423

Windham County VT Homes for Sale

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  • /28

    $199,000

    • 2 Beds
    • 1 Bath
    • 844 Sq Ft

    8577 Vermont 30 Unit H, Jamaica, VT 05343

    Welcome to The Willows. Where convenience, comfort, and value come together in this well-appointed Condo featuring 2 bedrooms, 1 full bathroom with washer and dryer and updated appliances. Set privately back from Route 30, this thoughtfully maintained unit offers peaceful surroundings just two minutes from Stratton Access Road and within easy reach of Jamaica State Park and the West

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

    8577 Vermont 30 Unit H, Jamaica, VT 05343
  • /7

    $499,000

    • Land
    • 2 Acres
    • $249,500 per Acre

    70 Overlook Dr, Dover, VT 05356

    Stunning 2 acre building parcel at the prestigious Peaks at Mt Snow directly across from the ski resort. This lot affords tremendous privacy and exposure, but with amazing access and amenities including direct on call shuttle service from your door to the mountain, indoor pool, gym, clubhouse, and game courts. Paved road access, sewer, and water, means total peace of mind. Build your dream home

    Adam Palmiter Berkley & Veller Greenwood/Dover

    70 Overlook Dr, Dover, VT 05356
  • /20

    $330,000

    • 4 Beds
    • 3.5 Baths
    • 2,575 Sq Ft

    3730 Route 100, Wardsboro, VT 05355

    Property is being sold "as is where is" and does need some TLC. The house is set back off the road quite a bit for total privacy and there is a pond on the property. There is a one car garage, a full daylight basement, and a sun room.Sellers have given permission to encourage all offers. Property was originally listed for $450,000 but the sellers have reduced the price to $350,000. The tax

    Ginny Read Read Realty LTD

    3730 Route 100, Wardsboro, VT 05355
  • /14

    $1,750,000

    • 4 Beds
    • 3.5 Baths
    • 2,698 Sq Ft

    63 Sunbowl Ridge Rd Unit 63A, Stratton, VT 05360

    The absolute best location in one of Stratton's most desirable communities!This four bedroom, three and one half bath townhome is located directly on the ski trail. Immaculate interior. Bright sunny interior with eastern and southern exposure. One car garage, family room, back patio with new hot tub. Private pool and hot tubs located a short walk away. Shuttle service to Stratton base area

    John Sikes Stratton Real Estate

    63 Sunbowl Ridge Rd Unit 63A, Stratton, VT 05360
  • /27

    $539,000

    • 3 Beds
    • 2.5 Baths
    • 2,150 Sq Ft

    16A Snow Tree Ln Unit Cedars 1, Dover, VT 05356

    Rare Rare Rare! There are only 2 townhomes of this style at the desirable Snowtree development, and this particular 3 bedroom, 3 bath has been completely renovated. Walk out your private entry to the base area at Mount Snow via the convenient stream crossing bridge to access the magic carpet and tubing area, ideal for the ski season, but also any summer festivals. If someone doesn't ski they can

    Adam Palmiter Berkley & Veller Greenwood/Dover

    16A Snow Tree Ln Unit Cedars 1, Dover, VT 05356
  • /12

    $675,000

    • Land
    • 45 Acres
    • $15,000 per Acre

    000 Under the Mountain Rd, South Londonderry, VT 05155

    Travel down a quiet, tree-lined country road past historic homes, horse farms, and a large nature preserve to discover this magnificent property with views of Stratton and Bromley mountains in the distance. A large open field graced with wild flowers, apple trees and classic Vermont rock walls provides an ideal level home site, protected on three sides by extensive mature woods. The parcel has

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    000 Under the Mountain Rd, South Londonderry, VT 05155
  • /13

