Bennington, VT Homes

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  $379,900 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,530 Sq Ft

  93 Russett Dr, Bennington, VT 05201

  Welcome to this charming mid-century home set on 1.27 acres, offering 4 bedrooms and 3 bathrooms. This property blends character, functionality, and unique design throughout.At the heart of the home, a beautiful open concept kitchen and living area creates the perfect space for gathering and entertaining. A stunning fireplace anchors the room, offering warmth and ambiance whether you’re

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 416-3661

  93 Russett Dr, Bennington, VT 05201
• Explore Bennington

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  /4

  $1,350 per month

  • 3 Beds
  • 1 Bath
  • Condo for Rent

  103 County St Unit 1, Bennington, VT 05201

  Property Id: 14887483 bed 1 bath apartment located at first floor.Tenants pay for their utilities:heat electric etc.

  103 County St Unit 1, Bennington, VT 05201
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  $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 $313,004

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  17 Tel Rd, Bennington, VT 05201
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  /33

  Est $221,941 Not Listed For Sale

  203 Scott St, Bennington, VT 05201

  • 4 Beds
  • 1.5 Baths
  • 1,788 Sq Ft
  • Built 1890

  203 Scott St, Bennington, VT 05201

  Last Sold Summary

  • 11% Above List Price
  • $112/SF
  • 291 Days On Market

  Last Sold Price $200,000

  Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate
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  $299,900 Under Contract

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

  318 Chester Knoll Dr, Bennington, VT 05201

  Are you looking for a beautifully maintained home close to downtown but not right in the middle of it? Welcome to 318 Chester Knoll.Located in a desirable development with scenic walking trails and sidewalks connecting you to downtown and local restaurants, this light filled three bedroom home offers the perfect blend of convenience and peaceful living.Tasteful updates completed within

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 788-8574

  318 Chester Knoll Dr, Bennington, VT 05201
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  $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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  $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 $371,563

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

  374 Overlea Rd, North Bennington, VT 05257
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  /27

  Est $182,724 Not Listed For Sale

  731 Main St, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 1,155 Sq Ft
  • Built 1900

  731 Main St, Bennington, VT 05201

  Last Sold Summary

  • 8% Above List Price
  • $146/SF
  • 7 Days On Market

  Last Sold Price $169,000

  Last Listing Agent Dana Haley Real Broker LLC
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  $295,000 Pending

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

  112 Norton St, Bennington, VT 05201

  Move-in ready 2BR/1.5BA ranch on a sunny 0.27-acre lot offering comfort, updates, and easy living—ideal for first-time buyers or those looking to downsize. This well-maintained home features efficient mini-split systems for year-round comfort, brand-new vinyl plank flooring, and a new 50-year architectural shingle roof installed in 2024 for long-term peace of mind. The fully insulated attached

  Vicki Wilson Maple Leaf Realty

  112 Norton St, Bennington, VT 05201
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  $2,500 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, plowing, and lawn care 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

  212 Dewey St, Bennington, VT 05201
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  $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 $445,269

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  458 Fox Hill Rd, Bennington, VT 05201
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  /35

  Est $250,230 Not Listed For Sale

  312 School St Unit 314, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 2,184 Sq Ft
  • Built 1908

  312 School St Unit 314, Bennington, VT 05201

  Last Sold Summary

  • 6% Above List Price
  • $109/SF
  • 3 Days On Market

  Last Sold Price $237,000

  Last Listing Agent Angela Bevin Maple Leaf Realty
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  $299,000 Under Contract

  • 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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  /10

  $1,200 per month

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

  318 School St Unit 318 School, Bennington, VT 05201

  318 School St Unit 318 School, Bennington, VT 05201
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  $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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  /34

  Est $468,731 Not Listed For Sale

  647 Fox Hill Rd, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 1,901 Sq Ft
  • Built 2008

  647 Fox Hill Rd, Bennington, VT 05201

  Last Sold Summary

  • 9% Above List Price
  • $226/SF
  • 133 Days On Market

  Last Sold Price $430,000

  Last Listing Agent Erika Floriani Hoffman Real Estate
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  /35

  $370,000

  • 3 Beds
  • 1.5 Baths
  • 1,463 Sq Ft

  303 Prospect St, Bennington, VT 05201

  Nestled on a quiet residential street, this beautifully maintained home effortlessly blends timeless charm with modern convenience, creating a space that is as inviting as it is impressive. From the moment you arrive, you’ll appreciate the character and warmth that set this property apart. At the heart of the home is a thoughtfully designed kitchen featuring modern appliances, rich cherry

  Angela Bevin Maple Leaf Realty

  303 Prospect St, Bennington, VT 05201
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  $1,400 per month

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

  203 - 205 Union St Unit 2 - Rear Downstairs, Bennington, VT 05201

  203 Union St, Downstairs Back ApartmentIncluded with rent: Heat, Lawncare, Hot Water, Water/SewerFreshly painted first floor unit available at 203 Union St for $1,400 per month.This unit offers a clean, freshly painted living space in a convenient location. The apartment is ready for immediate occupancy. There is a large porch area for extra storage.Rent: $1,400

