31,018

Windham County, VT Homes

Section Image
    • /23

      Est $506,388

      Not Listed For Sale

      2 Ives Rd, Wilmington, VT 05363

      • 4 Beds
      • 3 Baths
      • 1,200 Sq Ft
      • Built 1960
      2 Ives Rd, Wilmington, VT 05363

      Last Sold Summary

      • 159 Days On Market

  • /35

    $34,900

    • 1 Bed
    • 2 Baths
    • 745 Sq Ft

    341/43 Qtr.4,89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This sleep 6 unit consists of two adjoining units; Studio unit (341) Queen murphy bed, kitchenette, full bathroom . Hotel unit (343) Two king beds, full bathroom. Units are located on the third floor mountain side of the hotel. Lock out units have the benefit of using the unit as a whole or stay in one side and rent the other

    Kelly Agrillo Southern Vermont Realty Group

    341/43 Qtr.4,89 Grand Summit Way, Dover, VT 05356
  • /37

    $273,500

    Sold May 14, 2026

    2378 Deer Park Rd, West Halifax, VT 05358

    • 2 Beds
    • 1 Bath
    • 936 Sq Ft
    • Built 1988

    Last Sold Summary

    • 5% Below List Price
    • $292/SF
    • 4 Days On Market

    Current Estimated Value $276,658

    Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty

    2378 Deer Park Rd, West Halifax, VT 05358
    • /31

      Est $374,420

      Not Listed For Sale

      962 Chapel Hill Rd, Whitingham, VT 05361

      • 3 Beds
      • 2 Baths
      • 1,963 Sq Ft
      • Built 1988
      962 Chapel Hill Rd, Whitingham, VT 05361

      Last Sold Summary

      • 7 Days On Market

  • /36

    $549,000

    Open Sun 1:30PM - 3:30PM
    • 4 Beds
    • 3 Baths
    • 1,936 Sq Ft

    202 Twin Brook Cir, Londonderry, VT 05148

    Tucked away at the end of a long private driveway on a quiet cul-de-sac, this impeccable 4-bedroom chalet offers the perfect blend of privacy, adventure, and year-round Vermont living in the sought-after Powder Mill community. Set on 1.54 wooded acres, the property is surrounded by nature with access to maintained hiking and snowmobile trails, including connections to the VAST trail network and

    Carrie Mathews Winhall Real Estate

    202 Twin Brook Cir, Londonderry, VT 05148
  • /26

    $515,000

    Sold Aug 21, 2025

    89 Birch Rd Unit 51, Londonderry, VT 05148

    • 4 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Built 1980

    Last Sold Summary

    • $335/SF
    • 11 Days On Market

    Current Estimated Value $523,012

    Last Listing Agent Kevin Moran Four Seasons Sotheby's Int'l Realty

    89 Birch Rd Unit 51, Londonderry, VT 05148
    • /31

      Not Listed For Sale

      1124 Chapel Hill Rd, Whitingham, VT 05361

      1124 Chapel Hill Rd, Whitingham, VT 05361

      Last Sold Summary

      • 64 Days On Market

  • /39

    $610,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 3,700 Sq Ft

    53 Country Ln, Wardsboro, VT 05355

    Tucked between Mount Snow and Stratton, this charming mountain retreat offers the perfect blend of adventure, comfort, and classic Vermont living. Set in the heart of Wardsboro, this property provides easy access to both year-round recreation and peaceful natural surroundings. After a day on the slopes or exploring the nearby Green Mountain National Forest, cozy up beside the inviting wood

    Mike Masters Four Seasons Sotheby's Int'l Realty

    53 Country Ln, Wardsboro, VT 05355
  • /23

    $427,380

    Sold Apr 27, 2026

    1528 Townshend Rd, Grafton, VT 05146

    • 3 Beds
    • 1 Bath
    • 1,024 Sq Ft
    • Built 1950

    Last Sold Summary

    • 2% Above List Price
    • $417/SF
    • 4 Days On Market

    Current Estimated Value $418,024

    Last Listing Agent Andie Fusco Four Seasons Sotheby's Int'l Realty

    1528 Townshend Rd, Grafton, VT 05146
    • /46

      Est $456,947

      Not Listed For Sale

      1448 Cyrus Rd, Whitingham, VT 05361

      • 3 Beds
      • 2 Baths
      • 1,438 Sq Ft
      • Built 1978
      1448 Cyrus Rd, Whitingham, VT 05361

