Windham County VT Homes for Sale

/9
$225,000
- Land
- 0.73 Acre
- $308,219 per Acre
5 Pinnacle View Rd, Dover, VT 05356

With breathtaking views of Mount Snow, this exceptional 0.73-acre parcel is the perfect setting for your dream mountain retreat. Located in the resort district, short-term rentals are permitted, making this a prime investment opportunity or an ideal family legacy home for generations to enjoy. Just off Route 100, a one-minute drive to the lifts at Mount Snow,an Epic Pass mountain, offering

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

5 Pinnacle View Rd, Dover, VT 05356
/45
$619,000
- 3 Beds
- 3 Baths
- 2,341 Sq Ft
49 High Point Dr Unit A122, Stratton, VT 05360

Crown Point, Stratton Vermont. Enjoy this two-level, three bedroom, three bath condo. This home has an upper and lower entry, both with plenty of storage for outdoor gear. The upper level opens into the kitchen, dining area, and living room with wood burning fireplace and a small deck. The primary ensuite bedroom, with a jacuzzi tub, is also on the upper level. The lower level has a second living

Mike England Michael England Real Estate

49 High Point Dr Unit A122, Stratton, VT 05360
/59
$399,000
- 5 Beds
- 3.5 Baths
- 2,800 Sq Ft
45 Dorr Fitch Rd, West Dover, VT 05356

Discover your Vermont mountain escape just 5 minutes from Mount Snow, where charm meets convenience and rental potential. This expanded chalet offers seasonal rental income, making it a smart investment for those looking to maximize returns. Step inside to find a cozy mudroom with natural stone walls, perfect for storing ski gear. The main level features an open floor plan with exposed beams, a

Richard Caplan Deerfield Valley Real Estate

45 Dorr Fitch Rd, West Dover, VT 05356
/27
$495,000
- 2 Beds
- 2 Baths
- 1,900 Sq Ft
106 Silver Birch Unit 17H, Dover, VT 05356

This 2 bedroom, plus bunkroom, end unit condo is located across the road from the Mt. Snow ski area. There is a shuttle to the mountain that will allow you to be free from driving and parking fees. Relax in your private hot tub after a day on the slopes or sit on this spacious deck an enjoy the view. A cozy wood-burning fireplace sets the mood for your apre' ski afternoon. On a rainy or

Regina Perrotto Skihome Realty

106 Silver Birch Unit 17H, Dover, VT 05356
/42
$674,000
- 3 Beds
- 3.5 Baths
- 1,537 Sq Ft
49 Greenspring Rd, Dover, VT 05356

Located in the desirable Greensprings neighborhood at Mount Snow Ski Resort, this spacious 3-bedroom, 4-bath townhome offers the perfect blend of mountain charm and modern comfort. The inviting interior features a soaring cathedral ceiling in the living room, anchored by a cozy wood-burning fireplace, creating the perfect apres-ski retreat. A second family room adds flexibility, ideal for

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

49 Greenspring Rd, Dover, VT 05356
/37
$119,000
- Land
- 10 Acres
- $11,667 per Acre
1105 S Hill Rd, Jamaica, VT 05343

Explore this exciting wooded 10.2+/- acre lot in the desirable town of Jamaica, VT. Jamaica has NO local zoning, making for simplified development, multiple cabins, camping and more. Plenty of road frontage on a year-round town plowed and maintained road. Best of all it is paved all the way to Wardsboro eliminating the difficulties of Vermont Mud Season. Utilities are located across from the

Curtis Trousdale Preferred Properties

1105 S Hill Rd, Jamaica, VT 05343
/6
$109,000
- Land
- 1.78 Acres
- $61,236 per Acre
0000 Wonder Ln Unit Lot 18, Jamaica, VT 05343

Prime 1.78-Acre Wooded Lot near Stratton Mountain Ski Resort and Golf Course---Nestled in a serene and private subdivision, this magnificent 1.78-acre wooded lot offers an unparalleled opportunity to build your dream home amidst Vermont's natural beauty. Located conveniently close to the renowned Stratton Mountain Ski Resort and Golf Course, this property promises year-round recreation and

Rachel Febbie EXP Realty

0000 Wonder Ln Unit Lot 18, Jamaica, VT 05343
/7
$99,000
- Land
- 2.06 Acres
- $48,058 per Acre
000 Wonder Ln Unit LOT 15, Jamaica, VT 05343

Prime 2.06-Acre Wooded Lot near Stratton Mountain Ski Resort and Golf Course---Nestled in a serene and private subdivision, this magnificent 2.08-acre wooded lot offers an unparalleled opportunity to build your dream home amidst Vermont's natural beauty. Located conveniently close to the renowned Stratton Mountain Ski Resort and Golf Course, this property promises year-round recreation and

