Windham County, VT Homes

• 

  

  

  /40

  Est $695,336 Not Listed For Sale

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

  143 Ray Hill Rd, Wilmington, VT 05363

  143 Ray Hill Rd, Wilmington, VT 05363
• 

  

  

  /9

  $185,000

  • Land
  • 8 Acres
  • $23,125 per Acre

  4441 Vermont 30, Jamaica, VT 05343

  Set amidst a peaceful woodland setting, this 8.0± acre parcel offers the perfect balance of seclusion and convenience—tucked away for privacy yet easily accessible year-round.. Currently being subdivided from a larger tract, this parcel presents a rare chance to shape your vision from the ground up.A five-bedroom Wastewater Permit has been approved, and a professional boundary survey is

  Helen Nault

  4441 Vermont 30, Jamaica, VT 05343
• 

  

  

  /16

  $310,000 Sold Oct 31, 2025

  • 1,248 Sq Ft
  • $248/SF
  • 236 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  12E Dover Green Loop Unit 12E, Dover, VT 05356

  Renovated townhome in the Dover Green community located just a short drive or shuttle ride south of Mount Snow. This spacious unit overlooks a pond and nice sunny exposure thanks to recent clearing, and has easy access to parking and the side yard. Inside is an open concept floor plan with vaulted great room, wood burning fireplace and brick hearth, a large eat in kitchen with new cabinets,

  Adam Palmiter Berkley & Veller Greenwood/Dover

  12E Dover Green Loop Unit 12E, Dover, VT 05356
• 

  

  

  /24

  Est $579,519 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,836 Sq Ft

  252 Ray Hill Rd, Wilmington, VT 05363

  252 Ray Hill Rd, Wilmington, VT 05363
• 

  

  

  /52

  $1,150,000

  • 8 Beds
  • 4 Baths
  • 4,828 Sq Ft

  5 Tannery Rd, West Dover, VT 05356

  Discover your getaway at Mount Snow in this beautifully renovated 8-bedroom estate, ideal for unforgettable family gatherings, cherished reunions, or inspiring work retreats. Set on nearly 4 serene acres at the foot of Mount Snow, you'll be surrounded by breathtaking mountain views and enjoy effortless access to the slopes just a short drive away. This magnificent home features a dedicated

  Michelle O'Neil Deerfield Valley Real Estate

  5 Tannery Rd, West Dover, VT 05356
• 

  

  /10

  $32,000 Sold Oct 31, 2025

  • Land
  • 1.06 Acres
  • $30,189 per Acre

  • 2 Days On Market

  298 Dover Hill Rd, Dover, VT 05356

  Affordable lot conveniently located on Dover Hill Road, with road frontage from Timberview Road, privately maintained gravel road offering nice privacy. North Branch Fire District sewer connection at the street, currently available at the cost of $4800+ per bedroom. Electric power and fiber internet available on the roadway, walk to Dover School, minutes to Mount Snow, dining and shopping.

  Monique White Deerfield Valley Real Estate

  298 Dover Hill Rd, Dover, VT 05356
• 

  

  /23

  Est $223,478 Not Listed For Sale

  • 8 Beds

  290 Ray Hill Rd, Wilmington, VT 05363

  290 Ray Hill Rd, Wilmington, VT 05363
• 

  

  /26

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  106 Silver Birch Unit 17H, Dover, VT 05356

  Bright 3-Bedroom End Unit at Timber Creek – Across from Mount Snow Ski Area.Welcome to your mountain getaway! This sunny 3-bedroom, 2-bath end unit in the desirable Timber Creek condominium community offers the perfect blend of comfort, convenience, and year-round recreation. Located directly across from Mount Snow and a short drive to the Hermitage Club, you'll enjoy unbeatable access to

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  106 Silver Birch Unit 17H, Dover, VT 05356
• 

  

  /47

  $555,000 Sold Oct 31, 2025

  • 1,937 Sq Ft
  • $287/SF
  • 35 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1850

  149 Dix Ln, Whitingham, VT 05361

  Tucked away on a quiet, town-maintained dead end road this Vermont country homestead offers the perfect blend of charm, privacy, and practicality. Set on 34+ acres, this property has woodlands, pasture and hay fields that have supported a working farm with livestock for the past 5 years. This property is well suited for those seeking a working homestead or a recreational retreat. The four-bedroom

  Sandy Reavill Real Broker LLC

  149 Dix Ln, Whitingham, VT 05361
• 

  

  /34

  Est $474,891 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,222 Sq Ft

  19 Strider Ln, Wilmington, VT 05363

  19 Strider Ln, Wilmington, VT 05363
• 

  

  /38

  $1,600,000

  • 5 Beds
  • 3.5 Baths
  • 3,040 Sq Ft

  4427 W Hill Rd S, Jamaica, VT 05343

  One-of-a-kind luxury lodge offering the comfort and amenities of a five-star retreat with the warmth and charm of a Vermont mountain home. The house provides all the space your friends and family could want—an expansive open layout perfect for gatherings, along with plenty of cozy, private spots for quiet moments. Enjoy movie nights in the 11-foot home theater, or relax in front of one of two

  Carrie Mathews Winhall Real Estate

  4427 W Hill Rd S, Jamaica, VT 05343
• 

  

  /19

  $475,000 Sold Oct 30, 2025

  • Land
  • 195 Acres
  • $2,436 per Acre

  • 1,058 Days On Market

  0 Route 9 Unit 4905132, Marlboro, VT 05344

  Large undeveloped forest land in southern Vermont is located in Marlboro, which is between the towns of Brattleboro and Wilmington. This forested parcel is made up of a maturing stock of Maples, Hemlock, White Pine, Beech, and Yellow Birch, with a large flat area that could be used for a building site. Good views can be had in any direction with some minor tree clearing, and old logging trails

  Thom Milke Fountains Land Inc.

