Windham County, VT Homes

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  $142,000

  • Land
  • 2.19 Acres
  • $64,840 per Acre

  192 Pingree Park Ln, Londonderry, VT 05148

  2.19 acres with 199’ waterfront bordering the west bank of pristine Utley Brook with headwaters flowing from the national forestWaterfront parcel, septic fully engineered and permitted for a 4 bedroom home. Set at the end of a quiet, dead-end lane, this is a rare gem in Londonderry. Beautiful riverfront, convenient to everything in one of Vermont’s most sought-after mountain areas. Located

  

  Alison Cummings

  Cummings & Co

  (802) 416-4003

  192 Pingree Park Ln, Londonderry, VT 05148
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  /12

  $2,000 per month

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft
  • Condo for Rent

  167 Howard Rd Unit 2, Wardsboro, VT 05355

  Property Id: 2203648One bedroom one bathroom apartment completely remodeled, open concept located on a dead end road in Wardsboro Vermont. Furnished/Unfurnished/ Partially furnished upon tenants request. Close to Mount Snow, Stratton & Bromley Mountains. Use of one bay in garage. All kitchen appliances are new stainless steel in addition landlord provides blender, coffeemaker,

  167 Howard Rd Unit 2, Wardsboro, VT 05355
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  /31

  $499,000 Sold Nov 07, 2025

  321 Leonard Rd, Dummerston, VT 05301

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 2016

  Last Sold Summary

  • $318/SF
  • 67 Days On Market

  Last Listing Agent John Hatton Berkley & Veller Greenwood Country

  321 Leonard Rd, Dummerston, VT 05301
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  /28

  Est $843,490 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,876 Sq Ft

  11 Country Club Rd, Wilmington, VT 05363

  11 Country Club Rd, Wilmington, VT 05363
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  $395,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 2,400 Sq Ft

  3298 Houghtonville Rd, Grafton, VT 05146

  Classic 1800s Farmhouse in Charming Grafton, VermontLocated in Houghtonville, a beautiful part of historic Grafton, this mid-19th century farmhouse offers a rare opportunity to restore and reimagine a true Vermont original. With strong bones and timeless character, the home features wide plank floors, vintage woodwork, and a traditional layout that reflects its heritage. Typical of this

  

  Alison Cummings

  Cummings & Co

  (802) 317-7411

  3298 Houghtonville Rd, Grafton, VT 05146
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  /11

  $1,700 per month

  • 1 Bed
  • 1 Bath
  • 300 Sq Ft
  • Apartment for Rent

  4 Elliot St Unit 2, Brattleboro, VT 05301

  Corner apartment in downtown Brattleboro in the National is located on the corner of Elliot and Main Street. This one-bedroom apartment is in a secure building, laundry facilities on site, with parking down the street in the parking garage. Pets are welcome with an extra pet fee.

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  4 Elliot St Unit 2, Brattleboro, VT 05301
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  /20

  $390,000 Sold Aug 27, 2025

  2456 Deer Park Rd, West Halifax, VT 05358

  • 2 Beds
  • 3 Baths
  • 2,392 Sq Ft
  • Built 1990

  Last Sold Summary

  • 9% Above List Price
  • $163/SF
  • 14 Days On Market

  Current Estimated Value $387,000

  Last Listing Agent Teddy Kramer Berkley & Veller Greenwood Country

  2456 Deer Park Rd, West Halifax, VT 05358
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  /11

  Est $294,471 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,992 Sq Ft

  48 Loop Rd, Newfane, VT 05345

  48 Loop Rd, Newfane, VT 05345
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  $127,000

  • Land
  • 2.07 Acres
  • $61,353 per Acre

  191 Pingree Park Ln, Londonderry, VT 05148

  2.07 acres with 140’ waterfront bordering the west bank of pristine Utley Brook with headwaters flowing from the national forest. Waterfront parcel, septic fully engineered and permitted for a 4 bedroom home. Set at the end of a quiet, dead-end lane, this is a rare gem in Londonderry. Beautiful riverfront, convenient to everything in one of Vermont’s most sought-after mountain areas. Located just

  

