30,790

Windham County, VT Homes

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  • /28

    $325,000

    • 5 Beds
    • 3 Baths
    • 2,209 Sq Ft

    16 Washington St, Brattleboro, VT 05301

    Fabulous potential with this in-town home on a great neighborhood street just a few short minutes to downtown Brattleboro where you'll find shops, restaurants, galleries, and more! Close to the hospital, schools, and points north and south with easy access to Rt 91. This home retains much of the original woodwork with bulls eye trim for the doors, an elegant staircase with two stained glass

    Rebecca Seymour Brattleboro Area Realty

    16 Washington St, Brattleboro, VT 05301
  • /33

    $182,000 Sold Sep 04, 2025

    290 Old Mill Ln, Wilmington, VT 05363

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Built 1968

    Last Sold Summary

    • 27% Below List Price
    • $182/SF
    • 80 Days On Market

    Current Estimated Value $189,832

    Last Listing Agent Rich Caplan Deerfield Valley Real Estate

    290 Old Mill Ln, Wilmington, VT 05363
    • /26

      Est $241,283 Not Listed For Sale

      45 Reese Cir, Bellows Falls, VT 05101

      • 3 Beds
      • 2 Baths
      • 1,400 Sq Ft
      • Built 1987
      45 Reese Cir, Bellows Falls, VT 05101

      Last Sold Summary

      • 3% Below List Price
      • $178/SF
      • 5 Days On Market
      • Last Sold Price $249,900
      • Nov 03, 2023

      Last Listing Agent Emily Lagerberg R.H. Thackston & Company

  • /43

    $625,000

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

    15 Bills Rd, West Wardsboro, VT 05360

    This spacious five-bedroom, three-bath Cape-style home offers a wonderful Vermont retreat, ideally located just minutes from the Stratton Mountain Resort Sun Bowl and the scenic Grout Pond Recreation Area, and only about 10 minutes from Mount Snow Resort. With immediate access to nearby snowmobile trails, it’s perfectly suited for year-round outdoor enthusiasts. Nicely landscaped yard with

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    15 Bills Rd, West Wardsboro, VT 05360
  • /40

    $370,000 Sold Jan 07, 2026

    254 Boynton Rd Unit 3, Londonderry, VT 05148

    • 3 Beds
    • 2.5 Baths
    • 1,874 Sq Ft
    • Built 1987

    Last Sold Summary

    • 2% Below List Price
    • $197/SF
    • 14 Days On Market

    Last Listing Agent Beth Vickers Vermont Real Estate Company

    254 Boynton Rd Unit 3, Londonderry, VT 05148
    • /24

      Est $202,394 Not Listed For Sale

      28 Hyde St, Bellows Falls, VT 05101

      • 6 Beds
      • 2 Baths
      • 2,823 Sq Ft
      • Built 1953
      28 Hyde St, Bellows Falls, VT 05101

      Last Sold Summary

      • 20,239,300% Above List Price
      • $0/SF
      • 26 Days On Market
      • Last Sold Price $1
      • Feb 09, 2024

      Last Listing Agent Mike Redmond EXP Realty

  • /60

    $3,995,000

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

    816 Black Bear Rd, Jamaica, VT 05343

    Set atop the Vermont hillside with stunning views, offering 4 bedrooms with additional sleeping rooms accommodating up to 16 family and friends. A custom-built home by The Wadsworth Design Build/Vermont Barns is an example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    816 Black Bear Rd, Jamaica, VT 05343
  • /54

    $585,000 Sold Mar 19, 2026

    87 Townshend Rd, Grafton, VT 05146

    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft
    • Built 1874

    Last Sold Summary

    • 16% Below List Price
    • $325/SF
    • 196 Days On Market

    Current Estimated Value $502,944

    Last Listing Agent Erin McCormick KW Vermont

    87 Townshend Rd, Grafton, VT 05146
    • /40

      Est $225,529 Not Listed For Sale

      11 Steuben St, Bellows Falls, VT 05101

      • 3 Beds
      • 1 Bath
      • 1,182 Sq Ft
      • Built 1957
      11 Steuben St, Bellows Falls, VT 05101

