30,889

Windham County, VT Homes

Section Image
  • /33

    $289,000

    • 4 Beds
    • 1.5 Baths
    • 1,638 Sq Ft

    36 Green St, Bellows Falls, VT 05101

    Nestled in a sought-after neighborhood, this 4 bedroom, 1 1⁄2 bath cape offers a perfect blend of comfort, character and convenience. The bright and spacious living room has a fireplace with insert ideal for supplemental heating, while offering a lovely space for relaxing evenings. The large multi-pane picture window frames a lovely view of the spacious back yard while allowing for an abundance

    Wilma Skovinski Berkley & Veller Greenwood Country

    36 Green St, Bellows Falls, VT 05101
  • /60

    $639,000

    Sold Jan 09, 2026

    38 Greenspring Rd, Dover, VT 05356

    • 3 Beds
    • 3.5 Baths
    • 2,472 Sq Ft
    • Built 1990

    Last Sold Summary

    • 1% Below List Price
    • $258/SF
    • 66 Days On Market

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

    38 Greenspring Rd, Dover, VT 05356
    • /26

      Est $415,565

      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

  • /8

    $48,000

    $4K PRICE DROP
    • 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
  • /32

    $18,000

    Sold Nov 14, 2025

    111, Qtr 3, 89 Grand Summit Way, Dover, VT 05356

    • 1 Bed
    • 1 Bath
    • 608 Sq Ft
    • Built 1998

    Last Sold Summary

    • 10% Below List Price
    • $30/SF
    • 37 Days On Market

    Last Listing Agent Patricia Fitzpatrick Skihome Realty

    111, Qtr 3, 89 Grand Summit Way, Dover, VT 05356
    • /37

      Est $506,222

      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

  • /60

    $650,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,408 Sq Ft

    75 Westminster Rd, Putney, VT 05346

    This charming historic Colonial just moments from Putney Village, blends timeless character with thoughtful updates. This 4-bedroom, 3-bath home features a spacious, open kitchen highlighted by an antique brick hearth, perfect for gathering and entertaining. The flexible floor plan includes a first-floor bedroom with an ensuite full bath and its own separate entrance, offering excellent potential

    Rebecca Hiam Southern Vermont Realty Group

    75 Westminster Rd, Putney, VT 05346
  • /56

    $325,000

    Sold Jun 25, 2025

    24 Blackberry Lane Private, Dover, VT 05356

    • 3 Beds
    • 1.5 Baths
    • 1,400 Sq Ft
    • Built 2024

    Last Sold Summary

    • 35% Below List Price
    • $232/SF
    • 212 Days On Market

    Last Listing Agent Erica Reynolds Southern Vermont Realty Group

    24 Blackberry Lane Private, Dover, VT 05356
    • /40

      Est $2,250,270

      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

  • /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
  • /29

    $358,000

    Sold May 14, 2026

    160 Sunny Acres Rd, Brattleboro, VT 05301

    • 3 Beds
    • 2 Baths
    • 2,160 Sq Ft
    • Built 1952

    Last Sold Summary

    • 7% Above List Price
    • $166/SF
    • 3 Days On Market

    Current Estimated Value $333,270

    Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

    160 Sunny Acres Rd, Brattleboro, VT 05301
    • /22

      Est $392,874

      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

  • /42

    $525,000

    • 3 Beds
    • 1 Bath
    • 1,508 Sq Ft

    147 Gilbert Rd, Guilford, VT 05301

    This sweet home is nestled in the serene, and quiet location of Gilbert Rd, a dead end, located on the edge of Newfane but in the quaint town of Marlboro, VT. It has been completely renovated within the past few years by a local high-end builder with an eye for energy efficiency. His workmanship is evident in the renovation. The result: this pristine home gleams with its fresh and inviting

    Monica Sumner BHG Masiello Brattleboro

    147 Gilbert Rd, Guilford, VT 05301
  • /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
    • /24

      Est $609,219

      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

  • /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
  • /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 $286,153

    Last Listing Agent Rebecca Seymour Brattleboro Area Realty

    91 Carriage Hill Rd, Brattleboro, VT 05301
    • /29

      Est $346,978

      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

  • /2

    $185,000

    • 6 Beds
    • 2 Baths
    • 2,008 Sq Ft

    65 Williams Street Extension, Town of Rockingham, VT 05101

    Nicely cared for two family on a quiet dead end street within walking distance to the village and all that that includes, shopping, restaurants, movie theater, library and more! Each unit has three bedrooms, spacious kitchens, living room, a porch and includes washer and dryer in each unit. As an owner occupied property or an investment opportunity this is worth a look as there have been many

