30,689

Windham County, VT Homes

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  • /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
    • /37

      Est $579,920 Not Listed For Sale

      8117 Windham Hill Rd, West Townshend, VT 05359

      • 2 Beds
      • 1 Bath
      • 1,340 Sq Ft
      • Built 1950
      8117 Windham Hill Rd, West Townshend, VT 05359

      Last Sold Summary

      • 17% Above List Price
      • $369/SF
      • 18 Days On Market

      Last Sold Price $495,000

      Last Listing Agent Dan McKenna Cummings & Co

  • /24

    $399,000

    • 4 Beds
    • 2 Baths
    • 1,830 Sq Ft

    4850 Vermont Route 100, Wardsboro, VT 05355

    Dual charming updated cottages located conveniently between Mount Snow and Stratton with easy access off a paved public road for peace of mind and tremendous rentability. The current owners have lovingly updated these 2 cape style homes. One partially burned down and has been completely rebuilt and just completed. That larger home features an open concept kitchen and dining area, large great room

    Adam Palmiter Berkley & Veller Greenwood/Dover

    4850 Vermont Route 100, Wardsboro, VT 05355
  • /54

    $1,050,000 Sold Feb 06, 2026

    339 Coldbrook Rd, Wilmington, VT 05363

    • 4 Beds
    • 3 Baths
    • 3,506 Sq Ft
    • Built 1988

    Last Sold Summary

    • 12% Below List Price
    • $299/SF
    • 170 Days On Market

    Current Estimated Value $1,190,826

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

    339 Coldbrook Rd, Wilmington, VT 05363
    • /40

      Est $1,081,072 Not Listed For Sale

      220 Lake Raponda Rd, Wilmington, VT 05363

      • 4 Beds
      • 2 Baths
      • 2,200 Sq Ft
      • Built 1930
      220 Lake Raponda Rd, Wilmington, VT 05363

      Last Sold Summary

      • 2% Below List Price
      • $500/SF
      • 6 Days On Market

      Last Sold Price $1,100,000

      Last Listing Agent Donald Koelsch Deerfield Valley Real Estate

  • /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
  • /53

    $1,525,000 Sold Sep 30, 2025

    3333 Under the Mountain Rd, Londonderry, VT 05148

    • 3 Beds
    • 3.5 Baths
    • 5,105 Sq Ft
    • Built 2003

    Last Sold Summary

    • $299/SF
    • 7 Days On Market

    Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    3333 Under the Mountain Rd, Londonderry, VT 05148
    • /40

      Est $2,345,842 Not Listed For Sale

      118 W Lake Rd, Wilmington, VT 05363

      • 4 Beds
      • 3.5 Baths
      • 5,392 Sq Ft
      • Built 2018
      118 W Lake Rd, Wilmington, VT 05363

      Last Sold Summary

      • 11% Below List Price
      • $491/SF
      • 21 Days On Market

      Last Sold Price $2,650,000

      Last Listing Agent Rich Caplan Deerfield Valley Real Estate

  • /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
  • /45

    $429,500 Sold Feb 20, 2026

    210 Burrington Hill Rd, Whitingham, VT 05361

    • 3 Beds
    • 2 Baths
    • 1,564 Sq Ft
    • Built 2007

    Last Sold Summary

    • 2% Below List Price
    • $275/SF
    • 35 Days On Market

    Current Estimated Value $435,973

    Last Listing Agent Jacki Murano Southern Vermont Realty Group

    210 Burrington Hill Rd, Whitingham, VT 05361
    • /22

      Est $396,841 Not Listed For Sale

      498 Stowe Hill Rd, Wilmington, VT 05363

      • 3 Beds
      • 1 Bath
      • 1,000 Sq Ft
      • Built 1965
      498 Stowe Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 12% Above List Price
      • $354/SF
      • 115 Days On Market

