30,391

Windham County, VT Homes

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  • /44

    $364,900

    • 4 Beds
    • 1.5 Baths
    • 2,316 Sq Ft

    16 Forest St, Bellows Falls, VT 05101

    Welcome to this beautifully maintained 4-bedroom, 2-bath New Englander, perfectly blending timeless character with modern updates. Nestled in the quintessential New England town of Rockingham, this home offers the warmth of history and the comfort of today’s conveniences.Step inside to find a recently painted interior, stunning natural woodwork, and gleaming floors throughout. The updated

    Bruce Murphy Keller Williams Realty Metro-Keene

    16 Forest St, Bellows Falls, VT 05101
  • /22

    $336,000 Sold Aug 12, 2025

    • 1,104 Sq Ft
    • $304/SF
    • 63 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1968

    62 Lawton Dr, Brattleboro, VT 05301

    Everything deserves a second chance, and this home found the right owner to love and recreate it in a stunning new life. Anyone who has looked at this home in the past few years, has to come back to see the shine....the fresh new look....the simplicity of move right in. Not only is this home refreshed stem to stern, it has new windows, siding, shingles, kitchen, bath.....and on and on! Tuck

    Christine Lewis Brattleboro Area Realty

    62 Lawton Dr, Brattleboro, VT 05301
    • /40

      Est $834,368 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,448 Sq Ft

      69 Woods Rd, Wilmington, VT 05363

      69 Woods Rd, Wilmington, VT 05363
  • /35

    $2,197,000

    • 5 Beds
    • 4.5 Baths
    • 5,110 Sq Ft

    14 Tarheel Trail, Wilmington, VT 05363

    This custom built 2018 log home, designed by RH Log Works and Hilderbrand Interiors, offers the ultimate in sophistication and luxury. Featured in Better Homes and Gardens, New England Home and Country Home magazines, this 5 bedroom, 4.5 bathroom sanctuary (plus extra bunk room) is nestled on 2.2 wooded acres with a river running alongside. Just 4 minutes from Hermitage Club and 10 minutes from

    Adam Palmiter Berkley & Veller Greenwood/Dover

    14 Tarheel Trail, Wilmington, VT 05363
  • /37

    $375,000 Sold Aug 12, 2025

    • 2,115 Sq Ft
    • $177/SF
    • 74 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1890

    3432 Us Route 5, Westminster, VT 05158

    A classic, stately Vermont Colonial wonderfully set on well over an acre of level land in Westminster, the oldest existing village in Vermont. This storied home was first the parsonage for the First Congregational Church, established in 1767. As was the custom of the time, the property was developed in phases. One of the first buildings was the large barn now situated behind the house, where

    Bill Hickok Berkley & Veller Greenwood Country

    3432 Us Route 5, Westminster, VT 05158
    • /28

      Est $433,734 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,972 Sq Ft

      93 Old Town Rd, Wilmington, VT 05363

      93 Old Town Rd, Wilmington, VT 05363
  • /32

    $425,000

    • 3 Beds
    • 1.5 Baths
    • 1,655 Sq Ft

    155 Upper Dummerston Rd, Brattleboro, VT 05301

    Great location! This 3-bedroom Colonial, built in 1920 (when houses were well-built) on Upper Dummerston Road is up the road from the Brattleboro Country Club and its golf course, cross country skiing, trails, and the West River. On a comfortable 0.75 level acres, this property is private but only 10 minutes from the center of town. Lots of windows bring in lots of light. Generous living room,

    John Hatton Berkley & Veller Greenwood Country

    155 Upper Dummerston Rd, Brattleboro, VT 05301
  • /5

    $100,000 Sold Aug 11, 2025

    • 700 Sq Ft
    • $143/SF
    • 19 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1966

    39 Brookside Dr Unit 7, Brattleboro, VT 05301

    Ready for a redo, this home is priced right for anyone who is handy with freshening, light carpentry (flooring) and other minor skills. Worth the effort to find an affordable option to renting or living with Mom! 48 hour a must for notice. This condo is located in a prime location with quick, easy access to I91 and a stones throw to the Whetstone Brook, Farmers Market and Living Memorial Park.

