Windham County VT Homes for Sale

• 

  

  

  /4

  $120,000

  • Land
  • 5.17 Acres
  • $23,211 per Acre

  0 Anderson Rd Unit 5106592, Grafton, VT 05154

  This 5.17-acre wooded parcel in Grafton offers a great opportunity for your future Vermont home, with potential mountain views through selective clearing. The property has been surveyed, and the subdivision has received Town of Grafton approval.Engineering plans for a proposed well and wastewater system have been completed and filed with the State of Vermont. The state wastewater permit is

  Jessica Hunt Barrett & Valley Assoc. Inc

  0 Anderson Rd Unit 5106592, Grafton, VT 05154
• 

  

  

  /45

  $629,000

  • 5 Beds
  • 3 Baths
  • 2,430 Sq Ft

  13 Circle View Dr, Dover, VT 05356

  Perfectly positioned for enjoying all that the Mount Snow area has to offer, this beautifully updated home is located just 1.5 miles from Mount Snow Ski Resort and approximately 1 mile from the Mount Snow Golf Course.Step inside to a bright and inviting interior featuring vaulted ceilings, beautiful wood floors, mini-splits for year-round comfort, and a cozy woodstove the perfect place to

  Rich Caplan Deerfield Valley Real Estate

  13 Circle View Dr, Dover, VT 05356
• 

  

  

  /19

  $479,000

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

  162 Buttonwood Dr, Brattleboro, VT 05301

  It has all you wanted! Shiny wood floors to celebrate New England building, plenty of windows to capture every inch of light possible, granite tops on a multitude of cabinets, a step in shower but also a tub for long soaks or the little ones who visit....total one floor living, so rare locally, even no stairs to the direct entry garage. A service that plows, shovels and mows.....a playground for

  Christine Lewis Brattleboro Area Realty

  162 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  

  /47

  $449,000

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

  47 Upper Howes Way Unit A-23, Wilmington, VT 05363

  Priced to sell, on the Hill, End of the Road, Double Lot, built in 2024, Attached Garage, 3-bedroom 2 baths, Primary Suite with Ensuite Bath, Woodstove, Gas Cook Stove, Furnished, and Move-in Ready!Start enjoying all the amenities Chimney Hill offers within its 1,200-Acre Campus. Truly the most complete All-Season Resort in the Deerfield Valley with its exclusive members-only Clubhouse

  Sigrid Pickering Chimney Hill Realty

  47 Upper Howes Way Unit A-23, Wilmington, VT 05363
• 

  

  

  /17

  $439,000

  • 2 Beds
  • 2 Baths
  • 1,550 Sq Ft

  77 Buttonwood Dr, Brattleboro, VT 05301

  You've earned it.....the right to easy living.....have someone to do the heavy lifting...This community has become a much needed addition to the housing community. All are designed for the 55 and over who are looking for an easy way to settle in. Just think, the snowplowing, shoveling and salting are all taken care of, as well as the summer mowing and hedge trimming. One level living with no

  Christine Lewis Brattleboro Area Realty

  77 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  /27

  $289,000

  • 2 Beds
  • 1 Bath
  • 925 Sq Ft

  45 Kopkind Rd, Guilford, VT 05301

  Tucked into a peaceful, wooded setting on 2.1 acres in Guilford, just over the Massachusetts border, this cozy 2-bedroom, 1-bath home offers simple Vermont living with plenty of charm. Designed for convenient one-level living, the home features a back deck overlooking the yard surrounded by the quiet of the woods. Several recent improvements add to the home’s comfort and practicality, including a

  Neil Goldberg Brattleboro Area Realty

  45 Kopkind Rd, Guilford, VT 05301
• 

  

  /52

  $699,000

  • Land
  • 38 Acres
  • $18,395 per Acre

  1100 Houghtonville Rd, Grafton, VT 05146

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  1100 Houghtonville Rd, Grafton, VT 05146
• 

  