  0 Route 9 Unit 4905132, Marlboro, VT 05344
• 

  

  /40

  Est $515,000 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

  $139,000

  • 4 Beds
  • 2 Baths
  • 1,910 Sq Ft

  2197 N Main St, Londonderry, VT 05148

  Charming 1860 Village Home with Character and Potential – Sold As Is.Step back in time with this 1860 village home offering space, character, and opportunity. Located right on the main road in a busy village setting, this 4-bedroom, 2-bath home provides a traditional layout with all bedrooms on the upper level and multiple gathering spaces on the first floor. Inside, you’ll find a

  Lee Brown Four Seasons Sotheby's Int'l Realty

  2197 N Main St, Londonderry, VT 05148
• 

  

  /20

  $361,589 Sold Oct 30, 2025

  • 1,152 Sq Ft
  • $314/SF
  • 85 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  43 Bear Lair Ln, Wilmington, VT 05363

  Nestled up against the tree line, this 3 bedroom 2 bath home offers a slice of privacy at the end of a dead-end road near the top of Chimney Hill. The current owner has opened the yard to let in more light and make it much more user friendly and functional. The driveway was expanded into a circular drive-through. Reduce your electricity costs with the new PV solar array on the roof that will

  Jim Bellville Bellville Realty

  43 Bear Lair Ln, Wilmington, VT 05363
• 

  

  /38

  Est $406,931 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,288 Sq Ft

  369 Route 9 W, Wilmington, VT 05363

  369 Route 9 W, Wilmington, VT 05363
• 

  

  /48

  $27,900

  • 1 Bed
  • 2 Baths
  • 941 Sq Ft

  230, Qtr 2 Grand Summit Way Unit 230, Qtr 2, Dover, VT 05356

  Experience the ultimate in flexibility and mountain living with this deeded quartershare at the Grand Summit Hotel. Enjoy 13 weeks of vacation annually—one week every 28 days—on a rotating basis. Use it, rent it, or trade it for other destinations! This very spacious valley-side unit is the closest unit to the owner's library and lounge, and comfortably sleeps 6. This is a 1-level, 1-bedroom unit

  Donna Brown Skihome Realty

  230, Qtr 2 Grand Summit Way Unit 230, Qtr 2, Dover, VT 05356
• 

  

  /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 $405,421 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
• 

  

  /14

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  8 Happy Haven Rd, Wilmington, VT 05363

  Conveniently located to village center, elementary school, lakes and trails. This riverfront home is waiting for a facelift! Three bedrooms, 2 bathrooms, living room, kitchen with a dining area with siders to a deck over looking the Deerfield River. Room downstairs for a hobby or craft room and a family room with a gas fireplace. Newer hot water tank and furnace. Room for gardens and a two car

  Janet Boyd Boyd Real Estate

  8 Happy Haven Rd, Wilmington, VT 05363
• 

  

  /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
• 

  

  /33

  Est $402,645 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,872 Sq Ft

  574 Higley Hill Rd, Wilmington, VT 05363

  574 Higley Hill Rd, Wilmington, VT 05363
• 

  

  /35

  $285,000

  • 3 Beds
  • 1.5 Baths
  • 3,096 Sq Ft

  11 Fornuto Rd, Wardsboro, VT 05355

  Opportunity awaits in this unique mixed-use property featuring a street-level restaurant space and a second-floor apartment. Located right in the heart of Wardsboro Village, once home to a local cafe, the main level still features brand-new commercial kitchen equipment ready for a fresh start. Convenient in-town location with good visibility, also within 10 minutes to Mt. Snow, 20 minutes to

  Jessica Samples BHG Masiello Keene

  11 Fornuto Rd, Wardsboro, VT 05355
• 

  

  /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
• 

  

  /35

  Est $414,708 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
• 

  

  /40

  $850,000

  • 3 Beds
  • 3 Baths
  • 2,994 Sq Ft

  260 Mansfield Ln, Londonderry, VT 05148

  Enjoy breathtaking views of Magic Mountain and the surrounding Green Mountains from the deck, living room, family room, and primary suite of this beautifully updated home. Whether you're seeking a primary residence or a vacation getaway, this property offers the perfect Vermont lifestyle. Large windows allow sunlight to flood the Great Room, highlighting a stunning floor-to-ceiling stone

  Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

  260 Mansfield Ln, Londonderry, VT 05148
• 

  

  /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
• 

  

  /38

  Est $491,655 Not Listed For Sale

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

  95 Davis Dr, Wilmington, VT 05363

  95 Davis Dr, Wilmington, VT 05363
• 

  

  /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
• 

  

  /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
• 

  

  /23

  Est $521,667 Not Listed For Sale

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

  2 Ives Rd, Wilmington, VT 05363

  2 Ives Rd, Wilmington, VT 05363
• 

  

  /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
• 

  

  /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
• 

  

  /31

  Est $343,214 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
• 

  

  /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
• 

  

  /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
• 

  

  /31

  Est $104,449 Not Listed For Sale

  1124 Chapel Hill Rd, Whitingham, VT 05361

  1124 Chapel Hill 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
• 

  

  /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
• 

  

  /26

  Est $235,533 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

Showing Results 281 - 320, Page 8 of 18