    $249,000

    • Land
    • 0.71 Acre
    • $350,704 per Acre

    24 Lower Highlands Rd, Dover, VT 05356

    Exceptional development opportunity just two minutes from the Mount Snow base area. This 0.71-acre parcel is fully approved for a four-unit residence with occupancy for 16. State wastewater and town construction permits are secured, and full architectural and structural engineering plans will convey.All approvals are valid for the next two years, allowing for immediate construction. With

    Jacki Murano Southern Vermont Realty Group

    24 Lower Highlands Rd, Dover, VT 05356
  • /12

    $995,000

    • 3 Beds
    • 3 Baths
    • 1,501 Sq Ft

    759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340

    Designed with the mountain enthusiast in mind, and located just a short walk from the Stratton Resort Village and ski slopes, this three bedroom three bath condominium offers quality and convenience. Private parking, pool, hot tub, sauna and shuttle to the slopes.

    John Sikes Stratton Real Estate

    759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340
  • /36

    $410,000

    • 7 Beds
    • 5 Baths
    • 2,978 Sq Ft

    343 Haystack Rd, Wilmington, VT 05363

    This spacious home is located near outdoor recreation spots like Mount Snow and Haystack Country Club. Tucked back on 3 acres with wooded surroundings offering privacy amongst the trees. The main house offers four bedrooms, four baths; including a large primary suite. The spacious basement has a kitchen, bath and living space with walkout access to the backyard. The three-car garage with a

    Jessica Citera Cummings & Co

    343 Haystack Rd, Wilmington, VT 05363
  • /58

    $515,000

    • 4 Beds
    • 2 Baths
    • 3,090 Sq Ft

    301 Maple St, Brattleboro, VT 05301

    Sweet! It is starting to get chilly, we remember the oversized salt water pool fun and the summer heat on tanned skin, coming again in the spring. The flowers and shrubs will sing again next season, but for now, we get to love the hardscape that comes to life catching flakes and creating breathtaking sculptures that glitter and change as we watch. It is the season for snuggling in, all toasty and

    Christine Lewis Brattleboro Area Realty

    301 Maple St, Brattleboro, VT 05301
  • /30

    $18,000

    • 1 Bath
    • 407 Sq Ft

    217 Qtr. 3,89 Grand Summit Way, Dover, VT 05356

    Slope side ski in/out with ski trail views and full hotel amenities! Gain that mountain resort life style at a truly affordable price. Use it, Rent it, Trade it! With 13 weeks of vacation a year round, benefits of Grand Summit ownership including the best ski in/out mountain location available-this is an opportunity to seriously upgrade your vacations. Use of the Grand Summit amenities all year

    Jacki Murano Southern Vermont Realty Group

    217 Qtr. 3,89 Grand Summit Way, Dover, VT 05356
  • /40

    $125,000

    • Land
    • 1.58 Acres
    • $79,114 per Acre

    408 Fox Mountain Rd, Wilmington, VT 05363

    Top of the Hill at the end of the Road! Triple building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sacon Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Club House. If you've been thinking of building your dream home, this is a great opportunity! Enjoy all

    Sigrid Pickering Chimney Hill Realty

    408 Fox Mountain Rd, Wilmington, VT 05363
  • /35

    $125,000

    • Land
    • 1.52 Acres
    • $82,237 per Acre

    406 Fox Mountain Rd, Wilmington, VT 05363

    Top of the Hill at the end of the Road! Triple building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sac on Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Clubhouse. If you've been thinking of building your dream home, this is a great opportunity!

