30,790

Windham County, VT Homes

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  • /23

    $159,000

    • 1 Bed
    • 1 Bath
    • 592 Sq Ft

    219 High St Unit 3, Brattleboro, VT 05301

    Welcome to the effortless existence of condominium life with the rare addition of uniqueness. How nice to own a home while splitting the expenses with two other condo owners. Park in your driveway and follow a pretty stone path to your first-floor sanctuary. This efficient 592 sq ft space offers an open kitchen, dining area with a washer and dryer, living room, one bedroom, and a full bath. Share

    Kristen Ziter Taylor Brattleboro Area Realty

    219 High St Unit 3, Brattleboro, VT 05301
  • /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 $252,957

    Last Listing Agent Kerry Mulverhill

    2069 Fort Bridgman Rd, Vernon, VT 05354
    • /40

      Est $479,908 Not Listed For Sale

      129 Adams Hill Rd Unit 27, South Newfane, VT 05351

      • 5 Beds
      • 4 Baths
      • 2,348 Sq Ft
      • Built 1972
      129 Adams Hill Rd Unit 27, South Newfane, VT 05351

      Last Sold Summary

      • 40% Below List Price
      • $341/SF
      • 5 Days On Market
      • Last Sold Price $800,000
      • Nov 09, 2023

      Last Listing Agent Michelle O'Neil Deerfield Valley Real Estate

  • /31

    $459,000

    • 1 Bed
    • 2.5 Baths
    • 2,076 Sq Ft

    33 W Main St, Wilmington, VT 05363

    Unique opportunity to own a commercial building in the heart of downtown Wilmington. This historic structure has been completely overhauled and meticulously maintained by the current owners, and was the location of a successful restaurant for many years, with an income producing apartment upstairs. It is now being offered to a buyer with vision who may be looking for prime retail, restaurant, or

    Adam Palmiter Berkley & Veller Greenwood/Dover

    33 W Main St, Wilmington, VT 05363
  • /26

    $401,000 Sold Oct 03, 2025

    215 Old Town Rd, Wilmington, VT 05363

    • 4 Beds
    • 2.5 Baths
    • 2,989 Sq Ft
    • Built 1967

    Last Sold Summary

    • 1% Above List Price
    • $134/SF
    • 5 Days On Market

    Current Estimated Value $399,018

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    215 Old Town Rd, Wilmington, VT 05363
    • /31

      Est $332,878 Not Listed For Sale

      47 Sherwood Cir, Brattleboro, VT 05301

      • 3 Beds
      • 2 Baths
      • 1,400 Sq Ft
      • Built 1995
      47 Sherwood Cir, Brattleboro, VT 05301

      Last Sold Summary

      • 1% Below List Price
      • $239/SF
      • 38 Days On Market
      • Last Sold Price $335,000
      • May 16, 2024

      Last Listing Agent Christine Lewis Brattleboro Area Realty

  • /58

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,840 Sq Ft

    1192 Chapel Hill Rd, Whitingham, VT 05361

    Discover Vermont living at its finest in this architecturally unique round home, set on a 1-acre lot. Included in the sale is an additional 1-acre parcel directly across the street, offering potential for a garage, guest house, or Airbnb. Buyers should perform their own due diligence, as seller and broker make no representation on buildability. Step inside and walk into the welcoming lower level,

    Cliff Leinonen Four Seasons Sotheby's Int'l Realty

    1192 Chapel Hill Rd, Whitingham, VT 05361
  • /24

    $22,000 Sold Apr 01, 2026

    97 Glen St, Brattleboro, VT 05301

    • 2 Beds
    • 1 Bath
    • 684 Sq Ft
    • Built 1968

    Last Sold Summary

    • 26% Below List Price
    • $32/SF
    • 36 Days On Market

    Last Listing Agent Angela Sherman Brattleboro Area Realty

    97 Glen St, Brattleboro, VT 05301
    • /18

      Est $369,674 Not Listed For Sale

      7 Center Rd, Wilmington, VT 05363

      • 3 Beds
      • 1.5 Baths
      • 1,302 Sq Ft
      • Built 1965
      7 Center Rd, Wilmington, VT 05363

