Bennington, VT Homes

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  /17

  $270,000 Pending

  • 6 Beds
  • 3 Baths
  • 2,900 Sq Ft

  239 - 241 Elm St, Bennington, VT 05201

  Located downtown, this three-unit building it offers a scenic view of Dewey Brook, which flows from the Walloomsac River. The property includes an unfinished space with the potential to add an additional unit, offering great investment upside. Recent updates include a brand-new roof installed this year. Shared driveway with MLS #5057052; seller is seeking to sell both properties together. Listing

  

  Erica Hale

  Ridgeline Real Estate

  (802) 278-6021

  239 - 241 Elm St, Bennington, VT 05201
• Explore Bennington

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  /2

  $1,100 per month

  • 1 Bed
  • 1 Bath
  • House for Rent

  165 Benmont Ave, Bennington, VT 05201

  Property Id: 1488761I bed 1 bath small house.The tenants pay their own utilities:heat electric etc…

  165 Benmont Ave, Bennington, VT 05201
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  /32

  $300,000 Sold May 15, 2025

  17 Tel Rd, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 2,272 Sq Ft
  • Built 1970

  Last Sold Summary

  • $132/SF
  • 6 Days On Market

  Current Estimated Value $342,740

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  17 Tel Rd, Bennington, VT 05201
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  /27

  Est $185,046 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,155 Sq Ft

  731 Main St, Bennington, VT 05201

  731 Main St, Bennington, VT 05201
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  /22

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 1,248 Sq Ft

  203 Northside Dr, Bennington, VT 05201

  Welcome to 203–205 Northside Drive, a truly unique property that combines residential living with commercial potential all in one. Are you looking for the flexibility to live in an apartment while generating income from multiple rental units, or would you prefer to restore the property back into a spacious single-family residence? This property gives you both options. Currently configured with

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 471-3591

  203 Northside Dr, Bennington, VT 05201
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  /7

  $850 per month

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

  318 School St Unit 125 Adams, Bennington, VT 05201

  318 School St Unit 125 Adams, Bennington, VT 05201
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  /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 $357,004

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

  374 Overlea Rd, North Bennington, VT 05257
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  /35

  Est $245,859 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,184 Sq Ft

  312 School St Unit 314, Bennington, VT 05201

  312 School St Unit 314, Bennington, VT 05201
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  /26

  $295,000 Pending

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

  235 Elm St Unit 3, Bennington, VT 05201

  This three-unit building features one unit per floor and is ideally located downtown. Set back from the road, it offers a scenic view of Dewey Brook, which flows from the Walloomsac River. Highlights include a large back deck, a spacious partially fenced yard, and a shared driveway with MLS #5057051. The seller prefers to sell both properties together. Listing agent is related to the seller.

  

  Erica Hale

  Ridgeline Real Estate

  (802) 210-4437

  235 Elm St Unit 3, Bennington, VT 05201
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  /59

  $2,200 per month

  • 2 Beds
  • 2.5 Baths
  • 1,265 Sq Ft
  • House for Rent

  212 Dewey St, Bennington, VT 05201

  This property is available now, and is fully furnished. Water/sewer included. The whole interior of the home has just been repainted in the last couple of years. Wood floors sanded. New stove. New Washer and Dryer, new flooring in the kitchen. Two bedrooms, 2.5 baths. The basement holds huge potential for storage. Small back deck to enjoy the creek. Two car garage. Just take a look at the photos

  212 Dewey St, Bennington, VT 05201
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  /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 $469,213

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  458 Fox Hill Rd, Bennington, VT 05201
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  /34

  Est $486,147 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,901 Sq Ft

  647 Fox Hill Rd, Bennington, VT 05201

  647 Fox Hill Rd, Bennington, VT 05201
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  /58

  $299,000

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft

  207 Silver St, Bennington, VT 05201

  Tastefully renovated antique home that retained it character 4 bed 2 bath home with gleaming hardwood floor in through out with Vinyl plank in the bathrooms and Laundry room. The downstairs Ensuite is currently being used as an in home office with private entrance. This would make a great room for a in-law space with private bath and the 3 season sunroom could easily be converted into a