    Sigrid Pickering Chimney Hill Realty

    406 Fox Mountain Rd, Wilmington, VT 05363
  • /25

    $769,000

    • 4 Beds
    • 4 Baths
    • 1,575 Sq Ft

    4L Trailside Village Way Unit H34, Dover, VT 05356

    Welcome to H34 Trailside Village Way, a rare opportunity to own a stunning 4-bedroom, 4-bath slopeside condo in the coveted Seasons on Mount Snow community. This impeccably maintained, never-rented home offers true ski-in/ski-out access—step out your door and onto the trail for unbeatable convenience all winter long. Inside, the open-concept living space is bathed in natural light, centered

    Jessica Bentz Four Seasons Sotheby's Int'l Realty

    4L Trailside Village Way Unit H34, Dover, VT 05356
  • /33

    $85,000

    • Land
    • 1.04 Acres
    • $81,731 per Acre

    402 Fox Mountain Rd, Wilmington, VT 05363

    Top of the Hill at the end of the Road! Double building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sac on Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Clubhouse. If you've been thinking of building your dream home, this is a great opportunity!

    Sigrid Pickering Chimney Hill Realty

    402 Fox Mountain Rd, Wilmington, VT 05363
  • /36

    $210,000

    • Land
    • 30.1 Acres
    • $6,977 per Acre

    184 Schoolhouse Rd, Jamaica, VT 05343

    Jamaica, Vermont's hidden gem! Experience this wonderful 30.1+/- acre forested parcel with views of the local mountains. The land gently slopes to the southeast, perfect for solar, but better yet, utility lines are located along much of the frontage! Bounded on two sides by classic stone walls, there is a woods road that travels through the property making exploration easy. Jamaica has NO local

    Curtis Trousdale

    184 Schoolhouse Rd, Jamaica, VT 05343
  • /12

    $50,000

    • Land
    • 3.6 Acres
    • $13,889 per Acre

    355 Bemis Hill Rd, Putney, VT 05346

    Sweet 3.6 acre lot ready for your imagination! Envision building your dream home bordered by picturesque stone walls and the soothing melody of a babbling brook. The land gently slopes up from the road to a level building site accessed from a rough driveway, you'll need to clear fallen trees, that has remnants of an old cabin. This is a lovely, quiet spot just half a mile off paved Westminster

    Rebecca Seymour Brattleboro Area Realty

    355 Bemis Hill Rd, Putney, VT 05346
  • /15

    $69,000

    • Land
    • 3.58 Acres
    • $19,274 per Acre

    Lot 4 Ghastly Job Way, Wilmington, VT 05363

    3.58 acres east of Wilmington village. This property is ready to build on, site work has commenced; tree clearing and partial driveway installed, fully engineered, survey, and Sate of Vermont Wastewater Permit for the construction of a three bedroom home. This parcel offers a great location, close to Lake Raponda for swimming, near Molly Stark State Park for hiking and minutes to Lake Whitingham

    Monique White Deerfield Valley Real Estate

    Lot 4 Ghastly Job Way, Wilmington, VT 05363
  • /47

    $999,000

    • 4 Beds
    • 2.5 Baths
    • 2,520 Sq Ft

    151 Holland Rd, Dover, VT 05341

    An outdoor enthusiast’s dream retreat! This breathtaking 92.6-acre Vermont sanctuary is a paradise for nature lovers, equestrians, and adventurers alike. The property features rambling stone walls, lush gardens, cherry trees, blueberry bushes, rolling pastures, woodlands, babbling brooks, a serene pond, and miles of scenic trails. The charming, open-concept, four-bedroom Cape includes a

    Patrice Schneider Southern Vermont Realty Group

    151 Holland Rd, Dover, VT 05341
  • /32

    $28,500

    • 1 Bed
    • 1 Bath
    • 671 Sq Ft

    302 Qtr.2, 89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Top floor one bedroom sleep 6 Valley side end unit. Kitchen, living room with a queen murphy bed and queen sleeper sofa and a king bed in the private bedroom with one full bath. Benefits of Grand Summit ownership include the best ski in/out mountain location available. Use of the Grand Summit amenities all year round

