30,507

Windham County, VT Homes

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  • /44

    $1,500,000

    • 5 Beds
    • 4 Baths
    • 4,099 Sq Ft

    314 Putnam State Forest Rd, Grafton, VT 05146

    Grafton Lodge is a striking five-bedroom, four-bathroom timber frame retreat set on 72 acres of complete privacy, directly bordering the 146-acre Putnam State Forest. Built in 2022, this 4,000+ sq ft home blends timeless craftsmanship with modern comforts, featuring wide hemlock floors, exposed beams, and walls of windows that invite the natural surroundings inside.At the heart of the home is

    Debra Staniscia Four Seasons Sotheby's Int'l Realty

    314 Putnam State Forest Rd, Grafton, VT 05146
  • /23

    $231,500 Sold Oct 17, 2025

    • 640 Sq Ft
    • $362/SF
    • 80 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1982

    9B Snow Mountain Village Unit 142, Dover, VT 05356

    GORGEOUS VIEWS OF MOUNT SNOW from this bright, airy one-bedroom, top-floor, corner condo in Snow Mountain Village, just minutes to the base area! Recent updates to the building include a new roof and new skylights. The interior has been tastefully updated with wood-tone vinyl flooring, plush bedroom carpet, all new LG appliances, quartz countertop and kitchen cabinets, new bathroom vanity, new

    Patricia Fitzpatrick Skihome Realty

    9B Snow Mountain Village Unit 142, Dover, VT 05356
    • /40

      Est $435,548 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,158 Sq Ft

      280 Davidson Hill Rd, Westminster, VT 05158

      280 Davidson Hill Rd, Westminster, VT 05158
  • /60

    $415,000

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

    58-60 Frost Place, Brattleboro, VT 05301

    OPEN HOUSE 11/30 11am-1 PM This turnkey income generator is now move in ready! One side is vacant and ready for your plans, the other has a successful Airbnb rental history and was completely renovated in 2018. Brand new dishwasher on the rental unit and 2025 hot water heater. Both have in-unit washer& dryer. Enter through the thoughtfully crafted mudroom with generous built-in storage. The

    Lily Gautot Greenwald Realty Group

    58-60 Frost Place, Brattleboro, VT 05301
  • /27

    $365,000 Sold Oct 17, 2025

    • 706 Sq Ft
    • $517/SF
    • 5 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1980

    908 Stickney Brook Rd, Dummerston, VT 05301

    Escape to peace and quiet with this rare 37.7-acre property, offering the perfect blend of a large open field and wooded privacy. Nestled in a serene natural setting, this charming cabin is ideal for those seeking a retreat from the everyday hustle. The land features a spacious level field excellent for gardening, hobby farming, or simply soaking up the wide-open views, balanced by mature woods

    Wilma Skovinski Berkley & Veller Greenwood Country

    908 Stickney Brook Rd, Dummerston, VT 05301
    • /30

      Est $268,710 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,100 Sq Ft

      97 Mountain Dr, Putney, VT 05346

      97 Mountain Dr, Putney, VT 05346
  • /60

    $5,900,000

    • 4 Beds
    • 8 Baths
    • 16,736 Sq Ft

    1950 Collins Rd, Brattleboro, VT 05301

    Exceptional 177+ Acre Estate with Luxury Log Home, Event Venue & Craft Beverage Facilities. Experience unmatched luxury and opportunity on this remarkable 177+ acre estate. Featuring an 8,000+ sq ft timber frame log home, a 7,100 sq ft finished event venue, and on-site winery, craft brewery, and champagne-making facilities, this turn-key property is ideal as a private residence, retreat, or

    Margretta Fischer Wohler Realty Group

    1950 Collins Rd, Brattleboro, VT 05301
  • /33

    $527,500 Sold Oct 17, 2025

    • 2,504 Sq Ft
    • $211/SF
    • 18 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2005

    19 Titus Farm Rd, Wilmington, VT 05363

    The epitome of a Vermont country home, yet just outside the village of Wilmington, down the road from Lake Raponda, and a short drive the Mount Snow ski resort. This lovely 5+ acre property has a beautiful gurgling brook running through it, gorgeous stone work including old walls and an old stone bridge, trails through the pastoral setting, fire pit area, perennial gardens, and utter privacy.

