Windham County VT Homes for Sale

/32
$25,000
- Land
- 0.30 Acre
- $83,333 per Acre
139 Big Bend Loop, Wilmington, VT 05363

One of a handful of single lots remaining on the Hill! Septic design needs updating, Power is at the street. The lot is buffered by common land on both sides, and there is a drop off at the back. Access is best at the left end of the property, where a gentle slope takes you to this level plateau. View with clearing and in non-leaf seasons. Build your dream home and enjoy all the amenities

Sigrid Pickering Chimney Hill Realty

139 Big Bend Loop, Wilmington, VT 05363
/33
$425,000
- 1 Bed
- 1 Bath
- 700 Sq Ft
6878 Streeter Rd Unit 9&10, Wardsboro, VT 05360

Excellent opportunity to be close to everything Vermont has to offer and still feel secluded. This off grid efficient home is so easy to live in, get to and enjoy. IF you'd like to be on grid you're only about 7 power poles away. This offering is for currently combined 2 buildable lots which were subdivided many years ago. There is wonderful access to the woods for all activities. You can

Steve Goldfarb Deerfield Valley Real Estate

6878 Streeter Rd Unit 9&10, Wardsboro, VT 05360
/28
$205,000
- 2 Beds
- 1 Bath
- 844 Sq Ft
8577 Vermont 30 Unit H, Jamaica, VT 05343

Welcome to The Willows. Where convenience, comfort, and value come together in this well-appointed 2 bedroom, 1 bathroom condominium. Set privately back from Route 30, this thoughtfully maintained unit offers peaceful surroundings just two minutes from Strattons Access Road and within easy reach of Jamaica State Park and the West River.Ideal for first-time homebuyers or those looking to

Tara van de Velde Four Seasons Sotheby's Int'l Realty

8577 Vermont 30 Unit H, Jamaica, VT 05343
/23
$349,000
- 2 Beds
- 1 Bath
- 941 Sq Ft
57 Hartley Hill Rd S, Putney, VT 05346

NEW ROOF! This charmingly restored 1820's brick, former one-room schoolhouse has been meticulously expanded to include two bedrooms, a kitchen and full bathroom, and sits on a tranquil 5-acre lot with a mostly open, old pasture. The property retains its historical charm with exposed hand-hewn beams in the former schoolhouse that now serves as the living/dining area. Ideal for a cozy primary

Dan Normandeau Berkley & Veller Greenwood Country

57 Hartley Hill Rd S, Putney, VT 05346
/7
$499,000
- Land
- 2.00 Acres
- $249,500 per Acre
70 Overlook Dr, Dover, VT 05356

Stunning 2 acre building parcel at the prestigious Peaks at Mt Snow directly across from the ski resort. This lot affords tremendous privacy and exposure, but with amazing access and amenities including direct on call shuttle service from your door to the mountain, indoor pool, gym, clubhouse, and game courts. Paved road access, sewer, and water, means total peace of mind. Build your dream home

Adam Palmiter Berkley & Veller Greenwood/Dover

70 Overlook Dr, Dover, VT 05356
/20
$399,000
- 4 Beds
- 3.5 Baths
- 2,575 Sq Ft
3730 Route 100, Wardsboro, VT 05355

Property is being sold "as is where is" and does need some TLC. The house is set back off the road quite a bit for total privacy and there is a pond on the property. There is a one car garage, a full daylight basement, and a sun room.Sellers have given permission to encourage all offers.

Ginny Read Read Realty LTD

3730 Route 100, Wardsboro, VT 05355
/60
$639,000
- 5 Beds
- 2.5 Baths
- 3,000 Sq Ft
673 Route 121 E, Grafton, VT 05146

Step into a classic Vermont farmhouse from the 1830s, built by a successful mill owner and loved by its current stewards for over fifty years. Minutes from the center of charming Grafton and only thirty minutes from Okemo, this beautiful property offers wide, level lawns and sits on 45 acres of untouched woodland in the hills behind—never logged and fully unencumbered. Inside, the original

Keri Cole Williamson Group Sothebys Intl. Realty

673 Route 121 E, Grafton, VT 05146
/26
$725,000
- 18 Beds
- 8 Baths
- 4,932 Sq Ft
29 Canal St, Brattleboro, VT 05301

High cash flow 100% occupied 8 unit located in downtown Brattleboro. This property was recently renovated and is being listed at a 11% cap and an annual Net Operating Income estimated at north of ~$80K (12% cap without management fees). The property features an attractive mix of unit types and sizes including 4x rarely available oversized 3br, 2x2br and 2x1brA new owner can step into to

