30,690

Windham County, VT Homes

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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

    Agent Photo

    Christopher Cummings

    Cummings & Co

    (802) 424-8491

    111 Gib Lockerby Rd, Grafton, VT 05146
  • /8

    $1,850 per month

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

    3550 Coolidge Hwy Unit 2, Guilford, VT 05301

    Property Id: 1504084Find your peace in this adorable 1 bedroom, 2 bathroom unit in Guilford, VT. This second floor property at 3550 Coolidge Highway offers top amenities including full kitchen w/ gas range, washer/dryer, covered balcony, glass shower, storage, and more. Small dogs allowed, utilities included. Available now!

    3550 Coolidge Hwy Unit 2, Guilford, VT 05301
  • /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 $520,241

    Last Listing Agent John Hatton Berkley & Veller Greenwood Country

    321 Leonard Rd, Dummerston, VT 05301
    • /31

      Est $465,546 Not Listed For Sale

      9 Lilla Ln, Wilmington, VT 05363

      • 3 Beds
      • 2 Baths
      • 1,827 Sq Ft
      • Built 1971
      9 Lilla Ln, Wilmington, VT 05363

      Last Sold Summary

      • 2% Above List Price
      • $249/SF
      • 10 Days On Market

      Last Sold Price $455,000

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /54

    $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

    Agent Photo

    Alison Cummings

    Cummings & Co

    (802) 416-4003

    192 Pingree Park Ln, Londonderry, VT 05148
  • /14

    $1,400 per month

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

    227 Rockingham St Unit 3, Bellows Falls, VT 05101

    Nicely renovated third-floor 2-bedroom apartment just minutes from downtown Bellows Falls. This bright unit features a full bathroom with views of the Connecticut River, a walk-in pantry, and a secure storage area outside the unit for additional space. Conveniently located within walking distance to village amenities and just 20 minutes to Brattleboro and Keene. Earliest move-in date: 04/01/2026.

    Paul Rodenhauser BHG Masiello Keene

    227 Rockingham St Unit 3, Bellows Falls, 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 $208,000

    Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty

    75 Mather Rd, Brattleboro, VT 05301
    • /39

      Est $431,203 Not Listed For Sale

      559 Pratt Bridge Rd, Jamaica, VT 05343

      • 4 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 1978
      559 Pratt Bridge Rd, Jamaica, VT 05343

      Last Sold Summary

      • 5% Above List Price
      • $333/SF
      • 181 Days On Market

      Last Sold Price $410,000

      Last Listing Agent Joe Castaluccio Winhall Real Estate

  • /60

    $4,950,000

    • 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

    (802) 317-7158

    1950 Collins Rd, Brattleboro, VT 05301
  • /16

    $2,000 per month

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft
    • House for Rent

    298 Sweet Pond Rd, Guilford, VT 05301

    Property Id: 23909593 Bedroom Ranch on 1-acre.Quiet location, beautiful country setting.5 miles from the Guilford Country Store.15 minutes to Brattleboro VT, 20 minutes to Greenfield, MA.Easy access to I-91 & Rte. 5UnfurnishedNew renovationsNew Exterior paint: Slate BlueOil, hot water baseboard heatingGas Range stoveWasher and dryer hook-ups in

    298 Sweet Pond Rd, Guilford, 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 $393,000

    Last Listing Agent Teddy Kramer Berkley & Veller Greenwood Country

    2456 Deer Park Rd, West Halifax, VT 05358
    • /37

      Est $493,961 Not Listed For Sale

      56 Linden St, Brattleboro, VT 05301

      • 3 Beds
      • 3.5 Baths
      • 2,884 Sq Ft
      • Built 1930
      56 Linden St, Brattleboro, VT 05301

      Last Sold Summary

      • 6% Above List Price
      • $161/SF
      • 101 Days On Market

      Last Sold Price $464,500

      Last Listing Agent David Brown

  • /50

    $859,000 Under Contract

    • 7 Beds
    • 5 Baths
    • 3,104 Sq Ft

    11 Waldwinkle Rd, Dover, VT 05356

    Discover this turnkey mountain retreat boasting 7 bedrooms and 5 baths, located just minutes from Mount Snow. Whether you're looking for an investment with proven rental history or a spacious getaway, this home delivers. Highlights include dual living areas and fireplaces, plus modern updates throughout—including updated flooring, baths, and kitchen—with plenty of room for large groups. Relax in

    Agent Photo

    Lauren Behm

    Berkshire Hathaway HomeServices Stratton Home

    (802) 480-9811

    11 Waldwinkle Rd, Dover, VT 05356
  • /7

    $2,100 per month

    • 2 Beds
    • 2 Baths
    • 1,650 Sq Ft
    • House for Rent

    3292 Vt Route 100 N, Londonderry, VT 05148

    Beautifully maintained 2 bedroom home in South Londonderry, VT. Back patio to enjoy the immaculate gardens and the VT outdoors. 1st floor hosts a large eat in kitchen, livingroom, laundry room and full bath. 2nd floor has 2 oversized bedrooms with built-ins and a 3/4 bath. Tenant is responsible for all utilities and services. Credit Check and References required for move in.

