31,018

Windham County, VT Homes

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  • /22

    $595,000

    • 4 Beds
    • 2 Baths
    • 1,430 Sq Ft

    9 Mountain Acres Rd, Jamaica, VT 05343

    Completely renovated and move-in ready, this stunning mountain home offers the perfect blend of comfort and convenience. The full interior renovation includes a brand-new kitchen and bathroom (as well as an updated second bath) , updated bedrooms, new doors, fresh paint, and beautiful new flooring throughout. A propane fireplace adds warmth and charm, while a newly installed mini-split system

    Carrie Mathews Winhall Real Estate

    9 Mountain Acres Rd, Jamaica, VT 05343
  • /15

    $52,000

    Sold May 15, 2026

    Lot 4 Ghastly Job Way, Wilmington, VT 05363

    • Land
    • 3.58 Acres
    • $14,525 per Acre

    Last Sold Summary

    • 31% Below List Price
    • 369 Days On Market

    Last Listing Agent Monique White Deerfield Valley Real Estate

    Lot 4 Ghastly Job Way, Wilmington, VT 05363
    • /23

      Est $319,225

      Not Listed For Sale

      123 Birdville Rd, Whitingham, VT 05361

      • 2 Beds
      • 2 Baths
      • 1,224 Sq Ft
      • Built 1971
      123 Birdville Rd, Whitingham, VT 05361

      Last Sold Summary

      • 19 Days On Market

  • /36

    $729,000

    • 3 Beds
    • 3 Baths
    • 3,400 Sq Ft

    219 Hillcrest Terrace, Brattleboro, VT 05301

    A rare combination of recreation & convenience in one of Brattleboro's most desirable neighborhoods. This home is designed for living & entertaining! The property sits on 1.6 acres of landscaped grounds with sweeping views of Mt. Wantastiquet showcasing spectacular sunrises & front-row views of Brattleboro's 4th of July fireworks. Tucked beside Living Memorial Park on a quiet cul-de-sac where

    Robert Doyle Berkley & Veller Greenwood Country

    219 Hillcrest Terrace, Brattleboro, VT 05301
  • /52

    $450,000

    Sold Jul 01, 2026

    300 Westminster West Rd, Putney, VT 05346

    • 2 Beds
    • 2 Baths
    • 1,582 Sq Ft
    • Built 1968

    Last Sold Summary

    • 7% Above List Price
    • $284/SF
    • 1 Day On Market

    Current Estimated Value $363,816

    Last Listing Agent Heidi Bernier Berkley & Veller Greenwood Country

    300 Westminster West Rd, Putney, VT 05346
    • /27

      Est $264,389

      Not Listed For Sale

      1871 Wilmington Cross Rd, Whitingham, VT 05361

      • 5 Beds
      • 2.5 Baths
      • 2,428 Sq Ft
      • Built 1840
      1871 Wilmington Cross Rd, Whitingham, VT 05361

      Last Sold Summary

      • 49 Days On Market

  • /39

    $419,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 1,972 Sq Ft

    2843 Burrington Hill Rd, Whitingham, VT 05361

    3 Bed, 3 Bath, 9+ Acres and exceptionally well cared for country retreat!Lovingly maintained & thoughtfully reimagined by the same owners for more than 20 years, every improvement has been made with care & purpose. The result is a home that feels warm, welcoming, effortlessly comfortable & beautifully connected to its surroundings. Set on 9± acres of rolling fields, mature woods & groomed

    Jacki Murano Southern Vermont Realty Group

    2843 Burrington Hill Rd, Whitingham, VT 05361
  • /41

    $364,000

    Sold Aug 15, 2025

    3091 Route 121, Windham, VT 05359

    • 4 Beds
    • 2 Baths
    • 1,758 Sq Ft
    • Built 1860

    Last Sold Summary

    • 8% Below List Price
    • $207/SF
    • 22 Days On Market

    Current Estimated Value $419,127

    Last Listing Agent Claudia Harris Mary Mitchell Miller Real Estate

    3091 Route 121, Windham, VT 05359
    • /38

      Est $792,196

      Not Listed For Sale

      1793 Faulkner Rd, Whitingham, VT 05361

      • 5 Beds
      • 2.5 Baths
      • 3,332 Sq Ft
      • Built 1830
      1793 Faulkner Rd, Whitingham, VT 05361

      Last Sold Summary

      • 53 Days On Market

  • /13

    $120,000

    • Land
    • 4.68 Acres
    • $25,641 per Acre

    8559 Vt Route 30, Jamaica, VT 05343

    Double the Lots, Half the Drama.Why buy one lot when you can have two for the price of... well, this one? Here are 4.68 acres of "ready-to-go" land. Permits are secured for a 3 bedroom house on each lot, and the septic is already there, so you don't have to spend your weekends at town hall meetings. Build on both, or build on one and sell the other to that friend who always "forgets" their