  Dan Mason Perrott Realty

  207 Silver St, Bennington, VT 05201
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  /8

  $1,250 per month

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

  180 Northbranch St Unit B, Woodford, VT 05201

  180 Northbranch St Unit B, Woodford, VT 05201
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  /28

  $398,350 Sold Sep 04, 2025

  315 Chester Knoll Dr, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 2025

  Last Sold Summary

  • $246/SF
  • 0 Days On Market

  Last Listing Agent Lilli West Maple Leaf Realty

  315 Chester Knoll Dr, Bennington, VT 05201
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  /39

  Est $562,499 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,336 Sq Ft

  557 Fox Hill Rd, Bennington, VT 05201

  557 Fox Hill Rd, Bennington, VT 05201
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  /47

  $625,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft

  682 Fox Hill Rd, Bennington, VT 05201

  Soak up the mountain view from a brand new custom built home. Desirable neighborhood with paved town maintained roads. Just outside of Old Bennington and close to SVMC hospital, downtown restaurants and theaters. An easy commute to Bennington College, 22 minute drive to Williamstown, MA or an hour to Albany Int'l Airport. Nestled at the base of Mount Anthony, hikers will appreciate direct access

  Jenifer Prouty Hoffman Hoffman Real Estate

  682 Fox Hill Rd, Bennington, VT 05201
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  /10

  $1,550 per month

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

  36 W Road Park, Woodford, VT 05201

  Please don't click the "Request To Apply" button as it will cause a delay in our ability to respond to you. Read below for instructions on how to apply.3br MANUFACTURED HOME Available for rent!Unit: 36Apply To: West Road CommunityRent: $1550/moBeds/Baths: 3 beds 1.5 bathsSize: 924 square feetPets: Cat & Dog friendly, all animals must be approved. Pet deposit

  36 W Road Park, Woodford, VT 05201
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  /34

  $175,000 Sold May 16, 2025

  106 Park St Unit 8, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft
  • Built 1993

  Last Sold Summary

  • $166/SF
  • 9 Days On Market

  Current Estimated Value $197,716

  Last Listing Agent Vicki Wilson Maple Leaf Realty

  106 Park St Unit 8, Bennington, VT 05201
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  /38

  Est $664,634 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,266 Sq Ft

  3347 West Rd, Bennington, VT 05201

  3347 West Rd, Bennington, VT 05201
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  /18

  $300,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,570 Sq Ft

  940 Gage St, Bennington, VT 05201

  Classic cape with a twist! The eat-in kitchen has plenty of cooking area plus an eat-in area in a windowed alcove. The dining room is large enough for sit downs and the living room is the whole length of the house so movie nights are a go! In the entry side of the house you have a wonderful enclosed porch to serve as a mud room and a sweet sitting porch out front. AND!!!!... there is a fenced in

  Christine Lewis Brattleboro Area Realty

  940 Gage St, Bennington, VT 05201
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  /11

  $1,575 per month

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

  218 Abbott St, Bennington, VT 05201

  Please don't click the "Request To Apply" button as it will cause a delay in our ability to respond to you. Read below for instructions on how to apply.3br MANUFACTURED HOME for rent!Unit: A-218Apply To: Mountain View CommunityRent: $1575/moBeds/Baths: 3 beds 1.5 bathsSize: 980 square feetPets: Cat & Dog friendly, all animals must be approved. Pet deposit not

  218 Abbott St, Bennington, VT 05201
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  /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

  Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate

  26 Cyr Ct, Bennington, VT 05201
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  /19

  Est $155,549 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 975 Sq Ft

  1 Division Place, Bennington, VT 05201

  1 Division Place, Bennington, VT 05201
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  /54

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 2,715 Sq Ft

  58 Mount Anthony Rd, Bennington, VT 05201

  Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can

  Monique Geannelis Mahar McCarthy Real Estate

  58 Mount Anthony Rd, Bennington, VT 05201
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  /50

  $1,800 per month

  • 4 Beds
  • 1.5 Baths
  • 1,750 Sq Ft
  • Condo for Rent

  129 Grandview St Unit 129, Bennington, VT 05201

  Very large 1,750 square foot apartment (don't hold me to that exact figure)* 9 foot ceilings on both first floor and second floor. Great space, charming* Has the old world feel to it. Building was erected in the late 1800s* It has a living room, dining room (with bay window) and home office on the first floor* It also has a decent sized kitchen on the first floor with fully