  /21

  $615,000

  • 4 Beds
  • 2.5 Baths
  • 2,212 Sq Ft

  354 Orchard St, Brattleboro, VT 05301

  You don't have to wear pearls to live here! This home oozes classic charm, memories of Thanksgivings and every holiday celebrated. The first step in has a welcoming wood stove for winter chill and glass french doors to fling open the first day of spring....Bring them home to the heart of the house with a dining room big enough for a feast...living room with a fireplace....warm hardwood floors, a

  Christine Lewis Brattleboro Area Realty

  354 Orchard St, Brattleboro, VT 05301
• 

  

  /52

  $299,000

  Open Sat 12PM - 2PM Coming Soon

  • 3,125 Sq Ft

  75 Moreland Ave, Brattleboro, VT 05301

  On offer is this tidy, three-unit multi-family home, located in a tranquil residential neighborhood on Moreland Avenue. Originally designed as a multi-family, the three units have identical floor plans with good layout flow. Each 2-bedroom unit has a large eat-in kitchen with pantry, a dining room with French doors opening to the living room and the bonus of a generous, three-season, enclosed

  Laura D'Angelo Berkley & Veller Greenwood Country

  75 Moreland Ave, Brattleboro, VT 05301
• 

  

  /40

  $535,000

  • 4 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  619 Main St, South Londonderry, VT 05155

  Set on 3 lovely acres in the heart of South Londonderry, this gracious four-bedroom, 2½-bath Victorian blends timeless character with thoughtful modern updates. Original floor-to-ceiling windows, soaring ceilings, hardwood floors, and classic Victorian details create a warm and inviting sense of history throughout the home.The newly renovated kitchen provides a fresh, functional gathering

  

  Alison Cummings

  Cummings & Co

  619 Main St, South Londonderry, VT 05155
• 

  

  /16

  $250,000

  • 2 Beds
  • 1 Bath
  • 988 Sq Ft

  8 Penny Ave, West Wardsboro, VT 05360

  Ranch style log cabin with partial loft situated on 2.67acres in Stratton, Vermont. Two bedrooms, one full bath, beautiful fieldstone fireplace with woodburning insert, hardwood floors, full concrete walk out basement with access from interior stairs as well. Covered front porch with nice stream on premise. Needs a buyer with a little vision. Owner will remove all personal property but may be

  Julie Lowe Lowe's Real Estate, LLC

  8 Penny Ave, West Wardsboro, VT 05360
• 

  

  /31

  $565,000

  • 5 Beds
  • 3 Baths
  • 2,768 Sq Ft

  77 Villager Loop, Dover, VT 05356

  This one won't last long! Beautifully maintained and updated chalet in the Dover Hills, just a short drive from the Mount Snow ski resort. The current owners have taken care to keep the original charm of this home while adding rustic features and recent updates to allow for turn key enjoyment. Off the side of a private paved loop, this home sits on a level parcel with ample parking, spacious

  Adam Palmiter Berkley & Veller Greenwood/Dover

  77 Villager Loop, Dover, VT 05356
• 

  

  /27

  $215,000

  • 2 Beds
  • 1 Bath
  • 964 Sq Ft

  301 Route 100 Unit 6, Dover, VT 05356

  Mount Snow Gem, Sweet, Affordable Ski Condo! Welcome to your Vermont getaway! This warm and inviting Mount Snow condo offers classic woodsy charm with tongue and groove walls, beamed ceilings, and the cozy character you’ve been looking for in a Vermont retreat. The open living and dining area features a woodstove, perfect for taking the chill off after a day on the slopes. A large slider opens to

  Monique White Deerfield Valley Real Estate

  301 Route 100 Unit 6, Dover, VT 05356
• 

  

  /23

  $255,000

  Open Sat 11AM - 1PM Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,683 Sq Ft

  159 Lower Bartonsville Rd, Chester, VT 05143

  Welcome to 159 Lower Bartonsville Road, a charming carriage house nestled along a scenic country farm road in Rockingham, Vermont, just moments from the picturesque restored Bartonsville covered bridge. This 3 bed, 1.5 bath property features authentic 1830s architecture and timeless rustic character, offering a solid structural foundation with much of its original detail preserved. Seamlessly

