30,889

Windham County, VT Homes

Section Image
  • /60

    $489,000

    Sold May 13, 2026

    23 Wilsons Woods Rd, Brattleboro, VT 05301

    • 4 Beds
    • 3.5 Baths
    • 2,312 Sq Ft
    • Built 1998

    Last Sold Summary

    • 2% Below List Price
    • $212/SF
    • 35 Days On Market

    Current Estimated Value $499,255

    Last Listing Agent Kate Barry EXP Realty

    23 Wilsons Woods Rd, Brattleboro, VT 05301
    • /5

      Est $74,261

      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

  • /9

    $198,000

    • Land
    • 31,798 Sq Ft
    • $271,233 per Acre

    5 Pinnacle View Rd, Dover, VT 05356

    With views of Mount Snow, this exceptional 0.73-acre parcel is the perfect setting for your dream mountain retreat. Located in the resort district, short-term rentals are permitted, making this a prime investment opportunity or an ideal family legacy home for generations to enjoy. Just off Route 100, a one-minute drive to the lifts at Mount Snow,an Epic Pass mountain, offering world-class skiing

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    5 Pinnacle View Rd, Dover, VT 05356
  • /2

    $430,000

    Sold Apr 02, 2026

    34 Snow Tree Ln Unit K, West Dover, VT 05356

    • 2 Beds
    • 2 Baths
    • 1,012 Sq Ft
    • Built 1984

    Last Sold Summary

    • 1% Above List Price
    • $425/SF
    • 2 Days On Market

    Current Estimated Value $432,613

    Last Listing Agent Erica Reynolds Southern Vermont Realty Group

    34 Snow Tree Ln Unit K, West Dover, VT 05356
    • /14

      Est $80,961

      Not Listed For Sale

      10 Windsor Rd, Bellows Falls, VT 05101

      10 Windsor Rd, Bellows Falls, VT 05101

      Last Sold Summary

      • 12 Days On Market

  • /46

    $799,000

    • 4 Beds
    • 2.5 Baths
    • 2,353 Sq Ft

    2416 Stage Rd, Guilford, VT 05301

    A truly magical setting! If you've never experienced the blissfulness of the Green River Village and its historic covered bridge and crib dam/waterfall and one of the most spectacular swimming holes imaginable, it's a must visit southern Vermont destination. Nestled in this picturesque valley village is this charming old home privately situated on 53.5 acres only a short stroll up the driveway

    Chris Long BHG Masiello Brattleboro

    2416 Stage Rd, Guilford, VT 05301
  • /31

    $250,000

    Sold Jun 13, 2025

    82 Two Brook Dr, Wilmington, VT 05363

    • 3 Beds
    • 1.5 Baths
    • 1,153 Sq Ft
    • Built 1976

    Last Sold Summary

    • 44% Below List Price
    • $217/SF
    • 361 Days On Market

    Current Estimated Value $264,889

    Last Listing Agent Tony Tribuno Skihome Realty

    82 Two Brook Dr, Wilmington, VT 05363
    • /11

      Not Listed For Sale

      3960 Jacksonville Stage Rd, West Halifax, VT 05358

      3960 Jacksonville Stage Rd, West Halifax, VT 05358

      Last Sold Summary

      • 6 Days On Market

  • /2

    $245,000

    • 4 Beds
    • 2 Baths
    • 2,148 Sq Ft

    69 Grove St, Brattleboro, VT 05301

    69 Grove Street is a pleasant 2 unit home just a short walk from vibrant downtown. Each unit features 2 bedrooms, bath, living room and kitchen with wide board flooring and replacement windows. The first floor unit has a covered front porch, pantry and W&D hookups in the basement. The second floor apartment has an additional room (office), W&D hookups, decking and a rear staircase. Recent

