Bennington County, VT Homes

• 

  

  

  /34

  $275,000

  Sold May 22, 2026

  1808 East Rd, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1977

  Last Sold Summary

  • 6% Above List Price
  • $260/SF
  • 7 Days On Market

  Current Estimated Value $285,192

  Last Listing Agent Abi Gregorio

  1808 East Rd, Bennington, VT 05201
• 

  

  

  /40

  Est $108,672

  Not Listed For Sale

  51 Chiselville Rd, Arlington, VT 05250

  • 2 Beds
  • 2 Baths
  • 540 Sq Ft
  • Built 1820

  51 Chiselville Rd, Arlington, VT 05250

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Nicholas Charest Maple Leaf Real Estate
• 

  

  

  /55

  $1,475,000

  • 5 Beds
  • 4 Baths
  • 4,491 Sq Ft

  866 E Manchester Rd, Manchester Center, VT 05255

  If you are looking for a property with both mountain and water views, this exceptional five-bedroom Manchester home is a must-see.Set on a remarkable lot featuring breathtaking vistas and approximately 400 feet of frontage along Bromley Brook, this home offers a rare combination of privacy, natural beauty, and convenience. Located just minutes from the center of Manchester and near the

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  866 E Manchester Rd, Manchester Center, VT 05255
• 

  

  /2

  $1,700,000

  Sold Jul 31, 2026

  5491 Vt Route 315, Rupert, VT 05776

  • 5 Beds
  • 4.5 Baths
  • 3,218 Sq Ft
  • Built 1905

  Last Sold Summary

  • 19% Below List Price
  • $528/SF
  • 339 Days On Market

  Last Listing Agent Annette Gallo Real Broker LLC

  5491 Vt Route 315, Rupert, VT 05776
• 

  

  

  /18

  Est $544,944

  Not Listed For Sale

  55 Wildflower Ln, Arlington, VT 05250

  • 3 Beds
  • 2.5 Baths
  • 2,514 Sq Ft
  • Built 1997

  55 Wildflower Ln, Arlington, VT 05250

  Last Sold Summary

  • 46 Days On Market

  Last Listing Agent Sean Dillon Real Broker LLC
• 

  

  /10

  $150,000

  • Land
  • 4 Acres
  • $37,500 per Acre

  0 Rocky Ln Unit 5082777, Dorset, VT 05253

  'THE GROUND BENEATH AN APRIL SNOWSTORM IS NOT DORMANT... IT IS AWAKENING!".... Come discover the perfect opportunity to craft the home of your dreams!! With Spring ready to bloom, this very special lot is vibrant and quite ready for your vision!Fully permitted for a five bedroom residence, this property combines privacy, natural beauty and convenience!Imagine waking up to serene views,

  Sunny Breen Josiah Allen Real Estate, Inc.

  0 Rocky Ln Unit 5082777, Dorset, VT 05253
• 

  

  /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 $150,206

  Last Listing Agent Angela Bevin Maple Leaf Real Estate

  432 South St Unit C6, Bennington, VT 05201
• 

  

  /37

  Est $482,191

  Not Listed For Sale

  127 Flynn Hollow Rd, Sunderland, VT 05250

  • 3 Beds
  • 1.5 Baths
  • 1,718 Sq Ft
  • Built 1989

  127 Flynn Hollow Rd, Sunderland, VT 05250

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Tatsiana Clark Four Seasons Sotheby's Int'l Realty
• 

  

  /37

  $489,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,830 Sq Ft

  292 Forest Mountain Rd, Peru, VT 05152

  Imagine turning off the main road as the canopy thickens, the drone of highway traffic fading into the quiet rustle of wind through northern hardwoods. Up on a gentle knoll surrounded by over two wooded acres, 292 Forest Mountain Road feels less like a house and more like a breath of fresh air.Morning here starts slowly. Coffee brews while sunlight filters through the trees, casting soft

  Robin Apps Four Seasons Sotheby's Int'l Realty

  292 Forest Mountain Rd, Peru, VT 05152
• 

  

