30,889

Windham County, VT Homes

Section Image
    • /23

      Est $508,829

      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

  • /40

    $379,000

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

    442 Brookline Rd, Newfane, VT 05345

    Welcome to the Green Mountains! Nestled on 12.8 private acres, this quintessential, one-of-a-kind timber frame cabin offers a rare blend of craftsmanship and nature. Bordering the protected Pinnacle Association preserve, you can walk right out your front door to explore amazing trails and local wildlife. Lovingly constructed by local artist and builder Nathan Guest, the home’s creative vision is

    Kristen Ziter Taylor Brattleboro Area Realty

    442 Brookline Rd, Newfane, VT 05345
  • /24

    $285,000

    Sold Jun 12, 2025

    730 Hubbard Hill Rd, Halifax, VT 05342

    • 2 Beds
    • 2 Baths
    • 1,324 Sq Ft
    • Built 1971

    Last Sold Summary

    • 4% Above List Price
    • $215/SF
    • 8 Days On Market

    Last Listing Agent Stephanie Wilde

    730 Hubbard Hill Rd, Halifax, VT 05342
    • /31

      Est $373,771

      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

  • /26

    $564,900

    Under Contract
    • 5 Beds
    • 3.5 Baths
    • 3,140 Sq Ft

    43 Edwards Village Loop, Dover, VT 05356

    Enjoy amazing proximity to the Mount Snow ski resort, with easy access yet total privacy, in this updated contemporary farmhouse. At the end of a quiet loop sits this lovely home on 1.92 acres with nearby access to restaurants, shopping, and shuttle service. The home has been recently renovated and now features an open concept living room with ample living space and spacious kitchen, large deck

    Adam Palmiter Berkley & Veller Greenwood/Dover

    43 Edwards Village Loop, Dover, VT 05356
  • /55

    $479,000

    Sold Aug 22, 2025

    1 Dorr Fitch Rd, Dover, VT 05356

    • 4 Beds
    • 3 Baths
    • 2,566 Sq Ft
    • Built 1900

    Last Sold Summary

    • $187/SF
    • 1 Day On Market

    Current Estimated Value $465,189

    Last Listing Agent Donald Koelsch Deerfield Valley Real Estate

    1 Dorr Fitch Rd, Dover, VT 05356
    • /31

      Est $106,946

      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

  • /27

    $169,900

    • 3 Beds
    • 2 Baths
    • 2,246 Sq Ft

    1102 Route 100, Wardsboro, VT 05355

    A great, affordable starter! Mostly open concept with L/D/FM and kitchen all flowing one to the other with lots of windows for light and air, bringing the outside in. There is also a bedroom and full bath on the first floor for aging in place. Attached is a huge shed for a workshop. The big surprise and great treat is the lot across the street that borders the Wardsboro Brook and could be a

    Christine Lewis Brattleboro Area Realty

    1102 Route 100, Wardsboro, VT 05355
  • /13

    $91,500

    Sold May 20, 2026

    78 Captain Copeland Rd, Dover, VT 05341

    • Land
    • 10.05 Acres
    • $9,104 per Acre

    Last Sold Summary

    • 8% Below List Price
    • 3 Days On Market

    Last Listing Agent Carrie Mathews Winhall Real Estate

    78 Captain Copeland Rd, Dover, VT 05341
    • /26

      Est $252,128

      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

  • /32

    $575,000

    $23K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,892 Sq Ft

    238 Hemlock Hill Rd, Wardsboro, VT 05355

    This spacious 5 bedroom home is located on a private lot in the popular Snow Mountain Farms community. The Property has a brand new roof!!! The three levels offer privacy and quiet with an outdoor fire pit, garden shed, and access to the VAST snowmobile trails across the street. Its open floor plan with vaulted ceilings and stone hearth gas fireplace is perfect for aprés ski gatherings, and the

    Jeffrey Sheehan Cummings & Co

    238 Hemlock Hill Rd, Wardsboro, VT 05355
  • /30

    $1,000,000

    Sold Jan 30, 2026

    585 Pleasant Valley Rd, Jamaica, VT 05343

    • Land
    • 108 Acres
    • $9,259 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 293 Days On Market

    Current Estimated Value $995,134

    Last Listing Agent Britt Wohler

    585 Pleasant Valley Rd, Jamaica, VT 05343
    • /12

      Est $302,000

      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

  • /39

    $2,900,000

    • 34,419 Sq Ft

    14 Westminster St, Town of Rockingham, VT 05154

    For developers or investors seeking property with stable income and growth potential, the Warner Center campus presents an excellent opportunity. This surveyed 140-acre property comprises 24 residential rental units and 3 commercial spaces within six extensively renovated brick buildings – over 34,000sf altogether. The buildings are situated in a spacious, sunlit field, conveniently located