    Robert Doyle Berkley & Veller Greenwood Country

    69 Grove St, Brattleboro, VT 05301
  • /52

    $1,600,000

    Sold Apr 06, 2026

    122 Sunbowl Ridge Rd, Stratton, VT 05360

    • 4 Beds
    • 3.5 Baths
    • 2,698 Sq Ft
    • Built 2001

    Last Sold Summary

    • 7% Below List Price
    • $593/SF
    • 153 Days On Market

    Last Listing Agent John Sikes Stratton Real Estate

    122 Sunbowl Ridge Rd, Stratton, VT 05360
    • /9

      Not Listed For Sale

      0 Parker Hill Rd, Bellows Falls, VT 05101

      0 Parker Hill Rd, Bellows Falls, VT 05101

      Last Sold Summary

      • 284 Days On Market

  • /37

    $50,000

    • Land
    • 40,510 Sq Ft
    • $53,763 per Acre

    564 Upper Dam Rd, Wilmington, VT 05363

    Double lot on top of the Hill! Recent soil tests say this looks good for a 3-bedroom home! If you've been thinking of building your dream home, this is a great spot. Walk to the Clubhouse, seasonal views, about 2,400' in elevation, facing SE. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season tennis, basketball, pickleball, ice skating, pond fishing, hiking,

    Sigrid Pickering Chimney Hill Realty

    564 Upper Dam Rd, Wilmington, VT 05363
  • /2

    $692,000

    Sold Oct 03, 2025

    19 Village Lodge Rd Unit 207, Stratton, VT 05155

    • 2 Beds
    • 2 Baths
    • 1,663 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Below List Price
    • $416/SF
    • 0 Days On Market

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    19 Village Lodge Rd Unit 207, Stratton, VT 05155
    • /5

      Est $99,484

      Not Listed For Sale

      29 Woodsman Rd, West Dover, VT 05356

      29 Woodsman Rd, West Dover, VT 05356

      Last Sold Summary

      • 25 Days On Market

  • /24

    $139,000

    $20K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 592 Sq Ft

    219 High St Unit 3, Brattleboro, VT 05301

    Welcome to the effortless existence of condominium life with the rare addition of uniqueness. How nice to own a home while splitting the expenses with two other condo owners. Park in your driveway and follow a pretty stone path to your first-floor sanctuary. This efficient 592 sq ft space offers an open kitchen, dining area with a washer and dryer, living room, one bedroom, and a full bath. Share

    Kristen Ziter Taylor Brattleboro Area Realty

    219 High St Unit 3, Brattleboro, VT 05301
  • /38

    $109,000

    Sold Jul 30, 2025

    16 Jones Hill Rd, Newfane, VT 05362

    • 3 Beds
    • 1 Bath
    • 1,400 Sq Ft
    • Built 1938

    Last Sold Summary

    • 3% Below List Price
    • $78/SF
    • 6 Days On Market

    Current Estimated Value $164,572

    Last Listing Agent Robert Balewicz Evergreen Realty of Vermont

    16 Jones Hill Rd, Newfane, VT 05362
    • /12

      Est $626,489

      Not Listed For Sale

      58 Oak St, Brattleboro, VT 05301

      • 3 Beds
      • 2 Baths
      • 3,400 Sq Ft
      • Built 1867
      58 Oak St, Brattleboro, VT 05301

      Last Sold Summary

      • 20 Days On Market

  • /58

    $350,000

    • 3 Beds
    • 1.5 Baths
    • 1,800 Sq Ft

    422 Governor Hunt Rd, Vernon, VT 05354

    Extremely well-built 3-bedroom, 1.5-bath home with a full basement and ideally located across from Vernon Elementary School. This inviting property sits on a level, sunny 1.5-acre lot framed by mature trees and features a sidewalk along the road, adding both convenience and neighborhood charm.The home offers both a front and rear screened-in porch, perfect for relaxing, entertaining, or

    Kerry Mulverhill

    422 Governor Hunt Rd, Vernon, VT 05354
  • /46

    $299,000

    Sold Jan 22, 2026

    4410 Pikes Falls Rd, Jamaica, VT 05343

    • 3 Beds
    • 2 Baths
    • 2,194 Sq Ft
    • Built 1962

    Last Sold Summary

    • 5% Below List Price
    • $136/SF
    • 5 Days On Market

    Last Listing Agent Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

    4410 Pikes Falls Rd, Jamaica, VT 05343
    • /39

      Not Listed For Sale

      18 Bellows Falls Rd, Putney, VT 05346

      • 5 Beds
      • 3 Baths
      • 2,650 Sq Ft
      • Built 1870
      18 Bellows Falls Rd, Putney, VT 05346

      Last Sold Summary

      • 322 Days On Market

  • /31

    $459,000

    • 1 Bed
    • 2.5 Baths
    • 2,076 Sq Ft

    33 W Main St, Wilmington, VT 05363

    Unique opportunity to own a commercial building in the heart of downtown Wilmington. This historic structure has been completely overhauled and meticulously maintained by the current owners, and was the location of a successful restaurant for many years, with an income producing apartment upstairs. It is now being offered to a buyer with vision who may be looking for prime retail, restaurant, or

