31,018

Windham County, VT Homes

Section Image
  • /33

    $455,000

    Sold Mar 04, 2026

    139 Buttonwood Dr, Brattleboro, VT 05301

    • 2 Beds
    • 2 Baths
    • 1,390 Sq Ft
    • Built 2014

    Last Sold Summary

    • 4% Below List Price
    • $327/SF
    • 6 Days On Market

    Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country

    139 Buttonwood Dr, Brattleboro, VT 05301
    • /55

      Est $310,056

      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

      • 73 Days On Market

  • /44

    $799,000

    • 4 Beds
    • 4 Baths
    • 3,200 Sq Ft

    39D Dover Springs Ln, Dover, VT 05356

    Located in the highly sought-after Greensprings community at Mount Snow, this spacious 4 bedroom, 4 bath townhouse offers the perfect blend of comfort, convenience, and year-round recreation.The bright, open-concept main living area features vaulted ceilings, abundant natural light, and a cozy fireplace ideal for gathering after a day on the slopes. Large windows and sliding doors invite the

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    39D Dover Springs Ln, Dover, VT 05356
  • /38

    $650,000

    Sold Mar 03, 2026

    1382 Grassy Brook Rd, Brookline, VT 05345

    • 3 Beds
    • 2.5 Baths
    • 3,113 Sq Ft
    • Built 1985

    Last Sold Summary

    • 2% Above List Price
    • $209/SF
    • 123 Days On Market

    Last Listing Agent Thomas Dahlin Berkley & Veller Greenwood Country

    1382 Grassy Brook Rd, Brookline, VT 05345
    • /36

      Est $1,006,471

      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

      • 89 Days On Market

  • /24

    $280,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,451 Sq Ft

    461 South Rd, Brattleboro, VT 05301

    This sweet 2 bedroom, 2 bathroom home has been recently rejuvenated with a new heating system, new flooring, new kitchen cabinets and counter tops, and fresh paint inside and out, and a new septic system! There's been quite a bit done to this lovely home that's a short distance to the Marlboro town office and post office and a few minutes' ride down to Brattleboro. There's good lawn space on the

    Susan Bellville Bellville Realty

    461 South Rd, Brattleboro, VT 05301
  • /19

    $305,000

    Sold Aug 05, 2025

    85 Crosby St, Brattleboro, VT 05301

    • 3 Beds
    • 1 Bath
    • 1,500 Sq Ft
    • Built 1950

    Last Sold Summary

    • 2% Above List Price
    • $203/SF
    • 41 Days On Market

    Current Estimated Value $295,761

    Last Listing Agent Karen Hoppe Berkley & Veller Greenwood Country

    85 Crosby St, Brattleboro, VT 05301
    • /29

      Est $414,751

      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

      • 139 Days On Market

  • /39

    $279,000

    Under Contract
    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft

    98 Greenleaf St, Brattleboro, VT 05301

    Sweet ranch home with 2 car attached garage. A lovely and level lot for gardening or outdoor entertaining, this location provides a country feel but only minutes from vibrant West Brattleboro events and businesses and a short trip brings you into downtown Brattleboro with lots of opportunities. This home with a generous living/dining space, good sized kitchen, 2 bedrooms and 1 full bathroom is

    Susan Bellville Bellville Realty

    98 Greenleaf St, Brattleboro, VT 05301
  • /43

    $887,000

    Sold Oct 17, 2025

    460 Stratton Gate Rd, Jamaica, VT 05343

    • 4 Beds
    • 3 Baths
    • 3,155 Sq Ft
    • Built 1992

    Last Sold Summary

    • 1% Below List Price
    • $281/SF
    • 12 Days On Market

    Current Estimated Value $919,703

    Last Listing Agent Helen Nault

    460 Stratton Gate Rd, Jamaica, VT 05343
    • /18

      Est $327,969

      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

      • 72 Days On Market

  • /9

    $385,000

    • 7 Beds
    • 4 Baths
    • 3,551 Sq Ft

    1950 N Main St, Londonderry, VT 05148

    It is possible to live rent or mortgage free and here’s your opportunity.This fully rented, three unit multi family property is already generating income. Live in one unit and let the other two cover your expenses, or bring your own vision to life in this premier location. Zoned for both commercial and residential use, the possibilities are extensive. Imagine a riverfront restaurant with al

    Wilkie Bushby TPW Real Estate

    1950 N Main St, Londonderry, VT 05148
  • /56

    $240,000

    Sold Aug 29, 2025

    67 Morningside Commons, Guilford, VT 05301

    • 2 Beds
    • 1.5 Baths
    • 1,056 Sq Ft
    • Built 1988

    Last Sold Summary

    • 2% Above List Price
    • $227/SF
    • 19 Days On Market

    Current Estimated Value $231,649

    Last Listing Agent Sally Fegley BHG Masiello Brattleboro

    67 Morningside Commons, Guilford, VT 05301
    • /40

      Est $702,502

      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

      • 5 Days On Market

  • /3

    $500,000

    • Land
    • 1.1 Acres
    • $454,545 per Acre

    Lot 2 Mountain Ridge Estates, Wilmington, VT 05363

    Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 1.1 acres overlooking the fairway of the 18th hole and mountains

