21,041

Bennington County, VT Homes

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  • /15

    $269,000

    • 2 Beds
    • 1 Bath
    • 2,500 Sq Ft

    624 Main St, Bennington, VT 05201

    Prime Mixed-Use Building on Main Street-Bennington, Vermont. Located in the heart of downtown Bennington, this versatile mixed-use property offers an excellent opportunity for both investors and owner-occupants. The main level features a spacious, adaptable commercial space ideal for retail, office, or service-based businesses. With its high visibility and foot traffic on Main Street, this is a

    Kelley Mccarthy Mahar McCarthy Real Estate

    624 Main St, Bennington, VT 05201
  • /19

    $241,000 Sold Sep 25, 2025

    • 1,070 Sq Ft
    • $225/SF
    • 4 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1990

    20 Rockwood St, Bennington, VT 05201

    As sweet and tidy as can be, this 3BR/1BA home on a residential street offers one level living just outside of town. Gleaming wood floors in the living room and kitchen; kitchen is efficiently laid out and the dining area opens out to a deck overlooking the landscaped back yard and creates a private retreat for your morning coffee. Full basement has been partially finished with a room perfect

    Vicki Wilson Maple Leaf Realty

    20 Rockwood St, Bennington, VT 05201
    • /21

      Est $263,587 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,196 Sq Ft

      470 Alpenwald Ln Unit A57, Readsboro, VT 05350

      470 Alpenwald Ln Unit A57, Readsboro, VT 05350
  • /51

    $269,000

    • 2 Beds
    • 1 Bath
    • 1,400 Sq Ft

    3264 Route 153, West Rupert, VT 05776

    This neat and tidy single story home has been completely renovated from top to bottom, offering comfort, efficiency, and style. Updates include all new metal roof, vinyl siding, thermopane windows, propane hot-air heating system with heat pump central air conditioning, appliances, kitchen cabinets, counters, and hardwood flooring. Also updated plumbing, fiber optic internet, new electrical with a

    Scott McChesney McChesney RE, Inc.

    3264 Route 153, West Rupert, VT 05776
  • /20

    $89,499 Sold Sep 24, 2025

    • 825 Sq Ft
    • $108/SF
    • 120 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 2024

    72 Ethans Way, Bennington, VT 05201

    Welcome to 72 Ethans Way, Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Lewis model manufactured home offers 2 bedrooms, 2 bathroom, and 825 sq. ft. (16 x 56 ft.) 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

    72 Ethans Way, Bennington, VT 05201
    • /28

      Est $332,665 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,751 Sq Ft

      469 Swallow Hill Rd, Pownal, VT 05261

      469 Swallow Hill Rd, Pownal, VT 05261
  • /4

    $39,500

    • Land
    • 2 Acres
    • $19,750 per Acre

    0 Oberhugel Rd Unit 5059139, Stamford, VT 05352

    Here are 2 beautiful wooded lots high on the mountain! Perfect opportunity for you to create your paradise in southern Vermont! Alpenwald is a hidden gem - a community on a mountain across from an old ski area which has been repurposed for Backcountry skiing and hiking. Alpenwald also has direct access to the VAST trail network as well as ATV trails. It is also not far from ski areas such as MT

    Duncan Honig Maple Leaf Realty

    0 Oberhugel Rd Unit 5059139, Stamford, VT 05352
  • /47

    $240,000 Sold Sep 24, 2025

    • 2,404 Sq Ft
    • $100/SF
    • 114 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1895

    120 Imperial Ave, Bennington, VT 05201

    Nestled in the charming village of Bennington, Vermont, this stately 4-bedroom, 2.5-bath home blends timeless elegance with thoughtful updates. Built in 1895 and set on 0.41 acres, the property offers a rare combination of historic character and modern livability. A large Trex front deck with handicap accessible ramp to the front and kitchen doors welcomes you to the home, where you'll find

    Kelley Mccarthy Mahar McCarthy Real Estate

    120 Imperial Ave, Bennington, VT 05201
    • /39

      Est $383,801 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,208 Sq Ft

      375 Grapevine Ln, Pownal, VT 05261

      375 Grapevine Ln, Pownal, VT 05261
  • /26

    $194,900

    • 4 Beds
    • 2 Baths
    • 1,278 Sq Ft

    215 Maple St, Bennington, VT 05201

    Huge Price Reduction. Enjoy the charm and comfort of this beautifully renovated home, ideally nestled in the heart of Bennington. As you arrive, you'll be greeted by a spacious front porch, perfect for relaxation, entertaining, and enjoying cool breezes. This property has undergone a complete transformation from a two-family to a stunning single-family home. It now offers convenient one-floor

