30,790

Windham County, VT Homes

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  • /15

    $370,000 Sold Aug 04, 2025

    761 Stratton Mountain Access Rd Unit 231, Stratton, VT 05360

    • 1 Bed
    • 1 Bath
    • 580 Sq Ft
    • Built 1999

    Last Sold Summary

    • 13% Below List Price
    • $638/SF
    • 120 Days On Market

    Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

    761 Stratton Mountain Access Rd Unit 231, Stratton, VT 05360
    • /37

      Est $518,940 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

      • 5% Above List Price
      • $369/SF
      • 18 Days On Market
      • Last Sold Price $495,000
      • Oct 20, 2023

      Last Listing Agent Dan McKenna Cummings & Co

  • /28

    $269,000 Under Contract

    • 4 Beds
    • 1 Bath
    • 1,374 Sq Ft

    15 West St, Brattleboro, VT 05301

    Enjoy a spacious kitchen that flows seamlessly into a large living area with open views of Mount Wantastiquet. This single-level ranch offers four generously sized bedrooms and a full bath, making it ideal for those seeking one-floor living and efficient heating. A cozy woodstove in the living area helps offset heating costs while adding warmth and charm. Hardwood flooring, a beautifully tiled

    Liz LaVorgna Brattleboro Area Realty

    15 West St, Brattleboro, VT 05301
  • /27

    $285,000 Sold Dec 10, 2025

    91 Carriage Hill Rd, Brattleboro, VT 05301

    • 3 Beds
    • 1 Bath
    • 912 Sq Ft
    • Built 1975

    Last Sold Summary

    • 5% Below List Price
    • $312/SF
    • 41 Days On Market

    Current Estimated Value $285,301

    Last Listing Agent Rebecca Seymour Brattleboro Area Realty

    91 Carriage Hill Rd, Brattleboro, VT 05301
    • /40

      Est $1,121,454 Not Listed For Sale

      220 Lake Raponda Rd, Wilmington, VT 05363

      • 4 Beds
      • 2 Baths
      • 2,200 Sq Ft
      • Built 1930
      220 Lake Raponda Rd, Wilmington, VT 05363

      Last Sold Summary

      • 2% Above List Price
      • $500/SF
      • 6 Days On Market
      • Last Sold Price $1,100,000
      • Apr 28, 2023

      Last Listing Agent Donald Koelsch Deerfield Valley Real Estate

  • /8

    $48,000

    • Land
    • 6.1 Acres
    • $7,869 per Acre

    0 Cooke Rd, Brattleboro, VT 05301

    Amidst rolling VT farmland, sits these 6 acres in West Brattleboro. While there is road frontage on Rte 9, the driveway is off the class 4 section of Cooke Rd. There's about 250 feet of Cooke Rd that you would need to maintain before the town road. The ROW into the land parallels the power lines, which you cannot see when you're on the land. There a nice cleared shelf when you walk in and then

    Victoria Woods Brattleboro Area Realty

    0 Cooke Rd, Brattleboro, VT 05301
  • /54

    $1,050,000 Sold Feb 06, 2026

    339 Coldbrook Rd, Wilmington, VT 05363

    • 4 Beds
    • 3 Baths
    • 3,506 Sq Ft
    • Built 1988

    Last Sold Summary

    • 12% Below List Price
    • $299/SF
    • 170 Days On Market

    Current Estimated Value $1,100,667

    Last Listing Agent Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    339 Coldbrook Rd, Wilmington, VT 05363
    • /40

      Est $2,314,189 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

      • 13% Below List Price
      • $491/SF
      • 21 Days On Market
      • Last Sold Price $2,650,000
      • May 13, 2024

      Last Listing Agent Rich Caplan Deerfield Valley Real Estate

  • /13

    $99,000 Pending

    • Land
    • 10.05 Acres
    • $9,851 per Acre

    78 Captain Copeland Rd, Dover, VT 05341

    Set on a quiet country road, this 10+ acre parcel offers an ideal blend of privacy and convenience with easy access to Mount Snow and year-round recreation. The property is currently wooded, providing a natural setting with the potential to open up attractive mountain views. Located in a desirable area close to skiing, hiking, and outdoor activities, this land presents a great opportunity for a

