30,689

Windham County, VT Homes

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    • /35

      Est $337,165 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

      • 3% Above List Price
      • $200/SF
      • 18 Days On Market

      Last Sold Price $326,000

      Last Listing Agent Jacki Murano Southern Vermont Realty Group

  • /43

    $799,000

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

    39D Dover Springs Ln, Dover, VT 05356

    Located in the highly sought-after Greensprings community at Mount Snow, this spacious 4 bedroom, 4 bath townhouse offers the perfect blend of comfort, convenience, and year-round recreation.The bright, open-concept main living area features vaulted ceilings, abundant natural light, and a cozy fireplace ideal for gathering after a day on the slopes. Large windows and sliding doors invite the

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    39D Dover Springs Ln, Dover, VT 05356
  • /12

    $325,000 Sold Feb 20, 2026

    16 Sycamore St, Brattleboro, VT 05301

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1992

    Last Sold Summary

    • 1% Below List Price
    • $339/SF
    • 10 Days On Market

    Current Estimated Value $319,397

    Last Listing Agent Kelly Agrillo Southern Vermont Realty Group

    16 Sycamore St, Brattleboro, VT 05301
    • /40

      Est $523,345 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

      • 6% Below List Price
      • $242/SF
      • 152 Days On Market

      Last Sold Price $555,000

      Last Listing Agent Monica Sumner BHG Masiello Brattleboro

  • /38

    $399,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 1,119 Sq Ft

    75 E Birch Rd Unit 35, Stratton, VT 05360

    Beautifully updated top-floor condominium located in Stratton Village, offering breathtaking views of Stratton Mountain. The Vantage Point community is ideally positioned to provide a sense of privacy while remaining just minutes from all the year-round amenities Stratton has to offer. A short stroll leads to the Stratton Fitness Center, featuring tennis and pickleball courts, an indoor pool, and

    Kristin Pirie Winhall Real Estate

    75 E Birch Rd Unit 35, Stratton, VT 05360
  • /33

    $400,000 Sold Sep 25, 2025

    211 Upper Dam Rd, Wilmington, VT 05363

    • 3 Beds
    • 3 Baths
    • 2,446 Sq Ft
    • Built 1987

    Last Sold Summary

    • 7% Below List Price
    • $164/SF
    • 48 Days On Market

    Current Estimated Value $447,887

    Last Listing Agent Monique White Deerfield Valley Real Estate

    211 Upper Dam Rd, Wilmington, VT 05363
    • /17

      Est $167,655 Not Listed For Sale

      813 Gates Pond Rd, Jacksonville, VT 05342

      • 2 Beds
      • 1 Bath
      • 826 Sq Ft
      • Built 1846
      813 Gates Pond Rd, Jacksonville, VT 05342

      Last Sold Summary

      • 5% Above List Price
      • $194/SF
      • 5 Days On Market

      Last Sold Price $160,000

      Last Listing Agent Melissa Nebelski Real Broker LLC

  • /3

    $500,000

    • Land
    • 1.1 Acres
    • $454,545 per Acre

    Lot 2 Mountain Ridge Estates, Wilmington, VT 05363

    Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 1.1 acres overlooking the fairway of the 18th hole and mountains

    Adam Palmiter Berkley & Veller Greenwood/Dover

    Lot 2 Mountain Ridge Estates, Wilmington, VT 05363
  • /27

    $475,000 Sold Nov 07, 2025

    0 Lake Hill Rd, Whitingham, VT 05361

    • Land
    • 36.7 Acres
    • $12,943 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 3 Days On Market

    Last Listing Agent Chad Lackey Deerfield Valley Real Estate

    0 Lake Hill Rd, Whitingham, VT 05361
    • /23

      Est $283,791 Not Listed For Sale

      123 Birdville Rd, Whitingham, VT 05361

      • 2 Beds
      • 2 Baths
      • 1,224 Sq Ft
      • Built 1971
      123 Birdville Rd, Whitingham, VT 05361

      Last Sold Summary

      • $233/SF
      • 19 Days On Market

      Last Sold Price $285,000

      Last Listing Agent Regina Perrotto Skihome Realty

  • /18

    $299,000

    • Land
    • 1.06 Acres
    • $282,075 per Acre

    12 Someday Rd, Dover, VT 05356

    Located in the prestigious Someday neighborhood of West Dover,VT this 1.06-acre building lot offers a unique opportunity to create your dream home with breathtaking views of Mount Snow ski resort. The lot, which once housed the original Someday homestead as your footprint, it is now ready for its next chapter. With a permit for sewer in place for a 6-bedroom home, the property provides a head

