Windham County, VT Homes

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  /42

  $574,900

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  555 Vermont 9, Wilmington, VT 05363

  Welcome to your dream home in the heart of Southern Vermont. This brand-new construction 3-bedroom, 2-bath residence seamlessly blends modern comfort with classic Vermont charm, perfect for year-round living or a weekend escape. Enjoy a spacious, open-concept layout filled with natural light, enhanced by high-quality Anderson windows and doors. The kitchen boasts brand new appliances, while the

  Flex Realty Group Flex Realty

  555 Vermont 9, Wilmington, VT 05363
• 

  

  

  /14

  $2,500 per month

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft
  • House for Rent

  4591 Vermont 30, Jamaica, VT 05343

  ITS NOT TOO LATE.. SNOW IS JUST STARTING TO FLY..This is a delightful Winter retreat...After a long fun day of skiing come home to this warm and cozy, meticulously maintained 4 bedroom home that is in great shape. Just 8 minutes from Stratton access Rd.Upstairs there are 2.5 bedrooms , kitchen, and living room with wood burning fireplace. Downstairs is another full bedroom and a 2nd kitchen,

  Wilkie Bushby TPW Real Estate

  4591 Vermont 30, Jamaica, VT 05343
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  /32

  $407,000 Sold Nov 21, 2025

  • 1,655 Sq Ft
  • $246/SF
  • 38 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1920

  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
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  /37

  Not Listed For Sale

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

  3 Valley View Unit CHB004, Wilmington, VT 05363

  3 Valley View Unit CHB004, Wilmington, VT 05363
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  /43

  $619,900

  • 3 Beds
  • 3.5 Baths
  • 2,250 Sq Ft

  883 Smead Rd, Wardsboro, VT 05355

  Enjoy Vermont living in this bright and inviting 3-bedroom, 4-bathroom home, ideally located 7 minutes from Mount Snow and just under 20 minutes from Stratton. The open-concept kitchen (completely renovated in 2021) and dining area are perfect for gatherings, with natural light enhancing the home’s warm and welcoming feel.A new heating system for efficient year-round comfort is complemented by a

  Samantha Decker Deerfield Valley Real Estate

  883 Smead Rd, Wardsboro, VT 05355
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  /32

  $4,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,080 Sq Ft
  • House for Rent

  194 Main St, Grafton, VT 05146

  VACATION RENTAL. In the center of Grafton Village find the refined Phebe Frost house. Beautifully maintained and thoughtfully decorated, spend some special time in Vermont! Lovely features include wood floors, double sided fireplace in living and dining, comfortable family room/den and stocked pantry. Delightful master suite on main floor and two additional bedrooms bookend a full bath upstairs.

  Jessica Landers Barrett and Valley Associates Inc.

  194 Main St, Grafton, VT 05146
• 

  

  /32

  $42,500 Sold Nov 21, 2025

  • 1,200 Sq Ft
  • $35/SF
  • 229 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1998

  269/71 Qtr.4,89 Grand Summit Way, Dover, VT 05356

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Benefits of Grand Summit ownership include the best ski in/out mountain location available. Use of the Grand Summit amenities all year round including valet parking, owners private lounge, private owners library, full service spa with sauna, hot tubs and outdoor heated pool, private owners only ski/golf locker rooms for

  Kelly Agrillo Southern Vermont Realty Group

  269/71 Qtr.4,89 Grand Summit Way, Dover, VT 05356
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  /40

  Est $647,197 Not Listed For Sale

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

  27 Haymaker Ln Unit 9A, Wilmington, VT 05363

  27 Haymaker Ln Unit 9A, Wilmington, VT 05363
• 

  

  /23

  $500,000

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft

  137 Pleasant Valley Rd, Brattleboro, VT 05301

  This is IT! If you are looking for an incredible small home...not tiny...but compact and just the right size, this is it. Timber framing at it's best gives you an open concept, live in every inch, light filled, high quality charming home. Nestled in a wildflower meadow, with plenty of room for a homestead garden, enough open sky for stargazers, big and flat enough for your own cross country ski

  Christine Lewis Brattleboro Area Realty

  137 Pleasant Valley Rd, Brattleboro, VT 05301
• 

  

  /25

  $295,000 Sold Nov 21, 2025

  • 1,944 Sq Ft
  • $152/SF
  • 5 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1880

  95 Forest St, Brattleboro, VT 05301

  This lovely home, offering 3 bedrooms and 3 baths, is located in a desirable neighborhood just minutes from downtown Brattleboro, close to dining, local shopping and community amenities. The interior has beautiful natural woodwork and flooring creating a warm and timeless atmosphere. The spacious common rooms on the first floor work well for a growing family or for entertaining family and

  Wilma Skovinski Berkley & Veller Greenwood Country

  95 Forest St, Brattleboro, VT 05301
• 

  