    Adam Palmiter Berkley & Veller Greenwood/Dover

    33 W Main St, Wilmington, VT 05363
  • /51

    $343,000

    Sold Jun 23, 2025

    442 S Wardsboro Rd, Newfane, VT 05345

    • 3 Beds
    • 2 Baths
    • 1,538 Sq Ft
    • Built 1795

    Last Sold Summary

    • 4% Above List Price
    • $223/SF
    • 7 Days On Market

    Current Estimated Value $337,045

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

    442 S Wardsboro Rd, Newfane, VT 05345
    • /22

      Not Listed For Sale

      0 Bills Rd, Stratton, VT 05360

      0 Bills Rd, Stratton, VT 05360

      Last Sold Summary

      • 119 Days On Market

  • /58

    $329,000

    $46K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,840 Sq Ft

    1192 Chapel Hill Rd, Whitingham, VT 05361

    Discover Vermont living at its finest in this architecturally unique round home, set on a 1-acre lot. Included in the sale is an additional 1-acre parcel directly across the street, offering potential for a garage, guest house, or Airbnb. Buyers should perform their own due diligence, as seller and broker make no representation on buildability. Step inside and walk into the welcoming lower level,

    Cliff Leinonen Four Seasons Sotheby's Int'l Realty

    1192 Chapel Hill Rd, Whitingham, VT 05361
  • /37

    $375,000

    Sold Jun 16, 2025

    146 Sherwood Cir, Brattleboro, VT 05301

    • 3 Beds
    • 1.5 Baths
    • 1,632 Sq Ft
    • Built 1998

    Last Sold Summary

    • 7% Above List Price
    • $230/SF
    • 66 Days On Market

    Current Estimated Value $388,661

    Last Listing Agent Kate Barry EXP Realty

    146 Sherwood Cir, Brattleboro, VT 05301
    • /32

      Not Listed For Sale

      432 Route 121, Westminster, VT 05158

      • 6 Beds
      • 2 Baths
      • 2,899 Sq Ft
      • Built 1903
      432 Route 121, Westminster, VT 05158

      Last Sold Summary

      • 148 Days On Market

  • /41

    $445,000

    • 2 Beds
    • 2 Baths
    • 1,060 Sq Ft

    5 Sports Center Village Way Unit A-11, Dover, VT 05356

    Ski-to this charming 2 bedroom, 2 bath condo at Seasons on Mount Snow. Conveniently located, a 5 minute walk to the slopes and steps away from the incredible amenity center. Seasons is known for having one of the best amenity packages at Mount Snow, including indoor/outdoor pools, hot tubs, fitness center, game room, locker rooms, tennis courts, owner lounge, and so much more. The open concept

    Jillian Wimmelman Deerfield Valley Real Estate

    5 Sports Center Village Way Unit A-11, Dover, VT 05356
  • /30

    $105,000

    Sold Dec 03, 2025

    10 Taylor St, Town of Rockingham, VT 05101

    • 1,968 Sq Ft
    • Built 1910

    Last Sold Summary

    • 16% Below List Price
    • $53/SF
    • 97 Days On Market

    Current Estimated Value $106,248

    Last Listing Agent Julie Buffum Buffum Realty

    10 Taylor St, Town of Rockingham, VT 05101
    • /3

      Est $408,403

      Not Listed For Sale

      394 Canal St, Brattleboro, VT 05301

      • Studio
      • 2 Baths
      • 2,863 Sq Ft
      • Built 1930
      394 Canal St, Brattleboro, VT 05301

      Last Sold Summary

      • 0 Days On Market

  • /16

    $26,000

    $3K PRICE DROP
    • 1 Bed
    • 2 Baths
    • 771 Sq Ft

    163/65 Qtr.1,89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This sleep 8 unit consists of two adjoining units. Studio unit (unit 163) Queen murphy bed and queen sleeper sofa, kitchenette and full bathroom. Hotel unit (165) Two queen beds, Full bathroom and a deck. Units are located the valley side of the hotel. Benefits of Grand Summit ownership include the best ski in/out mountain