      Last Sold Price $353,500

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /41

    $3,050,000

    • 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
  • /26

    $31,000 Sold Mar 12, 2025

    89 Grand Summit Way Unit 345 Q3, Dover, VT 05356

    • 1 Bed
    • 2 Baths
    • 1,005 Sq Ft
    • Built 1998

    Last Sold Summary

    • 14% Below List Price
    • $31/SF
    • 137 Days On Market

    Last Listing Agent Steve Goldfarb Deerfield Valley Real Estate

    89 Grand Summit Way Unit 345 Q3, Dover, VT 05356
    • /24

      Est $626,209 Not Listed For Sale

      82 Lisle Hill Rd, Wilmington, VT 05363

      • 7 Beds
      • 4.5 Baths
      • 3,600 Sq Ft
      • Built 1989
      82 Lisle Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 24% Above List Price
      • $140/SF
      • 177 Days On Market

      Last Sold Price $505,000

      Last Listing Agent Derek Greene Derek Greene

  • /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
  • /2

    $428,000 Sold Mar 13, 2025

    5735 Vt Route 11, Londonderry, VT 05148

    • 4 Beds
    • 4 Baths
    • 2,320 Sq Ft
    • Built 1890

    Last Sold Summary

    • 11% Below List Price
    • $184/SF
    • 158 Days On Market

    Current Estimated Value $470,883

    Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

    5735 Vt Route 11, Londonderry, VT 05148
    • /29

      Est $328,779 Not Listed For Sale

      19 Stowe Hill Rd, Wilmington, VT 05363

      • 3 Beds
      • 2 Baths
      • 1,632 Sq Ft
      • Built 1968
      19 Stowe Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 11% Below List Price
      • $225/SF
      • 76 Days On Market

      Last Sold Price $367,500

      Last Listing Agent Erica Reynolds Southern Vermont Realty Group

  • /44

    $399,000

    • 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
  • /18

    $335,000 Sold Jul 30, 2025

    138 Cedar St, Brattleboro, VT 05301

    • 3 Beds
    • 1 Bath
    • 1,174 Sq Ft
    • Built 1956

    Last Sold Summary

    • 3% Above List Price
    • $285/SF
    • 36 Days On Market

    Current Estimated Value $334,220

    Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

    138 Cedar St, Brattleboro, VT 05301
    • /53

      Est $397,726 Not Listed For Sale

      29 Ray Hill Rd, Wilmington, VT 05363

      • 4 Beds
      • 1.5 Baths
      • 2,196 Sq Ft
      • Built 1957
      29 Ray Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 8% Above List Price
      • $168/SF
      • 34 Days On Market

      Last Sold Price $368,000

      Last Listing Agent Donald Koelsch Deerfield Valley Real Estate

  • /28

    $269,000 Coming Soon

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

    15 West St, Brattleboro, VT 05301

    Enjoy a spacious kitchen that flows seamlessly into a large living area with open views of Mount Wantastiquet. This single-level ranch offers four generously sized bedrooms and a full bath, making it ideal for those seeking one-floor living and efficient heating. A cozy woodstove in the living area helps offset heating costs while adding warmth and charm. Hardwood flooring, a beautifully tiled

    Liz LaVorgna Brattleboro Area Realty

    15 West St, Brattleboro, VT 05301
  • /40

    $1,595,000 Sold Mar 24, 2025

    37 Deer Hill Rd, Newfane, VT 05345

    • 5 Beds
    • 3.5 Baths
    • 3,534 Sq Ft
    • Built 1840

    Last Sold Summary

    • 11% Below List Price
    • $451/SF
    • 156 Days On Market

    Last Listing Agent Thomas Dahlin Berkley & Veller Greenwood Country

    37 Deer Hill Rd, Newfane, VT 05345
    • /33

      Est $382,930 Not Listed For Sale

      8 Castle Hill Rd, Wilmington, VT 05363

      • 4 Beds
      • 2 Baths
      • 1,643 Sq Ft
      • Built 1957
      8 Castle Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 2% Above List Price
      • $228/SF
      • 89 Days On Market

