21,299

Bennington County, VT Homes

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  • /5

    $55,000

    • Land
    • 20,908 Sq Ft
    • $114,583 per Acre

    29 Asa Way, Bennington, VT 05257

    Build your dream home at 29 Asa's Way, ideally situated at the top of the hill in a desirable North Bennington neighborhood. This 0.48 acre lot offers a level, build friendly setting with beautiful mountain views, providing the perfect backdrop for your future home.Public water and sewer are available, along with underground utilities, making for a smooth and efficient building process.

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    (802) 215-5280

    29 Asa Way, Bennington, VT 05257
  • /24

    $3,200 Per Month

    • 4 Beds
    • 2 Baths
    • 1,950 Sq Ft
    • House for Rent

    78 Franklin Rd, Manchester, VT 05255

    WINTER RENTAL 11/15/26 to 4/15/27'Tis the season, well, almost. Winter is just around the corner, and this classic, 1920s Vermont home awaits your stay. This traditional Manchester Village home is fully furnished and ready for your Winter Season rental.Turn off your electronics, curl up with a good book, spread out a board game, and just enjoy each other's company. Located on a quiet

    Agent Photo

    Kristin Comeau

    TPW Real Estate

    (802) 327-7879

    78 Franklin Rd, 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 $144,607

    Last Listing Agent Lindsey Martin Maple Leaf Real Estate

    235 Maple St, Bennington, VT 05201
    • /44

      Est $243,480

      Not Listed For Sale

      16 Browning Place, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 1,366 Sq Ft
      • Built 1900
      16 Browning Place, Bennington, VT 05201

      Last Sold Summary

      • 45 Days On Market

  • /56

    $995,000

    • 5 Beds
    • 5 Baths
    • 4,126 Sq Ft

    238 Seminary Ave, Manchester, VT 05254

    Manchester Village LivingExperience the charm of village life in this expansive Victorian home and guest cottage, ideally located in the heart of Manchester Village. Rich in character and architectural detail, the home features original woodwork, soaring ceilings, generously sized rooms, and timeless New England appeal—enhanced by a new roof, windows and heating system.The spacious main

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    (802) 891-4018

    238 Seminary Ave, Manchester, VT 05254
  • /15

    $2,000

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • House for Rent

    208 Grove St, Bennington, VT 05201

    Charming Single-Family Home for RentWelcome home to this well-maintained single-family residence offering comfort, space, and convenience. This home features inviting living areas, a back deck, and a fenced in back yard perfect for relaxing or entertaining.Included in Rent:• Water• Sewer• Trash service• Lawn carePets:Dogs and cats will be considered

    208 Grove St, Bennington, VT 05201
  • /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 $437,791

    Last Listing Agent Angela Bevin Maple Leaf Real Estate

    356 Elm St, Bennington, VT 05201
    • /18

      Not Listed For Sale

      94 Murray Hill Woods Rd Unit 61, Manchester, VT 05255

      • 3 Beds
      • 3.5 Baths
      • 2,139 Sq Ft
      • Built 1980
      94 Murray Hill Woods Rd Unit 61, Manchester, VT 05255

      Last Sold Summary

      • 92 Days On Market

  • /38

    $350,000

    $50K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,444 Sq Ft

    250 Shepherd Ln, Arlington, VT 05250

    Looking for privacy with The National Forest right in your backyard?Welcome Home to a 3 bedroom, 2 bath home that offers the perfect blend of peaceful country living and everyday convenience.Set on a private retreat like setting, this property gives you the space and flexibility to live the lifestyle you want. Dreaming of building a barn or having horses? There’s room to make it happen.