    Heidi Bernier Berkley & Veller Greenwood Country

    14 Westminster St, Town of Rockingham, VT 05154
  • /44

    $359,350

    Sold Sep 26, 2025

    399 Laurel Lake Rd, Jacksonville, VT 05342

    • 2 Beds
    • 3 Baths
    • 1,696 Sq Ft
    • Built 1930

    Last Sold Summary

    • 10% Below List Price
    • $212/SF
    • 17 Days On Market

    Current Estimated Value $355,868

    Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

    399 Laurel Lake Rd, Jacksonville, VT 05342
    • /29

      Est $519,758

      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

  • /57

    $850,000

    • 5 Beds
    • 4 Baths
    • 3,218 Sq Ft

    4880 Pikes Falls Rd, Jamaica, VT 05343

    Welcome to your perfect four-season retreat nestled just minutes from Stratton Mountain Ski Resort. This authentic 5-bedroom, 4-bathroom log cabin plenty of space throughout, with ample natural light and that signature Vermont charm and cozy ambiance. A large kitchen, combined with an open dining area and expansive wrap around deck, offer a multitude of opportunities for seasonal gatherings no

    Mike England Michael England Real Estate

    4880 Pikes Falls Rd, Jamaica, VT 05343
  • /42

    $590,000

    Sold May 18, 2026

    299 Sunset Lake Rd, Brattleboro, VT 05301

    • 3 Beds
    • 2.5 Baths
    • 1,995 Sq Ft
    • Built 1999

    Last Sold Summary

    • 9% Below List Price
    • $296/SF
    • 21 Days On Market

    Current Estimated Value $565,659

    Last Listing Agent Peggy Winchester ACORN REAL ESTATE GROUP LLC

    299 Sunset Lake Rd, Brattleboro, VT 05301
    • /40

      Est $426,587

      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

  • /23

    $465,900

    $33K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,548 Sq Ft

    28 Lightning Ledge Way, Wilmington, VT 05363

    Private 2004 country chalet in the Chimney Hill community just outside the village of Wilmington. Hiking trails, snowmobile trail access, and convenient nearby snowmobile trailer parking, make this super convenient for the outdoorsy. This home sits on a rare double lot, just up from the beautifully renovated Chimney Hill clubhouse, Lake Whitingham, and Mount Snow ski resort, affording year round

    Adam Palmiter Berkley & Veller Greenwood/Dover

    28 Lightning Ledge Way, Wilmington, VT 05363
  • /11

    $153,000

    Sold Aug 25, 2025

    41 Old Depot Rd, Putney, VT 05346

    • Land
    • 4.53 Acres
    • $33,775 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 33 Days On Market

    Current Estimated Value $441,486

    Last Listing Agent Victoria Woods Brattleboro Area Realty

    41 Old Depot Rd, Putney, VT 05346
    • /32

      Est $244,195

      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

  • /33

    $19,500

    • 1 Bed
    • 1 Bath
    • 589 Sq Ft

    102, Qtr 4 Grand Summit Way Unit 102, Qtr 4, Dover, VT 05356

    Trailside! Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Own this deeded quartershare property for 1 week every 28 days, on a rotating basis. This 1-of-a-kind, end-unit, slopeside 1-bedroom, 1 full bath unit has sleeping space for 4, and looks out over the Sundance Base Lodge and the Sundance Express, the new 6-person chairlift. Open-concept kitchen/dining room, and a

    Donna Brown Skihome Realty

    102, Qtr 4 Grand Summit Way Unit 102, Qtr 4, Dover, VT 05356
  • /37

    $370,000

    Sold Feb 12, 2026

    3298 Houghtonville Rd, Grafton, VT 05146

    • 4 Beds
    • 2 Baths
    • 2,400 Sq Ft
    • Built 1890

    Last Sold Summary

    • 6% Below List Price
    • $154/SF
    • 44 Days On Market

    Current Estimated Value $389,206

    Last Listing Agent Alison Cummings Cummings & Co

    3298 Houghtonville Rd, Grafton, VT 05146
    • /39

      Est $588,222

      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

  • /2

    $370,000

    • 5 Beds
    • 4 Baths
    • 3,002 Sq Ft

    10 Birge St, Brattleboro, VT 05301

    Invest in your own home town! Full tenant roster with the easy access to laundry across the street, grocery stores, train and The Moover. Right in the heart of things with little yard to maintain! Consider as an investment in your portfolio or decide to live in one unit and have the others pay your mortgage! Good way to start, retire or increase your portfolio! Owner is a licensed appraiser.

