30,391

Windham County, VT Homes

Section Image
    • /30

      Est $382,175 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,295 Sq Ft

      18 Castle Hill Rd, Wilmington, VT 05363

      18 Castle Hill Rd, Wilmington, VT 05363
  • /49

    $725,000

    • 4 Beds
    • 2.5 Baths
    • 3,104 Sq Ft

    153 Westminster Rd, Putney, VT 05346

    Combining the charm of an 1820's fully restored historic home, with a 1,600 sq. ft. addition (built in 2016), this fabulous property, close to the Putney Village, offers the best of both worlds. Wide pine flooring and exposed beams in the restored front half blend beautifully with the newly built addition, featuring 9’ ceilings, hardwood floors and a handsome stone fireplace. The expansive

    Heidi Bernier Berkley & Veller Greenwood Country

    153 Westminster Rd, Putney, VT 05346
  • /38

    $239,000 Sold Aug 14, 2025

    • 1,056 Sq Ft
    • $226/SF
    • 13 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1988

    81 Morningside Commons, Guilford, VT 05301

    The moment you step into this condo, you notice its unique features and feel a sense of calm. In the living room, you’ll enjoy the “Anywhere” ethanol fireplace for its ambience and extra heat - with no connections, venting or emissions to worry about! The kitchen has been carefully redone, with expanded cabinetry and improvements to the layout and lighting, including a custom display cabinet and

    Victoria Woods Brattleboro Area Realty

    81 Morningside Commons, Guilford, VT 05301
    • /34

      Est $666,914 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,148 Sq Ft

      72 Castle Hill Rd, Wilmington, VT 05363

      72 Castle Hill Rd, Wilmington, VT 05363
  • /60

    $625,000

    • 3 Beds
    • 2.5 Baths
    • 2,782 Sq Ft

    628 Townshend Rd, Grafton, VT 05146

    One of only two stone houses in the charming town of Grafton, this stately home is a truly special opportunity. Perched on a hill across from the renowned Grafton Cheese Company, the property offers easy access to village amenities and year-round recreation at Grafton Ponds Outdoor Center. Inside, you'll find a spacious and inviting layout: Large front living room with exposed beams, a beautiful

    Jessica Landers Barrett and Valley Associates Inc.

    628 Townshend Rd, Grafton, VT 05146
  • /23

    $290,450 Sold Aug 14, 2025

    • 1,473 Sq Ft
    • $197/SF
    • 24 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2006

    2705 Vermont Route 100, Wardsboro, VT 05355

    Welcome to this charming 3 bedroom home with great river frontage on the Wardsboro brook, situated along Vermont's Route 100 National Scenic Byway. With lots of windows and beautiful wood flooring, the home is very bright and cozy. There's a pellet stove to keep you extra warm when the Vermont winter sets in, and plenty of space to rest your head with two comfy bedrooms and one huge oversized

    Mike Masters Four Seasons Sotheby's Int'l Realty

    2705 Vermont Route 100, Wardsboro, VT 05355
    • /40

      Est $426,914 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,200 Sq Ft

      50 Ray Hill Rd, Wilmington, VT 05363

      50 Ray Hill Rd, Wilmington, VT 05363
  • /20

    $469,000

    • 4 Beds
    • 2 Baths
    • 2,219 Sq Ft

    45 Dover Hill Rd, East Dover, VT 05341

    Recently renovated 1900s Colonial just outside the town of Dover, near the Mount Snow ski resort and village of Wilmington, and near Lake Whitingham, with easy access off a paved town road. This cozy Vermont retreat sits on 3+ acres with established trails, a gurgling brook wrapping around the home, bridge to access the rear upper meadow, perennial landscaping, and more. The home is being offered

    Adam Palmiter Berkley & Veller Greenwood/Dover

    45 Dover Hill Rd, East Dover, VT 05341
  • /39

    $329,000 Sold Aug 14, 2025

    • 1,713 Sq Ft
    • $192/SF
    • 24 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1920

    158 Clark Ave, Brattleboro, VT 05301

    Lovingly refurbished and full of timeless charm, this two bedroom, one bathroom Arts and Crafts bungalow offers bright, comfortable living within a mile from Brattleboro Memorial Hospital and both the middle and high schools. Set on a beautifully level lot, the home features a welcoming enclosed porch, a covered outdoor dining area perfect for three-season enjoyment, and a built-in one-car garage

    Andie Fusco Four Seasons Sotheby's Int'l Realty

    158 Clark Ave, Brattleboro, VT 05301
    • /21

      Est $412,589 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,914 Sq Ft

      157 Minor Rd, Wilmington, VT 05363

      157 Minor Rd, Wilmington, VT 05363
  • /30

    $1,040,000

    • 5 Beds
    • 4.5 Baths
    • 3,363 Sq Ft

    1189 Cole Pond Rd, Jamaica, VT 05343

    Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts.The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    1189 Cole Pond Rd, Jamaica, VT 05343
  • /16

