20,622

Bennington County, VT Homes

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  • /32

    $1,795,000

    • 5 Beds
    • 3 Baths
    • 5,287 Sq Ft

    84 Frost Pond Rd, Dorset, VT 05251

    Tucked away on 12.3 private acres, this move-in-ready contemporary retreat offers the perfect balance of modern design, natural beauty, and effortless single-level living. Adding to its exceptional appeal, the property includes an additional building lot, creating a rare opportunity for a guest house, family compound, future expansion, or investment. Clad in timeless clear cedar siding and

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

    84 Frost Pond Rd, Dorset, VT 05251
  • /59

    $6,500 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,800 Sq Ft
    • House for Rent

    3370 Main St, Manchester, VT 05255

    One of the oldest homes in Manchester Village, dating back to 1763, The Hoyt House is a beautifully revived antique that blends historic Vermont character with comfortable modern living. Ideally located in the heart of Manchester Village, this charming 3-bedroom, 2.5-bath home offers a thoughtfully designed layout. The first floor features a spacious primary suite with a private sitting room and

    Laura Beckwith Josiah Allen Real Estate, Inc.

    3370 Main St, Manchester, VT 05255
  • /25

    $1,200,000

    Sold Jul 30, 2026

    12 Beattie Ln, Manchester, VT 05254

    • 3 Beds
    • 2.5 Baths
    • 2,736 Sq Ft
    • Built 1996

    Last Sold Summary

    • $439/SF
    • 4 Days On Market

    Current Estimated Value $1,016,930

    Last Listing Agent Tatsiana Clark Four Seasons Sotheby's Int'l Realty

    12 Beattie Ln, Manchester, VT 05254
    • /29

      Est $511,214

      Not Listed For Sale

      117 Nottingham Park, Manchester Center, VT 05255

      • 4 Beds
      • 2 Baths
      • 1,728 Sq Ft
      • Built 1972
      117 Nottingham Park, Manchester Center, VT 05255

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent David Halligan Four Seasons Sotheby's Int'l Realty

  • /18

    $249,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,020 Sq Ft

    19 Winhall Condo Rd Unit 1, Winhall, VT 05340

    Here’s your opportunity to have your own mountain retreat just minutes from Stratton. Set at the end of a quiet road less than a mile from the Stratton Access Road, The Winhall Condos provide a peaceful, convenient setting surrounded by Vermont’s natural beauty. Owners enjoy easy access to both Stratton and Manchester and a true sense of privacy. This three-bedroom, two-bath residence offers

    Cheyanne Pugliese

    19 Winhall Condo Rd Unit 1, Winhall, VT 05340
  • /27

    $2,950 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,560 Sq Ft
    • House for Rent

    1377 Old Depot Rd, Shaftsbury, VT 05262

    Built in 2020, this beautiful 3 bedroom, 1.5 bath home offers modern living with quality finishes throughout. The first floor features stunning wood floors, an open-concept kitchen with pantry, spacious living and dining areas, a small office, laundry room, and a convenient half bath. The second floor includes three comfortable bedrooms, a full bathroom, and ample closet space throughout the

    Laura Beckwith Josiah Allen Real Estate, Inc.

    1377 Old Depot Rd, Shaftsbury, VT 05262
  • /2

    $610,000

    Sold Sep 19, 2025

    139 Little John Dr, Manchester Center, VT 05255

    • 4 Beds
    • 2 Baths
    • 2,142 Sq Ft
    • Built 1965

    Last Sold Summary

    • 2% Below List Price
    • $285/SF
    • 0 Days On Market

    Current Estimated Value $639,727

    Last Listing Agent David Shehadi Josiah Allen Real Estate, Inc.

    139 Little John Dr, Manchester Center, VT 05255
    • /12

      Est $384,792

      Not Listed For Sale

      454 NW Hill Rd, Pownal, VT 05261

      • 3 Beds
      • 2 Baths
      • 1,901 Sq Ft
      • Built 1880
      454 NW Hill Rd, Pownal, VT 05261

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  • /39

    $479,000

    $60K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,065 Sq Ft

    262 Dwyers Camp Rd, Shaftsbury, VT 05262

    Well designed and newer home on 10.085 acres in Shaftsbury, VT. Offering 3 bedrooms, including main level primary bedroom and 2 full bathrooms. Cathedral ceiling formal dining room and modern kitchen with dining area and breakfast bar. Large living room with vaulted ceiling and lots of light. Main level laundry and rear mudroom finish the first floor. Upstairs there is a wonderful loft area, 2

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    262 Dwyers Camp Rd, Shaftsbury, VT 05262
  • /15

    $3,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • Apartment for Rent

    48 Della St, Manchester, VT 05255

    Highland Farm is Manchester's newest residential living option. New construction on Highland Avenue. Elevator served two bedroom, two bathroom apartment. Large kitchen open to living/dining area. Laundry room in the unit. Individually metered utilities. Underground heated parking garage with assigned parking. Contact the owner/Realtor for additional information.

