Bennington County, VT Homes

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  /43

  $180,367

  Sold Nov 06, 2025

  634 Wiley Mountain Dr, Readsboro, VT 05350

  • 1 Bed
  • 400 Sq Ft
  • Built 1986

  Last Sold Summary

  • 3% Below List Price
  • $451/SF
  • 40 Days On Market

  Current Estimated Value $185,409

  Last Listing Agent Cyd Scott Cohn & Company

  634 Wiley Mountain Dr, Readsboro, VT 05350
• 

  

  

  /41

  Est $581,712

  Not Listed For Sale

  1565 E Manchester Rd, Manchester Center, VT 05255

  • 3 Beds
  • 2 Baths
  • 2,088 Sq Ft
  • Built 1967

  1565 E Manchester Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Jessica Citera Cummings & Co
• 

  

  

  /43

  $439,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 1,868 Sq Ft

  96 Twitchell Hill Rd, Shaftsbury, VT 05262

  Some homes simply have a way of making you slow down. Built in 1863, the original Twitchell Farmhouse is one of them. Rich in history and craftsmanship, this beautifully maintained four-bedroom, 2.5-bath home offers the warmth and authenticity that only a true Vermont farmhouse can provide.Original hardwood floors, handcrafted woodwork by a master carpenter, and thoughtful updates create

  Daire Gibney Barrett and Valley Associates Inc.

  96 Twitchell Hill Rd, Shaftsbury, VT 05262
• 

  

  

  /32

  $275,000

  Sold Aug 28, 2026

  110 State Line Dr, Pownal, VT 05261

  • 3 Beds
  • 1.5 Baths
  • 1,392 Sq Ft
  • Built 1965

  Last Sold Summary

  • 4% Above List Price
  • $198/SF
  • 9 Days On Market

  Current Estimated Value $281,174

  Last Listing Agent Abi Gregorio

  110 State Line Dr, Pownal, VT 05261
• 

  

  

  /45

  Est $745,652

  Not Listed For Sale

  327 Deer Meadow Rd, Manchester Center, VT 05255

  • 3 Beds
  • 2.5 Baths
  • 2,432 Sq Ft
  • Built 1971

  327 Deer Meadow Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.
• 

  /2

  $99,900

  Pending

  • Land
  • 2.6 Acres
  • $38,423 per Acre

  0 Kesick Swamp Rd, Sunderland, VT 05250

  Terrific 2.6 acre building lot in Sunderland. Located at the end of Kesick Swamp Road. Private and almost ready to go. Some site work has been done and a septic design for a 2 bedroom home has been completed, just needs permitting.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  0 Kesick Swamp Rd, Sunderland, VT 05250
• 

  

  /49

  $2,200,000

  Sold Jul 15, 2026

  7537 Main St, Manchester Center, VT 05255

  • 4 Beds
  • 3.5 Baths
  • 4,265 Sq Ft
  • Built 2022

  Last Sold Summary

  • $516/SF
  • 5 Days On Market

  Current Estimated Value $2,147,821

  Last Listing Agent Elena Atwill Four Seasons Sotheby's Int'l Realty

  7537 Main St, Manchester Center, VT 05255
• 

  

  /40

  Not Listed For Sale

  658 Finbars Forest Rd, Manchester Center, VT 05255

  • 5 Beds
  • 4 Baths
  • 2,602 Sq Ft
  • Built 1989

  658 Finbars Forest Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Lindsey Pinder Josiah Allen Real Estate, Inc.
• 

  

  /23

  $329,900

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,030 Sq Ft

  773 Oberdorf Rd, Readsboro, VT 05350

  Discover cozy mountain living in this charming Alpenwald chalet, where rustic character meets thoughtful modern updates. Nestled among the trees, this inviting retreat offers a bright, open floor plan filled with natural light from expansive windows and sliding glass doors. Recently remodeled, the kitchen and both full bathrooms bring a fresh, updated feel, while a comfortable bar area adds the

  Sean Taylor Moresi Real Estate Partners

  773 Oberdorf Rd, Readsboro, VT 05350
• 

  

  /60

  $285,000

  Sold Feb 18, 2026

  150 Fillmore St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 2000

  Last Sold Summary

  • 4% Above List Price
  • $203/SF
  • 54 Days On Market

  Last Listing Agent Justine Curry Maple Leaf Real Estate

  150 Fillmore St, Bennington, VT 05201
• 

  

