31,018

Windham County, VT Homes

Section Image
  • /39

    $1,610,000

    Sold Jul 24, 2026

    47B Sun Bowl Ridge Rd, Stratton, VT 05155

    • 4 Beds
    • 3.5 Baths
    • 2,698 Sq Ft
    • Built 2001

    Last Sold Summary

    • 1% Above List Price
    • $597/SF
    • 8 Days On Market

    Last Listing Agent Jamie Luke TPW Real Estate

    47B Sun Bowl Ridge Rd, Stratton, VT 05155
    • /11

      Not Listed For Sale

      3960 Jacksonville Stage Rd, West Halifax, VT 05358

      3960 Jacksonville Stage Rd, West Halifax, VT 05358

      Last Sold Summary

      • 6 Days On Market

  • /2

    $185,000

    Under Contract
    • 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 $1,076,756

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

    339 Coldbrook Rd, Wilmington, VT 05363
    • /3

      Est $1,025,563

      Not Listed For Sale

      28 Airport Rd, Dover, VT 05356

      • 4 Beds
      • 3.5 Baths
      • 4,230 Sq Ft
      • Built 2004
      28 Airport Rd, Dover, VT 05356

      Last Sold Summary

      • 0 Days On Market

  • /41

    $289,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

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

    Adjusted to $289,000 making this the best value in Dover Green. 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

    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 $431,883

    Last Listing Agent Jacki Murano Southern Vermont Realty Group

    210 Burrington Hill Rd, Whitingham, VT 05361
    • /9

      Not Listed For Sale

      0 Parker Hill Rd, Bellows Falls, VT 05101

      0 Parker Hill Rd, Bellows Falls, VT 05101

      Last Sold Summary

      • 284 Days On Market

  • /37

    $1,250,000

    Open Sun 10AM - 2PM
    • 4 Beds
    • 3 Baths
    • 2,022 Sq Ft

    564 Goodaleville Rd, Jamaica, VT 05343

    OPEN HOUSE SUNDAY, JULY 26, FROM 10:00 AM TO 2:00 PM.This beautifully reimagined former schoolhouse blends timeless Vermont character with thoughtful modern updates. Built around the historic Goodaleville Road schoolhouse with a timber-frame addition, and renovated by Vermont Country Builders, the home reflects exceptional craftsmanship, energy efficiency, and enduring design. Just 10 minutes

    Cheyanne Pugliese

    564 Goodaleville Rd, Jamaica, VT 05343
  • /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
    • /5

      Est $75,825

      Not Listed For Sale

      29 Woodsman Rd, West Dover, VT 05356

      29 Woodsman Rd, West Dover, VT 05356

      Last Sold Summary

      • 25 Days On Market

  • /36

    $575,000

    Pending
    • 4 Beds
    • 4 Baths
    • 1,211 Sq Ft

    9 Beaver Pond Ln, Jamaica, VT 05343

    Rare Multi-Dwelling Retreat with Endless Possibilities A truly exceptional and meticulously maintained property featuring three separate residences on one beautifully landscaped lot—a setup buyers often dream about but rarely find. The main residence is a stylish 2-bedroom, 2-bath contemporary home thoughtfully designed for comfortable living. Built with sustainability in mind, the home features

    Helen Nault

    9 Beaver Pond Ln, Jamaica, VT 05343
  • /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 $337,896

    Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

    138 Cedar St, Brattleboro, VT 05301
    • /12

      Est $621,583

      Not Listed For Sale

      58 Oak St, Brattleboro, VT 05301

      • 3 Beds
      • 2 Baths
      • 3,400 Sq Ft
      • Built 1867
      58 Oak St, Brattleboro, VT 05301

      Last Sold Summary

      • 20 Days On Market

  • /17

    $150,000

    $51K PRICE DROP Pending
    • 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
  • /2

    $370,000

    Sold Jul 17, 2026

    292 Tallwood Cir, Londonderry, VT 05148

    • 4 Beds
    • 3 Baths
    • 1,720 Sq Ft
    • Built 1970

    Last Sold Summary

    • 2% Below List Price
    • $215/SF
    • 81 Days On Market

    Current Estimated Value $380,898

    Last Listing Agent The Malley Group KW Vermont

    292 Tallwood Cir, Londonderry, VT 05148
    • /39

      Not Listed For Sale

      18 Bellows Falls Rd, Putney, VT 05346

      • 5 Beds
      • 3 Baths
      • 2,650 Sq Ft
      • Built 1870
      18 Bellows Falls Rd, Putney, VT 05346

      Last Sold Summary

      • 322 Days On Market

  • /54

    $385,000

    $15K PRICE DROP
    • 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

    Victoria Woods Brattleboro Area Realty

    410 School St, Westminster, VT 05158
  • /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 $179,406

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    461 Deer Run, Putney, VT 05346
    • /22