  Abby Gerbick Century 21 Highview Realty

  159 Lower Bartonsville Rd, Chester, VT 05143
• 

  

  /13

  $249,000

  • 1 Bed
  • 1 Bath
  • 480 Sq Ft

  1970 S Wardsboro Rd, Wardsboro, VT 05355

  Charming one bedroom cottage just outside the village of Wardsboro in Southern Vermont. This home away from home is being offered for sale for the first time by the original owners that built it. Up a private drive with easy access off a paved road sits this charming cottage, overlooking a river and short range mountain view across the way. There is a lovely open lawn space which is a small

  Adam Palmiter Berkley & Veller Greenwood/Dover

  1970 S Wardsboro Rd, Wardsboro, VT 05355
• 

  

  /21

  $349,000

  • 4 Beds
  • 1 Bath
  • 1,608 Sq Ft

  2068 S Wardsboro Rd, Wardsboro, VT 05355

  Charming cabin just outside the village of Wardsboro in Southern Vermont. This home away from home is being offered for sale for the first time by the original owners that built it. Up a private drive with easy access off a paved road sits this rustic retreat, overlooking a river and short range mountain view across the way. The home has a large open concept living space with the exposed log

  Adam Palmiter Berkley & Veller Greenwood/Dover

  2068 S Wardsboro Rd, Wardsboro, VT 05355
• 

  

  /25

  $287,900

  • 3 Beds
  • 2 Baths
  • 1,770 Sq Ft

  17 Willis Rd, Wilmington, VT 05363

  Enjoy the best of Southern Vermont from this spacious and inviting condo, offering a wonderful blend of comfort, convenience, and privacy. Ideally located just a short drive from Mount Snow and downtown Wilmington, this property is perfectly suited as a year-round retreat or four season vacation home. The open concept second floor offers an effortless flow between the kitchen, dining, and living

  Meghan Buckley Skihome Realty

  17 Willis Rd, Wilmington, VT 05363
• 

  

  /56

  $485,000

  • 3 Beds
  • 2.5 Baths
  • 2,392 Sq Ft

  46 Pearce Cir, Town of Rockingham, VT 05101

  Nestled on 8.75 private, mostly wooded acres with gorgeous mountain and river valley views, this turnkey 3 bedroom, 3 bathroom contemporary home has been extensively updated and thoughtfully improved. Step in from the front entryway into a generous mudroom with custom built-ins and tiled floors, leading directly into an expansive open-= concept living space with vaulted ceilings, radiant heat,

  Kate Barry EXP Realty

  46 Pearce Cir, Town of Rockingham, VT 05101
• 

  

  /20

  $250,000

  • 2 Beds
  • 1 Bath
  • 1,032 Sq Ft

  46 Rumrill Hill, Westminster, VT 05158

  Affordable! Tucked into a sweet spot, protected by a bit of woods, and fronted by both the paved public road and a smidge of unpaved road, there is easy access to everything you need! The owner has done an amazing job to bring this home a new look! The living room is large, leading to a porch and the back yard, and features a pellet stove. The kitchen is eat in with lots of counter and cupboard

  Christine Lewis Brattleboro Area Realty

  46 Rumrill Hill, Westminster, VT 05158
• 

  

  /23

  $325,000

  • 3 Beds
  • 2 Baths
  • 2,304 Sq Ft

  3156 Grafton Rd, Townshend, VT 05353

  Attractive Gambrel Style home with raised deck overlooking 1.5 acres offers private level backyard with babbling brook , apple trees and outbuilding. The first floor of this sweet primary home has a kitchen with custom cabinets, open dining area with access to the deck , full bathroom and large Livingroom . The second floor has 3 spacious bedrooms and another 3/4 bathroom . The walk -out basement

  Janet Lucier Barrett & Valley Assoc. Inc

  3156 Grafton Rd, Townshend, VT 05353
• 

  