      Last Sold Summary

      • 15 Days On Market

  • /40

    $200,000

    • 5,340 Sq Ft

    23 Main St, Saxtons River, VT 05154

    Start your winter project now! This amazing 3 story Victorian right in the middle of one of our sweetest villages, is begging for a return to glory. You can't beat the construction, the multilayered woodwork, amazing windows, original fireplace mantels and fronts! There is a lot to do here, but the end product will be breathtaking. Currently set up as 4 apartments, with a 3rd floor bonus, but is

    Christine Lewis Brattleboro Area Realty

    23 Main St, Saxtons River, VT 05154
  • /44

    $405,000

    Sold Jul 28, 2025

    156 Sherwood Cir, Brattleboro, VT 05301

    • 4 Beds
    • 2.5 Baths
    • 2,132 Sq Ft
    • Built 1998

    Last Sold Summary

    • 8% Above List Price
    • $190/SF
    • 33 Days On Market

    Current Estimated Value $383,600

    Last Listing Agent Fine Homes Group International Keller Williams Realty-Metropolitan

    156 Sherwood Cir, Brattleboro, VT 05301
    • /26

      Est $253,874

      Not Listed For Sale

      2815 Burrington Hill Rd, Whitingham, VT 05361

      • 1 Bed
      • 1 Bath
      • 700 Sq Ft
      • Built 1982
      2815 Burrington Hill Rd, Whitingham, VT 05361

      Last Sold Summary

      • 6 Days On Market

  • /15

    $59,900

    $15K PRICE DROP
    • Land
    • 2 Acres
    • $29,950 per Acre

    585 Sawmill Rd, Stratton, VT 05360

    Ready to build your Vermont dream home! Perfectly positioned between Stratton Mountain and Mount Snow, this exceptional 2-acre property offers the ideal blend of privacy, recreation, and convenience in the highly desirable Snow Mountain Farms community.Set within a picturesque mountain setting, the property is already prepared for construction with a cleared building envelope, driveway,

    Carrie Mathews Winhall Real Estate

    585 Sawmill Rd, Stratton, VT 05360
  • /33

    $377,840

    Sold Aug 19, 2025

    111 Bonnyvale Rd, Brattleboro, VT 05301

    • 3 Beds
    • 1.5 Baths
    • 1,536 Sq Ft
    • Built 2000

    Last Sold Summary

    • 8% Above List Price
    • $246/SF
    • 103 Days On Market

    Current Estimated Value $376,411

    Last Listing Agent Stephanie Peduzzi-Baker Brattleboro Area Realty

    111 Bonnyvale Rd, Brattleboro, VT 05301
    • /12

      Not Listed For Sale

      2027 Burrington Hill Rd, Whitingham, VT 05361

      2027 Burrington Hill Rd, Whitingham, VT 05361

      Last Sold Summary

      • 262 Days On Market

  • /28

    $350,000

    $20K PRICE DROP Under Contract
    • 4 Beds
    • 1.5 Baths
    • 1,800 Sq Ft

    39 Locust St, Brattleboro, VT 05301

    Sweet and charming from an era of wonderful wood work, polished floors and rooms with a purpose. This home has a lovely big kitchen with a peninsula for baking prep, formal dining with built in china cabinet, living room and an first floor bedroom with 1/2 bath. Since the basement is walk out, the back porch is 2nd level, above the bugs, and overlooking the private back yard. Fenced for a dog,

    Christine Lewis Brattleboro Area Realty

    39 Locust St, Brattleboro, VT 05301
  • /39

    $535,000

    Sold Aug 14, 2025

    408 Dover Rd, South Newfane, VT 05351

    • 3 Beds
    • 3 Baths
    • 2,364 Sq Ft
    • Built 1795

    Last Sold Summary

    • 2% Above List Price
    • $226/SF
    • 23 Days On Market

    Current Estimated Value $521,596

    Last Listing Agent David Brown

    408 Dover Rd, South Newfane, VT 05351
    • /38

      Est $459,540

      Not Listed For Sale

      1452 Maple Hill Ln, Whitingham, VT 05361

      • 2 Beds
      • 2.5 Baths
      • 1,750 Sq Ft
      • Built 1975
      1452 Maple Hill Ln, Whitingham, VT 05361

      Last Sold Summary

      • 54 Days On Market

  • /42

    $449,990

    $125K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft

    555 Vermont 9, Wilmington, VT 05363

    Located just minutes from the slopes of Mount Snow, the pristine waters of Lake Raponda, and the expansive Harriman Reservoir, this property offers the ideal combination of convenience, recreation, and opportunity. With ample space and zoning flexibility, you have the unique chance to build an Accessory Dwelling Unit (ADU) on-site, perfect for generating rental income, hosting guests, or creating

