5,202

Bennington, VT Homes

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  • /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
  • /6

    $950 Per Month

    • 1 Bed
    • 1 Bath
    • 450 Sq Ft
    • Condo for Rent

    103 County St Unit 2, Bennington, VT 05201

    Property Id: 810906 1 bedroom apartment is located on second floor.Month to month lease where tenants pay for their utilities such as heat electric etc..

    103 County St Unit 2, Bennington, VT 05201
  • /11

    $162,500

    Sold Sep 04, 2026

    905 County St, Bennington, VT 05201

    • 4 Beds
    • 2 Baths
    • 2,643 Sq Ft
    • Built 1920

    Last Sold Summary

    • 5% Above List Price
    • $61/SF
    • 14 Days On Market

    Current Estimated Value $163,622

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

    905 County St, Bennington, VT 05201
    • /47

      Est $286,817

      Not Listed For Sale

      120 Imperial Ave, Bennington, VT 05201

      • 4 Beds
      • 2.5 Baths
      • 2,404 Sq Ft
      • Built 1895
      120 Imperial Ave, Bennington, VT 05201

      Last Sold Summary

      • 114 Days On Market

      Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  • /33

    $349,000

    $26K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,911 Sq Ft

    21 Russett Dr, Bennington, VT 05201

    Tucked into a beautifully maintained neighborhood, 21 Russett Drive is the kind of home that feels welcoming the moment you arrive. Beautiful landscaping, a charming Dutch door, and a thoughtfully cared for yard give this property an almost secret garden feel private, inviting, and full of character.Inside, the versatility of this home truly shines. The main level offers a comfortable living

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    21 Russett Dr, Bennington, VT 05201
  • /6

    $1,050

    Total Monthly Price

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

    110 Short St Unit 3, Bennington, VT 05201

    2 bed 1 bath unit. First, last, security required at least signing. Credit and background checks required. No smoking. No pets.

    110 Short St Unit 3, Bennington, VT 05201
  • /48

    $295,000

    Sold Jul 22, 2026

    166 Cardinal Ln, Bennington, VT 05201

    • 3 Beds
    • 2 Baths
    • 2,753 Sq Ft
    • Built 1964

    Last Sold Summary

    • $107/SF
    • 16 Days On Market

    Current Estimated Value $303,218

    Last Listing Agent Monique Geannelis Mahar McCarthy Real Estate

    166 Cardinal Ln, Bennington, VT 05201
    • /35

      Est $241,012

      Not Listed For Sale

      115 Jefferson Ave, Bennington, VT 05201

      • 2 Beds
      • 2 Baths
      • 1,554 Sq Ft
      • Built 1930
      115 Jefferson Ave, Bennington, VT 05201

      Last Sold Summary

      • 83 Days On Market

      Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  • /40

    $450,000

    • 3 Beds
    • 1.5 Baths
    • 1,650 Sq Ft

    349 Elm St, Bennington, VT 05201

    Location!Welcome to this charming and very well maintained home on desirable Elm Street. Featuring three bedrooms and two bathrooms, this sweet property offers plenty of space, character, and versatility.One of the bedrooms has been thoughtfully transformed into a spacious walk-in closet/dressing room, but it can easily be converted back into a bedroom to restore the home's full

    Agent Photo

    Monique Geannelis

    Mahar McCarthy Real Estate

    349 Elm St, Bennington, VT 05201
  • /19

    $1,300

    Total Monthly Price

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

    178 S Branch St Unit 178, Bennington, VT 05201

    Second floor two bedroom in quiet neighborhood.- two good sized bedrooms, each with closet- living room- eat in kitchen with new floor- bathroom with shower stall- new windows- newer carpet / newly painted- great quiet neighborhood but still close to downtown- propane heat (tenant pays)- off peak electric hot water (tenant pays)- property owner pays for

