20,622

Bennington County, VT Homes

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  • /33

    $279,000

    $20K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,408 Sq Ft

    8 West St, Bennington, VT 05201

    Nestled in the heart of the charming North Bennington community, this lovingly maintained 3 bedroom, 1.5 bath home is ready for its next chapter. Recently refreshed with newly painted interiors, rejuvenated floors, updated electrical, a recently repointed foundation, and repointed chimney, this home blends classic character with thoughtful updates throughout.Enjoy the convenience of first

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    8 West St, Bennington, VT 05201
  • /6

    $1,025 Per Month

    • 1 Bed
    • 1 Bath
    • 441 Sq Ft
    • 111/113 Gage St

    111-113-113 Gage St Unit 111 #2, Bennington, VT 05201

    *MANAGED BY CRM, LLC*NO FEES CHARGED AT APPLICATION PROCESS, PLEASE BE AWARE OF SCAMS!Charming one-bedroom unit nestled in the heart of our beautiful town. Modern and cozy. Conveniently located for easy access to local amenities, including unique local shops and a relaxed, small-town atmosphere. Your ideal home for enjoying the simplicity of small-town living.For additional

    111-113-113 Gage St Unit 111 #2, Bennington, VT 05201
  • /32

    $410,000

    Sold Apr 29, 2026

    8 Silver Birch Rd Unit 8, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,215 Sq Ft
    • Built 1968

    Last Sold Summary

    • 5% Below List Price
    • $337/SF
    • 101 Days On Market

    Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

    8 Silver Birch Rd Unit 8, Winhall, VT 05340
    • /40

      Est $899,742

      Not Listed For Sale

      67 Coventry Ln, Manchester Center, VT 05255

      • 3 Beds
      • 3 Baths
      • 2,774 Sq Ft
      • Built 1965
      67 Coventry Ln, Manchester Center, VT 05255

      Last Sold Summary

      • 10 Days On Market

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

  • /35

    $525,000

    • 3 Beds
    • 2.5 Baths
    • 1,580 Sq Ft

    134 Fox Hill Rd Unit PVT, Shaftsbury, VT 05262

    Welcome to the Fox Hill Community and a beautiful modern home tucked away on a private road in Shaftsbury, Vermont offering the perfect blend of privacy, comfort, and stunning Vermont scenery. The home offers 3 bedrooms and 3 bathrooms along with gorgeous mountain views. There is a cozy fireplace in the living room with ample space provided for a family, friends and entertaining. The landscaping

    Agent Photo

    Monique Geannelis

    Mahar McCarthy Real Estate

    134 Fox Hill Rd Unit PVT, Shaftsbury, VT 05262
  • /57

    $4,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,906 Sq Ft
    • Townhouse for Rent

    55 Murray Hill Woods Unit 49, Manchester, VT 05255

    This lovely 3-bedroom plus loft, 2.5-bath condominium comfortably sleeps up to 8 people and is conveniently located in Manchester, within walking distance of shops, restaurants, and local amenities. The home features a fully renovated kitchen with stainless steel appliances, a 4-seat breakfast bar, and beautiful wood floors throughout the main living area. The inviting living room offers a cozy

    Laura Beckwith Josiah Allen Real Estate, Inc.

    55 Murray Hill Woods Unit 49, Manchester, VT 05255
  • /57

    $190,000

    Sold Sep 16, 2025

    100 Webb St, Bennington, VT 05201

    • 3 Beds
    • 1 Bath
    • 1,416 Sq Ft
    • Built 1943

    Last Sold Summary

    • 12% Below List Price
    • $134/SF
    • 75 Days On Market

    Current Estimated Value $200,839

    Last Listing Agent Lindsey Martin Maple Leaf Real Estate

    100 Webb St, Bennington, VT 05201
    • /37

      Not Listed For Sale

      63 Sykes Hollow Rd, Dorset, VT 05251

      • 3 Beds
      • 3.5 Baths
      • 3,060 Sq Ft
      • Built 2017
      63 Sykes Hollow Rd, Dorset, VT 05251

