30,889

Windham County, VT Homes

Section Image
    • /13

      Est $126,664

      Not Listed For Sale

      70 Broad Brook Rd, Vernon, VT 05354

      • 3 Beds
      • Built 1995
      70 Broad Brook Rd, Vernon, VT 05354

      Last Sold Summary

      • 2 Days On Market

  • /44

    $319,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,539 Sq Ft

    380 S Main St, Brattleboro, VT 05301

    Charming and conveniently located, this inviting home is situated less than one mile from the heart of Brattleboro Village. Offering 3–4 bedrooms, including a first-floor bedroom for added flexibility, the home features a practical mudroom entry and a bright, sun-filled dining porch just off the kitchen. The basement provides a dedicated workshop area, laundry space, and ample additional storage.

    Jessica Citera Cummings & Co

    380 S Main St, Brattleboro, VT 05301
  • /41

    $545,000

    Sold Jul 18, 2025

    441 Guilford St, Brattleboro, VT 05301

    • 4 Beds
    • 2 Baths
    • 2,450 Sq Ft
    • Built 1880

    Last Sold Summary

    • 1% Below List Price
    • $222/SF
    • 48 Days On Market

    Current Estimated Value $552,153

    Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country

    441 Guilford St, Brattleboro, VT 05301
    • /35

      Est $292,841

      Not Listed For Sale

      63 Washburn Way, Vernon, VT 05354

      • 4 Beds
      • 1 Bath
      • 1,152 Sq Ft
      • Built 1990
      63 Washburn Way, Vernon, VT 05354

      Last Sold Summary

      • 6 Days On Market

  • /29

    $290,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft

    18 Ripple Ln, Bellows Falls, VT 05101

    Welcome to peaceful country living with room to breathe. Nestled on a private road, this well-maintained 3-bedroom, 13⁄4-bath ranch offers privacy, comfort, and over 13 acres of beautiful land to enjoy. The home's single-level layout provides convenient living with spacious bedrooms, functional living areas, and a comfortable flow for everyday life and entertaining. A two-car garage offers plenty

    Rob Weltz Barrett and Valley Associates Inc.

    18 Ripple Ln, Bellows Falls, VT 05101
  • /44

    $405,000

    Sold Jul 28, 2025

    156 Sherwood Cir, Brattleboro, VT 05301

    • 4 Beds
    • 2.5 Baths
    • 2,132 Sq Ft
    • Built 1998

    Last Sold Summary

    • 8% Above List Price
    • $190/SF
    • 33 Days On Market

    Current Estimated Value $396,160

    Last Listing Agent Fine Homes Group International Keller Williams Realty-Metropolitan

    156 Sherwood Cir, Brattleboro, VT 05301
    • /39

      Est $484,801

      Not Listed For Sale

      131 Woodland Rd, Vernon, VT 05354

      • 3 Beds
      • 2.5 Baths
      • 2,195 Sq Ft
      • Built 1997
      131 Woodland Rd, Vernon, VT 05354

      Last Sold Summary

      • 8 Days On Market

  • /37

    $595,000

    • 3 Beds
    • 3 Baths
    • 2,172 Sq Ft

    171 Green Meadow, Brattleboro, VT 05301

    Immaculate! Lovingly reimagined over two decades, this impeccable residence blends thoughtful design with modern sustainability. The heart of the home is a chef’s kitchen with ample counter space and a spacious pantry with an integrated dining area—perfect for entertaining. Relax in the stunning living room, anchored by a gas insert fireplace crafted by a very talented local mason. Outdoor living

    Thomas Dahlin Berkley & Veller Greenwood Country

    171 Green Meadow, Brattleboro, VT 05301
  • /14

    $65,000

    Sold Jul 11, 2025

    4 Brookwood Dr, West Brattleboro, VT 05301

    • 2 Beds
    • 1.5 Baths
    • 924 Sq Ft
    • Built 1978

    Last Sold Summary

    • 4% Below List Price
    • $70/SF
    • 70 Days On Market

    Last Listing Agent Cassandra Ehrlich BHG Masiello Brattleboro

    4 Brookwood Dr, West Brattleboro, VT 05301
    • /40

      Est $472,492

      Not Listed For Sale

      19 Southern Heights Dr, Vernon, VT 05354

      • 3 Beds
      • 3 Baths
      • 3,551 Sq Ft
      • Built 1988
      19 Southern Heights Dr, Vernon, VT 05354

