Windham County, VT Homes

• 

  

  

  /9

  $295,000

  • Land
  • 54.8 Acres
  • $5,383 per Acre

  0 Townshend Dam Rd Unit 5066172, Wardsboro, VT 05355

  Explore the potential of this beautiful 53.8-acre parcel just 3.5 miles from the scenic Townshend Dam. This expansive property offers a peaceful, wooded setting with ample privacy—ideal for recreation, a future homesite, or continued forest management. Test pits have been completed, and results support the feasibility of a permitted septic system, paving the way for future development. Currently

  Carrie Mathews Winhall Real Estate

  0 Townshend Dam Rd Unit 5066172, Wardsboro, VT 05355
• 

  

  

  /56

  $3,750,000 Sold Oct 30, 2025

  • 6,900 Sq Ft
  • $543/SF
  • 16 Days On Market

  • 7 Beds
  • 7.5 Baths
  • Built 1988

  192 N Brookwood Rd, Stratton, VT 05360

  Perched at the top of Stratton Mountain Resort's most desired destination, this exceptional 7 Bedroom/7.5 Bath retreat is a prime alpine experience. Near the Wanderer ski trail w/ breathtaking views stretching across the Green Mountains, every detail of this property has been designed to offer privacy-capturing the essence of four-season luxury.With a rare blend of refined elegance & natural

  Kim Morgan-Wohler Wohler Realty Group

  192 N Brookwood Rd, Stratton, VT 05360
• 

  

  

  /29

  Est $516,845 Not Listed For Sale

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

  960 Holbrook Rd, Jacksonville, VT 05342

  960 Holbrook Rd, Jacksonville, VT 05342
• 

  

  

  /25

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,536 Sq Ft

  1091 Townshend Dam Rd, Townshend, VT 05353

  Tucked away on 3 private acres, this 3-bedroom home offers the perfect blend of charm, space, and potential. Just 3.5 miles from Townshend Dam and 5 miles to the Wardsboro General Store, it's ideally located—only 20 minutes to Mount Snow and 30 to Stratton. Inside, a dramatic wall of glass with two sets of French doors floods the living space with natural light and brings the outdoors in. The

  Carrie Mathews Winhall Real Estate

  1091 Townshend Dam Rd, Townshend, VT 05353
• 

  

  

  /55

  $624,000 Sold Oct 30, 2025

  • 2,438 Sq Ft
  • $256/SF
  • 234 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2000

  456 Poverty Row, Whitingham, VT 05361

  Lovely country setting on Poverty Row, a road name steeped in history, this builder’s home showcases quality craftsmanship and thoughtful design throughout. Set on 2.66 beautifully manicured acres with wild blueberry bushes and apple trees. Located on a paved public road, this property is less than five minutes from Lake Sadawga and Harriman Reservoir—perfect for boating, kayaking, and swimming.

  Erica Reynolds Southern Vermont Realty Group

  456 Poverty Row, Whitingham, VT 05361
• 

  

  /40

  Est $393,550 Not Listed For Sale

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

  656 Allard Rd, Whitingham, VT 05361

  656 Allard Rd, Whitingham, VT 05361
• 

  

  /55

  $375,000

  • 4 Beds
  • 2 Baths
  • 1,512 Sq Ft

  40 Ellis Brook Rd, West Dover, VT 05356

  Welcome to the beloved "Papa's Blue House," a cherished family home since its construction in 1968. Nestled in the desirable Dover Hills section of Dover, VT, this property offers the perfect blend of charm and potential. With good bones and a generous layout, it’s an ideal canvas for creating your dream home. Featuring a spacious open-concept living room, dining room, and kitchen, perfect for

  Donna Brown Skihome Realty

  40 Ellis Brook Rd, West Dover, VT 05356
• 

  