    Adam Palmiter Berkley & Veller Greenwood/Dover

    Lot 2 Mountain Ridge Estates, Wilmington, VT 05363
  • /39

    $150,000

    Sold Dec 05, 2025

    236 Hall Bridge Rd, Bellows Falls, VT 05101

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1969

    Last Sold Summary

    • 32% Below List Price
    • $156/SF
    • 38 Days On Market

    Last Listing Agent Heather Gleim CENTURY 21 North East

    236 Hall Bridge Rd, Bellows Falls, VT 05101
    • /24

      Est $596,802

      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

      • 51 Days On Market

  • /40

    $825,000

    • 5 Beds
    • 1 Bath
    • 1,224 Sq Ft

    6036 Jacksonville Stage Rd, Guilford, VT 05301

    Imagine 216 acres of rolling fields, serene woodlands, and a glowing sugarbush tucked along a quiet country dirt road near the Massachusetts border in Halifax, just a short drive to Brattleboro and Wilmington. Held by the same family for generations, this timeless Southern Vermont property includes a farmhouse, barns, and several outbuildings ,many ready for restoration, reimagining, or

    Melissa Nebelski Real Broker LLC

    6036 Jacksonville Stage Rd, Guilford, VT 05301
  • /36

    $960,000

    Sold Jun 25, 2026

    7 Overbrook Dr, Dover, VT 05356

    • 4 Beds
    • 4 Baths
    • 2,800 Sq Ft
    • Built 2009

    Last Sold Summary

    • 2% Below List Price
    • $343/SF
    • 1 Day On Market

    Last Listing Agent Patricia Fitzpatrick Skihome Realty

    7 Overbrook Dr, Dover, VT 05356
    • /23

      Est $240,756

      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

      • 2 Days On Market

  • /55

    $795,000

    $54K PRICE DROP
    • 6 Beds
    • 6.5 Baths
    • 3,877 Sq Ft

    2435 Stage Rd, Guilford, VT 05301

    Only a fortunate few have the privilege of calling Green River Village home—a quintessential Vermont hamlet distinguished by its historic covered bridge, the 1811 timber crib dam, and the iconic wood-spired church proudly perched on the hillside above. Sited next to the bridge, the Green River Bridge House, originally a blacksmith shop, enjoys 300 feet of frontage along the Green River. Built in

    John Mcpherson Berkley & Veller Greenwood Country

    2435 Stage Rd, Guilford, VT 05301
  • /27

    $245,000

    Sold Nov 14, 2025

    8365 Vt Route 30, Jamaica, VT 05343

    • 2 Beds
    • 1 Bath
    • 756 Sq Ft
    • Built 1967

    Last Sold Summary

    • 2% Below List Price
    • $324/SF
    • 0 Days On Market

    Current Estimated Value $236,680

    Last Listing Agent TG Glazer Winhall Real Estate

    8365 Vt Route 30, Jamaica, VT 05343
    • /40

      Est $927,513

      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

      • 21 Days On Market

  • /43

    $747,500

    • 5 Beds
    • 3.5 Baths
    • 3,436 Sq Ft

    67 Castle Hill Rd, Wilmington, VT 05363

    Rare opportunity to own a meticulously restored 1830s vintage farmhouse, offered completely turnkey with extensive updates, thoughtful renovations, and modern amenities throughout. Ideally located just outside the country village of Wilmington for shopping and dining, a short drive to Mount Snow, and just up the street from Lake Whitingham’s boat launch and beach areas — truly four-season

    Adam Palmiter Berkley & Veller Greenwood/Dover

    67 Castle Hill Rd, Wilmington, VT 05363
  • /10

    $145,000

    Sold Jan 06, 2026

    680 W River Rd, Brattleboro, VT 05301

    • Land
    • 8 Acres
    • $18,125 per Acre

    Last Sold Summary

    • 17% Below List Price
    • 148 Days On Market

    Last Listing Agent Chris Long BHG Masiello Brattleboro

    680 W River Rd, Brattleboro, VT 05301
    • /38

      Est $418,283

      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

      • 12 Days On Market

  • /49

    $675,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 2,670 Sq Ft

    2079 Ames Hill Rd, Marlboro, VT 05344

    Experience the perfect blend of contemporary design and natural warmth in this stunning 2-story hybrid post & beam set on 5 landscaped acres. Thoughtfully designed with soaring ceilings, exposed beams and lots of glass, this light filled retreat brings the outdoors in while offering comfort and style in every season. Inside rich hardwood floors flow throughout the open concept living spaces,