    178 S Branch St Unit 178, Bennington, VT 05201
  • /30

    $345,750

    Sold Oct 21, 2025

    374 Overlea Rd, North Bennington, VT 05257

    • 3 Beds
    • 2 Baths
    • 1,753 Sq Ft
    • Built 1948

    Last Sold Summary

    • 5% Below List Price
    • $197/SF
    • 58 Days On Market

    Current Estimated Value $346,361

    Last Listing Agent Gregory Cutler Four Seasons Sotheby's Int'l Realty

    374 Overlea Rd, North Bennington, VT 05257
    • /33

      Est $398,782

      Not Listed For Sale

      60 Knoll Crest Ln, Bennington, VT 05201

      • 4 Beds
      • 2 Baths
      • 2,072 Sq Ft
      • Built 1948
      60 Knoll Crest Ln, Bennington, VT 05201

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Moira Spivey Four Seasons Sotheby's Int'l Realty

  • /7

    $55,000

    • Land
    • 22,215 Sq Ft
    • $107,843 per Acre

    24 Asa's Way, Bennington, VT 05257

    Build your future in the heart of North Bennington at 24 Asa's Way. This 0.51 acre corner lot offers a rare opportunity to create a custom home in a well established neighborhood surrounded by beautifully maintained properties. With mountain views and underground utilities already in place, the setting combines natural beauty with modern convenience.Public water and sewer are available,

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    24 Asa's Way, Bennington, VT 05257
  • /23

    $1,750

    Total Monthly Price

    • 3 Beds
    • 1.5 Baths
    • 1,500 Sq Ft
    • Condo for Rent

    203 Grandview St Unit 203, Bennington, VT 05201

    4 Bedroom / 1 Bath Duplex for Rent - Charm abounds in this 3 bedroom duplex!* Downstairs: 1 bedroom/home office, living room, kitchen and dining room* Upstairs: three bedrooms with grey painted floors* Heat is oil cast iron steam radiators; oil hot water tank* Newer electric stove and energy efficient fridge* Washer/dryer hookups in the basement* Not much of a yard, but

    203 Grandview St Unit 203, Bennington, VT 05201
  • /49

    $435,000

    Sold Oct 10, 2025

    458 Fox Hill Rd, Bennington, VT 05201

    • 4 Beds
    • 4 Baths
    • 3,040 Sq Ft
    • Built 2007

    Last Sold Summary

    • 2% Above List Price
    • $143/SF
    • 7 Days On Market

    Current Estimated Value $492,918

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    458 Fox Hill Rd, Bennington, VT 05201
    • /38

      Est $680,403

      Not Listed For Sale

      359 Hickory Hill Rd, Bennington, VT 05201

      • 3 Beds
      • 2.5 Baths
      • 2,184 Sq Ft
      • Built 2004
      359 Hickory Hill Rd, Bennington, VT 05201

      Last Sold Summary

      • 71 Days On Market

      Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  • /5

    $55,000

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

    29 Asa's 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

    29 Asa's Way, Bennington, VT 05257
  • /18

    $2,100

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,624 Sq Ft
    • House for Rent

    61 Bell St, Woodford, VT 05201

    Please read instructions below on how to tour or apply. The green "Request To Apply" button will cause a delay in our ability to respond.3br MANUFACTURED HOME for rent!*Open Floor Plan**Covered Porch**Fireplace*Unit: B-061Apply To: Mountain View CommunityRent: $2100/moBeds/Baths: 3 beds 2 bathsSize: 1,624 square feetPets: Cat & Dog friendly, all

    61 Bell St, Woodford, VT 05201
  • /28

    $265,000

    Sold Dec 15, 2025

    26 Cyr Ct, Bennington, VT 05201

    • 2 Beds
    • 1 Bath
    • 1,040 Sq Ft
    • Built 2000

    Last Sold Summary

    • $255/SF
    • 5 Days On Market

    Current Estimated Value $284,318

    Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate

    26 Cyr Ct, Bennington, VT 05201
    • /19

      Est $267,332

      Not Listed For Sale

      20 Rockwood St, Bennington, VT 05201

      • 3 Beds
      • 1 Bath
      • 1,070 Sq Ft
      • Built 1990
      20 Rockwood St, Bennington, VT 05201