    Team BVA Rentals Barrett and Valley Associates Inc.

    3292 Vt Route 100 N, Londonderry, VT 05148
  • /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
    • /40

      Est $371,378 Not Listed For Sale

      6928 Vt Route 30, West Townshend, VT 05359

      • 3 Beds
      • 2 Baths
      • 1,413 Sq Ft
      • Built 1961
      6928 Vt Route 30, West Townshend, VT 05359

      Last Sold Summary

      • 16% Above List Price
      • $226/SF
      • 79 Days On Market

      Last Sold Price $320,000

      Last Listing Agent Jessica Flannery EXP Realty

  • /56

    $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

    Agent Photo

    Alison Cummings

    Cummings & Co

    (802) 613-9168

    191 Pingree Park Ln, Londonderry, VT 05148
  • /20

    $9,005 per month

    • 3 Beds
    • 3 Baths
    • 1,194 Sq Ft
    • Condo for Rent

    3A Black Pine Unit SI ID1261564P, Dover, VT 05356

    The advertised rate of $9,005/month is the lowest available price, based on a 1 month(s) stay with a move-in date of April 24, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    3A Black Pine Unit SI ID1261564P, Dover, VT 05356
  • /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
    • /29

      Not Listed For Sale

      542 Vermont 121, Westminster, VT 05101

      • 4 Beds
      • 1 Bath
      • 1,143 Sq Ft
      • Built 1920
      542 Vermont 121, Westminster, VT 05101

      Last Sold Summary

      • $127/SF
      • 100 Days On Market

      Last Sold Price $145,000

      Last Listing Agent Kerry Mulverhill

  • /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

    Agent Photo

    Alison Cummings

    Cummings & Co

    (802) 392-0721

    410 Tallwood Cir, Londonderry, VT 05148
  • /29

    $2,500 per month

    • 2 Beds
    • 1 Bath
    • 1,456 Sq Ft
    • House for Rent

    85 Parker Hill Rd, Bellows Falls, VT 05101

    Rare chance to rent a stand-alone, two-bedroom home, privately located on a tranquil seven-acre lot. Open fields surround the house and a pathway leads down to a swimming hole under a railroad trestle on the Williams River. The home features an open-concept kitchen with a center island, a living room with hardwood floors and cathedral ceilings with a woodstove with brick hearth, and a dining area

    Steve Schoppmeyer BHG Masiello Brattleboro

    85 Parker Hill Rd, Bellows Falls, VT 05101
  • /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 $387,014

    Last Listing Agent Donna Brown Skihome Realty

    52 Edward's Village Loop, Dover, VT 05356
    • /39

      Est $1,064,055 Not Listed For Sale

      615 Beaver Pond Rd, Dummerston, VT 05301

      • 6 Beds
      • 5.5 Baths
      • 7,291 Sq Ft
      • Built 2010
      615 Beaver Pond Rd, Dummerston, VT 05301

      Last Sold Summary

      • 13% Above List Price
      • $130/SF
      • 4 Days On Market

      Last Sold Price $945,000

      Last Listing Agent Laura D'Angelo Berkley & Veller Greenwood Country

  • /60

    $674,950 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,386 Sq Ft

    56 Whitetail Dr, Vernon, VT 05354

    Properties of this scale and setting are a rare find. Designed with entertaining in mind, the home’s circulation flows effortlessly through a dramatic great room anchored by a striking two-story fireplace. The space opens seamlessly to the dining and kitchen areas and is framed by a wall of windows that lead to an expansive deck overlooking a tranquil pond. A statement staircase ascends to a

    Agent Photo

    Mathew Ghafoori

    RE/Max Heritage

    (802) 278-9432

    56 Whitetail Dr, Vernon, VT 05354
  • /6

    $1,350 per month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    498 Marlboro Rd Unit S35, Brattleboro, VT 05301

    Property Id: 15108101 bed, 1 bath apartment in Brattleboro, VT! This unit features modern amenities like a microwave, oven, and refrigerator. Enjoy off-street parking, on-site laundry, and a beautiful lawn. Pets are welcome! Don't miss out on this gem for $1,350/month. Book your viewing today!

