30,689

Windham County, VT Homes

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  • /33

    $386,250 Sold Jun 12, 2025

    33 Frost Place, Brattleboro, VT 05301

    • 3 Beds
    • 2.5 Baths
    • 1,617 Sq Ft
    • Built 1880

    Last Sold Summary

    • 3% Below List Price
    • $239/SF
    • 49 Days On Market

    Current Estimated Value $332,000

    Last Listing Agent Keith Nowak Four Seasons Sotheby's Int'l Realty

    33 Frost Place, Brattleboro, VT 05301
    • /40

      Est $557,287 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

      • 30% Below List Price
      • $341/SF
      • 5 Days On Market

      Last Sold Price $800,000

      Last Listing Agent Michelle O'Neil Deerfield Valley Real Estate

  • /40

    $214,900

    • 5 Beds
    • 3.5 Baths
    • 3,600 Sq Ft

    2139 Vt Route 30, Townshend, VT 05353

    Great days ahead for the buyer of this stately, manor styled home on close to three (3) acres. You have to see the interior to believe it. Dated? Yes, but solid bones. Crazy nice wood floors, classic built-ins & style. So many 'nooks & crannies. Cavernous, dry & clean basement. Exterior: 'challenged', but I have all the bids to bring it to 'good' condition & the techies are ready to complete

    Robert Balewicz Evergreen Realty of Vermont

    2139 Vt Route 30, Townshend, VT 05353
  • /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 $252,332

    Last Listing Agent Kerry Mulverhill

    2069 Fort Bridgman Rd, Vernon, VT 05354
    • /31

      Est $355,963 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

      • 6% Above List Price
      • $239/SF
      • 38 Days On Market

      Last Sold Price $335,000

      Last Listing Agent Christine Lewis Brattleboro Area Realty

  • /27

    $425,000

    • 5 Beds
    • 3 Baths
    • 1,440 Sq Ft

    135 Overlook Dr, Londonderry, VT 05148

    Investment opportunity! This beautiful ski country compound offers 3 streams of rental income, or a home where you can enjoy sweeping views of the West River Valley just minutes away from Magic Mountain skiing and a surprising array of amenities in Londonderry’s town center. A barn apartment over a garage with a 3/4 bath, and an upstairs and downstairs unit with a full bath each, are all equipped

    Zachary Zupan EXP Realty

    135 Overlook Dr, Londonderry, VT 05148
  • /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 $403,724

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    215 Old Town Rd, Wilmington, VT 05363
    • /18

      Est $373,107 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

      • 6% Above List Price
      • $270/SF
      • 3 Days On Market

      Last Sold Price $352,000

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /9

    $198,000

    • Land
    • 0.73 Acre
    • $271,233 per Acre

    5 Pinnacle View Rd, Dover, VT 05356

    With views of Mount Snow, this exceptional 0.73-acre parcel is the perfect setting for your dream mountain retreat. Located in the resort district, short-term rentals are permitted, making this a prime investment opportunity or an ideal family legacy home for generations to enjoy. Just off Route 100, a one-minute drive to the lifts at Mount Snow,an Epic Pass mountain, offering world-class skiing

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    5 Pinnacle View Rd, 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 $242,486

    Last Listing Agent Rob Weltz Barrett and Valley Associates Inc.

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

      Est $357,882 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

      • 7% Above List Price
      • $188/SF
      • 6 Days On Market

      Last Sold Price $334,650

      Last Listing Agent Melissa Ellis Southern Vermont Realty Group

  • /52

    $1,150,000

    • 8 Beds
    • 4 Baths
    • 4,828 Sq Ft

    5 Tannery Rd, West Dover, VT 05356

    Discover your getaway at Mount Snow in this beautifully renovated 8-bedroom estate, ideal for unforgettable family gatherings, cherished reunions, or inspiring work retreats. Set on nearly 4 serene acres at the foot of Mount Snow, you'll be surrounded by breathtaking mountain views and enjoy effortless access to the slopes just a short drive away. This magnificent home features a dedicated

    Michelle O'Neil Deerfield Valley Real Estate

    5 Tannery Rd, West Dover, VT 05356
  • /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 $367,114 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

      • 1% Above List Price
      • $228/SF
      • 27 Days On Market

      Last Sold Price $365,000

      Last Listing Agent Heidi Bernier Berkley & Veller Greenwood Country

  • /37

    $50,000

    • Land
    • 0.93 Acre
    • $53,763 per Acre

    564 Upper Dam Rd, Wilmington, VT 05363

    Double lot on top of the Hill! Recent soil tests say this looks good for a 3-bedroom home! If you've been thinking of building your dream home, this is a great spot. Walk to the Clubhouse, seasonal views, about 2,400' in elevation, facing SE. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season tennis, basketball, pickleball, ice skating, pond fishing,