    Adam Palmiter Berkley & Veller Greenwood/Dover

    19 Titus Farm Rd, Wilmington, VT 05363
    • /34

      Est $558,084 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,488 Sq Ft

      112 Kent Rd, Wardsboro, VT 05355

      112 Kent Rd, Wardsboro, VT 05355
  • /52

    $1,725,000

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

    122 Sunbowl Ridge Rd, Stratton, VT 05360

    Solstice has long been considered the very finest townhome development at Stratton Mountain. With an unparalleled slope side location and private amenities such as heated pool and tub , private shuttle service. This four bedroom four bath townhome is the ultimate ski and summer getaway. Beautifully redone. One car heated garage, family room.

    John Sikes Stratton Real Estate

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

    $62,500 Sold Oct 16, 2025

    • Land
    • 10 Acres
    • $6,250 per Acre
    • 33 Days On Market

    0 Stratton Hill Rd, Marlboro, VT 05351

    Located on picturesque and remote Stratton Hill Road (accessible from Lower Dover Road in Marlboro or Adams Brook Road in Newfane), this lot is bordered by Worden stream and offers potential south-facing views. A perc test and application for an on-site septic system in a Conservation District was filed with the town of Marlboro in 1985.

    Victoria Woods Brattleboro Area Realty

    0 Stratton Hill Rd, Marlboro, VT 05351
    • /16

      Est $240,425 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 874 Sq Ft

      3129 Route 100, Wardsboro, VT 05355

      3129 Route 100, Wardsboro, VT 05355
  • /38

    $639,000

    • 3 Beds
    • 2.5 Baths
    • 3,113 Sq Ft

    1382 Grassy Brook Rd, Brookline, VT 05345

    Beautiful Brookline! Lovingly developed by the current owners over the past 40 years, this remarkable property offers a rare opportunity—ideal for a builder, contractor, skier, snowmobiler, or anyone seeking space for equipment storage. Arrive by crossing a charming stream and following a gentle rise to the main home, which includes a one-car attached garage in the basement. Inside, the finished

    Thomas Dahlin Berkley & Veller Greenwood Country

    1382 Grassy Brook Rd, Brookline, VT 05345
  • /53

    $360,000 Sold Oct 14, 2025

    • 1,250 Sq Ft
    • $288/SF
    • 166 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1985

    5 Black Bear Ln Unit 5F, Dover, VT 05356

    Turnkey Townhouse in Sought-After Bears Crossing at Mount Snow, Vermont! Don’t miss this rare opportunity to own a beautifully updated end unit in one of the best-maintained buildings in Bears Crossing! Perfectly situated just steps from the clubhouse, heated pool, tennis and pickleball courts, and the dedicated Moover shuttle bus to Mount Snow—this location offers both convenience and

    Steve Goldfarb Deerfield Valley Real Estate

    5 Black Bear Ln Unit 5F, Dover, VT 05356
    • /28

      Est $398,599 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,052 Sq Ft

      2599 Route 100, Wardsboro, VT 05355

      2599 Route 100, Wardsboro, VT 05355
  • /29

    $649,000

    • 5 Beds
    • 3.5 Baths
    • 2,706 Sq Ft

    916 Wiswall Hill Rd, Townshend, VT 05353

    Escape to the peace and beauty of Townshend, Vermont, where this spacious 5-bedroom home offers the perfect blend of privacy, comfort, and craftsmanship. Located on a publicly maintained dead-end road, the property enjoys a quiet, secluded country setting while still providing the reassurance of year-round access. Thoughtfully designed and well-built, the home welcomes you with warmth and