  /32

  Est $1,003,721

  Not Listed For Sale

  1145 Powderhorn Rd, Manchester Center, VT 05255

  • 4 Beds
  • 3.5 Baths
  • 3,728 Sq Ft
  • Built 1983

  1145 Powderhorn Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 109 Days On Market

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

  

  /16

  $204,000

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft

  112 Outwater Rd, Shaftsbury, VT 05262

  Enjoy the effortless flow and convenience of single-level living in this 3-bedroom, 2-bathroom manufactured home. Thoughtfully set back above the road on a private, expansive 1+ acre lot. A long driveway leads to the property, offering enhanced privacy and curb appeal. Inside, the inviting open floor plan is anchored by an expansive kitchen with abundant storage and a bright dining nook that

  Michaela Lawyer Brattleboro Area Realty

  112 Outwater Rd, Shaftsbury, VT 05262
• 

  

  /40

  $665,000

  Sold May 13, 2026

  134 Monument Ave, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 2,868 Sq Ft
  • Built 1927

  Last Sold Summary

  • 4% Below List Price
  • $232/SF
  • 178 Days On Market

  Current Estimated Value $666,652

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  134 Monument Ave, Bennington, VT 05201
• 

  

  /31

  Est $523,352

  Not Listed For Sale

  109 Hillcrest Rd, Manchester Center, VT 05255

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1969

  109 Hillcrest Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent David Halligan Four Seasons Sotheby's Int'l Realty
• 

  

  /15

  $125,000

  • Land
  • 1.18 Acres
  • $105,932 per Acre

  510 Center St, Pownal, VT 05261

  Discover the potential of this scenic 1.18 acre parcel situated on a quiet street directly across from the town offices. Offering beautiful views and the convenience of town sewer, this property presents an excellent opportunity to build the home you've been dreaming of. Whether you're planning a year-round residence or a peaceful retreat, the generous lot provides plenty of space to create your

  Angela Bevin Maple Leaf Real Estate

  510 Center St, Pownal, VT 05261
• 

  /2

  $400,000

  Sold Mar 09, 2026

  97 N Branch Rd, Winhall, VT 05155

  • Land
  • 1.18 Acres
  • $338,983 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 29 Days On Market

  Last Listing Agent John Sikes Stratton Real Estate

  97 N Branch Rd, Winhall, VT 05155
• 

  

  /35

  Est $662,547

  Not Listed For Sale

  602 Barnumville Rd, Manchester Center, VT 05255

  • 3 Beds
  • 2 Baths
  • 1,907 Sq Ft
  • Built 1960

  602 Barnumville Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Katherine Zilkha Four Seasons Sotheby's Int'l Realty
• 

  

  /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
• 

  

  /40

  $185,000

  Sold May 12, 2026

  317 Pleasant St, Bennington, VT 05201

  • 5 Beds
  • 2 Baths
  • 2,201 Sq Ft
  • Built 1900

  Last Sold Summary

  • 14% Below List Price
  • $84/SF
  • 125 Days On Market

  Current Estimated Value $191,120

  Last Listing Agent Michael Gilman 3GEN Real Estate Inc

  317 Pleasant St, Bennington, VT 05201
• 

  

  /31

  Est $550,450

  Not Listed For Sale

  373 Highland Ave, Manchester Center, VT 05255

  • 4 Beds
  • 1.5 Baths
  • 1,830 Sq Ft
  • Built 1905

  373 Highland Ave, Manchester Center, VT 05255

  Last Sold Summary

  • 5 Days On Market

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

  

  /16

  $60,000

  Under Contract

  • Land
  • 5 Acres
  • $12,000 per Acre

  0 Sunderland Hill Rd, West Arlingtn, VT 05250

  Vacant 5.0 acre land lot on Sunderland Hill Road, featuring good road frontage - 826 ft, heavily wooded with mature trees, and sloped topography.Additionally, there has been professional engineering work completed - soils testing and mapping that indicate an in-ground septic system could be added. There will be considerable site work required. There is not a septic design or state waste

  David Halligan Four Seasons Sotheby's Int'l Realty

  0 Sunderland Hill Rd, West Arlingtn, VT 05250
• 

  

  /56

  $405,000

  Sold Dec 17, 2025

  130 Clark Rd, Pawlet, VT 05761

  • 4 Beds
  • 2 Baths
  • 2,120 Sq Ft
  • Built 1790

  Last Sold Summary

  • 3% Above List Price
  • $191/SF
  • 8 Days On Market

  Current Estimated Value $379,863

  Last Listing Agent Scott McChesney McChesney RE, Inc.