      Last Sold Summary

      • 119 Days On Market

  • /45

    $329,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,218 Sq Ft

    119 Forest St, Brattleboro, VT 05301

    Great location in the heart of Brattleboro. This 3-bedroom, 1-bathroom Jewel of a home is as efficient as it is charming. Very well maintained, with gorgeous maple floors, built-ins, original natural woodwork, elegant marble countertops, and an open kitchen/dining/living space that shines with a southern exposure. Snug little wood stove adds to the uplifting spirit in this home. Large upstairs

    Kristen Ziter Taylor Brattleboro Area Realty

    119 Forest St, Brattleboro, VT 05301
  • /33

    $377,840

    Sold Aug 19, 2025

    111 Bonnyvale Rd, Brattleboro, VT 05301

    • 3 Beds
    • 1.5 Baths
    • 1,536 Sq Ft
    • Built 2000

    Last Sold Summary

    • 8% Above List Price
    • $246/SF
    • 103 Days On Market

    Current Estimated Value $389,909

    Last Listing Agent Stephanie Peduzzi-Baker Brattleboro Area Realty

    111 Bonnyvale Rd, Brattleboro, VT 05301
    • /40

      Not Listed For Sale

      86 Silver Ln, Vernon, VT 05354

      • 3 Beds
      • 2 Baths
      • 2,139 Sq Ft
      • Built 1973
      86 Silver Ln, Vernon, VT 05354

      Last Sold Summary

      • 87 Days On Market

  • /3

    $125,000

    $50K PRICE DROP
    • Land
    • 1.75 Acres
    • $71,429 per Acre

    0 Fort Dummer Heights Unit 4934976, Brattleboro, VT 05301

    Manicured into a beautiful high meadow, in a nice little neighborhood....sunny with views, what morecould you want? Easy to build!!! The land is open, so no fuss with a lot of prep. This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor

    Christine Lewis Brattleboro Area Realty

    0 Fort Dummer Heights Unit 4934976, Brattleboro, VT 05301
  • /39

    $535,000

    Sold Aug 14, 2025

    408 Dover Rd, South Newfane, VT 05351

    • 3 Beds
    • 3 Baths
    • 2,364 Sq Ft
    • Built 1795

    Last Sold Summary

    • 2% Above List Price
    • $226/SF
    • 23 Days On Market

    Current Estimated Value $528,301

    Last Listing Agent David Brown

    408 Dover Rd, South Newfane, VT 05351
    • /40

      Est $673,938

      Not Listed For Sale

      116 Lily Pond Rd, Vernon, VT 05354

      • 4 Beds
      • 2 Baths
      • 2,273 Sq Ft
      • Built 1855
      116 Lily Pond Rd, Vernon, VT 05354

      Last Sold Summary

      • 11 Days On Market

  • /60

    $439,000

    $56K PRICE DROP Under Contract
    • 4 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    8 Little Bend Unit M-175, Wilmington, VT 05363

    Time to start living the dream with your very own getaway in Chimney Hill! Little Bend Haven is a short walk to the Clubhouse, at the end of the road, with a wood burning fireplace, family room, open concept living, dining and kitchen, with deck, and three levels of living and sleeping spaces. Main level has a mudroom for gear, bedroom and full bath, kitchen/dining, deck with a babbling brook

    Sigrid Pickering Chimney Hill Realty

    8 Little Bend Unit M-175, Wilmington, VT 05363
  • /4

    $232,500

    Sold Sep 18, 2025

    0 Gold Medal Cir Unit 5023219, Stratton, VT 05155

    • Land
    • 1.57 Acres
    • $148,089 per Acre

    Last Sold Summary

    • 7% Below List Price
    • 238 Days On Market

    Last Listing Agent Ross Powers TPW Real Estate

    0 Gold Medal Cir Unit 5023219, Stratton, VT 05155
    • /60

      Est $495,345

      Not Listed For Sale

      434 Scott Rd, Vernon, VT 05354

      • 3 Beds
      • 2 Baths
      • 1,856 Sq Ft
      • Built 1997
      434 Scott Rd, Vernon, VT 05354

      Last Sold Summary

      • 6 Days On Market

  • /36

    $749,000

    $50K PRICE DROP Under Contract
    • 4 Beds
    • 4 Baths
    • 3,691 Sq Ft

    42 Airport Rd, Shaftsbury, VT 05262

    Set just minutes from world class skiing at Mount Snow, this inviting timber frame home offers comfort, convenience, and year-round adventure right outside your door. Located just off the Mount Snow Golf course and with direct access to VAST snowmobile trails, this property is perfectly positioned for ski weekends, snowmobiling adventures, summer hiking, and everything in between. Inside, you’ll

