31,016

Windham County, VT Homes

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  • /40

    $395,000

    $10K PRICE INCREASE Under Contract
    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    315 Windham Springs Rd, West Townshend, VT 05359

    Discover your perfect Vermont getaway in this well-maintained 3 BR, 2 BA home. Designed for both relaxation and year-round adventure, this property places you minutes from southern Vermont's best skiing and charming village life. The first level offers ultimate convenience, featuring a roomy, tiled mud room for all your gear, two comfortable BRs, full bath and a private primary suite complete

    Agent Photo

    Christopher Cummings

    Cummings & Co

    315 Windham Springs Rd, West Townshend, VT 05359
  • /20

    $1,875 Per Month

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

    167 Howard Rd Unit 2, Wardsboro, VT 05355

    Property Id: 2203648 One bedroom one bathroom apartment can be rented furnished or unfurished upon tenants request (furnished rent anount $1925) Apartment is located off of route 100 in Wardsboro Village on a dead end road. Travel to Mt Snow and ski areas roughly 20 minutes also convenient to local hospital/health center and amenities. All kitchen appliances are new stainless steel,

    167 Howard Rd Unit 2, Wardsboro, VT 05355
  • /21

    $319,000

    Sold May 14, 2026

    6 Longest Dr Unit 1, Wilmington, VT 05363

    • 3 Beds
    • 2.5 Baths
    • 1,510 Sq Ft
    • Built 1986

    Last Sold Summary

    • 6% Below List Price
    • $211/SF
    • 50 Days On Market

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    6 Longest Dr Unit 1, Wilmington, VT 05363
    • /29

      Est $351,202

      Not Listed For Sale

      64 Meadowbrook Rd, Brattleboro, VT 05301

      • 4 Beds
      • 2 Baths
      • 1,352 Sq Ft
      • Built 1890
      64 Meadowbrook Rd, Brattleboro, VT 05301

      Last Sold Summary

      • 16 Days On Market

  • /22

    $670,000

    • Land
    • 67 Acres
    • $10,000 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

    Agent Photo

    Ross Doody

    Century 21 Highview Realty

    00 S Pine Banks Rd, Putney, VT 05346
  • /19

    $1,850 Per Month

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

    30 Laurel Ave Unit 2, Town of Rockingham, VT 05101

    Property Id: 2753890 Close proximity to all major hospitals with access to route 5 and US 91 just minutes away. The apartment is in a quiet working class neighborhood. The apartment is on the second floor in a large Farmhouse Victorian in historic village of Bellows Falls with stores and restaurantw within easy walking distance. The apartment itself has a spacious kitcen and living room

    30 Laurel Ave Unit 2, Town of Rockingham, VT 05101
  • /17

    $200,000

    Sold Jan 16, 2026

    75 Mather Rd, Brattleboro, VT 05301

    • 1 Bed
    • 1 Bath
    • 720 Sq Ft
    • Built 1959

    Last Sold Summary

    • 4% Below List Price
    • $278/SF
    • 6 Days On Market

    Current Estimated Value $204,281

    Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty

    75 Mather Rd, Brattleboro, VT 05301
    • /16

      Est $159,836

      Not Listed For Sale

      41 Henry St, Bellows Falls, VT 05101

      • 4 Beds
      • 2,490 Sq Ft
      • Built 1880
      41 Henry St, Bellows Falls, VT 05101

      Last Sold Summary

      • 14 Days On Market

  • /57

    $695,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    124 Forrester Rd, Stratton, VT 05360

    Bucolic Mountain Retreat. 6 Minutes to Stratton Sun Bowl.Escape to your own private 43.7-acre Vermont paradise, offering a perfect blend of serene country living and resort convenience. Situated just six minutes from the Stratton Mountain Sun Bowl, this impeccably maintained 3-bedroom, 2-bath Cape is enveloped by beautifully landscaped grounds featuring mature lilacs, historic apple trees,

    Agent Photo

    Lauren Behm

    Berkshire Hathaway HomeServices Stratton Home

    124 Forrester Rd, 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
  • /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

    Current Estimated Value $505,967

    Last Listing Agent John Hatton Berkley & Veller Greenwood Country

    321 Leonard Rd, Dummerston, VT 05301
    • /14

      Est $257,678

      Not Listed For Sale

      17 Wardon Rd, Putney, VT 05346

      • 3 Beds
      • 1 Bath
      • 1,144 Sq Ft
      • Built 1974
      17 Wardon Rd, Putney, VT 05346

      Last Sold Summary

      • 34 Days On Market

  • /37

    $529,000

    • 3 Beds
    • 3 Baths
    • 1,688 Sq Ft

    190 Route 11 Unit 2, Peru, VT 05152

    Open House Saturday, July 25th, 10-12!Escape to the heart of Southern Vermont in this recently renovated chalet-style mountain home, where timeless charm meets four-season recreation. Being sold fully furnished. Ideally located under 25 minutes from four premier ski resorts - Bromley, Stratton, Magic, and Okemo - this inviting retreat offers the perfect balance of adventure and relaxation.