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  • /31

    $595,000

    • Land
    • 23.62 Acres
    • $25,191 per Acre

    3213 West Rd, Bennington, VT 05201

    Some properties offer acreage, some offer breathtaking views, very few offer both along with a rich history worth preserving and a future waiting to be imagined. For generations, this rare south-facing farm has looked across the valley enjoying sunlight from dawn until dusk & panoramic views that are exceptional! More than productive farmland, it became a place where neighbors and families

    Agent Photo

    Monique Geannelis

    Mahar McCarthy Real Estate

    3213 West Rd, Bennington, VT 05201
  • /26

    $1,300

    Total Monthly Price

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

    172 S Branch St Unit 172, Bennington, VT 05201

    First floor two bedroom- walk to town- living room, dining room, kitchen, full bathroom with shower stall, comes with newer electric stove and fridge, washer/dryer hookups- heat is forced hot air (fuel oil)- rent DOES NOT INCLUDE utilities- I pay for lawncare, plowing and garbage- I take first month's rent, last month's rent and one month's rent as a security deposit (3x

    172 S Branch St Unit 172, Bennington, VT 05201
  • /16

    $96,906

    Sold Jul 18, 2026

    41 Audrey Ln, Bennington, VT 05201

    • 2 Beds
    • 2 Baths
    • 777 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Above List Price
    • $125/SF
    • 301 Days On Market

    Last Listing Agent Kate Barry EXP Realty

    41 Audrey Ln, Bennington, VT 05201
    • /57

      Est $206,782

      Not Listed For Sale

      100 Webb St, Bennington, VT 05201

      • 3 Beds
      • 1 Bath
      • 1,416 Sq Ft
      • Built 1943
      100 Webb St, Bennington, VT 05201

      Last Sold Summary

      • 75 Days On Market

      Last Listing Agent Lindsey Martin Maple Leaf Real Estate

  • /38

    $299,000

    $26K PRICE DROP
    • 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

    89 Merson St, Woodford, VT 05201
  • /11

    $2,125

    Total Monthly Price

    • 3 Beds
    • 1.5 Baths
    • 980 Sq Ft
    • House for Rent

    9 Mountain View Rd, Bennington, VT 05201

    Please read instructions below on how to tour or apply. The green "Request To Apply" button will cause a delay in our ability to respond.COMPLETELY RENOVATED 3br MANUFACTURED HOME for rent!*Large 2-CAR Garage!**Desirable Lot*Unit: M-009Apply To: Mountain View CommunityRent: $2125/moBeds/Baths: 3 beds 1.5 bathsSize: 980 square feetPets: Cat & Dog

    9 Mountain View Rd, Bennington, VT 05201
  • /43

    $625,000

    Sold Aug 31, 2026

    34 Monument Ave, Bennington, VT 05201

    • 4 Beds
    • 2.5 Baths
    • 2,692 Sq Ft
    • Built 1850

    Last Sold Summary

    • 1% Above List Price
    • $232/SF
    • 9 Days On Market

    Current Estimated Value $612,188

    Last Listing Agent Jeffrey Dorman

    34 Monument Ave, Bennington, VT 05201
    • /60

      Est $268,324

      Not Listed For Sale

      19 Robinson Ave, Bennington, VT 05201

      • 3 Beds
      • 1 Bath
      • 1,320 Sq Ft
      • Built 1954
      19 Robinson Ave, Bennington, VT 05201

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Floyd Amidon Maple Leaf Real Estate