      Last Sold Price $375,000

      Last Listing Agent Prema Fitzpatrick Real Broker LLC

  • /8

    $48,000

    • Land
    • 6.1 Acres
    • $7,869 per Acre

    0 Cooke Rd, Brattleboro, VT 05301

    Amidst rolling VT farmland, sits these 6 acres in West Brattleboro. While there is road frontage on Rte 9, the driveway is off the class 4 section of Cooke Rd. There's about 250 feet of Cooke Rd that you would need to maintain before the town road. The ROW into the land parallels the power lines, which you cannot see when you're on the land. There a nice cleared shelf when you walk in and then

    Victoria Woods Brattleboro Area Realty

    0 Cooke Rd, Brattleboro, VT 05301
  • /43

    $490,000 Sold Jun 16, 2025

    132 Pingree Park Ln, Londonderry, VT 05148

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft
    • Built 1982

    Last Sold Summary

    • 12% Below List Price
    • $407/SF
    • 239 Days On Market

    Current Estimated Value $514,788

    Last Listing Agent Alison Cummings Cummings & Co

    132 Pingree Park Ln, Londonderry, VT 05148
    • /30

      Est $419,709 Not Listed For Sale

      18 Castle Hill Rd, Wilmington, VT 05363

      • 5 Beds
      • 2 Baths
      • 2,295 Sq Ft
      • Built 1840
      18 Castle Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 38% Above List Price
      • $133/SF
      • 163 Days On Market

      Last Sold Price $305,000

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /12

    $119,000

    • Land
    • 5 Acres
    • $23,800 per Acre

    0 Banning Rd, Putney, VT 05346

    Location is key, and locations like this don't come along often. Almost at the top of Putney Mountain is this 5+/- acres of mature hard and soft woods, including red oak, birch, beech, pine and hemlock, just waiting to host your full or part time dwelling. The existing driveway, which is shared with the seller, offers access to the length of the parcel. There's a State Wastewater Permit with a

    Bill Hickok Berkley & Veller Greenwood Country

    0 Banning Rd, Putney, VT 05346
  • /21

    $136,000 Sold May 02, 2025

    724 Saxtons River Rd, Saxtons River, VT 05154

    • Land
    • 3.57 Acres
    • $38,095 per Acre

    Last Sold Summary

    • 9% Below List Price
    • 207 Days On Market

    Last Listing Agent Evan Russell Real Broker LLC

    724 Saxtons River Rd, Saxtons River, VT 05154
    • /34

      Est $711,974 Not Listed For Sale

      72 Castle Hill Rd, Wilmington, VT 05363

      • 4 Beds
      • 3 Baths
      • 2,148 Sq Ft
      • Built 1967
      72 Castle Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 5% Above List Price
      • $314/SF
      • 52 Days On Market

      Last Sold Price $675,000

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /26

    $395,000

    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft

    135 Country Hill, Brattleboro, VT 05301

    Built in 2004 in this much-loved neighborhood, on a desirable one-way cul-de-sac, beautifully maintained, sits this 3-bedroom, 3-bath home. The first floor has a beautiful, large, eat-in kitchen, dining room, 1/2 bath, and access to a very spacious and inviting 16x16 deck ideal for family gatherings or entertaining, and a real sense of privacy. On the second floor, there is a primary bedroom with

    Neil Goldberg Brattleboro Area Realty

    135 Country Hill, Brattleboro, VT 05301
  • /2

    $155,000 Sold Aug 20, 2025

    461 Deer Run, Putney, VT 05346

    • Land
    • 18.5 Acres
    • $8,378 per Acre

    Last Sold Summary

    • 4% Above List Price
    • 11 Days On Market

    Current Estimated Value $153,273

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    461 Deer Run, Putney, VT 05346
    • /40