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    12 Someday Rd, Dover, VT 05356
  • /40

    $225,000 Sold Jun 27, 2025

    6 Papoose Ln, Brookline, VT 05345

    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • Built 1977

    Last Sold Summary

    • $118/SF
    • 58 Days On Market

    Current Estimated Value $259,689

    Last Listing Agent Kate Barry EXP Realty

    6 Papoose Ln, Brookline, VT 05345
    • /40

      Est $379,175 Not Listed For Sale

      4840 Vt Route 100, Whitingham, VT 05361

      • 5 Beds
      • 3.5 Baths
      • 2,248 Sq Ft
      • Built 1845
      4840 Vt Route 100, Whitingham, VT 05361

      Last Sold Summary

      • 28% Below List Price
      • $236/SF
      • 216 Days On Market

      Last Sold Price $530,000

      Last Listing Agent Jacki Murano Southern Vermont Realty Group

  • /26

    $385,000 Under Contract

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

    48 Villager Loop, West Dover, VT 05356

    What a find! This well-maintained 3-bedroom plus den home in the Dover Hills is the perfect year-round Vermont getaway. Just 10 minutes to Mount Snow, you’ll have easy access to world-class skiing and riding in winter and scenic lift-served mountain biking in summer. With a first-floor bedroom and laundry, it’s designed for ease and convenience. Stay cozy with the pellet stove in winter, and cool

    Patrice Schneider Southern Vermont Realty Group

    48 Villager Loop, West Dover, VT 05356
  • /40

    $485,000 Sold Dec 05, 2025

    1 Pheasant Ln, Dover, VT 05356

    • 3 Beds
    • 3 Baths
    • 1,813 Sq Ft
    • Built 1985

    Last Sold Summary

    • 13% Below List Price
    • $268/SF
    • 393 Days On Market

    Current Estimated Value $481,662

    Last Listing Agent Tobin Twelves Skihome Realty

    1 Pheasant Ln, Dover, VT 05356
    • /38

      Est $791,004 Not Listed For Sale

      1793 Faulkner Rd, Whitingham, VT 05361

      • 5 Beds
      • 2.5 Baths
      • 3,332 Sq Ft
      • Built 1830
      1793 Faulkner Rd, Whitingham, VT 05361

      Last Sold Summary

      • 8% Above List Price
      • $220/SF
      • 53 Days On Market

      Last Sold Price $732,606

      Last Listing Agent Jacki Murano Southern Vermont Realty Group

  • /11

    $250,000

    • Land
    • 18 Acres
    • $13,889 per Acre

    0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301

    Tucked in the gently rolling hills of Vermont, this is a sweet spot to build your new home. Located on a class 3 privately maintained road, there are power poles the length of the road with fiber optics ready for the streamers or work at home folks. Build on the road for a short drive and utility ease, or take the secluded route and tuck away in the forest. The acreage is an educated guess and

    Christine Lewis Brattleboro Area Realty

    0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301
  • /2

    $185,000 Sold Dec 19, 2025

    13 Prospect St, Bellows Falls, VT 05101

    • 2 Beds
    • 2 Baths
    • 1,135 Sq Ft
    • Built 1900

    Last Sold Summary

    • 6% Above List Price
    • $163/SF
    • 5 Days On Market

    Current Estimated Value $187,220

    Last Listing Agent Rob Weltz Barrett and Valley Associates Inc.

    13 Prospect St, Bellows Falls, VT 05101
    • /57

      Est $566,500 Not Listed For Sale

      292 Parsons Rd, Jacksonville, VT 05342

      • 4 Beds
      • 1.5 Baths
      • 1,700 Sq Ft
      • Built 1860
      292 Parsons Rd, Jacksonville, VT 05342

      Last Sold Summary

      • 136% Above List Price
      • $141/SF
      • 18 Days On Market

      Last Sold Price $240,000

      Last Listing Agent Donald Koelsch Deerfield Valley Real Estate

  • /51

    $899,800

    • 5 Beds
    • 8 Baths
    • 7,430 Sq Ft

    925 Hinesburg Rd, Brattleboro, VT 05301

    Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

    Christine Lewis Brattleboro Area Realty

    925 Hinesburg Rd, Brattleboro, VT 05301
  • /2

    $30,000 Sold Jun 18, 2025

    0 Scandia Village Rd Unit 5012089, Wardsboro, VT 05360

    • Land
    • 1.1 Acres
    • $27,273 per Acre

    Last Sold Summary

    • 49% Below List Price
    • 292 Days On Market

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    0 Scandia Village Rd Unit 5012089, Wardsboro, VT 05360
    • /29

