Windham County VT Homes for Sale

/27
$449,000
- 3 Beds
- 1.5 Baths
- 1,140 Sq Ft
39 Parsons Rd, Jacksonville, VT 05342

Beautiful updated woodsy chalet located just outside the town of Wilmington on 4.5 acres with total privacy. This home was an old sugar house, and is conveniently accessible just off a quiet dirt road. The lot has two babbling brooks, gorgeous exposed stone features, a spacious driveway, wood shed, and a separate parking area with a recently built two car, two story 24x28 garage barn. Inside the

Adam Palmiter Berkley & Veller Greenwood/Dover

39 Parsons Rd, Jacksonville, VT 05342
/12
$50,000
- Land
- 3.60 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
/21
$39,900
- 1 Bed
- 2 Baths
- 778 Sq Ft
201/03 Qt.3, 89 Grand Summit Way, Dover, VT 05356

Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? One bedroom lockout sleep 8 unit. Studio side (201) has a Kitchen, living room with a queen murphy bed and queen sleeper sofa. Unit (203) has two queen beds. Both units have a full bathroom and balcony's. A great way to enjoy the mountain resort lifestyle at an affordable price.Benefits of Grand Summit ownership include the

Kelly Agrillo Southern Vermont Realty Group

201/03 Qt.3, 89 Grand Summit Way, Dover, VT 05356
/9
$74,900
- Land
- 3.58 Acres
- $20,922 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
/44
$575,000
- 6 Beds
- 4 Baths
- 3,000 Sq Ft
22 Chestnut St, Brattleboro, VT 05301

Rare residential investment opportunity in the heart of Brattleboro! This offering includes 4 of 5 units in a charming condo development just minutes from downtown, the hospital, shopping, and I-91. Unit 5 has been sold. Live in one unit and rent the other 3 or sell them! The property features a large shared yard, off-street parking, and strong rental potential. The owner currently receives

Erica Reynolds Southern Vermont Realty Group

22 Chestnut St, Brattleboro, VT 05301
/27
$399,000
- 4 Beds
- 1.5 Baths
- 1,404 Sq Ft
696 S Wardsboro Rd, Wardsboro, VT 05355

PRICED TO SELL! Fabulous Southern Vermont Estate nestled between Mount Snow and Stratton Ski Areas! You'll have Wardsboro Brook in you back yard & Grout Pond down the street as well as the hiking trails VAST, Appalachian Trail (AT) and Long Trails. Plenty of Back Country outdoor Experiences available all year round! They say location is everything this property has everything and more. The

Kimberly Dubois Matson KW Realty

696 S Wardsboro Rd, Wardsboro, VT 05355
/14
$196,000
- Land
- 32 Acres
- $6,125 per Acre
100 Stagecoach Rd, Town of Rockingham, VT 05156

A very cool cabin on a beautiful, ultimate private 32 +/- acres. The cabin is 400 square feet with a spacious loft. The deck faces east to very pretty CT River Valley Views. There is no water or power, only an outhouse and woodstove for Vermont getaways, a hunting camp or snowmobile extremists. Seller has invested roughly $30,000 into improving Stagecoach Rd. Property is enrolled in the current

Kristen Ziter Taylor Brattleboro Area Realty

100 Stagecoach Rd, Town of Rockingham, VT 05156
/5
$315,000
- 3 Beds
- 2.5 Baths
- 2,014 Sq Ft
412 Western Ave, Brattleboro, VT 05301

The cutest house on the block! Only 1 house from the famous deli for eats, right near the entrance to I 91, both north and south for travel or work and 2 minutes away from Memorial Park with all it offers....skating, ball games, pools, sliding, skiing. Plus it has a great back yard, 2 levels of decks and a front porch to add to the package. This 1860's Mansard is so sweet, filled with character

Christine Lewis Brattleboro Area Realty

412 Western Ave, Brattleboro, VT 05301
/47
$1,100,000
- 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
/18
$399,000
- 3 Beds
- 3.5 Baths
- 1,400 Sq Ft
29 Maple Hill Loop, Dover, VT 05356

A rare opportunity for a Spruce Haven townhome accessible to the Dover village, Valley Trail, Mount Snow Ski Resort and Golf Course, the Hermitage private ski club, and MOOver shuttle service just down the street. This spacious and fully renovated end unit townhome has 3 bedrooms with en suite baths, a main floor guest half bath, a large open concept living space with hearth and efficient gas