Rachel Febbie EXP Realty

000 Wonder Ln Unit LOT 15, Jamaica, VT 05343
/55
$589,000
- 3 Beds
- 2.5 Baths
- 2,438 Sq Ft
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
/16
$319,000
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
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
/26
$650,000
- 5 Beds
- 2 Baths
- 1,530 Sq Ft
48 Upper Highlands, Dover, VT 05356

Unique opportunity to own an updated and woodsy chalet just up from the slopes of Mt Snow, yet also with direct snowmobile trail access. This 5 bedroom, 2 bath home has been tastefully renovated while maintaining the charm and character befitting a Vermont retreat ski home. The interior features an open concept living space with vaulted great room, wood burning fireplace, natural woodwork and

Adam Palmiter Berkley & Veller Greenwood/Dover

48 Upper Highlands, Dover, VT 05356
/21
$609,000
- 2 Beds
- 2 Baths
- 916 Sq Ft
771 Stratton Mountain Access Rd Unit 261, Stratton, VT 05360

771 Stratton Mountain Access Rd, Stratton, VT 05155Long Trail House is Stratton’s #1 location for owners who wish to combine personal use with an optional rental offset when not in residence. Walk to Village shops, restaurants and ski lifts. The floor plan for Long Trail House #261 is one of the largest of the 2 bedroom layouts. Master bedrooms has nice views of the Village Common.

Andrew King Stratton Real Estate

771 Stratton Mountain Access Rd Unit 261, Stratton, VT 05360
/60
$1,338,000
- 4 Beds
- 3.5 Baths
- 3,400 Sq Ft
1845 Hatch School Rd, Brattleboro, VT 05301

Welcome to our Contemporary Farmhouse with 100 private acres yet only 5 miles to Wilmington Center and 14 miles to Mount Snow Ski Resort. Harriman Reservoir is close for summer boating, water sports and picnics. Nestled in the heart of nature, the property offers numerous possibilities, including a well-appointed home, a working farm, various business opportunities and/or investment potential. As

Richard Caplan Deerfield Valley Real Estate

1845 Hatch School Rd, Brattleboro, VT 05301
/24
$749,000
- Land
- 2.57 Acres
- $291,440 per Acre
Lot 3 Old Mill Ln, Wilmington, VT 05363

Bring your own builder and discover an exceptional opportunity to own a 2.57 acre parcel of land located in an exclusive private neighborhood adjacent to the renowned private ski resort, The Hermitage Club in Wilmington, Vermont. This premium lot is the perfect canvas for creating your dream mountain retreat with custom homes to be crafted by your own builder or the Wadsworth Design Build. Enjoy

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

Lot 3 Old Mill Ln, Wilmington, VT 05363
/26
$749,000
- Land
- 1.22 Acres
- $613,934 per Acre
Lot 2 Old Mill Ln, Wilmington, VT 05363

Bring your own builder and discover an exceptional opportunity to own a 1.22-acre parcel of land located in an exclusive private neighborhood adjacent to the renowned private ski resort, The Hermitage Club in Wilmington, Vermont. This premium lot is the perfect canvas for creating your dream mountain retreat with custom homes to be crafted by your own builder or the Wadsworth Design Build. Enjoy

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

Lot 2 Old Mill Ln, Wilmington, VT 05363
/24
$774,000
- Land
- 3.60 Acres
- $215,000 per Acre
Lot 5 Old Mill Ln, Wilmington, VT 05363

Bring. your own builder and discover an exceptional opportunity to own a 3.6 acre parcel of land located in an exclusive private neighborhood adjacent to the renowned private ski resort, The Hermitage Club in Wilmington, Vermont. This premium lot is the perfect canvas for creating your dream mountain retreat with custom homes with your own builder or to be crafted by the Wadsworth Design Build..