    TG Glazer Winhall Real Estate

    8559 Vt Route 30, Jamaica, VT 05343
  • /58

    $635,000

    Sold Jul 21, 2026

    142 Dover Rd, Newfane, VT 05362

    • 4 Beds
    • 2 Baths
    • 2,500 Sq Ft
    • Built 1840

    Last Sold Summary

    • 27% Above List Price
    • $254/SF
    • 2 Days On Market

    Last Listing Agent Kassie Rubico Berkley & Veller Greenwood Country

    142 Dover Rd, Newfane, VT 05362
    • /57

      Est $436,500

      Not Listed For Sale

      292 Parsons Rd, Jacksonville, VT 05342

      • 4 Beds
      • 1.5 Baths
      • 1,700 Sq Ft
      • Built 1860
      292 Parsons Rd, Jacksonville, VT 05342

      Last Sold Summary

      • 18 Days On Market

  • /34

    $460,000

    • 3 Beds
    • 2 Baths
    • 1,920 Sq Ft

    216 Ghastly Job Way, Wilmington, VT 05363

    Escape to the beauty of Vermont in this private mountain retreat, ideally situated at the end of a quiet country road. Set on a secluded parcel, this charming getaway boasts sweeping long-range views stretching across the Green Mountains and National Forest to Mount Snow, with easterly vistas toward neighboring Marlboro. Take in spectacular sunsets from the covered front porch or unwind

    Monique White Deerfield Valley Real Estate

    216 Ghastly Job Way, Wilmington, VT 05363
  • /2

    $395,000

    Sold May 11, 2026

    75 E Birch Rd Unit 35, Stratton, VT 05360

    • 2 Beds
    • 2 Baths
    • 1,119 Sq Ft
    • Built 1983

    Last Sold Summary

    • 1% Below List Price
    • $353/SF
    • 22 Days On Market

    Last Listing Agent Kristin Pirie

    75 E Birch Rd Unit 35, Stratton, VT 05360
    • /29

      Est $886,686

      Not Listed For Sale

      2329 Faulkner Rd, Whitingham, VT 05361

      • 4 Beds
      • 3 Baths
      • 2,400 Sq Ft
      • Built 1970
      2329 Faulkner Rd, Whitingham, VT 05361

      Last Sold Summary

      • 13 Days On Market

  • /31

    $680,000

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155

    Nestled right on the slopes of Stratton Mountain Resort, this two bedroom two ensuite bathroom condominium offers true ski-in/ski-out convenience for your winter getaway. You'll find yourself just steps from the Villager chairlift, beginner ski area as well as a stone's throw to the shops and restaurants in the Stratton Village. An open-concept living/dinning/kitchen area that features a stone

    Timothy Mich Doddridge Stratton Real Estate

    778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155
  • /26

    $465,000

    Sold Apr 13, 2026

    28 Country Club Rd, Dover, VT 05356

    • 4 Beds
    • 3 Baths
    • 1,776 Sq Ft
    • Built 1972

    Last Sold Summary

    • 7% Below List Price
    • $262/SF
    • 239 Days On Market

    Current Estimated Value $465,465

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    28 Country Club Rd, Dover, VT 05356
    • /21

      Est $268,696

      Not Listed For Sale

      424 Us Route 5, Putney, VT 05346

      • 4 Beds
      • 3 Baths
      • 2,005 Sq Ft
      • Built 1837
      424 Us Route 5, Putney, VT 05346

      Last Sold Summary

      • 40 Days On Market

  • /21

    $290,000

    • Land
    • 289.12 Acres
    • $1,003 per Acre

    0 Black Bear Rd Unit 5101033, Jamaica, VT 05343

    Windham Woods Forest offers 289.12 acres of productive, predominantly hardwood timberland in the scenic southern Green Mountains of Jamaica, VT, an area prized for sparse development, strong wildlife habitat, and proximity to the Green Mountain National Forest and Stratton Mountain Resort. The property boasts significant Legal Trail frontage on both Black Bear and Melis Roads and sits directly on

    Thom Milke Fountains Land Inc.