      Est $898,471 Not Listed For Sale

      2329 Faulkner Rd, Whitingham, VT 05361

      • 4 Beds
      • 3 Baths
      • 2,400 Sq Ft
      • Built 1970
      2329 Faulkner Rd, Whitingham, VT 05361

      Last Sold Summary

      • 5% Below List Price
      • $396/SF
      • 13 Days On Market

      Last Sold Price $950,000

      Last Listing Agent Leslie Fraser Four Seasons Sotheby's Int'l Realty

  • /50

    $415,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 701 Sq Ft

    3034 Route 11, Londonderry, VT 05148

    Are you a large business owner looking for housing for employees, an investor looking for a great opportunity, a landlord looking for more rental units, or are you looking for a ski home with rental income to make it more affordable, or looking for a property to make your home with existing rental income to help make that dream a reality? Look no further than this unique property with endless

    Erin Kendall EXP Realty

    3034 Route 11, Londonderry, VT 05148
  • /2

    $210,000 Sold Aug 29, 2025

    0 Gold Medal Cir Unit 5027515, Stratton, VT 05155

    • Land
    • 2.1 Acres
    • $100,000 per Acre

    Last Sold Summary

    • 16% Below List Price
    • 190 Days On Market

    Last Listing Agent Ross Powers TPW Real Estate

    0 Gold Medal Cir Unit 5027515, Stratton, VT 05155
    • /40

      Est $253,782 Not Listed For Sale

      406 River Rd, Putney, VT 05346

      • 4 Beds
      • 1 Bath
      • 1,512 Sq Ft
      • Built 1952
      406 River Rd, Putney, VT 05346

      Last Sold Summary

      • 4% Below List Price
      • $175/SF
      • 7 Days On Market

      Last Sold Price $265,000

      Last Listing Agent Heidi Bernier Berkley & Veller Greenwood Country

  • /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
  • /33

    $455,000 Sold Mar 04, 2026

    139 Buttonwood Dr, Brattleboro, VT 05301

    • 2 Beds
    • 2 Baths
    • 1,390 Sq Ft
    • Built 2014

    Last Sold Summary

    • 4% Below List Price
    • $327/SF
    • 6 Days On Market

    Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country

    139 Buttonwood Dr, Brattleboro, VT 05301
    • /23

      Est $408,434 Not Listed For Sale

      279 Trail Rd, Putney, VT 05346

      • 2 Beds
      • 3 Baths
      • 3,588 Sq Ft
      • Built 1990
      279 Trail Rd, Putney, VT 05346

      Last Sold Summary

      • 36% Above List Price
      • $84/SF
      • 57 Days On Market

      Last Sold Price $300,000

      Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

  • /43

    $425,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,872 Sq Ft

    1587 Upper Holbrook Rd, Whitingham, VT 05361

    Set on 3 beautiful acres, this well-maintained 3-bedroom plus loft, 2 1/2 bath home is truly move-in ready. Enter through a spacious mudroom with a convenient back opening for bringing in firewood for the cozy wood stove in the living room. The open-concept kitchen and dining area provide plenty of room for entertaining, while a den/game room just off the living room with a bar area (4X8) offers

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    1587 Upper Holbrook Rd, Whitingham, VT 05361
  • /19

    $305,000 Sold Aug 05, 2025

    85 Crosby St, Brattleboro, VT 05301

    • 3 Beds
    • 1 Bath
    • 1,500 Sq Ft
    • Built 1950

    Last Sold Summary

    • 2% Above List Price
    • $203/SF
    • 41 Days On Market

    Current Estimated Value $321,686

    Last Listing Agent Karen Hoppe Berkley & Veller Greenwood Country

    85 Crosby St, Brattleboro, VT 05301
    • /26

      Est $360,817 Not Listed For Sale

      331 Old Codding Rd, Putney, VT 05346

      • 3 Beds
      • 2 Baths
      • 1,818 Sq Ft
      • Built 2005
      331 Old Codding Rd, Putney, VT 05346