Michael Gilman 3GEN Real Estate Inc

29 Canal St, Brattleboro, VT 05301
/29
$849,000
- 3 Beds
- 2 Baths
- 2,216 Sq Ft
601 Bellows Falls Rd, Putney, VT 05346

A special and unique offering of a 40 acre homestead in sought after Putney, Vermont. Set back from the road on a private drive is a 3-4 bedroom cape with full basement and attached two car garage. Special features include an observatory room, entry foyer with spacious office, quality built-ins, dormers and a swimming pond. A second building offers a rustic exterior, modern interior, wonderful

Jody Graves Berkley & Veller Greenwood Country

601 Bellows Falls Rd, Putney, VT 05346
/18
$499,000
- 4 Beds
- 2.5 Baths
- 2,060 Sq Ft
3 Mill Rd, West Dover, VT 05356

When you picture a rustic and woodsy Vermont retreat, but with modern comforts, this is that home. Spacious chalet style home located conveniently on the MOOver shuttle route 3 miles from the Mount Snow Ski Resort. This 4 bedroom, 2.5 bath home has exposed natural woodwork throughout, a great open concept floor plan with large living room and updated gas fireplace on brick hearth, direct views of

Adam Palmiter Berkley & Veller Greenwood/Dover

3 Mill Rd, West Dover, VT 05356
/14
$1,750,000
- 4 Beds
- 3.5 Baths
- 2,698 Sq Ft
63 Sunbowl Ridge Rd Unit 63A, Stratton, VT 05360

The absolute best location in one of Stratton's most desirable communities!This four bedroom, three and one half bath townhome is located directly on the ski trail. Immaculate interior. Bright sunny interior with eastern and southern exposure. One car garage, family room, back patio with new hot tub. Private pool and hot tubs located a short walk away. Shuttle service to Stratton base area

John Sikes Stratton Real Estate

63 Sunbowl Ridge Rd Unit 63A, Stratton, VT 05360
/27
$539,000
- 3 Beds
- 2.5 Baths
- 2,150 Sq Ft
16A Snow Tree Ln Unit Cedars 1, Dover, VT 05356

Rare Rare Rare! There are only 2 townhomes of this style at the desirable Snowtree development, and this particular 3 bedroom, 3 bath has been completely renovated. Walk out your private entry to the base area at Mount Snow via the convenient stream crossing bridge to access the magic carpet and tubing area, ideal for the ski season, but also any summer festivals. If someone doesn't ski they can

Adam Palmiter Berkley & Veller Greenwood/Dover

16A Snow Tree Ln Unit Cedars 1, Dover, VT 05356
/17
$159,000
- Land
- 14 Acres
- $11,142 per Acre
1 Berrie Ln, Townshend, VT 05353

Over 14 acres of raw land in a private setting with potential local mountain views with clearing. State wastewater permit already on file for a conventional, in-ground septic for a 3-bedroom home. Potential owner financing available. Agent is related to seller.

Samantha Bartlett Lowe's Real Estate, LLC

1 Berrie Ln, Townshend, VT 05353
/12
$675,000
- Land
- 45 Acres
- $15,000 per Acre
000 Under the Mountain Rd, South Londonderry, VT 05155

Travel down a quiet, tree-lined country road past historic homes, horse farms, and a large nature preserve to discover this magnificent property with views of Stratton and Bromley mountains in the distance. A large open field graced with wild flowers, apple trees and classic Vermont rock walls provides an ideal level home site, protected on three sides by extensive mature woods. The parcel has

Steve Stettler Four Seasons Sotheby's Int'l Realty

000 Under the Mountain Rd, South Londonderry, VT 05155
/23
$350,000
- 3 Beds
- 2.5 Baths
- 1,440 Sq Ft
61 Country Club Rd, West Dover, VT 05356

Charming 3-Bedroom Condo Just Minutes from Mount Snow!Welcome to your perfect Vermont getaway! This beautifully maintained 3-bedroom, 2.5-bath condo is ideally located in Southern Vermont, just minutes from the renowned Mount Snow Ski Resort and the Mount Snow Golf Course. Whether you're an outdoor enthusiast or seeking a peaceful retreat, this property offers the best of all

Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

61 Country Club Rd, West Dover, VT 05356
/13
$249,000
- Land
- 0.71 Acre
- $350,704 per Acre
24 Lower Highlands Rd, Dover, VT 05356

Exceptional development opportunity just two minutes from the Mount Snow base area. This 0.71-acre parcel is fully approved for a four-unit residence with occupancy for 16. State wastewater and town construction permits are secured, and full architectural and structural engineering plans will convey.All approvals are valid for the next two years, allowing for immediate construction. With

Jacki Murano Southern Vermont Realty Group

24 Lower Highlands Rd, Dover, VT 05356
/12
$1,050,000
- 3 Beds
- 3 Baths
- 1,501 Sq Ft
759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340

Designed with the mountain enthusiast in mind, and located just a short walk from the Stratton Resort Village and ski slopes, this three bedroom three bath condominium offers quality and convenience. Private parking, pool, hot tub, sauna and shuttle to the slopes.