    Mike Masters Four Seasons Sotheby's Int'l Realty

    42 Airport Rd, Shaftsbury, VT 05262
  • /58

    $475,000

    Sold Oct 10, 2025

    1923 N Hill Rd, Chester, VT 05143

    • 5 Beds
    • 3 Baths
    • 2,316 Sq Ft
    • Built 1981

    Last Sold Summary

    • 2% Below List Price
    • $205/SF
    • 6 Days On Market

    Last Listing Agent Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    1923 N Hill Rd, Chester, VT 05143
    • /34

      Est $402,500

      Not Listed For Sale

      458 Hazel Hill Rd, Townshend, VT 05353

      • 3 Beds
      • 2 Baths
      • 2,160 Sq Ft
      • Built 1987
      458 Hazel Hill Rd, Townshend, VT 05353

      Last Sold Summary

      • 9 Days On Market

  • /19

    $229,000

    $56K PRICE DROP Under Contract
    • 2 Beds
    • 1 Bath
    • 960 Sq Ft

    3095 Thompsonburg Rd Unit B/2, Londonderry, VT 05155

    Close to Magic, Bromley and Stratton! This two-bedroom, one bath condo with woodburning fireplace overlooks a beautiful brook and tennis court area. Private deck out back to enjoy some sun. Eat in kitchen with pass through countertop area opens into the living room. Manageable and spacious for a nice weekend getaway or make this your fulltime home. Just minutes to downtown with shopping, fuel,

    Julie Lowe Lowe's Real Estate, LLC

    3095 Thompsonburg Rd Unit B/2, Londonderry, VT 05155
  • /60

    $235,000

    Sold Aug 29, 2025

    111 Binney Brook Rd Unit M581, Wilmington, VT 05363

    • 3 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • Built 1970

    Last Sold Summary

    • 10% Below List Price
    • $188/SF
    • 32 Days On Market

    Current Estimated Value $237,243

    Last Listing Agent Sigrid Pickering Chimney Hill Realty

    111 Binney Brook Rd Unit M581, Wilmington, VT 05363
    • /33

      Est $301,369

      Not Listed For Sale

      60 Riverdale Rd, Townshend, VT 05353

      • 2 Beds
      • 2 Baths
      • 946 Sq Ft
      • Built 1980
      60 Riverdale Rd, Townshend, VT 05353

      Last Sold Summary

      • 91 Days On Market

  • /46

    $625,000

    Pending
    • 5 Beds
    • 3.5 Baths
    • 2,520 Sq Ft

    143 Hillwinds Rd, Brattleboro, VT 05301

    Welcome to Hillwinds and this lovely colonial. With 200 acres of conserved land and trails behind and a wonderful meadow view in the front, this house truly feels a part of the landscape. The main house has four bedrooms and two and a half baths and invites you to step right into your new life in this well cared for and lovingly maintained home. The gardens are in, the drive paved and the garden

    Christine Lewis Brattleboro Area Realty

    143 Hillwinds Rd, Brattleboro, VT 05301
  • /60

    $319,000

    Sold Jun 27, 2025

    6 Bunny Ln Unit (391), Wilmington, VT 05363

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1969

    Last Sold Summary

    • 3% Below List Price
    • $266/SF
    • 120 Days On Market

    Current Estimated Value $322,586

    Last Listing Agent Sigrid Pickering Chimney Hill Realty

    6 Bunny Ln Unit (391), Wilmington, VT 05363
    • /26

      Est $335,749

      Not Listed For Sale

      231 Sawdust Aly, Townshend, VT 05353

      • 3 Beds
      • 2 Baths
      • 1,921 Sq Ft
      • Built 1950
      231 Sawdust Aly, Townshend, VT 05353

      Last Sold Summary

      • 172 Days On Market

  • /50

    $1,800,000

    • 4 Beds
    • 5 Baths
    • 4,853 Sq Ft

    95 Middletown Rd, South Londonderry, VT 05155

    One-of-a-Kind Vermont Lifestyle PropertyHome, Income & Creative Opportunity Welcome to an exceptional Southern Vermont offering that blends refined country living with rare income and lifestyle flexibility. Set on 2.4 picturesque acres in South Londonderry, this beautifully restored 1865 property is first and foremost a warm and inviting 4-bedroom home—rich in character, thoughtfully updated,

    Eric Nathan Nathan Auction & Real Estate Inc.

