30,507

Windham County, VT Homes

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  • /36

    $499,000

    • Land
    • 41 Acres
    • $12,171 per Acre

    706 Vt Route 100, Stratton, VT 05360

    Exceptional New Offering! Rare 41± acres in Stratton with extraordinary 180 +/- long-range mountain views, improvements, base camp, driveway, clearings, trails, wildlife, and a substantial WOW factor. All for approx. $12,000/acre. A short drive in from paved Route 100, before the land rises further in elevation, sits the rustic 1-bed base camp overlooking open field and multiple ski

    Jacki Murano Southern Vermont Realty Group

    706 Vt Route 100, Stratton, VT 05360
  • /41

    $312,000 Sold Nov 14, 2025

    • 1,055 Sq Ft
    • $296/SF
    • 9 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1936

    79 Missing Link Rd, Bellows Falls, VT 05101

    Waterfront four season vacation cottage complete with frontage along the Williams River and direct deep-water access to the Connecticut River. Enjoy swimming, boating, fishing and bird watching from your beach. Quonset hut provides storage for your Kayaks and garden equipment, which are included. Engineered for ease of access, stairs lead to a path to the river, with platforms to relax and

    Heidi Bernier Berkley & Veller Greenwood Country

    79 Missing Link Rd, Bellows Falls, VT 05101
    • /4

      Est $484,018 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,958 Sq Ft

      255 Minard Rd, Putney, VT 05346

      255 Minard Rd, Putney, VT 05346
  • /24

    $389,000

    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft

    115 Country Hill, Brattleboro, VT 05301

    This lovely West Brattleboro cape is located on a quiet cul-de-sac right on the outskirts of town. Built in 2002 with a spacious design, you enter through the oversized two-car garage into a contemporary kitchen. Features include granite countertops, tile floors, an elegant backsplash, and a door leading to a private terrace, ideal for family gatherings or entertaining. The first floor has

    Kristen Ziter Taylor Brattleboro Area Realty

    115 Country Hill, Brattleboro, VT 05301
  • /22

    $132,000 Sold Nov 14, 2025

    • Land
    • 3.48 Acres
    • $37,931 per Acre
    • 32 Days On Market

    Lot 5 Hope Rd, Newfane, VT 05345

    Buildable Acreage with permits in place on the West River! This is your chance to own a true waterfront lot with clearing, underground power already in place, a 4-bedroom septic permit, and ample river frontage to call your own. Build your dream home on this private cul-de-sac with only 4 other property owners ( currently 2 other homes). Step out your back door with your swimsuit on and your

    Jacki Murano Southern Vermont Realty Group

    Lot 5 Hope Rd, Newfane, VT 05345
    • /40

      Est $592,000 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 2,348 Sq Ft

      129 Adams Hill Rd Unit 27, South Newfane, VT 05351

      129 Adams Hill Rd Unit 27, South Newfane, VT 05351
  • /33

    $229,000

    • 3,302 Sq Ft

    36 Barker St, Town of Rockingham, VT 05101

    This charming three-unit property in the heart of Bellows Falls, VT, offers a rare combination of historic character and modern appeal. With its exterior freshly painted in November 2025, the building exudes curb-appeal and care. Inside, the first-floor unit features three bedrooms and a full bath—perfect for a family or long-term tenant—while the second and third-floor units each offer two

    Rob Weltz Barrett and Valley Associates Inc.

    36 Barker St, Town of Rockingham, VT 05101
  • /26

    $299,600 Sold Nov 14, 2025

    • 1,370 Sq Ft
    • $219/SF
    • 109 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1965

    749 Vermont Route 100, Wardsboro, VT 05355

    This charming, updated 3-bedroom, 2-bath Cape style home sits on 0.17 acres in the heart of Vermont's ski country. Filled with natural light, the warm and inviting interior features a main-level bedroom, while two additional upstairs bedrooms are perfect for guests. After a day on the slopes, unwind by the cozy gas fireplace. Enjoy your morning coffee on the covered porch, or spend evenings

    Cassandra Ehrlich BHG Masiello Brattleboro

    749 Vermont Route 100, Wardsboro, VT 05355
    • /31

      Est $348,024 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,400 Sq Ft

      47 Sherwood Cir, Brattleboro, VT 05301

      47 Sherwood Cir, Brattleboro, VT 05301
  • /27

    $425,000

    • 5 Beds
    • 3 Baths
    • 1,440 Sq Ft

    135 Overlook Dr, Londonderry, VT 05148

    Investment opportunity! This beautiful ski country compound offers 3 streams of rental income, or a home where you can enjoy sweeping views of the West River Valley just minutes away from Magic Mountain skiing and a surprising array of amenities in Londonderry’s town center. A barn apartment over a garage with a 3/4 bath, and an upstairs and downstairs unit with a full bath each, are all equipped