  129 Grandview St Unit 129, Bennington, VT 05201
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  /20

  $90,000 Sold Apr 17, 2025

  105 Spring St, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,520 Sq Ft
  • Built 1903

  Last Sold Summary

  • 10% Below List Price
  • $59/SF
  • 4 Days On Market

  Current Estimated Value $104,483

  Last Listing Agent Matt Waddington Hoffman Real Estate

  105 Spring St, Bennington, VT 05201
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  /21

  Est $165,537 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  106 Park St Unit 16, Bennington, VT 05201

  106 Park St Unit 16, Bennington, VT 05201
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  /32

  $295,000

  • 1 Bed
  • 1.5 Baths
  • 1,680 Sq Ft

  318 North St, Bennington, VT 05201

  A former florist shop for 2 decades, this mixed-use property is now a blank slate ready for your vision. Zoning allows for retail, food/drink/entertainment, gallery or studio, personal or professional services, to multi-family or single-family residential. First floor and basement previously served as retail space, but with the walk-in cooler now removed, the main level feels significantly

  Jenifer Prouty Hoffman Hoffman Real Estate

  318 North St, Bennington, VT 05201
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  /26

  $1,300 per month

  • 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
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  /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 $211,929

  Last Listing Agent Lindsey Martin Maple Leaf Realty

  100 Webb St, Bennington, VT 05201
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  /29

  Est $518,890 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,752 Sq Ft

  9378 Vt Route 9, Bennington, VT 05201

  9378 Vt Route 9, Bennington, VT 05201
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  /40

  $695,000

  • 3 Beds
  • 2.5 Baths
  • 2,868 Sq Ft

  134 Monument Ave, Bennington, VT 05201

  Sprawling Cape on the Edge of Historic Old Bennington. Welcome to this beautiful and spacious Cape-style home offering warmth, character, and comfort in a highly desirable location. The inviting main level features a large kitchen, a sun-filled living room with a fireplace, and an expansive family room with a dining area-deal for entertaining or relaxing. A private office and a serene primary

  Kelley Mccarthy Mahar McCarthy Real Estate

  134 Monument Ave, Bennington, VT 05201
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  /44

  $1,350 per month

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

  254 Union St Unit B, Bennington, VT 05201

  Second Floor Renovated Two Bedroom Apartment- second floor 2 bedroom, each bedroom has a closet- renovated, new windows and entry door- washer/dryer hookups in kitchen- new stove, new fridge- egress windows and carbon monoxide detectors- includes heat, garbage, plowing and lawncare- tenant pays hot water (electric) and electric - all new!- walk to all amenities,

  254 Union St Unit B, Bennington, VT 05201
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  /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
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  /16

  Est $215,599 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,005 Sq Ft

  214 Hickory Rd, Bennington, VT 05201

  214 Hickory Rd, Bennington, VT 05201
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  /58

  $259,900 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,432 Sq Ft

  341 Dewey St, Bennington, VT 05201

  Built in 1900, this delightful single-level cottage is full of character and charm. Lovingly relocated to its current setting, it once served as the home of Marge’s Beauty Nook in 1971 and still carries a sense of cozy nostalgia. Open the windows and let the gentle sound of the babbling brook drift inside, or sip your morning coffee on the covered front porch with easy-care Trex decking—an

  Justine Curry Maple Leaf Realty

  341 Dewey St, Bennington, VT 05201
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  /18

  $1,500 per month

  • 2 Beds
  • 1.5 Baths
  • 852 Sq Ft
  • Condo for Rent

  432 South St Unit B4, Bennington, VT 05201

  Discover a delightful living experience at 432 South St. Unit B4, a welcoming 2-bedroom, 1.5-bathroom condo nestled in the highly sought-after Nathaniel Court neighborhood of Bennington, VT. Enjoy a range of amenities, including laundry hookups, a dedicated parking space, lawn care, plowing, and garbage taken care of by the association. Please note that pet will not be considered and smoking

  432 South St Unit B4, Bennington, VT 05201
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  /41

  $410,000 Sold Oct 17, 2025

  882 East Rd, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 1,792 Sq Ft
  • Built 2002

  Last Sold Summary

  • 3% Above List Price
  • $229/SF
  • 14 Days On Market

  Current Estimated Value $444,355

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  882 East Rd, Bennington, VT 05201
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  /47

  Est $435,498 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,686 Sq Ft

  201 Erbs Way, Bennington, VT 05201

  201 Erbs Way, Bennington, VT 05201

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