    Christine Lewis Brattleboro Area Realty

    39 Brookside Dr Unit 7, Brattleboro, VT 05301
    • /29

      Est $371,372 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,028 Sq Ft

      39 Stone Brook Rd, Wilmington, VT 05363

      39 Stone Brook Rd, Wilmington, VT 05363
  • /29

    $379,000

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft

    2D Polar Bear N, Dover, VT 05356

    Completely renovated townhome in the Bears Crossing community located on the ski-home trail from Mount Snow with direct shuttle service to and from the mountain as well. This unit sits conveniently located across from the amenities building yet with easy access to the shuttle and ski trail. Inside is a woodsy open concept floor plan with vaulted great room, wood burning fireplace and brick

    Adam Palmiter Berkley & Veller Greenwood/Dover

    2D Polar Bear N, Dover, VT 05356
  • /54

    $645,000 Sold Aug 11, 2025

    • 2,416 Sq Ft
    • $267/SF
    • 10 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1973

    22 Hillside Dr, Wilmington, VT 05363

    This reimagined 1970s ski chalet blends timeless architecture with cutting-edge design, offering 4 bedrooms and 3 bathrooms across nearly 4 private acres. Thoughtfully curated for both personal enjoyment and short-term rental potential, the home is turnkey-ready—just bring your suitcase.The entry level features two ensuite bedrooms, each with fully renovated 3⁄4 baths, and a spacious lounge

    Lauren Niles Coldwell Banker LIFESTYLES - Quechee

    22 Hillside Dr, Wilmington, VT 05363
    • /35

      Est $387,323 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,500 Sq Ft

      42 Old Town Rd, Wilmington, VT 05363

      42 Old Town Rd, Wilmington, VT 05363
  • /43

    $17,000

    • 1 Bath
    • 407 Sq Ft

    205, Qtr 3 89 Grand Summit Way Unit 205, Qtr 3, Dover, VT 05356

    Trailside! Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Own this deeded quartershare property for 1 week every 28 days, on a rotating basis. This slope-side studio with 1 full bath unit has sleeping space for 4, an open concept kitchen/dining room, and a large living room with a queen sleep sofa and a queen Murphy bed. Benefits of Grand Summit ownership include the best

    Donna Brown Skihome Realty

    205, Qtr 3 89 Grand Summit Way Unit 205, Qtr 3, Dover, VT 05356
  • /17

    $29,000 Sold Aug 11, 2025

    • Land
    • 1.1 Acres
    • $26,364 per Acre
    • 310 Days On Market

    0 Oak Hill Rd, Wardsboro, VT 05355

    Nice, wooded lot with mature trees as it's never been cut. Easy gradual grade, located in Snow Mountain Farms. Easy drive to Stratton or Mount Snow. No engineering done on this lot, selling raw land. Easy to walk and view anytime! Located on the corner of White and Oak Hill Road.

    Julie Lowe Lowe's Real Estate, LLC

    0 Oak Hill Rd, Wardsboro, VT 05355
    • /38

      Est $457,752 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,296 Sq Ft

      95 Davis Dr, Wilmington, VT 05363

      95 Davis Dr, Wilmington, VT 05363
  • /50

    $680,000

    • 4 Beds
    • 4 Baths
    • 2,590 Sq Ft

    196 Old Sawmill Rd, Londonderry, VT 05148

    Nestled in the Green Mountains just minutes from Magic Mountain Ski Area, this spacious 4-bedroom retreat offers the perfect Vermont lifestyle. Enjoy easy access to beautiful Lowell Lake, while tucked away on a quiet dead-end road with serene mountain views. Inside, the home features 3 private en suite bedrooms, two of which include cozy loft spaces, plus an additional guest room. A warm and

    Lee Brown Four Seasons Sotheby's Int'l Realty

    196 Old Sawmill Rd, Londonderry, VT 05148
  • /40

    $462,000 Sold Aug 08, 2025

    • 1,894 Sq Ft
    • $244/SF
    • 5 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1930

