Bennington, VT Homes

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  /24

  $179,000

  $56K 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

  Melissa Nebelski Real Broker LLC

  340 Pleasant St, Bennington, VT 05201
• 

  

  

  /45

  $405,000

  Sold Apr 20, 2026

  848 Coleville Rd, Bennington, VT 05201

  • 4 Beds
  • 3 Baths
  • 2,030 Sq Ft
  • Built 1980

  Last Sold Summary

  • 10% Below List Price
  • $200/SF
  • 151 Days On Market

  Current Estimated Value $425,659

  Last Listing Agent Beatrice O'Connell Maple Leaf Real Estate

  848 Coleville Rd, Bennington, VT 05201
• 

  

  

  /31

  Est $431,197

  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
• 

  

  

  /40

  $695,000

  • 4 Beds
  • 3.5 Baths
  • 5,769 Sq Ft

  370 Southshire Dr, Bennington, VT 05201

  Welcome to a home that truly has room for it all! Set in a desirable neighborhood on a beautifully landscaped lot, this impressive property offers an incredible amount of living space inside and out. A paved driveway leads to the attached two-car garage, while the backyard feels like your own private retreat with a gorgeous inground pool, spacious patio and beautiful yard perfect for entertaining

  Lilli West Maple Leaf Real Estate

  370 Southshire Dr, Bennington, VT 05201
• 

  

  

  /12

  $325,000

  Sold Jul 20, 2026

  343 Safford St, Bennington, VT 05201

  • 2,476 Sq Ft
  • Built 1900

  Last Sold Summary

  • $131/SF
  • 34 Days On Market

  Last Listing Agent Lori Hurley Four Corner Properties LLC

  343 Safford St, Bennington, VT 05201
• 

  

  /20

  Est $263,580

  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
• 

  

  /24

  $240,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  2200 Chapel Rd, Bennington, VT 05201

  Well maintained and updated 2011 double wide with 3 bedrooms and 2 full bathrooms situated on 1.33 acres in Bennington. Offering new flooring through most of the house and new appliances. Large living room, kitchen and laundry room. Primary bedroom has a private full bath. Nice property and great location.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  2200 Chapel Rd, Bennington, VT 05201
• 

  

  /23

  $388,800

  Sold Jun 10, 2026

  317 Chester Knoll Dr, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 2026

  Last Sold Summary

  • $240/SF

  Last Listing Agent Lilli West Maple Leaf Real Estate

  317 Chester Knoll Dr, Bennington, VT 05201
• 

  

  /58

  Est $304,868

  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
• 

  

  /16

  $395,000

  Pending

  • 4,646 Sq Ft

  307 North St, Bennington, VT 05201

  Exceptional mixed-use opportunity in Bennington’s MU-2 District offering flexibility for investors, owner-occupants, or live/work configurations. Sale includes both 307 North Street and 307.5 North Street, two separate buildings situated on one 0.70-acre parcel with strong visibility and approximately 150 feet of frontage along North Street (VT Route 7). The front building (c. 1840) offers

  Jeffrey Dorman

  307 North St, Bennington, VT 05201
• 

  

  /59

  $408,000

  Sold Jul 27, 2026

  131 Pine Cir, Bennington, VT 05201

  • 4 Beds
  • 3 Baths
  • 2,119 Sq Ft
  • Built 1988

  Last Sold Summary

  • 5% Below List Price
  • $193/SF
  • 48 Days On Market

  Current Estimated Value $413,255

  Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  131 Pine Cir, Bennington, VT 05201
• 

  

  /39

  Est $283,428

  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
• 

  

  /37

  $264,900

  $24K PRICE DROP Under Contract

  • 4 Beds
  • 2 Baths
  • 1,146 Sq Ft

  109 County St, Bennington, VT 05201

  The renovations are done, just move in! Nearly everything is NEW at 109 County Street, including the price! In addition, the seller is offering a $5K credit towards the buyer’s closing costs. This extensively renovated 4BR/2BA home with a fully fenced yard gives you the opportunity to enjoy the benefits of a much newer home without the time, expense, and stress of renovating one yourself.

