Windham County VT Homes for Sale

/56
$475,000
- 3,954 Sq Ft
430 Hucklehill Rd, Vernon, VT 05354

Welcome home! This inviting property offers the perfect blend of privacy and comfort. Nestled in a peaceful wooded setting, surrounded by classic stone walls and a year-round stream, this home provides the Vermont lifestyle you’ve been dreaming of! Inside, the main level features gleaming hardwood floors with radiant floor heat and an open-concept layout with vaulted ceilings. The bright kitchen

Carol Slocum Keller Williams Realty Metro-Keene

430 Hucklehill Rd, Vernon, VT 05354
/16
$19,900
- Land
- 0.46 Acre
- $43,261 per Acre
00 Country Ct Unit 693, Wilmington, VT 05363

Attention skiers, golfers, hikers, boaters, VAST lovers, and more! Discover the perfect blend of a country setting, amenities, and convenience with this exceptional land opportunity! This nearly half-acre lot is admirably located within Chimney Hill’s 1,200-acre private resort community with access to a wide range of recreational amenities for both summer and winter enjoyment. Located at the

Casey Scott Southern Vermont Realty Group

00 Country Ct Unit 693, Wilmington, VT 05363
/36
$382,000
- 6 Beds
- 2.5 Baths
- 3,590 Sq Ft
88 Westminster St, Town of Rockingham, VT 05101

Welcome to this stately New Englander located in the heart of Bellows Falls, offering the perfect blend of historic character and generous living space. With over 4,500 square feet, this grand home provides 15 rooms, 6 bedrooms and the potential for 4 bathrooms across multiple levels, giving plenty of room for family, guests, home office space, or multi-generational living. Beautiful period

Jamie Watson BHG Masiello Keene

88 Westminster St, Town of Rockingham, VT 05101
/33
$390,000
- 3 Beds
- 1.5 Baths
- 2,208 Sq Ft
440 Stratton Arlington Rd, Stratton, VT 05360

Experience the charm of owning a chalet in Vermont’s sought-after Stratton area, ideally located between Stratton Mountain and Mount Snow for easy ski access. Recent road improvements ensure smooth travel year-round. Outdoor lovers will enjoy nearby trails for hiking, snowmobiling, and snowshoeing, making this an ideal retreat for both relaxation and adventure. The home features a finished

Mike England Michael England Real Estate

440 Stratton Arlington Rd, Stratton, VT 05360
/39
$312,000
- 2 Beds
- 2 Baths
- 860 Sq Ft
15 Mountain Village Unit 234, West Dover, VT 05356

Welcome to your mountain getaway! This 2-bedroom, 2-bath condo is perfectly situated at the base of Mount Snow. Enjoy your morning coffee or après-ski beverage on the private balcony while taking in the mountain air and breath taking views. Cozy up by the wood-burning fireplace, perfect for relaxing after a day on the mountain. Recent updates include new windows, slider doors, balcony, flooring

Jillian Wimmelman Deerfield Valley Real Estate

15 Mountain Village Unit 234, West Dover, VT 05356
/2
$199,000
- 2 Beds
- 2,710 Sq Ft
29 Stable Rd, Wilmington, VT 05363

The Stable Lodge was built in 1969-1970. Located near Haystack Ski Area and Golf Course and The Hermitage Club close to the Coldbrook. Built to sleep 32 People. Features 4 plus acres with ample parking. Building will need an extensive rehab. Not safe to go into the structure.