  /19

  Not Listed For Sale

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

  5 Spruce Haven Rd, Dover, VT 05356

  5 Spruce Haven Rd, Dover, VT 05356
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  /44

  $485,000

  • 3 Beds
  • 2 Baths
  • 1,751 Sq Ft

  2418 Vermont 11, Londonderry, VT 05148

  Discover this truly one-of-a-kind property in the heart of Londonderry, Vermont — a stunningly renovated former church that perfectly blends historic charm with modern elegance. This unique three-bedroom, two-bathroom home offers an expansive open-concept living space filled with natural light, showcasing soaring ceilings and gorgeous finishes throughout. The kitchen is a showstopper, featuring

  Noel Weeks Welcome Home Real Estate

  2418 Vermont 11, Londonderry, VT 05148
• 

  

  /23

  $249,000 Sold Nov 21, 2025

  • 1,008 Sq Ft
  • $247/SF
  • 109 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1965

  172 School House Rd, Putney, VT 05346

  Set on a level site, close to US Route 5 in Dummerston, this circa 1965 ranch is an excellent opportunity for a cozy, single-level home, equidistant between Brattleboro and Putney. Short walk to Dummerston School. Easy access to I-91. Easy driveway. Nice mix of sun and shade. Excellent gardening spot. High-speed internet. Single level living with 3 BR’s and a spacious full BA. Large eat-in

  Dan Normandeau Berkley & Veller Greenwood Country

  172 School House Rd, Putney, VT 05346
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  /11

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 612 Sq Ft

  3 Fox Meadow Ln Unit 3F, Dover, VT 05356

  3 Fox Meadow Ln Unit 3F, Dover, VT 05356
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  /44

  $599,000

  • 4 Beds
  • 4 Baths
  • 4,060 Sq Ft

  141 Piney Brook Way, Brattleboro, VT 05301

  Set on 12 acres of wooded privacy in desirable Marlboro, this spacious and versatile property offers comfort, flexibility, and stunning natural surroundings. The main home features 3 bedrooms, a large family room and first-floor laundry, offering plenty of room for a growing household, guests, or multi-generational living. Cozy up by the wood stove on chilly evenings, and enjoy the peace of mind

  Desiree Stango Berkley & Veller Greenwood Country

  141 Piney Brook Way, Brattleboro, VT 05301
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  /10

  $36,000 Sold Nov 20, 2025

  • Land
  • 1 Acre
  • $36,000 per Acre

  • 114 Days On Market

  00 Susan Lynn Ln, Wardsboro, VT 05355

  Escape to the beauty of Southern Vermont with this serene parcel located in the charming town of Wardsboro. Nestled in the Snow Mountain Farms development, this level 1 acre lot offers the perfect opportunity to build your dream home or vacation retreat. A short drive to Mount Snow and Stratton Mountain. Also within 30 minutes of Bromley Mountain & Magic Mountain. Outdoor enthusiasts will love

  Jessica Samples BHG Masiello Keene

  00 Susan Lynn Ln, Wardsboro, VT 05355
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  /2

  Not Listed For Sale

  • 1 Bed
  • 1 Bath

  5 Town Farm Rd, Town of Rockingham, VT 05101

  5 Town Farm Rd, Town of Rockingham, VT 05101
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  /31

  $485,000

  • 5 Beds
  • 5 Baths
  • 3,812 Sq Ft

  7 Pine Tree Ln, Dover, VT 05356

  Ready for its next chapter, this versatile property is in a great location near Mount Snow Skiing and Golf. If you are looking for a place to build some 'sweat equity' this one has amazing potential! Located on a cul de sac with only 4 other homes there is a nice sense of privacy while being close to restaurants and shopping. This unique offering is a rare opportunity with three separate

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  7 Pine Tree Ln, Dover, VT 05356
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  /39

  $395,000 Sold Nov 20, 2025

  • 2,715 Sq Ft
  • $145/SF
  • 10 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1895

  105 Chestnut St, Brattleboro, VT 05301

  A very special two unit! The main house is a spacious 3 bedroom, 1 bath with a primary bedroom and laundry on the first floor. The second unit is a desirable 1 bedroom, 1 bath. This authentic and updated Vermont home is situated on welcoming, dead-end street surrounded by woods on two sides creating a feeling of peacefulness and connection with nature. How fortunate to live in town but also have

  Kristen Ziter Taylor Brattleboro Area Realty

  105 Chestnut St, Brattleboro, VT 05301
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  /24

  Est $264,863 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,240 Sq Ft

  7 Hassey Bend Unit 16, Wilmington, VT 05363

  7 Hassey Bend Unit 16, Wilmington, VT 05363
• 

  

