30,509

Windham County, VT Homes

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    • /40

      Est $2,725,007 Not Listed For Sale

      • 6 Beds
      • 6.5 Baths
      • 7,088 Sq Ft

      83 Overlook Dr, Dover, VT 05356

      83 Overlook Dr, Dover, VT 05356
  • /32

    $560,000

    • 2 Beds
    • 2 Baths
    • 1,775 Sq Ft

    162 Buttonwood Dr, Brattleboro, VT 05301

    BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

    Dan Normandeau Berkley & Veller Greenwood Country

    162 Buttonwood Dr, Brattleboro, VT 05301
  • /59

    $2,700,000 Sold Nov 19, 2025

    • 5,413 Sq Ft
    • $499/SF
    • 58 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 2024

    1 Sundance Village Loop, Dover, VT 05356

    Welcome to your dream home, a striking 5-bedroom, 6-bathroom Mountain Modern home nestled within the exclusive Sundance Village! A unique opportunity awaits to own a stand-alone house, with direct access to the slopes at Mount Snow and the freshly-upgraded amenities of Seasons on Mount Snow. Imagine walking out your door, steps from the ski trail, coming back for a leisurely lunch, and at day's

    Patricia Fitzpatrick Skihome Realty

    1 Sundance Village Loop, Dover, VT 05356
    • /5

      Est $61,664 Not Listed For Sale

      2 Johnson Hill Rd, Dover, VT 05356

      2 Johnson Hill Rd, Dover, VT 05356
  • /32

    $585,000

    • 2 Beds
    • 2 Baths
    • 1,775 Sq Ft

    161 Buttonwood Dr, Brattleboro, VT 05301

    BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

    Dan Normandeau Berkley & Veller Greenwood Country

    161 Buttonwood Dr, Brattleboro, VT 05301
  • /51

    $425,000 Sold Nov 18, 2025

    • 2,445 Sq Ft
    • $174/SF
    • 74 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1928

    17 Tinker Hill Rd, Guilford, VT 05301

    This one is the right one! So very special, nestled in the countryside just waiting.... So many options to choose from...a first floor main bedroom is perfect for aging in place, an x gen who still lives at home, in-law suite...or...perfect for an Air B&B. The other main bedroom features a walk out to the upper gardens, vaulted ceilings, room for a private getaway or reading nook. Plenty of space

    Christine Lewis Brattleboro Area Realty

    17 Tinker Hill Rd, Guilford, VT 05301
    • /40

      Est $1,215,986 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,536 Sq Ft

      1751 Under the Mountain Rd, South Londonderry, VT 05155

      1751 Under the Mountain Rd, South Londonderry, VT 05155
  • /60

    $579,000

    • 2 Beds
    • 2 Baths
    • 850 Sq Ft

    794 White Rd, Windham, VT 05359

    Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out—new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam

    Erica Reynolds Southern Vermont Realty Group

    794 White Rd, Windham, VT 05359
  • /13

    $301,000 Sold Nov 18, 2025

    • 1,152 Sq Ft
    • $261/SF
    • 1 Day On Market
    • 3 Beds
    • 1 Bath
    • Built 1947

    2380 Guilford Center Rd, Guilford, VT 05301

    Discover classic country living in this inviting 3-bedroom, 1-bath home situated on a generous 5-acre parcel. The property blends simple, comfortable living with wide-open outdoor possibilities — think gardening, large or small livestock, or just relax. Inside, the home greets you with a bright living area, a functional kitchen with ample counter space, and three well-proportioned bedrooms served

    Claire Renaud Berkley & Veller Greenwood Country

    2380 Guilford Center Rd, Guilford, VT 05301
    • /14

      Est $78,098 Not Listed For Sale

      10 Windsor Rd, Bellows Falls, VT 05101

      10 Windsor Rd, Bellows Falls, VT 05101
  • /43

    $599,000

    • 3 Beds
    • 2.5 Baths
    • 2,720 Sq Ft

    58 Buckboard Dr, Dover, VT 05356

    58 Buckboard | Dover, VermontSet on 1.46 private acres with sweeping mountain views, this beautifully updated 3 bedroom, 3 bath home offers a perfect blend of modern style and Vermont warmth.Inside, the heart of the home is the newly renovated kitchen, featuring a center island with quartz countertops, stainless steel appliances, and open shelving. The kitchen flows seamlessly into the

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    58 Buckboard Dr, Dover, VT 05356
  • /25

    $70,000 Sold Nov 18, 2025

    • 1,300 Sq Ft
    • $54/SF
    • 97 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1936