John Sikes Stratton Real Estate

759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340
/36
$499,000
- 7 Beds
- 6 Baths
- 2,178 Sq Ft
343 Haystack Rd, Wilmington, VT 05363

This spacious home is located near outdoor recreation spots like Mount Snow and Haystack Country Club. Tucked back on 3 acres with wooded surroundings offering privacy amongst the trees. The main house offers four bedrooms, four baths; including a large primary suite. The spacious basement has a kitchen, bath and living space with walkout access to the backyard. The three-car garage with a

Jessica Citera Cummings & Co

343 Haystack Rd, Wilmington, VT 05363
/52
$525,000
- 3 Beds
- 2.5 Baths
- 2,023 Sq Ft
6940 Coolidge Hwy, Guilford, VT 05301

Located just north of the Massachusetts border, this home with two car detached garage is conveniently just 15 minutes from both Greenfield and Brattleboro.As you step inside to the mudroom you'll enter the coziest of kitchens radiating warmth and character. Featuring a wood stove, a stunning brick hearth with beehive oven, wooden beams adding rustic charm, while a cathedral ceiling keeps the

Rebecca Seymour Brattleboro Area Realty

6940 Coolidge Hwy, Guilford, VT 05301
/58
$599,000
- 4 Beds
- 2 Baths
- 3,090 Sq Ft
301 Maple St, Brattleboro, VT 05301

This is IT! Summer is here! The gardens are ablaze, the deck is perfect for the evening sip of something cool and there is open sky for sightings like the strawberry moon and shooting stars. Treat yourself to your own spa....the sweet spot is the oversized salt pool, surrounded by lush greenery for privacy and an apron for sunning. Add some of your own fun and you will stay at home,

Christine Lewis Brattleboro Area Realty

301 Maple St, Brattleboro, VT 05301
/40
$85,000
- Land
- 1.03 Acres
- $82,524 per Acre
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
/29
$88,900
- Land
- 13 Acres
- $6,984 per Acre
0 Skyline Dr, Vernon, VT 05354

12+ Acres of Wooded Vermont Beauty This 12.73-acre parcel in peaceful Vernon, VT offers the ideal blend of privacy, natural beauty, and accessibility. With ample road frontage and electric available at the street, so much potential whether it be a vacation retreat, full time dwelling or investment opportunity. The land features a mix of mature hardwoods and potential

Morriah Adams BHG Masiello Brattleboro

0 Skyline Dr, Vernon, VT 05354
/30
$18,000
- 1 Bath
- 407 Sq Ft
217 Qtr. 3,89 Grand Summit Way, Dover, VT 05356

Slope side ski in/out with ski trail views and full hotel amenities! Gain that mountain resort life style at a truly affordable price. Use it, Rent it, Trade it! With 13 weeks of vacation a year round, benefits of Grand Summit ownership including the best ski in/out mountain location available-this is an opportunity to seriously upgrade your vacations. Use of the Grand Summit amenities all year

Jacki Murano Southern Vermont Realty Group

217 Qtr. 3,89 Grand Summit Way, Dover, VT 05356
/41
$589,000
- 5 Beds
- 4 Baths
- 2,686 Sq Ft
23 Summit Meadows Cir, Dover, VT 05356

Spacious 5-bedroom, 4-bath home with additional designated office space, den and 2 car garage on 1.17 acres! Thoughtful floor plan includes a first-floor primary suite with wood-burning fireplace, a guest bedroom and full bath, a private office with its own full bath, and a large mudroom with laundry and storage. The open living room with vaulted ceilings, wood-burning fireplace, and abundant

Jacki Murano Southern Vermont Realty Group

23 Summit Meadows Cir, Dover, VT 05356
/30
$400,000
- 3 Beds
- 1 Bath
- 1,338 Sq Ft
2779 Pikes Falls Rd, Jamaica, VT 05343

Nestled just 5 miles from Stratton's base lodge on the historic grounds of the former White Mop Wringer Co., this remarkable home blends rich history with modern craftsmanship. Built in 2001, the house sits where, in the 1800s, Cassius A. White invented the mop wringer, making Jamaica, Vermont the birthplace of the first mop wringer factory. While the water wheel that powered the factory is no

Carrie Mathews Winhall Real Estate

2779 Pikes Falls Rd, Jamaica, VT 05343
/40
$125,000
- Land
- 1.58 Acres
- $79,114 per Acre
408 Fox Mountain Rd, Wilmington, VT 05363

Top of the Hill at the end of the Road! Triple building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sacon 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

408 Fox Mountain Rd, Wilmington, VT 05363
/35
$125,000
- Land
- 1.52 Acres
- $82,237 per Acre
406 Fox Mountain Rd, Wilmington, VT 05363

Top of the Hill at the end of the Road! Triple 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 Clubhouse. If you've been thinking of building your dream home, this is a great opportunity!