    Matt Waddington Hoffman Real Estate

    215 Maple St, Bennington, VT 05201
  • /4

    $96,906 Sold Sep 24, 2025

    • 777 Sq Ft
    • $125/SF
    • 26 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2025

    29 Dustin Dr, Bennington, VT 05201

    Welcome to 29 Dustin Drive, 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

    29 Dustin Dr, Bennington, VT 05201
    • /38

      Est $328,315 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,188 Sq Ft

      205 W Meadow Ct, Pownal, VT 05261

      205 W Meadow Ct, Pownal, VT 05261
  • /22

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    3 Kimball Hill Rd Unit 1, Winhall, VT 05340

    Escape to the mountains in this charming A-frame, ideally located between the bustling town of Manchester and the area's best ski mountains. This home is your perfect base for year-round adventure, putting you just minutes from world-class skiing, hiking, mountain biking, and shopping.Inside, you'll find a comfortable layout featuring 3 bedrooms, 2 bathrooms, and a home office that can

    Robin Apps Four Seasons Sotheby's Int'l Realty

    3 Kimball Hill Rd Unit 1, Winhall, VT 05340
  • /38

    $370,000 Sold Sep 23, 2025

    • 1,809 Sq Ft
    • $205/SF
    • 59 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1964

    366 Clough Rd, Stamford, VT 05352

    Southern Vermont country home, right over the border of Berkshire County, MA. Centrally located between major ski areas in Vermont and MA this home is also just a short drive to all cultural attractions in Berkshire County (MassMoCA, The Clark, Hancock Shaker Village). Bordering the North Branch of the Hoosic River, the property offers river frontage and expansive views of the beautiful Green

    Debra Burchard OLD COUNTY PROPERTIES

    366 Clough Rd, Stamford, VT 05352
    • /37

      Est $259,611 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,064 Sq Ft

      195 W Meadow Ct, Pownal, VT 05261

      195 W Meadow Ct, Pownal, VT 05261
  • /56

    $1,849,000

    • 3 Beds
    • 2.5 Baths
    • 3,450 Sq Ft

    139 Prospect St, Manchester, VT 05254

    Set against Equinox Mountain and just minutes from the thriving center of Manchester, this timeless and elegant home has been thoughtfully renovated to honor age-old craftsmanship while embracing modern building science to create a beautiful, healthy, and inviting space. Recent renovations include a comprehensive rebuild and expansion of the upper floor, Marvin windows and patio doors, charming

    Cheyanne Pugliese

    139 Prospect St, Manchester, VT 05254
  • /56

    $385,000 Sold Sep 23, 2025

    • 1,702 Sq Ft
    • $226/SF
    • 156 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2024

    321 Chester Knoll Dr, Bennington, VT 05201

    Low maintenance lifestyle awaits~This new construction three bedroom two bath cape style home is energy efficient and up to the newest Vermont energy codes. On demand hot water and energy efficient heat system. Not only do you get brand new construction, but you have an option for one level living with living room, kitchen, dining, laundry, bedroom, and full bath all on one level. Upstairs has

    Lilli West Maple Leaf Realty

    321 Chester Knoll Dr, Bennington, VT 05201
    • /40

      Est $378,032 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,052 Sq Ft

      46 Grapevine Ln, Pownal, VT 05261

      46 Grapevine Ln, Pownal, VT 05261
  • /40

    $1,525,000

    • 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

    Britt Wohler

    932 Mcnamara Rd, Dorset, VT 05251
  • /53

    $400,000 Sold Sep 22, 2025

    • 1,309 Sq Ft
    • $306/SF
    • 12 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2006

    495 Fairview St, Bennington, VT 05201

    This charming cape style home is close to town yet enjoys a sense of rural privacy. There is an open floor plan for entertaining on the first floor as well as two bedrooms and a bath. The wood stove keeps you cozy on those cold winter evenings. The second floor is a primary suite with large bath including a claw foot soaking tub and walk-in closet. Access to the full basement via the

