20,610

Bennington County, VT Homes

Section Image
    • /28

      Est $817,521

      Not Listed For Sale

      182 Mending Walls Rd, Manchester Center, VT 05255

      • 4 Beds
      • 4 Baths
      • 1,955 Sq Ft
      • Built 2002
      182 Mending Walls Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Carrie Mathews Winhall Real Estate

  • /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 17acre 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 throw

    Michelle O'Neil Deerfield Valley Real Estate

    00 Bill T Dr, Readsboro, VT 05350
  • /58

    $975,000

    Sold Nov 27, 2025

    20 Jamie Ln, Winhall, VT 05340

    • 5 Beds
    • 3.5 Baths
    • 3,500 Sq Ft
    • Built 1987

    Last Sold Summary

    • $279/SF
    • 38 Days On Market

    Current Estimated Value $968,812

    Last Listing Agent David Powers 42 North LP

    20 Jamie Ln, Winhall, VT 05340
    • /24

      Est $686,283

      Not Listed For Sale

      94 E Manchester Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 1,649 Sq Ft
      • Built 2002
      94 E Manchester Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 113 Days On Market

      Last Listing Agent Annette Gallo Real Broker LLC

  • /38

    $335,000

    Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,414 Sq Ft

    308 Crescent Blvd, Bennington, VT 05201

    Welcome home to this meticulously maintained 3 bedroom, 1.5 bath ranch, perfectly nestled in a highly desirable neighborhood. Offering over 1,400 square feet of single level living space, this home combines classic charm, everyday comfort, and an unbeatable location. Rich hardwood floors flow throughout most of the home creating a warm and inviting atmosphere from the moment you step inside. The

    Angela Bevin Maple Leaf Real Estate

    308 Crescent Blvd, Bennington, VT 05201
  • /44

    $365,000

    Sold Feb 19, 2026

    2842 Vt Route 7a, Shaftsbury, VT 05262

    • 3 Beds
    • 2 Baths
    • 2,661 Sq Ft
    • Built 1969

    Last Sold Summary

    • 8% Below List Price
    • $137/SF
    • 79 Days On Market

    Current Estimated Value $381,363

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    2842 Vt Route 7a, Shaftsbury, VT 05262
    • /40

      Est $1,063,314

      Not Listed For Sale

      160 Hemlock Ridge Rd, Manchester Center, VT 05255

      • 3 Beds
      • 3.5 Baths
      • 4,139 Sq Ft
      • Built 2002
      160 Hemlock Ridge Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 4 Days On Market

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

  • /13

    $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
  • /30

    $717,500

    Sold Feb 13, 2026

    32 Cobble Ridge Rd Unit D10, Winhall, VT 05155

    • 3 Beds
    • 3 Baths
    • 2,317 Sq Ft
    • Built 1985

    Last Sold Summary

    • 2% Below List Price
    • $310/SF
    • 60 Days On Market

    Last Listing Agent Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

    32 Cobble Ridge Rd Unit D10, Winhall, VT 05155
    • /40

      Est $932,118

      Not Listed For Sale

      201 Hemlock Ridge Rd, Manchester Center, VT 05255

      • 4 Beds
      • 4.5 Baths
      • 2,814 Sq Ft
      • Built 1998
      201 Hemlock Ridge Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 2 Days On Market

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

  • /4

    $350,000

    New Construction Pending
    • 2 Beds
    • 2 Baths
    • 1,190 Sq Ft

    526 Jennings Brook Dr, Bennington, VT 05201

    Brand new 2026 construction offering the ease of single-level living with thoughtful, ADA-compliant design throughout. This energy-efficient home features 2 bedrooms and 2 full bathrooms, including a well-designed primary suite, plus convenient in-unit laundry. The open-concept layout is highlighted by a spacious kitchen and a cathedral ceiling that brings in abundant natural light and an airy

    Lilli West Maple Leaf Real Estate

    526 Jennings Brook Dr, Bennington, VT 05201
  • /58

    $590,000

    Sold Feb 27, 2026

    1098 W Sandgate Rd, Arlington, VT 05250

    • 3 Beds
    • 2.5 Baths
    • 3,284 Sq Ft
    • Built 1988

    Last Sold Summary

    • 6% Below List Price
    • $180/SF
    • 35 Days On Market

    Current Estimated Value $604,363

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

    1098 W Sandgate Rd, Arlington, VT 05250
    • /40

      Est $1,647,610

      Not Listed For Sale

      430 Riverbend Dr, Manchester Center, VT 05255

      • 4 Beds
      • 4.5 Baths
      • 4,891 Sq Ft
      • Built 1997
      430 Riverbend Dr, Manchester Center, VT 05255