  /8

  $45,000 Sold Oct 30, 2025

  • Land
  • 0.5 Acre
  • $90,000 per Acre

  • 90 Days On Market

  00 Two Brook Dr, Wilmington, VT 05363

  Prime building opportunity in the heart of Vermont's four season playground! Flat lot w/enviable location near Haystack Golf Course & scenic Valley Trail. This parcel boasts not only a great location but also added convenience w/power, public water & sewer infrastructure nearby. Past waste water permits and design on file for building will need to be updated but are available for review. Vibrant

  Jacki Murano Southern Vermont Realty Group

  00 Two Brook Dr, Wilmington, VT 05363
• 

  

  /33

  Est $254,631 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft

  754 Allard Rd, Whitingham, VT 05361

  754 Allard Rd, Whitingham, VT 05361
• 

  

  /6

  $35,000

  • Land
  • 1.1 Acres
  • $31,818 per Acre

  9 Sun and Ski Rd, Wilmington, VT 05363

  Prime Land Lot – Minutes from Wilmington, Close to Mount Snow! Discover the perfect blend of seclusion and convenience with this exceptional land opportunity, ideally located just 8 minutes from Main Street Wilmington and only 20 minutes from the slopes of Mount Snow. Whether you're dreaming of a private mountain getaway, a cozy Airbnb investment, or building your forever home, this lot offers

  Flex Realty Group Flex Realty

  9 Sun and Ski Rd, Wilmington, VT 05363
• 

  

  /48

  $540,000 Sold Oct 29, 2025

  • 1,779 Sq Ft
  • $304/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2005

  16 Buckboard Dr, West Dover, VT 05356

  Award-winning, architect-designed home in the Hills of West Dover offers 3 bedrooms, 2 baths located on a beautifully sloped private and secluded 2-acre wooded lot. Originally built for the architect’s own family, the residence blends modern luxury with thoughtful design. The striking facade features painted cedar clapboard, pre-finished corrugated steel, large Anderson windows, and grade level &

  Lisa Mirando Deerfield Valley Real Estate

  16 Buckboard Dr, West Dover, VT 05356
• 

  

  /32

  Est $221,064 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 952 Sq Ft

  329 Deer Hill Rd, Whitingham, VT 05361

  329 Deer Hill Rd, Whitingham, VT 05361
• 

  

  /31

  $445,000

  • 2 Beds
  • 2 Baths
  • 1,230 Sq Ft

  212 S Pine Banks Rd, Putney, VT 05346

  Enchanting Putney Bungalow Retreat. Tucked away in a peaceful, sun-drenched meadow, this charming Putney bungalow offers the perfect blend of privacy, nature, and character. Surrounded by mature trees, stone walls, and abundant garden space, it’s a true hidden gem just minutes from the village center. Enjoy one-level living with a cozy first-floor bedroom and full bath and laundry—ideal for

  Karen Hoppe Berkley & Veller Greenwood Country

  212 S Pine Banks Rd, Putney, VT 05346
• 

  

  /40

  $80,000 Sold Oct 29, 2025

  • Land
  • 1.03 Acres
  • $77,670 per Acre

  • 167 Days On Market

  410 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 Club House. If you've been thinking of building your dream home, this is a great opportunity! Enjoy all

  Sigrid Pickering Chimney Hill Realty

  410 Fox Mountain Rd, Wilmington, VT 05363
• 

  

  /39

  Est $577,378 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 3,300 Sq Ft

  3358 Vt Route 100, Whitingham, VT 05361

  3358 Vt Route 100, Whitingham, VT 05361
• 

  

  /45

  $625,000

  • 4 Beds
  • 3 Baths
  • 2,775 Sq Ft

  4448 Route 100, Wardsboro, VT 05355

  This four-bedroom, three-bathroom home with additional office or bonus room space can be yours! Offering a spacious family room with fireplace, a cozy den off the garage entry. A formal dining room in addition to kitchen that allows for another sitting area with plenty of wall space to decorate. The location is set back off Route 100, so very minimal road noise yet the highway is always

  Julie Lowe Lowe's Real Estate, LLC

  4448 Route 100, Wardsboro, VT 05355
• 

  

