Bennington, VT Homes

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  /40

  $185,000 Sold Jul 25, 2025

  305 Grove St, Bennington, VT 05201

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Built 2016

  Last Sold Summary

  • 3% Above List Price
  • $231/SF
  • 28 Days On Market

  Current Estimated Value $199,387

  Last Listing Agent Justine Curry Maple Leaf Realty

  305 Grove St, Bennington, VT 05201
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  /40

  Est $332,137 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft

  505 Cross Rd, Bennington, VT 05201

  505 Cross Rd, Bennington, VT 05201
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  /15

  $96,906 New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  10 Cassie Ln, Bennington, VT 05201

  Welcome to 10 Cassie Lane, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  10 Cassie Ln, Bennington, VT 05201
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  /28

  $213,200 Sold May 30, 2025

  1004 Main St, Bennington, VT 05201

  • 5 Beds
  • 3 Baths
  • 1,872 Sq Ft
  • Built 1920

  Last Sold Summary

  • 2% Above List Price
  • $114/SF
  • 50 Days On Market

  Current Estimated Value $246,293

  Last Listing Agent Erica Hale Ridgeline Real Estate

  1004 Main St, Bennington, VT 05201
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  /40

  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,976 Sq Ft

  260 Tower Rd, Bennington, VT 05201

  260 Tower 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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  /19

  $141,000 Sold Jun 03, 2025

  432 South St Unit C7, Bennington, VT 05201

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

  Last Sold Summary

  • 4% Below List Price
  • $172/SF
  • 46 Days On Market

  Current Estimated Value $165,104

  Last Listing Agent Abi Gregorio

  432 South St Unit C7, Bennington, VT 05201
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  /40

  Est $416,749 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,163 Sq Ft

  42 Maple Grove Rd, Bennington, VT 05201

  42 Maple Grove Rd, Bennington, VT 05201
• 

  

  /50

  $230,000

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  113 Main St, Bennington, VT 05201

  Charming downtown family home with modern upgrades.This beautifully updated 3-bedroom home is perfectly situated on a desirable corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, with a recent addition of a first-floor primary bedroom and new mudroom back entrance.Step inside to find gleaming hardwood floors and a warm, inviting layout. The dining

  Lindsey Martin Maple Leaf Realty

  113 Main St, Bennington, VT 05201
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  /19

  $225,000 Sold Aug 29, 2025

  1801 S Stream Rd, Bennington, VT 05201

  • Land
  • 16.68 Acres
  • $13,489 per Acre

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  1801 S Stream Rd, Bennington, VT 05201
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  /38

  Est $364,366 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft

  1063 Middle Pownal Rd, Bennington, VT 05201

  1063 Middle Pownal 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

  Jenifer Prouty Hoffman Hoffman Real Estate

  682 Fox Hill Rd, Bennington, VT 05201
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  /45

  $46,000 Sold Oct 10, 2025

  109 County St, Bennington, VT 05201

  • 4 Beds
  • 1 Bath
  • 1,146 Sq Ft
  • Built 1900

  Last Sold Summary

  • 42% Below List Price
  • $40/SF
  • 10 Days On Market

  Last Listing Agent Justine Curry Maple Leaf Realty

  109 County St, Bennington, VT 05201
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  /40

  Est $200,604 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,866 Sq Ft

  276 Finley Dr, Bennington, VT 05201

  276 Finley Dr, Bennington, VT 05201
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  /18

  $300,000

  • 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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  /4

  $45,000 Sold Oct 06, 2025

  45 Shady Ln, Bennington, VT 05201

  • 4 Beds
  • 1 Bath
  • 1,142 Sq Ft
  • Built 1948

  Last Sold Summary

  • 25% Below List Price
  • $39/SF
  • 7 Days On Market

  Last Listing Agent Erika Floriani Hoffman Real Estate

  45 Shady Ln, Bennington, VT 05201
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  /35

  Est $243,676 Not Listed For Sale

  • 3 Beds

  1213 Gore Rd, Bennington, VT 05201

  1213 Gore Rd, Bennington, VT 05201
• 

  

  /19

  $219,500

  • 3 Beds
  • 1 Bath
  • 1,254 Sq Ft

  14 Robinson Ave, Bennington, VT 05201

  Discover this lovely three-bedroom, one-bathroom home featuring 1,254 square feet of finished space, all set on a .24-acre lot. Recent upgrades roughly in the last ten years include blown-in insulation, roof, furnace, and updated kitchen and flooring, making this home both comfortable and stylish. Perfect for families or anyone looking for a cozy place. Minutes from Mt. Anthony Country Club,

  Timothy Corcoran Mahar McCarthy Real Estate

  14 Robinson Ave, Bennington, VT 05201
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  /43

  $235,000 Sold Dec 08, 2025

  110 S Branch St, Bennington, VT 05201

  • 6 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 1928

  Last Sold Summary

  • 2% Below List Price
  • $98/SF
  • 9 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  110 S Branch St, Bennington, VT 05201
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  /40

  Est $554,951 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,706 Sq Ft

  402 Middle Pownal Rd, Bennington, VT 05201

  402 Middle Pownal Rd, 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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  /24

  $42,000 Sold Oct 24, 2025

  26 Asa's Way, Bennington, VT 05257

  • Land
  • 0.48 Acre
  • $87,500 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 55 Days On Market

