239

Bennington County VT Homes for Sale

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  • /18

    $79,000

    $30K PRICE DROP
    • Land
    • 17 Acres
    • $4,647 per Acre

    00 Bill T Dr, Readsboro, VT 05350

    Significant price reduction! This gently sloping 17-acre parcel should not be overlooked. This property offers a dead-end location on a town-maintained road, providing you with privacy and convenience. Nestled in the charming town of Readsboro and surrounded by the beautiful Green Mountains, you will have easy access to VAST snowmobile trails and VASA ATV trails. Plus, you are just a stone's

    Michelle O'Neil Deerfield Valley Real Estate

    00 Bill T Dr, Readsboro, VT 05350
  • /12

    $1,295,000

    • Land
    • 52 Acres
    • $24,904 per Acre

    0 Montgomery Rd, Pownal, VT 05261

    A rare opportunity to own one of the most extraordinary parcels in the region. High Meadows Farm encompasses sweeping open meadows, mature woodlands, and truly breathtaking 360-degree views stretching from Mount Greylock to the south, Mount Anthony to the north, the Taconic Ridge to the west, and Dome and Pine Cobble to the east. Wander a secluded birch-lined pathway, discover a magnificent

    Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

    0 Montgomery Rd, Pownal, VT 05261
  • /10

    $125,000

    • Land
    • 5.77 Acres
    • $21,664 per Acre

    0 East Rd, Shaftsbury, VT 05262

    Set along scenic East Road in Shaftsbury, this 5.77-acre wooded parcel offers a beautiful opportunity to create a private Vermont homesite in one of the area’s most appealing rural settings. The land is currently wooded, allowing the next owner to decide how much to clear for a driveway, yard, gardens, or building site, with potential for a mountain view to the north with selective clearing.

    Jenifer Prouty Hoffman Hoffman Real Estate

    0 East Rd, Shaftsbury, VT 05262
  • /49

    $650,000

    • 5 Beds
    • 3 Baths
    • 5,524 Sq Ft

    81 Honeysuckle Ln, North Bennington, VT 05257

    Nestled on 9.89 secluded acres in North Bennington, this exceptional 4-bedroom, 3-bath home offers the perfect blend of character, comfort, and versatility. The sprawling residence features a beautiful interior highlighted by stunning post-and-beam cathedral ceilings and inviting living spaces designed for both everyday living and entertaining. The heart of the home is the large open space

    Kelley Mccarthy Mahar McCarthy Real Estate

    81 Honeysuckle Ln, North Bennington, VT 05257
  • /52

    $895,000

    $75K PRICE DROP
    • 6 Beds
    • 8 Baths
    • 5,764 Sq Ft

    24 Vt Route 11, Londonderry, VT 05148

    Some properties simply hold stories within their walls. Formerly the beloved Nordic Inn, this iconic Landgrove property has been thoughtfully reimagined into a gathering place designed for modern Vermont living while honoring its rich history of hospitality, adventure, and connection. Inside, six ensuite bedrooms, spa-inspired baths, multiple fireplaces, a chef’s kitchen, sun-filled all-season

    Nancy Jensen Four Seasons Sotheby's Int'l Realty

    24 Vt Route 11, Londonderry, VT 05148
  • /37

    $584,900

    • 3 Beds
    • 2.5 Baths
    • 1,786 Sq Ft

    14 Marisa Ln, Dorset, VT 05251

    Welcome to your next chapter in the charming heart of Vermont, where easy living meets thoughtful design in this beautifully crafted one-level duplex townhouse. If you've been dreaming of a home that eliminates stairs from your daily routine while still delivering style and substance, your search ends here. Step inside and discover an open floor plan that feels both spacious and inviting across

    Julie Citron RE/MAX Four Seasons

    14 Marisa Ln, Dorset, VT 05251
  • /19

    $195,000

    • 3 Beds
    • 1 Bath
    • 1,590 Sq Ft

    176 Glen Ave, Readsboro, VT 05350

    Charming and spacious 3-bedroom, 1-bath home situated on approximately 1.90 acres, offering warm character and generous living space. Beautiful wood floors flow throughout the home, complemented by fresh paint, making this property truly move-in ready.The expansive wrap-around porch is a standout feature, perfect for enjoying quiet mornings, relaxing afternoons, or entertaining family and