      Last Sold Summary

      • 16% Below List Price
      • $238/SF
      • 5 Days On Market

      Last Sold Price $432,000

      Last Listing Agent Heidi Bernier Berkley & Veller Greenwood Country

  • /20

    $449,000

    • 4 Beds
    • 2 Baths
    • 2,219 Sq Ft

    45 Dover Hill Rd, East Dover, VT 05341

    Recently renovated 1900s Colonial just outside the town of Dover, near the Mount Snow ski resort and village of Wilmington, and near Lake Whitingham, with easy access off a paved town road. This cozy Vermont retreat sits on 3+ acres with established trails, a gurgling brook wrapping around the home, bridge to access the rear upper meadow, perennial landscaping, and more. The home is being offered

    Adam Palmiter Berkley & Veller Greenwood/Dover

    45 Dover Hill Rd, East Dover, VT 05341
  • /38

    $650,000 Sold Mar 03, 2026

    1382 Grassy Brook Rd, Brookline, VT 05345

    • 3 Beds
    • 2.5 Baths
    • 3,113 Sq Ft
    • Built 1985

    Last Sold Summary

    • 2% Above List Price
    • $209/SF
    • 123 Days On Market

    Current Estimated Value $545,216

    Last Listing Agent Thomas Dahlin Berkley & Veller Greenwood Country

    1382 Grassy Brook Rd, Brookline, VT 05345
    • /39

      Est $366,477 Not Listed For Sale

      3712 Us Route 5, Westminster, VT 05158

      • 4 Beds
      • 2 Baths
      • 2,423 Sq Ft
      • Built 1792
      3712 Us Route 5, Westminster, VT 05158

      Last Sold Summary

      • 6% Above List Price
      • $142/SF
      • 14 Days On Market

      Last Sold Price $345,000

      Last Listing Agent Wilma Skovinski Berkley & Veller Greenwood Country

  • /8

    $65,000

    • Land
    • 2 Acres
    • $32,500 per Acre

    585 Sawmill Rd, Stratton, VT 05360

    Ready to build! Nestled in the picturesque Snow Mountain Farms development, this prime 2 acre property offers the perfect canvas for your dream home. Situated in a great neighborhood with a convenient location, it provides easy access to both Mount Snow and Stratton. The property is equipped with a wastewater permit, septic design, an already cleared building envelope, and a driveway. Association

    Carrie Mathews Winhall Real Estate

    585 Sawmill Rd, Stratton, VT 05360
  • /26

    $320,000 Sold May 30, 2025

    231 Sawdust Aly, Townshend, VT 05353

    • 3 Beds
    • 2 Baths
    • 1,921 Sq Ft
    • Built 1950

    Last Sold Summary

    • 20% Below List Price
    • $167/SF
    • 172 Days On Market

    Current Estimated Value $330,925

    Last Listing Agent Victoria Woods Brattleboro Area Realty

    231 Sawdust Aly, Townshend, VT 05353
    • /19

      Est $329,323 Not Listed For Sale

      2170 Kurn Hattin Rd, Putney, VT 05346

      • 3 Beds
      • 1 Bath
      • 1,404 Sq Ft
      • Built 1992
      2170 Kurn Hattin Rd, Putney, VT 05346

      Last Sold Summary

      • 1% Above List Price
      • $233/SF
      • 29 Days On Market

      Last Sold Price $327,500

      Last Listing Agent Kassie Rubico Berkley & Veller Greenwood Country

  • /10

    $199,000

    • 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
  • /43

    $887,000 Sold Oct 17, 2025

    460 Stratton Gate Rd, Jamaica, VT 05343

    • 4 Beds
    • 3 Baths
    • 3,155 Sq Ft
    • Built 1992

    Last Sold Summary

    • 1% Below List Price
    • $281/SF
    • 12 Days On Market

    Current Estimated Value $975,095

    Last Listing Agent Helen Nault

    460 Stratton Gate Rd, Jamaica, VT 05343
    • /40

      Est $734,408 Not Listed For Sale

      680 Beebe Rd, Putney, VT 05346

      • 3 Beds
      • 3 Baths
      • 2,262 Sq Ft
      • Built 1801
      680 Beebe Rd, Putney, VT 05346

      Last Sold Summary

      • 14% Below List Price
      • $376/SF
      • 75 Days On Market

      Last Sold Price $850,000

      Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country

Showing Results 361 - 400, Page 10 of 18

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