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    (802) 613-0622

    250 Shepherd Ln, Arlington, 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

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 255-8729

    3093 Route 30, Dorset, VT 05251
  • /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
    • /15

      Est $157,888

      Not Listed For Sale

      2793 Rupert Rd, Arlington, VT 05250

      • Built 0
      2793 Rupert Rd, Arlington, VT 05250

      Last Sold Summary

      • 50 Days On Market

  • /56

    $755,000

    $25K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,423 Sq Ft

    85 Limerick Ln Unit A & B, Arlington, VT 05250

    Vermont lifestyle meets income potential! Set in the scenic Taconic and Green Mountain valley along the Battenkill River and 8 shared acres, this spacious 4-bedroom, 5-bath home, built in 2001, offers peaceful country living with versatile use.The property features three living sections with separate entrances, each with at least one 3⁄4 bath—ideal for multi-generational living, guests, or

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    (802) 266-4593

    85 Limerick Ln Unit A & B, Arlington, VT 05250
  • /20

    $4,150

    Total Monthly Price

    • 3 Beds
    • 4 Baths
    • 2,358 Sq Ft
    • House for Rent

    102 Ways Ln, Manchestr Ctr, VT 05255

    Updated Manchester Center home steps to everything in Manchester Center and Manchester Village. Surrounded by wildflower meadows and woodlands with a view of the Green Mountains from the front porch.Newly renovated bathrooms (two full, two half). Flexible layout with three bedrooms plus office/den. Kitchen with induction range and Bosch dishwasher. Adjacent dining area and screened-in

    102 Ways Ln, Manchestr Ctr, 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 $115,649

    Last Listing Agent Matt Waddington Hoffman Real Estate

    242 North Rd, East Arlington, VT 05252
    • /54

      Est $978,368

      Not Listed For Sale

      13 Windtree Rd, Bondville, VT 05340

      • 4 Beds
      • 3.5 Baths
      • 2,672 Sq Ft
      • Built 1994
      13 Windtree Rd, Bondville, VT 05340

      Last Sold Summary

      • 120 Days On Market

  • /49

    $1,450,000

    • 5 Beds
    • 4.5 Baths
    • 4,376 Sq Ft

    39 Eagle Ridge, Dorset, VT 05251

    5.7 beautiful acres just off of Morse Hill Road where the southern exposures are to behold, a warm and inviting modern designed residence, post and beam barn and sweeping mountain views await your attention! The 5 Bedroom mostly ensuite house features the grand open concept where living areas are spacious and distinctive areas yet transition beautifully from space to space with newly finished

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 416-4342

    39 Eagle Ridge, Dorset, VT 05251
  • /11

    $1,400

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 650 Sq Ft
    • Condo for Rent

    214 Beech St Unit 214 Beech St, Bennington, VT 05201

    Available June 1st. Bennington, VTAccepting applications for our lovely large downstairs apartment in a period Victorian home on a tree shaded street with much original 19 century woodwork remaining. Off street parking for one car only. Lush lawn and mature plantings. Large front porch. Hookups for washer and dryer. Every room has new paint and Scrubbed clean from stem to

    214 Beech St Unit 214 Beech St, Bennington, VT 05201
  • /31

    $895,000

    Sold Dec 12, 2025

    73 Cranberry Hill Rd, Winhall, VT 05340

    • 4 Beds
    • 4.5 Baths
    • 2,658 Sq Ft
    • Built 1984

    Last Sold Summary

    • 8% Below List Price
    • $337/SF
    • 222 Days On Market

    Current Estimated Value $921,664

    Last Listing Agent Carrie Mathews Winhall Real Estate

    73 Cranberry Hill Rd, Winhall, VT 05340
    • /29

      Est $356,302

      Not Listed For Sale

      297 Mad Tom Rd, East Dorset, VT 05253

      • 3 Beds
      • 2 Baths
      • 1,362 Sq Ft
      • Built 1920
      297 Mad Tom Rd, East Dorset, VT 05253

      Last Sold Summary

      • 46 Days On Market

  • /38

    $325,000

    • 3 Beds
    • 1.5 Baths
    • 1,829 Sq Ft

    89 Merson St, Woodford, VT 05201

    Welcome to 89 Merson Street! This charming Cape style home offers 3 bedrooms, 1 full bathroom and a half bathroom, and nearly an acre of land on a quiet in town street. Inside, you’ll find beautifully refinished hardwood floors, an updated kitchen, a spacious family room with a fireplace, and a new Weil-McLain boiler installed in February 2026.What truly sets this property apart is its

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    (802) 523-3711

    89 Merson St, Woodford, VT 05201
  • /31

    $1,275 - $1,400

    Total Monthly Price

    • 1 - 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    938 Vt-7a, Shaftsbury, VT 05262

    Lovely 1 bedroom apartment available in Shaftsbury Vermont. Rent includes water and sewer, snow plowing, and lawn maintenance. One year lease required with first and last month's rent and security deposit.