    34 Wiswall Hill Rd, Newfane, VT 05345

    BEST AND FINAL OFFERS DUE BY THURSDAY JULY 3rd at 9:00 AMThis country charmer blends the warmth and character of an antique cottage with tasteful modern updates for the perfect balance. Rich in personality, the home features exposed beams, brick hearths, wood floors, high ceilings, built-in bookshelves and dresser drawers, cozy corners, and spacious gathering areas. Just a few steps up from

    Jacki Murano Southern Vermont Realty Group

    34 Wiswall Hill Rd, Newfane, VT 05345
    • /23

      Est $503,669 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,200 Sq Ft

      2 Ives Rd, Wilmington, VT 05363

      2 Ives Rd, Wilmington, VT 05363
  • /19

    $399,000

    • 4 Beds
    • 2 Baths
    • 1,830 Sq Ft

    4850 Vermont Route 100, Wardsboro, VT 05355

    Dual charming updated cottages located conveniently between Mount Snow and Stratton with easy access off a paved public road for peace of mind and tremendous rentability. The current owners have lovingly updated these 2 cape style homes. One partially burned down and has been completely rebuilt and just completed. That larger home features an open concept kitchen and dining area, large great room

    Adam Palmiter Berkley & Veller Greenwood/Dover

    4850 Vermont Route 100, Wardsboro, VT 05355
  • /32

    $800,000 Sold Aug 08, 2025

    • 2,160 Sq Ft
    • $370/SF
    • 5 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1847

    3581 Houghtonville Rd, Grafton, VT 05146

    Located in a historic district at the edge of one of southern Vermont's most beautiful and vibrant villages, this property is a true Green Mountain Dream. The sellers purchased it as a vacation home, fell in love with it and moved there full time, renovating and expanding the home to blend classic Vermont charm with a modern lifestyle. Forced to return to their former location to maintain a

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    3581 Houghtonville Rd, Grafton, VT 05146
    • /31

      Est $360,553 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,963 Sq Ft

      962 Chapel Hill Rd, Whitingham, VT 05361

      962 Chapel Hill Rd, Whitingham, VT 05361
  • /15

    $485,000

    • 2 Beds
    • 2 Baths
    • 1,353 Sq Ft

    49 High Point Dr Unit A-14, Stratton, VT 05360

    49 High Point Drive, Crown Point A14, Stratton, VTIncredible opportunity to make Stratton Mountain Resort a place to call home. Nestled in the Green Mountains of Vermont, Crown Point offers easy condominium living close to the Stratton Mountain Resort Village. Shuttle service to the base area for skiing and riding. An outdoor pool and BBQ area is inviting for summer use. This one-level 2

    Andrew King Stratton Real Estate

    49 High Point Dr Unit A-14, Stratton, VT 05360
  • /25

    $296,000 Sold Aug 08, 2025

    • 860 Sq Ft
    • $344/SF
    • 3 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1986

    17 Mountain Village Unit 241, Dover, VT 05356

    One of a kind 2 bedroom, 2 bath condo at Snow Mountain Village at the base of the Mount Snow ski resort. This gorgeous vaulted and remodeled unit has all the style you would expect in a mountain retreat, with none of the headaches. Gorgeous exposed wood beams in the vaulted living room and kitchen, a stone hearth with wood burning fireplace, kitchen with ample storage and breakfast bar, separate

    Adam Palmiter Berkley & Veller Greenwood/Dover

    17 Mountain Village Unit 241, Dover, VT 05356
    • /31

      Est $102,704 Not Listed For Sale

      1124 Chapel Hill Rd, Whitingham, VT 05361

      1124 Chapel Hill Rd, Whitingham, VT 05361
  • /43

    $920,000

    • 5 Beds
    • 4 Baths
    • 2,238 Sq Ft

    8 E Birch Rd Unit 103, Stratton, VT 05360

    Rare 5BR/4BA Stratton Townhome | Ski-Back Access | Designer Furnished | Spacious, fully renovated 5-bedroom, 4-bath townhome at Stratton with ski-back access. Professionally designed and furnished by ACK Design, this move-in-ready home blends mountain charm with modern finishes. The main level features hardwood floors, a stunning floor-to-ceiling stone fireplace, and a granite kitchen