Adam Palmiter Berkley & Veller Greenwood/Dover

29 Maple Hill Loop, Dover, VT 05356
/13
$349,000
- Land
- 33 Acres
- $10,624 per Acre
0 Smith Rd, Marlboro, VT 05363

Nestled at the end of a quiet, quintessential roadway, this stunning parcel of land offers the perfect blend of privacy and natural beauty. Surrounded by mature maples, stone walls, and towering pines, this property provides a serene, wooded environment while offering the potential for breathtaking views with some clearing. Tucked away at the end of a peaceful, dead-end road, this property offers

Richard Caplan Deerfield Valley Real Estate

0 Smith Rd, Marlboro, VT 05363
/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 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
/23
$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 Wohler Realty Group

585 Pleasant Valley Rd, Jamaica, VT 05343
/35
$40,000
- 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
/24
$439,000
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
18 Dover Green Rd, Dover, VT 05356

This charming 3-bedroom, 2-bath home is tucked away in a peaceful wooded setting, offering the perfect retreat with a cozy, well-maintained ambiance. The spacious living room features a gas fireplace and a Rinnai heater, ensuring comfort throughout the seasons. Adjacent to the living area, the open kitchen and dining space make for a perfect gathering spot. A versatile den with a nearby 3/4 bath

Richard Caplan Deerfield Valley Real Estate

18 Dover Green Rd, Dover, VT 05356
/39
$4,300,000
- 6 Beds
- 5 Baths
- 4,715 Sq Ft
141 W Ridge Rd, Stratton, VT 05360

Experience the charm of this renovated, ski-in/ski-out 6-bedroom, 5-bathroom retreat, perched as the second-highest home on Stratton’s iconic Lower Wanderer Ski Trail. Immerse yourself in the rustic elegance of this space, where expansive windows invite breathtaking outdoor views inside. This mountain sanctuary seamlessly combines modern comfort, solar technology, and nature’s serene beauty,

Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

141 W Ridge Rd, Stratton, VT 05360
/23
$369,000
- 2 Beds
- 2 Baths
- 1,150 Sq Ft
85 E Birch Rd Unit 21, Stratton, VT 05360

Discover the perfect mountain getaway with this 2-bedroom, 2-bath condo located just moments from all the action at Stratton Mountain. Whether you're hitting the slopes or enjoying the year-round amenities, this condo offers convenience and comfort at every turn.Step inside to a bright and inviting space with a cozy wood-burning fireplace, ideal for relaxing after a day on the trails. The kitchen

Carrie Mathews Winhall Real Estate

85 E Birch Rd Unit 21, Stratton, VT 05360
/32
$469,000
- 3 Beds
- 2 Baths
- 1,600 Sq Ft
17 Old Town Rd, West Dover, VT 05356

Snowmobilers paradise! Enjoy direct access to the VAST trail just down the street or from the backyard. Take in stunning winter views of Mount Snow & Haystack Mountains and summer panoramas of Haystack ski area and the surrounding mountain range. This custom-finished, ranch-style modular home features 3 bedrooms, 2 baths with numerous upgrades including new appliances, generator, more

Jennifer Hovey-Densmore Deerfield Valley Real Estate

17 Old Town Rd, West Dover, VT 05356
/25
$480,000
- 3 Beds
- 2.5 Baths
- 1,848 Sq Ft
15D Snow Tree Ln, Dover, VT 05356

Escape to the heart of Mount Snow! This inviting 3-bedroom plus loft, 2.5-bath townhouse offers the perfect blend of walk to the slopes convenience and serene natural beauty. Nestled beside a gentle stream, you're just a short walk from the lifts. Step inside via the covered mudroom to discover an open-concept living space, ideal for entertaining, featuring a cozy wood-burning fireplace and

Sheila Joyce-Albano Skihome Realty

15D Snow Tree Ln, Dover, VT 05356
/49
$899,000
- 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
/5
$125,000
- Land
- 0.43 Acre
- $290,698 per Acre
LOT 158/160 High Peak Way, Wilmington, VT 05363

Sun filled level Double lot with access to Public Water and Sewer right at the lot! All the hard work has been done so just bring your ideas. Located at the top of Haystack Rd Just across from Hole 17 at Haystack Golf Course on one side and the VAST trail system on the other makes this lot a year round paradise. Snowmobile right our your door to the Stack for dinner or over to the Hermitage Club