  Last Listing Agent Angela Bevin Maple Leaf Realty

  26 Asa's Way, Bennington, VT 05257
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  /35

  Est $383,749 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,821 Sq Ft

  1351 Morgan St, Bennington, VT 05201

  1351 Morgan St, Bennington, VT 05201
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  /16

  $145,000 Under Contract

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

  755 Main St, Bennington, VT 05201

  Many possibilities with this property located on Main Street in Bennington. Zoned village commercial but currently a 3 bedroom 1 and a half bath home. Nice kitchen, dining room, living room, main level primary with half bath, main level laundry and more. Needs some TLC. Won't qualify for first time homebuyer programs.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  755 Main St, Bennington, VT 05201
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  /46

  $399,000 Sold Jul 28, 2025

  4 Bank St, Bennington, VT 05201

  • 3 Beds
  • 3 Baths
  • 1,728 Sq Ft
  • Built 1930

  Last Sold Summary

  • 6% Below List Price
  • $231/SF
  • 55 Days On Market

  Current Estimated Value $445,592

  Last Listing Agent Margretta Fischer Wohler Realty Group

  4 Bank St, Bennington, VT 05201
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  /40

  Est $594,691 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,952 Sq Ft

  88 Southshire Dr, Bennington, VT 05201

  88 Southshire Dr, Bennington, VT 05201
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  /12

  $35,300

  • 2 Beds
  • 1 Bath
  • 1,302 Sq Ft

  933 East Rd, Bennington, VT 05201

  Built in 1965, this one level home offers approximately 1302 finished square feet, two bedrooms and one full bath, fireplace, unfinished basement and deck. This home sits on an approximate 44867 sqft lot. This property is in uninhabitable condition and boarded up. UNSAFE TO ENTER, foundation cracked, fallen and caved in.

  Sherry Price REALHome Services and Solutions, Inc.

  933 East Rd, Bennington, VT 05201
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  /35

  $329,900 Sold Aug 28, 2025

  170 Brambley Ln, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,459 Sq Ft
  • Built 1969

  Last Sold Summary

  • $226/SF
  • 4 Days On Market

  Current Estimated Value $328,135

  Last Listing Agent Matt Waddington Hoffman Real Estate

  170 Brambley Ln, Bennington, VT 05201
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  /40

  Est $620,723 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,183 Sq Ft

  377 Southshire Dr, Bennington, VT 05201

  377 Southshire Dr, Bennington, VT 05201
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  /42

  $1,950,000

  • 9 Beds
  • 7 Baths
  • 6,956 Sq Ft

  1086 West Rd, Bennington, VT 05201

  Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining

  Chris DeFelice Four Seasons Sotheby's Int'l Realty

  1086 West Rd, Bennington, VT 05201
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  /42

  $325,000 Sold Jun 03, 2025

  209 Washington Ave, Bennington, VT 05201

  • 4 Beds
  • 4 Baths
  • 3,230 Sq Ft
  • Built 1900

  Last Sold Summary

  • 22% Below List Price
  • $101/SF
  • 52 Days On Market

  Current Estimated Value $329,254

  Last Listing Agent Wendy Larson Hooscik Realty

  209 Washington Ave, Bennington, VT 05201
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  /40

  Est $571,531 Not Listed For Sale

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

  179 Southshire Dr, Bennington, VT 05201

  179 Southshire Dr, Bennington, VT 05201
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  /4

  $249,000

  • 5 Beds
  • 3 Baths
  • 2,184 Sq Ft

  137 Park St, Bennington, VT 05201

  Terrific income producing property. 2 - 1 bedroom units and a 3 bedroom unit with a garage. Close to town and modern systems. Good rental history. Is in a flood zone but owner has found a good flood insurance company.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  137 Park St, Bennington, VT 05201
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  /54

  $225,000 Sold Sep 10, 2025

  304 North St Unit 6, Bennington, VT 05201

  • 4 Beds
  • 3 Baths
  • 2,162 Sq Ft
  • Built 1890

  Last Sold Summary

  • 5% Above List Price
  • $104/SF
  • 15 Days On Market

  Current Estimated Value $227,613

  Last Listing Agent Thomas Martins Maple Leaf Realty

  304 North St Unit 6, Bennington, VT 05201
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  /37

  Est $323,858 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,400 Sq Ft

  1065 Burgess Rd, Bennington, VT 05201

  1065 Burgess Rd, Bennington, VT 05201
• 

  

  /60

  $275,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  150 Fillmore St, Bennington, VT 05201

  Location, location, location! Own your own private oasis on a dead-end road with nearly 7 acres - only minutes from downtown shopping and dining. Enjoy seasonal mountain views from the deck with sliding doors to the open concept living/dining room with vaulted ceiling. The propane fireplace with gorgeous wood mantle keeps things toasty while providing cozy ambiance. The spacious kitchen has

  Justine Curry Maple Leaf Realty

  150 Fillmore St, Bennington, VT 05201
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  /45

  $750,500 Sold May 20, 2025

  688 Rice Ln, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 2,576 Sq Ft
  • Built 2015

  Last Sold Summary

  • 4% Above List Price
  • $291/SF
  • 27 Days On Market

  Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate

  688 Rice Ln, Bennington, VT 05201
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  /31

  Est $436,540 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,963 Sq Ft

  543 Gore Rd, Bennington, VT 05201

  543 Gore Rd, 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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  /39

  $383,000 Sold Jul 30, 2025

  224 Garbrooke Dr, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 2,207 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $174/SF
  • 61 Days On Market

  Current Estimated Value $420,944

  Last Listing Agent Lindsey Martin Maple Leaf Realty

  224 Garbrooke Dr, Bennington, VT 05201

Showing Results 41 - 80, Page 2 of 18