30,778

Windham County, VT Homes

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  • /45

    $789,000

    • 4 Beds
    • 3.5 Baths
    • 2,856 Sq Ft

    15 Sawmill Village Way, Dover, VT 05356

    If you are looking for a quality-built, well-maintained home with modern updates and built-in property maintenance near Mt. Snow, this Village at Sawmill Farms home checks all the boxes. Located just up the hill from the businesses and services of West Dover, near the Mt. Snow golf course, recreational trails, and 2.5 miles from the ski resort, this home is situated perfectly to enjoy the area's

    Agent Photo

    Beth Vickers

    Vermont Real Estate Company

    (802) 341-9969

    15 Sawmill Village Way, Dover, VT 05356
  • /11

    $2,400 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 $469,604

    Last Listing Agent John Hatton Berkley & Veller Greenwood Country

    321 Leonard Rd, Dummerston, VT 05301
    • /27

      Est $255,447 Not Listed For Sale

      1871 Wilmington Cross Rd, Whitingham, VT 05361

      • 5 Beds
      • 2.5 Baths
      • 2,428 Sq Ft
      • Built 1840
      1871 Wilmington Cross Rd, Whitingham, VT 05361

      Last Sold Summary

      • 195% Above List Price
      • $36/SF
      • 49 Days On Market
      • Last Sold Price $86,700
      • Apr 18, 2025

      Last Listing Agent Kim Meeker Southern Vermont Realty Group

  • /33

    $319,000

    • 3 Beds
    • 2 Baths
    • 1,310 Sq Ft

    1829 W Jamaica Rd, Jamaica, VT 05343

    Vermont Charming! Tucked away along a peaceful river in Jamaica, Vermont this charming cape offers the perfect blend of privacy, character and convenience just 4 miles from Stratton Mountain Resort. With three bedrooms and one and three quarters baths, the home has been thoughtfully maintained and updated while preserving its classic New England charm. Recent upgrades to the kitchen and bathrooms

    Agent Photo

    Alison Cummings

    Cummings & Co

    (802) 471-3958

    1829 W Jamaica Rd, Jamaica, VT 05343
  • /16

    $2,200 per month

    • 2 Beds
    • 1 Bath
    • 1,525 Sq Ft
    • Apartment for Rent

    80 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,

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    80 Central St, Brattleboro, VT 05301
  • /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 $199,440

    Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty

    75 Mather Rd, Brattleboro, VT 05301
    • /24

      Est $256,458 Not Listed For Sale

      16 Beam Rd, Putney, VT 05346

      • 3 Beds
      • 1 Bath
      • 1,260 Sq Ft
      • Built 1970
      16 Beam Rd, Putney, VT 05346

      Last Sold Summary

      • 221% Above List Price
      • $63/SF
      • 96 Days On Market
      • Last Sold Price $80,000
      • Apr 18, 2025

      Last Listing Agent Linda Benoit Highland Realty

  • /31

    $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
  • /14

    $3,700 per month

    • 4 Beds
    • 2.5 Baths
    • 1,374 Sq Ft
    • House for Rent

    38 Snow Rd, Dover, VT 05341

    Property Id: 2358823This fully furnished two-story home offers a practical setup that works beautifully for traveling professionals, families on assignment, or anyone looking for a peaceful mid-term stay in southern Vermont. The house strikes a balance between privacy, flexibility, and shared living areas that feel easy to settle into from the start.The main level features an open

    38 Snow Rd, Dover, VT 05341
  • /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 $395,055

    Last Listing Agent Teddy Kramer Berkley & Veller Greenwood Country

    2456 Deer Park Rd, West Halifax, VT 05358
    • /20

      Not Listed For Sale

      869 Cow Path 40, Marlboro, VT 05301

      • 4 Beds
      • 2.5 Baths
      • 2,092 Sq Ft
      • Built 1932
      869 Cow Path 40, Marlboro, VT 05301

      Last Sold Summary

      • $155/SF
      • 44 Days On Market
      • Last Sold Price $325,000
      • Apr 17, 2025

      Last Listing Agent John Hatton 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
  • /15

    $2,200 per month

    • 2 Beds
    • 1 Bath
    • 1,525 Sq Ft
    • Apartment for Rent

    78 Central St, 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,

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    78 Central 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
    • /30

      Not Listed For Sale

      268/70/72 Q2,89 Grand Summit Way, Dover, VT 05356

      • 3 Beds
      • 3 Baths
      • 1,272 Sq Ft
      • Built 1998
      268/70/72 Q2,89 Grand Summit Way, Dover, VT 05356

      Last Sold Summary

      • $40/SF
      • 42 Days On Market
      • Last Sold Price $51,000
      • Apr 18, 2025

      Last Listing Agent Kelly Agrillo Southern Vermont Realty Group

  • /18

    $120,000 Under Contract

    • 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 sunny

    Agent Photo

    Christopher Cummings

    Cummings & Co

    (802) 424-8491

    111 Gib Lockerby Rd, Grafton, VT 05146
  • /5

    $1,300 per month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    498 Marlboro Rd Unit N16, Brattleboro, VT 05301

    Property Id: 15107631 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 $1,300/month. Book your viewing today!