    Sigrid Pickering Chimney Hill Realty

    564 Upper Dam Rd, Wilmington, VT 05363
  • /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
    • /26

      Est $314,607 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

      • 3% Below List Price
      • $166/SF
      • 18 Days On Market

      Last Sold Price $323,000

      Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country

  • /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
  • /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 $293,600

    Last Listing Agent Kate Barry EXP Realty

    199 Depot Rd, Williamsville, VT 05362
    • /14

      Est $251,470 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

      • 20% Above List Price
      • $78/SF
      • 6 Days On Market

      Last Sold Price $210,000

      Last Listing Agent Kevin Holmes Blue Slate Realty

  • /24

    $29,900 Pending

    • 2 Beds
    • 1 Bath
    • 684 Sq Ft

    97 Glen St, Brattleboro, VT 05301

    Finally!! Affordable!! This just right sized home is tucked into the 55 and older park for peace and quiet. Along the brook, the damaged homes have been removed and replaced with open green space with a gentle park like feel. There is an awning over the stairs, an added pitched roof, spacious front end kitchen/dining with several windows and some built-ins. Located in one of the 3 parks, making

    Angela Sherman Brattleboro Area Realty

    97 Glen St, Brattleboro, VT 05301
  • /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 $511,999

    Last Listing Agent Jillian Wimmelman Deerfield Valley Real Estate

    35 Buckboard Dr, Dover, VT 05356
    • /25

      Est $292,965 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

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  • /31

    $435,000 Under Contract

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

    132 Pratt Bridge Rd, Jamaica, VT 05343

    Welcome to this charming Vermont getaway, custom - built and lovingly maintained by the original owners. Ideally located just minutes from Stratton Mountain and within easy reach of Bromley and Magic for a full season of winter adventure. In the warmer months, enjoy nearby lakes perfect for swimming, paddling, or simply relaxing by the water.Inside, the home offers 3 bedrooms and 2 full

    Lisa Sullivan Four Seasons Sotheby's Int'l Realty

    132 Pratt Bridge Rd, 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
    • /27

      Est $321,792 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

      • 8% Below List Price
      • $181/SF
      • 9 Days On Market

      Last Sold Price $351,000

      Last Listing Agent A.J. Bellville Bellville 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
  • /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
    • /16

      Est $294,034 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

      • 73% Above List Price
      • $113/SF
      • 11 Days On Market

      Last Sold Price $170,000

      Last Listing Agent Christopher Cummings Cummings & Co

  • /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
  • /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
    • /28

      Est $622,484 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

      • 15% Above List Price
      • $140/SF
      • 60 Days On Market

      Last Sold Price $540,000

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

  • /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
  • /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
    • /25

      Est $725,123 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

      • 57% Above List Price
      • $257/SF
      • 270 Days On Market

      Last Sold Price $462,000

      Last Listing Agent Jessica Citera Cummings & Co

  • /29

    $469,000

    • 3 Beds
    • 3 Baths
    • 2,016 Sq Ft

    33D White Oaks Loop Unit 38, Dover, VT 05356

    Owners will consider offers. Nicely updated and uniquely private Timber Creek end-unit townhome with easy access and winter ski trail views. Ideally located directly across from the upper entrance to Mount Snow, Timber Creek offers shuttle service from your front door to the base area, along with convenient on-site management, exterior maintenance, snow removal, landscaping, and more. The

    Adam Palmiter Berkley & Veller Greenwood/Dover

    33D White Oaks Loop Unit 38, Dover, VT 05356
  • /15

    $370,000 Sold Aug 04, 2025

    761 Stratton Mountain Access Rd Unit 231, Stratton, VT 05360

    • 1 Bed
    • 1 Bath
    • 580 Sq Ft
    • Built 1999

    Last Sold Summary

    • 13% Below List Price
    • $638/SF
    • 120 Days On Market

    Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

    761 Stratton Mountain Access Rd Unit 231, Stratton, VT 05360
    • /26

      Est $385,531 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

      • 18% Above List Price
      • $109/SF
      • 71 Days On Market

      Last Sold Price $328,000

      Last Listing Agent Jason Lovett Berkley & Veller Greenwood Country

  • /54

    $2,050,000

    • 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
  • /27

    $285,000 Sold Dec 10, 2025

    91 Carriage Hill Rd, Brattleboro, VT 05301

    • 3 Beds
    • 1 Bath
    • 912 Sq Ft
    • Built 1975

    Last Sold Summary

    • 5% Below List Price
    • $312/SF
    • 41 Days On Market

    Current Estimated Value $284,112

    Last Listing Agent Rebecca Seymour Brattleboro Area Realty

    91 Carriage Hill Rd, Brattleboro, VT 05301

Showing Results 201 - 240, Page 6 of 18

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