  203 - 205 Union St Unit 2 - Rear Downstairs, Bennington, VT 05201
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  $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 $184,460

  Last Listing Agent Vicki Wilson Maple Leaf Realty

  106 Park St Unit 8, Bennington, VT 05201
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  Est $564,078 Not Listed For Sale

  557 Fox Hill Rd, Bennington, VT 05201

  • 4 Beds
  • 3.5 Baths
  • 2,336 Sq Ft
  • Built 2009

  557 Fox Hill Rd, Bennington, VT 05201

  Last Sold Summary

  • 11% Above List Price
  • $218/SF
  • 17 Days On Market

  Last Sold Price $510,000

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
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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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  $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 $266,466

  Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate

  26 Cyr Ct, Bennington, VT 05201
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  /38

  Est $659,570 Not Listed For Sale

  3347 West Rd, Bennington, VT 05201

  • 5 Beds
  • 3 Baths
  • 3,266 Sq Ft
  • Built 1969

  3347 West Rd, Bennington, VT 05201

  Last Sold Summary

  • 8% Above List Price
  • $187/SF
  • 20 Days On Market

  Last Sold Price $610,000

  Last Listing Agent Margretta Fischer Wohler Realty Group
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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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  /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 $96,561

  Last Listing Agent Matt Waddington Hoffman Real Estate

  105 Spring St, Bennington, VT 05201
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  /19

  Est $391,257 Not Listed For Sale

  1 Division Place, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 975 Sq Ft
  • Built 1895

  1 Division Place, Bennington, VT 05201

  Last Sold Summary

  • 213% Above List Price
  • $128/SF
  • 44 Days On Market

  Last Sold Price $125,000

  Last Listing Agent Vicki Wilson Maple Leaf Realty
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  /53

  $649,000

  • 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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  /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 $191,466

  Last Listing Agent Lindsey Martin Maple Leaf Realty

  100 Webb St, Bennington, VT 05201
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  /21

  Est $168,872 Not Listed For Sale

  106 Park St Unit 16, Bennington, VT 05201

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

  106 Park St Unit 16, Bennington, VT 05201

  Last Sold Summary

  • 9% Above List Price
  • $147/SF
  • 76 Days On Market

  Last Sold Price $155,000

  Last Listing Agent Peggy Winchester ACORN REAL ESTATE GROUP LLC
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  $425,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,030 Sq Ft

  848 Coleville Rd, Bennington, VT 05201

  The House that Love Built-Multigenerational Comfort &Thoughtful Design Tucked away in a peaceful neighborhood, set back from a well maintained town road. This beautifully maintained home is perfect for wildlife watching and enjoying serene solitude.Designed with multigenerational or accessible living in mind, the home features a private in-law suite with it's own ramp entry, wide doorways,

  Beatrice O'Connell Maple Leaf Realty

  848 Coleville Rd, Bennington, VT 05201
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  /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 $405,965

  Last Listing Agent Angela Bevin Maple Leaf Realty

  356 Elm St, Bennington, VT 05201
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  /29

  Est $484,956 Not Listed For Sale

  9378 Vt Route 9, Bennington, VT 05201

  • 4 Beds
  • 3 Baths
  • 1,752 Sq Ft
  • Built 1985

  9378 Vt Route 9, Bennington, VT 05201

  Last Sold Summary

  • 6% Above List Price
  • $261/SF
  • 6 Days On Market

  Last Sold Price $458,000

  Last Listing Agent Lisa Mirando Deerfield Valley Real Estate
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  $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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  $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 $258,425 Not Listed For Sale

  214 Hickory Rd, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,005 Sq Ft
  • Built 1960

  214 Hickory Rd, Bennington, VT 05201

  Last Sold Summary

  • 3% Above List Price
  • $249/SF
  • 14 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Lori Hurley Four Corner Properties LLC
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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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  $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 $408,465

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  882 East Rd, Bennington, VT 05201
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  Est $412,845 Not Listed For Sale

  201 Erbs Way, Bennington, VT 05201

  • 3 Beds
  • 3.5 Baths
  • 2,686 Sq Ft
  • Built 1974

  201 Erbs Way, Bennington, VT 05201

  Last Sold Summary

  • 6% Above List Price
  • $145/SF
  • 7 Days On Market

  Last Sold Price $389,000

  Last Listing Agent Vicki Wilson Maple Leaf Realty
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  $349,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,218 Sq Ft

  308 Elm St, Bennington, VT 05201

  Vermont charm meets move-in ready comfort on Elm Street! This inviting 3-bedroom, 2.5-bath Cape offers warm, welcoming spaces throughout. The cozy yet spacious living room features a fireplace — perfect for snowy Vermont evenings — while the generously sized dining room is ideal for hosting holidays and gatherings. The beautifully updated kitchen showcases granite countertops and rich cherry

  Kelley Mccarthy Mahar McCarthy Real Estate

  308 Elm St, Bennington, VT 05201

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