    Christiane Carroccio TPW Real Estate

    48 Della St, Manchester, VT 05255
  • /39

    $289,000

    Sold Apr 14, 2026

    51 Russell St Unit D, Arlington, VT 05250

    • 2 Beds
    • 1.5 Baths
    • 1,417 Sq Ft
    • Built 1987

    Last Sold Summary

    • 3% Below List Price
    • $204/SF
    • 148 Days On Market

    Current Estimated Value $314,685

    Last Listing Agent Robert Sabol Wohler Realty Group

    51 Russell St Unit D, Arlington, VT 05250
    • /35

      Est $279,680

      Not Listed For Sale

      312 School St Unit 314, Bennington, VT 05201

      • 4 Beds
      • 2 Baths
      • 2,184 Sq Ft
      • Built 1908
      312 School St Unit 314, Bennington, VT 05201

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Angela Bevin Maple Leaf Real Estate

  • /10

    $109,000

    • Land
    • 30.8 Acres
    • $3,539 per Acre

    0 Old Gale Hill Rd Unit 5099471, Shaftsbury, VT 05262

    30 acres of Vermont Heaven located on a private road just 20 minutes from the center of Shaftsbury . There is a mix of hardwoods, evergreens and wet lands around the pond. this is suitable for a dry camp. A slice paradise to get away to in the Green Mountains just steps away from the National Forest.

    Dan Mason Perrott Realty

    0 Old Gale Hill Rd Unit 5099471, Shaftsbury, VT 05262
  • /48

    $45,000 Per Month

    • 4 Beds
    • 4 Baths
    • 5,624 Sq Ft
    • House for Rent

    37 Burnt Hill Rd, Winhall, VT 05340

    Now available for the 26-27 ski season! This spacious, luxurious post-and-beam mountain home has been owner-occupied for past winter weekends, and is now available as the ultimate ski rental just a 7-minute drive to Stratton's base lodge. Beginning with the property's 2-car garage-barn, enviable curb appeal extends throughout. An expansive, well-equipped chef's kitchen offers duel ranges and

    Jamie Luke TPW Real Estate

    37 Burnt Hill Rd, Winhall, VT 05340
  • /41

    $410,000

    Sold Oct 17, 2025

    882 East Rd, Bennington, VT 05201

    • 3 Beds
    • 2.5 Baths
    • 1,792 Sq Ft
    • Built 2002

    Last Sold Summary

    • 3% Above List Price
    • $229/SF
    • 14 Days On Market

    Current Estimated Value $416,039

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    882 East Rd, Bennington, VT 05201
    • /34

      Est $481,290

      Not Listed For Sale

      647 Fox Hill Rd, Bennington, VT 05201

      • 4 Beds
      • 2.5 Baths
      • 1,901 Sq Ft
      • Built 2008
      647 Fox Hill Rd, Bennington, VT 05201

      Last Sold Summary

      • 133 Days On Market

      Last Listing Agent Erika Floriani Hoffman Real Estate

  • /29

    $250,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,824 Sq Ft

    103 Jennings Brook Dr, Bennington, VT 05201

    Located in the desirable Jennings Brook community, this condominium offers a wonderful opportunity to add your own personal touches while enjoying a convenient Bennington location. The spacious living room features a cozy fireplace, beautiful built-ins, and abundant natural light, while the large dining room provides an ideal setting for gatherings and entertaining. The foyer is currently used as

    Kelley Mccarthy Mahar McCarthy Real Estate

    103 Jennings Brook Dr, Bennington, VT 05201
  • /54

    $4,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,189 Sq Ft
    • Condo for Rent

    94 Murray Hill Woods Rd Unit 64, Manchester, VT 05255

    Enjoy mountain living in this spacious 3 bedroom, 3 bath end-unit condo at Murray Hill, offering 2,139 SF of comfortable living space and beautiful mountain views. The main level features an open-concept floor plan with a welcoming foyer, kitchen, dining area, and living room, along with a convenient half bath. The spacious layout is ideal for both everyday living and entertaining. Upstairs, the

    Laura Beckwith Josiah Allen Real Estate, Inc.