    Tamara Purcell Berkley & Veller Greenwood Country

    2079 Ames Hill Rd, Marlboro, VT 05344
  • /20

    $195,000

    Sold May 15, 2026

    1499 Josh Rd, Halifax, VT 05358

    • Land
    • 46.2 Acres
    • $4,221 per Acre

    Last Sold Summary

    • 12 Days On Market

    Last Listing Agent Chris Long BHG Masiello Brattleboro

    1499 Josh Rd, Halifax, VT 05358
    • /29

      Est $431,649

      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

      • 290 Days On Market

  • /18

    $299,000

    • Land
    • 1.06 Acres
    • $282,075 per Acre

    12 Someday Rd, Dover, VT 05356

    Located in the prestigious Someday neighborhood of West Dover,VT this 1.06-acre building lot offers a unique opportunity to create your dream home with breathtaking views of Mount Snow ski resort. The lot, which once housed the original Someday homestead as your footprint, it is now ready for its next chapter. With a permit for sewer in place for a 6-bedroom home, the property provides a head

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    12 Someday Rd, Dover, VT 05356
  • /60

    $625,000

    Sold Oct 03, 2025

    49 Tyler St, Brattleboro, VT 05301

    • 3 Beds
    • 2 Baths
    • 2,731 Sq Ft
    • Built 1880

    Last Sold Summary

    • 14% Below List Price
    • $229/SF
    • 65 Days On Market

    Current Estimated Value $669,511

    Last Listing Agent Karen Hoppe Berkley & Veller Greenwood Country

    49 Tyler St, Brattleboro, VT 05301
    • /33

      Est $394,085

      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

      • 11 Days On Market

  • /46

    $499,000

    • 3 Beds
    • 2.5 Baths
    • 1,707 Sq Ft

    16 A Snowtree Ln, Dover, VT 05356

    This exceptional townhouse in the sought-after SnowTree development offers a unique opportunity for homeownership in a community with a reliable HOA management company. Spread across three meticulously updated levels, the townhouse welcomes you with a spacious, sun-filled living room featuring a wood-burning fireplace and large windows that offer winter mountain views and allow natural light to

    Sheila Joyce-Albano Skihome Realty

    16 A Snowtree Ln, Dover, VT 05356
  • /37

    $313,000

    Sold Jan 23, 2026

    787 Vermont 30, Newfane, VT 05345

    • 2 Beds
    • 1 Bath
    • 588 Sq Ft
    • Built 1962

    Last Sold Summary

    • 11% Below List Price
    • $532/SF
    • 48 Days On Market

    Last Listing Agent TG Glazer Winhall Real Estate

    787 Vermont 30, Newfane, VT 05345
    • /38

      Est $467,573

      Not Listed For Sale

      95 Davis Dr, Wilmington, VT 05363

      • 4 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1967
      95 Davis Dr, Wilmington, VT 05363

      Last Sold Summary

      • 15 Days On Market

  • /43

    $774,000

    • 3,091 Sq Ft

    798 Vermont Route 100, Wilmington, VT 05363

    Multi-Family & Commercial Opportunity in Wilmington, VermontSet on 1.05 acres just outside Wilmington village, this versatile property offers two recently renovated apartments totaling five bedrooms, each with its own two-car garage perfect for owner occupancy, rental income, or staff housing.The main building features updated interiors with modern kitchens, stylish baths, and new

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    798 Vermont Route 100, Wilmington, VT 05363
  • /10

    $36,000

    Sold Nov 20, 2025

    00 Susan Lynn Ln, Wardsboro, VT 05355

    • Land
    • 1 Acre
    • $36,000 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 114 Days On Market

    Last Listing Agent Jessica Samples BHG Masiello Keene

    00 Susan Lynn Ln, Wardsboro, VT 05355
    • /38

      Est $347,508

      Not Listed For Sale

      21 Look Rd, Wilmington, VT 05363

      • 5 Beds
      • 3 Baths
      • 1,776 Sq Ft
      • Built 1963
      21 Look Rd, Wilmington, VT 05363

      Last Sold Summary

      • 115 Days On Market

  • /51

    $899,800

    $49K PRICE DROP
    • 5 Beds
    • 8 Baths
    • 7,430 Sq Ft

    925 Hinesburg Rd, Brattleboro, VT 05301

    Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

    Christine Lewis Brattleboro Area Realty

    925 Hinesburg Rd, Brattleboro, VT 05301
  • /39

    $850,000

    Sold May 08, 2026

    6 Brumms Way, Dover, VT 05356

    • 5 Beds
    • 3.5 Baths
    • 4,626 Sq Ft
    • Built 2011

    Last Sold Summary

    • 2% Below List Price
    • $184/SF
    • 12 Days On Market

    Current Estimated Value $848,750

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    6 Brumms Way, Dover, VT 05356

Showing Results 361 - 400, Page 10 of 18

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