  /34

  $684,000

  Sold Jun 22, 2026

  2744 Danby Mountain Rd, Dorset, VT 05251

  • 3 Beds
  • 2.5 Baths
  • 4,683 Sq Ft
  • Built 1985

  Last Sold Summary

  • 2% Below List Price
  • $146/SF
  • 1 Day On Market

  Last Listing Agent Andie Fusco Four Seasons Sotheby's Int'l Realty

  2744 Danby Mountain Rd, Dorset, VT 05251
• 

  

  /34

  Est $259,304

  Not Listed For Sale

  925 South Rd, East Arlington, VT 05252

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1972

  925 South Rd, East Arlington, VT 05252

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
• 

  

  /6

  $69,900

  Pending

  • 2 Beds
  • 1 Bath
  • 1,352 Sq Ft

  32 French Hill Rd, Pownal, VT 05261

  Subject property currently has two buildings on the property. One is a ranch style home the other is a shed. Property has just under an acre of land with power, and town sewer at the street. Do not entry property without your buyer's agent with you. This property is part of a First Look program. It allows owner occupant buyers to have their offers negotiated on day 8 of being listed. Owner

  April Shepard Twin State Realty LLC

  32 French Hill Rd, Pownal, VT 05261
• 

  

  /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 $662,890

  Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  55 Monument Ave, Bennington, VT 05201
• 

  

  /34

  Est $520,762

  Not Listed For Sale

  3600 North Rd, Arlington, VT 05250

  • 3 Beds
  • 2.5 Baths
  • 1,891 Sq Ft
  • Built 2004

  3600 North Rd, Arlington, VT 05250

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Matt Waddington Hoffman Real Estate
• 

  

  /20

  $549,000

  $146K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  27 Owls Head Hill Ln, Dorset, VT 05251

  Charming Raised Ranch on 2 Acres – Dorset, VTWelcome to your new home in the heart of Dorset! Nestled on a beautifully landscaped 2-acre corner lot, this inviting raised ranch offers privacy, comfort, and versatile living space.3 Bedrooms | 2 Full Baths | 2-Car Attached GarageStep inside to find a bright living room that flows seamlessly into the eat-in kitchen, perfect for everyday

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  27 Owls Head Hill Ln, Dorset, VT 05251
• 

  

  /40

  $527,700

  Sold Jun 30, 2026

  1138 Barber Pond Rd, Pownal, VT 05261

  • 3 Beds
  • 2 Baths
  • 2,732 Sq Ft
  • Built 1993

  Last Sold Summary

  • 1% Above List Price
  • $193/SF
  • 5 Days On Market

  Current Estimated Value $521,267

  Last Listing Agent Lilli West Maple Leaf Real Estate

  1138 Barber Pond Rd, Pownal, VT 05261
• 

  

  /32

  Est $479,050

  Not Listed For Sale

  2128 North Rd, Arlington, VT 05250

  • 3 Beds
  • 2 Baths
  • 1,552 Sq Ft
  • Built 1987

  2128 North Rd, Arlington, VT 05250

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Lisa Sullivan Four Seasons Sotheby's Int'l Realty
• 

  

  /13

  $975,000

  • Land
  • 69.3 Acres
  • $14,069 per Acre

  437 Pratt Rd, Pownal, VT 05261

  Nearly 70 acres of breathtaking Vermont land where the possibilities are as impressive as the views. From the moment you arrive, this property has a way of stopping you in your tracks, with expansive mountain and countryside views that seem to change from every vantage point.Once home to a working farm, the property still features a barn and silo, along with a drilled well from the former

  Lilli West Maple Leaf Real Estate

  437 Pratt Rd, Pownal, VT 05261
• 

  

  /6

  $262,500

  Sold Sep 30, 2025

  X Mount Aeolus Rd, Manchester, VT 05255

  • Land
  • 8.32 Acres
  • $31,550 per Acre

  Last Sold Summary

  • 33% Below List Price
  • 88 Days On Market

  Last Listing Agent Carol O`Connor Four Seasons Sotheby's Int'l Realty

  X Mount Aeolus Rd, Manchester, VT 05255
• 

  