  /14

  $275,000

  • 1,200 Sq Ft

  752 Butternut Rd, Guilford, VT 05301

  A perfect start! Well, power and driveway are all installed & septic design is available. The building constructed on slab, mostly finished surfaces, cathedral ceiling in the "living room". The interior is already sectioned into 4 rooms, waiting for kitchen and bath fixtures. Seller has plans for a one or 2 unit home build out. Sitting near the end of a quiet country road in no zoning Guilford,

  Christine Lewis Brattleboro Area Realty

  752 Butternut Rd, Guilford, VT 05301
• 

  

  /34

  $18,500

  • 1 Bath
  • 332 Sq Ft

  257, QTR 1, 89 Grand Summit Way, Dover, VT 05356

  Experience the ultimate ski-on, ski-off lifestyle with the convenience and luxury of resort hotel amenities at this slope-facing quartershare studio at the beautiful Grand Summit Hotel, located directly at the base of Mount Snow. This cozy, sleep-two studio offers a fully equipped kitchen, dining and living area, and a queen-size Murphy bed. Best of all, you can enjoy beautiful views of the ski

  Patricia Fitzpatrick Skihome Realty

  257, QTR 1, 89 Grand Summit Way, Dover, VT 05356
• 

  

  /31

  $15,900

  • 1 Bed
  • 1 Bath
  • 673 Sq Ft

  302 Qtr 2 Grand Summit Way, Dover, VT 05356

  Own where you play! This sun-filled, top-floor one-bedroom condo is located in a quieter area of the Grand Summit Resort Hotel, with a large window overlooking the Sundance ski trail. Just steps from the slopes, it offers convenient access to year-round resort amenities. A deeded quarter-share provides approximately 13 weeks of vacation ownership annually, with one week every 28 days on a

  Patricia Fitzpatrick Skihome Realty

  302 Qtr 2 Grand Summit Way, Dover, VT 05356
• 

  

  /20

  $24,900

  • 1 Bed
  • 2 Baths
  • 791 Sq Ft

  249/251, Qtr1 89 Grand Summit Way, Dover, VT 05356

  Own Where You Play in this Mountainview Quarter-Share! Experience the best of Mount Snow with this unique quarter-share ownership at the Grand Summit Resort Hotel. Designed to accommodate up to eight guests comfortably, this two-bath unit offers the flexibility to use, rent, or exchange your ownership for vacation stays worldwide. The main living area features an open-concept kitchen, dining, and

  Patricia Fitzpatrick Skihome Realty

  249/251, Qtr1 89 Grand Summit Way, Dover, VT 05356
• 

  

  /7

  $299,000

  • 4,077 Sq Ft

  30 Green St, Town of Rockingham, VT 05101

  This 4-unit multifamily located in the village of Bellows Falls is ready for a new owner, suitable for either an investor or a buyer who would like this to be their primary residence, as apt 3 is vacant and is currently being renovated. Pics of that unit to be added soon! Some recent improvements include a new furnace in 2024, updated wiring throughout the entire home, and a new water heater in

  Heather Gleim CENTURY 21 North East

  30 Green St, Town of Rockingham, VT 05101
• 

  

  /35

  $549,000

  • 4 Beds
  • 2.5 Baths
  • 2,359 Sq Ft

  116 Teacher Rd, Jamaica, VT 05343

  Set on 14.4 acres bordering the beautiful Green Mountain National Forest, this lovingly maintained 4-bedroom, 2.5-bath Vermont retreat offers the perfect combination of privacy, comfort, and year-round recreation. Currently operating as a successful Airbnb with repeat renters, the property is being offered fully equipped as a turn-key vacation rental opportunity or exceptional full-time

  Carrie Mathews Winhall Real Estate

  116 Teacher Rd, Jamaica, VT 05343
• 

  

  /44

  $349,000

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft

  34J Snow Tree Ln Unit Meadows J, Dover, VT 05356

  Welcome to this bright and spacious two bedroom, two-bathroom end unit condo in the desirable upper Snow Tree community. Ideally located near Mount Snow, this home offers beautiful winter mountain views and easy access to all the area has to offer.The inviting interior features a primary suite on the main floor, new windows, a cozy wood-burning fireplace, and a stunning cathedral ceiling