    0 Black Bear Rd Unit 5101033, Jamaica, VT 05343
  • /4

    $360,000

    Sold May 18, 2026

    1469 Higley Hill Rd, West Marlboro, VT 05363

    • 4 Beds
    • 2 Baths
    • 1,768 Sq Ft
    • Built 1973

    Last Sold Summary

    • $204/SF
    • 0 Days On Market

    Current Estimated Value $359,992

    Last Listing Agent Melissa Nebelski Real Broker LLC

    1469 Higley Hill Rd, West Marlboro, VT 05363
    • /23

      Est $485,407

      Not Listed For Sale

      279 Trail Rd, Putney, VT 05346

      • 2 Beds
      • 3 Baths
      • 3,588 Sq Ft
      • Built 1990
      279 Trail Rd, Putney, VT 05346

      Last Sold Summary

      • 57 Days On Market

  • /60

    $549,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 850 Sq Ft

    794 White Rd, Windham, VT 05359

    Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out—new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam

    Erica Reynolds Southern Vermont Realty Group

    794 White Rd, Windham, VT 05359
  • /41

    $785,000

    Sold Nov 21, 2025

    202 Pratt Bridge Rd, Jamaica, VT 05343

    • 3 Beds
    • 2.5 Baths
    • 2,800 Sq Ft
    • Built 1966

    Last Sold Summary

    • 1% Below List Price
    • $280/SF
    • 28 Days On Market

    Current Estimated Value $665,487

    Last Listing Agent Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    202 Pratt Bridge Rd, Jamaica, VT 05343
    • /19

      Est $241,821

      Not Listed For Sale

      130 Beechnut Ln, Putney, VT 05346

      • 3 Beds
      • 1 Bath
      • 1,152 Sq Ft
      • Built 1980
      130 Beechnut Ln, Putney, VT 05346

      Last Sold Summary

      • 54 Days On Market

  • /44

    $475,000

    • 6 Beds
    • 2.5 Baths
    • 3,682 Sq Ft

    4303 Hinesburg Rd, Brattleboro, VT 05301

    Private! Guilford! This unusual combination of a true log home with an incredible center double sided chimney....a fireplace facing the kitchen/dining and wood stove in the living room, bringing the best of both worlds:... ambience and warmth. There is a surprise of one more fireplace on the 2nd floor in the charming primary bedroom...use the ensuite for a huge walk in closet. The other half of

    Christine Lewis Brattleboro Area Realty

    4303 Hinesburg Rd, Brattleboro, VT 05301
  • /52

    $280,000

    Sold Jun 04, 2026

    9 Tuttle St, Bellows Falls, VT 05101

    • 4 Beds
    • 2.5 Baths
    • 2,546 Sq Ft
    • Built 1921

    Last Sold Summary

    • 7% Below List Price
    • $110/SF
    • 9 Days On Market

    Current Estimated Value $294,740

    Last Listing Agent Lisa Stone Keller Williams Realty Metro-Keene

    9 Tuttle St, Bellows Falls, VT 05101
    • /26

      Est $373,590

      Not Listed For Sale

      331 Old Codding Rd, Putney, VT 05346

      • 3 Beds
      • 2 Baths
      • 1,818 Sq Ft
      • Built 2005
      331 Old Codding Rd, Putney, VT 05346

      Last Sold Summary

      • 5 Days On Market

  • /60

    $999,000

    $101K PRICE DROP
    • 3,374 Sq Ft

    85 Route 100, West Dover, VT 05356

    Southern Vermont's fully renovated Mount Snow income compound: five separately metered rentable units across four buildings on 2.57 level acres in West Dover, main-road frontage on VT Route 100, pond on site. About 5 minutes from Mount Snow Resort in the Deerfield Valley, on the ski-bus route from the mountain into Wilmington. Same-road neighbors include Gray Ghost Inn (sold $1,100,000, 2023) and

    Nick Sicard EXP Realty

    85 Route 100, West Dover, VT 05356
  • /2

    $615,000

    Sold May 11, 2026

    75 Ryan Rd, Dummerston, VT 05301

    • 4 Beds
    • 2.5 Baths
    • 2,511 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Below List Price
    • $245/SF
    • 0 Days On Market

    Current Estimated Value $602,689

    Last Listing Agent Carol Slocum Keller Williams Realty Metro-Keene

    75 Ryan Rd, Dummerston, VT 05301
    • /3

      Est $370,594

      Not Listed For Sale

      112 Sauve Rd, Putney, VT 05346

      • 3 Beds
      • 2.5 Baths
      • 3,189 Sq Ft
      • Built 1780
      112 Sauve Rd, Putney, VT 05346

