30,689

Windham County, VT Homes

Section Image
    • /36

      Est $447,923 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

      • 12% Above List Price
      • $297/SF
      • 194 Days On Market

      Last Sold Price $399,000

      Last Listing Agent Meg Streeter Meg Streeter Real Estate

  • /21

    $725,000 Under Contract

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

    145 Shearer Hill Rd, Wilmington, VT 05363

    Beautiful 2010 post and beam home just a short drive from the Mount Snow Ski Resort and village of Wilmington. This meticulous turn key home was built with quality in mind, is very energy efficient and sits on a on a private 5+ acre parcel abutting a stream just up from Spruce Lake. Inside is a gorgeous great room space with vaulted ceilings and exposed natural woodwork, great natural light

    Adam Palmiter Berkley & Veller Greenwood/Dover

    145 Shearer Hill Rd, Wilmington, VT 05363
  • /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
    • /20

      Est $460,388 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

      • 8% Below List Price
      • $325/SF
      • 17 Days On Market

      Last Sold Price $499,000

      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
  • /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
    • /55

      Est $304,229 Not Listed For Sale

      70 Sun and Ski Rd, Wilmington, VT 05363

      • 3 Beds
      • 2 Baths
      • 1,312 Sq Ft
      • Built 1965
      70 Sun and Ski Rd, Wilmington, VT 05363

      Last Sold Summary

      • 9% Above List Price
      • $213/SF
      • 73 Days On Market

      Last Sold Price $280,000

      Last Listing Agent Donald Koelsch Deerfield Valley Real Estate

  • /21

    $24,000

    • 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
  • /23

    $180,000 Sold May 23, 2025

    39 Brookside Dr Unit 5, Brattleboro, VT 05301

    • 2 Beds
    • 1 Bath
    • 930 Sq Ft
    • Built 1966

    Last Sold Summary

    • $194/SF
    • 49 Days On Market

    Current Estimated Value $189,913

    Last Listing Agent Angela Sherman Brattleboro Area Realty

    39 Brookside Dr Unit 5, Brattleboro, VT 05301
    • /36

      Est $927,449 Not Listed For Sale

      72 Aldrich Rd, Wilmington, VT 05363

      • 7 Beds
      • 5 Baths
      • 3,574 Sq Ft
      • Built 1850
      72 Aldrich Rd, Wilmington, VT 05363

      Last Sold Summary

      • $259/SF
      • 89 Days On Market

      Last Sold Price $925,000

      Last Listing Agent Jacki Murano Southern Vermont Realty Group

  • /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
  • /31

    $79,000 Sold May 07, 2025

    527 Vermont 121, Westminster, VT 05101

    • 2 Beds
    • 1.5 Baths
    • 1,477 Sq Ft
    • Built 1903

    Last Sold Summary

    • 41% Below List Price
    • $53/SF
    • 44 Days On Market

    Last Listing Agent Nick Sicard EXP Realty

    527 Vermont 121, Westminster, VT 05101
    • /29

      Est $391,159 Not Listed For Sale

      259 Vt Route 100 N, Wilmington, VT 05363

      • 5 Beds
      • 3 Baths
      • 1,100 Sq Ft
      • Built 1965
      259 Vt Route 100 N, Wilmington, VT 05363

      Last Sold Summary

      • 15% Below List Price
      • $416/SF
      • 139 Days On Market

      Last Sold Price $457,650

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /36

    $499,000

    • Land
    • 41 Acres
    • $12,171 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
  • /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
    • /18

      Est $323,404 Not Listed For Sale

      57 Riverside Dr, Wilmington, VT 05363

      • 3 Beds
      • 2 Baths
      • 1,564 Sq Ft
      • Built 1977
      57 Riverside Dr, Wilmington, VT 05363

      Last Sold Summary

      • 1% Above List Price
      • $204/SF
      • 72 Days On Market

      Last Sold Price $319,000

      Last Listing Agent Kristen Breeden Southern Vermont Realty Group

  • /2

    $199,000

    • 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 and Golf Course and The Hermitage Club close to the Coldbrook. Built to sleep 32 People. 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
  • /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 $549,827

    Last Listing Agent Eric Scott Barrett & Valley Assoc. Inc

    72 Kidder Hill Rd, Grafton, VT 05146
    • /40

      Est $693,080 Not Listed For Sale

      143 Ray Hill Rd, Wilmington, VT 05363

      • 3 Beds
      • 3.5 Baths
      • 2,600 Sq Ft
      • Built 1996
      143 Ray Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 3% Above List Price
      • $260/SF
      • 5 Days On Market

      Last Sold Price $675,000

      Last Listing Agent Jacki Murano Southern Vermont Realty Group

  • /28

    $1,395,000

    • 4 Beds
    • 4.5 Baths
    • 3,476 Sq Ft

    3B Freestyle Cir, Dover, VT 05356

    Trailside luxury at the base of the Mount Snow ski resort just off the Snowdance ski trail. This spectacular 2016 unit is just about as close and turn key as you can find. Amazing convenience to the mountain thanks to direct ski trail access, affording the ability to stop by to warm up or get a bite, yet with easterly views and a size usually only found in off mountain properties. The large