    Mike Masters Four Seasons Sotheby's Int'l Realty

    916 Wiswall Hill Rd, Townshend, VT 05353
  • /51

    $915,000 Sold Oct 14, 2025

    • 3,100 Sq Ft
    • $295/SF
    • 63 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2002

    111 Cooper Hill Rd, Dover, VT 05341

    Perched atop scenic Cooper Hill in Dover, Vermont, this welcoming 3-bedroom, 3-bath home is set on over 10 acres with sweeping Mountain views and unforgettable sunrises. The spacious open concept living area and kitchen are ideal for gathering, featuring wood floors, abundant natural light, and a cozy wood burning stove that anchors the space. A generous first floor primary suite offers comfort

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    111 Cooper Hill Rd, Dover, VT 05341
    • /33

      Est $572,140 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,400 Sq Ft

      456 Bills Rd, Wardsboro, VT 05355

      456 Bills Rd, Wardsboro, VT 05355
  • /58

    $32,000

    • 1 Bed
    • 2 Baths
    • 771 Sq Ft

    123/125 Qtr 4 Grand Summit Way Unit 123/125, Qtr 4, Dover, VT 05356

    Experience the ultimate in flexibility and mountain living with this deeded quartershare at the Grand Summit Hotel. Enjoy 13 weeks of vacation annually—one week every 28 days—on a rotating basis. Use it, rent it, or trade it for other destinations! This spacious mountain-side lockout unit, the closest unit to the back door to the slopes, comfortably sleeps 8. Unit 123 is a hotel room with 2

    Donna Brown Skihome Realty

    123/125 Qtr 4 Grand Summit Way Unit 123/125, Qtr 4, Dover, VT 05356
  • /40

    $224,900 Sold Oct 10, 2025

    • 848 Sq Ft
    • $265/SF
    • 96 Days On Market
    • 1 Bed
    • 2 Baths
    • Built 1984

    11F Snow Tree Ln Unit F, Dover, VT 05356

    Be in the heart of the action at the base area of Mount Snow in this light-filled 1-bedroom, 2-bath end unit in the sought-after Snowtree community. Step out your door, stroll across the bridge and parking lot, and hop on the Magic Carpet lift—no need to drive. This well-designed end unit offers extra windows for abundant natural light, a smart floor plan, generous closet space, and two cozy

    Chad Lackey Deerfield Valley Real Estate

    11F Snow Tree Ln Unit F, Dover, VT 05356
    • /13

      Est $133,022 Not Listed For Sale

      • 3 Beds

      70 Broad Brook Rd, Vernon, VT 05354

      70 Broad Brook Rd, Vernon, VT 05354
  • /28

    $399,000

    • 2 Beds
    • 2.5 Baths
    • 1,558 Sq Ft

    339G Handle Rd Unit Elms G, Dover, VT 05356

    This unique two-level condo has been tastefully updated, featuring a 2-bedroom, 2.5-bath condo in the desirable Snow Tree community, which offers the perfect blend of comfort, style, and convenience—just moments from the slopes of Mount Snow!Step inside the entry level and enjoy an open-concept floor plan ideal for entertaining or relaxing after a day on the mountain. The renovated kitchen

    Patricia Fitzpatrick Skihome Realty

    339G Handle Rd Unit Elms G, Dover, VT 05356
  • /58

    $475,000 Sold Oct 10, 2025

    • 2,316 Sq Ft
    • $205/SF
    • 6 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1981

    1923 N Hill Rd, Chester, VT 05143

    Escape to your own private Vermont retreat in this classic 1980s chalet set on 13+ acres in a serene, park-like setting. Tucked back from the road yet convenient to local amenities, the home offers three levels of living space with five bedrooms and three baths. The lower level features a second kitchen and living area perfect for guests or young adults. In summer, enjoy the best of country

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    1923 N Hill Rd, Chester, VT 05143
    • /35