      Last Sold Summary

      • 8% Below List Price
      • $207/SF
      • 4 Days On Market
      • Last Sold Price $245,000
      • Sep 16, 2024

      Last Listing Agent Kerry Dawson Ridgeline Real Estate

  • /9

    $430,000

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

    1950 N Main St, Londonderry, VT 05148

    It is possible to live rent- or mortgage-free — and here’s your opportunity.This fully rented, three-unit multi-family property is already generating income. Live in one unit and let the other two cover your expenses, or bring your own vision to life in this premier location. Zoned for both commercial and residential use, the possibilities are extensive. Imagine a riverfront restaurant with

    Wilkie Bushby TPW Real Estate

    1950 N Main St, Londonderry, VT 05148
  • /33

    $340,000 Sold Oct 24, 2025

    134 Vt Route 30, Newfane, VT 05345

    • 3 Beds
    • 1.5 Baths
    • 1,152 Sq Ft
    • Built 1965

    Last Sold Summary

    • 4% Above List Price
    • $295/SF
    • 8 Days On Market

    Current Estimated Value $336,757

    Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

    134 Vt Route 30, Newfane, VT 05345
    • /18

      Est $238,037 Not Listed For Sale

      6 Bramley Way, Bellows Falls, VT 05101

      • 3 Beds
      • 1.5 Baths
      • 1,254 Sq Ft
      • Built 1955
      6 Bramley Way, Bellows Falls, VT 05101

      Last Sold Summary

      • 6% Above List Price
      • $179/SF
      • 7 Days On Market
      • Last Sold Price $224,000
      • Oct 27, 2023

      Last Listing Agent Susan Colby Susan J. Colby Real Estate

  • /4

    $55,000

    • Land
    • 1.05 Acres
    • $52,381 per Acre

    31 Woodsman Rd, West Dover, VT 05356

    Lovely wooded building site not far from the Mount Snow ski resort, nearby lakes, villages, shopping, and dining. The Woodsman development features large private home sites affording great privacy with thick tree buffers, public sewer hookups, easy access of a paved road nearby and tremendous site potential. This lot has been priced to sell!

    Adam Palmiter Berkley & Veller Greenwood/Dover

    31 Woodsman Rd, West Dover, VT 05356
  • /24

    $64,000 Sold Sep 29, 2025

    2080 Vermont 30, Jamaica, VT 05343

    • 2 Beds
    • 1 Bath
    • 936 Sq Ft
    • Built 1975

    Last Sold Summary

    • 8% Below List Price
    • $68/SF
    • 5 Days On Market

    Last Listing Agent TG Glazer Winhall Real Estate

    2080 Vermont 30, Jamaica, VT 05343
    • /29

      Est $329,479 Not Listed For Sale

      11 Crotty Dr, Bellows Falls, VT 05101

      • 3 Beds
      • 2.5 Baths
      • 1,300 Sq Ft
      • Built 1985
      11 Crotty Dr, Bellows Falls, VT 05101

      Last Sold Summary

      • 1% Above List Price
      • $250/SF
      • 19 Days On Market
      • Last Sold Price $325,000
      • Dec 15, 2023

      Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

  • /32

    $299,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,750 Sq Ft

    91 Happy Haven Rd, Wilmington, VT 05363

    A solid home in a great location in Wilmington Vermont! Currently set up as a duplex. Live in one and rent the other or have family close by! Add internal stairs and use as one! This is a classic Chalet with the ease of a metal roof, large deck, 2 bedrooms and a full bathroom upstairs along with a cathedral ceiling, cute sleeping loft and built ins! The lower level is 2 bedrooms and a full

    Steve Goldfarb Deerfield Valley Real Estate

    91 Happy Haven Rd, Wilmington, VT 05363
  • /11

    $615,000 Sold Apr 15, 2026

    18 Ober Tal Dr Unit F32, Stratton, VT 05360

    • 2 Beds
    • 2 Baths
    • 1,050 Sq Ft
    • Built 1980

    Last Sold Summary

    • 3% Below List Price
    • $586/SF
    • 0 Days On Market

    Current Estimated Value $611,333

    Last Listing Agent Edwin Kevil Stratton Real Estate

    18 Ober Tal Dr Unit F32, Stratton, VT 05360
    • /36

      Est $288,260 Not Listed For Sale

      1 Colony Rd, Bellows Falls, VT 05101

      • 4 Beds
      • 1.5 Baths
      • 1,536 Sq Ft
      • Built 1941
      1 Colony Rd, Bellows Falls, VT 05101