    Catherine Cairns Maple Leaf Realty

    495 Fairview St, Bennington, VT 05201
    • /27

      Est $553,954 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,160 Sq Ft

      503 Atwood Dr, Pownal, VT 05261

      503 Atwood Dr, Pownal, VT 05261
  • /17

    $85,000

    • Land
    • 9.74 Acres
    • $8,727 per Acre

    1 & 2 Joy Ln, Arlington, VT 05250

    Two Perked and Permitted Building Lots tucked away in the village of Arlington. Survey and Waste Water Permit available for two lots totaling 9.74 acres. These two Joy Lane lots are ready for your vision and your dreams. Close to town and all amenities, however private. Opportunity awaits to build one house or two. Owners are selling both lots together. The next owner could build on one lot and

    Margretta Fischer Wohler Realty Group

    1 & 2 Joy Ln, Arlington, VT 05250
  • /60

    $245,000 Sold Sep 22, 2025

    • 1,320 Sq Ft
    • $186/SF
    • 3 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1954

    19 Robinson Ave, Bennington, VT 05201

    This charming 3-bedroom, 1 bathroom ranch features one-level living. The updated gallery-style eat-in kitchen offers plenty of space and storage and leads into a spacious living room where you'll enjoy a large bay window and fireplace. Enjoy the beautiful hardwood floors throughout the bedrooms and hallways, which lead into a newly renovated full bath. There's a full basement which offers options

    Floyd Amidon Maple Leaf Realty

    19 Robinson Ave, Bennington, VT 05201
    • /38

      Est $409,879 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,936 Sq Ft

      218 Puddingstone Rd, Pownal, VT 05261

      218 Puddingstone Rd, Pownal, VT 05261
  • /29

    $250,000

    • 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
  • /19

    $199,900 Sold Sep 19, 2025

    • 952 Sq Ft
    • $210/SF
    • 28 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1964

    42 Colvin Ave, Shaftsbury, VT 05262

    Discover comfortable single-level living in this well-maintained ranch-style home, perfectly situated on a 0.16-acre lot. Has 952 square feet, this residence offers three bedrooms and one full bathroom—ideal for families, first-time buyers, or those looking to downsize without compromising on style or functionality.Step inside to be greeted by hardwood floors that flow seamlessly

    Timothy Corcoran Mahar McCarthy Real Estate

    42 Colvin Ave, Shaftsbury, VT 05262
    • /21

      Est $242,877 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,196 Sq Ft

      91 Valley View Dr, Pownal, VT 05261

      91 Valley View Dr, Pownal, VT 05261
  • /36

    $224,500

    • 5 Beds
    • 2 Baths
    • 2,212 Sq Ft

    1138 Main Rd, Stamford, VT 05352

    Stamford, VT - A country drive less than 10 minutes North Adams, MA- home of Mass MoCA. Dating back to 1850 this spacious home boasts 4 bedrooms & 2 baths. 1st floor bedroom, bath, laundry, kitchen, dining, living room, den & sunroom. Nestled on almost and acre of land and bordering a babbling brook this property offers a privacy sanctuary. Come take a look for yourself! Located close to

    Colleen Zajac MONARCH REALTY, INC.

    1138 Main Rd, Stamford, VT 05352
  • /33

    $355,000 Sold Sep 19, 2025

    • 2,072 Sq Ft
    • $171/SF
    • 22 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1948

    60 Knoll Crest Ln, Bennington, VT 05201

    Step into this well maintained brick and clapboard residence, perfectly nestled in a lovely neighborhood. Just minutes from the hospital and a short, pleasant walk to downtown, this home offers the best of both convenience and community.Bathed in natural light, the interior boasts an inviting and functional layout highlighted by gleaming hardwood floors and timeless character throughout.

    Moira Spivey Four Seasons Sotheby's Int'l Realty

    60 Knoll Crest Ln, Bennington, VT 05201
    • /16

      Est $132,283 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft

      86 Floyds Way, Pownal, VT 05261

      86 Floyds Way, Pownal, VT 05261
  • /37

    $999,000

    • 4 Beds
    • 3.5 Baths
    • 2,280 Sq Ft

    17 Roundtree Rd, Winhall, VT 05340

    Contemporary ski chalet on shuttle route located on a short cul-de-sac in the coveted North Brookwood neighborhood, a stone's throw from the Stratton base lodge. This 4 bedroom, 3 1⁄2 bath home boasts an open plan, walls of windows, and floor-to-ceiling stone fireplace in the Great Room. The pass-through kitchen was fully renovated in 2021 in addition to many other upgrades. Test your skills at