  /20

  $525,000 Sold Oct 29, 2025

  • 1,824 Sq Ft
  • $288/SF
  • 35 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1975

  4 Sunnyside Rd, West Dover, VT 05356

  Location, location, location! This beautifully renovated ski chalet sits just a mile south of the Mount Snow ski resort with public shuttle service to and from the mountain. The home is far more private than you would expect from the small lot size, but that means less to maintain, and more downtime, not upkeep. Thanks to great proximity to amenities you also can easily get to nearby restaurants,

  Adam Palmiter Berkley & Veller Greenwood/Dover

  4 Sunnyside Rd, West Dover, VT 05356
• 

  

  /27

  Est $356,620 Not Listed For Sale

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

  540 Fowler Rd, Whitingham, VT 05361

  540 Fowler Rd, Whitingham, VT 05361
• 

  

  /54

  $2,050,000

  • 4 Beds
  • 4.5 Baths
  • 2,486 Sq Ft

  97 N Brookwood Rd, Stratton, VT 05360

  OPEN HOUSE SUNDAY OCTOBER 12TH 11:00AM-1:00PM!Welcome to your mountain chalet! 97 North Brookwood Road, one of the top most desirable locations on Stratton Mountain. Fully renovated and updated home, one of the eight original Austrian chalets on the mountain. Direct walk in and ski out to the Lower Wanderer trail. 4 bedroom in total with 3 en-suite bathrooms and 1 custom double bunk

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  97 N Brookwood Rd, Stratton, VT 05360
• 

  

  /46

  $480,000 Sold Oct 28, 2025

  • 2,092 Sq Ft
  • $229/SF
  • 29 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1975

  28 Dover Green Rd, Dover, VT 05356

  This 4-bedroom, 2-bath, 2,500 sq ft home on 1.26 acres in Dover, VT, offers the perfect blend of comfort, style, and location. Just 3 miles to Mount Snow and 7 miles to the Hermitage Club, it’s ideal for year-round living or a mountain getaway. The open kitchen, dining, and living areas create a welcoming, connected space, while a propane fireplace adds a cozy touch. The kitchen has been recently

  Kim Meeker Southern Vermont Realty Group

  28 Dover Green Rd, Dover, VT 05356
• 

  

  /29

  Est $596,131 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,732 Sq Ft

  55 Reed Hill Rd, Jacksonville, VT 05342

  55 Reed Hill Rd, Jacksonville, VT 05342
• 

  

  /12

  $325,000

  • Land
  • 3.42 Acres
  • $95,029 per Acre

  2366 Middletown Rd, Landgrove, VT 05148

  This property is within walking distance to the village of Londonderry and overlooks the town from its location approximately 500 paces up the hill on Middletown Road. The lot encompasses a hill that gives it privacy and security. Spring water flows to the base of the hill at one end of the propertyThe village commercial zoning gives the site options for multiple residential units (condos?),

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  2366 Middletown Rd, Landgrove, VT 05148
• 

  

  /36

  $420,500 Sold Oct 28, 2025

  • 1,537 Sq Ft
  • $274/SF
  • 512 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1986

  28 Greensprings Rd Unit GS U16, West Dover, VT 05356

  A rare gem hitting the market after 22 years. Its design spans two levels, 2-ensuite bedrooms & 2.5 baths, providing ample space for comfort & convenience. Sold furnished, it's primed for immediate enjoyment. Nestled within the Greenspring community, this unit offers easy access to the rec center, pool, & tennis courts, just a short stroll away. The private back deck affords stunning mountain

  Donald Koelsch Deerfield Valley Real Estate

  28 Greensprings Rd Unit GS U16, West Dover, VT 05356
• 

  

  /35

  Est $298,630 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,626 Sq Ft

  159 Reed Hill Rd, Jacksonville, VT 05342

  159 Reed Hill Rd, Jacksonville, VT 05342
• 

  

