30,889

Windham County, VT Homes

Section Image
  • /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
    • /55

      Est $298,249

      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

  • /2

    $174,900

    $24K PRICE DROP
    • 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, The Golf Course and The Hermitage Club close to the Coldbrook. Built as a post and beam home. 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
  • /19

    $255,000

    Sold Jul 15, 2025

    130 Beechnut Ln, Putney, VT 05346

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1980

    Last Sold Summary

    • 9% Above List Price
    • $221/SF
    • 54 Days On Market

    Current Estimated Value $246,604

    Last Listing Agent John Hatton Berkley & Veller Greenwood Country

    130 Beechnut Ln, Putney, VT 05346
    • /36

      Est $984,910

      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

  • /60

    $469,000

    $31K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    47 Upper Howes Way Unit A-23, Wilmington, VT 05363

    On the Hill, end of the Road, double lot, brand new house with attached garage. If this is what you have been waiting for, wait no more! 2024 modular construction home with 3 bedrooms, 2 baths, one bedroom has an ensuite bath, the other 2 bedrooms share a full bath. Dining area has a slier to the deck out back, and it has a secluded feel of almost complete privacy. Enjoy all the amenities Chimney

    Sigrid Pickering Chimney Hill Realty

    47 Upper Howes Way Unit A-23, 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
    • /29

      Est $403,086

      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

  • /37

    $690,000

    $40K PRICE DROP
    • 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
  • /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
    • /18

      Est $326,922

      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

  • /40

    $665,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,100 Sq Ft

    47 Oak Hill Dr, Dummerston, VT 05301

    Tucked away on a private road, this impeccably maintained 3-bedroom, 2-bathroom home sits on a serene 6-acre lot, offering the perfect blend of privacy and comfort. Set well back from the road, the property provides a peaceful retreat surrounded by nature. Inside, you’ll find a bright and inviting open-concept layout designed for both everyday living and entertaining. The spacious living and

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    47 Oak Hill Dr, Dummerston, VT 05301
  • /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 $680,422

      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

  • /54

    $649,000

    $56K PRICE DROP
    • 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
  • /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
    • /24

      Est $579,233

      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

  • /36

    $975,000

    Under Contract
    • 4 Beds
    • 4 Baths
    • 2,800 Sq Ft

    7 Overbrook Dr, Dover, VT 05356

    Experience luxury mountain living in this stunning 4-bedroom, 4-bath townhome with breathtaking views of Mount Snow. Spanning three spacious levels, this exceptional home blends rustic elegance with modern comfort, offering the perfect Vermont escape for every season.The main level showcases a dramatic floor-to-ceiling fieldstone fireplace with an efficient pellet stove, creating a warm and

    Patricia Fitzpatrick Skihome Realty

    7 Overbrook Dr, Dover, VT 05356
  • /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 $500,475

    Last Listing Agent Eric Scott Barrett & Valley Assoc. Inc

    72 Kidder Hill Rd, Grafton, VT 05146
    • /23

      Est $214,859

      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

  • /60

    $650,000

    $45K PRICE DROP
    • 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
  • /35

    $510,000

    Sold Apr 17, 2026

    104 Karen Day Rd, Halifax, VT 05342

    • 4 Beds
    • 1 Bath
    • 1,560 Sq Ft
    • Built 1860

    Last Sold Summary

    • 12% Below List Price
    • $327/SF
    • 127 Days On Market

    Last Listing Agent Chris Long BHG Masiello Brattleboro

    104 Karen Day Rd, Halifax, VT 05342
    • /40

      Est $878,000

      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

      • 21 Days On Market

  • /7

    $75,000

    • Land
    • 20.8 Acres
    • $3,606 per Acre

    0 Hunter Brook Rd, Marlboro, VT 05344

    *Please do not go onto the neighbors driveways.* Deep into Marlboro, on a seasonal rd, set up camp and fall asleep to the white noise of the brook. The campsite is flat, right off the road and then the land slopes upward. At the back there is a shared pond site.Hunter Brook Rd is not maintained in the wintertime, from the Marlboro side; you'll need to snowmobile, ski or walk in.

    Victoria Woods Brattleboro Area Realty

    0 Hunter Brook Rd, Marlboro, VT 05344
  • /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
    • /38

      Est $413,027

      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

  • /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 the development having 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

    Adam Palmiter Berkley & Veller Greenwood/Dover

    4A Suntec Loop Unit 4A, Dover, VT 05356
  • /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 $319,906

    Last Listing Agent Terry Hill Berkshire Hathaway HomeServices Stratton Home

    150 Williams St, Londonderry, VT 05148
    • /29

      Est $438,660

      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

  • /60

    $795,000

    Under Contract
    • 4 Beds
    • 3.5 Baths
    • 3,212 Sq Ft

    104 Juniper Ridge Rd, Brattleboro, VT 05301

    Welcome to Juniper Ridge! Where you will find superior craftsmanship, a private haven, and neighbors only one can dream of. As you enter the foyer of this custom built home, you'll feel its character & elegance with vaulted ceilings, arched doorways, terracotta tile and balconies lined with bookshelves. The home was built with attention to the flow, energy and natural light. The kitchen has

    Kristen Ziter Taylor Brattleboro Area Realty

    104 Juniper Ridge Rd, Brattleboro, VT 05301
  • /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
    • /33

      Est $391,093

      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

  • /8

    $74,900

    • Land
    • 1.1 Acres
    • $68,091 per Acre

    2 Johnson Hill, Dover, VT 05356

    Private 1.10 +/- Acre lot in Dover Hills VT. #WW-2-2888 Permit in place. Trinity Engineering did the engineering and the lot was approved for a three bedroom dwelling.

    Janet Boyd Boyd Real Estate

    2 Johnson Hill, 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 $378,936

    Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country

    164 Church Ave, Westminster, VT 05101
    • /38

      Est $440,605

      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

  • /28

    $425,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,510 Sq Ft

    49 West Rd, Wilmington, VT 05363

    Lovely renovated chalet at the bottom of the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. This lovely private parcel sits in the easily accessible lower section with nice seclusion and views out the rear, affording nice privacy yet with all the conveniences of community living. The interior boasts an open concept living space with natural light and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    49 West Rd, Wilmington, VT 05363
  • /28

    $277,000

    Sold Apr 23, 2026

    15 West St, Brattleboro, VT 05301

    • 4 Beds
    • 1 Bath
    • 1,374 Sq Ft
    • Built 1950

    Last Sold Summary

    • 3% Above List Price
    • $202/SF
    • 5 Days On Market

    Current Estimated Value $276,384

    Last Listing Agent Liz LaVorgna Brattleboro Area Realty

    15 West St, Brattleboro, VT 05301
    • /38

      Est $333,109

      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

  • /4

    $59,000

    Under Contract
    • Land
    • 3.3 Acres
    • $17,879 per Acre

    0 Hunt Rd, Wardsboro, VT 05355

    Discover the perfect canvas for your Vermont dream home on this newly created 3.3-acre parcel in Wardsboro. Tucked away in a peaceful, private setting, you’ll enjoy the quiet beauty of the surrounding woods while still being within easy reach of some of Southern Vermont’s most sought-after destinations. Spend your winters skiing at Mount Snow or Stratton Mountain Resort, and take advantage of

    Mike Masters Four Seasons Sotheby's Int'l Realty

    0 Hunt Rd, Wardsboro, VT 05355
  • /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

Showing Results 281 - 320, Page 8 of 18

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