    Zachary Zupan EXP Realty

    135 Overlook Dr, Londonderry, VT 05148
  • /37

    $419,000 Sold Nov 13, 2025

    • 2,900 Sq Ft
    • $144/SF
    • 5 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1982

    42 Newfane Hill Rd, Newfane, VT 05345

    Privately set on over 10 acres, this expanded Cape offers space, character, and country charm. A flat rear yard and garden cottage add to the appeal, while a 2-car under garage provides direct access to the basement. Inside, the home is light-filled with large windows, cathedral ceilings, exposed beams, and an expansive front deck for outdoor enjoyment. The inviting mudroom with built-in bench

    Robert Doyle Berkley & Veller Greenwood Country

    42 Newfane Hill Rd, Newfane, VT 05345
    • /33

      Est $345,394 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,756 Sq Ft

      84 Brookline Rd, Athens, VT 05143

      84 Brookline Rd, Athens, VT 05143
  • /34

    $389,900

    • 2 Beds
    • 2 Baths
    • 1,076 Sq Ft

    295 Stratton Arlington Rd, West Wardsboro, VT 05360

    Beautifully renovated 2-bedroom, 2-bath cottage on 1.9 acres in Stratton. Ideally located just minutes from both Mount Snow and Stratton ski areas, with the Stratton Recreation Center conveniently down the road. Enter through the mudroom into a bright, open-concept kitchen and dining space featuring a cozy woodstove and 4 skylights. The living room is spacious with a mini split and also includes

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    295 Stratton Arlington Rd, West Wardsboro, VT 05360
  • /31

    $545,925 Sold Nov 13, 2025

    • 1,500 Sq Ft
    • $364/SF
    • 8 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1968

    217 Magic Cir, Londonderry, VT 05148

    Just steps from the lift, this is one of the closest single-family homes to Magic Mountain’s base area. Meticulously maintained and thoughtfully updated, it’s a perfect year-round retreat. Upgrades over the years include a newer roof, interior/exterior paint, heat pump with A/C, Wi-Fi thermostats, and a renovated kitchen with modern appliances and an under-bar mini fridge. The open

    MaryKate Grey Stratton Real Estate

    217 Magic Cir, Londonderry, VT 05148
    • /18

      Est $368,116 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,302 Sq Ft

      7 Center Rd, Wilmington, VT 05363

      7 Center Rd, Wilmington, VT 05363
  • /22

    $395,000

    • 4 Beds
    • 4 Baths
    • 2,182 Sq Ft

    39 Williston St, Brattleboro, VT 05301

    Take a moment to admire this charming Victorian townhouse, nestled on a quiet one-way street. Delightfully landscaped and renovated, the owner has taken care to modernize (heating system, wiring, plumbing, roof, bathrooms, etc.) without compromising the character & charm we all love. Beautiful maple woodwork and lofty ceilings add to the lovely turn-of-the-century details. With three separate

    Christine Lewis Brattleboro Area Realty

    39 Williston St, Brattleboro, VT 05301
  • /39

    $1,250,000 Sold Nov 12, 2025

    • 4,226 Sq Ft
    • $296/SF
    • 4 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1967

    400 Stowe Hill Rd, Wilmington, VT 05363

    Experience exceptional and elegant Vermont living at this contemporary retreat perched on just over 12 picturesque acres with breathtaking views of Haystack Mountain. This thoughtfully crafted home features quality materials throughout, with striking cedar exterior, remote-controlled shades, and a metal standing seam roof. The main level offers easy living with two en-suite bedrooms, plus two

    Erica Reynolds Southern Vermont Realty Group

    400 Stowe Hill Rd, Wilmington, VT 05363
    • /35

      Est $336,134 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,783 Sq Ft

      31 Brook St, Whitingham, VT 05361

      31 Brook St, Whitingham, VT 05361
  • /3

    $60,000

    • Land
    • 1.1 Acres
    • $54,545 per Acre

    63 Villager Loop, Dover, VT 05356

    Lovely wooded building site not far from the Mount Snow ski resort, nearby lakes, villages, shopping, and dining. View potential and easy access off a paved road, with a large corner lot location, looking to the west over the ski mountains and sunsets.