  /51

  $585,000

  • 3 Beds
  • 2 Baths
  • 1,814 Sq Ft

  1886 Winhall Hollow Rd, South Londonderry, VT 05155

  Exceptional property tucked amidst nature with views toward Magic. Whether you're a weekend warrior looking to enjoy everything the Green Mountains have to offer or looking for a year round residence with great schools, this property offers an optimal location- convenient to Stratton, Bromley and Magic Mountains as well as Burr and Burton Academy and Floodbrook School. Gourmet kitchen with gas

  Kim Morgan-Wohler Wohler Realty Group

  1886 Winhall Hollow Rd, South Londonderry, VT 05155
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  /47

  $476,000 Sold Nov 20, 2025

  • 2,372 Sq Ft
  • $201/SF
  • 29 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1976

  187 Hillwinds Rd, Brattleboro, VT 05301

  Welcome home! The four bedroom home with dedicated office space is located in one of the area’s most desirable communities. Just minutes from Brattleboro, it offers the perfect blend of convenience, comfort, and outdoor living, with walking trails right nearby. The bright, open layout is ideal for everyday living and entertaining, featuring a welcoming kitchen, dining, and living area. A private

  Claire Renaud Berkley & Veller Greenwood Country

  187 Hillwinds Rd, Brattleboro, VT 05301
• 

  

  /22

  Est $980,725 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 3,227 Sq Ft

  389 Cobble Hill Rd, Londonderry, VT 05148

  389 Cobble Hill Rd, Londonderry, VT 05148
• 

  

  /35

  $579,000

  • 4 Beds
  • 1 Bath
  • 1,560 Sq Ft

  104 Karen Day Rd, Halifax, VT 05342

  1860's Colonial/Farmhouse situated on nearly 37 acres of gorgeous land. This location, exposure, access and overall site characteristics is truly one of a kind. Ultimate privacy due to the town-maintained road (Karen Day Road) running from Larrabee Road all the way to the house and compound with no other houses along the road or in sight whatsoever. The land is remarkable with level open fields,

  Chris Long BHG Masiello Brattleboro

  104 Karen Day Rd, Halifax, VT 05342
• 

  

  /18

  $405,000 Sold Nov 20, 2025

  • 1,040 Sq Ft
  • $389/SF
  • 191 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1987

  6 Northbrook Village Way Unit 23, Dover, VT 05356

  This beautiful 2-bedroom, 2-bath end-unit condo in Seasons on Mount Snow offers the perfect combination of convenience, comfort, and mountain living. The open-concept floor plan with living, dining, and kitchen areas is perfect for family gatherings and entertaining. This mountain retreat, featuring a cozy floor-to-ceiling fieldstone fireplace, a slopeside location, and an abundance of natural

  Jessica Bentz Four Seasons Sotheby's Int'l Realty

  6 Northbrook Village Way Unit 23, Dover, VT 05356
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  /30

  Est $540,953 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  4 Robin Hill Rd, Townshend, VT 05353

  4 Robin Hill Rd, Townshend, VT 05353
• 

  

  /60

  $645,000

  • 3 Beds
  • 3.5 Baths
  • 2,472 Sq Ft

  38 Greenspring Rd, Dover, VT 05356

  Welcome to Greensprings one of Mount Snow’s most sought-after communities offering the perfect blend of mountain convenience and Vermont charm. This spacious 3 bedroom, 4 bath townhome features stunning mountain views and an inviting open-concept living area with vaulted wood ceilings, a dramatic wall of windows, and a floor-to-ceiling wood-burning fireplace.The main level is ideal for

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  38 Greenspring Rd, Dover, VT 05356
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  /31

  $333,333 Sold Nov 20, 2025

  • 1,659 Sq Ft
  • $201/SF
  • 75 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1968

  112 Robin Hill Rd, Townshend, VT 05353

  Tucked away on a quiet country lane, this lovingly maintained chalet-style home sits on a peaceful, wooded 1-acre lot—with an additional 1.3-acre adjoining parcel for extra privacy or future use. Inside, rich wood details create a warm, welcoming feel. The open living, kitchen, and dining area is perfect for everyday living or entertaining. Skylights in the primary bedroom and sunroom fill the

  Christina Dryden Berkshire Hathaway HomeServices Stratton Home

  112 Robin Hill Rd, Townshend, VT 05353
• 

  

  /6

  Est $91,851 Not Listed For Sale

  13 Edelweiss, Dover, VT 05356

  13 Edelweiss, Dover, VT 05356
• 

  

  /34

  $499,000

  • 4 Beds
  • 4 Baths
  • 3,152 Sq Ft

  977 Route 121, West Townshend, VT 05359

  Classic 1875 colonial home located on 5 acres in beautiful Windham VT. Home sits well off the road for privacy. Large first floor with kitchen, two living rooms, dining room and half bath with laundry. Second floor has 3 bedrooms and 2 full baths. Detached 2 car garage has a first floor bonus room with 1 bedroom 1 bathroom ADU on the second floor with separate utilities. Great rental