      Est $283,550 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,152 Sq Ft

      63 Washburn Way, Vernon, VT 05354

      63 Washburn Way, Vernon, VT 05354
  • /46

    $992,000

    • 4 Beds
    • 4.5 Baths
    • 3,100 Sq Ft

    33 Carinthia Rd, Dover, VT 05356

    3000+ Sq ft, 4 beds plus den, 4.5 baths, 3 fireplaces and an attached garage all in the Carinthia base area of Mount Snow Ski Resort!! This 4-bedroom, 4.5-bath home offers a versatile layout with multiple en-suite bedrooms, 3 wood burning fireplaces, and a sauna, just steps from the slopes. The main level showcases a spacious sunken living room with cathedral ceilings and soaring brick fireplace,

    Jacki Murano Southern Vermont Realty Group

    33 Carinthia Rd, Dover, VT 05356
  • /25

    $210,000 Sold Oct 10, 2025

    • 800 Sq Ft
    • $262/SF
    • 0 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1944

    402 Butternut Hill Rd, Guilford, VT 05301

    Charming one-bedroom cottage sitting on a gentle hill with a lovely view of Wantastiquet. Located in Guilford, it presents the best of both worlds: a peaceful rural setting with quick access to all Brattleboro has to offer and to I-91N/S. The home offers a full kitchen, dining room, living-room and full-bath. The footprint of the 800-sq ft home provides surprisingly generous-sized rooms. New

    Laura D'Angelo Berkley & Veller Greenwood Country

    402 Butternut Hill Rd, Guilford, VT 05301
    • /40

      Est $206,529 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,120 Sq Ft

      550 Newton Rd, Vernon, VT 05354

      550 Newton Rd, Vernon, VT 05354
  • /20

    $99,500

    • Land
    • 10.27 Acres
    • $9,688 per Acre

    0 Theresa Ln, Wilmington, VT 05363

    This is a rare 10.27 acre offering located in the pastoral town of Wilmington, Vermont. Featuring approximately 8 acres open field, stone walls, cherry trees, potential views of the windmills with clearing, and the Beaver Brook running through the lower section, this property offers privacy and beauty. In addition, the land is close to Mount Snow and the Hermitage Club, plus provides easy access

    Lisa Mirando Deerfield Valley Real Estate

    0 Theresa Ln, Wilmington, VT 05363
  • /45

    $245,000 Sold Oct 10, 2025

    • 1,586 Sq Ft
    • $154/SF
    • 71 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1960

    2277 Vermont 30, Jamaica, VT 05343

    Meander down the winding private drive and “LO AND BEHOLD” an enchanting country cottage nestled on a serene 4.8 acres awaits you! This quaint 3-bedroom, 1-bath home is brimming with potential. Inside, you'll find wideboard pine flooring in the dining and living rooms, 2 woodstoves, and an additional den area. In 2024, SEVCA conducted an energy service, enhancing the home with spray foam

    Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

    2277 Vermont 30, Jamaica, VT 05343
    • /39

      Est $475,592 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,195 Sq Ft

      131 Woodland Rd, Vernon, VT 05354

      131 Woodland Rd, Vernon, VT 05354
  • /22

    $199,000

    • Land
    • 3.6 Acres
    • $55,278 per Acre

    00 Lake Hill Rd Unit "Spring Lot", Whitingham, VT 05361

    Rare opportunity to own the “Spring Lot,” a beautiful 3.6-acre building site overlooking private Laurel Lake in Southern Vermont. This peaceful 17-acre lake is reserved exclusively for landowners—no motorboats allowed—perfect for kayaking, canoeing, fishing, and swimming, with the ability to add your own private dock. With preliminary soil testing showing positive results, utilities at the road,

    Chad Lackey Deerfield Valley Real Estate

    00 Lake Hill Rd Unit "Spring Lot", Whitingham, VT 05361
  • /24

    $584,000 Sold Oct 10, 2025

    • 2,625 Sq Ft
    • $222/SF
    • 93 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1990