      Last Sold Summary

      • 4 Days On Market

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

  • /51

    $475,000

    • 3 Beds
    • 2 Baths
    • 2,721 Sq Ft

    181 White Tail Run, Arlington, VT 05250

    Tucked into the foothill of the green mountains you will find this well constructed 3 bedroom 2 bath cape style home with oversized 2 car garage on 2.19 acres. This comfortable home features an updated kitchen with new island, updated appliances 6 burner gas range and classic tile back splash. The living room offers a beautiful soap stone wood burning stove and a new mini split for AC and heat.

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    181 White Tail Run, Arlington, VT 05250
  • /11

    $1,700 Per Month

    • 3 Beds
    • 1 Bath
    • 1,130 Sq Ft
    • Condo for Rent

    207 Maple St Unit 1, Bennington, VT 05201

    *MANAGED BY CRM, LLC*NO FEES CHARGED AT APPLICATION PROCESS, PLEASE BE AWARE OF SCAMS!Spacious 3 bedroom unit located in downtown Bennington. A spacious apartment with front and back entrance. Walking distance to stores, restaurants, and many more! Experience the charm of Bennington and all it has to offer from the comfort of your new home. Don't miss out on this opportunity to live

    207 Maple St Unit 1, Bennington, VT 05201
  • /36

    $300,000

    Sold Apr 02, 2026

    318 Chester Knoll Dr, Bennington, VT 05201

    • 3 Beds
    • 2 Baths
    • 1,865 Sq Ft
    • Built 2006

    Last Sold Summary

    • $161/SF
    • 5 Days On Market

    Current Estimated Value $312,085

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    318 Chester Knoll Dr, Bennington, VT 05201
    • /34

      Est $519,896

      Not Listed For Sale

      32 County Rd, Stamford, VT 05352

      • 2 Beds
      • 2 Baths
      • 1,586 Sq Ft
      • Built 1989
      32 County Rd, Stamford, VT 05352

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Rebecca Seymour Brattleboro Area Realty

  • /48

    $685,000

    $95K PRICE DROP
    • 3,423 Sq Ft

    85 Limerick Ln, Arlington, VT 05250

    Seller is offering a credit to buyers of $5000 towards closing costs at closing. • Battenkill River Frontage – Enjoy direct access to the Battenkill River, 8 shared acres, and a prime location just minutes from Manchester’s shopping, dining, skiing, biking, and hiking. • Spacious & Flexible – Light-filled 4-bedroom, 5-bath home with quality finishes, a private apartment, multiple porches, a

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    85 Limerick Ln, Arlington, VT 05250
  • /13

    $14,000 Per Month

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    41 Cranberry Hill Rd, Winhall, VT 05340

    Le Petite Chalet! -A rare opportunity to rent a beautifully updated 1-bedroom chalet in Strattonwald available this ski season. The house has been fully renovated with many modern updates made to this classic chalet home. There is a delightful open concept kitchen, living and dining on the first floor and a luxurious bedroom, bath and relaxing nook on the lower level. Skip the parking hassle at

    Peggy O'neill Cummings & Co

    41 Cranberry Hill Rd, Winhall, VT 05340
  • /26

    $440,000

    Sold Jun 29, 2026

    36 Birch Hill Rd Unit 8 Red Maple, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,215 Sq Ft
    • Built 1968

    Last Sold Summary

    • 2% Below List Price
    • $362/SF
    • 10 Days On Market

    Last Listing Agent Helen Nault

    36 Birch Hill Rd Unit 8 Red Maple, Winhall, VT 05340
    • /22

      Not Listed For Sale

      16 Clark Rd, Rupert, VT 05776

      • 4 Beds
      • 4 Baths
      • 2,708 Sq Ft
      • Built 1989
      16 Clark Rd, Rupert, VT 05776