    498 Marlboro Rd Unit S35, 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 $91,596

    Last Listing Agent Christine Lewis Brattleboro Area Realty

    100 Legion Rd, Newfane, VT 05345
    • /10

      Est $394,065 Not Listed For Sale

      11 West St, Putney, VT 05346

      • 3 Beds
      • Built 1880
      11 West St, Putney, VT 05346

      Last Sold Summary

      • 119% Above List Price
      • $98/SF
      • 27 Days On Market

      Last Sold Price $180,000

      Last Listing Agent Bill Hickok Berkley & Veller Greenwood Country

  • /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
  • /7

    $2,200 per month

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

    4 Elliot St Unit 5, Brattleboro, VT 05301

    Corner apartment in downtown Brattleboro in the National is located on the corner of Elliot and Main Street. This two-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 5, Brattleboro, VT 05301
  • /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 $806,572

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    62 Yeaw Rd, Dover, VT 05341
    • /28

      Est $807,008 Not Listed For Sale

      11 Country Club Rd, Wilmington, VT 05363

      • 5 Beds
      • 4.5 Baths
      • 3,876 Sq Ft
      • Built 1925
      11 Country Club Rd, Wilmington, VT 05363

      Last Sold Summary

      • 5% Above List Price
      • $199/SF
      • 189 Days On Market

      Last Sold Price $770,000

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /33

    $1,760,000

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

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

    Trailside!!! Ski in, ski out!! The very best Ski Direct Access at Stratton!! Most popular of luxury townhomes---offering an enlarged patio with Hot Tub, Open and Sunny, Four Bedrooms plus a Den Floorplan, Single Car Garage! Fully Furnished. Hardwood Flooring, floor to ceiling stone, wood burning fireplace! Enjoy this outstanding trailside location. And as an added benefit, the Stratton Training

    Edwin Kevil Stratton Real Estate

    89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360
  • /11

    $2,400 per month

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

    53 Dummerston Station Rd, East Dummerston, VT 05346

    Lease - prefer 1yr minimum Available - starting mid March. No Pets. No Smoking. 1st mo + Last + Security due on lease signing APPLICATION REQUIRED PRIOR TO VIEWING Single level 2br / 1ba home with detached garage and washer dryer hookups and

    53 Dummerston Station Rd, East Dummerston, VT 05346
  • /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 $519,417

    Last Listing Agent Janet Boyd Boyd Real Estate

    44 Villager Loop, Dover, VT 05356
    • /11

      Est $277,846 Not Listed For Sale

      48 Loop Rd, Newfane, VT 05345

      • 3 Beds
      • 2 Baths
      • 1,992 Sq Ft
      • Built 1973
      48 Loop Rd, Newfane, VT 05345

      Last Sold Summary

      • 6% Above List Price
      • $131/SF
      • 15 Days On Market

      Last Sold Price $261,000

      Last Listing Agent A.J. Bellville Bellville Realty

  • /52

    $1,725,000 Pending

    • 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
  • /17

    $2,300 per month

    • 2 Beds
    • 1 Bath
    • 930 Sq Ft
    • Townhouse for Rent

    60 Brookside Dr Unit 3, Brattleboro, VT 05301

    This warm and inviting 2-bedroom condo comes fully furnished with everything you will need to just move in and relax. The first-floor open concept kitchen/living room makes for easy entertaining while you cook dinner. Upstairs are both bedrooms and the 3/4 bathroom. This comes with a full basement that has the washer and dryer and still usable space for storage or another room. This condo is not

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    60 Brookside Dr Unit 3, Brattleboro, VT 05301
  • /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 $396,993

    Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

    290 Melendy Hill Rd, South Londonderry, VT 05155
    • /33

      Est $234,258 Not Listed For Sale

      849 Mcmillan Rd, Halifax, VT 05342

      • 1 Bed
      • 1 Bath
      • 856 Sq Ft
      • Built 2020
      849 Mcmillan Rd, Halifax, VT 05342

      Last Sold Summary

      • 12% Below List Price
      • $310/SF
      • 13 Days On Market

      Last Sold Price $265,000

      Last Listing Agent Jennifer Hovey-Densmore Deerfield Valley Real Estate

Showing Results 1 - 40, Page 1 of 18

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