    Cheyanne Pugliese

    8 E Birch Rd Unit 103, Stratton, VT 05360
  • /28

    $290,000 Sold Aug 08, 2025

    • 1,344 Sq Ft
    • $216/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1975

    48 Hickory Hollow Rd, Vernon, VT 05354

    Charming Home in a Serene Setting, full of Potential!This super cute 3-bedroom, 1 3⁄4-bath home offers peaceful living with room to grow. Nestled in a tranquil setting with a fabulous yard, it features an additional office space and a partially finished walk-out basement—perfect for a family room, guest suite, or creative studio.Recent updates include an upgraded 100 amp electric panel, a

    Kerry Mulverhill

    48 Hickory Hollow Rd, Vernon, VT 05354
    • /26

      Est $242,748 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 700 Sq Ft

      2815 Burrington Hill Rd, Whitingham, VT 05361

      2815 Burrington Hill Rd, Whitingham, VT 05361
  • /50

    $435,000

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

    27 Country Ct, Wilmington, VT 05363

    Amazingly private cul-de-sac, the nicest location in Chimney Hill! 4 Bedroom 2 Baths, Livingroom with wood stove and a wall of windows to let the outdoors in! Hot Tub on multi-tiered deck. Beautiful wooded lot to explore, garden shed and garage. Live the Resort lifestyle on Chimney Hill's 1,200-Acre Resort Campus, with 550-Acres owned in common by the Homeowners Association. Numerous

    Janet Boyd Boyd Real Estate

    27 Country Ct, Wilmington, VT 05363
  • /2

    $1,100,000 Sold Aug 08, 2025

    • 1,234 Sq Ft
    • $891/SF
    • 33 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1991

    171 Pollard Rd, Grafton, VT 05146

    Nestled in the mountains of southern Vt, Grafton is one of New England's most quaint and picturesque villages. Grafton hosts shops, galleries, museums a cheese factory and a historic inn with upscale as well as casual dining.A long private drive leads to the house which overlooks several open acres, a pond, and over 1000 acres of green mountain state forestland offering the most

    Eric Scott Barrett & Valley Assoc. Inc

    171 Pollard Rd, Grafton, VT 05146
    • /12

      Est $258,475 Not Listed For Sale

      2027 Burrington Hill Rd, Whitingham, VT 05361

      2027 Burrington Hill Rd, Whitingham, VT 05361
  • /22

    $139,000

    • Land
    • 3.48 Acres
    • $39,943 per Acre

    Lot 5 Hope Rd, Newfane, VT 05345

    Buildable Acreage with permits in place on the West River! This is your chance to own a true waterfront lot with clearing, underground power already in place, a 4-bedroom septic permit, and ample river frontage to call your own. Build your dream home on this private cul-de-sac with only 4 other property owners ( currently 2 other homes). Step out your back door with your swimsuit on and your

    Jacki Murano Southern Vermont Realty Group

    Lot 5 Hope Rd, Newfane, VT 05345
  • /54

    $759,000 Sold Aug 08, 2025

    • 2,600 Sq Ft
    • $292/SF
    • 24 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1985

    544 Dalewood Rd, Jamaica, VT 05343

    Exceptional Vermont Retreat – Turnkey & Fully Furnished! Welcome to this beautifully maintained 5-bedroom, 5-bathroom contemporary home, offering a perfect mix of spacious comfort and cozy charm. Nestled in a peaceful neighborhood, and just 4 miles from SunBowl and minutes from the base lodge, this home features three en-suite bedrooms,two additional bedrooms, and a flexible extra room ideal for

