Bennington, VT Homes

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  /17

  $140,500

  Sold Feb 24, 2026

  432 South St Unit C6, Bennington, VT 05201

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

  Last Sold Summary

  • 9% Below List Price
  • $165/SF
  • 181 Days On Market

  Current Estimated Value $147,521

  Last Listing Agent Angela Bevin Maple Leaf Real Estate

  432 South St Unit C6, 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
• 

  

  

  /52

  $230,000

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  113 Main St, Bennington, VT 05201

  Charming downtown family home with modern upgrades and timeless appeal. This beautifully updated 3-bedroom home is perfectly situated on a corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, the home features a recently added first-floor primary bedroom and a new mudroom entry.Step inside to find gleaming newly upgraded flooring, a warm and inviting

  Lindsey Martin Maple Leaf Real Estate

  113 Main St, Bennington, VT 05201
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  /50

  $640,000

  Sold Dec 22, 2025

  55 Monument Ave, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 2,675 Sq Ft
  • Built 1787

  Last Sold Summary

  • 2% Below List Price
  • $239/SF
  • 14 Days On Market

  Current Estimated Value $658,252

  Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  55 Monument Ave, Bennington, VT 05201
• 

  

  

  /40

  Est $603,710

  Not Listed For Sale

  88 Southshire Dr, Bennington, VT 05201

  • 3 Beds
  • 3.5 Baths
  • 2,952 Sq Ft
  • Built 1988

  88 Southshire Dr, Bennington, VT 05201

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
• 

  

  /53

  $205,000

  • 3 Beds
  • 1.5 Baths
  • 1,632 Sq Ft

  305 Weeks St, Bennington, VT 05201

  Experience refined living in this beautifully appointed tri-level townhouse-style condominium, ideally situated just moments from downtown, the hospital, shopping, and dining. Rich in vintage character while thoughtfully updated for modern living, this exceptional residence showcases elegant quartz and butcher block countertops, a designer tile backsplash, and striking marble flooring that create

  Lindsey Martin Maple Leaf Real Estate

  305 Weeks St, Bennington, VT 05201
• 

  

  /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

  Current Estimated Value $129,535

  Last Listing Agent Erika Floriani Hoffman Real Estate

  45 Shady Ln, Bennington, VT 05201
• 

  

  /40

  Est $665,925

  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
• 

  

  /39

  $250,000

  $10K PRICE DROP

  • 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
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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

  Current Estimated Value $239,907

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  110 S Branch St, Bennington, VT 05201
• 

  

  /40

  Est $617,616

  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
• 

  

  /27

  $179,000

  $20K PRICE DROP

  • 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
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  /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
• 

  

  /37

  Est $327,983

  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
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  /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
• 

  

  /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 $339,982

  Last Listing Agent Matt Waddington Hoffman Real Estate

  170 Brambley Ln, Bennington, VT 05201
• 

  

  /25

  Est $251,102

  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
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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
• 

  

  /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 $267,333

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

  1488 Morgan St, Bennington, VT 05201
• 

  

  /31

  Est $432,201

  Not Listed For Sale

  543 Gore Rd, Bennington, VT 05201

  • 3 Beds
  • 3 Baths
  • 1,963 Sq Ft
  • Built 1990

  543 Gore Rd, Bennington, VT 05201

  Last Sold Summary

  • 87 Days On Market

  Last Listing Agent Brenda Jones KW Vermont - Brenda Jones Real Estate Group
• 

  

  /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
• 

  

  /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 $266,655

  Last Listing Agent Lilli West Maple Leaf Real Estate

  935 Gage St, Bennington, VT 05201
• 

  

  /40

  Est $288,668

  Not Listed For Sale

  25 Center St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft
  • Built 1990

  25 Center St, Bennington, VT 05201

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Lilli West Maple Leaf Real Estate
• 

  

  /42

  $180,000

  Under Contract

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

  105 Hicks Ave, Bennington, VT 05201

  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 atmosphere rarely found in properties with such versatile potential. A large barn

  Angela Bevin Maple Leaf Real Estate

  105 Hicks Ave, Bennington, VT 05201
• 

  

  /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 $251,641

  Last Listing Agent Thomas Martins Maple Leaf Real Estate

  304 North St Unit 6, Bennington, VT 05201
• 

  

  /20

  Est $272,033

  Not Listed For Sale

  42 Center St, Bennington, VT 05201

  • 2 Beds
  • 2 Baths
  • 1,080 Sq Ft
  • Built 1986

  42 Center St, Bennington, VT 05201

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Faith Rhodes Maple Leaf Real Estate
• 

  

  /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
• 

  

  /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
• 

  

  /58

  Est $301,232

  Not Listed For Sale

  44 Harbour Rd, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,903 Sq Ft
  • Built 1973

  44 Harbour Rd, Bennington, VT 05201

  Last Sold Summary

  • 49 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
• 

  

  /52

  $179,000

  Coming Soon

  • 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
• 

  

  /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
• 

  

  /39

  Est $279,990

  Not Listed For Sale

  30 Harbour Rd, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,608 Sq Ft
  • Built 1971

  30 Harbour Rd, Bennington, VT 05201

  Last Sold Summary

  • 69 Days On Market

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy 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
• 

  

  /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 $304,490

  Last Listing Agent Dan Mason Perrott Realty

  207 Silver St, Bennington, VT 05201
• 

  

  /38

  Est $249,857

  Not Listed For Sale

  5 Tel Rd, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1969

  5 Tel Rd, Bennington, VT 05201

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
• 

  

  /48

  $230,000

  Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,128 Sq Ft

  104 Short St, Bennington, VT 05201

  Blending vintage charm with modern updates, this beautifully refreshed 3-bedroom, 2-bath home offers comfortable in-town living close to local amenities. Recent improvements include a newer roof installed just three years ago and new flooring throughout, creating a fresh and inviting atmosphere. Other additions include new kitchen appliances, furnace, and heat pump hybrid water heater, making the

  Lindsey Martin Maple Leaf Real Estate

  104 Short St, 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 $625,245

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  126 Fox Hill Rd, Bennington, VT 05201
• 

  

  /26

  Est $314,133

  Not Listed For Sale

  1 Tel Cir, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft
  • Built 1972

  1 Tel Cir, Bennington, VT 05201

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Margretta Fischer Wohler Realty Group
• 

  

  /24

  $215,000

  $20K PRICE DROP

  • 1,300 Sq Ft

  340 Pleasant St, Bennington, VT 05201

  Downtown Bennington duplex offering an excellent opportunity for first-time homebuyers, owner-occupants, or investors. The first-floor unit has been completely renovated with a new kitchen, updated bathroom, and new flooring throughout. Recent improvements include a repointed foundation, fully completed siding, a new roof, and a gravel driveway. Live in one unit and help offset your mortgage with

  Melissa Nebelski Real Broker LLC

  340 Pleasant St, Bennington, VT 05201
• 

  

  /20

  $89,499

  Sold Sep 24, 2025

  72 Ethans Way, Bennington, VT 05201

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft
  • Built 2024

  Last Sold Summary

  • 10% Below List Price
  • $108/SF
  • 120 Days On Market

  Last Listing Agent Kate Barry EXP Realty

  72 Ethans Way, Bennington, VT 05201

Showing Results 81 - 120, Page 3 of 18