    Kelly Agrillo Southern Vermont Realty Group

    302 Qtr.2, 89 Grand Summit Way, Dover, VT 05356
  • /23

    $135,000

    • Land
    • 5.1 Acres
    • $26,471 per Acre

    1192 Haven Hill Rd, South Londonderry, VT 05155

    This 5+ acre building lot is ready for planning and designing your 5 bedroom dream-home, WW-2-3657 on a quiet country road, and Land Use Permit 2W0032-3. Just minutes to Gale Meadows and Stratton Mountain Resort, there are plenty of summer and winter outdoor adventures to embark on from hiking, kayaking, and fishing in the summer to skiing and snowshoeing in the winter. Only 25-minutes from

    Mike England Michael England Real Estate

    1192 Haven Hill Rd, South Londonderry, VT 05155
  • /20

    $995,000

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

    56 Shattarack Rd Unit D6, Stratton, VT 05360

    Rare opportunity to own an exceptional ski-out/ski-back Slopeside unit at Stratton. This newly renovated 3-bedroom plus loft, 3.5-bathroom townhome offers spacious accommodations in a prime location that is both private and highly convenient. The expanded kitchen features elegant stone countertops and stainless steel appliances, perfect for both everyday meals and entertaining. The wood-burning

    Kim Morgan-Wohler Wohler Realty Group

    56 Shattarack Rd Unit D6, Stratton, VT 05360
  • /30

    $1,250,000

    • Land
    • 108 Acres
    • $11,574 per Acre

    585 Pleasant Valley Rd, Jamaica, VT 05343

    108 Acres of Pristine Land For Sale – 2 Miles to Stratton Sun Bowl with Panoramic ViewsA rare opportunity to own ~108 acres of stunning land with sweeping views of Stratton’s Sun Bowl and Mount Snow. Just 2 miles to the Sun Bowl base and 15 minutes to Mount Snow, this Jamaica, VT property (on the Stratton line) offers unmatched privacy, no zoning restrictions, and incredible

    Britt Wohler

    585 Pleasant Valley Rd, Jamaica, VT 05343
  • /35

    $39,000

    • 2 Beds
    • 2 Baths
    • 914 Sq Ft

    311 Qtr.2, 89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Mountainside two bedroom sleep 6 unit with a covered balcony. Kitchen, living room with a queen sleeper sofa. The lofted bedroom and private bedroom both have king beds. Full bath with double sink vanity on the first floor and a 3/4 bath on the second floor. Benefits of Grand Summit ownership include the best ski in/out

    Kelly Agrillo Southern Vermont Realty Group

    311 Qtr.2, 89 Grand Summit Way, Dover, VT 05356
  • /28

    $499,000

    • 5 Beds
    • 3.5 Baths
    • 2,240 Sq Ft

    47 Ives Rd, Wilmington, VT 05363

    Unique spacious log home near the Hermitage Ski Club with easy access to the resort, direct snowmobile trail access, and tremendous privacy. Also just down the access road from the Mount Snow ski resort, nearby country village of Wilmington for shopping and dining, and gorgeous area lakes. This updated rustic retreat sits on a level lot with ample parking, winter exposure to the east, and a gear

    Adam Palmiter Berkley & Veller Greenwood/Dover

    47 Ives Rd, Wilmington, VT 05363
  • /26

    $89,499 New Construction

    • 2 Beds
    • 1 Bath
    • 746 Sq Ft

    204 Shady Pines, Westminster, VT 05158

    Welcome to 204 Shady Pines, Westminster VT 05158, where modern comfort meets affordability in Shady Pines MHP! This brand-new Polo model manufactured home offers 2 bedrooms, 1 bathroom, and 746 sq. ft. (14 x 56 ft.) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

    Kate Barry EXP Realty

    204 Shady Pines, Westminster, VT 05158
  • /48

    $799,000

    • 4 Beds
    • 4 Baths
    • 3,691 Sq Ft

    42 Airport Rd, Shaftsbury, VT 05262

    Welcome to this exquisite post and beam timber frame home, nestled in a prime location just moments from the Mount Snow Ski Resort and Mount Snow Golf Course. This remarkable 4-bedroom, 4-bathroom home blends rustic charm with modern luxury, offering an unparalleled mountain retreat perfect for both relaxation and adventure. As you step inside, you’ll be greeted by soaring ceilings and