  Alison Cummings

  Cummings & Co

  (802) 613-9168

  191 Pingree Park Ln, Londonderry, VT 05148
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  /12

  $1,400 per month

  • 1 Bed
  • 1 Bath
  • 437 Sq Ft
  • Condo for Rent

  131 Green St, Brattleboro, VT 05301

  Welcome to your future home in the charming district of Brattleboro, VT! This delightful property offers a perfect blend of comfort and convenience, situated just minutes away from great dining options and the Brattleboro Memorial Hospital.This 1st floor, one bedroom, 3 room residence features ample living space with central heating.Please note that rent does include heat, hot

  131 Green St, Brattleboro, VT 05301
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  /2

  $699,000 Sold Feb 21, 2025

  71B Kingswood Rd, Dover, VT 05356

  • 4 Beds
  • 3.5 Baths
  • 2,412 Sq Ft
  • Built 1996

  Last Sold Summary

  • $290/SF
  • 0 Days On Market

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

  71B Kingswood Rd, Dover, VT 05356
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  /33

  Est $218,921 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 856 Sq Ft

  849 Mcmillan Rd, Halifax, VT 05342

  849 Mcmillan Rd, Halifax, VT 05342
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  /22

  $850,000

  • Land
  • 67 Acres
  • $12,687 per Acre

  00 S Pine Banks Rd, Putney, VT 05346

  Unleash the potential of this exceptional 60+ acre Vermont property, a rare offering brimming with diverse landscapes and endless possibilities. A well-maintained gravel driveway leads you into the heart of the land, complete with readily available power. Discover multiple potential building sites, each offering breathtaking views or secluded privacy, tailored to your preference. A charming

  

  Ross Doody

  Century 21 Highview Realty

  (802) 499-2391

  00 S Pine Banks Rd, Putney, VT 05346
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  /31

  $1,600 per month

  • 1 Bed
  • 1 Bath
  • 875 Sq Ft
  • Apartment for Rent

  118 Vt Route 30 Unit 1, Newfane, VT 05345

  Sweet first-floor apartment in fantastic location! Clean and ready for new occupant. Apartment features open concept living space, recessed lighting and over-sized windows. Bonuses include laundry room, covered parking and bonus of electric car charging port. Fresh interior paint and carpet cleaning after change of tenant. An easy 15-minute commute to Brattleboro and I-91. Low maintenance as rent

  Jessica Landers Barrett and Valley Associates Inc.

  118 Vt Route 30 Unit 1, Newfane, VT 05345
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  /12

  $125,000 Sold Dec 11, 2025

  0 Dalewood Rd Unit 4955807, Jamaica, VT 05343

  • Land
  • 1.51 Acres
  • $82,781 per Acre

  Last Sold Summary

  • 880 Days On Market

  Last Listing Agent Mike England Michael England Real Estate

  0 Dalewood Rd Unit 4955807, Jamaica, VT 05343
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  /32

  Est $503,832 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft

  476 Edie Ln, Jamaica, VT 05343

  476 Edie Ln, Jamaica, VT 05343
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  /34

  $359,000

  • 3 Beds
  • 1.5 Baths
  • 1,152 Sq Ft

  410 Tallwood Cir, Londonderry, VT 05148

  This cute Sherwood Forest house is ready for the next owners! Nicely renovated over the past several years, this 3 bedroom, 1 and a half bath chalet is located in the heart of Vermont ski country. In between Londonderry and Bromley, minutes from Manchester or Stratton and Magic ,this central location allows for access to all that makes Vermont special! Enjoy the open living area after a day of

  

  Alison Cummings

  Cummings & Co

  (802) 392-0721

  410 Tallwood Cir, Londonderry, VT 05148
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  /5

  $1,400 per month

  • 1 Bed
  • 1 Bath
  • 410 Sq Ft
  • Condo for Rent

  498 Marlboro Rd Unit S34, Brattleboro, VT 05301

  Property Id: 1510809One bedroom apartment for rent in a professionally managed apartment building in West Brattleboro, Vermont. Clean, bright, with on-site laundry and off-street parking. Rents include heat and hot water. All units are non smoking. Small pets would require approval and an additional security deposit.

