31,018

Windham County, VT Homes

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  • /31

    $425,000

    Open Sun 12PM - 2PM
    • 2 Beds
    • 2 Baths
    • 1,110 Sq Ft

    65 E Birch Rd Unit 43, Stratton, VT 05155

    Welcome to Your Stratton Mountain GetawayDiscover the ultimate in mountain convenience with this turnkey, ground level condo in the highly sought after Vantage Point community. Featuring a spacious 2 bedroom, 2 bathroom layout, this home boasts a bright, open concept living, dining, and kitchen area designed for effortless entertaining and relaxation. Positioned in an unbeatable location,

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    65 E Birch Rd Unit 43, Stratton, VT 05155
  • /26

    $401,000

    Sold Oct 03, 2025

    215 Old Town Rd, Wilmington, VT 05363

    • 4 Beds
    • 2.5 Baths
    • 2,989 Sq Ft
    • Built 1967

    Last Sold Summary

    • 1% Above List Price
    • $134/SF
    • 5 Days On Market

    Current Estimated Value $458,767

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    215 Old Town Rd, Wilmington, VT 05363
    • /12

      Est $358,800

      Not Listed For Sale

      2812 River Rd, Brattleboro, VT 05301

      • 2 Beds
      • 2 Baths
      • 1,152 Sq Ft
      • Built 2008
      2812 River Rd, Brattleboro, VT 05301

      Last Sold Summary

      • 36 Days On Market

  • /46

    $734,000

    • 3 Beds
    • 5 Baths
    • 4,285 Sq Ft

    258 Chester Rd, Grafton, VT 05146

    Set on a beautifully landscaped parcel just minutes from the heart of historic Grafton, this meticulously maintained residence offers timeless New England charm, exceptional craftsmanship, and inviting spaces. Surrounded by mature trees, perennial gardens, and lush lawns, the property provides a peaceful setting with the perfect balance of privacy and convenience.Inside, warm hardwood floors,

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    258 Chester Rd, Grafton, VT 05146
  • /24

    $22,000

    Sold Apr 01, 2026

    97 Glen St, Brattleboro, VT 05301

    • 2 Beds
    • 1 Bath
    • 684 Sq Ft
    • Built 1968

    Last Sold Summary

    • 26% Below List Price
    • $32/SF
    • 36 Days On Market

    Last Listing Agent Angela Sherman Brattleboro Area Realty

    97 Glen St, Brattleboro, VT 05301
    • /19

      Not Listed For Sale

      5 Spruce Haven Rd, Dover, VT 05356

      • 3 Beds
      • 2.5 Baths
      • 1,200 Sq Ft
      • Built 1975
      5 Spruce Haven Rd, Dover, VT 05356

      Last Sold Summary

      • 6 Days On Market

  • /40

    $490,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,182 Sq Ft

    160 Akley Rd, Guilford, VT 05301

    Here's an open concept, post and beam beauty located on a quiet country road just outside West Brattleboro. Walk through the covered porch into the welcome foyer, where there's plenty of closet space for coats and gear, then enter the main home. The post and beam construction highlights the bright and open spaces. The chef's kitchen is complete with ample cabinet areas, granite counter tops, full

    Bill Hickok Berkley & Veller Greenwood Country

    160 Akley Rd, Guilford, VT 05301
  • /30

    $197,000

    Sold Jan 16, 2026

    77 Griswold Dr, Bellows Falls, VT 05101

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft
    • Built 1964

    Last Sold Summary

    • 30% Below List Price
    • $172/SF
    • 153 Days On Market

    Current Estimated Value $208,043

    Last Listing Agent Rob Weltz Barrett and Valley Associates Inc.

    77 Griswold Dr, Bellows Falls, VT 05101
    • /39

      Not Listed For Sale

      6 Cranberry Ct, Stratton, VT 05360

      • 4 Beds
      • 4 Baths
      • 2,625 Sq Ft
      • Built 2003
      6 Cranberry Ct, Stratton, VT 05360

      Last Sold Summary

      • 32 Days On Market

  • /2

    $350,000

    $30K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 3,312 Sq Ft

    573 S Main St, Brattleboro, VT 05301

    Just around the corner! From the middle and high school, Oak groveelementary! Pop around the corner for all the high school games,exercise at the track. Interstate is minutes away for easy access towork or play! One apartment is over 1,000 square feet so tons of roomfor owner occupancy! 2 nice front porches. Worth looking at for eitheryour own home or as an investment. Masks

    Christine Lewis Brattleboro Area Realty

    573 S Main St, Brattleboro, VT 05301
  • /19

    $475,000

    Sold Oct 30, 2025

    0 Route 9 Unit 4905132, Marlboro, VT 05344

    • Land
    • 195 Acres
    • $2,436 per Acre

    Last Sold Summary

    • 12% Above List Price
    • 1,058 Days On Market

    Last Listing Agent Thom Milke Fountains Land Inc.

