31,018

Windham County, VT Homes

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  • /40

    $350,000

    • 2,745 Sq Ft

    120 Western Ave, Brattleboro, VT 05301

    Discover this lovingly cared-for two-unit multi-family property, ideally located in town with convenient access to shopping, restaurants, public transportation, and everyday amenities. Each unit offers a comfortable layout featuring 2 bedrooms and 1 bathroom, making this property an excellent opportunity for owner-occupants, investors, or those seeking rental income. Pride of ownership is evident

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    120 Western Ave, Brattleboro, VT 05301
  • /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 $488,335

    Last Listing Agent Victoria Woods Brattleboro Area Realty

    41 Old Depot Rd, Putney, VT 05346
    • /26

      Est $439,625

      Not Listed For Sale

      11 Corn Hill Rd, West Townshend, VT 05359

      • 6 Beds
      • 2 Baths
      • 3,005 Sq Ft
      • Built 1834
      11 Corn Hill Rd, West Townshend, VT 05359

      Last Sold Summary

      • 71 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
  • /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 $385,978

    Last Listing Agent Alison Cummings Cummings & Co

    3298 Houghtonville Rd, Grafton, VT 05146
    • /37

      Not Listed For Sale

      8117 Windham Hill Rd, West Townshend, VT 05359

      • 2 Beds
      • 1 Bath
      • 1,340 Sq Ft
      • Built 1950
      8117 Windham Hill Rd, West Townshend, VT 05359

      Last Sold Summary

      • 18 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
  • /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 $494,689

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    18 Old Town Rd, West Dover, VT 05356
    • /40

      Est $2,096,270

      Not Listed For Sale

      118 W Lake Rd, Wilmington, VT 05363

      • 4 Beds
      • 3.5 Baths
      • 5,392 Sq Ft
      • Built 2018
      118 W Lake Rd, Wilmington, VT 05363

      Last Sold Summary

      • 21 Days On Market

  • /32

    $550,000

    $48K 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
  • /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
    • /22

      Est $352,598

      Not Listed For Sale

      498 Stowe Hill Rd, Wilmington, VT 05363

      • 3 Beds
      • 1 Bath
      • 1,000 Sq Ft
      • Built 1965
      498 Stowe Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 115 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
  • /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 $422,060

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    48 Landing Ln, Wilmington, VT 05363
    • /24

      Est $652,936

      Not Listed For Sale

      82 Lisle Hill Rd, Wilmington, VT 05363

      • 7 Beds
      • 4.5 Baths
      • 3,600 Sq Ft
      • Built 1989
      82 Lisle Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 177 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
  • /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 $327,760

    Last Listing Agent Kelly Agrillo Southern Vermont Realty Group

    16 Sycamore St, Brattleboro, VT 05301
    • /29

      Est $369,488

      Not Listed For Sale

      19 Stowe Hill Rd, Wilmington, VT 05363

      • 3 Beds
      • 2 Baths
      • 1,632 Sq Ft
      • Built 1968
      19 Stowe Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 76 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
  • /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 $393,862

    Last Listing Agent Neil Goldberg Brattleboro Area Realty

    135 Country Hill, Brattleboro, VT 05301
    • /53

      Not Listed For Sale

      29 Ray Hill Rd, Wilmington, VT 05363

      • 4 Beds
      • 1.5 Baths
      • 2,196 Sq Ft
      • Built 1957
      29 Ray Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 34 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
  • /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 $484,866

    Last Listing Agent Monique White Deerfield Valley Real Estate

    211 Upper Dam Rd, Wilmington, VT 05363
    • /33

      Est $388,284

      Not Listed For Sale

      8 Castle Hill Rd, Wilmington, VT 05363

      • 4 Beds
      • 2 Baths
      • 1,643 Sq Ft
      • Built 1957
      8 Castle Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 89 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
  • /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
    • /30

      Est $444,789

      Not Listed For Sale

      18 Castle Hill Rd, Wilmington, VT 05363

      • 5 Beds
      • 2 Baths
      • 2,295 Sq Ft
      • Built 1840
      18 Castle Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 163 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
  • /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 $497,259