  Melissa Ellis Southern Vermont Realty Group

  34J Snow Tree Ln Unit Meadows J, Dover, VT 05356
• 

  

  /44

  $18,000

  • 1 Bed
  • 2 Baths
  • 840 Sq Ft

  236, Qtr 2 89 Grand Summit Way, Dover, VT 05356

  Trailside! Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Own this deeded quartershare property at Mount Snow Resort for 1 week every 28 days, on a rotating basis. This 1-of-a-kind, valley-view 1-bedroom, 2 full-bath unit has sleeping space for 4, an Open-Concept kitchen/dining room, and a living room with a queen sleeper sofa. There is a king-sized bed and a deck in the

  Donna Brown Skihome Realty

  236, Qtr 2 89 Grand Summit Way, Dover, VT 05356
• 

  

  /30

  $997,000

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 3,865 Sq Ft

  47 West Rd, Wilmington, VT 05363

  Be among the first to enjoy this brand-new mountain modern home in the sought-after Chimney Hill community, with an anticipated completion date of September 2026. Thoughtfully designed for both year-round living and weekend getaways, this 3-bedroom, 4-bath home offers a bright, open floor plan filled with natural light and clean, contemporary finishes.The main living area creates an inviting

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  47 West Rd, Wilmington, VT 05363
• 

  

  /36

  $469,000

  • 4 Beds
  • 2 Baths
  • 2,515 Sq Ft

  20 Wildwood Acres Rd, Newfane, VT 05345

  Lovely country home conveniently located just up from the Rock River in South Newfane, near the village, elementary school, and a short drive in to Brattleboro. This home is being offered for the first time in 40 years and has been lovingly maintained by the current owners. The 14+ acre parcel features a private setting, extensive stone work and landscaping, and an additional parcel which allows

  Adam Palmiter Berkley & Veller Greenwood/Dover

  20 Wildwood Acres Rd, Newfane, VT 05345
• 

  

  /28

  $725,000

  • 3 Beds
  • 2.5 Baths
  • 2,692 Sq Ft

  858 Sheldon Hill Rd, Wardsboro, VT 05355

  A perfect example of the ideal Vermont home. Beautiful natural woodwork abounds in this post and beam/log home hybrid built in 2005. Conveniently located on a corner lot with tremendous privacy and a spacious cul-de-sac driveway, is this perfect home with perennial gardens, a natural wood facade, stone chimney, stone walkway, large entertaining deck, patio with hot tub, and an exterior elevator

  Adam Palmiter Berkley & Veller Greenwood/Dover

  858 Sheldon Hill Rd, Wardsboro, VT 05355
• 

  

  /19

  $379,000

  • 1 Bed
  • 1 Bath
  • 680 Sq Ft

  2M Carinthia Rd, Dover, VT 05356

  One of a kind opportunity to be trailside at Mount Snow in a truly turn key completely updated unit. A rare chance to own a unit at Glen Run, at the base of Carinthia, with easy access to the earliest and latest trails open via the magic carpet, as well as to the newly built base lodge. This convenient one bedroom unit is on the ground floor affording easy access in and out via the rear slider,

  Adam Palmiter Berkley & Veller Greenwood/Dover

  2M Carinthia Rd, Dover, VT 05356
• 

  

  /41

  $849,000

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

  9A Windham Way, Dover, VT 05356

  This upgraded new style Greenspring townhome has direct views of Mount Snow and door to door shuttle service to and from the unit and the base area. A well updated 4+ bedroom, 4 bath unit with lots of bonus space, many recent updates and unique features. These include an open concept great room with vaulted ceiling, sunny exposure and sunset/ski trail views, wood burning fireplace unique against

  Adam Palmiter Berkley & Veller Greenwood/Dover

  9A Windham Way, Dover, VT 05356
• 

  

  /42

  $795,000

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft

  6694 Route 11, Londonderry, VT 05148

  Pride of ownership is evident throughout this exceptionally well cared for four-bedroom home, beautifully situated on more than four acres in desirable Londonderry. A long, welcoming driveway and a stately row of mature pines create a wonderful sense of arrival while providing year-round privacy. Offering an ideal blend of comfort, seclusion, and convenience, this inviting property is equally