    Christine Lewis Brattleboro Area Realty

    10 Birge St, Brattleboro, VT 05301
  • /26

    $520,000

    Sold Sep 25, 2025

    18 Old Town Rd, West Dover, VT 05356

    • 3 Beds
    • 1.5 Baths
    • 2,145 Sq Ft
    • Built 1981

    Last Sold Summary

    • 5% Below List Price
    • $242/SF
    • 15 Days On Market

    Current Estimated Value $507,971

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    18 Old Town Rd, West Dover, VT 05356
    • /29

      Est $602,457

      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

  • /16

    $19,999

    • Land
    • 1 Acre
    • $19,999 per Acre

    0 Hunter Brook Rd, South Newfane, VT 05351

    Beautiful creekside property in Newfane, ideal for camping, fishing, or RVing. The western boundary line follows Hunter Brook, which turns like a horseshoe at this location and almost meets the eastern boundary: Hunter Brook Road. As a result the property naturally divides itself into two sides, each with its own strengths and weaknesses.The northeastern side is larger, more private, and

    David White OwnerEntry.com

    0 Hunter Brook Rd, South Newfane, VT 05351
  • /22

    $89,900

    Sold Jan 23, 2026

    2 Wagon Dr, Brattleboro, VT 05301

    • 2 Beds
    • 2 Baths
    • 910 Sq Ft
    • Built 1977

    Last Sold Summary

    • $99/SF
    • 6 Days On Market

    Last Listing Agent Christine Lewis Brattleboro Area Realty

    2 Wagon Dr, Brattleboro, VT 05301
    • /35

      Est $316,229

      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

  • /36

    $529,000

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,044 Sq Ft

    11 Dutchman Ln Unit 4A, Wilmington, VT 05363

    This 3-bedroom plus loft, 2.5-bath end unit townhouse is in Powderhorn Village. The entrance boasts a mudroom, leading to a dining area adjacent to a fully equipped kitchen, complemented by a convenient powder room and living space with a wood-burning fieldstone fireplace. Access to an oversized deck and a bonus room with a hot tub and a private shower. Ascend to the second floor to find the

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    11 Dutchman Ln Unit 4A, Wilmington, VT 05363
  • /19

    $400,000

    Sold Dec 15, 2025

    48 Landing Ln, Wilmington, VT 05363

    • 4 Beds
    • 2 Baths
    • 2,056 Sq Ft
    • Built 2003

    Last Sold Summary

    • 20% Below List Price
    • $195/SF
    • 52 Days On Market

    Current Estimated Value $415,649

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    48 Landing Ln, Wilmington, VT 05363
    • /40

      Est $515,240

      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

  • /31

    $599,000

    • 5 Beds
    • 2 Baths
    • 1,800 Sq Ft

    48 Upper Highlands, Dover, VT 05356

    Unique opportunity to own an updated and woodsy chalet just up from the slopes of Mt Snow, yet also with direct snowmobile trail access. This 5 bedroom, 2 bath home has been tastefully renovated while maintaining the charm and character befitting a Vermont retreat ski home. The interior features an open concept living space with vaulted great room, wood burning fireplace, natural woodwork and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    48 Upper Highlands, 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 $326,935

    Last Listing Agent Kelly Agrillo Southern Vermont Realty Group

    16 Sycamore St, Brattleboro, VT 05301
    • /17

      Est $174,505

      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 Days On Market

  • /17

    $312,900

    • 3 Beds
    • 1.5 Baths
    • 1,080 Sq Ft

    2448 Burrington Hill Rd, Whitingham, VT 05361

    Charming cottage just up from the MA border in Whitingham Vermont. This lovely home sits on a 4 acre parcel with great lawn space, easy paved road access, and a pastoral setting with adjacent nearby farmland and large parcels. The home has been well maintained and features an open kitchen, dining, and living space on the main floor, with full bath. The second story features a large primary

    Michael Purcell Berkley & Veller Greenwood/Dover

    2448 Burrington Hill Rd, Whitingham, VT 05361
  • /26

    $385,000

    Sold Jun 01, 2026

    135 Country Hill, Brattleboro, VT 05301

    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft
    • Built 2004

    Last Sold Summary

    • 3% Below List Price
    • $181/SF
    • 35 Days On Market

    Current Estimated Value $396,727

    Last Listing Agent Neil Goldberg Brattleboro Area Realty

    135 Country Hill, Brattleboro, VT 05301
    • /23

      Est $273,501

      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

      • 19 Days On Market

Showing Results 321 - 360, Page 9 of 18

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