  /39

  $1,150,000

  • 4 Beds
  • 4.5 Baths
  • 5,000 Sq Ft

  3 Shannon Ridge Rd, Dover, VT 05356

  3 Shannon Ridge Road, West Dover, VT Private Mountain Retreat Between Mount Snow and The Hermitage Club Experience the perfect fusion of luxury, privacy, and adventure in this beautifully renovated 4,950 sq ft home set on 1.62 acres of tranquil Vermont countryside. Ideally positioned between Mount Snow and the private Hermitage Club, this home offers a rare opportunity for refined mountain living

  Derek Greene Derek Greene

  3 Shannon Ridge Rd, Dover, VT 05356
• 

  

  /36

  $515,000 Sold Oct 28, 2025

  • 2,139 Sq Ft
  • $241/SF
  • 60 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2022

  4A Junior's Way, Dover, VT 05356

  This newly constructed 3-bedroom, 3-bath townhome, built in 2022, offers modern mountain living just minutes from the Mount Snow ski resort. With a convenient location, the slopes can easily be accessed via a short walk to the free MOOver Bus. The home boasts three levels of living, an open concept design with a fireplace, spacious living and dining areas, a beautiful updated kitchen, and a

  Prema Fitzpatrick Skihome Realty

  4A Junior's Way, Dover, VT 05356
• 

  

  /40

  Est $542,060 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,296 Sq Ft

  371 Butler Brook Rd, Jacksonville, VT 05342

  371 Butler Brook Rd, Jacksonville, VT 05342
• 

  

  /41

  $1,495,000

  • 4 Beds
  • 3.5 Baths
  • 4,153 Sq Ft

  487 Vermont Route 100, Londonderry, VT 05148

  Set on nine acres, this inviting three bedroom brick home offers a rare blend of comfort, space, and rural charm. The main level features a large primary bedroom, with a beautiful full bathroom and walk in closet. Each room on the main level you'll find bright and comfortable living spaces and a beautiful sunroom that overlooks the surrounding fields. Upstairs, two spacious bedrooms share a

  Jamie Wylie Stratton Real Estate

  487 Vermont Route 100, Londonderry, VT 05148
• 

  

  /30

  $447,000 Sold Oct 27, 2025

  • 2,648 Sq Ft
  • $169/SF
  • 68 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1989

  60 Woodland Rd, Vernon, VT 05354

  This lovely New England Style colonial home, located in an agrarian community of southern Vermont just north of the Massachusetts border, is not to be missed! The spacious colonial exudes charm with a covered front porch, bay windows, and a perennial garden. The Fox Hill Association provides for peaceful living and has community septic and town maintained roads. This well cared for home offers a

  Arlene Palmiter Berkley & Veller Greenwood/Dover

  60 Woodland Rd, Vernon, VT 05354
• 

  

  /17

  Est $172,046 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 826 Sq Ft

  813 Gates Pond Rd, Jacksonville, VT 05342

  813 Gates Pond Rd, Jacksonville, VT 05342
• 

  

  /60

  $798,000

  • 3 Beds
  • 3 Baths
  • 2,757 Sq Ft

  1909 Pine Banks Rd, Putney, VT 05346

  Sweetwood Farm circa 1894, this beautifully maintained extended Cape encompasses 60 serene acres of rolling meadows, shaded woodlands, and a peaceful, cascading brook. If you've been dreaming of a home that offers a convenient location, charm, and connection to the land, this is it. Inside, you'll find warm wide-pine floors, handcrafted cherry cabinets, and cozy living spaces filled with

  Heidi Bernier Berkley & Veller Greenwood Country

  1909 Pine Banks Rd, Putney, VT 05346
• 

  

  /58

  $740,000 Sold Oct 27, 2025

  • 3,276 Sq Ft
  • $226/SF
  • 10 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2006

  360 Valley View Rd, West Dover, VT 05356

  Tucked in the woods just minutes from Mount Snow and The Hermitage Club, this 3-bedroom, 3-bath home blends privacy, comfort, and convenience. Set on a beautifully landscaped lot, the property offers expansive decks surrounded by mature plantings, creating the perfect backdrop for outdoor entertaining or quiet relaxation. Just steps away, Cooper Hill rewards you with breathtaking sunrises, while