  Eric Scott Barrett & Valley Assoc. Inc

  977 Route 121, West Townshend, VT 05359
• 

  

  /50

  $345,000 Sold Nov 20, 2025

  • Land
  • 19 Acres
  • $18,158 per Acre

  • 5 Days On Market

  468 Park Laughton Rd, Dummerston, VT 05346

  Welcome to 468 Park Laughton Road in Dummerston, VT, a truly special opportunity to own 19 picturesque acres of classic Vermont countryside, complete with open fields, wooded privacy, and a peaceful brook running through the property. This beautiful parcel offers the perfect blend of natural beauty and functionality, featuring a rustic cabin ideal for weekend getaways, a future homestead, or a

  Jamie Watson BHG Masiello Keene

  468 Park Laughton Rd, Dummerston, VT 05346
• 

  

  /35

  Est $400,223 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 3,169 Sq Ft

  3796 Vt Route 30, Jamaica, VT 05343

  3796 Vt Route 30, Jamaica, VT 05343
• 

  

  /36

  $479,000

  • 4 Beds
  • 2.5 Baths
  • 1,887 Sq Ft

  230 Western Ave, Brattleboro, VT 05301

  This beautifully renovated in-town home blends character, comfort, and convenience. From the welcoming front porch to the shaded backyard and new deck, every space has been thoughtfully updated. The sunny kitchen offers granite countertops, stainless steel appliances, and a well-planned pantry, while the living room is anchored by a handsome Italian pellet stove; efficient, warm, and the perfect

  John Hatton Berkley & Veller Greenwood Country

  230 Western Ave, Brattleboro, VT 05301
• 

  

  /20

  $590,000 Sold Nov 19, 2025

  • 920 Sq Ft
  • $641/SF
  • 59 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2000

  771 Stratton Mountain Access Rd Unit 361, Stratton, VT 05360

  Experience the best of mountain living at Long Trail House. This light-filled 2-bedroom, 2-bath condo offers comfort, convenience, and an unbeatable location just steps from Stratton’s lifts, shops, and restaurants. The open-concept living area features a gas fireplace, perfect for cozy après-ski gatherings, and a well-equipped kitchen with a breakfast bar for casual dining. This corner unit has

  Christiane Carroccio TPW Real Estate

  771 Stratton Mountain Access Rd Unit 361, Stratton, VT 05360
• 

  

  /31

  Est $638,878 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,375 Sq Ft

  78 Middle Ridge Rd Unit 106, Stratton, VT 05155

  78 Middle Ridge Rd Unit 106, Stratton, VT 05155
• 

  

  /32

  $560,000

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft

  162 Buttonwood Dr, Brattleboro, VT 05301

  BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

  Dan Normandeau Berkley & Veller Greenwood Country

  162 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  /28

  $225,000 Sold Nov 19, 2025

  • 1,213 Sq Ft
  • $185/SF
  • 31 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1941

  5704 Coolidge Hwy, Guilford, VT 05301

  Tucked back off the road, equidistant between Brattleboro, Vermont and Bernardston, MA, this “cute-as-a-button,” chalet-influenced cape is an excellent opportunity for a cozy, 3-bedroom home or an Airbnb, on a 7.9-ac lot in beautiful Guilford, Vermont. Nice mix of sun and shade. Excellent gardening spot. High-speed internet available. Single-level living is possible, with a first-floor bedroom

  Dan Normandeau Berkley & Veller Greenwood Country

  5704 Coolidge Hwy, Guilford, VT 05301
• 

  

  /40

  Est $2,725,007 Not Listed For Sale

  • 6 Beds
  • 6.5 Baths
  • 7,088 Sq Ft

  83 Overlook Dr, Dover, VT 05356

  83 Overlook Dr, Dover, VT 05356
• 

  

  /32

  $585,000

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft

  161 Buttonwood Dr, Brattleboro, VT 05301

  BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

  Dan Normandeau Berkley & Veller Greenwood Country

  161 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  /59

  $2,700,000 Sold Nov 19, 2025

  • 5,413 Sq Ft
  • $499/SF
  • 58 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 2024

  1 Sundance Village Loop, Dover, VT 05356

  Welcome to your dream home, a striking 5-bedroom, 6-bathroom Mountain Modern home nestled within the exclusive Sundance Village! A unique opportunity awaits to own a stand-alone house, with direct access to the slopes at Mount Snow and the freshly-upgraded amenities of Seasons on Mount Snow. Imagine walking out your door, steps from the ski trail, coming back for a leisurely lunch, and at day's

  Patricia Fitzpatrick Skihome Realty

  1 Sundance Village Loop, Dover, VT 05356

Showing Results 81 - 120, Page 3 of 18