Bennington, VT Homes

• 

  

  

  /40

  Est $358,434

  Not Listed For Sale

  505 Cross Rd, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft
  • Built 2003

  505 Cross Rd, Bennington, VT 05201

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Vicki Wilson Maple Leaf Real Estate
• 

  

  

  /39

  $250,000

  $10K PRICE DROP Under Contract

  • 4 Beds
  • 1.5 Baths
  • 1,458 Sq Ft

  301 Elm St, Bennington, VT 05201

  Set on a 0.25-acre corner lot, this classic 4-bedroom home offers the space, character, and friendly atmosphere that make Elm Street so appealing. Sidewalks invite evening strolls and dog walks, neighbors gather on their porches, and it's a favorite destination for trick-or-treaters each Halloween. Next to the Elm Street Market, one block from Southwestern Vermont Medical Center, and close to

  Jenifer Prouty Hoffman Hoffman Real Estate

  301 Elm St, Bennington, VT 05201
• 

  

  

  /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

  Current Estimated Value $247,543

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  110 S Branch St, Bennington, VT 05201
• 

  

  

  /40

  Est $595,636

  Not Listed For Sale

  260 Tower Rd, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 3,976 Sq Ft
  • Built 1981

  260 Tower Rd, Bennington, VT 05201

  Last Sold Summary

  • 115 Days On Market

  Last Listing Agent Allison Pacelli Pacelli Zepka Corporation
• 

  

  

  /50

  $330,000

  $15K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,750 Sq Ft

  1141 Burgess Rd, Bennington, VT 05201

  Completely renovated, turnkey single-level home offering mountain views, modern finishes, and a beautiful country setting. All major systems and cosmetic updates were completed within the last year, including a brand-new roof and new windows.The light-filled interior layout features 2 bedrooms, 2 full bathrooms, brand-new wood flooring across all main living areas, plush new bedroom

  Kate Barry EXP Realty

  1141 Burgess Rd, Bennington, VT 05201
• 

  

  /24

  $42,000

  Sold Oct 24, 2025

  26 Asa's Way, Bennington, VT 05257

  • Land
  • 20,908 Sq Ft
  • $87,500 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 55 Days On Market

  Last Listing Agent Angela Bevin Maple Leaf Real Estate

  26 Asa's Way, Bennington, VT 05257
• 

  

  /40

  Est $445,061

  Not Listed For Sale

  42 Maple Grove Rd, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 2,163 Sq Ft
  • Built 1960

  42 Maple Grove Rd, Bennington, VT 05201

  Last Sold Summary

  • 87 Days On Market

  Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate
• 

  

  /27

  $179,000

  $20K PRICE DROP Under Contract

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

  432 South St Unit D2, Bennington, VT 05201

  Welcome to easy living at Nathaniel Court! This spacious and light-filled tri-level condo offers the perfect blend of comfort, flexibility, and convenience in the heart of Bennington. Privately situated in a standalone building at the edge of the development, this well-maintained 3BR, 3BA home features generous living spaces, abundant natural light, and dedicated parking. A rare opportunity to

  Abi Gregorio

  432 South St Unit D2, Bennington, VT 05201
• 

  

  /13

  $60,500

  Sold May 18, 2026

  1488 Morgan St, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,254 Sq Ft
  • Built 1959

  Last Sold Summary

  • 10% Above List Price
  • $48/SF
  • 14 Days On Market

  Current Estimated Value $255,353

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

  1488 Morgan St, Bennington, VT 05201
• 

  

  /36

  Not Listed For Sale

  1211 Carpenter Hill Rd, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1930

  1211 Carpenter Hill Rd, Bennington, VT 05201

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Peter West BISHOP WEST REAL ESTATE
• 

  

  /7

  $997,000

  • Land
  • 23,086 Sq Ft
  • $1,881,132 per Acre

  153 Northside Dr, Bennington, VT 05201

  Level, .53-acre lot situated in Bennington’s high-traffic Planned Commercial (PC) District. This site offers a rare opportunity to save significantly on demolition costs and move straight into the design and permitting phase for a new commercial project. This busy corridor lot is located entirely outside of the flood zone, providing a clean slate for development and a more streamlined path for

  Lori Hurley Four Corner Properties LLC

  153 Northside Dr, Bennington, VT 05201
• 

  

  /44

  $287,800

  Sold Jul 09, 2026

  935 Gage St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,265 Sq Ft
  • Built 1945

  Last Sold Summary

  • 7% Above List Price
  • $228/SF

  Current Estimated Value $283,315

  Last Listing Agent Lilli West Maple Leaf Real Estate

  935 Gage St, Bennington, VT 05201
• 

  

  /38

  Est $412,342

  Not Listed For Sale

  1063 Middle Pownal Rd, Bennington, VT 05201

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 1987

  1063 Middle Pownal Rd, Bennington, VT 05201

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Angela Bevin Maple Leaf Real Estate
• 

  