  Angela Bevin Maple Leaf Real Estate

  109 County St, Bennington, VT 05201
• 

  

  /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 $148,509

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

  755 Main St, Bennington, VT 05201
• 

  

  /38

  Est $251,000

  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
• 

  

  /54

  $460,000

  $35K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,312 Sq Ft

  498 Townline Rd, Bennington, VT 05201

  If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the

  Betty McEnaney Diamond Realty

  498 Townline Rd, Bennington, VT 05201
• 

  

  /40

  $125,000

  Sold May 01, 2026

  130 Lincoln St, Bennington, VT 05201

  • 4 Beds
  • 1 Bath
  • 1,156 Sq Ft
  • Built 1920

  Last Sold Summary

  • 9% Above List Price
  • $108/SF
  • 39 Days On Market

  Current Estimated Value $133,228

  Last Listing Agent Lisa Friedman Great American Dream Realty

  130 Lincoln St, Bennington, VT 05201
• 

  

  /26

  Est $315,426

  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
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  /45

  $255,000

  $40K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  951 Gage St, Bennington, VT 05201

  This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back

  Dan Mason Perrott Realty

  951 Gage St, Bennington, VT 05201
• 

  

  /25

  $98,999

  Sold Jul 27, 2026

  78 Ethans Way, Bennington, VT 05201

  • 2 Beds
  • 2 Baths
  • 825 Sq Ft
  • Built 2024

  Last Sold Summary

  • $120/SF
  • 119 Days On Market

  Last Listing Agent Kate Barry EXP Realty

  78 Ethans Way, Bennington, VT 05201
• 

  

  /51

  Est $241,440

  Not Listed For Sale

  306 Beech St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,876 Sq Ft
  • Built 1989

  306 Beech St, Bennington, VT 05201

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Floyd Amidon Maple Leaf Real Estate
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  /7

  $145,000

  $30K PRICE DROP Pending

  • Land
  • 15.49 Acres
  • $9,361 per Acre

  00 Silk Rd, Bennington, VT 05201

  Fifteen and a half level, mowed acres, suitable for a home build, agriculture, or a small subdivision. Passing over the iconic Silk Road Covered Bridge crossing the Walloomsac River, on the right you'll find this flat, cleared parcel ready for farming or development. With over 500 feet of road frontage, plenty of acreage, and the beautiful river across the street, the possibilities here are

  David White OwnerEntry.com

  00 Silk Rd, Bennington, VT 05201
• 

  

  /37

  $500,000

  Sold Jun 30, 2026

  4 Stonehedge Dr, Bennington, VT 05201

  • 3 Beds
  • 3 Baths
  • 3,182 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $157/SF
  • 20 Days On Market

  Current Estimated Value $508,997

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  4 Stonehedge Dr, Bennington, VT 05201
• 

  

  /32

  Est $317,782

  Not Listed For Sale

  17 Tel Rd, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 2,272 Sq Ft
  • Built 1970

  17 Tel Rd, Bennington, VT 05201

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
• 

  

  /38

  $315,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft

  51 Pageant St, Bennington, VT 05201

  There is something special about a home with character, and this charming 3BR property has it in abundance! Set in an established neighborhood within sight of the Mt. Anthony Country Club, this inviting home offers the warmth and craftsmanship of an earlier era combined with the comforts buyers are looking for. From the moment you arrive, the covered front porch welcomes you home. With generous

  Angela Bevin Maple Leaf Real Estate

  51 Pageant St, Bennington, VT 05201
• 

  

  /26

  $290,000

  Sold Mar 26, 2026

  235 Elm St Unit 3, Bennington, VT 05201

  • 6 Beds
  • 3 Baths
  • 2,640 Sq Ft
  • Built 1880

  Last Sold Summary

  • 2% Below List Price
  • $110/SF
  • 8 Days On Market

  Current Estimated Value $306,722

  Last Listing Agent Erica Hale Ridgeline Real Estate

  235 Elm St Unit 3, Bennington, VT 05201
• 

  

  /40

  Est $256,089

  Not Listed For Sale

  316 Beech St, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 1948

  316 Beech St, Bennington, VT 05201

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Dan Mason Perrott Realty
• 

  /2

  $95,000

  • Land
  • 9.68 Acres
  • $9,814 per Acre

  390 Fairview St, Bennington, VT 05201

  Situated just outside historic Old Bennington and near the Bennington Battle Monument, this property offers the privacy and natural setting of a larger country parcel while remaining convenient to downtown Bennington and area amenities. With approximately 318 feet of road frontage, the wooded property offers plenty of room to create a private homesite surrounded by nature. Much of the preliminary

  Lori Hurley Four Corner Properties LLC

  390 Fairview St, Bennington, VT 05201
• 

  

