20,610

Bennington County, VT Homes

Section Image
  • /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
  • /59

    $949,000

    Sold Jul 10, 2026

    178 High Meadow Rd, Winhall, VT 05340

    • 5 Beds
    • 3.5 Baths
    • 4,000 Sq Ft
    • Built 1987

    Last Sold Summary

    • 6% Above List Price
    • $237/SF
    • 6 Days On Market

    Current Estimated Value $913,695

    Last Listing Agent Terry Hill Berkshire Hathaway HomeServices Stratton Home

    178 High Meadow Rd, Winhall, VT 05340
    • /25

      Est $533,441

      Not Listed For Sale

      256 Hillcrest Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 1,731 Sq Ft
      • Built 1986
      256 Hillcrest Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 77 Days On Market

      Last Listing Agent Katherine Zilkha Four Seasons Sotheby's Int'l Realty

  • /18

    $795,000

    Under Contract
    • 3 Beds
    • 3.5 Baths
    • 2,660 Sq Ft

    437 Equinox On the Battenkill Unit H-5, Manchester, VT 05254

    Enjoy breathtaking mountain views from this beautifully renovated end-unit townhome, ideally situated at the top of the sought-after EOB neighborhood. This special property offers a rare sense of privacy along with sweeping vistas of both the Green Mountains and the Taconic Range.A charming garden entrance welcomes you home. Inside, the updated kitchen opens to a spacious deck with awning

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

    437 Equinox On the Battenkill Unit H-5, Manchester, VT 05254
  • /59

    $3,200,000

    Sold Jun 08, 2026

    220 Camptown Rd, Manchester Center, VT 05255

    • 5 Beds
    • 4.5 Baths
    • 5,905 Sq Ft
    • Built 1988

    Last Sold Summary

    • 8% Below List Price
    • $542/SF
    • 24 Days On Market

    Current Estimated Value $3,307,864

    Last Listing Agent Christiane Carroccio TPW Real Estate

    220 Camptown Rd, Manchester Center, VT 05255
    • /21

      Est $493,358

      Not Listed For Sale

      172 Carlen St, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 2,400 Sq Ft
      • Built 1984
      172 Carlen St, Manchester Center, VT 05255

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Andy Reed Four Seasons Sotheby's Int'l Realty

  • /38

    $575,000

    $10K PRICE DROP
    • 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
  • /26

    $290,000

    Sold Mar 26, 2026

    235 Elm St Unit 3, Bennington, VT 05201

    • 6 Beds
    • 3 Baths
    • 2,640 Sq Ft
    • Built 1880

    Last Sold Summary

    • 2% Below List Price
    • $110/SF
    • 8 Days On Market

    Current Estimated Value $293,367

    Last Listing Agent Erica Hale Ridgeline Real Estate

    235 Elm St Unit 3, Bennington, VT 05201
    • /41

      Est $599,780

      Not Listed For Sale

      1565 E Manchester Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 2,088 Sq Ft
      • Built 1967
      1565 E Manchester Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Jessica Citera Cummings & Co

  • /60

    $1,600,000

    • 5 Beds
    • 4.5 Baths
    • 4,243 Sq Ft

    397 Fern Hill, Dorset, VT 05251

    Take a drive up Nichols Hill Road to Fern Hill and head to the very top of the long bending driveway to find a serene, picturesque artist’s retreat 3 minutes from historic Dorset Village. Refreshingly private, quiet and secluded, drenched in natural light. With broad mountain vistas of Mother Myrick and Merck Forest, the top of the property backs gently into a beautiful private forest. The entire

    Laura Beckwith Josiah Allen Real Estate, Inc.

    397 Fern Hill, Dorset, VT 05251
  • /18

    $286,000

    Sold Jun 12, 2026

    124 Albe Dr, Bennington, VT 05201

    • 2 Beds
    • 1 Bath
    • 1,104 Sq Ft
    • Built 2000

    Last Sold Summary

    • 4% Above List Price
    • $259/SF
    • 3 Days On Market

    Current Estimated Value $275,689

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    124 Albe Dr, Bennington, VT 05201
    • /45

      Est $753,878

      Not Listed For Sale

      327 Deer Meadow Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2.5 Baths
      • 2,432 Sq Ft
      • Built 1971
      327 Deer Meadow Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 55 Days On Market

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

  • /41

    $1,425,000

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

    932 Mcnamara Rd, Dorset, VT 05251

    It's SUMMER in Dorset and Manchester Vermont and this home screams opportunity ! NEW ROOF and exterior maintenance all updated for new owner! Situated in a most beautiful 5.4 acre setting of mature trees, landscaping and privacy, tucked away at the end of a gently curved, tree-lined drive. Located just over the Manchester Dorset town line, where Three Maple Drive becomes MacNamara, you'll