Heidi Zizza Four Seasons Sotheby's Int'l Realty

LOT 158/160 High Peak Way, Wilmington, VT 05363
/4
$99,000
- Land
- 0.32 Acre
- $309,375 per Acre
Lot 162 High Peak Way, Wilmington, VT 05363

Sun filled level corner lot with access to Public Water and Sewer right at the lot! All the hard work has been done so just bring your ideas. Located at the top of Haystack Rd Just across from Hole 17 at Haystack Golf Course on one side and the VAST trail system on the other makes this lot a year round paradise. Snowmobile right our your door to the Stack for dinner or over to the Hermitage Club

Heidi Zizza Four Seasons Sotheby's Int'l Realty

Lot 162 High Peak Way, Wilmington, VT 05363
/38
$42,500
- 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
$450,000
- 3 Beds
- 1.5 Baths
- 2,262 Sq Ft
1142 Western Ave, Brattleboro, VT 05301

You choose! Such a versatile property...invest in 2 rentals...live in either unit and rent the other...maybe develop the barn into another unit, home business, workshop..(check with Zoning). Just short of an acre (.86) the land is the big, big seller....the huge, mostly level back yard is already lush with flourishing fruit trees and blueberry bushes. There is a garage/gardening shed for your

Christine Lewis Brattleboro Area Realty

1142 Western Ave, Brattleboro, VT 05301
/52
$799,000
- 4 Beds
- 5.5 Baths
- 3,695 Sq Ft
37 Spring Hill Rd, West Dover, VT 05356

Discover the perfect blend of comfort and adventure in this stunning 4 bedroom, 6 bathroom home in the heart of Dover, VT. Boasting breathtaking mountain views, this property is just minutes from Mount Snow, premier golf courses, scenic walking trails, and the area's top restaurants. Step inside to find a bright, open-concept kitchen and dining area, ideal for gatherings.Each of the four bedrooms

Jillian Wimmelman Deerfield Valley Real Estate

37 Spring Hill Rd, West Dover, VT 05356
/45
$479,000
- 3 Beds
- 2 Baths
- 1,554 Sq Ft
466 Wheeler Rd, Windham, VT 05359

This 3-bedroom 2-bath Chalet is quietly nestled on 2.6 acres in the heart of Vermont’s ski country. The upper level has a wonderful, spacious kitchen, with an open floor plan combining the dining area and living room, with wood-burning fireplace, has access to the the wrap around deck. One bedroom with a walk-in closet is also on the upper level. The lower level boasts 2-bedrooms, a full bath,

Mike England Michael England Real Estate

466 Wheeler Rd, Windham, VT 05359
/25
$729,000
- 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
/13
$450,000
- 3 Beds
- 2 Baths
- 2,074 Sq Ft
36 Spruce St, Brattleboro, VT 05301

Perfect investment. Choose which flat you want to live in and have a bit of income, OR...consider this a long term investment! Such a special location and huge yard. Consider developing more apartments in the back of the house, and rent out the 40 x 40 steel frame building...OR develop into your dream workshop and let the rentals help pay for your fun. Rentals are below market for the

Christine Lewis Brattleboro Area Realty

36 Spruce St, Brattleboro, VT 05301
/13
$450,000
- 3 Beds
- 2 Baths
- 2,074 Sq Ft
36 Spruce St, Brattleboro, VT 05301

You choose! This amazing property can be used as one of the grand ladies of the neighborhood...just open a door or two and repurpose the kitchen...what a nice laundry room it would make...or use as is with 2 flats, live in 1 and have a bit of income from the other...What else, you might ask! There is a rear section of the house ready to be reclaimed, and a barn attached that could also be built

Christine Lewis Brattleboro Area Realty

36 Spruce St, Brattleboro, VT 05301
/20
$169,000
- 1 Bed
- 1 Bath
- 128 Sq Ft
1 N Ridge Rd, Town of Rockingham, VT 05101

Charming Tiny Home with Proven Airbnb Income! Cute as a button and packed with potential, this charming tiny home sits on a .44-acre corner lot in a highly desirable neighborhood. Currently operating as a successful Airbnb rental generating approximately $20,000 annually, it’s the perfect opportunity for an investment property, weekend getaway, or cozy full-time residence. Keep the property as

Bobbie Lynn Thomas The Thomas Group of Northern New England, LLC

1 N Ridge Rd, Town of Rockingham, VT 05101
/5
$55,900
- Land
- 2.30 Acres
- $24,304 per Acre
00 Loon Circle Private, Londonderry, VT 05148

This beautiful 2.3-acre buildable lot offers the perfect blend of convenience and natural beauty, with a wastewater system permit available. Just three miles from Magic Mountain and within easy reach of Stratton, Bromley, and Okemo, it's an ideal location for outdoor enthusiasts. The VAST trail is nearby for snowmobiling adventures, while a network of hiking trails is just a short walk away.