      Last Sold Summary

      • 278 Days On Market

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

  • /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
  • /22

    $595,000

    Sold Jan 26, 2026

    62 Owls Nest Cir Unit B8, Manchester, VT 05255

    • 3 Beds
    • 2.5 Baths
    • 1,963 Sq Ft
    • Built 1985

    Last Sold Summary

    • $303/SF
    • 11 Days On Market

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

    62 Owls Nest Cir Unit B8, Manchester, VT 05255
    • /29

      Est $1,203,116

      Not Listed For Sale

      667 Canterbury Rd, Manchester Center, VT 05255

      • 5 Beds
      • 5 Baths
      • 4,016 Sq Ft
      • Built 1990
      667 Canterbury Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 42 Days On Market

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

  • /42

    $3,900,000

    • 5 Beds
    • 7 Baths
    • 11,736 Sq Ft

    2236 River Rd, Manchester, VT 05254

    Set on more than 18 picturesque acres along desirable River Road in Manchester Village, this extraordinary, converted farm offers a rare blend of historic character, modern comfort, & endless possibilities. Thoughtfully transformed into a multi-use residential compound, the property features four distinct living, working, & entertaining spaces, each with its own personality and purpose.

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

    2236 River Rd, Manchester, VT 05254
  • /24

    $615,000

    Sold Aug 25, 2025

    129 Coventry Ln, Manchester Center, VT 05255

    • 3 Beds
    • 2.5 Baths
    • 2,426 Sq Ft
    • Built 1972

    Last Sold Summary

    • 5% Below List Price
    • $254/SF
    • 68 Days On Market

    Current Estimated Value $643,287

    Last Listing Agent Joseph Cajzer Josiah Allen Real Estate, Inc.

    129 Coventry Ln, Manchester Center, VT 05255
    • /31

      Est $623,286

      Not Listed For Sale

      350 Carlen St, Manchester Center, VT 05255

      • 3 Beds
      • 2.5 Baths
      • 2,177 Sq Ft
      • Built 1988
      350 Carlen St, Manchester Center, VT 05255

      Last Sold Summary

      • 170 Days On Market

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

  • /46

    $275,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,302 Sq Ft

    2867 Chapel Rd, Bennington, VT 05201

    Tucked into a private wooded setting on the outskirts of town, this distinctive 3-bedroom, 1.5-bath Adirondack-inspired chalet blends rustic character, flexible living space, and an exceptional connection to the outdoors. Its steep roofline, front balcony, exposed beams, and metal roof give the home memorable architectural presence, while the peaceful surroundings create a true retreat from the

    Jenifer Prouty Hoffman Hoffman Real Estate

    2867 Chapel Rd, Bennington, VT 05201
  • /31

    $1,347,000

    Sold Nov 10, 2025

    951 Rupert Rd, Arlington, VT 05250

    • 5 Beds
    • 5 Baths
    • 6,200 Sq Ft
    • Built 2006

    Last Sold Summary

    • 15% Below List Price
    • $217/SF
    • 110 Days On Market

    Current Estimated Value $1,303,013

    Last Listing Agent Kristin Pirie

    951 Rupert Rd, Arlington, VT 05250
    • /40

      Est $739,998

      Not Listed For Sale

      190 Meadow Ridge Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2.5 Baths
      • 2,564 Sq Ft
      • Built 1985
      190 Meadow Ridge Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 59 Days On Market

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

  • /52

    $850,000

    $120K 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
  • /28

    $1,425,000

    Sold Jul 31, 2026

    43 Middle Ridge Rd Unit 415, Winhall, VT 05155

    • 4 Beds
    • 3.5 Baths
    • 2,363 Sq Ft
    • Built 2003

    Last Sold Summary

    • 16% Below List Price
    • $603/SF
    • 327 Days On Market

    Last Listing Agent Edwin Kevil Stratton Real Estate

    43 Middle Ridge Rd Unit 415, Winhall, VT 05155
    • /26

      Est $795,496

      Not Listed For Sale

      373 Hillcrest Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2.5 Baths
      • 2,124 Sq Ft
      • Built 1986
      373 Hillcrest Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

  • /37

    $575,000

    $10K PRICE DROP
    • 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
  • /21

    $120,000

    Sold Jun 26, 2026

    773 Shaftsbury Hollow Rd, Shaftsbury, VT 05262

    • Land
    • 4 Acres
    • $30,000 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 38 Days On Market

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    773 Shaftsbury Hollow Rd, Shaftsbury, VT 05262
    • /32

      Est $631,519

      Not Listed For Sale

      251 Hillcrest Rd, Manchester Center, VT 05255

      • 3 Beds
      • 3.5 Baths
      • 2,084 Sq Ft
      • Built 1986
      251 Hillcrest Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 18 Days On Market