    2418 Back Westminster Rd, Westminster, VT 05158

    Price improvement! Motivated Seller. Embrace the opportunity that awaits you with this cozy Bungalow situated on a lush and level 1.5 acre lot in Westminster, Vermont! This home offers different possibilities for the right buyer to bring their vision and transform this space.You'll have plenty of room to spread out, garden, or simply enjoy the peaceful setting of 1.5 acres that can be

    Lily Gautot Greenwald Realty Group

    2418 Back Westminster Rd, Westminster, VT 05158
    • /9

      Not Listed For Sale

      0 Parker Hill Rd, Bellows Falls, VT 05101

      0 Parker Hill Rd, Bellows Falls, VT 05101
  • /59

    $599,000

    • 3 Beds
    • 2.5 Baths
    • 2,782 Sq Ft

    628 Townshend Rd, Grafton, VT 05146

    One of only two stone houses in the charming town of Grafton, this stately home is a truly special opportunity. Perched on a hill across from the renowned Grafton Cheese Company, the property offers easy access to village amenities and year-round recreation at Grafton Ponds Outdoor Center. Inside, you'll find a spacious and inviting layout: Large front living room with exposed beams, a beautiful

    Jessica Landers Barrett and Valley Associates Inc.

    628 Townshend Rd, Grafton, VT 05146
  • /41

    $299,000 Sold Nov 18, 2025

    • 1,224 Sq Ft
    • $244/SF
    • 11 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1984

    424 Susan Lynn Ln, Wardsboro, VT 05355

    Three bedrooms, two bath home situated on a pleasant one-acre lot with a sizeable back and side yard area. Located in desirable Snow Mountain Farms, (but is NOT part of the association at this time) this home offers hardwood and parkay floors throughout. Primary bedroom has a private three-quarter bath and walkin closet. A second large bedroom on the main floor with a full bath located off of the

    Julie Lowe Lowe's Real Estate, LLC

    424 Susan Lynn Ln, Wardsboro, VT 05355
    • /32

      Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,632 Sq Ft

      85 Route 100, West Dover, VT 05356

      85 Route 100, West Dover, VT 05356
  • /32

    $559,000

    • 3 Beds
    • 3 Baths
    • 2,080 Sq Ft

    9 Greer Ct, Wilmington, VT 05363

    Charming 2007 home with recent renovations nestled in the Chimney Hill community just a short drive from the Mount Snow ski resort, country village of Wilmington, and nearby lakes and amenities. This home sits on a private dead end parcel and has unique privacy and curb appeal. Inside you are treated to a large vaulted great room with expansive windows, exposed natural wood ceilings, and great

    Adam Palmiter Berkley & Veller Greenwood/Dover

    9 Greer Ct, Wilmington, VT 05363
  • /6

    $119,500 Sold Nov 18, 2025

    • Land
    • 2.96 Acres
    • $40,372 per Acre
    • 0 Days On Market

    0 Duke Rd, Newfane, VT 05362

    Have you been searching for the perfect spot to build a home, vacation getaway or invest in Vermont land? Duke Rd is a lovely, quiet dead end road. This almost 3 acre lot on a picturesque road in the charming town of Williamsville offers peace and tranquility while being convenientlysituated near major ski resorts and quaint Vermont villages. There are nearby hiking trails as well as your own

    Kristen Ziter Taylor Brattleboro Area Realty

    0 Duke Rd, Newfane, VT 05362
    • /22

      Not Listed For Sale

      0 Bills Rd, Stratton, VT 05360

      0 Bills Rd, Stratton, VT 05360
  • /3

    $85,900

    • Land
    • 17.41 Acres
    • $4,934 per Acre

    1720 Auger Hole Rd, Marlboro, VT 05344

    First time on the market in nearly 38 years!!! Discover 17.41 acres of peaceful, wooded land in the heart of Marlboro. A scenic brook runs through the property, offering excellent on-site trout fishing and a quiet natural setting. Enjoy close proximity to Hogback Mountain’s 100-mile views, Molly Stark State Park, and the Marlboro Music Festival, along with local favorites like Beer Naked Brewery,

    Raelene Robinson-Garrow Real Broker LLC

    1720 Auger Hole Rd, Marlboro, VT 05344
  • /8

    $87,000 Sold Nov 17, 2025

    • Land
    • 34.77 Acres
    • $2,502 per Acre
    • 7 Days On Market

    00 Fisch Rd, Brattleboro, VT 05301

    AFFORDABLE LAND with several potential building sites, and long-range southerly views possible from the height of the land. Approximately 35 acres of wooded land in southern Vermont. Located on a private dirt road in an area filled with tranquility. It’s very hard to find land that is truly peaceful. Electricity available at road. Minutes to downtown Brattleboro. Easy access to I-91 and Amtrak.