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    190 Route 11 Unit 2, Peru, VT 05152
  • /12

    $1,600

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    1063 Marlboro Rd Unit 2, Brattleboro, VT 05301

    West Brattleboro quiet area owned parking and porch

    1063 Marlboro Rd Unit 2, Brattleboro, VT 05301
  • /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 $390,949

    Last Listing Agent Teddy Kramer Berkley & Veller Greenwood Country

    2456 Deer Park Rd, West Halifax, VT 05358
    • /17

      Est $208,955

      Not Listed For Sale

      2147 N Main St, Londonderry, VT 05148

      • 3 Beds
      • 2 Baths
      • 1,414 Sq Ft
      • Built 1880
      2147 N Main St, Londonderry, VT 05148

      Last Sold Summary

      • 26 Days On Market

  • /38

    $495,000

    $20K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,115 Sq Ft

    367 Stratton Gate Rd, Jamaica, VT 05343

    Nestled on 2.4 private acres along desirable Stratton Gate Road, this well-maintained four-bedroom, three-bath home offers the perfect balance of comfort, space, and year-round recreation. Just minutes from Stratton Mountain, you’ll enjoy easy access to skiing, golf, hiking, mountain biking, and all that Southern Vermont has to offer.Designed for gathering and relaxing, the home features two

    Agent Photo

    Alison Cummings

    Cummings & Co

    367 Stratton Gate Rd, Jamaica, VT 05343
  • /21

    $2,100

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Townhouse for Rent

    240 Fairview St, Brattleboro, VT 05301

    Comfortable spacious freshly renovated and updated 2 bedroom duplex. 1st floor living and dining, large kitchen, 2nd floor 2 bedrooms, office/sitting, bathroom. Laundry in warm dry basement. TV & high speed WiFi. Large front porch, big backyard, parking for 1 car. Friendly safe neighborhood with lots of mature trees & greenery. 5 minute walk to hiking trails and hospital. 1 mile to downtown.

    240 Fairview St, Brattleboro, VT 05301
  • /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
    • /49

      Est $540,477

      Not Listed For Sale

      8686 Jacksonville Stage Rd, West Halifax, VT 05358

      • 4 Beds
      • 2 Baths
      • 2,884 Sq Ft
      • Built 1820
      8686 Jacksonville Stage Rd, West Halifax, VT 05358

      Last Sold Summary

      • 48 Days On Market

  • /23

    $122,000

    $5K PRICE DROP
    • Land
    • 2.07 Acres
    • $58,937 per Acre

    191 Pingree Park Ln, Londonderry, VT 05148

    2.07 acres with 140' riverfront bordering the west bank of pristine Utley Brook with headwaters flowing from the national forest. This waterfront parcel has is fully engineered with a fully permitted septic 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

    Agent Photo

    Alison Cummings

    Cummings & Co

    191 Pingree Park Ln, Londonderry, VT 05148
  • /5

    $2,700

    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
  • /27

    $245,000

    Sold Jan 16, 2026

    4668 Vermont 112, Halifax, VT 05342

    • 2 Beds
    • 1 Bath
    • 1,155 Sq Ft
    • Built 1860

    Last Sold Summary

    • 2% Below List Price
    • $212/SF
    • 30 Days On Market

    Last Listing Agent Chris Long BHG Masiello Brattleboro

    4668 Vermont 112, Halifax, VT 05342
    • /42

      Est $419,126

      Not Listed For Sale

      44 Russell Rd, Guilford, VT 05301

      • 3 Beds
      • 2 Baths
      • 1,440 Sq Ft
      • Built 1900
      44 Russell Rd, Guilford, VT 05301

      Last Sold Summary

      • 30 Days On Market

  • /60

    $3,800,000

    $2M PRICE DROP
    • 4 Beds
    • 8 Baths
    • 16,736 Sq Ft

    1950 Collins Rd, Brattleboro, VT 05301

    Exceptional 177+ Acre Estate with Luxury Log Home, Event Venue & Craft Beverage Facilities. Experience unmatched luxury and opportunity on this remarkable 177+ acre estate. Featuring an 8,000+ sq ft timber frame log home, a 7,100 sq ft finished event venue, and on-site winery, craft brewery, and champagne-making facilities, this turn-key property is ideal as a private residence, retreat, or

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    1950 Collins Rd, Brattleboro, VT 05301
  • /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
  • /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

    Current Estimated Value $403,716

    Last Listing Agent Donna Brown Skihome Realty

    52 Edward's Village Loop, Dover, VT 05356
    • /37

      Est $443,230

      Not Listed For Sale

      880 Green River Rd, Brattleboro, VT 05301

      • 3 Beds
      • 1 Bath
      • 1,608 Sq Ft
      • Built 1983
      880 Green River Rd, Brattleboro, VT 05301