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  360 Valley View Rd, West Dover, VT 05356
• 

  

  /23

  Est $274,243 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,224 Sq Ft

  123 Birdville Rd, Whitingham, VT 05361

  123 Birdville Rd, Whitingham, VT 05361
• 

  

  /15

  $530,000

  • Land
  • 30 Acres
  • $17,667 per Acre

  00 W Hill Rd S, Jamaica, VT 05343

  Discover 30+ acres of coveted Vermont land, offering breathtaking views, open fields, stonewalls, large pond & established driveway. This unique property features an expansive, man-made pond that’s clean, deep, and perfect for paddling, swimming, or even stocking with fish. Excellent southern exposure for solar energy possibilities ,power line access adjacent to the property, this land offers

  Jacki Murano Southern Vermont Realty Group

  00 W Hill Rd S, Jamaica, VT 05343
• 

  

  /17

  $397,500 Sold Oct 27, 2025

  • 820 Sq Ft
  • $485/SF
  • 26 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1983

  10 Ober Tal Dr Unit B12, Stratton, VT 05360

  Own at Ober Tal and enjoy Slopeside Living in the heart of Stratton Mountain. Just steps from the Trails and Tamarack Chair Lift, getting on the slopes couldn’t be easier. This updated one-bedroom, one-bath home features an airy open living and dining area with a classic wood-burning fireplace as its centerpiece. A ground-level location offers the bonus of a private patio, while the generous

  Helen Nault

  10 Ober Tal Dr Unit B12, Stratton, VT 05360
• 

  

  /40

  Est $359,737 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,248 Sq Ft

  4840 Vt Route 100, Whitingham, VT 05361

  4840 Vt Route 100, Whitingham, VT 05361
• 

  

  /32

  $299,000

  • 3 Beds
  • 2.5 Baths
  • 2,338 Sq Ft

  4106 Vt Route 30, Jamaica, VT 05343

  Built in 1840, this charming home has long been a part of Jamaica’s rich history. Thoughtfully updated for modern living, it features a brand-new septic system, a renovated kitchen with granite countertops, and spacious rooms filled with natural light. Perfectly located just a short walk to town and Jamaica State Park, and only 10 miles from Stratton’s lifts, this property offers the ideal blend

  Carrie Mathews Winhall Real Estate

  4106 Vt Route 30, Jamaica, VT 05343
• 

  

  /33

  $340,000 Sold Oct 24, 2025

  • 1,152 Sq Ft
  • $295/SF
  • 8 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1965

  134 Vt Route 30, Newfane, VT 05345

  Riverfront Retreat – Tucked away on 4.2 acres along the river, this very well-maintained three-bedroom, two-bath home offers a rare blend of comfort and natural beauty. Surrounded by trees and wildlife, the property provides a private retreat where you can enjoy the sights and sounds of nature right from your doorstep. Inside, the bright and inviting living space features large windows that frame

  Claire Renaud Berkley & Veller Greenwood Country

  134 Vt Route 30, Newfane, VT 05345
• 

  

  /38

  Est $740,212 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 3,332 Sq Ft

  1793 Faulkner Rd, Whitingham, VT 05361

  1793 Faulkner Rd, Whitingham, VT 05361
• 

  

  /53

  $1,470,000

  • 5 Beds
  • 4.5 Baths
  • 5,160 Sq Ft

  224 Cobble Ridge Rd, Londonderry, VT 05148

  Perched on scenic Cobble Ridge, this custom five-bedroom, four-and-a-half-bath retreat embodies balance, light, and renewal in the heart of Southern Vermont. Set on seven private, fenced acres framed by stone walls and dual gated entries, the property enjoys southwest exposure with soft, filtered ridgeline views that evolve beautifully through the seasons. Inside, a brick fireplace anchors the

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  224 Cobble Ridge Rd, Londonderry, VT 05148

Showing Results 321 - 360, Page 9 of 18