    Mike Masters Four Seasons Sotheby's Int'l Realty

    42 Airport Rd, Shaftsbury, VT 05262
  • /38

    $38,000

    • 2 Beds
    • 2 Baths
    • 878 Sq Ft

    309 Qtr.3, 89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Mountainside two bedroom sleep 6 unit with a covered balcony. Kitchen, living room and queen sleeper sofa as well as a king bed in private bedroom on the first floor. Full bath with double sink vanity on the first floor. Lofted bedroom also has a king bed and a 3/4 bath . Benefits of Grand Summit ownership include

    Kelly Agrillo Southern Vermont Realty Group

    309 Qtr.3, 89 Grand Summit Way, Dover, VT 05356
  • /26

    $650,000

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

    10 Grouse Ln Unit 10A, Dover, VT 05356

    Stunning Post and Beam style townhome overlooking spectacular views of Mount Snow and Haystack ski trails with the sunsets in the west beyond. This private end unit features an amenity rich location thanks to direct VAST snowmobile trail access, hiking and biking trails in the summer, as well as easy access to the Mount Snow golf course which is directly through the adjacent woods, and nearby

    Adam Palmiter Berkley & Veller Greenwood/Dover

    10 Grouse Ln Unit 10A, Dover, VT 05356
  • /24

    $92,999 New Construction

    • 2 Beds
    • 2 Baths
    • 790 Sq Ft

    201 Shady Pines, Westminster, VT 05158

    Welcome to 201 Shady Pines, Westminster VT 05158, where modern comfort meets affordability in Shady Pines MHP! This brand-new Cortes model manufactured home offers 2 bedrooms, 2 bathrooms, and 790 sq. ft. (14 x 60 ft.) of thoughtfully designed living space.Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

    Kate Barry EXP Realty

    201 Shady Pines, Westminster, VT 05158
  • /32

    $98,999 New Construction

    • 2 Beds
    • 2 Baths
    • 825 Sq Ft

    160 Shady Pines, Westminster, VT 05158

    Welcome to 160 Shady Pines, Westminster VT 05158, where modern comfort meets affordability in Shady Pines MHP! This brand-new Lewis model manufactured home offers 2 bedrooms, 2 bathrooms, and 825 sq. ft. (14 x 56 ft.) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

    Kate Barry EXP Realty

    160 Shady Pines, Westminster, VT 05158
  • /46

    $1,100,000

    • 4 Beds
    • 3.5 Baths
    • 3,960 Sq Ft

    16 Springhill Rd, Dover, VT 05356

    Experience modern luxury in this stunning contemporary home, less than 10 minutes from Mount Snow and just 15 minutes from The Hermitage Club. This thoughtfully designed retreat offers both sophistication and comfort, with high-end finishes and exceptional craftsmanship throughout. You will be captivated by the soaring freestanding stone fireplace, which serves as the heart of the home, complete

    Patrice Schneider Southern Vermont Realty Group

    16 Springhill Rd, Dover, VT 05356
  • /51

    $879,900

    • 4 Beds
    • 3.5 Baths
    • 3,300 Sq Ft

    7 Yodeling Ln, West Dover, VT 05356

    Charming Log Home with Modern Comfort and Prime Location. This warm and inviting log home offers the perfect blend of rustic charm and modern style. Nestled on a level lot with ample parking, it features a large covered front porch and a spacious rear deck, ideal for enjoying the beautiful outdoors. Step inside to the main level, where you'll find a welcoming living room anchored by a stunning