    Rachel Febbie EXP Realty

    544 Dalewood Rd, Jamaica, VT 05343
    • /29

      Est $520,373 Not Listed For Sale

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

      960 Holbrook Rd, Jacksonville, VT 05342

      960 Holbrook Rd, Jacksonville, VT 05342
  • /33

    $397,777

    • 3 Beds
    • 2 Baths
    • 1,520 Sq Ft

    528 Vermont 121, Windham, VT 05155

    Nestled alongside a meandering stream, this perfectly private Cape-style home offers an idyllic setting with over 2 acres of lush land, perfect for play, gardening, or entertaining. Built in the late 80's this home features 3 bedrooms and 2 baths blending timeless appeal with modern conveniences. First floor bedroom and a 2 car garage attached with a practical mudroom offers easy living. 5 new

    Julie Citron RE/MAX Four Seasons

    528 Vermont 121, Windham, VT 05155
  • /29

    $526,000 Sold Aug 08, 2025

    • 1,620 Sq Ft
    • $325/SF
    • 36 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1965

    176 Pratt Bridge Rd, Jamaica, VT 05343

    Meticulously maintained and in pristine condition, this exceptional home has been lovingly cared for by the same family for over 50 years. Set back on a level, tree-lined lot on a quiet dead-end road, the home offers serenity and privacy while still being just a short drive to Stratton Mountain. Oversized windows throughout flood the interior with natural light, highlighting the soaring cathedral

    Carrie Mathews Winhall Real Estate

    176 Pratt Bridge Rd, Jamaica, VT 05343
    • /40

      Est $414,941 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,000 Sq Ft

      656 Allard Rd, Whitingham, VT 05361

      656 Allard Rd, Whitingham, VT 05361
  • /50

    $46,000

    • 2 Beds
    • 3 Baths
    • 1,080 Sq Ft

    357/359, Qtr 2 Grand Summit Way Unit 357/359, Qtr 2, Dover, VT 05356

    Ultimate Mountain Living at the Grand Summit Hotel. Experience a perfect blend of flexibility and mountain adventure with this deeded quartershare unit. Enjoy 13 weeks of vacation each year—one week every 28 days—on a rotating basis. Use it, rent it, or trade it for other destinations to suit your lifestyle.This spacious slope-side 2-unit lockout unit comfortably sleeps 8 and

    Donna Brown Skihome Realty

    357/359, Qtr 2 Grand Summit Way Unit 357/359, Qtr 2, Dover, VT 05356
  • /27

    $530,000 Sold Aug 08, 2025

    • 2,052 Sq Ft
    • $258/SF
    • 135 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1986

    69 Chapin Ln, Jamaica, VT 05343

    Welcome to Sugar Chateau- Nestled in the serene landscape of Southern Vermont, this enchanting 4-bedroom log home offers the perfect blend of rustic charm and contemporary comfort. Embrace the warmth and character with exposed beams and a welcoming atmosphere. Enjoy the convenience of modern amenities in a rustic setting, featuring a recently renovated kitchen and bathrooms. Custom new Anderson

    Tara van de Velde Four Seasons Sotheby's Int'l Realty

    69 Chapin Ln, Jamaica, VT 05343
    • /33

      Est $250,835 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 936 Sq Ft

      754 Allard Rd, Whitingham, VT 05361

      754 Allard Rd, Whitingham, VT 05361
  • /55

    $319,000

    • 3 Beds
    • 2 Baths
    • 2,910 Sq Ft

    597 Gates Pond Rd, Jacksonville, VT 05342

    Classic Greek Revival Expanded in True New England Farmhouse Fashion w/Studios, Timber-Frame Barn, Workshop, & Greenhouse on 3+ surveyed Acres. This 3-bed, 2-bath offers approximately 3,000 square feet of finished living space w/ flowing layout connecting a series of versatile spaces—all under one roof. From the original formal rooms of the farmhouse, step into a sequence of functional bonus

    Jacki Murano Southern Vermont Realty Group

    597 Gates Pond Rd, Jacksonville, VT 05342

Showing Results 281 - 320, Page 8 of 18

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