30,889

Windham County, VT Homes

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  • /51

    $799,000

    • 4 Beds
    • 5 Baths
    • 3,992 Sq Ft

    1035 Vermont 121, Windham, VT 05359

    Set on 17 private acres off Route 121, this Windham property delivers the space, flexibility, and access buyers are looking for in Southern Vermont. The open-concept main level is anchored by a grand living room with cathedral ceilings, hardwood floors, and a gas fireplace, flowing easily into a generous dining area designed to host large gatherings and a well-equipped kitchen with coffee bar. A

    Jamie Wylie Stratton Real Estate

    1035 Vermont 121, Windham, VT 05359
  • /26

    $1,500

    Total Monthly Price

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

    11 Chestnut St Unit Second Floor, Brattleboro, VT 05301

    ? Spacious 1 Bedroom + Office Apartment – $1,500/month ?Don’t miss this bright and generously sized second-floor apartment offering 1 bedroom plus a separate office space.Perfectly situated in a desirable neighborhood close to the hospital and within walking distance to downtown, this location offers both convenience and easy access to local amenities.1 off-street parking

    11 Chestnut St Unit Second Floor, Brattleboro, VT 05301
  • /36

    $405,500

    Sold Jan 29, 2026

    44 Villager Loop, Dover, VT 05356

    • 3 Beds
    • 3 Baths
    • 2,144 Sq Ft
    • Built 1987

    Last Sold Summary

    • 25% Below List Price
    • $189/SF
    • 480 Days On Market

    Current Estimated Value $402,988

    Last Listing Agent Janet Boyd Boyd Real Estate

    44 Villager Loop, Dover, VT 05356
    • /32

      Est $488,918

      Not Listed For Sale

      476 Edie Ln, Jamaica, VT 05343

      • 3 Beds
      • 3 Baths
      • 1,800 Sq Ft
      • Built 1988
      476 Edie Ln, Jamaica, VT 05343

      Last Sold Summary

      • 40 Days On Market

  • /24

    $899,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft

    19 Village Lodge Rd Unit 409, Stratton, VT 05155

    Landmark 409 offers a rare combination of mountain views, resort convenience, and strong rental performance in one of Stratton's most desirable condominium locations. This two-level residence is positioned to capture views of Stratton Mountain while providing a comfortable layout designed for both personal enjoyment and guest use.The main living area centers around a gas fireplace, creating

    Jamie Wylie Stratton Real Estate

    19 Village Lodge Rd Unit 409, Stratton, VT 05155
  • /5

    $2,600

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Condo for Rent

    93 Winterbell Dr Unit 93 winterbell Drive, East Dummerston, VT 05346

    3 bedroom; 2 bath, Private Drive; cable ready; high speed internet access; Rural on 2 acres.

    93 Winterbell Dr Unit 93 winterbell Drive, East Dummerston, VT 05346
  • /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 $353,116

    Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

    290 Melendy Hill Rd, South Londonderry, VT 05155
    • /24

      Est $229,848

      Not Listed For Sale

      1751 Rockingham Rd, Rockingham, VT 05143

      • 2 Beds
      • 1.5 Baths
      • 1,120 Sq Ft
      • Built 1989
      1751 Rockingham Rd, Rockingham, VT 05143

      Last Sold Summary

      • 14 Days On Market

  • /33

    $915,000

    • 3 Beds
    • 2.5 Baths
    • 1,529 Sq Ft

    761 Stratton Mountain Access Rd Unit 321/323, Stratton, VT 05360

    A rare opportunity in Long Trail House, this corner residence has been thoughtfully reimagined from two separate units into a spacious, fully renovated retreat designed for flexible living. The expanded layout now includes multiple sleeping areas and a den/office, offering versatility for guests or remote work. Natural light fills the home thanks to its corner position, while open living space

