31,016

Windham County, VT Homes

Section Image
  • /40

    $785,000

    Under Contract
    • 3 Beds
    • 4 Baths
    • 3,086 Sq Ft

    145 Leon Stocker Dr, Stratton, VT 05360

    Set on two private, wooded acres, this inviting mountain retreat balances classic Vermont warmth with a spacious 3,986-square-foot layout featuring three comfortable bedrooms, a spacious loft area, and four bathrooms. Ideally situated for outdoor enthusiasts, the property offers close proximity to Vermont's VAST trail network, making year-round adventure easily accessible. The heart of the home

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    145 Leon Stocker Dr, Stratton, VT 05360
  • /52

    $1,600,000

    Sold Apr 06, 2026

    122 Sunbowl Ridge Rd, Stratton, VT 05360

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

    Last Sold Summary

    • 7% Below List Price
    • $593/SF
    • 153 Days On Market

    Last Listing Agent John Sikes Stratton Real Estate

    122 Sunbowl Ridge Rd, Stratton, VT 05360
    • /40

      Est $854,252

      Not Listed For Sale

      359 Chaves Rd, Londonderry, VT 05148

      • 5 Beds
      • 5 Baths
      • 6,570 Sq Ft
      • Built 1990
      359 Chaves Rd, Londonderry, VT 05148

      Last Sold Summary

      • 27 Days On Market

  • /47

    $289,000

    • 3 Beds
    • 2 Baths
    • 1,960 Sq Ft

    5 Camelot Dr, Wilmington, VT 05363

    Enjoy the perfect blend of convenience, privacy, and value with this 3-bedroom, 2-bath manufactured home offering approximately 2,000 square feet of comfortable living space. Tucked away on a nicely landscaped 0.43-acre lot, this home is perched above town, offering a peaceful setting while keeping you within walking distance of restaurants, shopping, local events, and the Moover shuttle for easy

    Chad Lackey Deerfield Valley Real Estate

    5 Camelot Dr, Wilmington, VT 05363
  • /2

    $692,000

    Sold Oct 03, 2025

    19 Village Lodge Rd Unit 207, Stratton, VT 05155

    • 2 Beds
    • 2 Baths
    • 1,663 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Below List Price
    • $416/SF
    • 0 Days On Market

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    19 Village Lodge Rd Unit 207, Stratton, VT 05155
    • /26

      Not Listed For Sale

      1 Wildwood Dr, West Brattleboro, VT 05301

      • 2 Beds
      • 1 Bath
      • 962 Sq Ft
      • Built 1977
      1 Wildwood Dr, West Brattleboro, VT 05301

      Last Sold Summary

      • 12 Days On Market

  • /26

    $1,350,000

    • 7,660 Sq Ft

    131,133,141 Green St, Brattleboro, VT 05301

    What an opportunity to own 11 units in 3 separate buildings with a fantastic rental history. Close to downtown, schools, shopping and bus routes. Very well maintained properties with 3 - two bedroom units and 8 one bedroom units. On site laundry for the convenience of tenants. Wonderful features including hardwood floors and large windows for exceptional natural light. Great porches and very

    Susan Bellville Bellville Realty

    131,133,141 Green St, Brattleboro, VT 05301
  • /38

    $109,000

    Sold Jul 30, 2025

    16 Jones Hill Rd, Newfane, VT 05362

    • 3 Beds
    • 1 Bath
    • 1,400 Sq Ft
    • Built 1938

    Last Sold Summary

    • 3% Below List Price
    • $78/SF
    • 6 Days On Market

    Current Estimated Value $155,052

    Last Listing Agent Robert Balewicz Evergreen Realty of Vermont

    16 Jones Hill Rd, Newfane, VT 05362
    • /32

      Not Listed For Sale

      97 Stratton Dr, Townshend, VT 05353

      • 5 Beds
      • 4.5 Baths
      • 3,529 Sq Ft
      • Built 1830
      97 Stratton Dr, Townshend, VT 05353

      Last Sold Summary

      • 118 Days On Market

  • /29

    $469,000

    $46K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,016 Sq Ft

    33D White Oaks Loop Unit 38, Dover, VT 05356

    Owners will consider offers. Nicely updated and uniquely private Timber Creek end-unit townhome with easy access and winter ski trail views. Ideally located directly across from the upper entrance to Mount Snow, Timber Creek offers shuttle service from your front door to the base area, along with convenient on-site management, exterior maintenance, snow removal, landscaping, and more. The