    Colt Hazell Flex Realty

    555 Vermont 9, Wilmington, VT 05363
  • /4

    $232,500

    Sold Sep 18, 2025

    0 Gold Medal Cir Unit 5023219, Stratton, VT 05155

    • Land
    • 1.57 Acres
    • $148,089 per Acre

    Last Sold Summary

    • 7% Below List Price
    • 238 Days On Market

    Last Listing Agent Ross Powers TPW Real Estate

    0 Gold Medal Cir Unit 5023219, Stratton, VT 05155
    • /29

      Est $537,518

      Not Listed For Sale

      960 Holbrook Rd, Jacksonville, VT 05342

      • 3 Beds
      • 2 Baths
      • 2,600 Sq Ft
      • Built 1968
      960 Holbrook Rd, Jacksonville, VT 05342

      Last Sold Summary

      • 14 Days On Market

  • /10

    $199,000

    $51K PRICE DROP
    • Land
    • 23.1 Acres
    • $8,615 per Acre

    184 Dupre Dr, Guilford, VT 05301

    Here's a large 23.10 +/- acre parcel that's mostly wooded but with a little bit of open field and possible short range local views. Conveniently located within a few minutes of town, here's an opportunity to enjoy country living while having access to modern amenities. There's a lot of potential for the right buyer! Please respect the privacy of the other houses on the road past this land.

    A.J. Bellville Bellville Realty

    184 Dupre Dr, Guilford, VT 05301
  • /58

    $475,000

    Sold Oct 10, 2025

    1923 N Hill Rd, Chester, VT 05143

    • 5 Beds
    • 3 Baths
    • 2,316 Sq Ft
    • Built 1981

    Last Sold Summary

    • 2% Below List Price
    • $205/SF
    • 6 Days On Market

    Last Listing Agent Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    1923 N Hill Rd, Chester, VT 05143
    • /40

      Est $447,710

      Not Listed For Sale

      656 Allard Rd, Whitingham, VT 05361

      • 4 Beds
      • 2 Baths
      • 2,000 Sq Ft
      • Built 1949
      656 Allard Rd, Whitingham, VT 05361

      Last Sold Summary

      • 56 Days On Market

  • /27

    $559,000

    • 4 Beds
    • 3 Baths
    • 2,050 Sq Ft

    39 B Kingswood Rd, Dover, VT 05356

    Experience turnkey mountain living in this impeccably maintained and beautifully furnished Kingswood townhome, ideally situated just minutes from Mount Snow and the Hermitage Club. Recently painted and offered fully furnished, this move-in-ready retreat seamlessly blends comfort, convenience, and year-round recreation. Designed for both relaxation and entertaining, the spacious floor plan

    Patricia Fitzpatrick Skihome Realty

    39 B Kingswood Rd, Dover, VT 05356
  • /60

    $235,000

    Sold Aug 29, 2025

    111 Binney Brook Rd Unit M581, Wilmington, VT 05363

    • 3 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • Built 1970

    Last Sold Summary

    • 10% Below List Price
    • $188/SF
    • 32 Days On Market

    Current Estimated Value $227,171

    Last Listing Agent Sigrid Pickering Chimney Hill Realty

    111 Binney Brook Rd Unit M581, Wilmington, VT 05363
    • /32

      Est $257,766

      Not Listed For Sale

      329 Deer Hill Rd, Whitingham, VT 05361

      • 2 Beds
      • 1 Bath
      • 952 Sq Ft
      • Built 1968
      329 Deer Hill Rd, Whitingham, VT 05361

      Last Sold Summary

      • 6 Days On Market

  • /39

    $550,000

    • Land
    • 99.4 Acres
    • $5,533 per Acre

    188 Rattlesnake Mountain Rd, Townshend, VT 05353

    Townshend, Vermont sits in the heart of the West River Valley, minutes from Grafton, Londonderry, and Brattleboro. The property borders Vermont Route 30 and offers easy access to two of southern Vermont's premier ski resorts and the broader four-season recreational economy. A rare opportunity to own nearly 100 acres of productive Vermont forestland in one of Windham County's most scenic corridors