    Adam Palmiter Berkley & Veller Greenwood/Dover

    63 Villager Loop, Dover, VT 05356
  • /11

    $62,500 Sold Nov 12, 2025

    • Land
    • 1 Acre
    • $62,500 per Acre
    • 94 Days On Market

    116 Newcomb Rd, Westminster, VT 05158

    Discover the potential of this 1-acre parcel nestled in the heart of picturesque Westminster, Vermont. Set on a quiet country road and framed by mature trees, this level lot offers a tranquil setting with a brook gently meandering along the northern boundary—an ideal natural feature for those seeking peace and privacy. The property includes an existing house, a few garage bays, and multiple

    TG Glazer Winhall Real Estate

    116 Newcomb Rd, Westminster, VT 05158
    • /34

      Est $239,247 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,572 Sq Ft

      83 Goldies Rd, Putney, VT 05346

      83 Goldies Rd, Putney, VT 05346
  • /25

    $349,000 Open Sat 3PM - 5PM

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

    337 Handle Rd Unit Pines K, West Dover, VT 05356

    Welcome to this beautifully updated two bedroom, two-bathroom condo in the desirable upper Snow Tree community. The home is perfectly positioned to capture incredible mountain views and the true essence of Mount Snow base area living. Step inside to find a bright, inviting interior featuring new efficient windows, a cozy gas fireplace, and beautiful cathedral ceiling that enhances the spacious

    Melissa Ellis Southern Vermont Realty Group

    337 Handle Rd Unit Pines K, West Dover, VT 05356
  • /48

    $790,000 Sold Nov 10, 2025

    • 2,150 Sq Ft
    • $367/SF
    • 4 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2008

    33 Fore Seasons Dr Unit N1, Wilmington, VT 05363

    This well-cared-for townhouse in Haystack Highlands offers a spacious layout with 3 bedrooms and 3 baths across two levels, plus untapped potential in the lower level. The main floor features a welcoming foyer, a mudroom currently used as an office, a bright living room with a striking fieldstone wood-burning fireplace, and an open kitchen/dining area. From the dining space, step out to the

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    33 Fore Seasons Dr Unit N1, Wilmington, VT 05363
    • /34

      Est $376,965 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,600 Sq Ft

      51 Apple Blossom Ln, Grafton, VT 05146

      51 Apple Blossom Ln, Grafton, VT 05146
  • /38

    $475,000

    • Land
    • 133.1 Acres
    • $3,569 per Acre

    40 E Putney Brook Rd, Putney, VT 05346

    Awesome 133± Acre Country Parcel in Putney, Vermont. A rare opportunity to own 133± acres of picturesque Vermont land in highly desirable Putney. This large country parcel offers multiple access points, including generous frontage on a major road as well as two unpaved roads. Existing logging roads weave through the property, leading to several clearings ideal for building, recreation, or

    Geralyn Donohue Engel & Völkers Okemo

    40 E Putney Brook Rd, Putney, VT 05346
  • /60

    $320,000 Sold Nov 10, 2025

    • 1,150 Sq Ft
    • $278/SF
    • 105 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1970

    108 Spruce Grove Rd Unit M286, Wilmington, VT 05363

    This house sits on a lot that is surrounded by common land so it feels very secluded and private. Newer septic, roof, and main level flooring, and the prior owner did a lot of custom wood paneling with built-ins, and creative decorating which add to its charm. The main level has a mudroom entry with laundry and storage space, full bath, kitchen with open shelving above and cabinets below, newer

    Sigrid Pickering Chimney Hill Realty

    108 Spruce Grove Rd Unit M286, Wilmington, VT 05363
    • /26

      Est $321,112 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,948 Sq Ft

      240 S Main St, Brattleboro, VT 05301

      240 S Main St, Brattleboro, VT 05301
  • /4

    $160,000

    • Land
    • 9.3 Acres
    • $17,204 per Acre

    00 E Putney Brook Rd, Putney, VT 05346

    Located on E. Putney Brook Rd., approx. 2.5 miles from Putney Village, this beautiful, wooded 9+ ac property offers a desirable place to build. Bring your own building plans, power is nearby, and septic design is available. Clear a prime building site on level plateau and surround your home with mature woodlands. This county location offers easy access to orchards, farmstands for local produce,

    Heidi Bernier Berkley & Veller Greenwood Country

    00 E Putney Brook Rd, Putney, VT 05346
  • /9

    $70,000 Sold Nov 10, 2025

    • Land
    • 3.1 Acres
    • $22,581 per Acre
    • 110 Days On Market

    0 E Orchard St Unit 5047716, Brattleboro, VT 05301

    A rare opportunity to purchase a lot in a highly desirable Brattleboro neighborhood. This 3+ acre wooded parcel features a mature pine forest with additional hardwoods intermixed, stonewalls and even a small stream. It's the location that makes this property unique. Just up the road from the Brattleboro Country Club on a quiet street that gives quick access to all that Brattleboro and the

    Bill Hickok Berkley & Veller Greenwood Country

    0 E Orchard St Unit 5047716, Brattleboro, VT 05301
    • /14

      Est $231,014 Not Listed For Sale

      • Studio
      • 2 Baths
      • 2,708 Sq Ft

      202 Canal St, Brattleboro, VT 05301

      202 Canal St, Brattleboro, VT 05301
  • /55

    $1,345,000

    • 3 Beds
    • 2 Baths
    • 2,546 Sq Ft

    135 Fred Houghton Rd, Putney, VT 05346

    This one-of-a-kind Vermont property offers three dwellings on 5.6 acres - each blending elevated aesthetics, thoughtful design, and a true connection to nature. The 2011 main house features an open layout and handcrafted finishes throughout. The kitchen boasts soapstone countertops and custom cherry cabinetry. A very special wood-fired masonry heater anchors the living space and a spacious