    Cassandra Ehrlich BHG Masiello Brattleboro

    176 Glen Ave, Readsboro, VT 05350
  • /16

    $495,000

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft

    14 Vaughn Farm Rd Unit 1, Manchester Center, VT 05255

    Breathtaking views of Mount Equinox await from the privacy of this three-bedroom, 2.5-bath end unit condominium, ideally located just minutes from town and the ski mountains. The top floor features a bright loft filled with natural light and a convenient half bath. The spacious living room opens to a private deck with stunning mountain views and includes a cozy wood-burning fireplace.The

    Northshire Sales Group Real Broker LLC

    14 Vaughn Farm Rd Unit 1, Manchester Center, VT 05255
  • /37

    $609,000

    $20K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,050 Sq Ft

    1649 E Manchester Rd, Manchester Center, VT 05255

    LOCATION, LOCATION: Privately set just moments from Manchester’s dining, shopping, golf, year-round recreation, and easy access to Bromley and Stratton, this thoughtfully updated 5-bedroom, 2-bath Cape offers 2,050 sq ft on 0.48 acres—ideal as a primary home, Vermont retreat, or long-term investment. Move-in ready and beautifully maintained, the home balances a peaceful setting with exceptional

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

    1649 E Manchester Rd, Manchester Center, VT 05255
  • /37

    $584,900

    • 3 Beds
    • 2.5 Baths
    • 1,786 Sq Ft

    14A Marisa Ln, Dorset, VT 05251

    Welcome to your next chapter in the charming heart of Vermont, where easy living meets thoughtful design in this beautifully crafted one-level duplex townhouse. If you've been dreaming of a home that eliminates stairs from your daily routine while still delivering style and substance, your search ends here. Step inside and discover an open floor plan that feels both spacious and inviting across

    Julie Citron RE/MAX Four Seasons

    14A Marisa Ln, Dorset, VT 05251
  • /41

    $1,425,000

    $100K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,931 Sq Ft

    932 Mcnamara Rd, Dorset, VT 05251

    Tucked away at the end of a gently curved, tree-lined drive, this exceptional contemporary home blends timeless elegance with Vermont charm. A welcoming paver patio leads to the informal entry, while a marble pathway guides you to the striking formal entrance and grand foyer. Inside, locally sourced marble floors flow into rich cherry hardwoods, setting the tone for quality throughout. Soaring

    Britt Wohler

    932 Mcnamara Rd, Dorset, VT 05251
  • /5

    $374,900

    • Land
    • 2.31 Acres
    • $162,294 per Acre

    0 Wall St, Winhall, VT 05340

    Offered as a set, this property presents a rare opportunity to own two separately deeded parcels in a location that is only minutes from Stratton Mountain yet worlds away from the bustle of the resort. Totaling 2.31 acres, this land is situated high on River Road where neighboring homes enjoy spectacular views of Stratton. The engineering has already been completed, with each lot having a

    Cheyanne Pugliese

    0 Wall St, Winhall, VT 05340
  • /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
  • /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
  • /40

    $5,900,000

    $1M 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 design of 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
  • /10

    $245,000

    $97K PRICE DROP
    • Land
    • 28.5 Acres
    • $8,596 per Acre

    11 Old County Rd E, Londonderry, VT 05148

    A rare opportunity to own a wooded hillside property with potential southern and western views on a quiet country road in the much coveted village of Landgrove. Priced below the town assessment, the land is in current use, affording a tax savings, with a state permit for a 4-bedroom house. Enjoy all the elements of a Vermont country setting including a mix of mature hardwoods and softwoods,

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    11 Old County Rd E, Londonderry, VT 05148
  • /47