    94 Murray Hill Woods Rd Unit 64, Manchester, VT 05255
  • /19

    $89,499

    Sold Jan 21, 2026

    64 Ethans Way, Bennington, VT 05201

    • 2 Beds
    • 1 Bath
    • 746 Sq Ft
    • Built 2024

    Last Sold Summary

    • $120/SF
    • 238 Days On Market

    Last Listing Agent Kate Barry EXP Realty

    64 Ethans Way, Bennington, VT 05201
    • /39

      Est $586,127

      Not Listed For Sale

      557 Fox Hill Rd, Bennington, VT 05201

      • 4 Beds
      • 3.5 Baths
      • 2,336 Sq Ft
      • Built 2009
      557 Fox Hill Rd, Bennington, VT 05201

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  • /45

    $449,000

    $46K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,382 Sq Ft

    298 Mad Tom Rd, Dorset, VT 05253

    Set on over half an acre in the heart of East Dorset Village, this newly renovated three-bedroom, two-bath bungalow blends modern upgrades with cozy charm and even includes a peaceful brook running through the property. Recent upgrades include completely new kitchen and bathrooms and fresh interior paint throughout. The open-concept layout creates a bright,connected space that’s perfect for

    David Halligan Four Seasons Sotheby's Int'l Realty

    298 Mad Tom Rd, Dorset, VT 05253
  • /34

    $45,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 3,600 Sq Ft
    • House for Rent

    43 Cranberry Hill Rd, Winhall, VT 05340

    This tres chic classic chalet has been fully renovated and decorated with a modern and classy flair. The main living area has an open kitchen, dining and living concept design. With two additional living and gathering areas, there is plenty of room for family and friends to have conversation. Complete with a pool table, a built-in sofa suitable for extra sleeping, a meticulously designed mudroom

    Peggy O'neill Cummings & Co

    43 Cranberry Hill Rd, Winhall, VT 05340
  • /22

    $675,000

    Sold May 01, 2026

    201 Owls Head Hill Ln, Dorset, VT 05251

    • 3 Beds
    • 2.5 Baths
    • 2,400 Sq Ft
    • Built 2005

    Last Sold Summary

    • 13% Below List Price
    • $281/SF
    • 34 Days On Market

    Current Estimated Value $396,518

    Last Listing Agent Annette Gallo Real Broker LLC

    201 Owls Head Hill Ln, Dorset, VT 05251
    • /38

      Est $711,593

      Not Listed For Sale

      3347 West Rd, Bennington, VT 05201

      • 5 Beds
      • 3 Baths
      • 3,266 Sq Ft
      • Built 1969
      3347 West Rd, Bennington, VT 05201

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Margretta Fischer Wohler Realty Group

  • /33

    $250,000

    • 2 Beds
    • 1 Bath
    • 1,504 Sq Ft

    252 Tudor Rd, Arlington, VT 05250

    Got a toolbelt, a dangerous amount of Pinterest boards, and an active imagination? It’s your time to shine! Tucked away on 3.52 blissfully serene, wooded acres in beautiful Sandgate, this rural retreat is the dictionary definition of a "diamond in the rough" just waiting for your grand vision! Born in 1983 and being sold "as-is", this ranch has fantastic bones. The main house is completely

    TG Glazer Winhall Real Estate

    252 Tudor Rd, Arlington, VT 05250
  • /28

    $716,845

    Sold Jun 26, 2026

    21 Burnt Hill Rd, Winhall, VT 05341

    • 4 Beds
    • 2 Baths
    • 2,055 Sq Ft
    • Built 1978

    Last Sold Summary

    • 2% Below List Price
    • $349/SF
    • 11 Days On Market

    Last Listing Agent Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    21 Burnt Hill Rd, Winhall, VT 05341
    • /38

      Not Listed For Sale

      639 Shippee Rd, Readsboro, VT 05350

      • 2 Beds
      • 1.5 Baths
      • 1,008 Sq Ft
      • Built 2008
      639 Shippee Rd, Readsboro, VT 05350

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Monique White Deerfield Valley Real Estate

  • /25

    $795,000

    $20K PRICE INCREASE Under Contract
    • 3 Beds
    • 3.5 Baths
    • 2,484 Sq Ft

    263 Kestrel Ct Unit F-17, Manchester, VT 05255

    Villager Unit at Equinox on the Battenkill adjacent to the 16th hole of the Equinox Golf Course! This stunning property offers a harmonious blend of luxury and comfort in a picturesque setting. Spacious living, dining, and kitchen areas with granite countertops, stainless steel appliances, and a convenient walk-in pantry. Enjoy the wood-burning fireplace, perfect for cozy evenings. Hardwood