    Dan Normandeau Berkley & Veller Greenwood Country

    00 Fisch Rd, Brattleboro, VT 05301
    • /32

      Not Listed For Sale

      • 6 Beds
      • 2 Baths
      • 2,899 Sq Ft

      432 Route 121, Westminster, VT 05158

      432 Route 121, Westminster, VT 05158
  • /46

    $315,000

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

    4410 Pikes Falls Rd, Jamaica, VT 05343

    This charming cabin in the woods is the perfect retreat for those seeking adventure and tranquility alike. Surrounded by 10.7 acres of forest, it offers a cozy haven just a stone's throw away from the breathtaking Pikes Falls and is n5 minutes to Stratton Mountain, ideal for skiing enthusiasts during the winter months. In warmer weather, the nearby trails beckon hikers and mountain bikers to

    Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

    4410 Pikes Falls Rd, Jamaica, VT 05343
  • /60

    $320,000 Sold Nov 17, 2025

    • 2,579 Sq Ft
    • $124/SF
    • 11 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1929

    11 Culbertson Dr, Brattleboro, VT 05301

    Located in the heart of Brattleboro walking distance to the farmer’s market and the expansive Living Memorial Park, this unique home has many options. Open up one doorway and it could be a 4 bedroom home plus an in-law studio. Or, keep it as 3 separate units – a 3 bedroom home, 1 bedroom apartment, and a very large and elegant studio apartment. It currently functions as an active Air BnB and

    Lisa Friedman Great American Dream Realty

    11 Culbertson Dr, Brattleboro, VT 05301
    • /3

      Est $431,855 Not Listed For Sale

      • Studio
      • 2 Baths
      • 2,863 Sq Ft

      394 Canal St, Brattleboro, VT 05301

      394 Canal St, Brattleboro, VT 05301
  • /34

    $369,000

    • 5 Beds
    • 2 Baths
    • 2,557 Sq Ft

    1501 Sheldon Hill Rd, Wardsboro, VT 05355

    This 5BR/2BA Snow Mountain Farms home offers privacy and easy access to regional recreation. Built for family and friends, and tucked at the end of a quiet road with plenty of parking on a level circular driveway. The great room is anchored by a wood burning stone fireplace with cathedral ceilings, warm wood finishes, and an open flow to the dining area and kitchen. An oversized loft creates

    Karin Hardy Berkshire Hathaway HomeServices Stratton Home

    1501 Sheldon Hill Rd, Wardsboro, VT 05355
  • /32

    $18,000 Sold Nov 14, 2025

    • 608 Sq Ft
    • $30/SF
    • 37 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1998

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

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Unit 111 is available as a 608 sq. ft., sleep 4 quartershare with a spacious private bedroom, cozy kitchen/living/dining area with a pullout couch, a full bath and a private balcony with views of the mountain! The benefits of Grand Summit ownership include the best ski in/out mountain location available at Mount Snow. Use of

    Patricia Fitzpatrick Skihome Realty

    111, Qtr 3, 89 Grand Summit Way, Dover, VT 05356
    • /40

      Est $545,692 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,200 Sq Ft

      1084 Cyrus Rd, Whitingham, VT 05361

      1084 Cyrus Rd, Whitingham, VT 05361
  • /16

    $250,000

    • 3 Beds
    • 1.5 Baths
    • 1,232 Sq Ft

    19 Williams Terrace, Bellows Falls, VT 05101

    Come home to this cozy sun filled house with beautiful hardwood floors and a well thought out floor plan. Built ins, bookshelves and a fireplace are sure to please the next owner! This house is tucked away on a quiet street but also so close the town recreation area. Generous and private backyard with plenty of garden space available.

    Claire Renaud Berkley & Veller Greenwood Country

    19 Williams Terrace, Bellows Falls, VT 05101
  • /27

    $245,000 Sold Nov 14, 2025

    • 756 Sq Ft
    • $324/SF
    • 0 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1967

    8365 Vermont 30, Jamaica, VT 05343

    Quintessential Vermont Log Cabin Seeks New Relationship. I'm an adorable 2 bedroom, 1 bath home, located just 2 short miles from Stratton Mountain. I'm open to a variety of possibilities, including a full-time or seasonal resident. I'd also be a great fit for an investor. What I lack in size, I make up for in character. My open kitchen and living room layout is where I shine, and my cathedral