      Last Sold Summary

      • 1% Below List Price
      • $189/SF
      • 12 Days On Market
      • Last Sold Price $290,000
      • Jul 06, 2023

      Last Listing Agent Heather Gleim CENTURY 21 North East

  • /20

    $785,000

    • 2 Beds
    • 2 Baths
    • 975 Sq Ft

    761 Stratton Mountain Rd Unit 437, Stratton, VT 05155

    Professionally renovated and redecorated Two bedroom, Two bath in ever popular Long Trail. Top floor corner with lots of light and sunshine! Spacious, open air deck overlooks the Commons and the Pond! Expanded kitchen with a large island, beautiful countertops, stainless appliances---and all new cabinetry! And Hardwood Flooring! Custom lighting throughout. Air conditioned! Includes a

    Edwin Kevil Stratton Real Estate

    761 Stratton Mountain Rd Unit 437, Stratton, VT 05155
  • /18

    $410,000 Sold Nov 06, 2025

    36 Spruce St, Brattleboro, VT 05301

    • 3 Beds
    • 2 Baths
    • 2,074 Sq Ft
    • Built 1845

    Last Sold Summary

    • 9% Below List Price
    • $198/SF
    • 183 Days On Market

    Current Estimated Value $396,751

    Last Listing Agent Christine Lewis Brattleboro Area Realty

    36 Spruce St, Brattleboro, VT 05301
    • /27

      Est $248,075 Not Listed For Sale

      17 Main St, Saxtons River, VT 05154

      • 4 Beds
      • 2.5 Baths
      • 1,690 Sq Ft
      • Built 1840
      17 Main St, Saxtons River, VT 05154

      Last Sold Summary

      • 11% Below List Price
      • $166/SF
      • 224 Days On Market
      • Last Sold Price $280,000
      • Aug 29, 2024

      Last Listing Agent Heidi Bernier Berkley & Veller Greenwood Country

  • /26

    $32,000

    • 1 Bed
    • 2 Baths
    • 791 Sq Ft

    249/251 Qtr 3 Grand Summit Way Unit 249/251 Qtr 3, Dover, VT 05356

    Trailside, best ski in/out mountain location. A really comfortable unit sleep 8. Unit 251 includes a kitchenette, comfortable living room setting, a sleep sofa a Murphy bed and full bath. Unit 249 boasts 2 queen size beds a full bathroom, and a deck with views of the mountain to enjoy skiers on the slope and fireworks. Just imagine entertaining family and friends! Benefits of ownership include

    Sheila Joyce-Albano Skihome Realty

    249/251 Qtr 3 Grand Summit Way Unit 249/251 Qtr 3, Dover, VT 05356
  • /14

    $250,000 Sold Oct 31, 2025

    70 Arbor Hill Commons Unit 15, Brattleboro, VT 05301

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • Built 1995

    Last Sold Summary

    • $200/SF
    • 5 Days On Market

    Current Estimated Value $251,022

    Last Listing Agent Robert Doyle Berkley & Veller Greenwood Country

    70 Arbor Hill Commons Unit 15, Brattleboro, VT 05301
    • /26

      Est $221,521 Not Listed For Sale

      614 Rockingham Rd, Bellows Falls, VT 05101

      • 2 Beds
      • 1 Bath
      • 1,017 Sq Ft
      • Built 1950
      614 Rockingham Rd, Bellows Falls, VT 05101

      Last Sold Summary

      • 10% Below List Price
      • $241/SF
      • 6 Days On Market
      • Last Sold Price $245,000
      • Jul 23, 2024

      Last Listing Agent Steve Schoppmeyer BHG Masiello Brattleboro

  • /2

    $150,000

    • Land
    • 2.05 Acres
    • $73,171 per Acre

    00 Fort Dummer Heights, Brattleboro, VT 05301

    Beautiful high meadow, in a nice little neighborhood tucked up against the state park, what more could you want? Easy to build!!! The land is open, so no fuss with a lot of prep. This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor cooperation.