    Carrie Mathews Winhall Real Estate

    78 Captain Copeland Rd, Dover, VT 05341
  • /53

    $1,525,000 Sold Sep 30, 2025

    3333 Under the Mountain Rd, Londonderry, VT 05148

    • 3 Beds
    • 3.5 Baths
    • 5,105 Sq Ft
    • Built 2003

    Last Sold Summary

    • $299/SF
    • 7 Days On Market

    Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    3333 Under the Mountain Rd, Londonderry, VT 05148
    • /22

      Est $380,618 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

      • 8% Above List Price
      • $354/SF
      • 115 Days On Market
      • Last Sold Price $353,500
      • Sep 18, 2023

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /12

    $119,000

    • Land
    • 5 Acres
    • $23,800 per Acre

    0 Banning Rd, Putney, VT 05346

    Location is key, and locations like this don't come along often. Almost at the top of Putney Mountain is this 5+/- acres of mature hard and soft woods, including red oak, birch, beech, pine and hemlock, just waiting to host your full or part time dwelling. The existing driveway, which is shared with the seller, offers access to the length of the parcel. There's a State Wastewater Permit with a

    Bill Hickok Berkley & Veller Greenwood Country

    0 Banning Rd, Putney, VT 05346
  • /45

    $429,500 Sold Feb 20, 2026

    210 Burrington Hill Rd, Whitingham, VT 05361

    • 3 Beds
    • 2 Baths
    • 1,564 Sq Ft
    • Built 2007

    Last Sold Summary

    • 2% Below List Price
    • $275/SF
    • 35 Days On Market

    Current Estimated Value $431,286

    Last Listing Agent Jacki Murano Southern Vermont Realty Group

    210 Burrington Hill Rd, Whitingham, VT 05361
    • /24

      Est $569,411 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

      • 13% Above List Price
      • $140/SF
      • 177 Days On Market
      • Last Sold Price $505,000
      • Nov 27, 2024

      Last Listing Agent Derek Greene Derek Greene

  • /2

    $25,000

    • Land
    • 26,136 Sq Ft
    • $41,667 per Acre

    28 Upper Howes Way, Wilmington, VT 05363

    Sweet Spot tucked away in a quiet corner of the Hill, ready for you to build your vacation getaway. Recent soil tests are favorable for a 3-bedroom house. Enjoy all the amenities Chimney Hill offers on its 1,200 Acre Resort Campus, including year-round swimming, seasonal tennis and pickleball, ice skating with a warming hut full of skates to use, hiking, biking, snowmobiling right from your house

    Sigrid Pickering Chimney Hill Realty

    28 Upper Howes Way, Wilmington, VT 05363
  • /18

    $335,000 Sold Jul 30, 2025

    138 Cedar St, Brattleboro, VT 05301

    • 3 Beds
    • 1 Bath
    • 1,174 Sq Ft
    • Built 1956

    Last Sold Summary

    • 3% Above List Price
    • $285/SF
    • 36 Days On Market

    Current Estimated Value $323,466

    Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

    138 Cedar St, Brattleboro, VT 05301
    • /29

      Est $334,916 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

      • 9% Below List Price
      • $225/SF
      • 76 Days On Market
      • Last Sold Price $367,500
      • May 17, 2024

      Last Listing Agent Erica Reynolds Southern Vermont Realty Group

  • /42

    $650,000 Pending

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

    299 Sunset Lake Rd, Brattleboro, VT 05301

    This exceptional 3-bedroom residence offers refined rural living with space, comfort, and stunning natural surroundings. The home features expansive open living areas, anchored by a large living room with a fireplace, creating a warm yet elegant gathering space. A newly redesigned kitchen serves as the heart of the home, perfectly suited for entertaining family and guests. Enjoy seamless

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    299 Sunset Lake Rd, Brattleboro, VT 05301
  • /43

    $490,000 Sold Jun 16, 2025

    132 Pingree Park Ln, Londonderry, VT 05148

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft
    • Built 1982

    Last Sold Summary

    • 12% Below List Price
    • $407/SF
    • 239 Days On Market

    Current Estimated Value $508,120

    Last Listing Agent Alison Cummings Cummings & Co

    132 Pingree Park Ln, Londonderry, VT 05148
    • /53

      Est $400,122 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

      • 9% Above List Price
      • $168/SF
      • 34 Days On Market
      • Last Sold Price $368,000
      • Nov 14, 2024