    Britt Wohler

    932 Mcnamara Rd, Dorset, VT 05251
  • /59

    $720,000

    Sold Sep 12, 2025

    422 N Mason Hill Rd, Pownal, VT 05261

    • 4 Beds
    • 4 Baths
    • 4,844 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Below List Price
    • $149/SF
    • 5 Days On Market

    Current Estimated Value $736,487

    Last Listing Agent Vicki Wilson Maple Leaf Real Estate

    422 N Mason Hill Rd, Pownal, VT 05261
    • /11

      Est $638,962

      Not Listed For Sale

      470 Johnnycake St, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 1,576 Sq Ft
      • Built 1950
      470 Johnnycake St, Manchester Center, VT 05255

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Katherine Zilkha Four Seasons Sotheby's Int'l Realty

  • /32

    $1,275,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,814 Sq Ft

    19 Maple Hill Rd, Winhall, VT 05340

    Beautifully renovated in 2023, this 4-bedroom, 2-1/2 bathroom contemporary sits on 1.47 wooded acres with a sweeping circular driveway and genuine privacy — while still being on the Stratton shuttle route and just minutes from the base lodge on foot. The interior renovation was done right. Radiant heat floors run through the living room and kitchen, with two wood-burning fireplaces anchoring the

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    19 Maple Hill Rd, Winhall, VT 05340
  • /43

    $115,000

    Sold Aug 29, 2025

    0000 Skiparee Rd, Pownal, VT 05261

    • Land
    • 25.7 Acres
    • $4,475 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 22 Days On Market

    Last Listing Agent Max Squiers KW Vermont - Brenda Jones Real Estate Group

    0000 Skiparee Rd, Pownal, VT 05261
    • /40

      Not Listed For Sale

      658 Finbars Forest Rd, Manchester Center, VT 05255

      • 5 Beds
      • 4 Baths
      • 2,602 Sq Ft
      • Built 1989
      658 Finbars Forest Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Lindsey Pinder Josiah Allen Real Estate, Inc.

  • /32

    $239,900

    Open Sat 10AM - 12PM
    • 4 Beds
    • 1.5 Baths
    • 2,104 Sq Ft

    1955 Vt Route 100, Readsboro, VT 05350

    Open House: Saturday, August 15th from 10 am to 12 pm. Welcome to 1955 Vermont Route 100, a character-filled 1870 farmhouse offering 4 bedrooms, 2 bathrooms, and 2,104 square feet of finished living space on a half-acre country lot in Readsboro. Abutting Vermont National Forest and close to VASA and Vast Trails. Inside, warm wood details and inviting living spaces create a classic Vermont feel.

    Colt Hazell Flex Realty

    1955 Vt Route 100, Readsboro, VT 05350
  • /22

    $445,000

    Sold Sep 16, 2025

    163 Vt Route 30, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,590 Sq Ft
    • Built 1970

    Last Sold Summary

    • 1% Below List Price
    • $280/SF
    • 13 Days On Market

    Current Estimated Value $439,408

    Last Listing Agent Timothy Apps Four Seasons Sotheby's Int'l Realty

    163 Vt Route 30, Winhall, VT 05340
    • /32

      Est $1,002,992

      Not Listed For Sale

      1145 Powderhorn Rd, Manchester Center, VT 05255

      • 4 Beds
      • 3.5 Baths
      • 3,728 Sq Ft
      • Built 1983
      1145 Powderhorn Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 109 Days On Market

      Last Listing Agent Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  • /6

    $145,000

    Under Contract
    • Land
    • 3 Acres
    • $48,333 per Acre

    530 Finbars Forest Rd, Manchester Center, VT 05255

    This building lot borders the Manchester Country Club and, with tree clearing, would offer amazing views of the golf course and the Manchester mountains. The location provides easy access to town and everything the area has to offer. This private wooded lot is just minutes away from local highlights, including golf, skiing, hiking, and shopping. Septic permit and design available.

    Tatsiana Clark Four Seasons Sotheby's Int'l Realty

    530 Finbars Forest Rd, Manchester Center, VT 05255
  • /4

    $35,000

    Sold Jan 20, 2026

    0 Oberhugel Rd Unit 5059139, Stamford, VT 05352

    • Land
    • 2 Acres
    • $17,500 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 106 Days On Market

    Last Listing Agent Duncan Honig Maple Leaf Real Estate

    0 Oberhugel Rd Unit 5059139, Stamford, VT 05352
    • /31

      Est $502,187

      Not Listed For Sale

      109 Hillcrest Rd, Manchester Center, VT 05255

      • 2 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1969
      109 Hillcrest Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 10 Days On Market