      Last Sold Summary

      • 48 Days On Market

  • /23

    $135,000

    $5K PRICE INCREASE
    • Land
    • 2.19 Acres
    • $61,644 per Acre

    192 Pingree Park Ln, Londonderry, VT 05148

    2.17 acres with 199' of riverfront bordering the west bank of pristine Utley Brook with headwaters flowing from the national forest. This waterfront parcel has is fully engineered with a fully permitted septic 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

    Agent Photo

    Alison Cummings

    Cummings & Co

    192 Pingree Park Ln, Londonderry, VT 05148
  • /13

    $2,200 Per Month

    • 2 Beds
    • 1 Bath
    • 1,545 Sq Ft
    • House for Rent

    78 Central St, 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, Brattleboro, VT 05301
  • /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 $78,187

    Last Listing Agent Christine Lewis Brattleboro Area Realty

    100 Legion Rd, Newfane, VT 05345
    • /29

      Est $534,626

      Not Listed For Sale

      103 Dover Hill Rd, East Dover, VT 05341

      • 3 Beds
      • 2 Baths
      • 2,188 Sq Ft
      • Built 1987
      103 Dover Hill Rd, East Dover, VT 05341

      Last Sold Summary

      • 57 Days On Market

  • /43

    $535,000

    • 4 Beds
    • 2 Baths
    • 1,816 Sq Ft

    176 Brophy Ln, Londonderry, VT 05148

    Discover this charming Vermont log cabin, situated on a quiet, secluded lot just 5 minutes from downtown Londonderry, and 15 minutes to downtown Manchester's restaurants and shopping. This home offers the perfect balance of peaceful mountain living and easy access to local amenities. The first level welcomes you into a large, open-concept living room, dining room, and kitchen area, perfect for

    Agent Photo

    Christopher Cummings

    Cummings & Co

    176 Brophy Ln, Londonderry, VT 05148
  • /19

    $70,000 Per Month

    • 4 Beds
    • 4 Baths
    • 2,000 Sq Ft
    • House for Rent

    16 c Winterberry Heights, Stratton, VT 05155

    Best of the Best. Ski on Ski off. Pristine clean unit, very well maintained and original owners. Largest Treetops there is.. 4 bedroom/4 bath, den family room, amazing views, brand new hot tub.. everything you want and need for an amazing winter season. Loads of room for family and guests and entertaining. Enjoy all that Stratton has to offer as well as all the other ski areas close by and

    Wilkie Bushby TPW Real Estate

    16 c Winterberry Heights, Stratton, VT 05155
  • /44

    $425,000

    Sold May 06, 2026

    1909 Davidson Hill Rd, Westminster, VT 05158

    • 3 Beds
    • 2 Baths
    • 1,684 Sq Ft
    • Built 1950

    Last Sold Summary

    • 1% Below List Price
    • $252/SF
    • 103 Days On Market

    Current Estimated Value $419,305

    Last Listing Agent Steve Schoppmeyer BHG Masiello Brattleboro

    1909 Davidson Hill Rd, Westminster, VT 05158
    • /50

      Est $496,156

      Not Listed For Sale

      2194 Mowrey Rd, Jamaica, VT 05343

      • 2 Beds
      • 1.5 Baths
      • 1,346 Sq Ft
      • Built 2003
      2194 Mowrey Rd, Jamaica, VT 05343

      Last Sold Summary

      • 47 Days On Market

  • /31

    $245,000

    $14K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    51 Golding Rd, Windham, VT 05359

    Tucked away on a quiet dead end dirt road in the heart of Windham, this cute Vermont log home offers the kind of peace and privacy that is getting harder to find. Set in a clearing of four acres of wooded land, this property feels like a private retreat, surrounded by conservation land and abundant wildlife. The log home blends rustic charm with comfortable living. The warm wood finishes on the

    Agent Photo

    Alison Cummings

    Cummings & Co

    51 Golding Rd, Windham, VT 05359
  • /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
  • /26

    $315,000

    Sold Apr 14, 2026

    9047 Vermont 30, Jamaica, VT 05155

    • 2 Beds
    • 2 Baths
    • 976 Sq Ft
    • Built 1940

    Last Sold Summary

    • 3% Below List Price
    • $323/SF
    • 20 Days On Market

    Last Listing Agent Carrie Mathews Winhall Real Estate

    9047 Vermont 30, Jamaica, VT 05155
    • /25

      Est $342,774

      Not Listed For Sale

      6 Willow St, Brattleboro, VT 05301

      • 4 Beds
      • 1.5 Baths
      • 1,503 Sq Ft
      • Built 1928
      6 Willow St, Brattleboro, VT 05301

      Last Sold Summary

      • 42 Days On Market

Showing Results 1 - 40, Page 1 of 18

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