Bennington, VT Homes

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  /25

  $289,000 Under Contract

  • 7 Beds
  • 6 Baths
  • 5,712 Sq Ft

  136 North St, Bennington, VT 05201

  Downtown mixed-use investment opportunity located on North Street near the Four Corners intersection of Routes 7 and 9 in the heart of Bennington. The property features six total units, including four residential apartments (three two-bedroom units and one one-bedroom unit) and two street-level commercial storefronts with direct North Street frontage providing strong visibility for retail,

  Jeffrey Dorman

  136 North St, Bennington, VT 05201
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  /24

  $190,000 Sold May 07, 2025

  105 County St, Bennington, VT 05201

  • 5 Beds
  • 3 Baths
  • 2,270 Sq Ft
  • Built 1910

  Last Sold Summary

  • $84/SF
  • 6 Days On Market

  Current Estimated Value $202,929

  Last Listing Agent Erica Hale Ridgeline Real Estate

  105 County St, Bennington, VT 05201
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  /37

  Est $353,036 Not Listed For Sale

  163 Morgan St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,714 Sq Ft
  • Built 1948

  163 Morgan St, Bennington, VT 05201

  Last Sold Summary

  • 11% Below List Price
  • $230/SF
  • 6 Days On Market

  Last Sold Price $395,000

  Last Listing Agent Abi Gregorio
• 

  

  

  /17

  $79,900 Pending

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  108 Baker Dr, Bennington, VT 01237

  Built in 2000 this charming home is located in Catamount Mobile Home Park, a community with no age restrictions in beautiful Bennington, Vermont. Situated on a large corner lot with front and back decks offering mountain views. Open, light-filled floor plan with bright kitchen, living room, primary suite, second bedroom, full bath, and laundry. Features include anewer shed (1 year old) and

  Colleen Zajac MONARCH REALTY, INC.

  108 Baker Dr, Bennington, VT 01237
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  /37

  $256,250 Sold Sep 03, 2025

  1236 Morgan St, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 1,259 Sq Ft
  • Built 1940

  Last Sold Summary

  • 2% Above List Price
  • $204/SF
  • 7 Days On Market

  Current Estimated Value $252,215

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  1236 Morgan St, Bennington, VT 05201
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  /30

  Est $198,224 Not Listed For Sale

  101 Coulter St, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 2,603 Sq Ft
  • Built 1947

  101 Coulter St, Bennington, VT 05201

  Last Sold Summary

  • 40% Below List Price
  • $126/SF
  • 15 Days On Market

  Last Sold Price $328,000

  Last Listing Agent Angela Bevin Maple Leaf Realty
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  /26

  $199,000

  • 4 Beds
  • 2 Baths
  • 1,980 Sq Ft

  210 Division St, Bennington, VT 05201

  Turnkey Two-Unit Investment Opportunity in a Prime Downtown Location!This beautifully renovated duplex is perfect for a first-time investor or owner-occupant looking to build equity while generating income. The property features a two-bedroom unit and a one-bedroom unit, both thoughtfully updated and well maintained.The first-floor unit has been fully renovated, including an updated

  Lilli West Maple Leaf Realty

  210 Division St, Bennington, VT 05201
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  /35

  $220,000 Sold Sep 16, 2025

  115 Jefferson Ave, Bennington, VT 05201

  • 2 Beds
  • 2 Baths
  • 1,554 Sq Ft
  • Built 1930

  Last Sold Summary

  • 18% Below List Price
  • $142/SF
  • 83 Days On Market

  Current Estimated Value $225,623

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  115 Jefferson Ave, Bennington, VT 05201
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  /6

  Est $330,684 Not Listed For Sale

  240 Grandview St, Bennington, VT 05201

  • 3 Beds

  240 Grandview St, Bennington, VT 05201

  Last Sold Summary

  • 660% Above List Price
  • $31/SF
  • 38 Days On Market

  Last Sold Price $43,500

  Last Listing Agent Lindsey Martin Maple Leaf Realty
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  /4

  $350,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,190 Sq Ft

  523 Jennings Brook Dr, Bennington, VT 05201

  Brand new 2026 construction offering the ease of single-level living with thoughtful, ADA-compliant design throughout. This energy-efficient home features 2 bedrooms and 2 full bathrooms, including a well-designed primary suite, plus convenient in-unit laundry. The open-concept layout is highlighted by a spacious kitchen and a cathedral ceiling that brings in abundant natural light and an airy