Mark Yule BHG Masiello Brattleboro

29 Stable Rd, Wilmington, VT 05363
/31
$735,000
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155

Nestled right on the slopes of Stratton Mountain Resort, this two bedroom two ensuite bathroom condominium offers true ski-in/ski-out convenience for your winter getaway. You'll find yourself just steps from the Villager chairlift, beginner ski area as well as a stone's throw to the shops and restaurants in the Stratton Village. An open-concept living/dinning/kitchen area that features a stone

Timothy Mich Doddridge Stratton Real Estate

778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155
/33
$415,000
- 1 Bed
- 1 Bath
- 650 Sq Ft
137 Pleasant Valley Rd, Brattleboro, VT 05301

Welcome to Pleasant Valley Road in beautiful West Brattleboro, Vermont! Lovingly created by the current owner, this incredibly efficient, timber frame home is custom built by a team of local craftsmen. A rare find, designed as an open concept with generous windows providing extraordinary light and connecting you to the outdoors. Insulated beyond expectation, 16 solar panels providing plentiful

Christine Lewis Brattleboro Area Realty

137 Pleasant Valley Rd, Brattleboro, VT 05301
/12
$36,999
- Land
- 2 Acres
- $18,500 per Acre
14 Brickyard Rd, Dover, VT 05341

Beautiful hillside parcel less than ten minutes from Mount Snow but outside the direct path of heavy tourist traffic. Brickyard Road is a winding packed-gravel road dotted sparsely with homes for full-time Dover residents, each with plenty of land and privacy. From the roadside the topography dips down about 5 feet, then quickly comes to a much more gradual slope which continues for approximately

David White OwnerEntry.com

14 Brickyard Rd, Dover, VT 05341
/44
$429,900
- 3 Beds
- 2 Baths
- 1,684 Sq Ft
1909 Davidson Hill Rd, Westminster, VT 05158

This charming Vermont country farmhouse offers peaceful privacy at the end of a quiet town road. Recently updated with quality materials and meticulous attention to detail, the home blends classic warmth with modern comfort. The open-concept main floor features a beautifully appointed kitchen ideal for family meals, flowing into the dining area and a cozy living room with a bay window and

Steve Schoppmeyer BHG Masiello Brattleboro

1909 Davidson Hill Rd, Westminster, VT 05158
/41
$399,000
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
25 Upper Handle Rd Unit A, Dover, VT 05356

Welcome to this inviting 3-bedroom plus loft, 2-bath Apple Hill condominium—perfectly located just minutes from Mount Snow. This spacious and well-maintained home offers a comfortable layout for a relaxing Vermont getaway. The updated kitchen and dining area feature a charming window seat, while the open-concept living room boasts another cozy window seat and a wood-burning fireplace for those

Jennifer Hovey-Densmore Deerfield Valley Real Estate

25 Upper Handle Rd Unit A, Dover, VT 05356
/45
$798,000
- 3 Beds
- 2 Baths
- 2,588 Sq Ft
619 Stratton Arlington Rd, West Wardsboro, VT 05360

Nestled between Stratton and Mount Snow and just minutes from Grout Pond, this timeless Vermont log home offers the perfect balance of rustic charm and modern comfort. Set on 7.90 beautifully landscaped acres with perennial gardens, a small pond, and mature fruit trees, the property captures the essence of mountain living.The main level features an open-concept layout with soaring beamed

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

619 Stratton Arlington Rd, West Wardsboro, VT 05360
/3
$500,000
- Land
- 5.05 Acres
- $99,010 per Acre
Lot 1 Mountain Ridge Estates, Wilmington, VT 05363

Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 5+ acres overlooking the 18th hole and mountains beyond for year

Adam Palmiter Berkley & Veller Greenwood/Dover

Lot 1 Mountain Ridge Estates, Wilmington, VT 05363
/3
$450,000
- Land
- 3.38 Acres
- $133,136 per Acre
Lot 4 Mountain Ridge Estates, Wilmington, VT 05363

Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 3.38+ acres overlooking the 18th tee box and mountains beyond for

Adam Palmiter Berkley & Veller Greenwood/Dover

Lot 4 Mountain Ridge Estates, Wilmington, VT 05363
/3
$500,000
- Land
- 1.1 Acres
- $454,545 per Acre
Lot 2 Mountain Ridge Estates, Wilmington, VT 05363

Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 1.1 acres overlooking the fairway of the 18th hole and mountains

Adam Palmiter Berkley & Veller Greenwood/Dover

Lot 2 Mountain Ridge Estates, Wilmington, VT 05363
/3
$500,000
- Land
- 1.82 Acres
- $274,725 per Acre
Lot 3 Mountain Ridge Estates, Wilmington, VT 05363

Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 1.82+ acres overlooking the 18th fairway and mountains beyond for

Adam Palmiter Berkley & Veller Greenwood/Dover

Lot 3 Mountain Ridge Estates, Wilmington, VT 05363
/54
$3,750,000
- 6 Beds
- 6.5 Baths
- 5,660 Sq Ft
168 Sunbowl Ridge Rd Unit 168 AB, Stratton, VT 05360

Experience true mountain luxury in this stunning six bedroom six bathroom slope side single family home, perfectly positioned for effortless access to world-class skiing and snowboarding at the Stratton Mountain Resort. Designed with comfort and style in mind, this residence combines refined alpine architecture with modern amenities including a gym, steam shower, pool table that doubles as table

Timothy Mich Doddridge Stratton Real Estate

168 Sunbowl Ridge Rd Unit 168 AB, Stratton, VT 05360
/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
/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
/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
/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
/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
/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
/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
/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. There is a wastewater permit for a 3 bedroom home in place. This expansive property offers a peaceful, wooded setting with ample privacy—ideal for recreation, a future homesite, or continued forest management. Currently enrolled in Vermont’s Current Use Program, the land offers significant tax

Carrie Mathews Winhall Real Estate

0 Townshend Dam Rd Unit 5066172, Wardsboro, VT 05355
/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
$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
/31
$445,000
- 2 Beds
- 2 Baths
- 1,230 Sq Ft
212 S Pine Banks Rd, Putney, VT 05346

Enchanting Putney Bungalow and separate studio 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

Karen Hoppe Berkley & Veller Greenwood Country

212 S Pine Banks Rd, Putney, VT 05346
/45
$599,000
- 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
/33
$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 spaces,

Keith Nowak Four Seasons Sotheby's Int'l Realty

7 Pine Tree Ln, Dover, VT 05356
/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
/34
$359,000
- 3 Beds
- 1.5 Baths
- 1,152 Sq Ft
410 Tallwood Cir, Londonderry, VT 05148

This cute Sherwood Forest house is ready for the next owners! Nicely renovated over the past several years, this 3 bedroom, 1 and a half bath chalet is located in the heart of Vermont ski country. In between Londonderry and Bromley, minutes from Manchester or Stratton and Magic ,this central location allows for access to all that makes Vermont special! Enjoy the open living area after a day of

Alison Cummings

Cummings & Co

(802) 392-0721

410 Tallwood Cir, Londonderry, VT 05148
/32
$949,000 New Construction
- 3 Beds
- 4.5 Baths
- 2,800 Sq Ft
49 Joan's Ridge Rd, Dover, VT 05356

Gorgeous new construction home just completed and ready for immediate use this season. This lovely home looks out to the ski trails at Mount Snow yet is in the heart of Dover with very easy access off a paved road. The interior features gorgeous natural light and exposed natural woodwork throughout, 3/4 inch solid red oak flooring, oversized windows, a bright living area with gas fireplace off

Adam Palmiter Berkley & Veller Greenwood/Dover

49 Joan's Ridge Rd, Dover, VT 05356
/54
$2,050,000
- 4 Beds
- 4.5 Baths
- 2,486 Sq Ft
97 N Brookwood Rd, Stratton, VT 05360

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 room with attached bathroom. Gorgeous great room with stone

Bob Maisey Berkshire Hathaway HomeServices Stratton Home

97 N Brookwood Rd, Stratton, VT 05360
/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
/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
/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
/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
/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
/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

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