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

  • /16

    $395,000

    Pending
    • 4,646 Sq Ft

    307 North St, Bennington, VT 05201

    Exceptional mixed-use opportunity in Bennington’s MU-2 District offering flexibility for investors, owner-occupants, or live/work configurations. Sale includes both 307 North Street and 307.5 North Street, two separate buildings situated on one 0.70-acre parcel with strong visibility and approximately 150 feet of frontage along North Street (VT Route 7). The front building (c. 1840) offers

    Jeffrey Dorman

    307 North St, Bennington, VT 05201
  • /60

    $1,300,000

    Sold Dec 10, 2025

    694 Sykes Hollow Rd, Rupert, VT 05776

    • 3 Beds
    • 2.5 Baths
    • 2,259 Sq Ft
    • Built 1789

    Last Sold Summary

    • 2% Above List Price
    • $575/SF
    • 15 Days On Market

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    694 Sykes Hollow Rd, Rupert, VT 05776
    • /35

      Est $676,100

      Not Listed For Sale

      602 Barnumville Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 1,907 Sq Ft
      • Built 1960
      602 Barnumville Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Katherine Zilkha Four Seasons Sotheby's Int'l Realty

  • /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
  • /15

    $640,000

    Sold Feb 26, 2026

    105 Elm St, Manchester, VT 05255

    • 5 Beds
    • 4 Baths
    • 3,732 Sq Ft
    • Built 1850

    Last Sold Summary

    • $171/SF
    • 2 Days On Market

    Last Listing Agent David Citron RE/MAX Four Seasons

    105 Elm St, Manchester, VT 05255
    • /31

      Est $540,158

      Not Listed For Sale

      373 Highland Ave, Manchester Center, VT 05255

      • 4 Beds
      • 1.5 Baths
      • 1,830 Sq Ft
      • Built 1905
      373 Highland Ave, Manchester Center, VT 05255

      Last Sold Summary

      • 5 Days On Market

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

  • /9

    $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. Conceptual rendering showing the potential view is based on the current

    Cheyanne Pugliese

    0 Wall St, Winhall, VT 05340
  • /55

    $800,000

    Sold Nov 17, 2025

    879 River Rd, Manchester, VT 05255

    • 3 Beds
    • 3.5 Baths
    • 2,340 Sq Ft
    • Built 1900

    Last Sold Summary

    • 6% Below List Price
    • $342/SF
    • 34 Days On Market

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

    879 River Rd, Manchester, VT 05255
    • /34

      Est $745,855

      Not Listed For Sale

      196 Ways Ln, Manchester Center, VT 05255

      • 4 Beds
      • 3 Baths
      • 2,304 Sq Ft
      • Built 1929
      196 Ways Ln, Manchester Center, VT 05255

      Last Sold Summary

      • 7 Days On Market

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

  • /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
  • /33

    $685,000

    Sold Apr 16, 2026

    158 Upland Downs Rd, Manchester Center, VT 05255

    • 3 Beds
    • 2 Baths
    • 1,743 Sq Ft
    • Built 1983

    Last Sold Summary

    • 16% Below List Price
    • $393/SF
    • 147 Days On Market

    Current Estimated Value $710,222

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

    158 Upland Downs Rd, Manchester Center, VT 05255
    • /17

      Est $330,152

      Not Listed For Sale

      1581 E Manchester Rd, Manchester Center, VT 05255

      • 2 Beds
      • 1 Bath
      • 952 Sq Ft
      • Built 1952
      1581 E Manchester Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Patti Trudel RE/MAX Four Seasons

  • /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
  • /14

    $20,000

    Sold Oct 30, 2025

    79 Skytop Dr Unit 6, Bennington, VT 05201

    • 1 Bed
    • 1 Bath
    • 561 Sq Ft
    • Built 1950

    Last Sold Summary

    • 27% Below List Price
    • $36/SF
    • 0 Days On Market

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    79 Skytop Dr Unit 6, Bennington, VT 05201
    • /28

      Est $269,237

      Not Listed For Sale

      433 Squires Rd, Manchester Center, VT 05255

      • 2 Beds
      • 1 Bath
      • 1,142 Sq Ft
      • Built 1974
      433 Squires Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Linda Benoit Highland Realty

  • /38

    $309,900

    $15K PRICE DROP Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,900 Sq Ft

    2 Pine Rd, Bennington, VT 05201

    Bright 3 bedroom, 1 and a half bath home in Bennington. Close to the hospital and offering kitchen, formal dining room, living room, and 2 main level bedrooms. Upstairs a loft office area and another bedroom. The basement is partially finished with laundry, family room and half bath. Outside there is a great deck with a separate, heated sun room and 2 car detached garage. A must see home in a

    Brenda Jones KW Vermont - Brenda Jones Real Estate Group

    2 Pine Rd, Bennington, VT 05201

Showing Results 561 - 600, Page 15 of 18

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