Bennington County, VT Homes

• 

  

  

  /37

  Est $739,888

  Not Listed For Sale

  173 N Ridge Run, Manchester Center, VT 05255

  • 3 Beds
  • 3 Baths
  • 1,829 Sq Ft
  • Built 1992

  173 N Ridge Run, Manchester Center, VT 05255

  Last Sold Summary

  • 6 Days On Market
• 

  

  

  /28

  $159,000

  $30K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 760 Sq Ft

  1675 Vermont 9, Searsburg, VT 05363

  Welcome to Peaceful Pines, your cottage in the woods near the entrance to the Green Mountain National Forest. The charming two-bedroom cottage/camp was lovingly maintained. Key updates include a completely rebuilt chimney and masonry work, a wood stove ( in addition to baseboard heat) to take the chill out of those fall and winter evenings, T11 siding, a newer roof, and a private back deck with

  Jacki Murano Southern Vermont Realty Group

  1675 Vermont 9, Searsburg, VT 05363
• 

  

  

  /30

  $290,000

  Sold Jul 17, 2025

  221 Grandview St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,042 Sq Ft
  • Built 1948

  Last Sold Summary

  • 2% Below List Price
  • $278/SF
  • 75 Days On Market

  Current Estimated Value $279,617

  Last Listing Agent Angela Bevin Maple Leaf Real Estate

  221 Grandview St, Bennington, VT 05201
• 

  

  

  /43

  Est $636,273

  Not Listed For Sale

  78 Stoney Fields Rd, Manchester Center, VT 05255

  • 4 Beds
  • 2.5 Baths
  • 1,710 Sq Ft
  • Built 1964

  78 Stoney Fields Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 61 Days On Market
• 

  

  

  /54

  $449,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,586 Sq Ft

  487 Rue Madeline, Readsboro, VT 05350

  Nestled in the scenic hills of Readsboro, Vermont, this beautiful log home offers the perfect blend of rustic charm and moderncomfort. Featuring 3 spacious bedrooms and 2 full bathrooms, the home showcases warm wood finishes throughout, creating aninviting and timeless atmosphere. A finished basement adds valuable flexible space, ideal for a family room, home office, orrecreational

  Colt Hazell Flex Realty

  487 Rue Madeline, Readsboro, VT 05350
• 

  /2

  $275,000

  Sold Jul 22, 2025

  0 Tunic Rd, Shaftsbury, VT 05262

  • Land
  • 138.31 Acres
  • $1,988 per Acre

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Andy Reed Four Seasons Sotheby's Int'l Realty

  0 Tunic Rd, Shaftsbury, VT 05262
• 

  

  /31

  Est $482,960

  Not Listed For Sale

  6344 Main St, Manchester Center, VT 05255

  • 2 Beds
  • 1 Bath
  • 1,244 Sq Ft
  • Built 1950

  6344 Main St, Manchester Center, VT 05255

  Last Sold Summary

  • 4 Days On Market
• 

  

  /38

  $309,900

  $15K PRICE DROP Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,900 Sq Ft

  2 Pine Rd, Bennington, VT 05201

  Bright 3 bedroom, 1 and a half bath home in Bennington. Close to the hospital and offering kitchen, formal dining room, living room, and 2 main level bedrooms. Upstairs a loft office area and another bedroom. The basement is partially finished with laundry, family room and half bath. Outside there is a great deck with a separate, heated sun room and 2 car detached garage. A must see home in a

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  2 Pine Rd, Bennington, VT 05201
• 

  

  /22

  $175,000

  Sold Sep 11, 2025

  6967 Main St, Readsboro, VT 05350

  • 6 Beds
  • 2 Baths
  • 2,116 Sq Ft
  • Built 1870

  Last Sold Summary

  • 22% Below List Price
  • $83/SF
  • 70 Days On Market

  Current Estimated Value $179,244

  Last Listing Agent Cassandra Ehrlich BHG Masiello Brattleboro

  6967 Main St, Readsboro, VT 05350
• 

  

  /34

  Est $881,399

  Not Listed For Sale

  50 Ways Ln, Manchester Center, VT 05255

  • 3 Beds
  • 3 Baths
  • 3,196 Sq Ft
  • Built 1970

  50 Ways Ln, Manchester Center, VT 05255

  Last Sold Summary

  • 13 Days On Market
• 

  /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
• 

  

  /53

  $495,000

  Sold Oct 17, 2025

  200 Applewood Ln, Manchester Center, VT 05255

  • 2,746 Sq Ft
  • Built 1986

  Last Sold Summary

  • $180/SF
  • 4 Days On Market

  Current Estimated Value $505,492

  Last Listing Agent Zachary Zupan EXP Realty

  200 Applewood Ln, Manchester Center, VT 05255
• 

  