    Mike England Michael England Real Estate

    188 Rattlesnake Mountain Rd, Townshend, VT 05353
  • /48

    $391,000

    Sold Apr 07, 2026

    58-60 Frost Place, Brattleboro, VT 05301

    • 6 Beds
    • 2 Baths
    • 2,048 Sq Ft
    • Built 1930

    Last Sold Summary

    • 6% Below List Price
    • $191/SF
    • 142 Days On Market

    Last Listing Agent Lily Gautot Greenwald Realty Group

    58-60 Frost Place, Brattleboro, VT 05301
    • /39

      Est $640,787

      Not Listed For Sale

      3358 Vt Route 100, Whitingham, VT 05361

      • 5 Beds
      • 5 Baths
      • 3,300 Sq Ft
      • Built 1900
      3358 Vt Route 100, Whitingham, VT 05361

      Last Sold Summary

      • 118 Days On Market

  • /47

    $798,000

    $100K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,420 Sq Ft

    41 Two Brook Dr, Wilmington, VT 05363

    Tucked onto .50-acre setting with Two Brook gently flowing through the backyard, this beautifully appointed 4 bedroom, 5 bath home captures everything buyers love about Vermont mountain living privacy, warmth, and year-round recreation just minutes from it all.Ideally located near The Hermitage Club and Mount Snow, with direct access to VAST snowmobile trails and a short drive to the shops

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    41 Two Brook Dr, Wilmington, VT 05363
  • /30

    $325,000

    Sold Mar 20, 2026

    119 Newton Hill Rd, Vernon, VT 05354

    • 3 Beds
    • 1.5 Baths
    • 1,674 Sq Ft
    • Built 1976

    Last Sold Summary

    • 3% Above List Price
    • $194/SF
    • 7 Days On Market

    Current Estimated Value $326,352

    Last Listing Agent Jim Bellville Bellville Realty

    119 Newton Hill Rd, Vernon, VT 05354
    • /29

      Est $620,853

      Not Listed For Sale

      55 Reed Hill Rd, Jacksonville, VT 05342

      • 5 Beds
      • 3 Baths
      • 2,732 Sq Ft
      • Built 1840
      55 Reed Hill Rd, Jacksonville, VT 05342

      Last Sold Summary

      • 35 Days On Market

  • /18

    $535,000

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft

    12 Ober Tal Dr Unit C14, Stratton, VT 05360

    Opportunity awaits in this trailside condominium at Stratton Mountain Resort. Ideally positioned for convenient access to the Tamarack Chairlift and Stratton Village, this residence offers the mountain lifestyle buyers seek with direct access to skiing, dining, shopping, and year-round resort amenities. Inside, a wood-burning fireplace anchors the living area, creating an inviting space to gather

    Timothy Mich Doddridge Stratton Real Estate

    12 Ober Tal Dr Unit C14, Stratton, VT 05360
  • /2

    $345,000

    Sold Oct 07, 2025

    154 Reed Rd, Chester, VT 05143

    • 2 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Above List Price
    • $308/SF
    • 10 Days On Market

    Current Estimated Value $296,455

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    154 Reed Rd, Chester, VT 05143
    • /35

      Est $343,705

      Not Listed For Sale

      159 Reed Hill Rd, Jacksonville, VT 05342

      • 3 Beds
      • 3 Baths
      • 1,626 Sq Ft
      • Built 1959
      159 Reed Hill Rd, Jacksonville, VT 05342

      Last Sold Summary

      • 18 Days On Market

  • /34

    $175,000

    • 3 Beds
    • 1.5 Baths
    • 1,130 Sq Ft

    58 Scandia Village Rd, West Wardsboro, VT 05360

    Tucked away on 1.20 acres in Wardsboro, this 3-bedroom, 1.5-bath home offers a peaceful Vermont setting with plenty of outdoor space to enjoy. The home features 1,130 finished square feet with a warm, cabin-like interior, wood accents, and an inviting open living area with a wood stove insert for added comfort. The kitchen flows nicely into the main living space, creating an easy layout for

    Grayson VanHendrick Flex Realty

    58 Scandia Village Rd, West Wardsboro, VT 05360
  • /20

    $361,589

    Sold Oct 30, 2025

    43 Bear Lair Ln, Wilmington, VT 05363

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1970

    Last Sold Summary

    • 4% Below List Price
    • $314/SF
    • 85 Days On Market

    Current Estimated Value $385,655

    Last Listing Agent Jim Bellville Bellville Realty

    43 Bear Lair Ln, Wilmington, VT 05363
    • /40

      Est $542,994

      Not Listed For Sale

      371 Butler Brook Rd, Jacksonville, VT 05342

      • 5 Beds
      • 2.5 Baths
      • 2,296 Sq Ft
      • Built 1976
      371 Butler Brook Rd, Jacksonville, VT 05342

      Last Sold Summary

      • 152 Days On Market

Showing Results 401 - 440, Page 11 of 18

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