    Benjamin Cote EXP Realty

    135 Fred Houghton Rd, Putney, VT 05346
  • /20

    $676,100 Sold Nov 10, 2025

    • 2,500 Sq Ft
    • $270/SF
    • 9 Days On Market
    • 6 Beds
    • 2 Baths
    • Built 1969

    125 Valley View Rd, Dover, VT 05356

    Welcome to “Winterfell” a secluded six-bedroom home in the authentic and increasingly rare A-frame, chalet-style. Vaulted ceilings and a dramatic wall of windows frame the surrounding forest, with an open floor plan including a living room with wood-burning fireplace and a separate den for games and casual relaxation. An expansive deck with hot tub extends the living space outdoors. Just five

    Jason Saphire www.HomeZu.com

    125 Valley View Rd, Dover, VT 05356
    • /38

      Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,950 Sq Ft

      773 Guilford St, Brattleboro, VT 05301

      773 Guilford St, Brattleboro, VT 05301
  • /31

    $2,100,000

    • 7 Beds
    • 4 Baths
    • 4,256 Sq Ft

    121 Fannie Hill Dr, Wilmington, VT 05363

    Stunning contemporary chalet completely renovated in 2016 and located adjacent to the base of the Hermitage Club private ski resort. This gorgeous home sits on a private lot with direct snowmobile trail access, easy access to the ski trails, and direct to the clubhouse. Just a short drive into the village of Wilmington and the area's tremendous lakes. Thanks to the complete overhaul and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    121 Fannie Hill Dr, Wilmington, VT 05363
  • /31

    $499,000 Sold Nov 07, 2025

    • 1,568 Sq Ft
    • $318/SF
    • 67 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2016

    321 Leonard Rd, Dummerston, VT 05301

    Get ready for your new favorite property. Located in highly-desirable West Dummerston, just 10 minutes from downtown Brattleboro, this energy-efficient Unity high performance home is waiting for you. It’s a very cozy 3-bedroom, 2 full bathroom single-level home on 0.88 acres. Built of pre-fabricated components in factory-controlled conditions, this house is just some solar panels away from being

    John Hatton Berkley & Veller Greenwood Country

    321 Leonard Rd, Dummerston, VT 05301
    • /25

      Est $276,458 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,106 Sq Ft

      8 Route 35, Athens, VT 05143

      8 Route 35, Athens, VT 05143
  • /28

    $285,000

    • 2 Beds
    • 1 Bath
    • 903 Sq Ft

    1555 W River Rd, Dummerston, VT 05301

    Open House 11/15 - 12pm-2pm Welcome home to this inviting 2-bedroom, 1-bath Cape on scenic West River Road. Perfectly located just a short drive to downtown Brattleboro’s shops, restaurants, and local conveniences—just over a quarter mile to West River Park and about 30 minutes to Mount Snow—this home offers the ideal blend of country charm and everyday comfort. Set on a beautiful .6-acre lot

    Morriah Adams BHG Masiello Brattleboro

    1555 W River Rd, Dummerston, VT 05301
  • /34

    $1,250,000 Sold Nov 07, 2025

    • 5,153 Sq Ft
    • $243/SF
    • 119 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1991

    15 Springhill Rd, Dover, VT 05356

    Enjoy perfect Vermont styling in this spacious and functional home just a short drive to the Mount Snow ski resort, nearby lakes, and villages. This private location is nestled just off the Mount Snow golf course in the Deerfield Valley, and easily accessible from a paved road. The home has been fully renovated with no expense spared. Features include an open concept floor plan with expansive

    Adam Palmiter Berkley & Veller Greenwood/Dover

    15 Springhill Rd, Dover, VT 05356
    • /27

      Est $319,204 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,941 Sq Ft

      239 Breezy Acres Dr, Vernon, VT 05354

      239 Breezy Acres Dr, Vernon, VT 05354
  • /43

    $299,000

    • 6 Beds
    • 5 Baths
    • 3,942 Sq Ft

    2072 N Main St, Londonderry, VT 05148

    This is your chance to own in downtown Londonderry! You have the option of commercial, residential or BOTH. One unit is currently set up for residential use with living area and 3/4 bath on the first level and three bedrooms and full bath on the second floor. The second unit has been used for commercial use in the past with open space and 1/2 bath on the first floor with 3 rooms and 2 full baths

    Catherine Cairns Maple Leaf Realty

    2072 N Main St, Londonderry, VT 05148

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