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

Lot 5 Old Mill Ln, Wilmington, VT 05363
/37
$1,499,000
- 5 Beds
- 4.5 Baths
- 3,429 Sq Ft
26 Springhill Rd, Dover, VT 05301

This spectacular Post & Beam home is located just off the 13th hole of the Mount Snow Golf Course just minutes from the Mount Snow ski area. Nestled in a quiet community, with tremendous curb appeal, enjoy year round enjoyment thanks to the adjacent course, for obvious summer fun, but also snowshoeing and hiking in the winter. The interior of the home is about as good as it gets when looking for

Adam Palmiter Berkley & Veller Greenwood/Dover

26 Springhill Rd, Dover, VT 05301
/36
$998,500
- 4 Beds
- 3.5 Baths
- 2,070 Sq Ft
32 Shattarack Rd Unit B5, Stratton, VT 05360

Ski-in, ski-out Slopeside Townhouse! This meticulously remodeled offers everything you need for an exceptional mountain lifestyle. Inside, you’ll find your choice of two ensuite primary bedrooms, along with two additional spacious bedrooms, providing ample room and privacy for family and guests. Two bedrooms are enhanced with custom-built-ins, blending functionality with stylish design. The

Timothy Apps Four Seasons Sotheby's Int'l Realty

32 Shattarack Rd Unit B5, Stratton, VT 05360
/37
$725,000
- 3 Beds
- 3.5 Baths
- 2,400 Sq Ft
83B Greenspring, Dover, VT 05356

Imagine stepping into a pristine mountain townhome that feels like a warm embrace, complete with modern updates and breathtaking views of the surrounding peaks. The moment you enter, a spacious mudroom welcomes you, perfectly designed to accommodate all your outdoor gear and winter jackets. This three-bedroom plus den, 3.5-bath gem boasts a sun-drenched open floor plan where the living and dining

Sheila Joyce-Albano Skihome Realty

83B Greenspring, Dover, VT 05356
/28
$895,000
- 4 Beds
- 3 Baths
- 1,482 Sq Ft
19 Village Rd E, Wilmington, VT 05363

Here is a chance to own a home directly across the street from the private Hermitage Ski Club with easy access to the resort, snowmobile trails, the Mount Snow ski resort, nearby country villages for shopping and dining, and gorgeous area lakes. This lovely renovated chalet sits on a level with ample parking thanks to a circular driveway, winter exposure to Haystack Mountain Peak, a shed for

Adam Palmiter Berkley & Veller Greenwood/Dover

19 Village Rd E, Wilmington, VT 05363
/24
$570,000
- 4 Beds
- 3.5 Baths
- 1,616 Sq Ft
15 Mill Rd, Dover, VT 05356

What a location! MOOver shuttle service to the ski mountain yet a nice private home with a backyard and private deck, as well as views of the mountain. Direct snowmobile access and a drive out shed as well. Inside you are treated to a vaulted great room with wood burning brick fireplace and custom glass and metal screen, large newly replaced windows throughout with tremendous natural light, a

Adam Palmiter Berkley & Veller Greenwood/Dover

15 Mill Rd, Dover, VT 05356
/43
$2,000,000
- 6 Beds
- 4.5 Baths
- 3,750 Sq Ft
43 Upton Rd, Dover, VT 05356

The best of both worlds... High end luxury in this Post & Beam home on a private 35+ acre wooded lot with direct ski trail views of Mount Snow, yet just over a mile to the ski area. It's nearly impossible to find this kind of privacy so near mountain. This spectacular 6 bedroom, 4.5 bath Post & Beam home was built in 2007 and no expense was spared in the construction. Features include a high end

Adam Palmiter Berkley & Veller Greenwood/Dover

43 Upton Rd, Dover, VT 05356
/20
$215,000
- 3 Beds
- 1 Bath
- 636 Sq Ft
30 Water St, Jamaica, VT 05343

Discover the Acorn, a picturesque retreat nestled on the banks of the scenic West River in Jamaica, Vermont. This unique home, a beautifully converted sugar shack, offers an enchanting taste of rustic charm, perfect for those seeking a serene getaway. Ideal for nature lovers and outdoor enthusiasts, the Acorn sits close to the renowned ski resorts of Stratton Mountain and Mount Snow, providing a

Daire Gibney Barrett and Valley Associates Inc.

30 Water St, Jamaica, VT 05343
/42
$849,000
- 4 Beds
- 3.5 Baths
- 2,953 Sq Ft
37 Pleasant View Ln, Wilmington, VT 05363

4 bed, 3.5 bath, true log home w/excellent layout over 3 finished floors, 2 car garage, 5 acres, private pond, Mount Snow views, snowmobile trail access and all nicely tucked away on a dead end road. Just 2.2 miles to Rt 100 for easy access to downtown Wilmington shops and dining, Mount Snow Resort, the exclusive Hermitage Club, Harriman Reservoir and marina and multiple area golf courses. Even

Jacki Murano Southern Vermont Realty Group

37 Pleasant View Ln, Wilmington, VT 05363
/43
$495,000
- 3 Beds
- 2 Baths
- 1,943 Sq Ft
24 Antler Loop, West Dover, VT 05356

This charming 3-bedroom, 2-bath dutch colonial home sits atop a knoll, overlooking a picturesque half-acre pond in the front yard. Nestled on 2.06 acres in a tranquil neighborhood, the property offers an excellent floor plan for family living. The home features spacious bedrooms, a cozy brick fireplace in the living room with a cathedral ceiling, and a dining area with pine floors and pond views.

