30,509

Windham County, VT Homes

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  • /37

    $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

    Agent Photo

    Alison Cummings

    Cummings & Co

    (802) 317-7411

    3298 Houghtonville Rd, Grafton, VT 05146
  • /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
  • /30

    $105,000 Sold Dec 03, 2025

    • 1,968 Sq Ft
    • $53/SF
    • 97 Days On Market
    • Built 1910

    10 Taylor St, Town of Rockingham, VT 05101

    INVESTER SPECIAL! This 2-unit property has separate utilities, 2-3 bedroom units on each floor depending on how the layout is set up. Rooms are generously sized, front and side porches for each unit, full basement and attic.This would make a nice generational or family home or a great starter home with rental potential.

    Julie Buffum Buffum Realty

    10 Taylor St, Town of Rockingham, VT 05101
    • /20

      Est $559,856 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,036 Sq Ft

      78 Middle Ridge Rd Unit 102, Stratton, VT 05155

      78 Middle Ridge Rd Unit 102, Stratton, VT 05155
  • /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
  • /9

    $1,700 per month

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

    4 Elliot St Unit 11, Brattleboro, VT 05301

    In town, one bedroom apartment, with bright sunlit rooms. The apartment has a combined kitchen and living room, with a separate bedroom. Coin operated laundry is on site, trash removal, and a secure building. Pet friendly building

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    4 Elliot St Unit 11, Brattleboro, VT 05301
  • /60

    $680,000 Sold Dec 03, 2025

    • 2,170 Sq Ft
    • $313/SF
    • 128 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2005

    27 Stearns Ave, Wilmington, VT 05363

    Nestled in the heart of Vermont’s Green Mountains, check out this stunning Moosehead log home. With private, shared access to Lake Raponda just a short walk away, this inviting single-family home seamlessly blends rustic charm, modern comfort, and a serene natural setting. With 2,170 sq. ft. of living space, this 3-bedroom, 2-bath home welcomes you with warmth and tranquility from the moment you

    John Redd Skihome Realty

    27 Stearns Ave, Wilmington, VT 05363
    • /28

      Est $758,110 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
  • /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
  • /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
  • /60

    $535,000 Sold Dec 01, 2025

    • 3,000 Sq Ft
    • $178/SF
    • 233 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1985

    121 Dover Hill Rd, Dover, VT 05341

    Highly motivated sellers. Ideal for remote workers or second-home buyers, this Vermont retreat offers fiber-optic internet, energy-efficient systems, no water or sewer bills, and some of the state's lowest property taxes. Set on 5 private acres just minutes from Mount Snow and Grout Pond, this move-in ready home supports low-cost living with high quality of life. The updated kitchen features new

    Nick Sicard EXP Realty

    121 Dover Hill Rd, Dover, VT 05341
    • /11

      Est $279,686 Not Listed For Sale

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

      48 Loop Rd, Newfane, VT 05345

      48 Loop Rd, Newfane, VT 05345
  • /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

    Agent Photo

    Ross Doody

    Century 21 Highview Realty

    (802) 499-2391

    00 S Pine Banks Rd, Putney, VT 05346
  • /11

    $1,650 per month

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

    110 Estey St Unit 3, Brattleboro, VT 05301

    This quaint 3rd floor apartment on a quiet side street in town. The apartment is partially furnished, with one off street parking space. The rent includes heat and electric. This unit shares laundry facilities with the apartment downstairs. This apartment as unique as it comes with individual rooms for the shower, sink and toilet. There is also an additional loft space for storage. Its a must see

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    110 Estey St Unit 3, Brattleboro, VT 05301
  • /34

    $185,000 Sold Nov 26, 2025

    • 800 Sq Ft
    • $231/SF
    • 10 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1800

    4 Gove St, Bellows Falls, VT 05101

    This very sweet village home is tucked into a quiet neighborhood, set on a terrace above the village. Bursting with character, it features an open concept flow, hardwood floors, mini split, beadboard accents, and large windows that fill the rooms with light. While the classic charm remains, thoughtful upgrades have been made for comfort and efficiency, including blown-in insulation, a heat pump,

    Katie Ladue Gilbert KW Vermont Woodstock

    4 Gove St, Bellows Falls, VT 05101
    • /33

      Est $262,421 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 856 Sq Ft

      849 Mcmillan Rd, Halifax, VT 05342

      849 Mcmillan Rd, Halifax, VT 05342
  • /40

    $379,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,874 Sq Ft

    254 Boynton Rd Unit 3, Londonderry, VT 05148

    Riverside Farm condominiums are uniquely designed and situated in a rural setting along a country road in Londonderry, VT, close to some of the area's best attractions. Quiet and serene with a view of the West River and surrounding countryside, these residences provide the Vermont lifestyle with the convenience of shared maintenance and amenities. This attractively renovated unit in the lower

    Agent Photo

    Beth Vickers

    Vermont Real Estate Company

    (802) 330-8072

    254 Boynton Rd Unit 3, Londonderry, VT 05148
  • /20

    $12,964 per month

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

    3A Black Pine Unit ID1261564P, Dover, VT 05356

    This gorgeous three-bedroom condo is situated directly across from Mount Snow, offering everything you need for the perfect getaway. Whether you're planning a ski trip in the winter, an action-packed summer vacation, or a relaxing fall leaf-peeping trip, this is a great spot to call your home away from home. Wake up in the morning and take in the beautiful views of Mount Snow from your windows;

    3A Black Pine Unit ID1261564P, Dover, VT 05356
  • /14

    $780,000 Sold Nov 25, 2025

    • 1,263 Sq Ft
    • $618/SF
    • 46 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2000