      Last Sold Summary

      • 0 Days On Market

  • /37

    $595,000

    • 3 Beds
    • 3 Baths
    • 2,172 Sq Ft

    171 Green Meadow, Brattleboro, VT 05301

    Immaculate! Lovingly reimagined over two decades, this impeccable residence blends thoughtful design with modern sustainability. The heart of the home is a chef’s kitchen with ample counter space and a spacious pantry with an integrated dining area—perfect for entertaining. Relax in the stunning living room, anchored by a gas insert fireplace crafted by a very talented local mason. Outdoor living

    Thomas Dahlin Berkley & Veller Greenwood Country

    171 Green Meadow, Brattleboro, VT 05301
  • /30

    $296,000

    Sold Jun 29, 2026

    68 Westminster Terrace, Westminster, VT 05158

    • 2 Beds
    • 2 Baths
    • 1,524 Sq Ft
    • Built 1962

    Last Sold Summary

    • 4% Above List Price
    • $194/SF
    • 3 Days On Market

    Last Listing Agent Wilma Skovinski Berkley & Veller Greenwood Country

    68 Westminster Terrace, Westminster, VT 05158
    • /35

      Est $277,947

      Not Listed For Sale

      810 Sweetwood Hill, Putney, VT 05346

      • 3 Beds
      • 1 Bath
      • 1,240 Sq Ft
      • Built 1969
      810 Sweetwood Hill, Putney, VT 05346

      Last Sold Summary

      • 100 Days On Market

  • /59

    $3,495,000

    • 9 Beds
    • 11 Baths
    • 6,726 Sq Ft

    238 Stowe Hill Rd, Wilmington, VT 05363

    Green Meadows Farm is a rare Southern Vermont estate where timeless character, modern comfort, and exceptional recreational amenities come together across more than 16 picturesque acres. Just minutes from Lake Raponda, downtown Wilmington, Mount Snow, and The Hermitage Club, this remarkable property offers sweeping mountain views, stunning sunsets, and the space to create lasting memories for

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    238 Stowe Hill Rd, Wilmington, VT 05363
  • /26

    $340,000

    Sold Mar 05, 2026

    48 Villager Loop, West Dover, VT 05356

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 1986

    Last Sold Summary

    • 20% Below List Price
    • $212/SF
    • 195 Days On Market

    Current Estimated Value $343,904

    Last Listing Agent Patrice Schneider Southern Vermont Realty Group

    48 Villager Loop, West Dover, VT 05356
    • /39

      Est $369,919

      Not Listed For Sale

      3712 Us Route 5, Westminster, VT 05158

      • 4 Beds
      • 2 Baths
      • 2,423 Sq Ft
      • Built 1792
      3712 Us Route 5, Westminster, VT 05158

      Last Sold Summary

      • 14 Days On Market

  • /3

    $125,000

    $50K PRICE DROP
    • Land
    • 1.75 Acres
    • $71,429 per Acre

    0 Fort Dummer Heights Unit 4934976, Brattleboro, VT 05301

    Manicured into a beautiful high meadow, in a nice little neighborhood....sunny with views, what morecould you want? Easy to build!!! The land is open, so no fuss with a lot of prep. This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor

    Christine Lewis Brattleboro Area Realty

    0 Fort Dummer Heights Unit 4934976, Brattleboro, VT 05301
  • /46

    $415,000

    Sold Nov 07, 2025

    155 Oak Grove Ave, Brattleboro, VT 05301

    • 4 Beds
    • 2 Baths
    • 1,446 Sq Ft
    • Built 1932

    Last Sold Summary

    • 9% Above List Price
    • $287/SF
    • 7 Days On Market

    Current Estimated Value $405,667

    Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty

    155 Oak Grove Ave, Brattleboro, VT 05301
    • /19

      Est $330,982

      Not Listed For Sale

      2170 Kurn Hattin Rd, Putney, VT 05346

      • 3 Beds
      • 1 Bath
      • 1,404 Sq Ft
      • Built 1992
      2170 Kurn Hattin Rd, Putney, VT 05346

      Last Sold Summary

      • 29 Days On Market

  • /54

    $579,000

    Under Contract
    • 4 Beds
    • 2 Baths
    • 1,723 Sq Ft

    66 Upper Oak Hill Rd, Newfane, VT 05345

    180 +/- views, end of the road, top of the hill privacy. 12 acres,4 beds,2 baths,brick,beams,built-ins,custom features,screen room, bonus space! A combination increasingly difficult to find, especially minutes from Newfane Village, Rock River, Brattleboro, vibrant arts community, farm-to-table dining, local galleries, garden shops, farm markets, outdoor recreation that define this special corner

    Jacki Murano Southern Vermont Realty Group

    66 Upper Oak Hill Rd, Newfane, VT 05345

Showing Results 441 - 480, Page 12 of 18

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