      Last Sold Summary

      • 19 Days On Market

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

  • /60

    $799,000

    $76K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,462 Sq Ft

    636 Dexter Rd, Shaftsbury, VT 05262

    The Dexter Road Farmhouse, Circa 1800 In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic nearby backroads to write “Stopping by the Woods on a Snowy Evening." Dating back more than 225 years, this charming farmhouse offers a rare opportunity to own a piece of Vermont history while embracing the slower pace and natural beauty that define the region. Tucked away

    Agent Photo

    Kristin Comeau

    TPW Real Estate

    636 Dexter Rd, Shaftsbury, VT 05262
  • /6

    $1,400 Per Month

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • 133/135 Dewey St

    133-135 Dewey St Unit 133 #1, Woodford, VT 05201

    *MANAGED BY CRM, LLC*NO FEES CHARGED AT APPLICATION PROCESS, PLEASE BE AWARE OF SCAMS!Charming two-bedroom unit nestled in the heart of our cozy town. Modern and spacious. Conveniently located for easy access to local amenities, including unique local shops and a relaxed, small-town atmosphere. Your ideal home for enjoying the simplicity of small-town living.For additional

    133-135 Dewey St Unit 133 #1, Woodford, VT 05201
  • /46

    $290,000

    Sold Apr 10, 2026

    112 Norton St, Bennington, VT 05201

    • 2 Beds
    • 1.5 Baths
    • 1,564 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Below List Price
    • $185/SF
    • 8 Days On Market

    Current Estimated Value $298,265

    Last Listing Agent Vicki Wilson Maple Leaf Real Estate

    112 Norton St, Bennington, VT 05201
    • /36

      Est $837,288

      Not Listed For Sale

      469 Laclair Rd, Shaftsbury, VT 05262

      • 3 Beds
      • 3.5 Baths
      • 3,104 Sq Ft
      • Built 2011
      469 Laclair Rd, Shaftsbury, VT 05262

      Last Sold Summary

      • 3 Days On Market

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

  • /55

    $495,000

    $60K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,344 Sq Ft

    935 Old Manchester Rd, Peru, VT 05152

    Cozy Off-Grid Cabin on 10 Private Acres – Peace, Privacy & Ski AccessEscape to your own woodland retreat with this charming 2-bed, 1-bath cabin nestled on 10 serene acres of open meadow and forest. Just 4.5 miles to Bromley Ski & Snowboarding Mountain, this property offers the perfect mix of off-grid living and outdoor adventure.Fully self-sufficient with solar power and propane generator

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    935 Old Manchester Rd, Peru, VT 05152
  • /40

    $4,250 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,372 Sq Ft
    • Townhouse for Rent

    9 Murray Hill Rd S Unit 9, Manchester, VT 05255

    NOW AVAILABLE – Vermont Two-Month Winter Rental? December 2026 – February 2027Welcome to Pine Haven! Enjoy a winter getaway in this beautifully furnished three-bedroom Murray Hill end-unit townhouse, ideally located in the heart of Manchester, Vermont. With Bromley Mountain and Stratton Mountain Resort just a short drive away, plus shopping, dining, and local attractions nearby, it's the

    Elliott Nachwalter TPW Real Estate

    9 Murray Hill Rd S Unit 9, Manchester, VT 05255
  • /41

    $141,000

    Sold Apr 01, 2026

    235 Maple St, Bennington, VT 05201

    • 2 Beds
    • 1.5 Baths
    • 1,060 Sq Ft
    • Built 1915

    Last Sold Summary

    • 5% Below List Price
    • $133/SF
    • 13 Days On Market

    Current Estimated Value $150,582

    Last Listing Agent Lindsey Martin Maple Leaf Real Estate

    235 Maple St, Bennington, VT 05201
    • /40

      Est $253,333

      Not Listed For Sale

      112 County Rd, Stamford, VT 05352

      • 2 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1972
      112 County Rd, Stamford, VT 05352

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Jacki Murano Southern Vermont Realty Group

  • /52

    $359,000

    • 2 Beds
    • 1 Bath
    • 1,686 Sq Ft

    712 Vt Route 30, Dorset, VT 05251

    Nestled in a picturesque Dorset, Vermont setting, this classic 1850 farmhouse offers an affordable opportunity to create the home of your dreams. Situated on a manageable quarter-acre lot, the property features a detached two-car garage, two additional outbuildings, screened in porch, enclosed three season porch and established perennial plantings with classic New England character throughout.