    0 Route 9 Unit 4905132, Marlboro, VT 05344
    • /2

      Not Listed For Sale

      5 Town Farm Rd, Town of Rockingham, VT 05101

      • 1 Bed
      • 1 Bath
      5 Town Farm Rd, Town of Rockingham, VT 05101

  • /60

    $3,995,000

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

    816 Black Bear Rd, Jamaica, VT 05343

    Set atop the Vermont hillside with stunning views, offering 4 bedrooms with additional sleeping rooms accommodating up to 16 family and friends. A custom-built home by The Wadsworth Design Build/Vermont Barns is an example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    816 Black Bear Rd, Jamaica, VT 05343
  • /31

    $405,000

    Sold Mar 05, 2026

    132 Pratt Bridge Rd, Jamaica, VT 05343

    • 3 Beds
    • 2 Baths
    • 1,814 Sq Ft
    • Built 1987

    Last Sold Summary

    • 13% Below List Price
    • $223/SF
    • 140 Days On Market

    Current Estimated Value $431,308

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

    132 Pratt Bridge Rd, Jamaica, VT 05343
    • /24

      Est $281,680

      Not Listed For Sale

      7 Hassey Bend Unit 16, Wilmington, VT 05363

      • 2 Beds
      • 2 Baths
      • 1,240 Sq Ft
      • Built 1972
      7 Hassey Bend Unit 16, Wilmington, VT 05363

      Last Sold Summary

      • 49 Days On Market

  • /41

    $2,799,000

    $2M PRICE DROP
    • 6 Beds
    • 3 Baths
    • 3,309 Sq Ft

    36 Woffenden Rd, Wilmington, VT 05363

    Discover the quintessential Vermont lifestyle at historic Wheeler Farm! Nestled amid its own 260+/- acres of scenic beauty, this 6-bedroom farmhouse embodies rural farmhouse charm. Open meadows, green hay fields and the sugarhouse's steam on spring days barely begin to tell the story of all this special property holds. Boasting a coveted southeast exposure, the home and land are cheerful and

    Melissa Ellis Southern Vermont Realty Group

    36 Woffenden Rd, Wilmington, VT 05363
  • /34

    $1,250,000

    Sold Nov 07, 2025

    15 Springhill Rd, Dover, VT 05356

    • 5 Beds
    • 4.5 Baths
    • 5,153 Sq Ft
    • Built 1991

    Last Sold Summary

    • 7% Below List Price
    • $243/SF
    • 119 Days On Market

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    15 Springhill Rd, Dover, VT 05356
    • /22

      Est $932,972

      Not Listed For Sale

      389 Cobble Hill Rd, Londonderry, VT 05148

      • 4 Beds
      • 5 Baths
      • 3,227 Sq Ft
      • Built 1790
      389 Cobble Hill Rd, Londonderry, VT 05148

      Last Sold Summary

      • 277 Days On Market

  • /12

    $36,999

    $3K PRICE DROP
    • Land
    • 2 Acres
    • $18,500 per Acre

    14 Brickyard Rd, Dover, VT 05341

    Beautiful hillside parcel less than ten minutes from Mount Snow but outside the direct path of heavy tourist traffic. Brickyard Road is a winding packed-gravel road dotted sparsely with homes for full-time Dover residents, each with plenty of land and privacy. From the roadside the topography dips down about 5 feet, then quickly comes to a much more gradual slope which continues for approximately

    David White OwnerEntry.com

    14 Brickyard Rd, Dover, VT 05341
  • /34

    $265,000

    Sold Oct 20, 2025

    199 Depot Rd, Williamsville, VT 05362

    • 2 Beds
    • 1 Bath
    • 1,137 Sq Ft
    • Built 1989

    Last Sold Summary

    • 4% Below List Price
    • $233/SF
    • 52 Days On Market

    Current Estimated Value $286,370

    Last Listing Agent Kate Barry EXP Realty

    199 Depot Rd, Williamsville, VT 05362
    • /30

      Est $565,782

      Not Listed For Sale

      4 Robin Hill Rd, Townshend, VT 05353

      • 4 Beds
      • 2.5 Baths
      • 2,600 Sq Ft
      • Built 1967
      4 Robin Hill Rd, Townshend, VT 05353