  498 Marlboro Rd Unit S34, Brattleboro, VT 05301
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  /55

  $410,000 Sold Dec 23, 2025

  52 Edward's Village Loop, Dover, VT 05356

  • 4 Beds
  • 2.5 Baths
  • 1,572 Sq Ft
  • Built 1979

  Last Sold Summary

  • 3% Above List Price
  • $261/SF
  • 3 Days On Market

  Last Listing Agent Donna Brown Skihome Realty

  52 Edward's Village Loop, Dover, VT 05356
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  /24

  Est $229,667 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,120 Sq Ft

  1751 Rockingham Rd, Rockingham, VT 05143

  1751 Rockingham Rd, Rockingham, VT 05143
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  /49

  $75,000

  • 3 Beds
  • 3 Baths
  • 2,326 Sq Ft

  92 Founders Hill Rd Unit 5A, Stratton, VT 05340

  Mountain Ridge 5A at Stratton offers a rare opportunity to own a quartershare at the very heart of the mountain. This beautifully designed 3-bedroom, 3-bath residence is one of just seven homes in this intimate community, all thoughtfully positioned steps from the base lodge, gondola, and Stratton Village dining, shopping, and nightlife. Inside, a vaulted great room filled with natural light

  

  Trent Stephens

  Wohler Realty Group

  (802) 521-2464

  92 Founders Hill Rd Unit 5A, Stratton, VT 05340
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  /12

  $1,650 per month

  • 1 Bed
  • 1 Bath
  • 524 Sq Ft
  • House for Rent

  722 Vermont 30, Townshend, VT 05353

  Single Family home located in Townshend, newly renovated with fresh paint and flooring. All rooms have natural light and plenty of windows to enjoy the nature right outside the window. This home has a large private yard, just minutes from shopping.

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  722 Vermont 30, Townshend, VT 05353
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  /2

  $80,000 Sold Aug 01, 2025

  100 Legion Rd, Newfane, VT 05345

  • 2 Beds
  • 1 Bath
  • 1,413 Sq Ft
  • Built 1990

  Last Sold Summary

  • 36% Below List Price
  • $57/SF
  • 245 Days On Market

  Current Estimated Value $79,604

  Last Listing Agent Christine Lewis Brattleboro Area Realty

  100 Legion Rd, Newfane, VT 05345
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  /14

  Not Listed For Sale

  5 Lahar Rd, Marlboro, VT 05351

  5 Lahar Rd, Marlboro, VT 05351
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  /18

  $120,000

  • Land
  • 2.84 Acres
  • $42,254 per Acre

  111 Gib Lockerby Rd, Grafton, VT 05146

  Nestled in the rolling hills of southern Vermont, just minutes above the charming center of Grafton, this professionally developed parcel of land beckons you to build your Vermont dream home. This open and sunny lot, complete with its own small apple orchard is surrounded by timeless stone walls and lovely woodlands. Choose the best building site for you; the cleared front acre, formerly a

  

  Christopher Cummings

  Cummings & Co

  (802) 424-8491

  111 Gib Lockerby Rd, Grafton, VT 05146
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  $1,600 per month

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  498 Marlboro Rd Unit N26, West Brattleboro, VT 05301

  Property Id: 1510774Newly renovated two bedroom apartment for rent in a professionally managed apartment building in West Brattleboro, Vermont. Clean, bright, with wood floors, new appliances, on-site laundry and off-street parking. Rents include heat and hot water. All units are non smoking. Small pets would require approval and an additional security deposit.

  498 Marlboro Rd Unit N26, West Brattleboro, VT 05301
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  /35

  $770,000 Sold Mar 12, 2025

  62 Yeaw Rd, Dover, VT 05341

  • 4 Beds
  • 3 Baths
  • 2,942 Sq Ft
  • Built 2005

  Last Sold Summary

  • 9% Below List Price
  • $262/SF
  • 212 Days On Market

  Current Estimated Value $796,897

  Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  62 Yeaw Rd, Dover, VT 05341
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  Est $529,773 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,050 Sq Ft

  208 Shady Ln, West Wardsboro, VT 05360

  208 Shady Ln, West Wardsboro, VT 05360
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  /52

  $1,725,000

  • 4 Beds
  • 3.5 Baths
  • 2,698 Sq Ft

  122 Sunbowl Ridge Rd, Stratton, VT 05360

  Solstice has long been considered the very finest townhome development at Stratton Mountain. With an unparalleled slope side location and private amenities such as heated pool and tub , private shuttle service. This four bedroom four bath townhome is the ultimate ski and summer getaway. Beautifully redone. One car heated garage, family room.