    Christine Lewis Brattleboro Area Realty

    00 Fort Dummer Heights, Brattleboro, VT 05301
  • /8

    $87,000 Sold Nov 17, 2025

    00 Fisch Rd, Brattleboro, VT 05301

    • Land
    • 34.77 Acres
    • $2,502 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 7 Days On Market

    Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country

    00 Fisch Rd, Brattleboro, VT 05301
    • /35

      Est $357,652 Not Listed For Sale

      14 Webb Terrace, Bellows Falls, VT 05101

      • 4 Beds
      • 3 Baths
      • 2,449 Sq Ft
      • Built 1883
      14 Webb Terrace, Bellows Falls, VT 05101

      Last Sold Summary

      • 18% Below List Price
      • $178/SF
      • 121 Days On Market
      • Last Sold Price $435,000
      • Nov 28, 2023

      Last Listing Agent Heather Gleim CENTURY 21 North East

  • /5

    $72,000 Under Contract

    • Land
    • 6.21 Acres
    • $11,594 per Acre

    0 Crane Mountain Rd, Townshend, VT 05353

    Nestled on top of Townshend Acres this 6.21 acre surveyed lot offers a amazing opportunity to build your dream home . This mostly level wooded parcel has easy access to a town-maintained road near a neighborhood community . Outdoor activities abound ; hiking , hunting , snowmobiling all available ...outside your door. Minutes from four seasons resorts for skiing, music and biking. Convenient to

    Janet Lucier Barrett & Valley Assoc. Inc

    0 Crane Mountain Rd, Townshend, VT 05353
  • /21

    $18,500 Sold Mar 05, 2026

    243/245 qtr 2, Grand Summit Way Unit 243/245, Dover, VT 05356

    • 1 Bed
    • 2 Baths
    • 709 Sq Ft
    • Built 1998

    Last Sold Summary

    • 50% Below List Price
    • $26/SF
    • 214 Days On Market

    Last Listing Agent Sheila Joyce-Albano Skihome Realty

    243/245 qtr 2, Grand Summit Way Unit 243/245, Dover, VT 05356
    • /38

      Est $336,306 Not Listed For Sale

      426 Missing Link Rd, Bellows Falls, VT 05101

      • 3 Beds
      • 1.5 Baths
      • 2,248 Sq Ft
      • Built 1852
      426 Missing Link Rd, Bellows Falls, VT 05101

      Last Sold Summary

      • 1% Below List Price
      • $151/SF
      • 19 Days On Market
      • Last Sold Price $340,000
      • Nov 22, 2024

      Last Listing Agent Heather Gleim CENTURY 21 North East

  • /5

    $380,000

    • 6 Beds
    • 4 Baths
    • 3,264 Sq Ft

    25 Cottage St, Brattleboro, VT 05301

    Sweet neighborhood. This would be a great location for an owner to live in one unit and rent the other 3. Lots of character! Great investment possibility. Close to Hospital, nursing homes, shopping, interstate for travel. Plenty of off street parking

    Christine Lewis Brattleboro Area Realty

    25 Cottage St, Brattleboro, VT 05301
  • /46

    $668,000 Sold Aug 12, 2025

    395 Hillwinds Rd, Brattleboro, VT 05301

    • 4 Beds
    • 2.5 Baths
    • 2,226 Sq Ft
    • Built 1985

    Last Sold Summary

    • 3% Above List Price
    • $300/SF
    • 7 Days On Market

    Current Estimated Value $649,218

    Last Listing Agent Desiree Stango Berkley & Veller Greenwood Country

    395 Hillwinds Rd, Brattleboro, VT 05301
    • /40

      Est $334,638 Not Listed For Sale

      355 Missing Link Rd, Bellows Falls, VT 05101

      • 3 Beds
      • 2 Baths
      • 2,033 Sq Ft
      • Built 1780
      355 Missing Link Rd, Bellows Falls, VT 05101