  Carrie Mathews Winhall Real Estate

  6694 Route 11, Londonderry, VT 05148
• 

  

  /29

  $899,000

  • 4 Beds
  • 2.5 Baths
  • 3,314 Sq Ft

  28 Partridge Run Rd, Dover, VT 05356

  This stunning post and beam home is located just off the Mount Snow golf course, a short drive from the resort, with direct snowmobile trail access right from your home. This home sits on a level lot with nice privacy around the front deck and hot tub, for soaking after a day on the slopes. Inside is a tremendous great room with vaulted ceilings, great natural light, and exposed post and beam

  Adam Palmiter Berkley & Veller Greenwood/Dover

  28 Partridge Run Rd, Dover, VT 05356
• 

  

  /54

  $875,000

  • 3 Beds
  • 3.5 Baths
  • 3,916 Sq Ft

  30 Fieldstone Way, Londonderry, VT 05155

  Set in the peaceful Vermont countryside of Londonderry, this contemporary home offers the perfect blend of spacious living, natural beauty, and convenient access to some of Southern Vermont’s ski areas. Situated on 1.58 acres between Magic Mountain, Bromley, and Stratton, the property is ideally positioned for year-round recreation and relaxation.Built in 2004, the 4,094-square-foot home

  David Shehadi Josiah Allen Real Estate, Inc.

  30 Fieldstone Way, Londonderry, VT 05155
• 

  

  /20

  $23,500

  • 1 Bed
  • 2 Baths
  • 846 Sq Ft

  130/132, Qtr 3 89 Grand Summit Way, Dover, VT 05356

  This premier trailside, ski-in/ski-out lockout unit is located at the base of Mount Snow and offers exceptional versatility, comfortably sleeping up to eight people. The unit can be utilized as a full 1 bedroom, two-bath home or separated into individual suites to maximize rental potential. Unit 130 features a kitchenette and a comfortable living area with a sleep sofa, and a Murphy bed, sleep 4.

  Sheila Joyce-Albano Skihome Realty

  130/132, Qtr 3 89 Grand Summit Way, Dover, VT 05356
• 

  

  /26

  $290,000

  • 5 Beds
  • 1.5 Baths
  • 2,167 Sq Ft

  207 Elliot St, Brattleboro, VT 05301

  Offered to the public for the first time in nearly 60 years, this majestic Colonial-style home is located in one of Brattleboro’s oldest neighborhoods. The property showcases exquisite original details, including maple floors and fine hardwood trim throughout both levels. Many of the original plaster walls and ceilings have been professionally restored and await your personal color choices. The

  Bill Hickok Berkley & Veller Greenwood Country

  207 Elliot St, Brattleboro, VT 05301
• 

  

  /24

  $829,000

  • 4 Beds
  • 2 Baths
  • 1,638 Sq Ft

  12 Ober Tal Dr Unit C/23C/24, Stratton, VT 05360

  Unmatched Comfort and Convenience at Stratton's Ober Tal - trailside propertyDiscover the ideal ski retreat in this bright, spacious, one-of-a-kind double unit at Ober Tal, Building C. Next to the Tamarack ski lift, you’ll enjoy unbeatable access to the slopes and all the amenities in Stratton Village.Close enough to swing back for a quick lunch, this condo lets you make the most

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  12 Ober Tal Dr Unit C/23C/24, Stratton, VT 05360
• 

  

  /41

  $439,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  1137 Upper Dummerston Rd, Brattleboro, VT 05301

  Elegant and charming cape with an enchanting, exceptional garden that will impress even the seasoned green thumb. This magnificent home is solar equipped; the owner has had no electric bills for 3 years and the solar agreement may be transferred to the new buyer. Classic Vermont timeless style throughout features gorgeous archways, built-ins, and oak flooring. The kitchen is spacious with a

  Kristen Ziter Taylor Brattleboro Area Realty

  1137 Upper Dummerston Rd, Brattleboro, VT 05301

Showing Results 1 - 40, Page 1 of 12