  /29

  Est $603,786

  Not Listed For Sale

  271 Nottingham Park, Manchester Center, VT 05255

  • 3 Beds
  • 3 Baths
  • 1,422 Sq Ft
  • Built 1986

  271 Nottingham Park, Manchester Center, VT 05255

  Last Sold Summary

  • 55 Days On Market
• 

  

  /29

  $395,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,556 Sq Ft

  231 Washington Ave, Bennington, VT 05201

  Charming vintage 1920s Arts & Crafts-style cottage in a prime village location. This inviting home offers seven main rooms, including three bedrooms and two baths, blending timeless character with modern comfort. The updated kitchen features abundant storage and flows nicely into the living spaces, highlighted by beautiful wood floors and a cozy fireplace. Central air ensures year-round comfort.

  Kelley Mccarthy Mahar McCarthy Real Estate

  231 Washington Ave, Bennington, VT 05201
• 

  

  /42

  $529,000

  Sold Apr 15, 2026

  941 Myers Rd, Shaftsbury, VT 05262

  • 4 Beds
  • 2.5 Baths
  • 1,882 Sq Ft
  • Built 1900

  Last Sold Summary

  • $281/SF
  • 2 Days On Market

  Current Estimated Value $521,065

  Last Listing Agent Abi Gregorio

  941 Myers Rd, Shaftsbury, VT 05262
• 

  

  /17

  Est $397,514

  Not Listed For Sale

  7935 Main St, Manchester Center, VT 05255

  • 4 Beds
  • 2 Baths
  • 1,382 Sq Ft
  • Built 1775

  7935 Main St, Manchester Center, VT 05255

  Last Sold Summary

  • 229 Days On Market
• 

  

  /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
• 

  

  /22

  $265,500

  Sold Jul 15, 2025

  18 Stratton Ridge Rd, Winhall, VT 05340

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft
  • Built 1970

  Last Sold Summary

  • 16% Below List Price
  • $199/SF
  • 72 Days On Market

  Last Listing Agent Derek Greene Derek Greene

  18 Stratton Ridge Rd, Winhall, VT 05340
• 

  

  /6

  Est $406,045

  Not Listed For Sale

  59 Bond St, Manchester Center, VT 05255

  • 3 Beds
  • 1.5 Baths
  • 1,536 Sq Ft
  • Built 1948

  59 Bond St, Manchester Center, VT 05255

  Last Sold Summary

  • 6 Days On Market
• 

  

  /40

  $5,900,000

  $1M PRICE DROP

  • 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 design of 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
• 

  

  /21

  $120,000

  Sold Mar 09, 2026

  1319 Vail Rd, Bennington, VT 05201

  • Land
  • 20 Acres
  • $6,000 per Acre

  Last Sold Summary

  • 143 Days On Market

  Last Listing Agent Lilli West Maple Leaf Real Estate

  1319 Vail Rd, Bennington, VT 05201
• 

  

  /24

  Est $564,501

  Not Listed For Sale

  159 Hillcrest Rd, Manchester Center, VT 05255

  • 3 Beds
  • 2 Baths
  • 2,112 Sq Ft
  • Built 1972

  159 Hillcrest Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 8 Days On Market
• 

  

  /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
• 

  

  /48

  $306,250

  Sold Dec 05, 2025

  4581 Main Rd, Stamford, VT 05352

  • 3 Beds
  • 2.5 Baths
  • 2,052 Sq Ft
  • Built 1967

  Last Sold Summary

  • 18% Above List Price
  • $149/SF
  • 21 Days On Market

  Current Estimated Value $318,189

  Last Listing Agent Susan Colvin MONARCH REALTY, INC.

  4581 Main Rd, Stamford, VT 05352
• 

  

  /27

  Est $630,825

  Not Listed For Sale

  211 Little John Dr, Manchester Center, VT 05255

  • 3 Beds
  • 2 Baths
  • 1,362 Sq Ft
  • Built 1980

  211 Little John Dr, Manchester Center, VT 05255

  Last Sold Summary

  • 68 Days On Market
• 

  

  /47

  $845,000

  • 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 stunning modern farmhouse seamlessly blends timeless character with thoughtful updates. Rich hardwood floors and cozy alcoves create warmth and charm throughout, while original beams in the living room add a touch of history and authenticity. The spacious layout offers 5 bedrooms, each with