  Lilli West Maple Leaf Realty

  523 Jennings Brook Dr, Bennington, VT 05201
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  /60

  $245,000 Sold Sep 22, 2025

  19 Robinson Ave, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft
  • Built 1954

  Last Sold Summary

  • 11% Below List Price
  • $186/SF
  • 3 Days On Market

  Current Estimated Value $249,735

  Last Listing Agent Floyd Amidon Maple Leaf Realty

  19 Robinson Ave, Bennington, VT 05201
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  /5

  Not Listed For Sale

  236 Grandview St, Bennington, VT 05201

  • 5 Beds
  • Built 1875

  236 Grandview St, Bennington, VT 05201

  Last Sold Summary

  • $16/SF
  • 38 Days On Market

  Last Sold Price $43,500

  Last Listing Agent Lindsey Martin Maple Leaf Realty
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  /8

  $65,000

  • Land
  • 1.24 Acres
  • $52,419 per Acre

  2041 East Rd, Bennington, VT 05201

  Partial cleared 1.2 acre lot where you can listen the stream flow as you watch the abundant wild life.

  Dan Mason Perrott Realty

  2041 East Rd, Bennington, VT 05201
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  /37

  $233,000 Sold Aug 04, 2025

  73 Woodford City Rd, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1984

  Last Sold Summary

  • 2% Above List Price
  • $221/SF
  • 73 Days On Market

  Last Listing Agent Abi Gregorio

  73 Woodford City Rd, Bennington, VT 05201
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  /30

  Est $305,605 Not Listed For Sale

  402 Jefferson Heights, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,712 Sq Ft
  • Built 1953

  402 Jefferson Heights, Bennington, VT 05201

  Last Sold Summary

  • 13% Above List Price
  • $158/SF
  • 72 Days On Market

  Last Sold Price $270,000

  Last Listing Agent Dick Thackston R.H. Thackston & Company
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  /33

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  254 Union St, Bennington, VT 05201

  Welcome to this well-maintained, solid income-producing two-family home located in the heart of town—just steps from shops, dining, and downtown events. Perfect for owner-occupants or savvy investors, this property combines classic charm with modern efficiency and low operating costs. Each two-bedroom unit features spacious, light-filled living areas, eat-in kitchen and comfortable bedrooms.

  Cassie Barbeau Mahar McCarthy Real Estate

  254 Union St, Bennington, VT 05201
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  /49

  $313,000 Sold Jul 21, 2025

  1385 N Bennington Rd, North Bennington, VT 05257

  • 4 Beds
  • 2 Baths
  • 2,050 Sq Ft
  • Built 1910

  Last Sold Summary

  • 1% Below List Price
  • $153/SF
  • 53 Days On Market

  Current Estimated Value $321,049

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  1385 N Bennington Rd, North Bennington, VT 05257
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  /24

  Est $301,604 Not Listed For Sale

  15 Greenview Dr, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 1,102 Sq Ft
  • Built 1993

  15 Greenview Dr, Bennington, VT 05201

  Last Sold Summary

  • 8% Above List Price
  • $254/SF
  • 6 Days On Market

  Last Sold Price $280,000

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
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  /29

  $399,000

  • 6 Beds
  • 3 Baths
  • 5,208 Sq Ft

  126 Washington Ave, Bennington, VT 05201

  Circa 1913 carriage barn converted into a mixed-use property in the heart of downtown Bennington. This distinctive 5,208± sq. ft. building combines residential and commercial opportunity, featuring three apartments and a ground-floor retail space. Original architectural details evoke the property’s historic character, while modern updates support comfortable living and reliable income potential.