Sigrid Pickering Chimney Hill Realty

406 Fox Mountain Rd, Wilmington, VT 05363
/19
$799,000
- 4 Beds
- 4 Baths
- 1,575 Sq Ft
4L Trailside Village Way Unit H34, Dover, VT 05356

Welcome to H34 Trailside Village Way, a rare opportunity to own a stunning 4-bedroom, 4-bath slopeside condo in the coveted Seasons on Mount Snow community. This impeccably maintained, never-rented home offers true ski-in/ski-out access—step out your door and onto the trail for unbeatable convenience all winter long.Inside, the open-concept living space is bathed in natural light,

Jessica Bentz Four Seasons Sotheby's Int'l Realty

4L Trailside Village Way Unit H34, Dover, VT 05356
/18
$439,000
- 2 Beds
- 2 Baths
- 1,040 Sq Ft
6 Northbrook Village Way Unit 23, Dover, VT 05356

This beautiful 2-bedroom, 2-bath end-unit condo in Seasons on Mount Snow offers the perfect combination of convenience, comfort, and mountain living. The open-concept floor plan with living, dining, and kitchen areas is perfect for family gatherings and entertaining. This mountain retreat, featuring a cozy floor-to-ceiling fieldstone fireplace, a slopeside location, and an abundance of natural

Jessica Bentz Four Seasons Sotheby's Int'l Realty

6 Northbrook Village Way Unit 23, Dover, VT 05356
/33
$85,000
- Land
- 1.04 Acres
- $81,731 per Acre
402 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 Clubhouse. If you've been thinking of building your dream home, this is a great opportunity!

Sigrid Pickering Chimney Hill Realty

402 Fox Mountain Rd, Wilmington, VT 05363
/32
$185,000
- 3 Beds
- 1.5 Baths
- 1,664 Sq Ft
47 Adams St, Westminster, VT 05158

Nestled on a quiet Kissell Hill neighborhood, this bright and well-maintained home offers 3 large bedrooms and 1.5 baths with a versatile 1.5-story addition. The large living room features a beautiful bay window, allowing natural light to fill the space. The country-style kitchen flows seamlessly into a cozy three-season enclosed porch, perfect for relaxing or entertaining.Enjoy a level

Kate Barry EXP Realty

47 Adams St, Westminster, VT 05158
/53
$374,000
- 2 Beds
- 2 Baths
- 1,250 Sq Ft
5 Black Bear Ln Unit 5F, Dover, VT 05356

Turnkey Townhouse in Sought-After Bears Crossing at Mount Snow, Vermont! Don’t miss this rare opportunity to own a beautifully updated end unit in one of the best-maintained buildings in Bears Crossing! Perfectly situated just steps from the clubhouse, heated pool, tennis and pickleball courts, and the dedicated Moover shuttle bus to Mount Snow—this location offers both convenience and

Steve Goldfarb Deerfield Valley Real Estate

5 Black Bear Ln Unit 5F, Dover, VT 05356
/39
$425,000
- 4 Beds
- 3 Baths
- 2,460 Sq Ft
6795 Vt Route 100, Londonderry, VT 05148

Charming Property with Endless Possibilities in Southern VermontNestled on 5 acres in the heart of Southern Vermont, this unique property offers the perfect blend of history, versatility, and potential. Currently operating as a successful Quilt Shop, this property presents an exceptional opportunity for a variety of uses – whether you’re looking to return it to a spacious home with

Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

6795 Vt Route 100, Londonderry, VT 05148
/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
/15
$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
/51
$544,400
- 6 Beds
- 4 Baths
- 3,000 Sq Ft
22 Chestnut St, Brattleboro, VT 05301

4 condo units being sold together as a great residential package investment opportunity! Rent them, live in one and/or sell them off individually. 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. The property features a large shared yard, off-street parking, and strong rental potential. The

Erica Reynolds Southern Vermont Realty Group

22 Chestnut St, Brattleboro, VT 05301
/18
$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
/47
$999,000
- 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
- 1,500 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

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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.