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    712 Vt Route 30, Dorset, VT 05251
  • /42

    $4,000 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,326 Sq Ft
    • House for Rent

    259 Nottingham Park, Manchester Center, VT 05255

    Charming WINTER SEASONAL RENTAL in the heart of Southern Vermont! This adorable Cape offers 2 bedrooms and 1.5 baths with warm wood floors throughout. Enjoy cozy evenings in the inviting living room by the woodstove or relax in the separate den after a day on the slopes. The home also features convenient ground level laundry, a spacious deck, and beautiful mountain views. Ideally located just

    Laura Beckwith Josiah Allen Real Estate, Inc.

    259 Nottingham Park, Manchester Center, VT 05255
  • /34

    $450,000

    Sold Feb 13, 2026

    356 Elm St, Bennington, VT 05201

    • 3 Beds
    • 2.5 Baths
    • 2,273 Sq Ft
    • Built 1934

    Last Sold Summary

    • $198/SF
    • 0 Days On Market

    Current Estimated Value $447,099

    Last Listing Agent Angela Bevin Maple Leaf Real Estate

    356 Elm St, Bennington, VT 05201
    • /31

      Not Listed For Sale

      6 Black Birch Rd, Winhall, VT 05340

      • 3 Beds
      • 2 Baths
      • 1,215 Sq Ft
      • Built 1968
      6 Black Birch Rd, Winhall, VT 05340

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

  • /58

    $1,650,000

    $225K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 3,368 Sq Ft

    276 Wilcox Hollow Rd, Sandgate, VT 05250

    Luxury Timber Frame Estate on 52+ Acres in Southern Vermont. This exceptional custom post-and-beam retreat is privately set amid rolling hardwood forestland, offering expansive mountain views, remarkable privacy, and a rare sense of peace and connection to nature. Designed for both elegance and efficiency, the home features solar panels with two Tesla Powerwalls for optional off-grid

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    276 Wilcox Hollow Rd, Sandgate, VT 05250
  • /37

    $7,500 Per Month

    • 3 Beds
    • 3 Baths
    • 1,980 Sq Ft
    • House for Rent

    3093 Route 30, Dorset, VT 05251

    Wonderful Dorset Village Historic Colonial, private and completely protected by the established vintage tree line that buffers the neighbors and Route 30. Walk to Village location, this property has been fully renovated with updated kitchen and baths. The house is warm and welcoming with front and side covered porch entrance while the rear screened porch creates an expansive summer room to the

    Laura Beckwith Josiah Allen Real Estate, Inc.

    3093 Route 30, Dorset, VT 05251
  • /58

    $1,495,000

    Sold Jul 30, 2026

    16 West Rd, Bennington, VT 05201

    • 7 Beds
    • 5.5 Baths
    • 6,392 Sq Ft
    • Built 1910

    Last Sold Summary

    • $234/SF
    • 65 Days On Market

    Current Estimated Value $1,451,308

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    16 West Rd, Bennington, VT 05201
    • /40

      Est $520,640

      Not Listed For Sale

      68 Willows Way Unit 4, Peru, VT 05152

      • 3 Beds
      • 3.5 Baths
      • 1,010 Sq Ft
      • Built 1984
      68 Willows Way Unit 4, Peru, VT 05152