    $80,000 Sold Aug 14, 2025

    • Land
    • 10 Acres
    • $8,000 per Acre
    • 48 Days On Market

    Lot 4 North St, Dover, VT 05431

    Discover the perfect Vermont retreat on this 10.00 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape.Whether you

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    Lot 4 North St, Dover, VT 05431
    • /33

      Est $305,126 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,088 Sq Ft

      752 Route 9 E, Wilmington, VT 05363

      752 Route 9 E, Wilmington, VT 05363
  • /17

    $2,495,000

    • Land
    • 2.36 Acres
    • $1,057,203 per Acre

    4 Gold Medal Cir, Stratton, VT 05343

    This lot is only one mile from the Stratton Mountain Resort's Sun Bowl base area. The lot has views of Stratton's ski trails. The Powers Subdivision has 11 lots in total and 2.71 acres of common land. Additionally, there is 69 acres of conservation land making this community very private. Build your 4-bedroom dream home right here in one of the best planned communities in southern Vermont.

    Andrew King Stratton Real Estate

    4 Gold Medal Cir, Stratton, VT 05343
  • /39

    $377,500 Sold Aug 14, 2025

    • 3,224 Sq Ft
    • $117/SF
    • 34 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1899

    25 Westminster Terrace, Bellows Falls, VT 05101

    Nestled near the close of a dead-end road in the historic village of Bellows Falls with views of Fall Mountain in NH (the Connecticut River in between), this timeless Victorian owned by the same family for over forty-five years boasts many original features including several porches, ornate original woodwork, high ceilings, and a butler’s pantry. Upstairs you’ll find four bedrooms, a large

    Heather Gleim CENTURY 21 North East

    25 Westminster Terrace, Bellows Falls, VT 05101
    • /36

      Est $433,191 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft

      60 Hall Rd, Wilmington, VT 05363

      60 Hall Rd, Wilmington, VT 05363
  • /48

    $32,000

    • 1 Bed
    • 2 Baths
    • 846 Sq Ft

    226/228, Qtr 2 Grand Summit Way Unit 226/228, Qtr 2, Dover, VT 05356

    Experience the ultimate in flexibility and mountain living with this deeded quartershare at the Grand Summit Hotel. Enjoy 13 weeks of vacation annually—one week every 28 days—on a rotating basis. Use it, rent it, or trade it for other destinations! This spacious valley-side lockout unit comfortably sleeps 8 and features 2 full baths, a kitchen/dining area, and stunning valley views. Unit 226 is

    Donna Brown Skihome Realty

    226/228, Qtr 2 Grand Summit Way Unit 226/228, Qtr 2, Dover, VT 05356
  • /48

    $750,000 Sold Aug 14, 2025

    • 2,573 Sq Ft
    • $291/SF
    • 141 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1989

    573 Middletown Rd, Londonderry, VT 05148

    Wonderful four bedroom home in the desirable town of Londonderry, Vermont. Once part of the Janeway Farm and Middletown Dairy this property has served as a primary home for many years. Spacious home has four bedrooms with three en-suite bedrooms. Land is suitable for gardens and room for play. There is a garden shed and a work shop just behind the house for any hobbies or projects. Living room

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    573 Middletown Rd, Londonderry, VT 05148
    • /20

      Est $475,228 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,536 Sq Ft

      143 Sun and Ski Rd, Wilmington, VT 05363

      143 Sun and Ski Rd, Wilmington, VT 05363
  • /24

    $279,000

    • 3 Beds
    • 1 Bath
    • 912 Sq Ft

    91 Carriage Hill Rd, Brattleboro, VT 05301

    This charming split-level home offers 3 bedrooms and a full bathroom, complete with a single-bay garage in the desirable Carriage Hill neighborhood. Hardwood floors extend through the living room, hall, and bedrooms, adding warmth and character. The living room features a lovely picture window with opening side windows, perfect for letting in a refreshing breeze and natural light.The lower level

    Rebecca Seymour Brattleboro Area Realty

    91 Carriage Hill Rd, Brattleboro, VT 05301
  • /37

    $340,000 Sold Aug 14, 2025

    • 2,809 Sq Ft
    • $121/SF
    • 159 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1936

    290 Melendy Hill Rd, South Londonderry, VT 05155

    This charming and spacious home is tucked away on a quiet road just off Route 100 in South Londonderry. Featuring wood floors throughout, two wood stoves, and a fireplace, this home radiates warmth and character. With 3 bedrooms, 3 bathrooms, a large living room, dining room, den, office, laundry room, and a bonus room, there’s ample space to meet all your needs. Two decks and a screened porch