    Edwin Kevil Stratton Real Estate

    761 Stratton Mountain Access Rd Unit 321/323, Stratton, VT 05360
  • /11

    $2,100

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Townhouse for Rent

    2864 Fort Bridgman Rd Unit 2, Vernon, VT 05354

    This property at 2864 Fort Bridgman Rd Unit #3 features 3 levels; a finished basement with laundry; 1st floor with kitchen/Livingroom and 2rd floor with bedrooms and bathroom. totaling 2 bedrooms and 1 bathroom within a total of 1,000 square feet. The living room offers ample space for relaxation and entertainment, while the bathroom includes a tub/shower combination for convenience. Each

    2864 Fort Bridgman Rd Unit 2, Vernon, VT 05354
  • /34

    $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 $229,472

    Last Listing Agent Mike England Michael England Real Estate

    533 Pratt Bridge Rd, Jamaica, VT 05343
    • /14

      Not Listed For Sale

      5 Lahar Rd, Marlboro, VT 05351

      5 Lahar Rd, Marlboro, VT 05351

      Last Sold Summary

      • 9 Days On Market

  • /33

    $1,760,000

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

    89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360

    This Sun Bowl townhome delivers true ski-in/ski-out access, offering direct connection to Stratton's slopes right from your door. Designed for both comfort and functionality, the home features a bright, open layout with hardwood floors and a striking floor-to-ceiling stone fireplace that defines the main living space. Spanning multiple levels, the layout provides flexibility for hosting and

    Edwin Kevil Stratton Real Estate

    89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360
  • /12

    $2,700 Per Month

    • 3 Beds
    • 1.5 Baths
    • 2,100 Sq Ft
    • House for Rent

    176 Harrington Rd, West Townshend, VT 05359

    SUMMER SEASONAL RENTAL!!Charming well kept log home tucked away in a country setting in Windham. Three bedrooms and a loft. Centrally located between Chester, Grafton and Londonderry. A great getaway to enjoy all of what VT has to offer (summer activities, wildlife and hiking trails to name a few). Fully furnished and all inclusive for $2,700.00 per month. Tenant pays trash removal. Available

    Team BVA Rentals Barrett and Valley Associates Inc.

    176 Harrington Rd, West Townshend, VT 05359
  • /54

    $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

    Current Estimated Value $1,690,839

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    1324 Middle Rd, Brattleboro, VT 05301
    • /36

      Est $531,802

      Not Listed For Sale

      208 Shady Ln, West Wardsboro, VT 05360

      • 3 Beds
      • 2.5 Baths
      • 2,050 Sq Ft
      • Built 2006
      208 Shady Ln, West Wardsboro, VT 05360

      Last Sold Summary

      • 5 Days On Market

  • /79

    $189,900

    $85K PRICE DROP
    • Land
    • 22.32 Acres
    • $8,508 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
  • /14

    $1,650 Per Month

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Condo for Rent

    100 Clark St Unit 2, Brattleboro, VT 05301

    100 Clark St Unit 2, Brattleboro, VT 05301
  • /59

    $360,000

    Sold Sep 26, 2025

    45 Dorr Fitch Rd, West Dover, VT 05356

    • 5 Beds
    • 3.5 Baths
    • 2,800 Sq Ft
    • Built 1968

    Last Sold Summary

    • 14% Below List Price
    • $129/SF
    • 10 Days On Market

    Current Estimated Value $360,307

    Last Listing Agent Rich Caplan Deerfield Valley Real Estate

    45 Dorr Fitch Rd, West Dover, VT 05356
    • /48

      Est $589,425

      Not Listed For Sale

      418 Diers, Jamaica, VT 05343

      • 3 Beds
      • 2.5 Baths
      • 2,621 Sq Ft
      • Built 1988
      418 Diers, Jamaica, VT 05343

      Last Sold Summary

      • 4 Days On Market

  • /8

    $275,000

    $80K PRICE DROP Under Contract
    • Land
    • 34.53 Acres
    • $7,964 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 3 is 34.53 acres, and is mostly forested near the access road. A driveway would need to be

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /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. PICTURES ARE VIRTUALLY STAGED- APARTMENT IS NOT FURNISHED