  • /33

    $249,000

    $50K 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
  • /9

    $1,250 Per Month

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

    109 Mccall St Unit 3, Bennington, VT 05201

    *MANAGED BY HALE APARTMENTS*NO FEES CHARGED AT APPLICATION PROCESS, PLEASE BE AWARE OF SCAMS!This charming apartment offers a cozy and comfortable living space with two bedroom and one bathroom. Immerse yourself in the rich history of Bennington as you explore the vibrant downtown area, just steps away from your doorstep. The apartment boasts a convenient location, allowing you to

    109 Mccall St Unit 3, 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 $327,437

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    318 Chester Knoll Dr, Bennington, VT 05201
    • /53

      Est $440,395

      Not Listed For Sale

      495 Fairview St, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 1,309 Sq Ft
      • Built 2006
      495 Fairview St, Bennington, VT 05201

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Catherine Cairns Maple Leaf Real Estate

  • /36

    $198,000

    $22K PRICE DROP
    • Land
    • 54 Acres
    • $3,667 per Acre

    399 Bard Rd, Bennington, VT 05201

    Secluded serenity meets unmatched convenience on this sprawling 54+/- wooded acres in beautiful and historic Bennington, VT! Nestled among a lush mix of hard and softwoods teeming with wildlife, the property features a charming quarter-acre pond, perfect as a future homestead centerpiece, with your home set back just beyond the pond. Good access via a paved, town-maintained road leading to level

    Curtis Trousdale Preferred Properties

    399 Bard Rd, Bennington, VT 05201
  • /7

    $1,250 Per Month

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

    207 Maple St Unit 3, Bennington, VT 05201

    *MANAGED BY CRM, LLC*NO FEES CHARGED AT APPLICATION PROCESS, PLEASE BE AWARE OF SCAMS! Welcome to 207 Maple St. #3, located in the charming town of Bennington, VT. This cozy apartment offers 2 bedrooms and 1 bathroom, providing ample space for comfortable living. Situated in a prime location, this apartment is perfect for those seeking a convenient and hassle-free lifestyle.

    207 Maple St Unit 3, Bennington, 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 $309,840

    Last Listing Agent Vicki Wilson Maple Leaf Real Estate

    112 Norton St, Bennington, VT 05201
    • /4

      Not Listed For Sale

      29 Dustin Dr, Bennington, VT 05201

      • 2 Beds
      • 2 Baths
      • 777 Sq Ft
      • Built 2025
      29 Dustin Dr, Bennington, VT 05201

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Kate Barry EXP Realty

  • /27

    $209,900

    $10K PRICE DROP Under Contract
    • 2 Beds
    • 1 Bath
    • 1,075 Sq Ft

    1083 Main St, Bennington, VT 05201

    Charming two-bedroom, one-bath bungalow located just outside of Bennington. This inviting home features beautiful hardwood floors throughout, a spacious kitchen with a dedicated dining area, a comfortable living room, and a versatile office or study perfect for a variety of needs. Enjoy the convenience of main-level laundry and relax in the cozy three-season porch. Additional highlights include a

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    1083 Main St, Bennington, VT 05201
  • /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 $157,895

    Last Listing Agent Lindsey Martin Maple Leaf Real Estate

    235 Maple St, Bennington, VT 05201
    • /20

      Not Listed For Sale

      72 Ethans Way, Bennington, VT 05201

      • 2 Beds
      • 1 Bath
      • 825 Sq Ft
      • Built 2024
      72 Ethans Way, Bennington, VT 05201

      Last Sold Summary

      • 120 Days On Market

      Last Listing Agent Kate Barry EXP Realty

  • /29

    $250,000

    $50K PRICE DROP Under Contract
    • 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

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$286,900
Median Single Family Sale Price
$295,000
Median Townhouse Sale Price
$199,000
Median 2 Bedroom Sale Price
$250,000
Median 1 Bedroom Sale Price
$116,500
Average Price Per Sq Ft
$201
Number of Homes for Sale
5,202
Last 12 months Home Sales
110
Months of Supply
3.50
Median List Price
$295,500
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
11%
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