    Adam Palmiter Berkley & Veller Greenwood/Dover

    3B Freestyle Cir, Dover, VT 05356
  • /29

    $430,000 Sold Apr 24, 2025

    29 First Unit 19, Wilmington, VT 05363

    • 3 Beds
    • 3.5 Baths
    • 1,985 Sq Ft
    • Built 1988

    Last Sold Summary

    • 2% Below List Price
    • $217/SF
    • 78 Days On Market

    Current Estimated Value $441,023

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

    29 First Unit 19, Wilmington, VT 05363
    • /24

      Est $580,976 Not Listed For Sale

      252 Ray Hill Rd, Wilmington, VT 05363

      • 3 Beds
      • 2 Baths
      • 1,836 Sq Ft
      • Built 1986
      252 Ray Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 1% Above List Price
      • $313/SF
      • 51 Days On Market

      Last Sold Price $575,000

      Last Listing Agent Melissa Ellis Southern Vermont Realty Group

  • /37

    $730,000

    • 5 Beds
    • 3 Baths
    • 2,635 Sq Ft

    341 Under the Mountain Rd, Londonderry, VT 05148

    Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly

    Andy Reed Four Seasons Sotheby's Int'l Realty

    341 Under the Mountain Rd, Londonderry, VT 05148
  • /20

    $79,000 Sold May 05, 2025

    6 Thistle Hill Rd, Brattleboro, VT 05301

    • 2 Beds
    • 1 Bath
    • 784 Sq Ft
    • Built 1986

    Last Sold Summary

    • $101/SF
    • 8 Days On Market

    Last Listing Agent Victoria Woods Brattleboro Area Realty

    6 Thistle Hill Rd, Brattleboro, VT 05301
    • /23

      Est $230,402 Not Listed For Sale

      290 Ray Hill Rd, Wilmington, VT 05363

      • 8 Beds
      • Built 1850
      290 Ray Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 16% Above List Price
      • $74/SF
      • 2 Days On Market

      Last Sold Price $199,000

      Last Listing Agent Jennifer Hovey-Densmore Deerfield Valley Real Estate

  • /29

    $425,000

    • 4 Beds
    • 1 Bath
    • 1,730 Sq Ft

    83 Depot St, Jamaica, VT 05343

    Step back in time while enjoying modern comforts in this lovingly restored 1800s farmhouse with attached barn, set in the heart of Southern Vermont. Rich with historic character, the home features original wide pine floors, plaster walls, a slate roof, and classic architectural lines that reflect Vermont’s timeless heritage.The private backyard offers a peaceful setting to relax, gather

    Carrie Mathews Winhall Real Estate

    83 Depot St, Jamaica, VT 05343
  • /16

    $600,000 Sold Nov 07, 2025

    761 Stratton Mountain Access Rd Unit 240, Stratton, VT 05360

    • 2 Beds
    • 2 Baths
    • 916 Sq Ft
    • Built 1999

    Last Sold Summary

    • 6% Below List Price
    • $655/SF
    • 198 Days On Market

    Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

    761 Stratton Mountain Access Rd Unit 240, Stratton, VT 05360
    • /40

      Est $464,000 Not Listed For Sale

      69 Woods Rd, Wilmington, VT 05363

      • 4 Beds
      • 4 Baths
      • 3,448 Sq Ft
      • Built 2005
      69 Woods Rd, Wilmington, VT 05363

      Last Sold Summary

      • 60% Below List Price
      • $339/SF
      • 21 Days On Market

      Last Sold Price $1,169,000

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

  • /54

    $695,000

    • 6 Beds
    • 3 Baths
    • 2,740 Sq Ft

    1161 Little Pond Rd, Londonderry, VT 05148

    Set along a quintessential Vermont country road just moments from the pristine waters of Lowell Lake, this versatile property offers the rare opportunity to enjoy peaceful rural living with flexible multi-family potential. Surrounded by natural beauty and year-round recreation, the setting is both private and convenient to all that Londonderry has to offer. The home features approximately 2,700

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    1161 Little Pond Rd, Londonderry, VT 05148
  • /53

    $339,000 Sold Nov 07, 2025

    150 Williams St, Londonderry, VT 05148

    • 3 Beds
    • 2.5 Baths
    • 1,304 Sq Ft
    • Built 1962

    Last Sold Summary

    • 8% Below List Price
    • $260/SF
    • 71 Days On Market

    Current Estimated Value $354,579

    Last Listing Agent Terry Hill Berkshire Hathaway HomeServices Stratton Home

    150 Williams St, Londonderry, VT 05148
    • /38

      Est $406,890 Not Listed For Sale

      369 Route 9 W, Wilmington, VT 05363

      • 4 Beds
      • 2 Baths
      • 1,288 Sq Ft
      • Built 1968
      369 Route 9 W, Wilmington, VT 05363