      Last Sold Summary

      • 5 Days On Market

  • /44

    $350,000

    $75K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    25 Upper Handle Rd Unit A, Dover, VT 05356

    Welcome to this inviting 3-bedroom plus loft, 2-bath Apple Hill condominium—perfectly located just minutes from Mount Snow. This spacious and well-maintained home offers a comfortable layout for a relaxing Vermont getaway. The updated kitchen and dining area feature a charming window seat, while the open-concept living room boasts another cozy window seat and a wood-burning fireplace for those

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    25 Upper Handle Rd Unit A, Dover, VT 05356
  • /60

    $639,000

    Sold Jan 09, 2026

    38 Greenspring Rd, Dover, VT 05356

    • 3 Beds
    • 3.5 Baths
    • 2,472 Sq Ft
    • Built 1990

    Last Sold Summary

    • 1% Below List Price
    • $258/SF
    • 66 Days On Market

    Last Listing Agent Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    38 Greenspring Rd, Dover, VT 05356
    • /6

      Est $93,279

      Not Listed For Sale

      13 Edelweiss, Dover, VT 05356

      13 Edelweiss, Dover, VT 05356

      Last Sold Summary

      • 527 Days On Market

  • /8

    $48,000

    $4K PRICE DROP
    • Land
    • 6.1 Acres
    • $7,869 per Acre

    0 Cooke Rd, Brattleboro, VT 05301

    Amidst rolling VT farmland, sits these 6 acres in West Brattleboro. While there is road frontage on Rte 9, the driveway is off the class 4 section of Cooke Rd. There's about 250 feet of Cooke Rd that you would need to maintain before the town road. The ROW into the land parallels the power lines, which you cannot see when you're on the land. There a nice cleared shelf when you walk in and then

    Victoria Woods Brattleboro Area Realty

    0 Cooke Rd, Brattleboro, VT 05301
  • /32

    $18,000

    Sold Nov 14, 2025

    111, Qtr 3, 89 Grand Summit Way, Dover, VT 05356

    • 1 Bed
    • 1 Bath
    • 608 Sq Ft
    • Built 1998

    Last Sold Summary

    • 10% Below List Price
    • $30/SF
    • 37 Days On Market

    Last Listing Agent Patricia Fitzpatrick Skihome Realty

    111, Qtr 3, 89 Grand Summit Way, Dover, VT 05356
    • /35

      Est $490,239

      Not Listed For Sale

      3796 Vt Route 30, Jamaica, VT 05343

      • 4 Beds
      • 1.5 Baths
      • 3,169 Sq Ft
      • Built 1860
      3796 Vt Route 30, Jamaica, VT 05343

      Last Sold Summary

      • 7 Days On Market

  • /19

    $189,000

    Under Contract
    • 2 Beds
    • 1.5 Baths
    • 966 Sq Ft

    1 Morningside Commons, Brattleboro, VT 05301

    DESIRABLE END UNIT!Why rent when you can buy- giving you peace of mind, an opportunity for stability and building equity. Maybe you are a first-time homebuyer? Or someone who wants to downsize from a bigger house and time-consuming yard chores and projects to a simpler life. An investor? Enjoy easy, affordable, and low-maintenance living in this sweet two-bedroom, 1.5 bath townhouse. Storage

    Stephanie Peduzzi-Baker Brattleboro Area Realty

    1 Morningside Commons, Brattleboro, VT 05301
  • /29

    $358,000

    Sold May 14, 2026

    160 Sunny Acres Rd, Brattleboro, VT 05301

    • 3 Beds
    • 2 Baths
    • 2,160 Sq Ft
    • Built 1952

    Last Sold Summary

    • 7% Above List Price
    • $166/SF
    • 3 Days On Market

    Current Estimated Value $343,610

    Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

    160 Sunny Acres Rd, Brattleboro, VT 05301
    • /34

      Est $917,072

      Not Listed For Sale

      8 Cedar Creek Dr Unit C-2, Wilmington, VT 05363

      • 4 Beds
      • 4 Baths
      • 2,205 Sq Ft
      • Built 2005
      8 Cedar Creek Dr Unit C-2, Wilmington, VT 05363

      Last Sold Summary

      • 5 Days On Market

  • /33

    $339,000

    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft

    57 Timber Ln, Wardsboro, VT 05360

    Conveniently located between Mount Snow and Stratton Resort you'll find this three-bedroom, two-bathroom home surrounded by lush perennial gardens that thrive in the sun of the one-acre lot's southern exposure within the desirable Snow Mountain Farms community of Wardsboro, Vermont. The main level features an inviting open-concept layout that seamlessly connects the galley kitchen with eat-in