    $845,000

    • 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 stunning modern farmhouse seamlessly blends timeless character with thoughtful updates. Rich hardwood floors and cozy alcoves create warmth and charm throughout, while original beams in the living room add a touch of history and authenticity. The spacious layout offers 5 bedrooms, each with

    Kelley Mccarthy Mahar McCarthy Real Estate

    1629 Mann Hill Rd N, Pownal, VT 05261
  • /56

    $2,200,000

    • 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 kitchen

    Christiane Carroccio TPW Real Estate

    312 Beartown Rd, Manchester Center, VT 05255
  • /12

    $299,999

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

    00 Garden Loop Rd, Winhall, VT 05340

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

    David White OwnerEntry.com

    00 Garden Loop Rd, Winhall, VT 05340
  • /45

    $275,000

    $20K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft

    951 Gage St, Bennington, VT 05201

    This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back

    Dan Mason Perrott Realty

    951 Gage St, Bennington, VT 05201
  • /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
  • /7

    $145,000

    $30K PRICE DROP
    • Land
    • 15.49 Acres
    • $9,361 per Acre

    00 Silk Rd, Bennington, VT 05201

    Fifteen and a half level, mowed acres, suitable for a home build, agriculture, or a small subdivision. Passing over the iconic Silk Road Covered Bridge crossing the Walloomsac River, on the right you'll find this flat, cleared parcel ready for farming or development. With over 500 feet of road frontage, plenty of acreage, and the beautiful river across the street, the possibilities here are

    David White OwnerEntry.com

    00 Silk Rd, Bennington, VT 05201
  • /46

    $1,550,000

    • 5 Beds
    • 5 Baths
    • 6,129 Sq Ft

    1035 Holy Smoke Rd, Shaftsbury, VT 05262

    Experience the quintessential Vermont lifestyle in this masterfully renovated (2021) contemporary farmhouse, offering 6,100 sq. ft. of finished living space. Tucked at the end of a breathtaking maple-lined driveway, this 17± acre property offers panoramic mountain views and a private sanctuary for hiking, cross-country skiing, snowshoeing, and snowmobiling right from your door.The heart of

    Lori Hurley Four Corner Properties LLC

    1035 Holy Smoke Rd, Shaftsbury, VT 05262
  • /38

    $625,000

    Open Sat 10AM - 12PM
    • 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
  • /36

    $359,000

    $40K 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
  • /32

    $575,000

    $24K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,234 Sq Ft

    202 Eagle Rise Rd Unit 16, Manchester Center, VT 05255

    This Eagle Rise Condo with three bedrooms and two & half baths is in an exclusive residential area accessed off scenic Manchester West Road. The Condo offers an open floor plan design, central air, propane baseboard hot water heat, hardwood floors and elevated deck. Recent improvements include new kitchen w/ granite counter tops, hickory cabinets with soft close drawers & doors, stainless steel

    David Halligan Four Seasons Sotheby's Int'l Realty

    202 Eagle Rise Rd Unit 16, Manchester Center, VT 05255
  • /12

    $825,000

    $40K PRICE DROP
    • 5,568 Sq Ft

    1931 Vermont Route 67 E, Shaftsbury, VT 05262

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

    Julie Glover Mahar McCarthy Real Estate

    1931 Vermont Route 67 E, Shaftsbury, VT 05262
  • /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
  • /39

    $349,000

    • 4 Beds
    • 2 Baths
    • 1,814 Sq Ft

    1153 King Hill Rd, Readsboro, VT 05350

    This recently updated 1920s Vermont farmhouse features 4 bedrooms, 2 full bathrooms, and a versatile loft space on just over 8 acres! Large, updated windows showcase mountain views and allow natural light to fill every room, highlighting the home's charming original details alongside modern updates. The first floor has two bedrooms, both full bathrooms, first floor laundry, as well as TWO

    Casey Scott Southern Vermont Realty Group

    1153 King Hill Rd, Readsboro, VT 05350
  • /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
  • /55

    $225,000

    • 4 Beds
    • 2 Baths
    • 1,518 Sq Ft

    142 Pine Cir, Bennington, VT 05201

    Opportunity is knocking... answer the door! This home in a sought-after neighborhood on an almost half acre lot is the investment you've been looking for. Close to downtown shopping and dining, as well as the award-winning Southwestern Vermont Medical Center. Features include an attached two car garage, wood floors, mini-split in living room, fireplace, wood floors, dining room, primary bedroom

