Windham County, VT Homes

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  /2

  $34,995

  Sold Sep 26, 2025

  0 Upper Oak Hill Rd, Newfane, VT 05345

  • Land
  • 1.5 Acres
  • $23,330 per Acre

  Last Sold Summary

  • 30% Below List Price
  • 318 Days On Market

  Last Listing Agent Eric Scott Barrett & Valley Assoc. Inc

  0 Upper Oak Hill Rd, Newfane, VT 05345
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  /38

  Est $360,791

  Not Listed For Sale

  426 Missing Link Rd, Bellows Falls, VT 05101

  • 3 Beds
  • 1.5 Baths
  • 2,248 Sq Ft
  • Built 1852

  426 Missing Link Rd, Bellows Falls, VT 05101

  Last Sold Summary

  • 19 Days On Market
• 

  

  

  /32

  $775,000

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  15 Bears Den Rd, Dover, VT 05356

  A rare opportunity to enjoy the best of both worlds — the privacy of a single-family home with the convenience and access of condo-style living. This unique vacation home offers direct ski-home access in the sought-after Bears Crossing community on the slopes of Mount Snow. Ski back from the Carinthia trails and step out of your gear just across the street from your front door. Designed with both

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Bears Den Rd, Dover, VT 05356
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  /13

  $285,000

  Sold Apr 07, 2026

  0 Ellen Ware Rd, Townshend, VT 05353

  • Land
  • 133 Acres
  • $2,143 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 1 Day On Market

  Last Listing Agent Victoria Woods Brattleboro Area Realty

  0 Ellen Ware Rd, Townshend, VT 05353
• 

  

  

  /40

  Est $405,729

  Not Listed For Sale

  355 Missing Link Rd, Bellows Falls, VT 05101

  • 3 Beds
  • 2 Baths
  • 2,033 Sq Ft
  • Built 1780

  355 Missing Link Rd, Bellows Falls, VT 05101

  Last Sold Summary

  • 32 Days On Market
• 

  /2

  $195,000

  Under Contract

  • Land
  • 4.86 Acres
  • $40,123 per Acre

  1036 Dalewood Rd, Jamaica, VT 05343

  This is a town sale property. There is a 30-day waiting period after a fully executed contract. The 30 days is a window for public feedback. Under the statute, if Town residents object to the sale, they have 30 days from the date of the notice to submit a petition to the Town. If a petition is signed by at least 5% of the town's registered voters, the Select Board cannot just sell the property.

  Carrie Mathews Winhall Real Estate

  1036 Dalewood Rd, Jamaica, VT 05343
• 

  

  /25

  $70,000

  Sold Nov 18, 2025

  2418 Back Westminster Rd, Westminster, VT 05158

  • 2 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Built 1936

  Last Sold Summary

  • 62% Below List Price
  • $54/SF
  • 97 Days On Market

  Current Estimated Value $86,447

  Last Listing Agent Lily Gautot Greenwald Realty Group

  2418 Back Westminster Rd, Westminster, VT 05158
• 

  

  /25

  Est $363,281

  Not Listed For Sale

  9 Old River Rd, Bellows Falls, VT 05101

  • 3 Beds
  • Built 1973

  9 Old River Rd, Bellows Falls, VT 05101

  Last Sold Summary

  • 172 Days On Market
• 

  

  /28

  $325,000

  $25K PRICE INCREASE

  • 5 Beds
  • 3 Baths
  • 2,209 Sq Ft

  16 Washington St, Brattleboro, VT 05301

  Fabulous potential with this in-town home on a great neighborhood street just a few short minutes to downtown Brattleboro where you'll find shops, restaurants, galleries, and more! Close to the hospital, schools, and points north and south with easy access to Rt 91. This home retains much of the original woodwork with bulls eye trim for the doors, an elegant staircase with two stained glass

  Rebecca Seymour Brattleboro Area Realty

  16 Washington St, Brattleboro, VT 05301
• 

  

  /40

  $650,000

  Sold Nov 14, 2025

  134 Ellis Brook Rd, Dover, VT 05356

  • 3 Beds
  • 3.5 Baths
  • 2,250 Sq Ft
  • Built 1984

  Last Sold Summary

  • 10% Below List Price
  • $289/SF
  • 63 Days On Market

  Current Estimated Value $646,581

  Last Listing Agent Jennifer Hovey-Densmore Deerfield Valley Real Estate

  134 Ellis Brook Rd, Dover, VT 05356
• 

  