    19 Village Lodge Rd Unit 309, Stratton, VT 05155

    In the heart of the Stratton Mountain Village attached to the iconic Clock Tower, Landmark is prime location for all that that the Resort has to offer. This two bedroom floorplan is one of the largest in the community. Ample living and bedroom space as well as a nice separate dining area. Direct mountain views with southern exposure for warm light. Beautifully appointed furniture and ready for

    Timothy Mich Doddridge Stratton Real Estate

    19 Village Lodge Rd Unit 309, Stratton, VT 05155
    • /8

      Est $772,330 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,244 Sq Ft

      438 River Rd, Guilford, VT 05301

      438 River Rd, Guilford, VT 05301
  • /43

    $565,000 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 2,149 Sq Ft

    66 Hilltop Rd, Londonderry, VT 05155

    This great home is a must see! Fully renovated in the past 8 months, from floor to ceilings, every inch has been updated. Brand new kitchen and baths, all new fixtures and appliances, this 4 bedroom 3 bath home is waiting for new owners to enjoy it! Great proximity to skiing, recreation, groceries and dining, yet private and set back from the road. Sold furnished with a pleasing neutral palate,

    Agent Photo

    Alison Cummings

    Cummings & Co

    (802) 553-3290

    66 Hilltop Rd, Londonderry, VT 05155
  • /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
  • /21

    $590,000 Sold Nov 25, 2025

    • 916 Sq Ft
    • $644/SF
    • 306 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1999

    771 Stratton Mountain Access Rd Unit 261, Stratton, VT 05360

    771 Stratton Mountain Access Rd, Stratton, VT 05155 Long Trail House is Stratton’s #1 location for owners who wish to combine personal use with an optional rental offset when not in residence. Walk to Village shops, restaurants and ski lifts. The floor plan for Long Trail House #261 is one of the largest of the 2 bedroom layouts. Master bedrooms has nice views of the Village Common. Great light

    Andrew King Stratton Real Estate

    771 Stratton Mountain Access Rd Unit 261, Stratton, VT 05360
    • /32

      Est $445,562 Not Listed For Sale

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

      476 Edie Ln, Jamaica, VT 05343

      476 Edie Ln, Jamaica, VT 05343
  • /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
  • /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
  • /19

    $46,277 Sold Nov 25, 2025

    • Land
    • 1.43 Acres
    • $32,362 per Acre
    • 16 Days On Market

    1114 Abbott Rd, Windham, VT 05359

    Dreaming of building your own quiet camp, ski home, or full time residence nestled away in the beautiful and quaint town of Windham? Look no further than this peaceful 1.43+/- lot that is just waiting to see what you design for a home or camp. The property boasts many great features such as- stream frontage, access to the VAST trail, quiet dirt roads for walking, many ski resorts not far away,

    Erin Kendall EXP Realty

    1114 Abbott Rd, Windham, VT 05359
    • /24

      Est $234,667 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
  • /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
  • /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
  • /32

    $340,000 Sold Nov 25, 2025

    • 1,215 Sq Ft
    • $280/SF
    • 96 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1979

    5 Blackberry Ln, West Dover, VT 05356

    Classic Vermont chalet with modern septic and timeless charm! Nestled on a serene one-acre lot, this classic Vermont chalet offers both tranquility and character. A brand-new four-bedroom septic system ensures peace of mind for the fortunate new owners. Step inside to a spacious mudroom entry that leads to a convenient half bath with laundry. The open-concept main level features a beamed ceiling,

    Monique White Deerfield Valley Real Estate

    5 Blackberry Ln, West Dover, VT 05356
    • /14

      Not Listed For Sale

      5 Lahar Rd, Marlboro, VT 05351

      5 Lahar Rd, Marlboro, VT 05351
  • /12

    $999,000

    • Land
    • 12.2 Acres
    • $81,885 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
  • /9

    $1,800 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
  • /37

    $659,000 Sold Nov 25, 2025

    • 2,400 Sq Ft
    • $275/SF
    • 285 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1987

    83B Greenspring, Dover, VT 05356

    Imagine stepping into a pristine mountain townhome that feels like a warm embrace, complete with modern updates and breathtaking views of the surrounding peaks. The moment you enter, a spacious mudroom welcomes you, perfectly designed to accommodate all your outdoor gear and winter jackets. This three-bedroom plus den, 3.5-bath gem boasts a sun-drenched open floor plan where the living and dining

    Sheila Joyce-Albano Skihome Realty

    83B Greenspring, Dover, VT 05356
    • /36

      Est $517,501 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
  • /8

    $275,000

    • 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
  • /26

    $500 per month

    • 2 Baths
    • 352 Sq Ft
    • House for Rent

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

    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 $425-$650/month. Rent includes heat, electric and plowing. Shared parking area located just behind building. Two shared bathrooms and kitchenette space. Work remotely but would rather

    Jessica Landers Barrett and Valley Associates Inc.

    21 Vermont 121 Unit 1,2,4,5,6, Grafton, VT 05146
  • /31

    $399,000 Sold Nov 25, 2025

    • 1,854 Sq Ft
    • $215/SF
    • 124 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1984

    132 Sun and Ski Rd, Wilmington, VT 05363

    Welcome to Chateau Chelsea! This charming three-level, 4-bedroom, 3-bathroom single-family home is situated in the heart of Vermont’s picturesqueGreen Mountains. Named after the owners' beloved pup, this property has been a cherished gathering place for family and friends year-round. Conveniently located just over 2 hours from Boston, 90 minutes from Hartford, CT, and less than 4 hours from NYC,

    Patrice Schneider Southern Vermont Realty Group

    132 Sun and Ski Rd, Wilmington, VT 05363
    • /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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