      Last Sold Summary

      • 4% Above List Price
      • $303/SF
      • 12 Days On Market

      Last Sold Price $390,000

      Last Listing Agent Erica Reynolds Southern Vermont Realty Group

  • /60

    $650,000

    • 4 Beds
    • 4 Baths
    • 2,978 Sq Ft

    23 Brook Rd, Saxtons River, VT 05154

    Includes 1-Year Home Warranty. A Distinctive Country Retreat on 6.8± private acres in the heart of the historic village of Saxtons River. This idyllic country estate offers year-round views, exquisite perennial gardens, & two beautifully integrated wings—the timeless Cape & the charming Carriage House. Inside of the Cape wing is a sunlit eat-in kitchen, KraftMaid cherry cabinetry & Silestone

    Isabella Luhrs BHG Masiello Keene

    23 Brook Rd, Saxtons River, VT 05154
  • /40

    $224,900 Sold Oct 10, 2025

    11F Snow Tree Ln Unit F, Dover, VT 05356

    • 1 Bed
    • 2 Baths
    • 848 Sq Ft
    • Built 1984

    Last Sold Summary

    • 2% Below List Price
    • $265/SF
    • 96 Days On Market

    Last Listing Agent Chad Lackey Deerfield Valley Real Estate

    11F Snow Tree Ln Unit F, Dover, VT 05356
    • /29

      Est $405,017 Not Listed For Sale

      39 Stone Brook Rd, Wilmington, VT 05363

      • 5 Beds
      • 3 Baths
      • 2,028 Sq Ft
      • Built 1956
      39 Stone Brook Rd, Wilmington, VT 05363

      Last Sold Summary

      • 29% Above List Price
      • $155/SF
      • 290 Days On Market

      Last Sold Price $315,000

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /17

    $449,000

    • 3 Beds
    • 3 Baths
    • 1,726 Sq Ft

    4A Suntec Loop Unit 4A, Dover, VT 05356

    Beautiful woodsy Suntec townhome just down from the base of the Mount Snow ski resort. This spacious 3 bedroom plus loft townhome sits about a mile south of Mount Snow, with direct access to snowmobile trails, and easy access to the nearby village of Wilmington and lakes. The unit has a large open concept floor plan with living room with wood burning fireplace and brick hearth, rustic wood

    Adam Palmiter Berkley & Veller Greenwood/Dover

    4A Suntec Loop Unit 4A, Dover, VT 05356
  • /33

    $385,000 Sold Jul 15, 2025

    164 Church Ave, Westminster, VT 05101

    • 3,489 Sq Ft
    • Built 1900

    Last Sold Summary

    • 4% Above List Price
    • $110/SF
    • 66 Days On Market

    Current Estimated Value $431,208

    Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country

    164 Church Ave, Westminster, VT 05101
    • /33

      Est $372,010 Not Listed For Sale

      574 Higley Hill Rd, Wilmington, VT 05363

      • 3 Beds
      • 1 Bath
      • 1,872 Sq Ft
      • Built 1760
      574 Higley Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 7% Below List Price
      • $213/SF
      • 11 Days On Market

      Last Sold Price $398,500

      Last Listing Agent Patrice Schneider Southern Vermont Realty Group

  • /33

    $249,000

    • 2 Beds
    • 1 Bath
    • 1,004 Sq Ft

    662 Vt Route 30, Newfane, VT 05345

    Whether you’re just starting out with your first home or looking to downsize and simplify, this sweet home is just the right size. It features two bedrooms plus bonus room upstairs, with a full bathroom conveniently located on the first floor. The kitchen is charming, complete with a dishwasher, newer refrigerator and stove, opens to a dining area, and a spacious living room with beautiful wood

    Rebecca Seymour Brattleboro Area Realty

    662 Vt Route 30, Newfane, VT 05345
  • /31

    $240,000 Sold Jun 26, 2025

    15 Mountain Village Unit 231, West Dover, VT 05356

    • 2 Beds
    • 2 Baths
    • 860 Sq Ft
    • Built 1987

    Last Sold Summary

    • 11% Below List Price
    • $279/SF
    • 163 Days On Market

    Last Listing Agent Kim Meeker Southern Vermont Realty Group

    15 Mountain Village Unit 231, West Dover, VT 05356
    • /35

      Est $406,313 Not Listed For Sale

      42 Old Town Rd, Wilmington, VT 05363

      • 3 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 1962
      42 Old Town Rd, Wilmington, VT 05363

      Last Sold Summary

      • 29% Above List Price
      • $210/SF
      • 13 Days On Market

      Last Sold Price $315,000

      Last Listing Agent Rich Caplan Deerfield Valley Real Estate

Showing Results 281 - 320, Page 8 of 18

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