  130 Clark Rd, Pawlet, VT 05761
• 

  

  /17

  Est $325,854

  Not Listed For Sale

  1581 E Manchester Rd, Manchester Center, VT 05255

  • 2 Beds
  • 1 Bath
  • 952 Sq Ft
  • Built 1952

  1581 E Manchester Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Patti Trudel RE/MAX Four Seasons
• 

  

  /40

  $3,995,000

  $3M PRICE DROP Pending

  • 5 Beds
  • 5.5 Baths
  • 6,500 Sq Ft

  515 W Fields Rd, Manchester, VT 05254

  Enduring values expressed in stone and wood! VERMONT CRAFTMANSHIP...A WORK OF ART!! Offering a private haven just minutes from downtown, in the heart of Manchester Village, nestled in the foothills of Equinox Mtn. is this rareand exceptional 5-bedroom, 6-bathroom home....The creative designof Architect Ramsey Gourd and Master Builder Mark Breen, well knownas two of Southern Vermont's

  Sunny Breen Josiah Allen Real Estate, Inc.

  515 W Fields Rd, Manchester, VT 05254
• 

  

  /44

  $340,000

  Sold Jan 23, 2026

  989 Carpenter Hill Rd, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,660 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Below List Price
  • $205/SF
  • 85 Days On Market

  Current Estimated Value $353,127

  Last Listing Agent Angela Bevin Maple Leaf Real Estate

  989 Carpenter Hill Rd, Bennington, VT 05201
• 

  

  /28

  Est $266,974

  Not Listed For Sale

  433 Squires Rd, Manchester Center, VT 05255

  • 2 Beds
  • 1 Bath
  • 1,142 Sq Ft
  • Built 1974

  433 Squires Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Linda Benoit Highland Realty
• 

  

  /39

  $975,000

  • 4 Beds
  • 3 Baths
  • 3,548 Sq Ft

  259 Beechnut Dr, Peru, VT 05152

  Beautiful Log Home on 4.23 Private Acres in PeruTucked away at the end of a quiet dead-end road, this beautiful log home offers privacy, space, and an ideal Vermont setting on 4.23 acres. Expansive views become even more impressive as the seasons change, and the home’s open floor plan is perfectly designed for entertaining family and friends.The main living level features a stunning

  Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

  259 Beechnut Dr, Peru, VT 05152
• 

  

  /60

  $534,000

  Sold Nov 24, 2025

  272 Oak Hill Rd, Shaftsbury, VT 05262

  • 3 Beds
  • 2.5 Baths
  • 3,637 Sq Ft
  • Built 2001

  Last Sold Summary

  • 24% Below List Price
  • $147/SF
  • 111 Days On Market

  Current Estimated Value $579,151

  Last Listing Agent Faith Rhodes Maple Leaf Real Estate

  272 Oak Hill Rd, Shaftsbury, VT 05262
• 

  

  /40

  Est $1,643,358

  Not Listed For Sale

  2894 West Rd, Manchester Center, VT 05255

  • 3 Beds
  • 6 Baths
  • 3,556 Sq Ft
  • Built 1970

  2894 West Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Alexandra Crowley Four Seasons Sotheby's Int'l Realty
• 

  

  /31

  $185,000

  • 3 Beds
  • 1 Bath
  • 1,590 Sq Ft

  176 Glen Ave, Readsboro, VT 05350

  This classic, 1,590-square-foot, 3 bedroom, 1 bathroom home sits on a spacious 1.9-acre lot with plenty of potential, conveniently just 0.2 miles from Main Street in Readsboro. Located on a paved road, the house was built in 1880 and combines historic character with several important recent updates, including a new boiler, fresh interior paint, and the refinished wood floors throughout the inside

  Kim Meeker Southern Vermont Realty Group

  176 Glen Ave, Readsboro, VT 05350
• 

  