      Last Sold Summary

      • 5% Above List Price
      • $270/SF
      • 3 Days On Market
      • Last Sold Price $352,000
      • Oct 19, 2023

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /16

    $26,000

    • 1 Bed
    • 2 Baths
    • 771 Sq Ft

    163/65 Qtr.1,89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This sleep 8 unit consists of two adjoining units. Studio unit (unit 163) Queen murphy bed and queen sleeper sofa, kitchenette and full bathroom. Hotel unit (165) Two queen beds, Full bathroom and a deck. Units are located the valley side of the hotel. Benefits of Grand Summit ownership include the best ski in/out mountain

    Kelly Agrillo Southern Vermont Realty Group

    163/65 Qtr.1,89 Grand Summit Way, Dover, VT 05356
  • /30

    $197,000 Sold Jan 16, 2026

    77 Griswold Dr, Bellows Falls, VT 05101

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft
    • Built 1964

    Last Sold Summary

    • 30% Below List Price
    • $172/SF
    • 153 Days On Market

    Current Estimated Value $204,450

    Last Listing Agent Rob Weltz Barrett and Valley Associates Inc.

    77 Griswold Dr, Bellows Falls, VT 05101
    • /35

      Est $341,622 Not Listed For Sale

      31 Brook St, Whitingham, VT 05361

      • 4 Beds
      • 1.5 Baths
      • 1,783 Sq Ft
      • Built 1987
      31 Brook St, Whitingham, VT 05361

      Last Sold Summary

      • 2% Above List Price
      • $188/SF
      • 6 Days On Market
      • Last Sold Price $334,650
      • Apr 29, 2024

      Last Listing Agent Melissa Ellis Southern Vermont Realty Group

  • /29

    $335,000 Pending

    • 3 Beds
    • 2 Baths
    • 2,160 Sq Ft

    160 Sunny Acres Rd, Brattleboro, VT 05301

    Charming and well cared for ranch-style home offering comfortable one-level living. This inviting 3-bedroom, 2-bath property is move-in ready and the functional layout provides a bright living area, spacious bedrooms, and convenient everyday flow. Enjoy easy access to nearby schools, shopping, and local amenities while still having a cozy place to call home. A wonderful opportunity for those

    Claire Renaud Berkley & Veller Greenwood Country

    160 Sunny Acres Rd, Brattleboro, VT 05301
  • /19

    $475,000 Sold Oct 30, 2025

    0 Route 9 Unit 4905132, Marlboro, VT 05344

    • Land
    • 195 Acres
    • $2,436 per Acre

    Last Sold Summary

    • 12% Above List Price
    • 1,058 Days On Market

    Last Listing Agent Thom Milke Fountains Land Inc.

    0 Route 9 Unit 4905132, Marlboro, VT 05344
    • /34

      Est $354,237 Not Listed For Sale

      51 Apple Blossom Ln, Grafton, VT 05146

      • 3 Beds
      • 2.5 Baths
      • 1,600 Sq Ft
      • Built 1975
      51 Apple Blossom Ln, Grafton, VT 05146

      Last Sold Summary

      • 3% Below List Price
      • $228/SF
      • 27 Days On Market
      • Last Sold Price $365,000
      • May 01, 2024

      Last Listing Agent Heidi Bernier Berkley & Veller Greenwood Country

  • /59

    $1,300,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,900 Sq Ft

    51 Village Square, Stratton, VT 05360

    Experience this Extraordinary Location in the heart of the Stratton Resort Village from this RENOVATED and EXPANDED Village Square 4 bedroom unit where you can walk to everything and be on the lifts in just a few minutes. Nothing compares to trailside living in the VILLAGE where convenience abounds and you won't touch your car until it's time to hit the highway. Ski home for lunch and you'll have