  John Sikes Stratton Real Estate

  122 Sunbowl Ridge Rd, Stratton, VT 05360
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  /6

  $1,700 per month

  • 2 Beds
  • 1 Bath
  • 671 Sq Ft
  • Apartment for Rent

  1889 Vermont 30 Unit 1, Townshend, VT 05353

  First Floor 2 bedroom apartment with natural light, close to town and is available now. Off street parking and a yard make the location ideal. Apartment is not furnished

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  1889 Vermont 30 Unit 1, Townshend, VT 05353
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  /37

  $340,000 Sold Aug 14, 2025

  290 Melendy Hill Rd, South Londonderry, VT 05155

  • 3 Beds
  • 3 Baths
  • 2,809 Sq Ft
  • Built 1936

  Last Sold Summary

  • 15% Below List Price
  • $121/SF
  • 159 Days On Market

  Current Estimated Value $346,823

  Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

  290 Melendy Hill Rd, South Londonderry, VT 05155
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  /40

  Est $368,271 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,358 Sq Ft

  965 Western Ave, Brattleboro, VT 05301

  965 Western Ave, Brattleboro, VT 05301
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  /35

  $2,399,000

  • 4 Beds
  • 4.5 Baths
  • 3,569 Sq Ft

  662 Howe Farm Rd, Jamaica, VT 05343

  Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, adding a touch of

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  662 Howe Farm Rd, Jamaica, VT 05343
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  /6

  $1,800 per month

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  91 Central St Unit 2, Brattleboro, VT 05301

  Property Id: 2252475This furnished one-bedroom apartment in Downtown Brattleboro is available starting at $1800 month (all utilities included). This is an outstanding opportunity for medical professionals as it's located within a 10 minute-walk from Brattleboro Memorial Hospital and the Brattleboro Retreat. However, this could work for anyone interested in a mid-term rental between a

  91 Central St Unit 2, Brattleboro, VT 05301
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  $200,000 Sold Oct 17, 2025

  533 Pratt Bridge Rd, Jamaica, VT 05343

  • 3 Beds
  • 2 Baths
  • 2,613 Sq Ft
  • Built 1970

  Last Sold Summary

  • 27% Below List Price
  • $77/SF
  • 25 Days On Market

  Current Estimated Value $274,658

  Last Listing Agent Mike England Michael England Real Estate

  533 Pratt Bridge Rd, Jamaica, VT 05343
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  /24

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 1,178 Sq Ft

  30 Styles Branch Rd Unit 307, Stratton, VT 05360

  30 Styles Branch Rd Unit 307, Stratton, VT 05360
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  /79

  $275,000

  • Land
  • 22.32 Acres
  • $12,321 per Acre

  81 Parish Hill Rd Unit 26, Newfane, VT 05345

  Tucked away in the quiet hills of South Newfane, Vermont, this property presents an excellent opportunity to own a secluded off-grid retreat with endless potential. Spanning 22.32 acres of mixed timberland, the land offers both natural beauty and outdoor recreation, while the cabin provides a comfortable base that is already well on its way to completion.The cabin itself measures 715 square feet

  Chad Bruyette Whitetail Properties Real Estate

  81 Parish Hill Rd Unit 26, Newfane, VT 05345
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  /8

  $1,700 per month

  • 1 Bed
  • 1 Bath
  • 400 Sq Ft
  • Apartment for Rent

  4 Elliot St Unit 3, Brattleboro, VT 05301

  The National, featuring this 1 Bedroom apartment with bright sunlit rooms, amazing hardwood floors and views of downtown. Coin operated Laundry is on site and off-street parking is available in the parking garage. The building is pet friendly

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  4 Elliot St Unit 3, Brattleboro, VT 05301
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  $1,743,600 Sold Sep 30, 2025

  1324 Middle Rd, Brattleboro, VT 05301

  • 7 Beds
  • 7.5 Baths
  • 8,718 Sq Ft
  • Built 2005

  Last Sold Summary

  • 50% Below List Price
  • $200/SF
  • 274 Days On Market

  Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  1324 Middle Rd, Brattleboro, VT 05301
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  /17

  Est $499,447 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,309 Sq Ft

  38 Summit Meadows Cir, Dover, VT 05356

  38 Summit Meadows Cir, Dover, VT 05356

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