    Sarah Nichols Winhall Real Estate

    17 Roundtree Rd, Winhall, VT 05340
  • /3

    $26,000 Sold Sep 19, 2025

    • Land
    • 1.1 Acres
    • $23,636 per Acre
    • 656 Days On Market

    0 Deepwoods Rd Unit 4976604, Winhall, VT 05340

    Discover the perfect spot for your next adventure with this prime piece of land in Winhall. Imagine placing a charming tiny home on this property and owning your own slice of Vermont paradise. The land comes with preliminary septic design information, making it easier for you to start your new chapter. Enjoy the best of all worlds: live amidst the breathtaking mountains in a cozy, manageable

    Andrea Kaplan Four Seasons Sotheby's Int'l Realty

    0 Deepwoods Rd Unit 4976604, Winhall, VT 05340
    • /40

      Est $806,593 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,879 Sq Ft

      718 Montgomery Rd, Pownal, VT 05261

      718 Montgomery Rd, Pownal, VT 05261
  • /46

    $805,000

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

    392 Powderhorn Rd, Manchester Center, VT 05255

    Set on two private acres in a desirable Manchester location, this renovated four-bedroom, three-bath Colonial offers a quiet retreat with convenient access to both Manchester and Dorset. Wide-plank pine floors and abundant natural light define the interiors, creating an inviting flow throughout. The main level includes a spacious living room with a stone fireplace, a formal dining room,

    Alexandra Crowley Four Seasons Sotheby's Int'l Realty

    392 Powderhorn Rd, Manchester Center, VT 05255
  • /25

    $101,968 Sold Sep 19, 2025

    • 825 Sq Ft
    • $124/SF
    • 125 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2024

    86 Ethans Way Unit Lot 86E, Bennington, VT 05201

    Welcome to 78 86 Ethans Way, Lot 86E Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Polo model manufactured home offers 2 bedrooms, 2 bathrooms, and 825 sq. ft. 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

    86 Ethans Way Unit Lot 86E, Bennington, VT 05201
    • /19

      Est $210,799 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 960 Sq Ft

      169 Montgomery Rd, Pownal, VT 05261

      169 Montgomery Rd, Pownal, VT 05261
  • /38

    $749,000

    • 3 Beds
    • 2.5 Baths
    • 4,683 Sq Ft

    2744 Danby Mountain Rd, Dorset, VT 05251

    This classic Vermont mountain retreat offers the perfect blend of comfort, privacy, and year-round recreation. Located just minutes from Dorset Village and Manchester, the property is surrounded by adventure—ski touring, snowshoeing, and hiking are all available right from your yard. A new wrap-around Trex deck invites you to unwind or dine outdoors while taking in views of the gardens and

    Andie Fusco Four Seasons Sotheby's Int'l Realty

    2744 Danby Mountain Rd, Dorset, VT 05251
  • /22

    $795,000 Sold Sep 17, 2025

    • 3,463 Sq Ft
    • $230/SF
    • 9 Days On Market
    • 4 Beds
    • 5.5 Baths
    • Built 2006

    185 Crooked Path Rd, Arlington, VT 05250

    A Vermont Escape in Picturesque ArlingtonWelcome to your dream getaway nestled in the heart of the Green Mountains, a beautifully appointed 4-bedroom, 5.5-bathroom estate offering the perfect blend of rustic charm and modern luxury. Each spacious bedroom features its own private en-suite bath, providing ultimate comfort and privacy for family and guests. The open-concept kitchen is fully

    Andrea Kaplan Four Seasons Sotheby's Int'l Realty

    185 Crooked Path Rd, Arlington, VT 05250
    • /52

      Est $229,796 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,378 Sq Ft

      351 Old Military Rd, Pownal, VT 05261

      351 Old Military Rd, Pownal, VT 05261
  • /8

    $59,000

    • Land
    • 0.29 Acre
    • $203,448 per Acre

    420 Burgess Rd, Bennington, VT 05201

    Level building lot with town sewer and water at the edge of town.Possible owner financing.

    Dan Mason Perrott Realty

    420 Burgess Rd, Bennington, VT 05201

Showing Results 401 - 440, Page 11 of 18

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