Jennifer Hovey-Densmore Deerfield Valley Real Estate

24 Antler Loop, West Dover, VT 05356
/25
$625,000
- 4 Beds
- 3 Baths
- 2,346 Sq Ft
5 Alpine Loop Rd, Dover, VT 05356

Tremendous opportunity to own an updated chalet at the base of the Mount Snow ski resort and Carinthia Freestyle Terrain Park. This charming home sits nestled on a quite loop just south of the mountain with direct walking and hiking trail access. The home features a large open floor plan with updated kitchen, stainless appliances, granite counters, and island, sunny living room with wood burning

Adam Palmiter Berkley & Veller Greenwood/Dover

5 Alpine Loop Rd, Dover, VT 05356
/34
$429,000
- 2 Beds
- 2 Baths
- 1,127 Sq Ft
27 Haymaker Ln Unit 9H, Wilmington, VT 05363

Cozy convenience on Haystack Mountain adjacent to The Hermitage Club and just a short drive to Mount Snow and downtown Wilmington. This 2 bedroom/2 bathroom unit has an open living space perfect for entertaining and highlighted by the fieldstone fireplace ambiance to warm you apres ski/hike or snowshoe. The unit is being offered furnished and ready to enjoy this season and year round with access

Cordelia Garofalo Deerfield Valley Real Estate

27 Haymaker Ln Unit 9H, Wilmington, VT 05363
/18
$250,000
- 5 Beds
- 1.5 Baths
- 1,504 Sq Ft
1614 Burbee Pond Rd, West Townshend, VT 05359

Great location for primary or vacation home. Near Burbee Pond in Windhame. 2.6 acres and possibly small commercial. 4 Plus bedrooms with one full bath and a half bath on main floor.Home is ready for your improvements.Close to ski resorts!

Bob Maisey Berkshire Hathaway HomeServices Stratton Home

1614 Burbee Pond Rd, West Townshend, VT 05359
/34
$749,000
- 4 Beds
- 3.5 Baths
- 2,230 Sq Ft
32 Circle View Dr, Dover, VT 05356

Gorgeous new construction home just completed and ready for immediate use this season. This lovely home sits just up from the Valley Trail in the heart of Dover with very easy access off a paved road, and near to the Mount Snow resort and golf course. The interior features gorgeous wood floors and exposed natural woodwork throughout, a custom kitchen with granite counters, stainless appliances,

Adam Palmiter Berkley & Veller Greenwood/Dover

32 Circle View Dr, Dover, VT 05356
/54
$2,490,000
- 7 Beds
- 7.5 Baths
- 6,518 Sq Ft
1324 Middle Rd, Brattleboro, VT 05301

Truly a rare and remarkable property. This custom home was lovingly designed and constructed in 2005 with a clear vision for bringing the Vermont scenery in, while maintaining the rustic charm befitting a country estate. The main house features gorgeous exposed timber frame construction throughout, natural wood flooring, paneling, and trim, extensive artisan stonework inside and out, including 3

Adam Palmiter Berkley & Veller Greenwood/Dover

1324 Middle Rd, Brattleboro, VT 05301
/9
$50,000
- 2 Beds
- 1 Bath
- 924 Sq Ft
189 Shady Pines Park, Westminster, VT 05158

1981 Skyline Homette mobile home in Shady Pines Park in Westminster. Very affordable approach to housing. Convenient to Rt. 91, Bellows Falls, Putney, Walpole, Brattleboro. Buyer will need to apply to Shady Park for approval. Property is being sold "as is".

John Hatton Berkley & Veller Greenwood Country

189 Shady Pines Park, Westminster, VT 05158
/57
$650,000 Open Sat 1PM - 3PM
- 3 Beds
- 2.5 Baths
- 2,720 Sq Ft
58 Buckboard Dr, Dover, VT 05356

Significant Price Improvement! This beautifully updated mountain retreat in the desirable Dover Hills is just 5 miles from Mount Snow and 30 minutes to Stratton. Thoughtful renovations have transformed the home with a brand-new kitchen featuring a quartz island, copper sink, high-end appliances, custom lighting, and a bar area with wine fridge and sink—perfect for apres-ski entertaining. The

Erica Reynolds Southern Vermont Realty Group

58 Buckboard Dr, Dover, VT 05356
/9
$50,000
- 2 Beds
- 1 Bath
- 924 Sq Ft
189 Shady Pines Park, Westminster, VT 05158

1981 Skyline Homette mobile home in Shady Pines Park in Westminster. Very affordable approach to housing. Convenient to Rt. 91, Bellows Falls, Putney, Walpole, Brattleboro. Buyer will need to apply to Shady Park for approval. Property is being sold "as is".