  /39

  $175,000

  • 2 Beds
  • 1 Bath
  • 810 Sq Ft

  220 Gage St, Bennington, VT 05201

  Tired of renting? Discover the charm, convenience, and value of this adorable two-bedroom bungalow - an ideal opportunity for first-time buyers, downsizers, investors, or anyone looking for a cozy second home in town.Tucked away from the hustle and bustle, this historic home is just a short walk from downtown shopping, restaurants, transportation, and everyday conveniences. Inside, you'll

  Justine Curry Maple Leaf Real Estate

  220 Gage St, Bennington, VT 05201
• 

  

  /15

  $96,906

  Sold Jul 11, 2026

  10 Cassie Ln, Bennington, VT 05201

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

  Last Sold Summary

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

  Last Listing Agent Kate Barry EXP Realty

  10 Cassie Ln, Bennington, VT 05201
• 

  

  /40

  Est $196,252

  Not Listed For Sale

  276 Finley Dr, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 1,866 Sq Ft
  • Built 1987

  276 Finley Dr, Bennington, VT 05201

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Lilli West Maple Leaf Real Estate
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  /9

  $269,000

  $26K PRICE DROP

  • 2,206 Sq Ft

  116 S Branch St Unit 118, Bennington, VT 05201

  Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car

  Julie Glover Mahar McCarthy Real Estate

  116 S Branch St Unit 118, Bennington, VT 05201
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  /9

  $65,000

  Sold May 27, 2026

  0 Evergreen Dr, Bennington, VT 05201

  • Land
  • 9.24 Acres
  • $7,035 per Acre

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Justine Curry Maple Leaf Real Estate

  0 Evergreen Dr, Bennington, VT 05201
• 

  

  /40

  Est $566,384

  Not Listed For Sale

  402 Middle Pownal Rd, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 2,706 Sq Ft
  • Built 1880

  402 Middle Pownal Rd, Bennington, VT 05201

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
• 

  

  /13

  $275,000

  $20K PRICE DROP

  • 2,022 Sq Ft

  124 S Branch St, Bennington, VT 05201

  Don’t miss this two-family gem! Each spacious unit features 2 bedrooms, eat-in kitchen, large living room with hardwood floors and tin ceiling throughout, spacious full bathroom, and in-unit laundry hookups - perfect for comfortable living or strong rental potential. The downstairs unit offers a side porch for sitting and both units get to enjoy a charming covered front porch on a side street.

  Julie Glover Mahar McCarthy Real Estate

  124 S Branch St, Bennington, VT 05201
• 

  

  /58

  $299,000

  Sold Jun 01, 2026

  207 Silver St, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1846

  Last Sold Summary

  • $150/SF
  • 143 Days On Market

  Current Estimated Value $303,177

  Last Listing Agent Dan Mason Perrott Realty

  207 Silver St, Bennington, VT 05201
• 

  

  /35

  Est $356,974

  Not Listed For Sale

  1351 Morgan St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,821 Sq Ft
  • Built 1958

  1351 Morgan St, Bennington, VT 05201

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
• 

  

  /50

  $449,900

  • 4 Beds
  • 2.5 Baths
  • 2,396 Sq Ft

  18 Greenview Dr, Bennington, VT 05201

  Come home to the warmth and character of this inviting 4-bedroom, 2.5-bathroom log cabin, tucked into a desirable Bennington neighborhood on .46 acres. From the welcoming front porch to the cozy interior, this home offers the charm of log construction with plenty of space for comfortable everyday living. The living room is the heart of the home, featuring a fireplace and sliding doors that open

  Julie Glover Mahar McCarthy Real Estate

  18 Greenview Dr, Bennington, VT 05201
• 

  

  /42

  $600,000

  Sold Nov 12, 2025

  126 Fox Hill Rd, Bennington, VT 05201

  • 5 Beds
  • 1.5 Baths
  • 2,450 Sq Ft
  • Built 1850

  Last Sold Summary

  • 25% Below List Price
  • $245/SF
  • 148 Days On Market

  Current Estimated Value $643,778

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  126 Fox Hill Rd, Bennington, VT 05201
• 

  

  /37

  Est $277,886

  Not Listed For Sale

  1236 Morgan St, Bennington, VT 05201

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

  1236 Morgan St, Bennington, VT 05201

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
• 

  

  /42

  $180,000

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft

  105 Hicks Ave, Bennington, VT 05201

  Back on the market- This one is for the buyer that sees potential, not perfection! Opportunity awaits at this unique property with an exceptional setting along the Walloomsac River. A true Vermont farmhouse offering three bedrooms and two bathrooms, situated on a flat, park-like lot with mature landscaping, open green space, and beautiful river frontage. The serene setting creates a peaceful

  Angela Bevin Maple Leaf Real Estate

  105 Hicks Ave, Bennington, VT 05201
• 

  

  /35

  $372,000

  Sold May 13, 2026

  303 Prospect St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,463 Sq Ft
  • Built 1949

  Last Sold Summary

  • 1% Above List Price
  • $254/SF
  • 11 Days On Market

  Current Estimated Value $388,416

  Last Listing Agent Angela Bevin Maple Leaf Real Estate

  303 Prospect St, Bennington, VT 05201
• 

  