    Oona Madden Berkley & Veller Greenwood Country

    65 Williams Street Extension, Town of Rockingham, VT 05101
  • /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 $1,073,506

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

    339 Coldbrook Rd, Wilmington, VT 05363
    • /53

      Est $410,008

      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

  • /36

    $304,000

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    8E Dover Green Loop Unit 8E Dover Green Loop, Dover, VT 05356

    Enjoy the best of Southern Vermont from this beautiful townhome in the sought-after Dover Green community, located just minutes south of Mount Snow. Whether you're looking for a year-round residence, a low-maintenance second home, or the perfect Vermont getaway, this spacious 3-bedroom, 2-bath home offers comfort, convenience, and exceptional value. Nestled near the top of the development, this

    Donald Koelsch Deerfield Valley Real Estate

    8E Dover Green Loop Unit 8E Dover Green Loop, Dover, VT 05356
  • /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 $429,993

    Last Listing Agent Jacki Murano Southern Vermont Realty Group

    210 Burrington Hill Rd, Whitingham, VT 05361
    • /33

      Est $384,695

      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

  • /17

    $150,000

    $51K PRICE DROP
    • Land
    • 2.8 Acres
    • $53,571 per Acre

    37 Fred Houghton Rd, Putney, VT 05346

    Just in time! So special! This unusual offering was a beloved family complex for many years. The land is a delight of mixed hardwoods and evergreens, easy to walk and gently rolling for intrigue. Walk to "downtown" Putney for the small town energy, pop in the auto for a short drive to everything else...interstate access, NH, skiing...hospitals and services.....or tuck in at home for a private get

    Christine Lewis Brattleboro Area Realty

    37 Fred Houghton Rd, Putney, VT 05346
  • /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
    • /30

      Est $393,980

      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

  • /53

    $400,000

    • 3 Beds
    • 1 Bath
    • 1,852 Sq Ft

    410 School St, Westminster, VT 05158

    This historic creamery beautifully preserves the charm and craftsmanship of its 1860s origins, featuring soaring vaulted ceilings, exposed hand-hewn beams, and rich wood floors that radiate warmth and character throughout. A welcoming wraparound porch, adorned with hanging baskets and alive with birdsong, invites you to slow down and stay awhile. Inside, the open-concept living, dining, and

    Christine Lewis Brattleboro Area Realty

    410 School St, Westminster, VT 05158
  • /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 $330,944

    Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

    138 Cedar St, Brattleboro, VT 05301
    • /34

      Est $673,909

      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

  • /21

    $19,000

    $5K PRICE DROP
    • 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
  • /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 $489,039

    Last Listing Agent Alison Cummings Cummings & Co

    132 Pingree Park Ln, Londonderry, VT 05148
    • /18

      Est $294,880

      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

  • /42

    $1,150,000

    • 4 Beds
    • 1 Bath
    • 1,972 Sq Ft

    2245 Burrington Hill Rd, Whitingham, VT 05361

    Lovely 1800s vintage dairy farm on 100+ acres in the heart of Whitingham Vermont, just a short driving to nearby country villages, lakes, skiing, and more. Conveniently just over the MA border sits this amazing property which has been in the same family for 2 generations. Nestled on the crest of rolling pasture, you are treated to long range three state mountain views including Mount Monadnock to

    Michael Purcell Berkley & Veller Greenwood/Dover

    2245 Burrington Hill Rd, Whitingham, VT 05361
  • /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 $161,504

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    461 Deer Run, Putney, VT 05346
    • /36

      Est $437,851

      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

  • /35

    $339,000

    $11K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,460 Sq Ft

    6795 Vt Route 100, Londonderry, VT 05148

    Motivated sellers! 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

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    6795 Vt Route 100, Londonderry, VT 05148
  • /54

    $1,875,000

    Sold May 08, 2026

    97 N Brookwood Rd, Stratton, VT 05360

    • 4 Beds
    • 4.5 Baths
    • 2,486 Sq Ft
    • Built 1968

    Last Sold Summary

    • 9% Below List Price
    • $754/SF
    • 170 Days On Market

    Current Estimated Value $1,620,250

    Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    97 N Brookwood Rd, Stratton, VT 05360
    • /20

      Est $452,250

      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

  • /36

    $489,000

    $10K PRICE DROP
    • 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

Showing Results 241 - 280, Page 7 of 18

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