John Hatton Berkley & Veller Greenwood Country

189 Shady Pines Park, Westminster, VT 05158
/22
$289,000
- 3 Beds
- 2 Baths
- 1,512 Sq Ft
6738 Vermont Route 100, Wardsboro, VT 05355

This charming 1500 square foot manufactured home, located just over 3 miles from Mount Snow Ski Resort and a 15-minute drive to Stratton Mountain Resort, offers a perfect blend of comfort and convenience for mountain enthusiasts. 3 bedrooms and 2 bathrooms, this home provides ample space for family or guests. Inside, the open-plan living area is both cozy and spacious, featuring warm wood

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

6738 Vermont Route 100, Wardsboro, VT 05355
/26
$29,000
- 1 Bed
- 1 Bath
- 673 Sq Ft
215 Qtr.4, 89 Grand Summit Way, Dover, VT 05356

Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Benefits of Grand Summit ownership include the best ski in/out mountain location available. Use of the Grand Summit amenities all year round including valet parking, owners private lounge, private owners library, full service spa with saunas hot tubs and outdoor heated pool, private owners only ski/golf locker rooms for year

Kelly Agrillo Southern Vermont Realty Group

215 Qtr.4, 89 Grand Summit Way, Dover, VT 05356
/10
$250,000
- Land
- 23 Acres
- $10,823 per Acre
184 Dupre Dr, Guilford, VT 05301

Here's a large 23.10 +/- acre parcel that's mostly wooded but with a little bit of open field and possible short range local views. Conveniently located within a few minutes of town, here's an opportunity to enjoy country living while having access to modern amenities. There's a lot of potential for the right buyer! Please respect the privacy of the other houses on the road past this land.

A.J. Bellville Bellville Realty

184 Dupre Dr, Guilford, VT 05301
/36
$85,000
- Land
- 1.31 Acres
- $64,885 per Acre
100 Chimney Hill Rd, Wilmington, VT 05363

Merged Triple Lot on the Hill! Recent soil tests say this looks good for a 3-bedroom home! If you've been thinking of building your Dream home, this is a great spot. Located about 1/2 way up the Hill, right off the pavement. Walk to the Clubhouse, seasonal views, about 2,100' in elevation, facing SE. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season tennis,

Sigrid Pickering Chimney Hill Realty

100 Chimney Hill Rd, Wilmington, VT 05363
/38
$85,000
- Land
- 1.09 Acres
- $77,982 per Acre
95 Chimney Hill Rd, Wilmington, VT 05363

Triple Merged Lot on the Hill! Recent soil tests say this looks good for a 3-bedroom home! Right off the pavement about halfway up the Hill on the plateau. If you've been thinking of building your Dream home, this is a great spot. Walk to the Clubhouse, seasonal views, about 2,100' in elevation, facing SE. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season

Sigrid Pickering Chimney Hill Realty

95 Chimney Hill Rd, Wilmington, VT 05363
/60
$899,000
- 7,902 Sq Ft
3806 Vermont 11, Londonderry, VT 05148

This property features a 18-unit motel, that includes two apartment suites, alongside a spacious 3-bedroom, 2-bathroom home, making it a unique investment opportunity. Situated in the charming town of Londonderry, this property is perfectly positioned to attract visitors year-round with its proximity to two of Vermont's most popular ski destinations—Okemo Mountain Resort and Stratton Mountain

Flex Realty Group Flex Realty

3806 Vermont 11, Londonderry, VT 05148
/10
$350,000
- Land
- 7 Acres
- $49,435 per Acre
103 Schoolbus Depot Rd, Town of Rockingham, VT 05101

Located between Chester and Bellows Falls, just a mile from exit 6 off I-91, the opportunity for development awaits your ideas. Easy access, level parcel for either commercial ventures, gardens, or home. Land consists of two parcels separated by School Bus Depot Road totaling 7.08 acres. The island parcel gives excellent exposure to Route 103 for terrific signage. 103 is a high traffic corridor

Heidi Bernier Berkley & Veller Greenwood Country

103 Schoolbus Depot Rd, Town of Rockingham, VT 05101

Showing Results 321 - 360, Page 9 of 11

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.