    Lauren Behm Berkshire Hathaway HomeServices Stratton Home

    290 Melendy Hill Rd, South Londonderry, VT 05155
    • /29

      Est $402,086 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 1,100 Sq Ft

      259 Vt Route 100 N, Wilmington, VT 05363

      259 Vt Route 100 N, Wilmington, VT 05363
  • /36

    $442,500

    • 4 Beds
    • 3.5 Baths
    • 2,794 Sq Ft

    87 Orchard St, Brattleboro, VT 05301

    Pleasant and comfortable! This inviting home offers four bedrooms, three and a half bathrooms, a choice of primary bedroom with ensuite bath on the first floor or on the second. Enjoy a pleasant open flow living, kitchen and dining with hard wood floors for entertaining or hosting your next book club. The first floor offers a cheerful step saver kitchen with a pantry, gas range and views to the

    Jim Bellville Bellville Realty

    87 Orchard St, Brattleboro, VT 05301
  • /27

    $450,000 Sold Aug 14, 2025

    • 841 Sq Ft
    • $535/SF
    • 175 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 2004

    19 Village Lodge Rd Unit 304, Stratton, VT 05155

    It’s all about location! Landmark is located within Stratton Mountain Resorts iconic clock tower, nestled within the heart of the village. This 1 bedroom plus bonus room, 1 bath Landmark unit is at the center of all that Stratton Mountain has to offer and is walking distance to village restaurants and shops. Enjoy the ease of two parking spaces, one on the upper deck and another one in the

    MaryKate Grey Stratton Real Estate

    19 Village Lodge Rd Unit 304, Stratton, VT 05155
    • /18

      Est $316,916 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,564 Sq Ft

      57 Riverside Dr, Wilmington, VT 05363

      57 Riverside Dr, Wilmington, VT 05363
  • /54

    $335,000

    • 5 Beds
    • 2 Baths
    • 1,944 Sq Ft

    2015 Vermont 30, Townshend, VT 05353

    Perfectly situated on the scenic road to Stratton Mountain—just 25 minutes from the slopes—this charming turn-of-the-century mixed-use property offers endless potential. Step inside to discover original period woodwork, gleaming hardwood floors, and classic details that give this roomy home its timeless character.The property also boasts a large two-story post-and-beam barn, lovingly restored

    Craig Ruggless EXP Realty

    2015 Vermont 30, Townshend, VT 05353
  • /16

    $130,000 Sold Aug 13, 2025

    • 1,331 Sq Ft
    • $98/SF
    • 12 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1987

    272 Landman Ln, Jamaica, VT 05343

    Jamaica Landman Lane off Cole Pond Rd. This 2.7 acres has a 3 bedroom septic, electricity and spring. Nice location... 15 minutes to 3 major Ski Resorts and golf, 30 minutes to Manchester shopping and dining. Close to Jamaica State Park great hiking. Seller has asked that all buyer be pre qualified, as this most likely will need to be a cash sale. SOLD AS IS. Home is compromised. No entry.

    Mike England Michael England Real Estate

    272 Landman Ln, Jamaica, VT 05343
    • /33

      Est $373,426 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,248 Sq Ft

      28 Happy Haven Rd, Wilmington, VT 05363

      28 Happy Haven Rd, Wilmington, VT 05363
  • /2

    $70,000

    • Land
    • 1.47 Acres
    • $47,619 per Acre

    0 Huckle Hill Rd Unit 5059719, Vernon, VT 05354

    Amazing Opportunity to Build Your Forever Home!This beautiful south-facing, open lot offers the perfect setting for your dream home, with convenient access to power right at the road. The back portion of the property is graced with mature trees, providing shade and a natural pathway to nearby VAST snowmobile and hiking trails.Enjoy the peace of a quiet country setting where you can

    Kerry Mulverhill

    0 Huckle Hill Rd Unit 5059719, Vernon, VT 05354
  • /53

    $685,000 Sold Aug 13, 2025

    • 3,695 Sq Ft
    • $185/SF
    • 109 Days On Market
    • 4 Beds
    • 5.5 Baths
    • Built 2005

    37 Spring Hill Rd, West Dover, VT 05356

    Discover the perfect blend of comfort and adventure in this stunning 4 bedroom, 6 bathroom home in the heart of Dover, VT. Boasting breathtaking mountain views, this property is just minutes from Mount Snow, premier golf courses, scenic walking trails, and the area's top restaurants. Step inside to find a bright, open-concept kitchen and dining area, ideal for gatherings.Each of the four bedrooms