  /40

  Est $662,966

  Not Listed For Sale

  377 Southshire Dr, Bennington, VT 05201

  • 4 Beds
  • 3.5 Baths
  • 3,183 Sq Ft
  • Built 1988

  377 Southshire Dr, Bennington, VT 05201

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Brandy Lesser
• 

  

  /4

  $349,000

  • 3,637 Sq Ft

  710 Main St, Bennington, VT 05201

  Well-maintained four-unit property ideally located in downtown Bennington. This versatile multi-family offering features just the right amount of yard space for outdoor enjoyment, along with ample off-street parking. The property includes two one-bedroom units, one two-bedroom unit, and one spacious four-bedroom unit, providing a flexible mix of rental options. With a strong rental history and

  Dan Mason Perrott Realty

  710 Main St, Bennington, VT 05201
• 

  

  /18

  $260,000

  Sold Apr 28, 2026

  940 Gage St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,570 Sq Ft
  • Built 1945

  Last Sold Summary

  • 13% Below List Price
  • $166/SF
  • 58 Days On Market

  Current Estimated Value $284,054

  Last Listing Agent Christine Lewis Brattleboro Area Realty

  940 Gage St, Bennington, VT 05201
• 

  

  /40

  Est $612,569

  Not Listed For Sale

  179 Southshire Dr, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 2,336 Sq Ft
  • Built 1984

  179 Southshire Dr, Bennington, VT 05201

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Dan Mason Perrott Realty
• 

  

  /52

  $179,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  130 Morgan St, Bennington, VT 05201

  200 feet of Walloomsac River front .There is a second kitchen for a possible in-law or AB&B. RV parking for those visitors who travel listing to the sounds of the stream for the nomadic visitors. New replacement windows were just done. Bring your imagination and see the possibilities. Showings start 8/18/2026

  Dan Mason Perrott Realty

  130 Morgan St, Bennington, VT 05201
• 

  

  /19

  $220,000

  Sold Jun 23, 2026

  14 Robinson Ave, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,254 Sq Ft
  • Built 1927

  Last Sold Summary

  • $175/SF
  • 309 Days On Market

  Current Estimated Value $236,343

  Last Listing Agent Timothy Corcoran Mahar McCarthy Real Estate

  14 Robinson Ave, Bennington, VT 05201
• 

  

  /35

  Est $339,975

  Not Listed For Sale

  170 Brambley Ln, Bennington, VT 05201

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

  170 Brambley Ln, Bennington, VT 05201

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Matt Waddington Hoffman Real Estate
• 

  

  /52

  $299,000

  $10K PRICE INCREASE

  • 3 Beds
  • 1.5 Baths
  • 1,411 Sq Ft

  262 Union St, Bennington, VT 05201

  Just a short walk to downtown shopping and dining you can move right into this well-maintained and thoughtfully updated 3-bedroom, 2-bath home offering comfortable living spaces, modern conveniences, and plenty of room to spread out both inside and out.The heart of the home is the spacious, updated kitchen featuring a center island, abundant counter top space, and generous cabinetry, and even

  William Paquin Maple Leaf Real Estate

  262 Union St, Bennington, VT 05201
• 

  

  /53

  $505,000

  Sold Aug 21, 2026

  58 Mount Anthony Rd, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 2,715 Sq Ft
  • Built 1928

  Last Sold Summary

  • 27% Below List Price
  • $186/SF
  • 223 Days On Market

  Current Estimated Value $547,599

  Last Listing Agent Monique Geannelis Mahar McCarthy Real Estate

  58 Mount Anthony Rd, Bennington, VT 05201
• 

  

  /37

  Est $331,255

  Not Listed For Sale

  1065 Burgess Rd, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,400 Sq Ft
  • Built 1974

  1065 Burgess Rd, Bennington, VT 05201

  Last Sold Summary

  • 51 Days On Market

  Last Listing Agent Gabrielle Burdge
• 

  

  /26

  $165,000

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  128 Burgess Rd, Bennington, VT 05201

  Affordable homeownership awaits at 128 Burgess Road in Bennington! This compact 2-bedroom, 1-bath home offers approximately 840 square feet of living space with a practical layout and low utility costs. Several recent exterior improvements include brand-new siding, new rear entry stairs and a new electrical meter board in Spring 2026. The home also features vinyl replacement windows, including

  Emily Heyer Hoffman Real Estate

  128 Burgess Rd, Bennington, VT 05201
• 

  

  /30

  $277,000

  Sold Jul 10, 2026

  212 Dewey St, Bennington, VT 05201

  • 2 Beds
  • 2.5 Baths
  • 1,265 Sq Ft
  • Built 1963

  Last Sold Summary

  • 1% Above List Price
  • $219/SF

  Current Estimated Value $273,930

  Last Listing Agent William Paquin Maple Leaf Real Estate

  212 Dewey St, Bennington, VT 05201
• 

  

  /25

  Est $253,358

  Not Listed For Sale

  350 Gore Rd, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,390 Sq Ft
  • Built 1967

  350 Gore Rd, Bennington, VT 05201

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

Showing Results 81 - 120, Page 3 of 18