      Est $452,884 Not Listed For Sale

      50 Ray Hill Rd, Wilmington, VT 05363

      • 3 Beds
      • 2 Baths
      • 2,200 Sq Ft
      • Built 1950
      50 Ray Hill Rd, Wilmington, VT 05363

      Last Sold Summary

      • 19% Above List Price
      • $173/SF
      • 48 Days On Market

      Last Sold Price $381,250

      Last Listing Agent Chad Lackey Deerfield Valley Real Estate

  • /15

    $455,000

    • 2 Beds
    • 2 Baths
    • 1,353 Sq Ft

    49 High Point Dr Unit A-14, Stratton, VT 05360

    49 High Point Drive, Crown Point A14, Stratton, VTIncredible opportunity to make Stratton Mountain Resort a place to call home. Nestled in the Green Mountains of Vermont, Crown Point offers easy condominium living close to the Stratton Mountain Resort Village. Shuttle service to the base area for skiing and riding. An outdoor pool and BBQ area is inviting for summer use. This one-level 2

    Andrew King Stratton Real Estate

    49 High Point Dr Unit A-14, Stratton, VT 05360
  • /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
    • /18

      Est $319,758 Not Listed For Sale

      36 Sparrow Ln, Wilmington, VT 05363

      • 5 Beds
      • 2.5 Baths
      • 2,030 Sq Ft
      • Built 1945
      36 Sparrow Ln, Wilmington, VT 05363

      Last Sold Summary

      • 276% Above List Price
      • $42/SF
      • 112 Days On Market

      Last Sold Price $85,000

      Last Listing Agent Flex Realty Group Flex Realty

  • /17

    $150,000

    • Land
    • 2.8 Acres
    • $53,571 per Acre

    37 Fred Houghton Rd, Putney, VT 05346

    Just in time! So special! This unusual offering was a beloved family complex for many years. The land is a delight of mixed hardwoods and evergreens, easy to walk and gently rolling for intrigue. Walk to "downtown" Putney for the small town energy, pop in the auto for a short drive to everything else...interstate access, NH, skiing...hospitals and services.....or tuck in at home for a

    Christine Lewis Brattleboro Area Realty

    37 Fred Houghton Rd, Putney, VT 05346
  • /40

    $285,000 Sold May 09, 2025

    2469 Augur Hole Rd, Guilford, VT 05301

    • 2 Beds
    • 3.5 Baths
    • 1,228 Sq Ft
    • Built 1960

    Last Sold Summary

    • 3% Below List Price
    • $232/SF
    • 50 Days On Market

    Last Listing Agent Patrice Schneider Southern Vermont Realty Group

    2469 Augur Hole Rd, Guilford, VT 05301
    • /33

      Est $312,793 Not Listed For Sale

      752 Route 9 E, Wilmington, VT 05363

      • 3 Beds
      • 1.5 Baths
      • 1,088 Sq Ft
      • Built 1953
      752 Route 9 E, Wilmington, VT 05363

      Last Sold Summary

      • 7% Above List Price
      • $268/SF
      • 72 Days On Market

      Last Sold Price $292,000

      Last Listing Agent Kim Meeker Southern Vermont Realty Group

  • /35

    $899,900

    • 4 Beds
    • 3.5 Baths
    • 2,272 Sq Ft

    12 Encore Place, Dover, VT 05356

    Mountain Modern Living with unmatched ski views of Mount Snow. Discover the perfect blend of luxury and nature in this 3 year young contemporary home ideally situated to capture breathtaking unobstructed views of Carinthia. This thoughtfully designed 4 bedroom home offers an open concept floor plan while still offering privacy and cozy spaces that highlight the beauty of the alpine landscape.

    Heidi Zizza Four Seasons Sotheby's Int'l Realty

    12 Encore Place, Dover, VT 05356
  • /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 $275,273

    Last Listing Agent John Hatton Berkley & Veller Greenwood Country

    130 Beechnut Ln, Putney, VT 05346

Showing Results 241 - 280, Page 7 of 18

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