  /38

  Est $313,615

  Not Listed For Sale

  1469 Sunderland Hill Rd, Arlington, VT 05250

  • 3 Beds
  • 1.5 Baths
  • 1,268 Sq Ft
  • Built 1958

  1469 Sunderland Hill Rd, Arlington, VT 05250

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
• 

  

  /44

  $189,900

  Pending

  • 3 Beds
  • 1 Bath
  • 1,206 Sq Ft

  232 Depot St, Bennington, VT 05201

  Charming in-town 3-bedroom, 1-bath home situated on a low-maintenance 0.09-acre lot. Enjoy a private, fully fenced backyard with views of Mt Anthony, which is perfect for relaxing, entertaining, or pets. Shared driveway with off-street parking. Conveniently located within walking distance to shopping, restaurants, parks, and local amenities. This home offers the perfect blend of comfort and

  Floyd Amidon Maple Leaf Real Estate

  232 Depot 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 $131,516

  Last Listing Agent Erika Floriani Hoffman Real Estate

  45 Shady Ln, Bennington, VT 05201
• 

  

  /26

  Est $406,304

  Not Listed For Sale

  131 Mckee Rd, Arlington, VT 05250

  • 3 Beds
  • 3 Baths
  • 1,732 Sq Ft
  • Built 1985

  131 Mckee Rd, Arlington, VT 05250

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Tatsiana Clark Four Seasons Sotheby's Int'l Realty
• 

  

  /38

  $1,175,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 3,094 Sq Ft

  88 Windward S, Dorset, VT 05251

  Beautifully maintained contemporary home on 3.62 private acres with elevated westerly views of Mt. Equinox and spectacular sunsets. Designed by renown architect Deborah Berke, Dean of the Yale School of Architecture, this light-filled home offers the ease of main-level living with a first-floor primary suite, laundry, bright office, den with custom built-ins, and spacious living room with vaulted

  David Halligan Four Seasons Sotheby's Int'l Realty

  88 Windward S, Dorset, VT 05251
• 

  

  /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 $503,453

  Not Listed For Sale

  466 Laver Rd, Arlington, VT 05250

  • 5 Beds
  • 2.5 Baths
  • 2,560 Sq Ft
  • Built 2006

  466 Laver Rd, Arlington, VT 05250

  Last Sold Summary

  • 369 Days On Market

  Last Listing Agent Lilli West Maple Leaf Real Estate
• 

  

  /29

  $639,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,832 Sq Ft

  197 Bromley Brook Rd, Manchester Center, VT 05255

  Welcome to this inviting one level Manchester Vermont home, perfect for easy living and year round enjoyment and minutes from Bromley, Magic, and Stratton ski areas. A spacious deck off the kitchen welcomes you to the home and offers a wonderful spot to enjoy the morning sun and take in the surrounding mountain views.Inside, the bright, open kitchen features a wall of windows with lovely

  Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  197 Bromley Brook Rd, Manchester Center, VT 05255
• 

  

  /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 $391,468

  Not Listed For Sale

  106 Millbrook Rd, Arlington, VT 05250

  • 2 Beds
  • 2 Baths
  • 2,248 Sq Ft
  • Built 1984

  106 Millbrook Rd, Arlington, VT 05250

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Margretta Fischer Wohler Realty Group
• 

  

  /22

  $435,000

  $64K PRICE DROP Pending

  • 3,648 Sq Ft

  938 Vt Route 7a, Shaftsbury, VT 05262

  Strong income potential and a versatile unit mix make this 4-unit property an outstanding investment opportunity. The building features two 2-bedroom, 1-bath units, a spacious 3-bedroom, 1-bath unit, and a 1-bedroom, 1-bath apartment, appealing to a wide range of tenants. This well-positioned property offers dependable rental income and the flexibility that investors seek. Whether you're adding