  Vicki Wilson Maple Leaf Realty

  126 Washington Ave, Bennington, VT 05201
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  /36

  $265,000 Sold Jun 25, 2025

  82 Oakes St, Bennington, VT 05201

  • 2 Beds
  • 1 Bath
  • 1,512 Sq Ft
  • Built 1991

  Last Sold Summary

  • $175/SF
  • 57 Days On Market

  Current Estimated Value $264,430

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  82 Oakes St, Bennington, VT 05201
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  /38

  Est $355,496 Not Listed For Sale

  150 Pine Cir, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 1,592 Sq Ft
  • Built 2005

  150 Pine Cir, Bennington, VT 05201

  Last Sold Summary

  • 2% Above List Price
  • $220/SF
  • 63 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Brandy Lesser
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  /37

  $225,000

  • 2 Beds
  • 2 Baths
  • 911 Sq Ft

  726 Rice Ln, Bennington, VT 05201

  Welcome to this charming Cape-style home, nestled in a peaceful country setting just moments from Bennington College and scenic walking and hiking trails. This inviting property offers the perfect blend of rural tranquility and convenient access to town. Located just 10 minutes from downtown Bennington, you’ll have quick access to local shops, restaurants, cultural attractions, and everyday

  Thomas Martins Maple Leaf Realty

  726 Rice Ln, Bennington, VT 05201
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  /16

  $130,000 Sold Jan 28, 2026

  755 Main St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,485 Sq Ft
  • Built 1890

  Last Sold Summary

  • 10% Below List Price
  • $88/SF
  • 141 Days On Market

  Current Estimated Value $172,193

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

  755 Main St, Bennington, VT 05201
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  /25

  Est $385,102 Not Listed For Sale

  145 Pine Cir, Bennington, VT 05201

  • 4 Beds
  • 3 Baths
  • 1,560 Sq Ft
  • Built 1975

  145 Pine Cir, Bennington, VT 05201

  Last Sold Summary

  • 22% Above List Price
  • $202/SF
  • 12 Days On Market

  Last Sold Price $315,000

  Last Listing Agent Max Squiers KW Vermont - Brenda Jones Real Estate Group
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  /8

  $59,000

  • Land
  • 0.29 Acre
  • $203,448 per Acre

  420 Burgess Rd, Bennington, VT 05201

  Level building lot with town sewer and water at the edge of town.Possible owner financing.

  Dan Mason Perrott Realty

  420 Burgess Rd, Bennington, VT 05201
• 

  

  /38

  $215,000 Sold Jun 06, 2025

  230 Beech St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,271 Sq Ft
  • Built 1880

  Last Sold Summary

  • 4% Below List Price
  • $169/SF
  • 81 Days On Market

  Current Estimated Value $222,557

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  230 Beech St, Bennington, VT 05201
• 

  

  /39

  Est $419,415 Not Listed For Sale

  153 Pine Cir, Bennington, VT 05201

  • 3 Beds
  • 3 Baths
  • 1,528 Sq Ft
  • Built 1968

  153 Pine Cir, Bennington, VT 05201

  Last Sold Summary

  • 5% Above List Price
  • $262/SF
  • 14 Days On Market

  Last Sold Price $400,000

  Last Listing Agent Brandy Lesser
• 

  /2

  $45,000

  • Land
  • 2.21 Acres
  • $20,362 per Acre

  105 Nelson Rd, Bennington, VT 05201

  Property has 2.21 acres; land is mostly level and partially cleared. Located close to Downtown Bennington.

  Timothy Corcoran Mahar McCarthy Real Estate

  105 Nelson Rd, Bennington, VT 05201
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  /14

  $278,000 Sold Aug 04, 2025

  400 South St, Bennington, VT 05201

  • 3 Beds
  • 3 Baths
  • 1,461 Sq Ft
  • Built 1825

  Last Sold Summary

  • 7% Above List Price
  • $190/SF
  • 38 Days On Market

  Current Estimated Value $282,250

  Last Listing Agent William Paquin Maple Leaf Realty

  400 South St, Bennington, VT 05201
• 

  

  /19

  Est $250,028 Not Listed For Sale

  314 Prospect St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,482 Sq Ft
  • Built 1940

  314 Prospect St, Bennington, VT 05201

  Last Sold Summary

  • 9% Above List Price
  • $155/SF
  • 10 Days On Market

  Last Sold Price $230,000

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
• 

  

  /10

  $1,950,000

  • Land
  • 7 Acres
  • $278,571 per Acre

  720 N Branch St, Bennington, VT 05201

  Discover the potential at 720 & 702 North Branch Street—a rare 7-acre offering in a prime Bennington location. With level land, generous frontage, and easy access, this property is perfectly positioned for residential or mixed-use development, with municipal water and sewer available at the street.The sale includes a well-maintained duplex at 702 North Branch, featuring a 3-bedroom unit