    Jillian Wimmelman Deerfield Valley Real Estate

    37 Spring Hill Rd, West Dover, VT 05356
    • /40

      Est $672,800 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,600 Sq Ft

      143 Ray Hill Rd, Wilmington, VT 05363

      143 Ray Hill Rd, Wilmington, VT 05363
  • /10

    $360,000

    • 2 Beds
    • 2 Baths
    • 1,119 Sq Ft

    85 E Birch Rd Unit 15, Stratton, VT 05360

    Neighboring the Stratton Training and Fitness Center, Vantage Point offers two bedroom, two bath condominiums coveted for their convenience and southern exposure. Complete with large windows, wood burning fireplaces, full kitchens, and ample closet space, these units are perfect for growing families and couples who like to entertain. Residents enjoy private parking and complimentary shuttle to

    Edwin Kevil Stratton Real Estate

    85 E Birch Rd Unit 15, Stratton, VT 05360
  • /46

    $668,000 Sold Aug 12, 2025

    • 2,226 Sq Ft
    • $300/SF
    • 7 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1985

    395 Hillwinds Rd, Brattleboro, VT 05301

    Turnkey Home in Sought-After Hillwinds! Located in the desirable Hillwinds neighborhood and nestled among the trees, your dream home awaits! This charming and functional home offers open, sun-filled living spaces, softwood floors, and abundant storage. The kitchen is a cook’s dream, featuring granite countertops, a gas stove, farmhouse sink, and a unique pull-out cabinet on wheels for added

    Desiree Stango Berkley & Veller Greenwood Country

    395 Hillwinds Rd, Brattleboro, VT 05301
    • /24

      Est $567,128 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,836 Sq Ft

      252 Ray Hill Rd, Wilmington, VT 05363

      252 Ray Hill Rd, Wilmington, VT 05363
  • /51

    $845,000

    • 4 Beds
    • 4 Baths
    • 3,987 Sq Ft

    6235 Grafton Rd, Grafton, VT 05146

    1820 sunny farmhouse on 53 acres with comfortable additions, energy saving updates, and long frontage on Stiles Brook, running through the property. Recent first floor bedroom has handicap accessible adjoining bathroom (walk-in shower and clawfoot tub). Many windows have been replaced and full insulation added. One recent addition is the south-facing "sun room" - warm in the winter with its

    Judy Dickison Barrett & Valley Assoc. Inc

    6235 Grafton Rd, Grafton, VT 05146
  • /37

    $682,000 Sold Aug 12, 2025

    • 1,400 Sq Ft
    • $487/SF
    • 4 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1985

    5Q Northbrook Village Rd Unit A33, Dover, VT 05356

    One of a kind opportunity to be trailside at Mount Snow. This is a lofted 3 bedroom, 3 bath unit, and is one of the closest buildings at Seasons to the newly renovated amenities, meaning you can go to the pools, gym, hot tubs, and more, without having to get in your car on days when you take a break from skiing. Enjoy the large vaulted living space with stone floor to ceiling wood burning

    Adam Palmiter Berkley & Veller Greenwood/Dover

    5Q Northbrook Village Rd Unit A33, Dover, VT 05356
    • /23

      Est $231,994 Not Listed For Sale

      • 8 Beds

      290 Ray Hill Rd, Wilmington, VT 05363

      290 Ray Hill Rd, Wilmington, VT 05363
  • /35

    $649,000

    • 3 Beds
    • 3 Baths
    • 2,939 Sq Ft

    282 Melendy Hill Rd, South Londonderry, VT 05155

    Perfectly situated in the heart of Southern Vermont, this immaculate country Cape in South Londonderry offers the best of four-season living. Just minutes to Stratton, Magic, and Bromley Mountains, the property provides effortless access to skiing and snowboarding in winter. In summer, enjoy kayaking at Lowell Lake, golf at Stratton, or live theater at the Weston Playhouse. Everyday conveniences

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    282 Melendy Hill Rd, South Londonderry, VT 05155
  • /28

    $180,000 Sold Aug 12, 2025

    • 1,531 Sq Ft
    • $118/SF
    • 70 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1941

    316 Putney Rd, Brattleboro, VT 05301

    Convenient Location & Low Maintenance Living! Enjoy easy access to shopping, public transportation and waterfront with scenic trails. The backyard is just the right size for enjoying nature and a little fresh air. This charming home combines classic character with practical updates featuring a standing seam roof, vinyl windows and aluminum siding. Inside, the home radiates its original charm

    Kristen Ziter Taylor Brattleboro Area Realty

    316 Putney Rd, Brattleboro, VT 05301
    • /34

      Est $450,478 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,222 Sq Ft

      19 Strider Ln, Wilmington, VT 05363

      19 Strider Ln, Wilmington, VT 05363

Showing Results 241 - 280, Page 7 of 18

How to Buy a Home How to Finance a Home How to Sell a Home