      Last Listing Agent Donald Koelsch Deerfield Valley Real Estate

  • /2

    $55,000

    • Land
    • 21,780 Sq Ft
    • $110,000 per Acre

    404 Fox Mountain Rd, Wilmington, VT 05363

    Top of the Hill. Build your dream home! One of 2 remaining lots on the new Fox Mt. Cul de Sac, and the only single lot. These have had recent soil tests showing the lot is suitable for a 3-bedroom home. The Lot is oriented to the Southwest, towards Bennington. Plus, enjoy all the amenities Chimney Hill, the Deerfield Valley and Southern Vermont offer including world class skiing and shredding,

    Sigrid Pickering Chimney Hill Realty

    404 Fox Mountain Rd, Wilmington, VT 05363
  • /21

    $136,000 Sold May 02, 2025

    724 Saxtons River Rd, Saxtons River, VT 05154

    • Land
    • 3.57 Acres
    • $38,095 per Acre

    Last Sold Summary

    • 9% Below List Price
    • 207 Days On Market

    Current Estimated Value $134,847

    Last Listing Agent Evan Russell Real Broker LLC

    724 Saxtons River Rd, Saxtons River, VT 05154
    • /33

      Est $374,906 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

      • $228/SF
      • 89 Days On Market
      • Last Sold Price $375,000
      • Nov 08, 2024

      Last Listing Agent Prema Fitzpatrick Real Broker LLC

  • /26

    $395,000 Under Contract

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

    135 Country Hill, Brattleboro, VT 05301

    Built in 2004 in this much-loved neighborhood, on a desirable one-way cul-de-sac, beautifully maintained, sits this 3-bedroom, 3-bath home. The first floor has a beautiful, large, eat-in kitchen, dining room, 1/2 bath, and access to a very spacious and inviting 16x16 deck ideal for family gatherings or entertaining, and a real sense of privacy. On the second floor, there is a primary bedroom with

    Neil Goldberg Brattleboro Area Realty

    135 Country Hill, Brattleboro, VT 05301
  • /2

    $155,000 Sold Aug 20, 2025

    461 Deer Run, Putney, VT 05346

    • Land
    • 18.5 Acres
    • $8,378 per Acre

    Last Sold Summary

    • 4% Above List Price
    • 11 Days On Market

    Current Estimated Value $163,312

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    461 Deer Run, Putney, VT 05346
    • /30

      Est $382,990 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

      • 26% Above List Price
      • $133/SF
      • 163 Days On Market
      • Last Sold Price $305,000
      • Nov 30, 2023

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /39

    $499,000

    • Land
    • 80.11 Acres
    • $6,229 per Acre

    47 Whites Hill Rd, Dover, VT 05341

    Escape to Your Private 80-Acre Paradise – Nature, Adventure, and Opportunity Await! Discover the perfect blend of natural beauty and endless outdoor adventure on this breathtaking 80-acre property, nestled in a peaceful and pristine setting. With towering maple trees ready for harvesting or simply to enjoy for their beauty and shade, this land offers both recreational enjoyment and income

    Joe Castaluccio Winhall Real Estate

    47 Whites Hill Rd, Dover, VT 05341
  • /35

    $610,000 Sold Mar 02, 2026

    1375 Sheldon Hill Rd, Wardsboro, VT 05355

    • 6 Beds
    • 4 Baths
    • 3,592 Sq Ft
    • Built 1971

    Last Sold Summary

    • 2% Below List Price
    • $170/SF
    • 57 Days On Market

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    1375 Sheldon Hill Rd, Wardsboro, VT 05355
    • /34

      Est $666,429 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

      • 1% Below List Price
      • $314/SF
      • 52 Days On Market
      • Last Sold Price $675,000
      • Sep 08, 2023

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /21

    $19,000

    • 1 Bed
    • 1 Bath
    • 673 Sq Ft

    222 Q1, 89 Grand Summit Way, Dover, VT 05356

    An opportunity to own at the beautiful and conveniently located trailside, Grand Summit Hotel. Enjoy the ski-on, ski-off lifestyle, while also experiencing the luxuries of hotel amenities, directly at the base of Mount Snow! This valley facing, sleep 6 unit is perfect for family, guests or great rental options. The unit features a fully-equipped kitchen, dining area and living room with a queen