    Last Listing Agent Tobin Twelves Skihome Realty

    1 Pheasant Ln, Dover, VT 05356
    • /34

      Est $682,581

      Not Listed For Sale

      72 Castle Hill Rd, Wilmington, VT 05363

      • 4 Beds
      • 3 Baths
      • 2,148 Sq Ft
      • Built 1967
      72 Castle Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 52 Days On Market

  • /17

    $299,000

    $14K PRICE DROP
    • 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
  • /21

    $720,000

    Sold Mar 12, 2026

    145 Shearer Hill Rd, Wilmington, VT 05363

    • 5 Beds
    • 3.5 Baths
    • 2,696 Sq Ft
    • Built 2010

    Last Sold Summary

    • 1% Below List Price
    • $267/SF
    • 36 Days On Market

    Current Estimated Value $718,656

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    145 Shearer Hill Rd, Wilmington, VT 05363
    • /18

      Est $258,213

      Not Listed For Sale

      36 Sparrow Ln, Wilmington, VT 05363

      • 5 Beds
      • 2.5 Baths
      • 2,030 Sq Ft
      • Built 1945
      36 Sparrow Ln, Wilmington, VT 05363

      Last Sold Summary

      • 112 Days On Market

  • /9

    $250,000

    $230K PRICE DROP
    • Land
    • 7.8 Acres
    • $32,051 per Acre

    16 Overlook Dr, Dover, VT 05356

    A rare opportunity to own one of the last remaining lots in the prestigious Peaks/Greenspring community! This home development site offers 7.8 acres of land with a home site featuring full panoramic mountain and woodland views to the north and east, including mountain views to undeveloped national forest land. This property is the largest and most private lot in The Peaks community, providing a

    Patricia Fitzpatrick Skihome Realty

    16 Overlook Dr, Dover, VT 05356
  • /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 $188,081

    Last Listing Agent Rob Weltz Barrett and Valley Associates Inc.

    13 Prospect St, Bellows Falls, VT 05101
    • /36

      Est $440,993

      Not Listed For Sale

      60 Hall Rd, Wilmington, VT 05363

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 2005
      60 Hall Rd, Wilmington, VT 05363

      Last Sold Summary

      • 194 Days On Market

  • /50

    $589,000

    • 3 Beds
    • 3 Baths
    • 2,144 Sq Ft

    596 Four Chimneys Rd, Grafton, VT 05146

    Tucked away near the end of a quiet dead-end country road, this charming vintage rambler offers privacy, natural beauty, and the timeless appeal of rural Vermont living. Set on more than 17 acres of open meadows, woodlands, wildflower fields, aged apple trees and two crystal-clear ponds, the property invites you to reconnect with nature in every season. Summer days are made for exploring the

    Jessica Landers Barrett and Valley Associates Inc.

    596 Four Chimneys Rd, Grafton, VT 05146
  • /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
    • /20

      Est $449,485

      Not Listed For Sale

      143 Sun and Ski Rd, Wilmington, VT 05363

      • 4 Beds
      • 2.5 Baths
      • 1,536 Sq Ft
      • Built 1972
      143 Sun and Ski Rd, Wilmington, VT 05363

      Last Sold Summary

      • 17 Days On Market

  • /11

    $585,000

    • Land
    • 36.69 Acres
    • $15,944 per Acre

    0 Pine Banks Rd Unit 5096685, Westminster, VT 05158

    Exceptional opportunity to own 36.69 acres of scenic Vermont countryside on desirable Pine Banks Road on the Westminster/Putney border. This beautiful parcel offers a rare combination of expansive open meadows, wooded privacy, and breathtaking long-range views across the Connecticut River Valley and surrounding Green Mountain foothills. The property's rolling landscape provides multiple potential

    Mickey Hipp BHG Masiello Brattleboro

    0 Pine Banks Rd Unit 5096685, Westminster, VT 05158

Showing Results 321 - 360, Page 9 of 18

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