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    4 Elliot St Unit 2, Brattleboro, VT 05301
  • /10

    $82,000

    Sold Jan 07, 2026

    0 Old Ledge Rd Unit 4950217, Westminster, VT 05346

    • Land
    • 5 Acres
    • $16,400 per Acre

    Last Sold Summary

    • 9% Below List Price
    • 928 Days On Market

    Last Listing Agent Christine Lewis Brattleboro Area Realty

    0 Old Ledge Rd Unit 4950217, Westminster, VT 05346
    • /40

      Not Listed For Sale

      965 Western Ave, Brattleboro, VT 05301

      • 4 Beds
      • 3 Baths
      • 2,358 Sq Ft
      • Built 1840
      965 Western Ave, Brattleboro, VT 05301

      Last Sold Summary

      • 55 Days On Market

  • /39

    $499,000

    $20K PRICE DROP
    • Land
    • 80.11 Acres
    • $6,229 per Acre

    47 Whites Hill Rd, Dover, VT 05341

    Escape to Your Private 80-Acre Paradise – Nature, Adventure, and Opportunity Await! Discover the perfect blend of natural beauty and endless outdoor adventure on this breathtaking 80-acre property, nestled in a peaceful and pristine setting. With towering maple trees ready for harvesting or simply to enjoy for their beauty and shade, this land offers both recreational enjoyment and income

    Joe Castaluccio Winhall Real Estate

    47 Whites Hill Rd, Dover, VT 05341
  • /17

    $2,200 Per Month

    • 2 Beds
    • 1 Bath
    • 1,525 Sq Ft
    • 78-80 Central Street LLC

    78 Central St Unit 2, Brattleboro, VT 05301

    This second floor, two-bedroom apartment in town on a quiet side street. This unit has had some updates to the kitchen and bathroom, along with fresh paint throughout. The rooms have amazing sunlight throughout the day and enjoy the evenings on your enclosed porch. This is close to shopping, public transportation and schools. Rent does not include any utilities. Photos are virtually staged,

    78 Central St Unit 2, Brattleboro, VT 05301
  • /46

    $480,000

    Sold Oct 28, 2025

    28 Dover Green Rd, Dover, VT 05356

    • 4 Beds
    • 2 Baths
    • 2,092 Sq Ft
    • Built 1975

    Last Sold Summary

    • 4% Below List Price
    • $229/SF
    • 29 Days On Market

    Current Estimated Value $454,962

    Last Listing Agent Kim Meeker Southern Vermont Realty Group

    28 Dover Green Rd, Dover, VT 05356
    • /23

      Not Listed For Sale

      00 Stagecoach, Grafton, VT 05146

      00 Stagecoach, Grafton, VT 05146

      Last Sold Summary

      • 86 Days On Market

  • /11

    $495,000

    $170K PRICE DROP Under Contract
    • Land
    • 68.89 Acres
    • $7,185 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 4 is 68.89 acres and is the largest of the five parcels for sale. This lot has a solid woods

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /7

    $1,500 Per Month

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

    3031 Vermont 30 Unit 1, Townshend, VT 05353

    One bedroom apartment with heat and electric included in the rent. Newly renovated with bright sunlit rooms. This one bedroom is just outside the town center in Townshend with off street parking

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    3031 Vermont 30 Unit 1, Townshend, VT 05353
  • /60

    $535,000

    Sold Jun 20, 2025

    78 Pond Loop Unit M-2, Wilmington, VT 05363

    • 5 Beds
    • 2.5 Baths
    • 2,800 Sq Ft
    • Built 1968

    Last Sold Summary

    • 8% Below List Price
    • $191/SF
    • 200 Days On Market

    Current Estimated Value $562,356

    Last Listing Agent Sigrid Pickering Chimney Hill Realty

    78 Pond Loop Unit M-2, Wilmington, VT 05363
    • /24

      Not Listed For Sale

      30 Styles Branch Rd Unit 307, Stratton, VT 05360

      • 4 Beds
      • 3.5 Baths
      • 1,178 Sq Ft
      • Built 1979
      30 Styles Branch Rd Unit 307, Stratton, VT 05360