      Last Sold Summary

      • 10% Below List Price
      • $182/SF
      • 32 Days On Market
      • Last Sold Price $370,000
      • Apr 09, 2024

      Last Listing Agent Heather Gleim CENTURY 21 North East

  • /44

    $550,000

    • 4 Beds
    • 2 Baths
    • 2,580 Sq Ft

    1229 Sheldon Hill Rd, Wardsboro, VT 05355

    Nestled among the trees in the sought-after Snow Mountain Farms community, this beautifully maintained four-bedroom home is just 7.6 miles to Mount Snow and 13 miles to Stratton Mountain Resort.The welcoming front porch leads to a spacious wrap around deck, creating an ideal setting for entertaining or simply enjoying the peaceful natural surroundings. The main living area features pine

    Jessica Citera Cummings & Co

    1229 Sheldon Hill Rd, Wardsboro, VT 05355
  • /2

    $525,000 Sold May 16, 2025

    135 Upper Dummerston Rd, Brattleboro, VT 05301

    • 5 Beds
    • 3.5 Baths
    • 3,600 Sq Ft
    • Built 1910

    Last Sold Summary

    • 19% Below List Price
    • $146/SF
    • 269 Days On Market

    Current Estimated Value $527,775

    Last Listing Agent Susan LeCours Barrett & Valley Assoc. Inc

    135 Upper Dummerston Rd, Brattleboro, VT 05301
    • /25

      Est $382,585 Not Listed For Sale

      9 Old River Rd, Bellows Falls, VT 05101

      • 3 Beds
      • Built 1973
      9 Old River Rd, Bellows Falls, VT 05101

      Last Sold Summary

      • 2% Above List Price
      • $154/SF
      • 172 Days On Market
      • Last Sold Price $375,000
      • Apr 18, 2024

      Last Listing Agent Emily Lagerberg R.H. Thackston & Company

  • /36

    $269,000

    • 1 Bed
    • 1 Bath
    • 2,000 Sq Ft

    116 Birge St Unit 3, Brattleboro, VT 05301

    Huge price reduction! Welcome to Esteyville! Here, history, location, and distinctiveness excel. This rare, NYC loft-style condo on the 3rd and 4th floors was formerly home to Estey Organ, the world's largest pipe organ manufacturer, circa 1870. Listed in the National Registry of Historic Places, you will find original pine wide-plank floors, exposed post-and-beam construction, soaring ceilings,

    Liz LaVorgna Brattleboro Area Realty

    116 Birge St Unit 3, Brattleboro, VT 05301
  • /23

    $93,999 Sold Jul 14, 2025

    8 Deepwood Park, Brattleboro, VT 05301

    • 3 Beds
    • 2 Baths
    • 880 Sq Ft
    • Built 2024

    Last Sold Summary

    • $107/SF
    • 118 Days On Market

    Last Listing Agent Kate Barry EXP Realty

    8 Deepwood Park, Brattleboro, VT 05301
    • /15

      Est $351,089 Not Listed For Sale

      157 Parker Hill Rd, Bellows Falls, VT 05101

      • 2 Beds
      • 2 Baths
      • 1,450 Sq Ft
      • Built 1978
      157 Parker Hill Rd, Bellows Falls, VT 05101

      Last Sold Summary

      • 10% Below List Price
      • $269/SF
      • 67 Days On Market
      • Last Sold Price $390,000
      • Sep 01, 2023

      Last Listing Agent Gale Alger

  • /54

    $759,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 3,100 Sq Ft

    365 Timson Hill Rd, Newfane, VT 05345

    Escape to the summit of Newfane. This secluded mountain-top retreat offers unparalleled 180-degree views of lush valleys and distant peaks—a front-row seat to nature's most stunning sunrises. The grounds are a masterpiece of landscaping, featuring sprawling fern fields, a cedar-fenced cottage garden, mature plantings, and winding brick pathways. The residence seamlessly blends artistic charm with

    Thomas Dahlin Berkley & Veller Greenwood Country

    365 Timson Hill Rd, Newfane, VT 05345

Showing Results 561 - 600, Page 15 of 18

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