    Kim Meeker Southern Vermont Realty Group

    57 Timber Ln, Wardsboro, VT 05360
  • /48

    $490,000

    Sold Jul 01, 2026

    27 Ray Hill Rd, Wilmington, VT 05363

    • 3 Beds
    • 3 Baths
    • 3,420 Sq Ft
    • Built 1976

    Last Sold Summary

    • 4% Below List Price
    • $143/SF
    • 20 Days On Market

    Current Estimated Value $515,168

    Last Listing Agent Monica Sumner BHG Masiello Brattleboro

    27 Ray Hill Rd, Wilmington, VT 05363
    • /31

      Est $664,217

      Not Listed For Sale

      78 Middle Ridge Rd Unit 106, Stratton, VT 05155

      • 2 Beds
      • 3 Baths
      • 1,375 Sq Ft
      • Built 2006
      78 Middle Ridge Rd Unit 106, Stratton, VT 05155

      Last Sold Summary

      • 175 Days On Market

  • /2

    $25,000

    • Land
    • 26,136 Sq Ft
    • $41,667 per Acre

    28 Upper Howes Way, Wilmington, VT 05363

    Sweet Spot tucked away in a quiet corner of the Hill, ready for you to build your vacation getaway. Recent soil tests are favorable for a 3-bedroom house. Enjoy all the amenities Chimney Hill offers on its 1,200 Acre Resort Campus, including year-round swimming, seasonal tennis and pickleball, ice skating with a warming hut full of skates to use, hiking, biking, snowmobiling right from your house

    Sigrid Pickering Chimney Hill Realty

    28 Upper Howes Way, Wilmington, VT 05363
  • /15

    $370,000

    Sold Aug 04, 2025

    761 Stratton Mountain Access Rd Unit 231, Stratton, VT 05360

    • 1 Bed
    • 1 Bath
    • 580 Sq Ft
    • Built 1999

    Last Sold Summary

    • 13% Below List Price
    • $638/SF
    • 120 Days On Market

    Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

    761 Stratton Mountain Access Rd Unit 231, Stratton, VT 05360
    • /31

      Est $505,191

      Not Listed For Sale

      9 Lilla Ln, Wilmington, VT 05363

      • 3 Beds
      • 2 Baths
      • 1,827 Sq Ft
      • Built 1971
      9 Lilla Ln, Wilmington, VT 05363

      Last Sold Summary

      • 10 Days On Market

  • /42

    $499,000

    $26K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,508 Sq Ft

    147 Gilbert Rd, Guilford, VT 05301

    This sweet home is nestled in the serene, and quiet location of Gilbert Rd, a dead end, located on the edge of Newfane but in the quaint town of Marlboro, VT. It has been completely renovated within the past few years by a local high-end builder with an eye for energy efficiency. His workmanship is evident in the renovation. The result: this pristine home gleams with its fresh and inviting

    Monica Sumner BHG Masiello Brattleboro

    147 Gilbert Rd, Guilford, VT 05301
  • /27

    $285,000

    Sold Dec 10, 2025

    91 Carriage Hill Rd, Brattleboro, VT 05301

    • 3 Beds
    • 1 Bath
    • 912 Sq Ft
    • Built 1975

    Last Sold Summary

    • 5% Below List Price
    • $312/SF
    • 41 Days On Market

    Current Estimated Value $290,729

    Last Listing Agent Rebecca Seymour Brattleboro Area Realty

    91 Carriage Hill Rd, Brattleboro, VT 05301
    • /5

      Est $74,531

      Not Listed For Sale

      2 Johnson Hill Rd, Dover, VT 05356

      2 Johnson Hill Rd, Dover, VT 05356

      Last Sold Summary

      • 5 Days On Market

  • /39

    $55,000

    • Land
    • 21,780 Sq Ft
    • $110,000 per Acre

    404 Fox Mountain Rd, Wilmington, VT 05363

    Top of the Hill. Build your dream home! One of 2 remaining lots on the new Fox Mt. Cul de Sac, and the only single lot. These have had recent soil tests showing the lot is suitable for a 3-bedroom home. The Lot is oriented to the Southwest, towards Bennington. Plus, enjoy all the amenities Chimney Hill, the Deerfield Valley and Southern Vermont offer including world class skiing and shredding,

    Sigrid Pickering Chimney Hill Realty

    404 Fox Mountain Rd, Wilmington, VT 05363

Showing Results 201 - 240, Page 6 of 18

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