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

  • /32

    $449,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 1,460 Sq Ft

    32 Aspen Ln, Winhall, VT 05340

    A Sanctuary for Every Season:Picture the moment you turn off the main road and onto tree-lined Aspen Lane. The frantic pace of the week instantly drops away as you pull into your driveway. Tucked into a lush, wooded lot, this four-bedroom chalet is designed for those who live for the outdoors. Whether you’re here to chase the morning light on the slopes of nearby Stratton Resort or to spend a

    Robin Apps Four Seasons Sotheby's Int'l Realty

    32 Aspen Ln, Winhall, VT 05340
  • /36

    $850,000

    Sold Dec 04, 2025

    109 Nichols Hill Ln, Dorset, VT 05251

    • 3 Beds
    • 2.5 Baths
    • 1,946 Sq Ft
    • Built 1978

    Last Sold Summary

    • 11% Below List Price
    • $437/SF
    • 30 Days On Market

    Current Estimated Value $864,484

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

    109 Nichols Hill Ln, Dorset, VT 05251
    • /32

      Est $680,359

      Not Listed For Sale

      409 Bromley Brook Rd, Manchester Center, VT 05255

      • 4 Beds
      • 2 Baths
      • 2,700 Sq Ft
      • Built 1986
      409 Bromley Brook Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Brian Hill Remax Summit

  • /26

    $2,300,000

    • 5 Beds
    • 3.5 Baths
    • 3,332 Sq Ft

    241 High Hill Rd, Manchester Center, VT 05255

    Perched on a hillside in one of the area's most sought-after in-town locations, this special property offers a rare combination of privacy, breathtaking mountain views, and a picturesque pond, all just moments from local shops, restaurants, and amenities. Surrounded by established landscaping and filled with natural light, the home captures the beauty of its setting through expansive windows on

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

    241 High Hill Rd, Manchester Center, VT 05255
  • /40

    $1,000,000

    Sold Feb 24, 2026

    19 Roundtree Rd, Bondville, VT 05340

    • 4 Beds
    • 2.5 Baths
    • 3,086 Sq Ft
    • Built 1978

    Last Sold Summary

    • 2% Below List Price
    • $324/SF
    • 80 Days On Market

    Current Estimated Value $1,000,022

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    19 Roundtree Rd, Bondville, VT 05340
    • /26

      Est $607,929

      Not Listed For Sale

      84 Green Mountain Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2.5 Baths
      • 2,182 Sq Ft
      • Built 1992
      84 Green Mountain Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 15 Days On Market

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

  • /19

    $182,000

    $13K PRICE DROP Under Contract
    • 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
  • /44

    $702,000

    Sold Oct 24, 2025

    86 Benson Fuller Dr, Bondville, VT 05340

    • 4 Beds
    • 2 Baths
    • 2,040 Sq Ft
    • Built 1983

    Last Sold Summary

    • 6% Below List Price
    • $344/SF
    • 42 Days On Market

    Current Estimated Value $687,284

    Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    86 Benson Fuller Dr, Bondville, VT 05340
    • /20

      Est $418,255

      Not Listed For Sale

      200 Carlen St, Manchester Center, VT 05255

      • 2 Beds
      • 2 Baths
      • 1,693 Sq Ft
      • Built 1985
      200 Carlen St, Manchester Center, VT 05255

      Last Sold Summary

      • 64 Days On Market

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

  • /41

    $939,000

    • 5 Beds
    • 6 Baths
    • 3,031 Sq Ft

    3191 Vermont 30, Dorset, VT 05251

    Dorset Village Investor's choice! Village Commercial... Currently Presenting a 5 unit, 3030 SF residence that can not be reproduced locally. This building has been lifted and a full (includes a small crawl) poured concrete foundation installed... dry as can be... clean as any basement can be hoped for! There are a mix of one bedrooms and studios... The configuration can be easily altered to

    Laura Beckwith Josiah Allen Real Estate, Inc.

    3191 Vermont 30, Dorset, VT 05251
  • /20

    $500,000

    Sold Nov 26, 2025

    374 Winhall Hollow Rd, Winhall, VT 05340

    • 4 Beds
    • 3 Baths
    • 1,920 Sq Ft
    • Built 1986

    Last Sold Summary

    • 1% Above List Price
    • $260/SF
    • 3 Days On Market

    Current Estimated Value $512,892

    Last Listing Agent Annette Gallo Real Broker LLC

    374 Winhall Hollow Rd, Winhall, VT 05340
    • /35

      Est $839,871

      Not Listed For Sale

      2529 Main St, Manchester Center, VT 05255

      • 4 Beds
      • 2 Baths
      • 2,520 Sq Ft
      • Built 1780
      2529 Main St, Manchester Center, VT 05255

      Last Sold Summary

      • 9 Days On Market

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

Showing Results 521 - 560, Page 14 of 18

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