    938 Vt-7a, Shaftsbury, VT 05262
  • /60

    $530,000

    Sold Aug 15, 2025

    2354 Danby Mountain Rd, Dorset, VT 05251

    • 3 Beds
    • 2 Baths
    • 2,031 Sq Ft
    • Built 1968

    Last Sold Summary

    • 17% Below List Price
    • $261/SF
    • 244 Days On Market

    Last Listing Agent Margretta Fischer Wohler Realty Group

    2354 Danby Mountain Rd, Dorset, VT 05251
    • /37

      Not Listed For Sale

      20 Oak Hill School Rd, Pownal, VT 05261

      • 6 Beds
      • 3 Baths
      • 1,912 Sq Ft
      • Built 1963
      20 Oak Hill School Rd, Pownal, VT 05261

      Last Sold Summary

      • 69 Days On Market

  • /51

    $710,000

    $40K PRICE DROP Under Contract
    • 4 Beds
    • 3 Baths
    • 3,498 Sq Ft

    360 Mending Walls Rd, Manchester Center, VT 05255

    Mending Walls on the cul-de-sac is a beautifully maintained four bedroom residence offering privacy, peace and mountain views in a highly desirable neighborhood. Set on 1.2 acres, this home features three finished floors, a recent roof, whole-house generator, water softening system, and a backyard gardening shed for hobbyist and outdoor enthusiasts alike.The open great-room kitchen with

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 215-5395

    360 Mending Walls Rd, Manchester Center, VT 05255
  • /7

    $1,500

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,300 Sq Ft
    • Condo for Rent

    11 Route 67 W Unit 2, North Bennington, VT 05257

    Large main room is a real eye grabber! Tall ceilings and large open space. No pets, no smoking, credit and background check is required. Owners live on premise. Water/sewer, and garbage included in the rent. Heat is oil.

    11 Route 67 W Unit 2, North Bennington, VT 05257
  • /52

    $1,025,000

    Sold Jul 18, 2025

    21 Shepards Ln, Manchester, VT 05255

    • 4 Beds
    • 4 Baths
    • 3,046 Sq Ft
    • Built 1845

    Last Sold Summary

    • 14% Below List Price
    • $337/SF
    • 54 Days On Market

    Last Listing Agent Christiane Carroccio TPW Real Estate

    21 Shepards Ln, Manchester, VT 05255
    • /41

      Not Listed For Sale

      4690 Route 153, Rupert, VT 05776

      • 2 Beds
      • 2 Baths
      • 2,294 Sq Ft
      • Built 1985
      4690 Route 153, Rupert, VT 05776

      Last Sold Summary

      • 52 Days On Market

  • /38

    $449,000

    • 3 Beds
    • 2.5 Baths
    • 1,596 Sq Ft

    60 Murray Hill Heights Rd Unit 23, Manchester, VT 05255

    Murray Hill Heights – Manchester, VermontExperience the best of Southern Vermont living in this beautifully maintained end-unit condominium at Murray Hill Heights. Offering 3 bedrooms and 3 baths, this light-filled home combines comfort, privacy, and stunning views of the Taconic and Green Mountains in one of Manchester's most desirable communities. The sought-after end-unit location provides

    Agent Photo

    Kristin Comeau

    TPW Real Estate

    (802) 231-2149

    60 Murray Hill Heights Rd Unit 23, Manchester, VT 05255
  • /46

    $5,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,300 Sq Ft
    • House for Rent