    95 Middletown Rd, South Londonderry, VT 05155
  • /48

    $391,000

    Sold Apr 07, 2026

    58-60 Frost Place, Brattleboro, VT 05301

    • 6 Beds
    • 2 Baths
    • 2,048 Sq Ft
    • Built 1930

    Last Sold Summary

    • 6% Below List Price
    • $191/SF
    • 142 Days On Market

    Last Listing Agent Lily Gautot Greenwald Realty Group

    58-60 Frost Place, Brattleboro, VT 05301
    • /19

      Est $504,217

      Not Listed For Sale

      12 Depot Rd, Townshend, VT 05353

      • 1 Bed
      • 1,243 Sq Ft
      • Built 1900
      12 Depot Rd, Townshend, VT 05353

      Last Sold Summary

      • 4 Days On Market

  • /27

    $17,500

    $7K PRICE DROP
    • 1 Bed
    • 2 Baths
    • 941 Sq Ft

    230, Qtr. 4 89 Grand Summit Way, Dover, VT 05356

    PRICE IMPROVEMENT! This one-of-a-kind unit-style is on one level and includes one bedroom, two full bathrooms, and an open-concept kitchen, living, and dining area. The living room area features a queen Murphy bed and a queen pull-out sleeper sofa, comfortably sleeping six people. The spacious bedroom includes a king-size bed and a balcony with beautiful ridgeline views. The benefits of Grand

    Patricia Fitzpatrick Skihome Realty

    230, Qtr. 4 89 Grand Summit Way, Dover, VT 05356
  • /30

    $325,000

    Sold Mar 20, 2026

    119 Newton Hill Rd, Vernon, VT 05354

    • 3 Beds
    • 1.5 Baths
    • 1,674 Sq Ft
    • Built 1976

    Last Sold Summary

    • 3% Above List Price
    • $194/SF
    • 7 Days On Market

    Current Estimated Value $328,561

    Last Listing Agent Jim Bellville Bellville Realty

    119 Newton Hill Rd, Vernon, VT 05354
    • /40

      Not Listed For Sale

      3031 Vt Route 30, Townshend, VT 05353

      • 8 Beds
      • 6 Baths
      • 4,790 Sq Ft
      • Built 1960
      3031 Vt Route 30, Townshend, VT 05353

      Last Sold Summary

      • 7 Days On Market

  • /3

    $125,000

    • Land
    • 1.77 Acres
    • $70,621 per Acre

    997 Stratton Arlington Rd, Stratton, VT 05360

    STRATTON & MOUNT SNOW - Build your dream ski home on this newly subdivided lot with 103' of road frontage and 1.77 private acres located only 10 minutes from both Stratton Mountain Ski Resort and Mount Snow Ski Resort. All the hard work has been done! Survey, septic design, site plan, state of VT wastewater and well approval, and driveway permit have all been approved and filed with the town.

    Derek Greene Derek Greene

    997 Stratton Arlington Rd, Stratton, VT 05360
  • /2

    $345,000

    Sold Oct 07, 2025

    154 Reed Rd, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Above List Price
    • $308/SF
    • 10 Days On Market

    Current Estimated Value $248,331

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    154 Reed Rd, Chester, VT 05143
    • /40

      Est $349,179

      Not Listed For Sale

      456 Grafton Rd, Townshend, VT 05353

      • 3 Beds
      • 2 Baths
      • 2,498 Sq Ft
      • Built 1844
      456 Grafton Rd, Townshend, VT 05353

      Last Sold Summary

      • 70 Days On Market

  • /43

    $1,300,000

    Under Contract
    • 3 Beds
    • 4 Baths
    • 2,944 Sq Ft

    156 W Lake Rd, Wilmington, VT 05363

    A rare opportunity to own a beautifully maintained, one-family-owned home on Lake Raponda. Lovingly cared for through the years. This special waterfront property offers the perfect blend of comfort, warmth, and classic Vermont charm. Spend your days boating, kayaking, swimming, or simply relaxing by the shore, and unwind in the quiet beauty that makes Lake Raponda so special. Step inside to an

    Jillian Wimmelman Deerfield Valley Real Estate

    156 W Lake Rd, Wilmington, VT 05363
  • /46

    $449,999

    Sold Jun 16, 2025

    1448 Cyrus Rd, Whitingham, VT 05361

    • 3 Beds
    • 2 Baths
    • 1,438 Sq Ft
    • Built 1978

    Last Sold Summary

    • $313/SF
    • 15 Days On Market

    Current Estimated Value $478,644

    Last Listing Agent Peggy Winchester ACORN REAL ESTATE GROUP LLC

    1448 Cyrus Rd, Whitingham, VT 05361
    • /44

      Est $383,241

      Not Listed For Sale

      556 Stratton Arlington Rd, West Wardsboro, VT 05360

      • 3 Beds
      • 1 Bath
      • 1,080 Sq Ft
      • Built 1952
      556 Stratton Arlington Rd, West Wardsboro, VT 05360

      Last Sold Summary

      • 11 Days On Market

Showing Results 441 - 480, Page 12 of 18

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