  Paul Carroccio TPW Real Estate

  720 N Branch St, Bennington, VT 05201
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  /38

  $193,800 Sold May 30, 2025

  134 Imperial Ave, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1915

  Last Sold Summary

  • 2% Above List Price
  • $192/SF
  • 31 Days On Market

  Current Estimated Value $195,361

  Last Listing Agent Angela Bevin Maple Leaf Realty

  134 Imperial Ave, Bennington, VT 05201
• 

  

  /27

  Est $222,633 Not Listed For Sale

  317 Prospect St, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,274 Sq Ft
  • Built 1940

  317 Prospect St, Bennington, VT 05201

  Last Sold Summary

  • 13% Below List Price
  • $200/SF
  • 6 Days On Market

  Last Sold Price $255,000

  Last Listing Agent Angela Bevin Maple Leaf Realty
• 

  

  /33

  $265,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,064 Sq Ft

  1758 East Rd, Bennington, VT 05201

  Welcome to this thoughtfully cared-for 2-bedroom, 1-bath ranch located on desirable East Road in Bennington. Offering easy one-level living and meaningful upgrades, this home delivers both practicality and long-term value. Inside, you’ll find a bright and efficient layout featuring an updated kitchen and refreshed bath, along with a recently updated boiler and new energy-efficient mini-split

  Morriah Adams BHG Masiello Brattleboro

  1758 East Rd, Bennington, VT 05201
• 

  

  /30

  $310,000 Sold Jul 25, 2025

  198 Weeks St, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 2,032 Sq Ft
  • Built 1930

  Last Sold Summary

  • 11% Below List Price
  • $153/SF
  • 54 Days On Market

  Current Estimated Value $325,962

  Last Listing Agent Margretta Fischer Wohler Realty Group

  198 Weeks St, Bennington, VT 05201
• 

  

  /5

  Not Listed For Sale

  108 Norton St, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,432 Sq Ft
  • Built 1935

  108 Norton St, Bennington, VT 05201

  Last Sold Summary

  • $122/SF
  • 48 Days On Market

  Last Sold Price $174,000

  Last Listing Agent Diana LaPerle KW Vermont - Barre
• 

  

  /35

  $575,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,535 Sq Ft

  704 Fox Hill Rd, Bennington, VT 05201

  House hunting in Vermont and can't find what you want? Or it sold before you had time to tour or think it through? This brand new custom built home could be the answer. Desirable neighborhood with paved town roads, close to SVMC hospital, Bennington College, downtown restaurants and events, and one hour from Albany Int'l Airport. Nestled at the base of Mount Anthony, there's direct access to the

  Jenifer Prouty Hoffman Hoffman Real Estate

  704 Fox Hill Rd, Bennington, VT 05201
• 

  

  /57

  $275,000 Sold Aug 07, 2025

  115-117 Norton St, Bennington, VT 05201

  • 2 Beds
  • 2 Baths
  • 1,701 Sq Ft
  • Built 1930

  Last Sold Summary

  • $162/SF
  • 0 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  115-117 Norton St, Bennington, VT 05201
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  /28

  Est $200,043 Not Listed For Sale

  234 Grandview St, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 3,809 Sq Ft
  • Built 1850

  234 Grandview St, Bennington, VT 05201

  Last Sold Summary

  • 38% Above List Price
  • $38/SF
  • 15 Days On Market

  Last Sold Price $145,000

  Last Listing Agent Lilli West Maple Leaf Realty
• 

  

  /44

  $450,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,152 Sq Ft

  32 Cortland Ln, Bennington, VT 05201

  This well-maintained 1999 Colonial offers the perfect blend of timeless design, functional space, and peaceful surroundings in a desirable neighborhood just outside of town. Set on a wooded lot with a wrap-around covered front porch, this home invites you to slow down and enjoy the best of Vermont living. Inside, you’ll find over 2,100 square feet of thoughtfully designed living space with a

  Jenifer Prouty Hoffman Hoffman Real Estate

  32 Cortland Ln, Bennington, VT 05201

Showing Results 121 - 160, Page 4 of 18