    Kelly Agrillo Southern Vermont Realty Group

    163/65 Qtr.1,89 Grand Summit Way, Dover, VT 05356
  • /2

    $80,000

    Sold Dec 19, 2025

    Lot #3 Peachtree Ln, Brattleboro, VT 05301

    • Land
    • 4.27 Acres
    • $18,735 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 50 Days On Market

    Last Listing Agent Desiree Stango Berkley & Veller Greenwood Country

    Lot #3 Peachtree Ln, Brattleboro, VT 05301
    • /40

      Est $559,603

      Not Listed For Sale

      1084 Cyrus Rd, Whitingham, VT 05361

      • 3 Beds
      • 4 Baths
      • 2,200 Sq Ft
      • Built 2005
      1084 Cyrus Rd, Whitingham, VT 05361

      Last Sold Summary

      • 129 Days On Market

  • /48

    $510,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 3,420 Sq Ft

    27 Ray Hill Rd, Wilmington, VT 05363

    Located in a desirable setting that offers both privacy and the convenience of walking to the quaint village of downtown Wilmington, this spacious country home is full of potential. The home features a large, light-filled kitchen with plenty of space for cooking and gathering. The original post-and-beam barn, which was moved to the property, has been converted into a generous living and dining

    Monica Sumner BHG Masiello Brattleboro

    27 Ray Hill Rd, Wilmington, VT 05363
  • /14

    $240,000

    Sold Jul 17, 2025

    17 Wardon Rd, Putney, VT 05346

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft
    • Built 1974

    Last Sold Summary

    • 4% Below List Price
    • $210/SF
    • 34 Days On Market

    Current Estimated Value $255,928

    Last Listing Agent Jody Graves Berkley & Veller Greenwood Country

    17 Wardon Rd, Putney, VT 05346
    • /32

      Est $577,930

      Not Listed For Sale

      110 Beaver Pond Rd, Dummerston, VT 05301

      • 3 Beds
      • 2.5 Baths
      • 2,280 Sq Ft
      • Built 2008
      110 Beaver Pond Rd, Dummerston, VT 05301

      Last Sold Summary

      • 9 Days On Market

  • /26

    $1,350,000

    • 7,660 Sq Ft

    131,133,141 Green St, Brattleboro, VT 05301

    What an opportunity to own 11 units in 3 separate buildings with a fantastic rental history. Close to downtown, schools, shopping and bus routes. Very well maintained properties with 3 - two bedroom units and 8 one bedroom units. On site laundry for the convenience of tenants. Wonderful features including hardwood floors and large windows for exceptional natural light. Great porches and very

    Susan Bellville Bellville Realty

    131,133,141 Green St, Brattleboro, VT 05301
  • /29

    $495,000

    Sold Nov 21, 2025

    275 Pams Hill Rd, Wardsboro, VT 05355

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 1969

    Last Sold Summary

    • 4% Below List Price
    • $330/SF
    • 59 Days On Market

    Current Estimated Value $497,045

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    275 Pams Hill Rd, Wardsboro, VT 05355
    • /40

      Est $420,646

      Not Listed For Sale

      392 Old Stage Rd, West Halifax, VT 05358

      • 1 Bed
      • 1 Bath
      • 1,416 Sq Ft
      • Built 2001
      392 Old Stage Rd, West Halifax, VT 05358

      Last Sold Summary

      • 6 Days On Market

  • /29

    $469,000

    $46K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,016 Sq Ft

    33D White Oaks Loop Unit 38, Dover, VT 05356

    Owners will consider offers. Nicely updated and uniquely private Timber Creek end-unit townhome with easy access and winter ski trail views. Ideally located directly across from the upper entrance to Mount Snow, Timber Creek offers shuttle service from your front door to the base area, along with convenient on-site management, exterior maintenance, snow removal, landscaping, and more. The

    Adam Palmiter Berkley & Veller Greenwood/Dover

    33D White Oaks Loop Unit 38, Dover, VT 05356
  • /49

    $625,000

    Sold Jan 15, 2026

    956 Old Cheney Rd, West Townshend, VT 05359

    • 2 Beds
    • 2 Baths
    • 2,144 Sq Ft
    • Built 1790

    Last Sold Summary

    • 14% Below List Price
    • $292/SF
    • 141 Days On Market

    Current Estimated Value $613,420

    Last Listing Agent Kim Meeker Southern Vermont Realty Group

    956 Old Cheney Rd, West Townshend, VT 05359

Showing Results 161 - 200, Page 5 of 18

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