30,790

Windham County, VT Homes

Section Image
    • /20

      Est $442,475 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

      • 11% Below List Price
      • $325/SF
      • 17 Days On Market
      • Last Sold Price $499,000
      • Nov 07, 2023

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /37

    $690,000

    • 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
  • /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 $191,093

    Last Listing Agent Angela Sherman Brattleboro Area Realty

    39 Brookside Dr Unit 5, Brattleboro, VT 05301
    • /55

      Est $294,027 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

      • 5% Above List Price
      • $213/SF
      • 73 Days On Market
      • Last Sold Price $280,000
      • Dec 20, 2024

      Last Listing Agent Donald Koelsch Deerfield Valley Real Estate

  • /40

    $675,000

    • 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
  • /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
    • /36

      Est $939,516 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

      • 2% Above List Price
      • $259/SF
      • 89 Days On Market
      • Last Sold Price $925,000
      • Oct 15, 2024

      Last Listing Agent Jacki Murano Southern Vermont Realty Group

  • /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
  • /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
    • /29

      Est $390,192 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
      • Jun 07, 2024

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /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
  • /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 $501,036

    Last Listing Agent Eric Scott Barrett & Valley Assoc. Inc

    72 Kidder Hill Rd, Grafton, VT 05146
    • /18

      Est $321,540 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
      • Aug 13, 2024

      Last Listing Agent Kristen Breeden 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
  • /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 $448,522

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

    29 First Unit 19, Wilmington, VT 05363
    • /40

      Est $683,690 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

      • 1% Above List Price
      • $260/SF
      • 5 Days On Market
      • Last Sold Price $675,000
      • Oct 04, 2023

      Last Listing Agent Jacki Murano Southern Vermont Realty Group

  • /60

    $795,000

    • 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
  • /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
    • /24

      Est $564,658 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

      • 2% Below List Price
      • $313/SF
      • 51 Days On Market
      • Last Sold Price $575,000
      • Aug 22, 2024

      Last Listing Agent Melissa Ellis Southern Vermont Realty Group

  • /20

    $195,000 Pending

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

    1499 Josh Rd, Halifax, VT 05358

    Looking for true peace and tranquility? This 46.2-acre parcel faces South/SW and is located in a gorgeous remote valley with no road noise or any sound other than the sound of the crystal-clear brook crashing down the valley and the wind in the trees! The parcel does have some improvements including a modified camper with a 1000 gallon holding tank, existing gravel driveway off Josh Road (class

    Chris Long BHG Masiello Brattleboro

    1499 Josh Rd, Halifax, VT 05358
  • /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
    • /23

      Est $209,227 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

      • 5% Above List Price
      • $74/SF
      • 2 Days On Market
      • Last Sold Price $199,000
      • Jul 12, 2024

      Last Listing Agent Jennifer Hovey-Densmore Deerfield Valley Real Estate

  • /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
  • /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 $833,667 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

      • 29% Below List Price
      • $339/SF
      • 21 Days On Market
      • Last Sold Price $1,169,000
      • Jul 26, 2024

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

  • /4

    $59,000

    • 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
  • /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 $325,407

    Last Listing Agent Terry Hill Berkshire Hathaway HomeServices Stratton Home

    150 Williams St, Londonderry, VT 05148
    • /38

      Est $398,080 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

      • 2% Above List Price
      • $303/SF
      • 12 Days On Market
      • Last Sold Price $390,000
      • Oct 15, 2024

      Last Listing Agent Erica Reynolds Southern Vermont Realty Group

  • /39

    $869,000 Under Contract

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

    6 Brumms Way, Dover, VT 05356

    Located directly across from the ski-home trail in Bears Crossing, this 2011-built home offers unbeatable access. Designed with quality and function in mind, this lodge-style retreat blends rustic charm with thoughtful modern comfort. The lot provides exceptional convenience to Mount Snow via the ski-home trail and direct shuttle service to and from the base area. Ski from the trail right to the

    Adam Palmiter Berkley & Veller Greenwood/Dover

    6 Brumms Way, Dover, VT 05356
  • /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 $383,761 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

      • 22% Above List Price
      • $155/SF
      • 290 Days On Market
      • Last Sold Price $315,000
      • Jul 12, 2024

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /37

    $289,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 936 Sq Ft

    2378 Deer Park Rd, West Halifax, VT 05358

    Set back from the road, this charming rustic cabin on 10 acres is the perfect retreat for those seeking tranquility. Enter a warm, inviting open layout with a cozy wood stove. One-level living also includes two generous bedrooms and a full bath. You have spacious front and back decks to look out onto your acres of woods. Follow a trail up to a unique, spectacular glass treehouse that is calming

    Kristen Ziter Taylor Brattleboro Area Realty

    2378 Deer Park Rd, West Halifax, VT 05358
  • /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 $394,534

    Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country

    164 Church Ave, Westminster, VT 05101
    • /33

      Est $376,014 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

      • 6% Below List Price
      • $213/SF
      • 11 Days On Market
      • Last Sold Price $398,500
      • Oct 15, 2024

      Last Listing Agent Patrice Schneider Southern Vermont Realty Group

  • /17

    $2,495,000

    • Land
    • 2.36 Acres
    • $1,057,203 per Acre

    4 Gold Medal Cir, Stratton, VT 05343

    This lot is only one mile from the Stratton Mountain Resort's Sun Bowl base area. The lot has views of Stratton's ski trails. The Powers Subdivision has 11 lots in total and 2.71 acres of common land. Additionally, there is 69 acres of conservation land making this community very private. Build your 4-bedroom dream home right here in one of the best planned communities in southern Vermont. Lot #4

    Andrew King Stratton Real Estate

    4 Gold Medal Cir, Stratton, VT 05343
  • /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
    • /38

      Est $470,094 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

      • 12% Below List Price
      • $413/SF
      • 15 Days On Market
      • Last Sold Price $535,000
      • Jul 25, 2024

      Last Listing Agent Monique White Deerfield Valley Real Estate

  • /23

    $419,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,024 Sq Ft

    1528 Townshend Rd, Grafton, VT 05146

    The Storybook Cottage is a fully renovated 1940s Cape set on over two acres along the peaceful South Branch Saxtons River, just south of historic Grafton Village. Thoughtfully scaled yet rich in character, this three bedroom home offers a warm and inviting layout with pine floors, a living room anchored by a wood stove. Nearly the entire interior has been rebuilt with new Rockwool insulation and

    Andie Fusco Four Seasons Sotheby's Int'l Realty

    1528 Townshend Rd, Grafton, VT 05146
  • /24

    $285,000 Sold Jun 12, 2025

    730 Hubbard Hill Rd, Halifax, VT 05342

    • 2 Beds
    • 2 Baths
    • 1,324 Sq Ft
    • Built 1971

    Last Sold Summary

    • 4% Above List Price
    • $215/SF
    • 8 Days On Market

    Last Listing Agent Stephanie Wilde

    730 Hubbard Hill Rd, Halifax, VT 05342
    • /38

      Est $340,245 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

      • 36% Above List Price
      • $141/SF
      • 115 Days On Market
      • Last Sold Price $250,000
      • Dec 16, 2024

      Last Listing Agent Steve Goldfarb Deerfield Valley Real Estate

Showing Results 281 - 320, Page 8 of 18

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