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

    263 Kestrel Ct Unit F-17, Manchester, VT 05255
  • /23

    $545,000

    Sold Aug 07, 2026

    144 Oak Knoll Rd, Arlington, VT 05250

    • 3 Beds
    • 2 Baths
    • 1,715 Sq Ft
    • Built 1973

    Last Sold Summary

    • 1% Below List Price
    • $318/SF
    • 4 Days On Market

    Current Estimated Value $495,829

    Last Listing Agent Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

    144 Oak Knoll Rd, Arlington, VT 05250
    • /19

      Est $413,793

      Not Listed For Sale

      1 Division Place, Bennington, VT 05201

      • 3 Beds
      • 1 Bath
      • 975 Sq Ft
      • Built 1895
      1 Division Place, Bennington, VT 05201

      Last Sold Summary

      • 44 Days On Market

      Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  • /14

    $224,000

    $14K PRICE DROP
    • 1,222 Sq Ft

    117 Putnam St, Bennington, VT 05201

    This beautifully renovated 2-unit home by JDN Properties offers exceptional flexibility for buyers, allowing for a variety of living arrangements to suit your needs. Whether you choose to enjoy it as a spacious two-story single family residence with a luxurious upstairs primary suite and kitchenette, use it as an owner-occupied property with a rental unit to help offset your mortgage, or maximize

    Dan Mason Perrott Realty

    117 Putnam St, Bennington, VT 05201
  • /15

    $380,000

    Sold Oct 15, 2025

    0 Tower Rd Unit 28, Dorset, VT 05251

    • Land
    • 16 Acres
    • $23,750 per Acre

    Last Sold Summary

    • 1% Below List Price
    • 0 Days On Market

    Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.

    0 Tower Rd Unit 28, Dorset, VT 05251
    • /27

      Est $286,953

      Not Listed For Sale

      239 Breezy Acres Dr, Vernon, VT 05354

      • 3 Beds
      • 1.5 Baths
      • 1,941 Sq Ft
      • Built 1992
      239 Breezy Acres Dr, Vernon, VT 05354

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent A.J. Bellville Bellville Realty

  • /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
  • /35

    $165,000

    Sold Aug 18, 2025

    250 Magee Rd, Stamford, VT 05352

    • 4 Beds
    • 1 Bath
    • 952 Sq Ft
    • Built 2010

    Last Sold Summary

    • 2% Below List Price
    • $173/SF
    • 179 Days On Market

    Current Estimated Value $164,534

    Last Listing Agent Susan Colvin MONARCH REALTY, INC.

    250 Magee Rd, Stamford, VT 05352
    • /26

      Est $394,809

      Not Listed For Sale

      183 Cross Rd, Manchester Center, VT 05255

      • 2 Beds
      • 1 Bath
      • 864 Sq Ft
      • Built 1980
      183 Cross Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 98 Days On Market

      Last Listing Agent Mike England Michael England Real Estate

  • /43

    $619,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,692 Sq Ft

    34 Monument Ave, Bennington, VT 05201

    Set along tree-lined Monument Avenue in prestigious and historic Old Bennington, the Spargo House offers a rare opportunity to own a distinctive piece of Vermont history. Dating to circa 1800, this remarkable home was once the longtime residence of noted author, historian and collector John Spargo, founder and longtime director of the Bennington Museum. Just below the Bennington Battle Monument,

    Jeffrey Dorman

    34 Monument Ave, Bennington, VT 05201
  • /29

    $410,000

    Sold Jul 31, 2026

    2121 North Rd, Arlington, VT 05250

    • 3 Beds
    • 2 Baths
    • 1,920 Sq Ft
    • Built 1973

    Last Sold Summary

    • 9% Below List Price
    • $214/SF
    • 22 Days On Market

    Current Estimated Value $446,682

    Last Listing Agent Matt Waddington Hoffman Real Estate

    2121 North Rd, Arlington, VT 05250
    • /21

      Est $173,539

      Not Listed For Sale

      106 Park St Unit 16, Bennington, VT 05201

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1993
      106 Park St Unit 16, Bennington, VT 05201

      Last Sold Summary

      • 76 Days On Market

      Last Listing Agent Peggy Winchester ACORN REAL ESTATE GROUP LLC

  • /28

    $209,900

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft

    107 Jefferson Ave, Bennington, VT 05201

    Terrific in town location for this 3 bedroom, 2 bathroom home in Bennington. Offering living room, large kitchen, formal dining room and office/study. Covered porch and patio. Privacy bushes and yard. Property is being sold "as-is".

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    107 Jefferson Ave, Bennington, VT 05201

Showing Results 161 - 200, Page 5 of 18

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