    498 Marlboro Rd Unit N16, Brattleboro, VT 05301
  • /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
    • /34

      Not Listed For Sale

      170 Tanglewood Ln Unit 44C, Dover, VT 05356

      • 3 Beds
      • 2 Baths
      • 2,016 Sq Ft
      • Built 1988
      170 Tanglewood Ln Unit 44C, Dover, VT 05356

      Last Sold Summary

      • $255/SF
      • 57 Days On Market
      • Last Sold Price $515,000
      • Apr 18, 2025

      Last Listing Agent David White OwnerEntry.com

  • /54

    $639,900 Under Contract

    • 3 Beds
    • 3 Baths
    • 2,700 Sq Ft

    98 Gleason Farm Ln, Jamaica, VT 05343

    Nestled within a peaceful pine grove on 11.5 private acres between Stratton Mountain Resort and Mount Snow, this renovated 3-bedroom, 3-bathroom residence offers the perfect blend of secluded Vermont beauty and modern design. The heart of the home is a dramatic great room featuring 20+ foot soaring ceilings, skylights, and expansive windows that flood the space with natural light. On chilly

    Agent Photo

    Lauren Behm

    Berkshire Hathaway HomeServices Stratton Home

    (802) 988-7628

    98 Gleason Farm Ln, Jamaica, VT 05343
  • /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 $405,591

    Last Listing Agent Donna Brown Skihome Realty

    52 Edward's Village Loop, Dover, VT 05356
    • /23

      Est $559,976 Not Listed For Sale

      17 Darrah Loop, Wilmington, VT 05363

      • 3 Beds
      • 2 Baths
      • 2,234 Sq Ft
      • Built 2025
      17 Darrah Loop, Wilmington, VT 05363

      Last Sold Summary

      • 9% Above List Price
      • $229/SF
      • 90 Days On Market
      • Last Sold Price $512,500
      • Apr 18, 2025

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /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
  • /9

    $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
  • /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 $81,701

    Last Listing Agent Christine Lewis Brattleboro Area Realty

    100 Legion Rd, Newfane, VT 05345
    • /31

      Not Listed For Sale

      1383 Packer Corners Rd, Guilford, VT 05301

      • 0.5 Baths
      • 900 Sq Ft
      • Built 1975
      1383 Packer Corners Rd, Guilford, VT 05301

      Last Sold Summary

      • $133/SF
      • 104 Days On Market
      • Last Sold Price $120,000
      • Apr 18, 2025

      Last Listing Agent Jennifer Hovey-Densmore Deerfield Valley Real Estate

  • /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
  • /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
  • /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
    • /32

      Est $283,438 Not Listed For Sale

      38 Pine Tree Hill, Londonderry, VT 05148

      • 2 Beds
      • 1 Bath
      • 864 Sq Ft
      • Built 1966
      38 Pine Tree Hill, Londonderry, VT 05148

      Last Sold Summary

      • 6% Above List Price
      • $310/SF
      • 117 Days On Market
      • Last Sold Price $267,500
      • Apr 21, 2025

      Last Listing Agent Jacki Murano Southern Vermont Realty Group

  • /60

    $849,000

    • 5 Beds
    • 4.5 Baths
    • 3,840 Sq Ft

    42 Blackberry Ln, Jamaica, VT 05343

    Welcome to "Sweet Berry Farm", a charming Vermont homestead blending 1850s character with a spacious modern addition. Set on 5.7 private acres in Jamaica, this property offers abundant natural beauty—mature apple trees, blueberry and blackberry bushes and vibrant seasonal gardens. The expanded farmhouse provides exceptional space for living and entertaining. The main floor features an open living

    MaryKate Grey Stratton Real Estate

    42 Blackberry Ln, Jamaica, VT 05343
  • /11

    $2,400 total monthly price

    • 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 $433,035

    Last Listing Agent Janet Boyd Boyd Real Estate

    44 Villager Loop, Dover, VT 05356
    • /48

      Est $2,268,290 Not Listed For Sale

      9 Lodge Ln, Dover, VT 05356

      • 6 Beds
      • 4.5 Baths
      • 4,884 Sq Ft
      • Built 2005
      9 Lodge Ln, Dover, VT 05356

      Last Sold Summary

      • 7% Above List Price
      • $435/SF
      • 231 Days On Market
      • Last Sold Price $2,125,000
      • Apr 18, 2025

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /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
  • /29

    $2,500 per month

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

    85 Parker Hill Rd, Bellows Falls, VT 05101

    Open House Saturday April 4th 3pm to 5pm! 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

    Steve Schoppmeyer BHG Masiello Brattleboro

    85 Parker Hill Rd, Bellows Falls, VT 05101
  • /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 $355,271

    Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

    290 Melendy Hill Rd, South Londonderry, VT 05155
    • /31

      Not Listed For Sale

      5 Snow Drift Ln, Londonderry, VT 05155

      • 4 Beds
      • 2 Baths
      • 1,350 Sq Ft
      • Built 1968
      5 Snow Drift Ln, Londonderry, VT 05155

      Last Sold Summary

      • $263/SF
      • 2 Days On Market
      • Last Sold Price $355,000
      • Apr 18, 2025

      Last Listing Agent Lisa Sullivan Four Seasons Sotheby's Int'l Realty

Showing Results 1 - 40, Page 1 of 18

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