    Kim Morgan-Wohler Wohler Realty Group

    51 Village Square, Stratton, VT 05360
  • /31

    $405,000 Sold Mar 05, 2026

    132 Pratt Bridge Rd, Jamaica, VT 05343

    • 3 Beds
    • 2 Baths
    • 1,814 Sq Ft
    • Built 1987

    Last Sold Summary

    • 13% Below List Price
    • $223/SF
    • 140 Days On Market

    Current Estimated Value $442,848

    Last Listing Agent Lisa Sullivan Four Seasons Sotheby's Int'l Realty

    132 Pratt Bridge Rd, Jamaica, VT 05343
    • /26

      Est $293,157 Not Listed For Sale

      240 S Main St, Brattleboro, VT 05301

      • 4 Beds
      • 2 Baths
      • 1,948 Sq Ft
      • Built 1865
      240 S Main St, Brattleboro, VT 05301

      Last Sold Summary

      • 9% Below List Price
      • $166/SF
      • 18 Days On Market
      • Last Sold Price $323,000
      • Nov 01, 2024

      Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country

  • /27

    $379,000

    • 4 Beds
    • 3 Baths
    • 1,720 Sq Ft

    292 Tallwood Cir, Londonderry, VT 05148

    Welcome to this charming chalet in the Sherwood Forest neighborhood of Londonderry! Come inside to a bright, open great room featuring living and dining areas, large windows, a cozy wood stove, and a breakfast bar that connects seamlessly to the kitchen. This inviting home is the perfect Vermont getaway for you or your guests. Just off the great room, the classic country kitchen offers an ideal

    The Malley Group KW Vermont

    292 Tallwood Cir, Londonderry, VT 05148
  • /34

    $1,250,000 Sold Nov 07, 2025

    15 Springhill Rd, Dover, VT 05356

    • 5 Beds
    • 4.5 Baths
    • 5,153 Sq Ft
    • Built 1991

    Last Sold Summary

    • 7% Below List Price
    • $243/SF
    • 119 Days On Market

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    15 Springhill Rd, Dover, VT 05356
    • /14

      Est $244,452 Not Listed For Sale

      202 Canal St, Brattleboro, VT 05301

      • Studio
      • 2 Baths
      • 2,708 Sq Ft
      • Built 1910
      202 Canal St, Brattleboro, VT 05301

      Last Sold Summary

      • 16% Above List Price
      • $78/SF
      • 6 Days On Market
      • Last Sold Price $210,000
      • Oct 03, 2024

      Last Listing Agent Kevin Holmes Blue Slate Realty

  • /54

    $2,050,000 Under Contract

    • 4 Beds
    • 4.5 Baths
    • 2,486 Sq Ft

    97 N Brookwood Rd, Stratton, VT 05360

    Welcome to your mountain chalet! 97 North Brookwood Road, one of the top most desirable locations on Stratton Mountain. Fully renovated and updated home, one of the eight original Austrian chalets on the mountain. Direct walk in and ski out to the Lower Wanderer trail. 4 bedroom in total with 3 en-suite bathrooms and 1 custom double bunk room with attached bathroom. Gorgeous great room with stone

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    97 N Brookwood Rd, Stratton, VT 05360
  • /34

    $265,000 Sold Oct 20, 2025

    199 Depot Rd, Williamsville, VT 05362

    • 2 Beds
    • 1 Bath
    • 1,137 Sq Ft
    • Built 1989

    Last Sold Summary

    • 4% Below List Price
    • $233/SF
    • 52 Days On Market

    Current Estimated Value $263,465

    Last Listing Agent Kate Barry EXP Realty

    199 Depot Rd, Williamsville, VT 05362
    • /25

      Est $293,004 Not Listed For Sale

      8 Route 35, Athens, VT 05143

      • 3 Beds
      • 1 Bath
      • 1,106 Sq Ft
      • Built 1980
      8 Route 35, Athens, VT 05143