    Adam Palmiter Berkley & Veller Greenwood/Dover

    33D White Oaks Loop Unit 38, Dover, VT 05356
  • /46

    $299,000

    Sold Jan 22, 2026

    4410 Pikes Falls Rd, Jamaica, VT 05343

    • 3 Beds
    • 2 Baths
    • 2,194 Sq Ft
    • Built 1962

    Last Sold Summary

    • 5% Below List Price
    • $136/SF
    • 5 Days On Market

    Last Listing Agent Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

    4410 Pikes Falls Rd, Jamaica, VT 05343
    • /35

      Est $601,497

      Not Listed For Sale

      10 Lower Highlands Rd, Dover, VT 05356

      • 6 Beds
      • 3.5 Baths
      • 2,517 Sq Ft
      • Built 1970
      10 Lower Highlands Rd, Dover, VT 05356

      Last Sold Summary

      • 126 Days On Market

  • /37

    $325,000

    • 2 Beds
    • 2 Baths
    • 1,444 Sq Ft

    770 Westminster Heights Rd, Westminster, VT 05158

    Sitting on 2.4 open acres in Westminster, VT, this one-story home has had several recent updates including a newly renovated kitchen, a primary bathroom has been added, an outdoor patio and back porch have been built, and several widows and storm doors have been replaced. The house has some areas that need attention but will allow you to give it your own personal touch! Do you have a camper that

    Heather Gleim CENTURY 21 North East

    770 Westminster Heights Rd, Westminster, VT 05158
  • /30

    $105,000

    Sold Dec 03, 2025

    10 Taylor St, Town of Rockingham, VT 05101

    • 1,968 Sq Ft
    • Built 1910

    Last Sold Summary

    • 16% Below List Price
    • $53/SF
    • 97 Days On Market

    Current Estimated Value $160,280

    Last Listing Agent Julie Buffum Buffum Realty

    10 Taylor St, Town of Rockingham, VT 05101
    • /19

      Not Listed For Sale

      43 High Point Dr Unit D23, Stratton, VT 05360

      • 2 Beds
      • 2 Baths
      • 1,130 Sq Ft
      • Built 1983
      43 High Point Dr Unit D23, Stratton, VT 05360

      Last Sold Summary

      • 8 Days On Market

  • /51

    $729,000

    Under Contract
    • 5 Beds
    • 2 Baths
    • 2,500 Sq Ft

    268 S Wardsboro Rd, Newfane, VT 05345

    Minutes from historic Newfane Village, this handsome c 1791 Cape is a rare offering combining character, craftsmanship, and natural beauty. The stunning property features meadows, long frontage along The Smith Brook, large swimming pond, formal gardens, stone patios & walkways, and a hiking loop winding through the landscape. A handsome 2 car barn with an impressive stone foundation adds

    Robert Doyle Berkley & Veller Greenwood Country

    268 S Wardsboro Rd, Newfane, VT 05345
  • /2

    $80,000

    Sold Dec 19, 2025

    Lot #3 Peachtree Ln, Brattleboro, VT 05301

    • Land
    • 4.27 Acres
    • $18,735 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 50 Days On Market

    Last Listing Agent Desiree Stango Berkley & Veller Greenwood Country

    Lot #3 Peachtree Ln, Brattleboro, VT 05301
    • /35

      Not Listed For Sale

      7587 Westminster Rd W, Putney, VT 05346

      • 3 Beds
      • 2 Baths
      • 2,137 Sq Ft
      • Built 1987
      7587 Westminster Rd W, Putney, VT 05346

      Last Sold Summary

      • 98 Days On Market

  • /27

    $319,000

    $20K PRICE DROP Under Contract
    • 3 Beds
    • 1 Bath
    • 1,300 Sq Ft

    117 Oak Grove Ave, Brattleboro, VT 05301

    Located in one of the area’s most desirable and close-knit neighborhoods, this beautifully preserved 1929 home blends timeless character with thoughtful updates. Featuring hardwood floors, natural woodwork, custom built-ins, classic wainscoting, and a welcoming mudroom, the home retains the charm and craftsmanship buyers love. The open and inviting first floor offers generous living space and a

    Liz LaVorgna Brattleboro Area Realty

    117 Oak Grove Ave, Brattleboro, VT 05301
  • /29

    $495,000

    Sold Nov 21, 2025

    275 Pams Hill Rd, Wardsboro, VT 05355

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 1969

    Last Sold Summary

    • 4% Below List Price
    • $330/SF
    • 59 Days On Market

    Current Estimated Value $499,614

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    275 Pams Hill Rd, Wardsboro, VT 05355
    • /40