      Not Listed For Sale

      0 Bills Rd, Stratton, VT 05360

      0 Bills Rd, Stratton, VT 05360

      Last Sold Summary

      • 119 Days On Market

  • /15

    $349,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,218 Sq Ft

    13 Sunne Village Ln, Dover, VT 05356

    Charming efficient chalet just south of the Mount Snow ski resort and ready for turn key enjoyment. This convenient location has MOOver shuttle service at the end of the street to and from the mountain, easy access to great restaurants and coffee shops, and direct snowmobile trail access, in addition to ample parking and privacy. The home has been lovingly maintained with some recent updates. As

    Adam Palmiter Berkley & Veller Greenwood/Dover

    13 Sunne Village Ln, Dover, VT 05356
  • /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 $1,778,000

    Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    97 N Brookwood Rd, Stratton, VT 05360
    • /32

      Not Listed For Sale

      432 Route 121, Westminster, VT 05158

      • 6 Beds
      • 2 Baths
      • 2,899 Sq Ft
      • Built 1903
      432 Route 121, Westminster, VT 05158

      Last Sold Summary

      • 148 Days On Market

  • /39

    $475,000

    $44K PRICE DROP
    • Land
    • 80.11 Acres
    • $5,929 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
    • /3

      Est $410,450

      Not Listed For Sale

      394 Canal St, Brattleboro, VT 05301

      • Studio
      • 2 Baths
      • 2,863 Sq Ft
      • Built 1930
      394 Canal St, Brattleboro, VT 05301

      Last Sold Summary

      • 0 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

    $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
    • /40

      Est $561,051

      Not Listed For Sale

      1084 Cyrus Rd, Whitingham, VT 05361

      • 3 Beds
      • 4 Baths
      • 2,200 Sq Ft
      • Built 2005
      1084 Cyrus Rd, Whitingham, VT 05361

      Last Sold Summary

      • 129 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
  • /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
    • /32

      Est $598,812

      Not Listed For Sale

      110 Beaver Pond Rd, Dummerston, VT 05301

      • 3 Beds
      • 2.5 Baths
      • 2,280 Sq Ft
      • Built 2008
      110 Beaver Pond Rd, Dummerston, VT 05301

      Last Sold Summary

      • 9 Days On Market

  • /26

    $1,100,000

    • 4 Beds
    • 3 Baths
    • 2,800 Sq Ft

    48A Hammer Beam Loop Unit 48A, Dover, VT 05356

    Stunning post-and-beam townhome at the base of Mount Snow ski resort. Built in 2007 and completely renovated for turnkey enjoyment, this exceptional unit offers a style and scale rarely found this close to the mountain. Rustic natural woodwork runs throughout, a product of the exposed post-and-beam construction that gives the home its unmistakable character. The open-concept main living level

    Adam Palmiter Berkley & Veller Greenwood/Dover

    48A Hammer Beam Loop Unit 48A, Dover, VT 05356
  • /24

    $680,000

    Sold Apr 22, 2026

    761 Stratton Mountain Access Rd Unit 322, Stratton, VT 05360

    • 2 Beds
    • 2 Baths
    • 1,020 Sq Ft
    • Built 1998

    Last Sold Summary

    • $667/SF
    • 6 Days On Market

    Last Listing Agent Andrew King Stratton Real Estate

    761 Stratton Mountain Access Rd Unit 322, Stratton, VT 05360
    • /40

      Est $433,797

      Not Listed For Sale

      392 Old Stage Rd, West Halifax, VT 05358

      • 1 Bed
      • 1 Bath
      • 1,416 Sq Ft
      • Built 2001
      392 Old Stage Rd, West Halifax, VT 05358

      Last Sold Summary

      • 6 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
  • /27

    $1,300,000

    Sold Jul 31, 2025

    0 W Hill Rd S Unit 5006431, Jamaica, VT 05343

    • Land
    • 591 Acres
    • $2,200 per Acre

    Last Sold Summary

    • 32% Below List Price
    • 136 Days On Market

    Last Listing Agent Timothy Apps Four Seasons Sotheby's Int'l Realty

    0 W Hill Rd S Unit 5006431, Jamaica, VT 05343
    • /4

      Est $497,740

      Not Listed For Sale

      255 Minard Rd, Putney, VT 05346

      • 3 Beds
      • 2.5 Baths
      • 2,958 Sq Ft
      • Built 1986
      255 Minard Rd, Putney, VT 05346

      Last Sold Summary

      • 0 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
  • /2

    $499,000

    Sold Oct 23, 2025

    72 Kidder Hill Rd, Grafton, VT 05146

    • 4 Beds
    • 3.5 Baths
    • 3,301 Sq Ft
    • Built 1750

    Last Sold Summary

    • $151/SF
    • 25 Days On Market

    Current Estimated Value $563,505

    Last Listing Agent Eric Scott Barrett & Valley Assoc. Inc

    72 Kidder Hill Rd, Grafton, VT 05146

Showing Results 241 - 280, Page 7 of 18

How to Buy a Home How to Finance a Home How to Sell a Home