      Last Sold Summary

      • 7% Above List Price
      • $249/SF
      • 12 Days On Market
      • Last Sold Price $275,000
      • Feb 22, 2024

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  • /8

    $480,000

    • Land
    • 5.08 Acres
    • $94,488 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
  • /40

    $525,000 Sold Jul 18, 2025

    35 Buckboard Dr, Dover, VT 05356

    • 3 Beds
    • 2 Baths
    • 1,372 Sq Ft
    • Built 1987

    Last Sold Summary

    • 1% Above List Price
    • $383/SF
    • 44 Days On Market

    Current Estimated Value $503,356

    Last Listing Agent Jillian Wimmelman Deerfield Valley Real Estate

    35 Buckboard Dr, Dover, VT 05356
    • /27

      Est $360,610 Not Listed For Sale

      239 Breezy Acres Dr, Vernon, VT 05354

      • 3 Beds
      • 1.5 Baths
      • 1,941 Sq Ft
      • Built 1992
      239 Breezy Acres Dr, Vernon, VT 05354

      Last Sold Summary

      • 3% Above List Price
      • $181/SF
      • 9 Days On Market
      • Last Sold Price $351,000
      • Jun 24, 2024

      Last Listing Agent A.J. Bellville Bellville Realty

  • /9

    $185,000

    • Land
    • 8 Acres
    • $23,125 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
  • /60

    $639,000 Sold Jan 09, 2026

    38 Greenspring Rd, Dover, VT 05356

    • 3 Beds
    • 3.5 Baths
    • 2,472 Sq Ft
    • Built 1990

    Last Sold Summary

    • 1% Below List Price
    • $258/SF
    • 66 Days On Market

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

    38 Greenspring Rd, Dover, VT 05356
    • /16

      Est $340,705 Not Listed For Sale

      3128 Windham Hill Rd, West Townshend, VT 05359

      • 2 Beds
      • 2 Baths
      • 1,499 Sq Ft
      • Built 1835
      3128 Windham Hill Rd, West Townshend, VT 05359

      Last Sold Summary

      • 100% Above List Price
      • $113/SF
      • 11 Days On Market
      • Last Sold Price $170,000
      • Aug 12, 2024

      Last Listing Agent Christopher Cummings Cummings & Co

  • /2

    $350,000

    • 2 Beds
    • 1 Bath
    • 3,312 Sq Ft

    573 S Main St, Brattleboro, VT 05301

    Just around the corner! From the middle and high school, Oak groveelementary! Pop around the corner for all the high school games,exercise at the track. Interstate is minutes away for easy access towork or play! One apartment is over 1,000 square feet so tons of roomfor owner occupancy! 2 nice front porches. Worth looking at for eitheryour own home or as an investment. Masks

    Christine Lewis Brattleboro Area Realty

    573 S Main St, Brattleboro, VT 05301
  • /27

    $21,000 Sold Apr 25, 2025

    366 Qtr.2, 89 Grand Summit Way, Dover, VT 05356

    • 1 Bed
    • 2 Baths
    • 785 Sq Ft
    • Built 1998

    Last Sold Summary

    • 34% Below List Price
    • $27/SF
    • 368 Days On Market

    Last Listing Agent Kelly Agrillo Southern Vermont Realty Group

    366 Qtr.2, 89 Grand Summit Way, Dover, VT 05356
    • /28

      Est $533,914 Not Listed For Sale

      5852 Windham Hill Rd, West Townshend, VT 05359

      • 4 Beds
      • 5 Baths
      • 3,854 Sq Ft
      • Built 1911
      5852 Windham Hill Rd, West Townshend, VT 05359

      Last Sold Summary

      • 1% Below List Price
      • $140/SF
      • 60 Days On Market
      • Last Sold Price $540,000
      • Mar 28, 2024