      Est $574,500

      Not Listed For Sale

      2900 Route 121 E, Grafton, VT 05146

      • 3 Beds
      • 2 Baths
      • 1,613 Sq Ft
      • Built 2006
      2900 Route 121 E, Grafton, VT 05146

      Last Sold Summary

      • 6 Days On Market

  • /43

    $575,000

    • 3 Beds
    • 2.5 Baths
    • 1,812 Sq Ft

    1 Bucket Ln, Dover, VT 05356

    Classic chalet tastefully renovated by the current owner, blending rustic charm with thoughtful modern updates. The open-concept floor plan features vaulted ceilings and exposed beams throughout the main living area. A stunning floor-to-ceiling brick fireplace with wood stove insert anchors the spacious kitchen, living and dining areas, which open to an expansive deck perfect for entertaining.

    Linda Benoit Highland Realty

    1 Bucket Ln, Dover, VT 05356
  • /49

    $625,000

    Sold Jan 15, 2026

    956 Old Cheney Rd, West Townshend, VT 05359

    • 2 Beds
    • 2 Baths
    • 2,144 Sq Ft
    • Built 1790

    Last Sold Summary

    • 14% Below List Price
    • $292/SF
    • 141 Days On Market

    Current Estimated Value $629,725

    Last Listing Agent Kim Meeker Southern Vermont Realty Group

    956 Old Cheney Rd, West Townshend, VT 05359
    • /34

      Est $831,205

      Not Listed For Sale

      5 Rice Hill Rd, Dover, VT 05341

      • 4 Beds
      • 3.5 Baths
      • 3,412 Sq Ft
      • Built 1989
      5 Rice Hill Rd, Dover, VT 05341

      Last Sold Summary

      • 108 Days On Market

  • /52

    $1,997,000

    • 4 Beds
    • 4.5 Baths
    • 3,631 Sq Ft

    14 Talon Dr, Stratton, VT 05360

    Perfectly positioned between Stratton Mountain and Mount Snow, this exceptional custom timber frame home by Wadsworth Design Build offers the best of Southern Vermont living. Tucked within a private neighborhood and backing directly to the Green Mountain National Forest, the property provides a peaceful setting with immediate access to hiking, snowshoeing, and year-round outdoor recreation right

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    14 Talon Dr, Stratton, VT 05360
  • /44

    $655,000

    Sold Sep 12, 2025

    1176 E Dover Rd, Wardsboro, VT 05355

    • 2 Beds
    • 1.5 Baths
    • 1,530 Sq Ft
    • Built 2000

    Last Sold Summary

    • 2% Above List Price
    • $428/SF
    • 7 Days On Market

    Current Estimated Value $612,349

    Last Listing Agent Thomas Dahlin Berkley & Veller Greenwood Country

    1176 E Dover Rd, Wardsboro, VT 05355
    • /33

      Est $210,312

      Not Listed For Sale

      951 Dover Rd, South Newfane, VT 05351

      • 2 Beds
      • 1 Bath
      • 1,369 Sq Ft
      • Built 1900
      951 Dover Rd, South Newfane, VT 05351

      Last Sold Summary

      • 9 Days On Market

  • /34

    $355,000

    • 4 Beds
    • 1.5 Baths
    • 2,532 Sq Ft

    9 Burt St, Bellows Falls, VT 05101

    Welcome to 9 Burt Street located on one of the prettiest streets in Bellows Falls. This opportunity offers an attractive two story 2532 sqft. family home located within the center of Bellows Falls with easy walking access to all stores, dining and schools. It is located on a beautiful street bordered by well kept family homes. The first floor includes a fireplace in the family room, a formal

    David White OwnerEntry.com

    9 Burt St, Bellows Falls, VT 05101
  • /53

    $685,000

    Sold Aug 13, 2025

    37 Spring Hill Rd, West Dover, VT 05356

    • 4 Beds
    • 5.5 Baths
    • 3,695 Sq Ft
    • Built 2005

    Last Sold Summary

    • 19% Below List Price
    • $185/SF
    • 109 Days On Market

    Current Estimated Value $667,938

    Last Listing Agent Jillian Wimmelman Deerfield Valley Real Estate

    37 Spring Hill Rd, West Dover, VT 05356
    • /24

      Not Listed For Sale

      730 Hubbard Hill Rd, Halifax, VT 05342

      • 2 Beds
      • 2 Baths
      • 1,324 Sq Ft
      • Built 1971
      730 Hubbard Hill Rd, Halifax, VT 05342