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  938 Vt Route 7a, Shaftsbury, VT 05262
• 

  

  /4

  $225,000

  Sold Dec 19, 2025

  00 Margeaux Ln, Stratton, VT 05155

  • Land
  • 1.99 Acres
  • $113,065 per Acre

  Last Sold Summary

  • 189 Days On Market

  Last Listing Agent Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  00 Margeaux Ln, Stratton, VT 05155
• 

  

  /24

  Est $318,717

  Not Listed For Sale

  408 Dunlap Farm Rd, Arlington, VT 05250

  • 2 Beds
  • 1 Bath
  • 988 Sq Ft
  • Built 1984

  408 Dunlap Farm Rd, Arlington, VT 05250

  Last Sold Summary

  • 88 Days On Market

  Last Listing Agent Andrea Kaplan Four Seasons Sotheby's Int'l Realty
• 

  

  /53

  $1,695,000

  • 3 Beds
  • 2.5 Baths
  • 4,120 Sq Ft

  1944 Monument Ave, Bennington, VT 05201

  Set on 5.63 beautiful acres in one of Bennington's most desirable locations, this exceptional 1880 historic home has been thoughtfully renovated inside and out, blending timeless character with sophisticated modern amenities. The property includes approximately 3,200 square feet in the main residence, an attached two-car garage with a second kitchen, and a separate 1,000-square-foot one-bedroom

  Kelley Mccarthy Mahar McCarthy Real Estate

  1944 Monument Ave, 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
• 

  

  /38

  Est $404,383

  Not Listed For Sale

  366 Clough Rd, Stamford, VT 05352

  • 4 Beds
  • 2 Baths
  • 1,809 Sq Ft
  • Built 1964

  366 Clough Rd, Stamford, VT 05352

  Last Sold Summary

  • 59 Days On Market

  Last Listing Agent Debra Burchard Lamacchia Realty, Inc. - North Adams
• 

  

  /29

  $85,000

  • Land
  • 10 Acres
  • $8,500 per Acre

  0 Ladd Rd Unit 5111157, Pownal, VT 05261

  Ten wooded acres in Pownal offering a versatile setting for a future homesite, recreational retreat, or potential subdivision, subject to all applicable approvals. The property extends between South Mann Hill Road and Ladd Road, with road frontage on both and an existing rudimentary driveway/trail entrance from South Mann Hill Road. Follow the old woods road into the property to discover open

  Jenifer Prouty Hoffman Hoffman Real Estate

  0 Ladd Rd Unit 5111157, Pownal, VT 05261
• 

  

  /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
• 

  

  /33

  Est $197,755

  Not Listed For Sale

  133 Tatro Rd, Stamford, VT 05352

  • 2 Beds
  • 1 Bath
  • 972 Sq Ft
  • Built 1995

  133 Tatro Rd, Stamford, VT 05352

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Monique White Deerfield Valley Real Estate
• 

  

  /36

  $259,000

  Under Contract

  • 4 Beds
  • 2 Baths
  • 1,768 Sq Ft

  549 Houran Rd, Bennington, VT 05201

  Well maintained and thoughtfully updated, this 4-bedroom, 2-bath home offers the ease of single-level living on a beautiful level one-acre lot in Bennington's desirable west end. Enjoy stunning mountain views from the spacious back deck or sip your morning coffee on the covered front porch. Inside, you'll find an updated kitchen, refreshed bathrooms, a cozy fireplace, central air conditioning, a

  Abi Gregorio

  549 Houran Rd, Bennington, VT 05201
• 

  

  /8

  $9,999

  Sold Jul 30, 2026

  0 Alpendorf Ave, Readsboro, VT 05350

  • Land
  • 1.2 Acres
  • $8,332 per Acre

  Last Sold Summary

  • 38% Below List Price
  • 289 Days On Market

  Last Listing Agent David White OwnerEntry.com

  0 Alpendorf Ave, Readsboro, VT 05350

Showing Results 241 - 280, Page 7 of 18