Carrie Mathews Winhall Real Estate

00 Loon Circle Private, Londonderry, VT 05148
/52
$1,495,000
- 4 Beds
- 3.5 Baths
- 3,203 Sq Ft
115 E Village Cir, Wilmington, VT 05363

This stunning 4 bedroom, 4 bath home is located just across the road from the Hermitage Club and 4 miles to Mount Snow. Entryway is set up to welcome everyone into this lovely home, with ample room for outdoor clothing. Next step into a beautiful kitchen and dining area featuring high-end kitchen appliances and a comfortable dining area. The first floor also has a living room, sitting area,

Tony Tribuno Skihome Realty

115 E Village Cir, Wilmington, VT 05363
/40
$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
/19
$299,000
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
8E Dover Green Loop, Dover, VT 05356

Spacious townhome at an incredible price in the Dover Green community located just a short drive or shuttle ride south of Mount Snow. This unit sits nestled towards the top of the development with great privacy and parking, and has had numerous recent upgrades to the roof, foundation, paint, siding, and whole house water filtration. The interior boasts a vaulted great room, wood burning fireplace

Adam Palmiter Berkley & Veller Greenwood/Dover

8E Dover Green Loop, Dover, VT 05356
/28
$19,500
- 1 Bath
- 407 Sq Ft
155 Qtr I, 89 Grand Summit Way Unit 155-1, Dover, VT 05356

Quarter-Share Ownership at the Grand Summit, 13 Weeks of Mountain Resort Living! Own a quarter share (deeded Interval-1) at the Grand Summit Hotel, providing 13 weeks of vacation per year on a rotating schedule. Whether you choose to use it, rent it, or trade it, this is an affordable way to enjoy the mountain resort lifestyle. This second-floor studio unit (407 sq. ft.) comfortably sleeps four

Donald Koelsch Deerfield Valley Real Estate

155 Qtr I, 89 Grand Summit Way Unit 155-1, Dover, VT 05356
/32
$49,000
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
269/71 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 sauna, hot tubs and outdoor heated pool, private owners only ski/golf locker rooms for

Kelly Agrillo Southern Vermont Realty Group

269/71 Qtr.4,89 Grand Summit Way, Dover, VT 05356
/49
$459,000
- 3,058 Sq Ft
470 Bills Rd, Wardsboro, VT 05355

This your opportunity to own a Quintessential Vermont Farmhouse with not one but TWO separate living quarters. Located smack dab in the middle of Mount Snow and Stratton so you can ski multiple Mountains and Golf Multiple courses. Live on one side and rent or Airbnb the other is a great option for this property. Currently both sides are being used as Airbnb's and have VERY strong rental income.

Heidi Zizza Four Seasons Sotheby's Int'l Realty

470 Bills Rd, Wardsboro, VT 05355
/49
$459,000
- 7 Beds
- 4.5 Baths
- 3,058 Sq Ft
470 Bills Rd, Wardsboro, VT 05355

This your opportunity to own a Quintessential Vermont Farmhouse with not one but TWO separate living quarters. Located smack dab in the middle of Mount Snow and Stratton so you can ski multiple Mountains and Golf Multiple courses. Live on one side and rent or Airbnb the other is a great option for this property. Currently both sides are being used as Airbnb's and have VERY strong rental income.

Heidi Zizza Four Seasons Sotheby's Int'l Realty

470 Bills Rd, Wardsboro, VT 05355
/55
$789,000
- 4 Beds
- 2.5 Baths
- 4,410 Sq Ft
165 Stone Hollow, Londonderry, VT 05148

This remarkable home offers a spacious layout, perfect for hosting family gatherings and entertaining guests. The large living room is ideal for cozy movie nights, while the separate recreation room, complete with foosball and a bar, adds an extra layer of fun. Cozy sitting areas are scattered throughout, providing the perfect spots to relax with a book or unwind in peace. Step outdoors and enjoy

Jessica Citera Cummings & Co

165 Stone Hollow, Londonderry, VT 05148

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