  /15

  Est $390,276

  Not Listed For Sale

  157 Parker Hill Rd, Bellows Falls, VT 05101

  • 2 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • Built 1978

  157 Parker Hill Rd, Bellows Falls, VT 05101

  Last Sold Summary

  • 67 Days On Market
• 

  

  /43

  $1,392,000

  • 5 Beds
  • 4.5 Baths
  • 5,160 Sq Ft

  224 Cobble Ridge Rd, Londonderry, VT 05148

  Set on seven private fenced acres with stone walls and dual gated entrances, this custom Vermont property offers privacy, flexibility, and year-round access to Southern Vermont's premier recreational destinations.Perched on scenic Cobble Ridge in Londonderry, the property enjoys southwest exposure and seasonal Green Mountain views. Natural light fills the great room, where a brick fireplace

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  224 Cobble Ridge Rd, Londonderry, VT 05148
• 

  

  /10

  $46,000

  Sold Jun 03, 2026

  123 U S 5, Westminster, VT 05158

  • Land
  • 3.2 Acres
  • $14,375 per Acre

  Last Sold Summary

  • 2% Above List Price
  • 14 Days On Market

  Last Listing Agent Laura D'Angelo Berkley & Veller Greenwood Country

  123 U S 5, Westminster, VT 05158
• 

  

  /26

  Est $223,313

  Not Listed For Sale

  908 Pleasant Valley Rd, Bellows Falls, VT 05101

  • 3 Beds
  • 1.5 Baths
  • 1,848 Sq Ft
  • Built 1968

  908 Pleasant Valley Rd, Bellows Falls, VT 05101

  Last Sold Summary

  • 119 Days On Market
• 

  

  /23

  $30,000

  • Land
  • 21,780 Sq Ft
  • $60,000 per Acre

  Lot 118 High Top Rd, Wilmington, VT 05363

  Section B building lot! 1/2 Acre of level, flat land at the end of the cul-de-sac. Site is untested. Build your dream home and start planning your vacation getaway design! As a Lot owner, you may enjoy all of the recreational amenities Chimney Hill Resort offers on its 1,200 Acre Campus. Once you start building, Chimney Hill Owners Association also supplies a water line at the street for you to

  Sigrid Pickering Chimney Hill Realty

  Lot 118 High Top Rd, Wilmington, VT 05363
• 

  

  /42

  $300,000

  Sold Aug 25, 2025

  32 Sugar Maple Dr, East Dummerston, VT 05346

  • 3 Beds
  • 1 Bath
  • 1,239 Sq Ft
  • Built 1972

  Last Sold Summary

  • 11% Above List Price
  • $242/SF
  • 4 Days On Market

  Current Estimated Value $295,019

  Last Listing Agent Steve Schoppmeyer BHG Masiello Brattleboro

  32 Sugar Maple Dr, East Dummerston, VT 05346
• 

  

  /28

  Est $421,389

  Not Listed For Sale

  125 Randall Hill Rd, Bellows Falls, VT 05101

  • 3 Beds
  • 2 Baths
  • 1,535 Sq Ft
  • Built 1988

  125 Randall Hill Rd, Bellows Falls, VT 05101

  Last Sold Summary

  • 14 Days On Market
• 

  

  /4

  $55,000

  • Land
  • 1.05 Acres
  • $52,381 per Acre

  31 Woodsman Rd, West Dover, VT 05356

  Lovely wooded building site not far from the Mount Snow ski resort, nearby lakes, villages, shopping, and dining. The Woodsman development features large private home sites affording great privacy with thick tree buffers, public sewer hookups, easy access of a paved road nearby and tremendous site potential. This lot has been priced to sell!

  Adam Palmiter Berkley & Veller Greenwood/Dover

  31 Woodsman Rd, West Dover, VT 05356
• 

  

  /10

  $345,000

  Sold Nov 06, 2025

  85 E Birch Rd Unit 15, Stratton, VT 05360

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft
  • Built 1982

  Last Sold Summary

  • 4% Below List Price
  • $308/SF
  • 22 Days On Market

  Last Listing Agent Edwin Kevil Stratton Real Estate

  85 E Birch Rd Unit 15, Stratton, VT 05360
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  /31

  Est $309,722

  Not Listed For Sale

  115 Randall Hill Rd, Bellows Falls, VT 05101

  • 2 Beds
  • 1.5 Baths
  • 2,030 Sq Ft
  • Built 1978

  115 Randall Hill Rd, Bellows Falls, VT 05101

  Last Sold Summary

  • 10 Days On Market

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