    15 Nearing Rd, Winhall, VT 05340

    THE ULTIMATE STRATTON MOUNTAIN RETREAT Experience the perfect Vermont winter getaway in this exceptional home ideally located in the highly desirable Forest Farms neighborhood. Boasting a premier location with effortless mountain access, this property is designed for those who want to maximize their time on the slopes and enjoy a seamless mountain lifestyle. Available for multiple flexible

    David Powers 42 North LP

    15 Nearing Rd, Winhall, VT 05340
  • /36

    $220,000

    Sold Aug 20, 2025

    1211 Carpenter Hill Rd, Bennington, VT 05201

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1930

    Last Sold Summary

    • 10% Above List Price
    • $157/SF
    • 4 Days On Market

    Last Listing Agent Peter West BISHOP WEST REAL ESTATE

    1211 Carpenter Hill Rd, Bennington, VT 05201
    • /22

      Est $279,640

      Not Listed For Sale

      494 Atwood Dr, Pownal, VT 05261

      • 3 Beds
      • 2 Baths
      • 2,048 Sq Ft
      • Built 2006
      494 Atwood Dr, Pownal, VT 05261

      Last Sold Summary

      • 5 Days On Market

  • /39

    $219,000

    Under Contract
    • 2 Beds
    • 1 Bath
    • 988 Sq Ft

    215 Orchard St, Pownal, VT 05261

    Welcome to this adorable bungalow in the heart of Pownal the opportunity you’ve been waiting for! If you’ve been searching for a home in Pownal but haven’t been able to find the right fit or move quickly enough, this charming 2 bedroom, 1 bath home may be exactly what you’ve been looking for.Featuring an updated kitchen, a cozy pellet stove that primarily heats the home, and a bright enclosed

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    (802) 636-5434

    215 Orchard St, Pownal, VT 05261
  • /15

    $1,350 Per Month

    • Studio
    • 1 Bath
    • 370 Sq Ft
    • Putnam Winslow– $1,350 – 1 Bathroom Studio, 370 SQ.FT. – UTILITIES INCLUDED, Available 6/8/26

    339 Main St Unit 307, Bennington, VT 05201

    Welcome to Putnam Block, Winslow Studio #307– Fully renovated studio apartment available for rent in downtown Bennington– Large windows, wood floors, high ceilings– Utilities Included (electric, heat, water and AC)– Off street parking– Free, on-site laundryThis is an income qualifying affordable unit. Annual household income for single occupancy may not exceed

    339 Main St Unit 307, Bennington, VT 05201
  • /17

    $159,900

    Sold Jun 05, 2026

    432 South St Unit B2, Bennington, VT 05201

    • 2 Beds
    • 1.5 Baths
    • 852 Sq Ft
    • Built 1989

    Last Sold Summary

    • $188/SF
    • 40 Days On Market

    Current Estimated Value $168,882

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

    432 South St Unit B2, Bennington, VT 05201
    • /60

      Est $396,546

      Not Listed For Sale

      145 Main St, Pownal, VT 05261

      • 4 Beds
      • 2.5 Baths
      • 2,032 Sq Ft
      • Built 1742
      145 Main St, Pownal, VT 05261

      Last Sold Summary

      • 11 Days On Market

  • /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

    (802) 551-3900

    8 West St, Bennington, VT 05201
  • /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
  • /36

    $435,000

    Sold Mar 24, 2026

    1061 Granger Hollow Rd, North Bennington, VT 05257

    • 3 Beds
    • 2 Baths
    • 2,108 Sq Ft
    • Built 1990

    Last Sold Summary

    • 13% Below List Price
    • $206/SF
    • 215 Days On Market

    Current Estimated Value $442,090

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    1061 Granger Hollow Rd, North Bennington, VT 05257
    • /43

      Est $1,521,210

      Not Listed For Sale

      164 Landmark Ln, Manchester Center, VT 05255

      • 4 Beds
      • 3.5 Baths
      • 3,990 Sq Ft
      • Built 1810
      164 Landmark Ln, Manchester Center, VT 05255

      Last Sold Summary

      • 397 Days On Market

Showing Results 81 - 120, Page 3 of 18

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