    Rich Caplan Deerfield Valley Real Estate

    7 Yodeling Ln, West Dover, VT 05356
  • /60

    $4,495,500

    • 4 Beds
    • 5.5 Baths
    • 5,500 Sq Ft

    816 Black Bear Rd, Jamaica, VT 05343

    Set atop a scenic Vermont hillside, this five-bedroom custom-built home by The Wadsworth Design Build/Vermont Barns is a stunning example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural surroundings. Just a short drive from Stratton and Mount Snow ski resorts, it is the ultimate

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    816 Black Bear Rd, Jamaica, VT 05343
  • /5

    $35,000

    • Land
    • 1.2 Acres
    • $29,167 per Acre

    44 Antler Loop, Dover, VT 05356

    Come and join the nice quiet community of Dover Manor. This lot has road frontage on two sides of the property. There is a small wetland area on the Antler Loop side of the property, about 1/4 of the property. Private roads and close to elementary school, skiing and shopping. Elevation is at about 2000'.Town sewer is available.

    Regina Perrotto Skihome Realty

    44 Antler Loop, Dover, VT 05356
  • /13

    $50,000

    • Land
    • 2 Acres
    • $25,000 per Acre

    667 Hinkley Brook Rd, Grafton, VT 05146

    Nestled along the picturesque Hinkley Brook Road, this 2-acre parcel offers a rare opportunity to build your dream retreat in the charming and historic town of Grafton, Vermont. Just a short walk from the village center, you’ll enjoy the perfect blend of privacy and convenience, surrounded by the beauty of nature and classic New England charm. This peaceful lot boasts a gently wooded landscape

    Jamie Watson BHG Masiello Keene

    667 Hinkley Brook Rd, Grafton, VT 05146
  • /13

    $980,000

    • Land
    • 43.67 Acres
    • $22,441 per Acre

    Lot 10 & 16 Overlook Dr, Dover, VT 05356

    A rare opportunity to own the last remaining lots in the prestigious Peaks/Greenspring community! This home development site offers 44 acres of land including approximately 0.7 miles of private trails for hiking, ATV, snowmobiling and indirect connection to the VAST trails via Bluebrook Rd. The home site features full panoramic 180-degree mountain and woodland views to the north, east and south,

    Patricia Fitzpatrick Skihome Realty

    Lot 10 & 16 Overlook Dr, Dover, VT 05356
  • /38

    $35,000

    • 1 Bed
    • 2 Baths
    • 846 Sq Ft

    103/05 Qtr.1,89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This sleep 8 unit consists of two adjoining units; Studio unit (105) Queen murphy bed and queen sleeper sofa, kitchenette and full bathroom. Hotel unit (103) Two queen beds and full bathroom. Units are located the mountain side of the hotel just above from a beautiful brook and just down the hallway from the Spa, ski locker,

    Kelly Agrillo Southern Vermont Realty Group

    103/05 Qtr.1,89 Grand Summit Way, Dover, VT 05356
  • /13

    $150,000

    • Land
    • 4.68 Acres
    • $32,051 per Acre

    8559 Vt Route 30, Jamaica, VT 05343

    Waaaaait a minute! There’s buildable land just minutes from Stratton Mountain, and it’s already got septic not only approved, but basically installed?!?! I can just build my house on these 4.68 acres and enjoy all of the beauty and convenience of the area? And it's approved for 2 three bedroom houses!!! 2 miles to Stratton and 20 minutes to Manchester. I almost can’t believe this is

    TG Glazer Winhall Real Estate

    8559 Vt Route 30, Jamaica, VT 05343
  • /18

    $1,145,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    80 Banning Rd, Putney, VT 05346

    Rare offering on Putney Mountain! Spectacular house site with new foundation and great Southern exposure awaits your vision! Includes four bedroom septic system, and drilled well. Create your new home with the included framing lumber and your team of craftsmen. House is sited in a private location, yet is accessible to the town road via an easily maintained level driveway. Additional

    David White OwnerEntry.com

    80 Banning Rd, Putney, VT 05346

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