      Last Sold Summary

      • 7 Days On Market

  • /12

    $99,000

    $900K PRICE DROP
    • Land
    • 12.2 Acres
    • $8,115 per Acre

    Higley Hill Rd, Wilmington, VT 05363

    Looking for Vermont land with privacy, natural beauty, and development potential? This 12.2-acre parcel in Windham County offers a peaceful escape tucked into the woods, ideal for buyers seeking recreational land, a homestead site, or a rural retreat. With 250 ft of road frontage on Higley Hill Rd, the property is easily accessible while still offering seclusion.The terrain is wooded and

    Community Lands Community Lands

    Higley Hill Rd, Wilmington, VT 05363
  • /13

    $2,200 Per Month

    • 2 Beds
    • 1 Bath
    • 1,525 Sq Ft
    • 78-80 Central Street LLC

    78 Central St Unit 1, Brattleboro, VT 05301

    This first floor, two-bedroom apartment in town on a quiet side street. This unit has had some updates to the kitchen and bathroom, along with fresh paint throughout. The rooms have amazing sunlight throughout the day and enjoy the evenings on your enclosed porch. This is close to shopping, public transportation and schools. Rent does not include any utilities. Photos are virtually staged,

    78 Central St Unit 1, Brattleboro, VT 05301
  • /32

    $190,000

    Sold Apr 29, 2026

    36 Barker St, Town of Rockingham, VT 05101

    • 3,302 Sq Ft
    • Built 1880

    Last Sold Summary

    • 17% Below List Price
    • $58/SF
    • 9 Days On Market

    Current Estimated Value $194,500

    Last Listing Agent Rob Weltz Barrett and Valley Associates Inc.

    36 Barker St, Town of Rockingham, VT 05101
    • /17

      Est $449,391

      Not Listed For Sale

      38 Summit Meadows Cir, Dover, VT 05356

      • 4 Beds
      • 3 Baths
      • 1,309 Sq Ft
      • Built 1984
      38 Summit Meadows Cir, Dover, VT 05356

      Last Sold Summary

      • 12 Days On Market

  • /7

    $195,000

    $40K PRICE DROP Under Contract
    • Land
    • 15.27 Acres
    • $12,770 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 2 is 15.27 acres and is the first parcel found on the left side of the newly built 20 foot

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /31

    $500 Per Month

    • 2 Baths
    • 352 Sq Ft
    • House for Rent

    21 Vermont 121 Unit 1,2,4,5,6, Grafton, VT 05146

    OFFICE SPACE AVAILABLE. The Windham Walkups now available for rent. Second floor office spaces now available above the Grafton Garage in Grafton Village VT. 5 separate office spaces are available and vary in rent based on size from $475-$650/month. Rent includes heat, electric and plowing. Shared parking area located just behind building. Two shared bathrooms and kitchenette space. Work remotely

    Jessica Landers Barrett and Valley Associates Inc.

    21 Vermont 121 Unit 1,2,4,5,6, Grafton, VT 05146
  • /22

    $69,000

    Sold Oct 03, 2025

    1051 Maple Hill Ln, Whitingham, VT 05342

    • Land
    • 10.01 Acres
    • $6,893 per Acre

    Last Sold Summary

    • 3 Days On Market

    Last Listing Agent Kelly Agrillo Southern Vermont Realty Group

    1051 Maple Hill Ln, Whitingham, VT 05342
    • /30

      Est $621,380

      Not Listed For Sale

      79 Wilmington Heights, Wilmington, VT 05363

      • 4 Beds
      • 3 Baths
      • 2,200 Sq Ft
      • Built 1987
      79 Wilmington Heights, Wilmington, VT 05363

      Last Sold Summary

      • 97 Days On Market

Showing Results 41 - 80, Page 2 of 18

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