  /48

  $296,500

  Sold Nov 21, 2025

  4 Rockwood St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,896 Sq Ft
  • Built 1993

  Last Sold Summary

  • 1% Below List Price
  • $156/SF
  • 6 Days On Market

  Current Estimated Value $307,593

  Last Listing Agent Justine Curry Maple Leaf Real Estate

  4 Rockwood St, Bennington, VT 05201
• 

  

  /29

  Est $714,023

  Not Listed For Sale

  110 Highland Ave, Manchester Center, VT 05255

  • 5 Beds
  • 3.5 Baths
  • 2,912 Sq Ft
  • Built 1890

  110 Highland Ave, Manchester Center, VT 05255

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Jamie Luke TPW Real Estate
• 

  

  /10

  $245,000

  $97K PRICE DROP

  • Land
  • 28.5 Acres
  • $8,596 per Acre

  11 Old County Rd E, Londonderry, VT 05148

  A rare opportunity to own a wooded hillside property with potential southern and western views on a quiet country road in the much coveted village of Landgrove. Priced below the town assessment, the land is in current use, affording a tax savings, with a state permit for a 4-bedroom house. Enjoy all the elements of a Vermont country setting including a mix of mature hardwoods and softwoods,

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  11 Old County Rd E, Londonderry, VT 05148
• 

  

  /40

  $330,000

  Sold Aug 28, 2026

  107 Colbrook Dr, Arlington, VT 05250

  • 3 Beds
  • 1 Bath
  • 1,170 Sq Ft
  • Built 1964

  Last Sold Summary

  • 2% Above List Price
  • $282/SF
  • 4 Days On Market

  Current Estimated Value $276,498

  Last Listing Agent David Shehadi Josiah Allen Real Estate, Inc.

  107 Colbrook Dr, Arlington, VT 05250
• 

  

  /39

  Est $397,891

  Not Listed For Sale

  90 Jennifer Ln, Manchester Center, VT 05255

  • 4 Beds
  • 2 Baths
  • 1,389 Sq Ft
  • Built 1970

  90 Jennifer Ln, Manchester Center, VT 05255

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
• 

  

  /47

  $795,000

  $50K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 3,875 Sq Ft

  1629 Mann Hill Rd N, Pownal, VT 05261

  Facing west to capture breathtaking mountain views and unforgettable sunsets from nearly every room, this exceptional modern farmhouse seamlessly blends timeless character with thoughtful updates. Rich hardwood floors, cozy alcoves, and original beams in the living room create a warm and inviting atmosphere throughout. The spacious floor plan features five generously sized bedrooms, each with its

  Kelley Mccarthy Mahar McCarthy Real Estate

  1629 Mann Hill Rd N, Pownal, VT 05261
• 

  

  /3

  $199,000

  Sold Jul 16, 2026

  43 Limerick Ln, Arlington, VT 05250

  • Land
  • 9,147 Sq Ft
  • $947,619 per Acre

  Last Sold Summary

  • 1 Day On Market

  Current Estimated Value $201,333

  Last Listing Agent Margretta Fischer Wohler Realty Group

  43 Limerick Ln, Arlington, VT 05250
• 

  

  /29

  Est $627,337

  Not Listed For Sale

  36 Boulder Rd, Manchester Center, VT 05255

  • 4 Beds
  • 1.5 Baths
  • 2,512 Sq Ft
  • Built 1825

  36 Boulder Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Susan Bellville Bellville Realty
• 

  

  /56

  $1,775,000

  $425K PRICE DROP Under Contract

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft

  312 Beartown Rd, Manchester Center, VT 05255

  Set on 24 private acres with sweeping mountain views, 312 Beartown Road offers a sense of complete escape while remaining moments from Manchester.Filled with natural light, the four-bedroom residence is thoughtfully designed to capture its extraordinary setting. Every room is oriented to the outdoors, with expansive windows that keep the Vermont landscape always in view.The chef's

  Christiane Carroccio TPW Real Estate

  312 Beartown Rd, Manchester Center, VT 05255
• 

  

  /48

  $230,000

  Sold Sep 11, 2026

  104 Short St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,128 Sq Ft
  • Built 1843

  Last Sold Summary

  • $204/SF
  • 19 Days On Market

  Current Estimated Value $231,175

  Last Listing Agent Lindsey Martin Maple Leaf Real Estate

  104 Short St, Bennington, VT 05201

Showing Results 601 - 640, Page 16 of 18