    282 Pams Hill Rd, Wardsboro, VT 05355

    As Vermonty as you can get! Located conveniently between Mount Snow and Stratton, for easy access to skiing, shopping, lakes, and summer fun, sits this idyllic log style chalet with tremendous personal use or rental potential. The home sits on a private parcel not far from the Snow Mountain Farms amenities including indoor pool and tennis court. There is ample parking thanks to a cul de sac

    Adam Palmiter Berkley & Veller Greenwood/Dover

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

      Est $470,919 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 3,551 Sq Ft

      19 Southern Heights Dr, Vernon, VT 05354

      19 Southern Heights Dr, Vernon, VT 05354
  • /60

    $2,150,000

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

    18 New England Power Rd, Wilmington, VT 05363

    This extraordinary luxury farmhouse has been masterfully remodeled by the current owners, offering a refined retreat abutting Vermont’s Green Mountain Forest. Every inch has been reimagined with high-end finishes, from the new roof to custom details throughout, creating a turnkey sanctuary that blends timeless charm with modern sophistication. A beautiful sunroom invites relaxation with abundant

    Samantha Decker Deerfield Valley Real Estate

    18 New England Power Rd, Wilmington, VT 05363
  • /44

    $790,000 Sold Oct 10, 2025

    • 3,102 Sq Ft
    • $255/SF
    • 15 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1982

    1410 Haven Hill Rd, South Londonderry, VT 05155

    This beautiful Timber frame home on an 8.1 acre lot is located a few miles from the base of Stratton, Bromley, and Magic Mountain making it a versatile investment. Whether a seasonal prospect or primary home, being next door to Gale Meadow Pond provides a wonderful destination to walk, hike, fish, or just paddle. This home has a private, beautiful yard with its own pond, stream, and firepit just

    Amy Carson Lowe's Real Estate, LLC

    1410 Haven Hill Rd, South Londonderry, VT 05155
    • /40

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,139 Sq Ft

      86 Silver Ln, Vernon, VT 05354

      86 Silver Ln, Vernon, VT 05354
  • /38

    $1,075,000

    • 5 Beds
    • 2.5 Baths
    • 2,338 Sq Ft

    3715 Route 11, Londonderry, VT 05148

    Beautifully expanded and fully renovated 18th-century farmhouse, thoughtfully reimagined by Gray Interiors of Darien, CT. This home blends timeless charm with an elegant yet relaxed New England feel. All systems and mechanicals have been completely updated and modernized. Stylish barnboard accents complement marble countertops, custom cabinetry, high-end finishes like the Shaws sink, and upscale

    Cheyanne Pugliese

    3715 Route 11, Londonderry, VT 05148
  • /45

    $420,000 Sold Oct 10, 2025

    • 1,600 Sq Ft
    • $262/SF
    • 8 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1993

    39 Whites Hill Rd, East Dover, VT 05341

    Escape to your own slice of paradise with this nicely updated 3 Bedroom, 2 Bathroom home nestled on 10 acres of serene, private land while still a short ride to Mount Snow. This home, perfectly blends modern comfort with rural charm and offers numerous updates, including modern finishes and fixtures. The living area features vaulted ceilings and creates a warm and welcoming atmosphere

    Melissa Ellis Southern Vermont Realty Group

    39 Whites Hill Rd, East Dover, VT 05341
    • /30

      Est $442,421 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,482 Sq Ft

      8 Shirley Dr, Vernon, VT 05354

      8 Shirley Dr, Vernon, VT 05354
  • /3

    $275,000

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft

    2173 Vermont 8a, Whitingham, VT 05361

    4 bedroom 2 bath home located on 4.7 acres. Has a ground level access. Level parking and garden spots. There are huge White Pine trees surrounding this home. Showings delayed until September 29, 2025 to allow for cleaning. License to Sell is needed and in progress, Expected in October.

    Mark Yule BHG Masiello Brattleboro

    2173 Vermont 8a, Whitingham, VT 05361

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