    Justine Curry Maple Leaf Real Estate

    142 Pine Cir, Bennington, VT 05201
  • /34

    $450,000

    • 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
  • /17

    $160,000

    • Land
    • 2.9 Acres
    • $55,172 per Acre

    Lot 21 Sunderland Hill Rd, West Arlingtn, VT 05250

    This scenic undeveloped lot in Sunderland, Vermont, offers an exceptional opportunity to build in a peaceful yet convenient location. Set along a picturesque bike route, the property features level terrain that makes it ideal for easy construction and design flexibility. The land is already cleared, opening up the possibility for lovely mountain views and allowing you to envision your home

    Andy Reed Four Seasons Sotheby's Int'l Realty

    Lot 21 Sunderland Hill Rd, West Arlingtn, VT 05250
  • /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
  • /33

    $1,100,000

    • 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
  • /12

    $150,000

    $25K PRICE DROP
    • Land
    • 2.26 Acres
    • $66,372 per Acre

    0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340

    Welcome to the Stratton Gardens Community. Build your Vermont home on this 2+ acre parcel in Stratton Gardens. Ease of access right off the Stratton Mountain Access Road, and all the amenities of Stratton Gardens Association- highlights include-Private Shuttle Bus service to the Mountain, Road Maintenance, Plowing, Landscaping, and Trash removal.State Waste Water Permit in place for approved

    Tara van de Velde Four Seasons Sotheby's Int'l Realty

    0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340
  • /25

    $950,000

    $300K PRICE DROP
    • 8,888 Sq Ft

    124 Elm St, Bennington, VT 05201

    An exceptional opportunity to own a prominent historic Victorian property in the heart of Bennington, offered as a residential or multifamily real estate asset only. Built in 1887 by renowned architect William C. Bull, this meticulously restored property offers flexible residential and mixed-use potential within the Village of Bennington, subject to applicable municipal approvals. The main

    Marek Kovac TPW Real Estate

    124 Elm St, Bennington, VT 05201
  • /2

    $2,190,000

    • Land
    • 1.16 Acres
    • $1,887,931 per Acre

    301 Northside Dr, Bennington, VT 05201

    Prime commercial investment opportunity at 301 Northside Drive, Bennington. This 1.16-acre corner lot offers exceptional visibility on a heavily traveled road, making it well-suited for high-exposure commercial uses. Commercial zoning allows for a range of development or redevelopment options. Strategically located near major highways, providing strong regional access and long-term demand

    Paul Carroccio TPW Real Estate

    301 Northside Dr, Bennington, VT 05201
  • /29

    $210,000

    $40K PRICE DROP
    • 9 Beds
    • 5 Baths
    • 3,810 Sq Ft

    6982 Main St, Readsboro, VT 05350

    Prime location meets potential! Situated in the center of charming Readsboro, this 5-unit multi-family property offers a rare opportunity for investors and owner-occupants alike. Whether you're looking to expand your portfolio or live in one unit while generating rental income from the others, this property delivers. Some renovations needed – perfect for those looking to add value and

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    6982 Main St, Readsboro, VT 05350
  • /42

    $279,000

    • 2 Beds
    • 1 Bath
    • 2,142 Sq Ft

    32 Albe Dr, Bennington, VT 05201

    MOVE RIGHT IN AND MAKE YOURSELF AT HOME This beautifully maintained residence is perfect for those looking for the convenience of first floor living. Featuring tastefully painted rooms, bamboo flooring and modern appliances.The kitchen includes a dedicated eating area for family dining while the living room offers a warm and cozy gathering space. Both bedrooms are generously sized with large

    Beatrice O'Connell Maple Leaf Real Estate

    32 Albe Dr, Bennington, VT 05201

Showing Results 121 - 160, Page 4 of 6

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