      Last Sold Summary

      • 116 Days On Market

      Last Listing Agent Dylan Gage Bromley Real Estate

  • /41

    $550,000

    Under Contract
    • 5 Beds
    • 2 Baths
    • 1,974 Sq Ft

    971 S Stream Rd, Bennington, VT 05201

    Have you been searching for the Vermont farmhouse that truly feels like home? The one with the land, the barns, the mountain views, the wraparound driveway, the screened in porch, and the beautiful front porch where you can sit and enjoy quiet mornings and peaceful evenings? This is that home.Situated on over 17 acres, this property offers not one but two barns, established fenced pastures,

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    971 S Stream Rd, Bennington, VT 05201
  • /60

    $5,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,210 Sq Ft
    • House for Rent

    80 Eagle Nest Rd, Manchester, VT 05255

    Spend your summer in this charming 3 bedroom, 2.5 bath free standing condo located in the heart of Manchester Center. This spacious three level home offers comfort, convenience, and easy access to everything the area has to offer. The main floor features a bright living room, a fully equipped kitchen, a dining area, and a convenient half bath perfect for relaxing or entertaining. Upstairs, you’ll

    Laura Beckwith Josiah Allen Real Estate, Inc.

    80 Eagle Nest Rd, Manchester, VT 05255
  • /56

    $885,000

    Sold Jun 15, 2026

    227 Kestrel Ct Unit 12, Manchester, VT 05254

    • 4 Beds
    • 4 Baths
    • 2,924 Sq Ft
    • Built 1986

    Last Sold Summary

    • 5% Above List Price
    • $303/SF
    • 2 Days On Market

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

    227 Kestrel Ct Unit 12, Manchester, VT 05254
    • /40

      Est $324,578

      Not Listed For Sale

      214 Pleasant St, Arlington, VT 05250

      • 4 Beds
      • 2 Baths
      • 1,890 Sq Ft
      • Built 1890
      214 Pleasant St, Arlington, VT 05250

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Lilli West Maple Leaf Real Estate

  • /17

    $198,900

    • 2 Beds
    • 1 Bath
    • 1,332 Sq Ft

    348 Center St, Pownal, VT 05261

    Tucked into the rolling countryside of Pownal, this one-of-a-kind property offers something increasingly hard to find: space, story, and the freedom to make it your own. Set on 4.15 private acres, Once home to a beloved local dairy bar a second cabin and additional outbuildings, all awaiting the right buyer's vision and craftsmanship. Whether you're dreaming of a restored country residence, a

    Agent Photo

    Sheryl Morehouse

    Bishop West Real Estate, Inc.

    348 Center St, Pownal, VT 05261
  • /22

    $25,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,111 Sq Ft
    • Townhouse for Rent

    32 Eagle Nest Rd, Manchester Center, VT 05255

    Enjoy your Vermont ski season 26-27 in this sun-filled, immaculate, centrally-located Manchester townhouse! Eagle Nest is on the "ski" side of town, and also just up the hill from the celebrated Italian market Al Ducci's for après ski convenience. This space has three floors, with two living rooms and plenty of room for everyone. Interiors are modern, immaculate and well-curated. Perched just off

    Jamie Luke TPW Real Estate

    32 Eagle Nest Rd, Manchester Center, VT 05255
  • /12

    $100,000

    Sold Sep 08, 2025

    242 North Rd, East Arlington, VT 05252

    • 2 Beds
    • 1.5 Baths
    • 1,056 Sq Ft
    • Built 1930

    Last Sold Summary

    • 26% Below List Price
    • $95/SF
    • 32 Days On Market

    Current Estimated Value $140,334

    Last Listing Agent Matt Waddington Hoffman Real Estate

    242 North Rd, East Arlington, VT 05252
    • /9

      Not Listed For Sale

      78 Heartwellville View Rd, Readsboro, VT 05350

      78 Heartwellville View Rd, Readsboro, VT 05350

      Last Sold Summary

      • 167 Days On Market

      Last Listing Agent Jennifer Hovey-Densmore Deerfield Valley Real Estate

Showing Results 81 - 120, Page 3 of 18

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