    Prema Fitzpatrick Real Broker LLC

    222 Q1, 89 Grand Summit Way, Dover, VT 05356
  • /40

    $285,000 Sold May 09, 2025

    2469 Augur Hole Rd, Guilford, VT 05301

    • 2 Beds
    • 3.5 Baths
    • 1,228 Sq Ft
    • Built 1960

    Last Sold Summary

    • 3% Below List Price
    • $232/SF
    • 50 Days On Market

    Last Listing Agent Patrice Schneider Southern Vermont Realty Group

    2469 Augur Hole Rd, Guilford, VT 05301
    • /18

      Est $308,612 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

      • 263% Above List Price
      • $42/SF
      • 112 Days On Market
      • Last Sold Price $85,000
      • Oct 31, 2024

      Last Listing Agent Flex Realty Group Flex Realty

  • /35

    $350,000

    • 4 Beds
    • 3 Baths
    • 2,460 Sq Ft

    6795 Vt Route 100, Londonderry, VT 05148

    Charming Property with Endless Possibilities in Southern Vermont Nestled on 5 acres in the heart of Southern Vermont, this unique property offers the perfect blend of history, versatility, and potential. Currently operating as a successful business with fabrics, sewing machines, notions and more. This property presents an exceptional opportunity for a variety of uses –whether you’re looking to

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    6795 Vt Route 100, Londonderry, VT 05148
  • /19

    $255,000 Sold Jul 15, 2025

    130 Beechnut Ln, Putney, VT 05346

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1980

    Last Sold Summary

    • 9% Above List Price
    • $221/SF
    • 54 Days On Market

    Current Estimated Value $251,605

    Last Listing Agent John Hatton Berkley & Veller Greenwood Country

    130 Beechnut Ln, Putney, VT 05346
    • /33

      Est $312,530 Not Listed For Sale

      752 Route 9 E, Wilmington, VT 05363

      • 3 Beds
      • 1.5 Baths
      • 1,088 Sq Ft
      • Built 1953
      752 Route 9 E, Wilmington, VT 05363

      Last Sold Summary

      • 7% Above List Price
      • $268/SF
      • 72 Days On Market
      • Last Sold Price $292,000
      • Aug 30, 2023

      Last Listing Agent Kim Meeker Southern Vermont Realty Group

  • /36

    $489,000

    • Land
    • 41 Acres
    • $11,927 per Acre

    706 Vt Route 100, Stratton, VT 05360

    Exceptional New Offering! Rare 41± acres in Stratton with extraordinary 180 +/- long-range mountain views, improvements, base camp, driveway, clearings, trails, wildlife, and a substantial WOW factor. All for approx. $12,000/acre. A short drive in from paved Route 100, before the land rises further in elevation, sits the rustic 1-bed base camp overlooking open field and multiple ski

    Jacki Murano Southern Vermont Realty Group

    706 Vt Route 100, Stratton, VT 05360
  • /43

    $860,000 Sold Jan 23, 2026

    8 E Birch Rd Unit 103, Stratton, VT 05360

    • 5 Beds
    • 4 Baths
    • 2,238 Sq Ft
    • Built 1979

    Last Sold Summary

    • 7% Below List Price
    • $384/SF
    • 111 Days On Market

    Last Listing Agent Cheyanne Pugliese

    8 E Birch Rd Unit 103, Stratton, VT 05360
    • /36

      Est $432,317 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

      • 8% Above List Price
      • $297/SF
      • 194 Days On Market
      • Last Sold Price $399,000
      • Sep 15, 2023

      Last Listing Agent Meg Streeter Meg Streeter Real Estate

  • /2

    $174,900

    • 2 Beds
    • 2,710 Sq Ft

    29 Stable Rd, Wilmington, VT 05363

    The Stable Lodge was built in 1969-1970. Located near Haystack Ski Area, The Golf Course and The Hermitage Club close to the Coldbrook. Built as a post and beam home. Features 4 plus acres with ample parking. Building will need an extensive rehab. Not safe to go into the structure.

    Mark Yule BHG Masiello Brattleboro

    29 Stable Rd, Wilmington, VT 05363
  • /59

    $543,000 Sold Aug 07, 2025

    628 S Main St, Brattleboro, VT 05301

    • 5 Beds
    • 4.5 Baths
    • 5,850 Sq Ft
    • Built 2000

    Last Sold Summary

    • 1% Below List Price
    • $93/SF
    • 20 Days On Market

    Last Listing Agent Kerry Mulverhill

    628 S Main St, Brattleboro, VT 05301

Showing Results 241 - 280, Page 7 of 18

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