  /18

  $286,000

  Sold Jun 12, 2026

  124 Albe Dr, Bennington, VT 05201

  • 2 Beds
  • 1 Bath
  • 1,104 Sq Ft
  • Built 2000

  Last Sold Summary

  • 4% Above List Price
  • $259/SF
  • 3 Days On Market

  Current Estimated Value $278,876

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  124 Albe Dr, Bennington, VT 05201
• 

  

  /17

  Est $166,208

  Not Listed For Sale

  224 Beech St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,709 Sq Ft
  • Built 1900

  224 Beech St, Bennington, VT 05201

  Last Sold Summary

  • 103 Days On Market

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

  

  /46

  $259,000

  Under Contract

  • 2 Beds
  • 1 Bath
  • 1,318 Sq Ft

  104 John St, Bennington, VT 05201

  This well-maintained village home located on a dead end rd is move-in ready and filled with inviting features. Set on a desirable corner lot, the property offers an updated bath, spacious covered front and rear porches, and a cozy pellet stove. The kitchen was just updated as well as painted in side and out. The large front entry provides additional usable space, while the one-car insulated and

  Dan Mason Perrott Realty

  104 John St, Bennington, VT 05201
• 

  

  /14

  $20,000

  Sold Oct 30, 2025

  79 Skytop Dr Unit 6, Bennington, VT 05201

  • 1 Bed
  • 1 Bath
  • 561 Sq Ft
  • Built 1950

  Last Sold Summary

  • 27% Below List Price
  • $36/SF
  • 0 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  79 Skytop Dr Unit 6, Bennington, VT 05201
• 

  

  /35

  Est $229,725

  Not Listed For Sale

  218 Beech St, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,680 Sq Ft
  • Built 1890

  218 Beech St, Bennington, VT 05201

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Thomas Martins Maple Leaf Real Estate
• 

  

  /25

  $950,000

  $300K PRICE DROP Under Contract

  • 8,888 Sq Ft

  124 Elm St, Bennington, VT 05201

  A rare opportunity to acquire one of Southern Vermont's most adaptable residential investment properties. Currently known as the South Shire Inn, this landmark Victorian estate offers investors immediate income potential along with exceptional opportunities for future residential or mixed-use redevelopment.The property includes nine guest accommodations, owner's quarters, expansive common

  Marek Kovac TPW Real Estate

  124 Elm St, Bennington, VT 05201
• 

  

  /23

  $259,000

  Sold Jun 04, 2026

  214 Hickory Rd, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 816 Sq Ft
  • Built 1960

  Last Sold Summary

  • $317/SF
  • 2 Days On Market

  Current Estimated Value $245,884

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  214 Hickory Rd, Bennington, VT 05201
• 

  

  /32

  Est $233,081

  Not Listed For Sale

  103 Evergreen Dr, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Built 1945

  103 Evergreen Dr, Bennington, VT 05201

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Gabrielle Burdge
• 

  /2

  $2,190,000

  • Land
  • 1.16 Acres
  • $1,887,931 per Acre

  301 Northside Dr, Bennington, VT 05201

  Prime commercial investment opportunity at 301 Northside Drive, Bennington. This 1.16-acre corner lot offers exceptional visibility on a heavily traveled road, making it well-suited for high-exposure commercial uses. Commercial zoning allows for a range of development or redevelopment options. Strategically located near major highways, providing strong regional access and long-term demand

  Paul Carroccio TPW Real Estate

  301 Northside Dr, Bennington, VT 05201
• 

  

  /54

  $80,000

  Sold Dec 09, 2025

  889 Overlea Rd, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 1976

  Last Sold Summary

  • 5% Below List Price
  • $87/SF
  • 4 Days On Market

  Last Listing Agent Catherine Cairns Maple Leaf Real Estate

  889 Overlea Rd, Bennington, VT 05201
• 

  

  /40

  Est $258,732

  Not Listed For Sale

  313 Beech St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,150 Sq Ft
  • Built 1960

  313 Beech St, Bennington, VT 05201

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
• 

  

  /60

  $675,000

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,614 Sq Ft

  515 Quarry Rd, Bennington, VT 05201

  Peaceful, private, and completely surrounded by nature, this beautifully renovated contemporary home offers the perfect mountain retreat nestled on 14.7 acres on the side of Mt. Anthony with seasonal views and unmatched tranquility. Enjoy direct access to miles of hiking trails, abundant wildlife, and the rare protection of no future development permitted above this elevation, preserving the

  Vicki Wilson Maple Leaf Real Estate

  515 Quarry Rd, Bennington, VT 05201

Showing Results 121 - 160, Page 4 of 18