  Kelley Mccarthy Mahar McCarthy Real Estate

  1629 Mann Hill Rd N, Pownal, VT 05261
• 

  

  /16

  $25,000

  Sold Jul 16, 2025

  0 Hawley Mountain Rd, Arlington, VT 05250

  • Land
  • 7 Acres
  • $3,571 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 15 Days On Market

  Last Listing Agent Faith Rhodes Maple Leaf Real Estate

  0 Hawley Mountain Rd, Arlington, VT 05250
• 

  

  /26

  Est $448,919

  Not Listed For Sale

  37 Brookside Rd, Manchester Center, VT 05255

  • 3 Beds
  • 2 Baths
  • 1,268 Sq Ft
  • Built 1968

  37 Brookside Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 26 Days On Market
• 

  

  /56

  $2,200,000

  • 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 kitchen

  Christiane Carroccio TPW Real Estate

  312 Beartown Rd, Manchester Center, VT 05255
• 

  

  /27

  $300,000

  Sold Dec 11, 2025

  0 Rock Bottom Ln, Peru, VT 05152

  • Land
  • 53 Acres
  • $5,660 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 156 Days On Market

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

  0 Rock Bottom Ln, Peru, VT 05152
• 

  

  /31

  Est $549,062

  Not Listed For Sale

  1 Cass Terrace, Manchester Center, VT 05255

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft
  • Built 1913

  1 Cass Terrace, Manchester Center, VT 05255

  Last Sold Summary

  • 7 Days On Market
• 

  

  /54

  $495,000

  Coming Soon

  • 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
• 

  

  /47

  $240,000

  Sold Sep 24, 2025

  120 Imperial Ave, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 2,404 Sq Ft
  • Built 1895

  Last Sold Summary

  • 20% Below List Price
  • $100/SF
  • 114 Days On Market

  Current Estimated Value $265,512

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  120 Imperial Ave, Bennington, VT 05201
• 

  

  /40

  Est $1,024,663

  Not Listed For Sale

  292 Johnnycake St, Manchester Center, VT 05255

  • 4 Beds
  • 3 Baths
  • 3,228 Sq Ft
  • Built 1984

  292 Johnnycake St, Manchester Center, VT 05255

  Last Sold Summary

  • 100 Days On Market
• 

  

  /12

  $299,999

  • Land
  • 10.05 Acres
  • $29,851 per Acre

  00 Garden Loop Rd, Winhall, VT 05340

  The largest remaining vacant lot on the Stratton Mountain access road. Ten acres deeded for one magnificent home. The lot is wooded with some clearing on the east side. There's a roughed-in driveway here too, making it the best spot for construction. In the center of the property is a small pond--about a tenth of an acre--and west of that a scenic perennial creek winds its way downhill along the

  David White OwnerEntry.com

  00 Garden Loop Rd, Winhall, VT 05340
• 

  

  /46

  $1,270,000

  Sold Mar 20, 2026

  33 Forest Haunts Rd, Winhall, VT 05340

  • 4 Beds
  • 4 Baths
  • 4,640 Sq Ft
  • Built 1989

  Last Sold Summary

  • 15% Below List Price
  • $274/SF
  • 487 Days On Market

  Current Estimated Value $1,320,511

  Last Listing Agent Timothy Apps Four Seasons Sotheby's Int'l Realty

  33 Forest Haunts Rd, Winhall, VT 05340
• 

  

  /24

  Est $585,277

  Not Listed For Sale

  2071 Barnumville Rd, Manchester Center, VT 05255

  • 3 Beds
  • 3 Baths
  • 1,792 Sq Ft
  • Built 1980

  2071 Barnumville Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 47 Days On Market
• 

  

  /45

  $275,000

  $20K 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
• 

  

  /43

  $1,374,000

  Sold May 21, 2026

  12 Sunny Hill Rd, Manchester Center, VT 05255

  • 4 Beds
  • 3.5 Baths
  • 5,397 Sq Ft
  • Built 1976

  Last Sold Summary

  • 2% Below List Price
  • $255/SF
  • 50 Days On Market

  Current Estimated Value $793,543

  Last Listing Agent Carrie Mathews Winhall Real Estate

  12 Sunny Hill Rd, Manchester Center, VT 05255
• 

  

  /40

  Est $774,057

  Not Listed For Sale

  2313 Barnumville Rd, Manchester Center, VT 05255

  • 3 Beds
  • 3 Baths
  • 3,891 Sq Ft
  • Built 1983

  2313 Barnumville Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 3 Days On Market

Showing Results 641 - 680, Page 17 of 18