      Last Sold Summary

      • 8 Days On Market

  • /22

    $399,000

    • 9 Beds
    • 4 Baths
    • 3,286 Sq Ft

    19 Canal St, Brattleboro, VT 05301

    Located in the heart of Brattleboro, this fully occupied and consistently high-performing investment property offers an outstanding opportunity for investors seeking strong cash flow and steady rental demand. Currently configured with 9 individual rentable rooms, the property has been successfully exclusively rented to The New England Center for Circus Arts students for years and maintains an

    Karen Hoppe Berkley & Veller Greenwood Country

    19 Canal St, Brattleboro, VT 05301
  • /40

    $350,000

    Sold Jan 09, 2026

    119 Main St, Putney, VT 05346

    • 4 Beds
    • 2 Baths
    • 1,908 Sq Ft
    • Built 1798

    Last Sold Summary

    • 36% Below List Price
    • $183/SF
    • 136 Days On Market

    Current Estimated Value $359,113

    Last Listing Agent Heather Gleim CENTURY 21 North East

    119 Main St, Putney, VT 05346
    • /40

      Est $650,262

      Not Listed For Sale

      27 Haymaker Ln Unit 9A, Wilmington, VT 05363

      • 3 Beds
      • 2.5 Baths
      • 2,500 Sq Ft
      • Built 1989
      27 Haymaker Ln Unit 9A, Wilmington, VT 05363

      Last Sold Summary

      • 18 Days On Market

  • /8

    $250,000

    $230K PRICE DROP
    • Land
    • 5.08 Acres
    • $49,213 per Acre

    10 Overlook Dr, Dover, VT 05356

    A rare opportunity to own one of the last remaining lots in the prestigious Peaks/Greenspring community! This home development site offers 5.08 acres of land and features full panoramic mountain and woodland views to the south, including mountain views to undeveloped national forest land. This property is one of the most private lots in The Peaks community, providing a full immersion in the woods

    Patricia Fitzpatrick Skihome Realty

    10 Overlook Dr, Dover, VT 05356
  • /37

    $252,500

    Sold Dec 24, 2025

    2069 Fort Bridgman Rd, Vernon, VT 05354

    • 3 Beds
    • 1 Bath
    • 1,270 Sq Ft
    • Built 1920

    Last Sold Summary

    • 5% Below List Price
    • $199/SF
    • 9 Days On Market

    Current Estimated Value $253,358

    Last Listing Agent Kerry Mulverhill

    2069 Fort Bridgman Rd, Vernon, VT 05354
    • /21

      Not Listed For Sale

      724 Saxtons River Rd, Saxtons River, VT 05154

      724 Saxtons River Rd, Saxtons River, VT 05154

      Last Sold Summary

      • 207 Days On Market

  • /12

    $178,000

    $7K PRICE DROP
    • Land
    • 8 Acres
    • $22,250 per Acre

    4441 Vermont 30, Jamaica, VT 05343

    Set amidst a peaceful woodland setting, this 8.0± acre parcel offers the perfect balance of seclusion and convenience—tucked away for privacy yet easily accessible year-round.. Currently being subdivided from a larger tract, this parcel presents a rare chance to shape your vision from the ground up.A five-bedroom Wastewater Permit has been approved, and a professional boundary survey is

    Helen Nault

    4441 Vermont 30, Jamaica, VT 05343
  • /14

    $120,000

    Sold Apr 28, 2026

    60 Brookside Dr Unit 1, Brattleboro, VT 05301

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Built 1966

    Last Sold Summary

    • $171/SF
    • 6 Days On Market

    Current Estimated Value $121,295

    Last Listing Agent Morriah Adams BHG Masiello Brattleboro

    60 Brookside Dr Unit 1, Brattleboro, VT 05301
    • /40

      Not Listed For Sale

      4954 Westminster Rd W, Putney, VT 05346

      • 4 Beds
      • 1.5 Baths
      • 1,955 Sq Ft
      • Built 1979
      4954 Westminster Rd W, Putney, VT 05346

      Last Sold Summary

      • 8 Days On Market

  • /25

    $389,900

    • 2,168 Sq Ft

    88 Happy Haven Rd, Wilmington, VT 05363

    Sweet Country Retreat Near Mount Snow & The Hermitage Club Tucked away on a quiet private road in the heart of Wilmington, this charming country home offers the perfect blend of privacy, comfort, and four-season Vermont living. Just minutes from Mount Snow and the exclusive Hermitage Club, this spacious property is an ideal mountain getaway, full-time residence, or investment opportunity.

    Heidi Zizza Four Seasons Sotheby's Int'l Realty

    88 Happy Haven Rd, Wilmington, VT 05363

Showing Results 161 - 200, Page 5 of 18

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