      Last Listing Agent Amy Carson Lowe's Real Estate, LLC

  • /41

    $2,999,000

    • 6 Beds
    • 3 Baths
    • 3,309 Sq Ft

    36 Woffenden Rd, Wilmington, VT 05363

    Discover the quintessential Vermont lifestyle at historic Wheeler Farm! Nestled amid its own 260+/- acres of scenic beauty, this 6-bedroom farmhouse embodies rural farmhouse charm. Open meadows, green hay fields and the sugarhouse's steam on spring days barely begin to tell the story of all this special property holds. Boasting a coveted southeast exposure, the home and land are cheerful and

    Melissa Ellis Southern Vermont Realty Group

    36 Woffenden Rd, Wilmington, VT 05363
  • /32

    $18,000 Sold Nov 14, 2025

    111, Qtr 3, 89 Grand Summit Way, Dover, VT 05356

    • 1 Bed
    • 1 Bath
    • 608 Sq Ft
    • Built 1998

    Last Sold Summary

    • 10% Below List Price
    • $30/SF
    • 37 Days On Market

    Last Listing Agent Patricia Fitzpatrick Skihome Realty

    111, Qtr 3, 89 Grand Summit Way, Dover, VT 05356
    • /25

      Est $646,057 Not Listed For Sale

      1245 Burbee Pond Rd, West Townshend, VT 05359

      • 4 Beds
      • 1.5 Baths
      • 1,800 Sq Ft
      • Built 1973
      1245 Burbee Pond Rd, West Townshend, VT 05359

      Last Sold Summary

      • 40% Above List Price
      • $257/SF
      • 270 Days On Market
      • Last Sold Price $462,000
      • Aug 29, 2023

      Last Listing Agent Jessica Citera Cummings & Co

  • /12

    $36,999

    • Land
    • 2 Acres
    • $18,500 per Acre

    14 Brickyard Rd, Dover, VT 05341

    Beautiful hillside parcel less than ten minutes from Mount Snow but outside the direct path of heavy tourist traffic. Brickyard Road is a winding packed-gravel road dotted sparsely with homes for full-time Dover residents, each with plenty of land and privacy. From the roadside the topography dips down about 5 feet, then quickly comes to a much more gradual slope which continues for approximately

    David White OwnerEntry.com

    14 Brickyard Rd, Dover, VT 05341
  • /56

    $325,000 Sold Jun 25, 2025

    24 Blackberry Lane Private, Dover, VT 05356

    • 3 Beds
    • 1.5 Baths
    • 1,400 Sq Ft
    • Built 2024

    Last Sold Summary

    • 35% Below List Price
    • $232/SF
    • 212 Days On Market

    Last Listing Agent Erica Reynolds Southern Vermont Realty Group

    24 Blackberry Lane Private, Dover, VT 05356
    • /26

      Est $414,559 Not Listed For Sale

      11 Corn Hill Rd, West Townshend, VT 05359

      • 6 Beds
      • 2 Baths
      • 3,005 Sq Ft
      • Built 1834
      11 Corn Hill Rd, West Townshend, VT 05359

      Last Sold Summary

      • 26% Above List Price
      • $109/SF
      • 71 Days On Market
      • Last Sold Price $328,000
      • Oct 30, 2023

      Last Listing Agent Jason Lovett Berkley & Veller Greenwood Country

  • /44

    $384,000

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    25 Upper Handle Rd Unit A, Dover, VT 05356

    Welcome to this inviting 3-bedroom plus loft, 2-bath Apple Hill condominium—perfectly located just minutes from Mount Snow. This spacious and well-maintained home offers a comfortable layout for a relaxing Vermont getaway. The updated kitchen and dining area feature a charming window seat, while the open-concept living room boasts another cozy window seat and a wood-burning fireplace for those

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    25 Upper Handle Rd Unit A, Dover, VT 05356

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