchard S, East Dorset, VT 05253
  • 3622 Dorset West Rd, Dorset, VT 05251
    3622 Dorset West Rd, Dorset, VT 05251
    3622 Dorset West Rd, Dorset, VT 05251
    /28

    $750,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,610 Sq Ft

    3622 Dorset West Rd, Dorset, VT 05251

    Unique Dorset West Road offering....This rare opportunity beckons creativity,craft, and charm! Begs all those ready, willing and able to renovate, keeping the existing home, whilst enjoying life in an extremely beautiful and desirable location. Enjoy the beautiful framed in mountain views from most interior living spaces and from the back patio/yard. This 6.6 acre rolling property boasts

    Sunny Breen Josiah Allen Real Estate, Inc.

    3622 Dorset West Rd, Dorset, VT 05251
  • 107 Lyons St, Bennington, VT 05201
    107 Lyons St, Bennington, VT 05201
    107 Lyons St, Bennington, VT 05201
    /4

    $80,000

    • 4 Beds
    • 2 Baths
    • 1,465 Sq Ft

    107 Lyons St, Bennington, VT 05201

    Situated on a peaceful dead-end street, this home offers tremendous potential for investors, contractors, or buyers looking to create their dream home. The property features 3 bedrooms, with the possibility of a fourth, along with 2 bathrooms, providing a highly desirable layout and ample living space. With some vision, care, and updates, this home can be transformed into a beautiful residence in

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    107 Lyons St, Bennington, VT 05201
  • 20 Blackberry Ln, Peru, VT 05152
    20 Blackberry Ln, Peru, VT 05152
    20 Blackberry Ln, Peru, VT 05152
    /60

    $1,495,000

    • 5 Beds
    • 5 Baths
    • 5,029 Sq Ft

    20 Blackberry Ln, Peru, VT 05152

    Welcome home to this spectacular, multi-level property in Bromley Village, a private slopeside community in Peru. Conveniently located just a short walk to/from Bromley Mountain's ski slopes, the Village Clubhouse, and across from the Village pond. A well designed layout which features 5 Bedrooms (including two En-suites), a total of 5 Bathrooms, multiple spacious Living areas, and a fabulous

    Dylan Gage Bromley Real Estate

    20 Blackberry Ln, Peru, VT 05152
  • 291 Springhill Rd, Bennington, VT 05201
    291 Springhill Rd, Bennington, VT 05201
    291 Springhill Rd, Bennington, VT 05201
    /37

    $375,000

    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft

    291 Springhill Rd, Bennington, VT 05201

    Tucked into Bennington's established Spring Hill neighborhood, this inviting 3 bedroom, 2 bath home offers nearly 2,000 square feet of comfortable living space with a setting that makes it easy to enjoy the outdoors. From the backyard, follow the grass walking trail to the community owned pond, a wonderful extension of your outdoor space and a beautiful spot to enjoy the changing Vermont Seasons.

    Faith Rhodes Maple Leaf Real Estate

    291 Springhill Rd, Bennington, VT 05201
  • 751 Main Rd, Stamford, VT 05352
    751 Main Rd, Stamford, VT 05352
    751 Main Rd, Stamford, VT 05352
    /60

    $1,900,000

    • 6 Beds
    • 6 Baths
    • 5,704 Sq Ft

    751 Main Rd, Stamford, VT 05352

    Step into the most amazing Victorian house you will ever see! Built in 1880, you will feel like you've walked back in time. Beautiful architecture and woodwork. The house was built by John Tudor, a Welsh immigrant who had made a fortune as a mill owner in northern Vermont and settled in Stamford. There is a stunning 3 floor Post & Beam Barn built in 2000 with a 2 car garage built-in. Barn also

    Michael Jarvis United Country Real Estate Mike Jarvis Group Inc

    751 Main Rd, Stamford, VT 05352
  • 155 Brookman Rd, Pownal, VT 05261
    155 Brookman Rd, Pownal, VT 05261
    155 Brookman Rd, Pownal, VT 05261
    /37

    $875,000

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

    155 Brookman Rd, Pownal, VT 05261

    Gorgeous setting for this newly constructed home built in 2025, offering breathtaking views from the expansive front porch on 10+/- private acres. Thoughtfully designed with quality craftsmanship throughout, the custom kitchen features beautiful cabinetry, a large center island, gas range, and classic farmhouse sink, all open to the inviting living room with a cozy gas fireplace. The stunning

    Kelley Mccarthy Mahar McCarthy Real Estate

    155 Brookman Rd, Pownal, VT 05261

Showing Results 81 - 120, Page 3 of 5

Vermont

Houses for Sale in Bennington County, VT

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