    TG Glazer Winhall Real Estate

    8365 Vermont 30, Jamaica, VT 05343
    • /37

      Est $417,634 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,444 Sq Ft

      94 Brets Rd, Brattleboro, VT 05301

      94 Brets Rd, Brattleboro, VT 05301
  • /44

    $299,900

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

    10 King St, Bellows Falls, VT 05101

    Discover the ideal balance of privacy and convenience in this welcoming 4-bedroom, 2-bath home in the heart of Bellows Falls. Set on a spacious 1-acre lot, the 1,800-sq-ft interior provides generous room for comfortable everyday living. A private garage and secluded yard offer both practicality and serenity, while the large covered porch invites year-round enjoyment of the outdoors. With

    Floyd Amidon Maple Leaf Realty

    10 King St, Bellows Falls, VT 05101
  • /40

    $650,000 Sold Nov 14, 2025

    • 2,250 Sq Ft
    • $289/SF
    • 63 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1984

    134 Ellis Brook Rd, Dover, VT 05356

    This stunningly renovated 3-bedroom, 3.5-bathroom vacation home with carport, completed in 2021, offers exceptional comfort and style in Dover Hills, near Mount Snow. The remodel includes a brand-new kitchen, bathrooms, flooring, and furniture throughout. Notable upgrades feature an additional 3/4 bathroom, a fully finished basement, and upgraded plumbing, electrical systems, and roof. Modern

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    134 Ellis Brook Rd, Dover, VT 05356
    • /32

      Est $536,114 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,280 Sq Ft

      110 Beaver Pond Rd, Dummerston, VT 05301

      110 Beaver Pond Rd, Dummerston, VT 05301
  • /45

    $439,000

    • 3 Beds
    • 2 Baths
    • 1,564 Sq Ft

    210 Burrington Hill Rd, Whitingham, VT 05361

    Impeccably maintained 2007 residence in like-new condition, offering quality construction and thoughtful design throughout. The home features vinyl siding and a full concrete walk-out basement with high ceilings—an outstanding opportunity for adding 1000+ future finished living space customized to your needs. The main level showcases an open-concept living, kitchen, and dining area with natural

    Jacki Murano Southern Vermont Realty Group

    210 Burrington Hill Rd, Whitingham, VT 05361
  • /41

    $501,000 Sold Nov 14, 2025

    • 3,400 Sq Ft
    • $147/SF
    • 19 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1840

    260 Dover Hill Rd, East Dover, VT 05341

    Beautiful farmhouse on 3 acres w/stone walls, formal gardens, & wraparound covered porch offering stunning three-state easterly views. Located just 6 miles from Mount Snow, this home blends period charm with modern updates. The inviting interior features a spacious family room with wide pine floors, cathedral ceiling, and built-ins. The heart of the home is the expansive kitchen/dining area with

    Robert Doyle Berkley & Veller Greenwood Country

    260 Dover Hill Rd, East Dover, VT 05341
    • /20

      Est $273,758 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,100 Sq Ft

      149 Canal St, Brattleboro, VT 05301

      149 Canal St, Brattleboro, VT 05301
  • /14

    $210,000

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

    00 Vermont Route 100, Jamaica, VT 05343

    Discover the beauty and tranquility of this picturesque wooded parcel—approximately 35 acres—nestled along the serene Deerfield River and spanning the border of Jamaica and Wardsboro. Perfectly situated within easy reach of Mount Snow, Stratton, and Bromley, the property offers convenient access to year-round recreation while preserving the sense of peace and privacy that only a large forested

    Patrice Schneider Southern Vermont Realty Group

    00 Vermont Route 100, Jamaica, VT 05343
  • /20

    $11,000 Sold Nov 14, 2025

    • 673 Sq Ft
    • $16/SF
    • 90 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1998

    122, Qtr 1 89 Grand Summit Way, Dover, VT 05356

    TRAILSIDE! A great and affordable opportunity to own the best location to be on the Mount Snow ski trails. This unit boasts a queen size Murphy bed, a queen size sofa, kitchenette and full bath. The bedroom has a queen size bed and a deck. Enjoy being at the best location for skiing and being able to enjoy all the amenities offered by the Grand Summit. Heated pool, sauna, steam room, gym, spa,

    Sheila Joyce-Albano Skihome Realty

    122, Qtr 1 89 Grand Summit Way, Dover, VT 05356
    • /40

      Est $416,789 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 1,416 Sq Ft

      392 Old Stage Rd, West Halifax, VT 05358

      392 Old Stage Rd, West Halifax, VT 05358

Showing Results 121 - 160, Page 4 of 18

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