Windham County VT Homes for Sale

/11
$30,000
- Land
- 1.00 Acre
- $30,000 per Acre
58 Boardman Loop, Wardsboro, VT 05360

Nestled in the heart of ski country, this property is perfectly situated near the slopes of Mount Snow and Stratton Ski areas. With snowmobile trails, hiking, kayaking, and the stunning Green Mountain National Forest just minutes away, the small community of Snow Mountain Farms West invites you to embrace the natural beauty of Vermont. This 1-acre lot already has a wastewater permit for a

Michelle O'Neil Deerfield Valley Real Estate

58 Boardman Loop, Wardsboro, VT 05360
/30
$255,000
- 3 Beds
- 1 Bath
- 1,144 Sq Ft
77 Griswold Dr, Bellows Falls, VT 05101

Nestled on a dead-end street in a sought-after neighborhood, this charming split-level ranch offers both comfort and potential. Featuring three spacious bedrooms and a full bath, the home boasts an inviting layout perfect for modern living. The kitchen opens to a lovely porch—ideal for enjoying your morning coffee or evening relaxation. Set on a generous 0.37-acre lot, there’s plenty of outdoor

Rob Weltz Barrett & Valley Assoc. Inc

77 Griswold Dr, Bellows Falls, VT 05101
/2
$90,000
- 3 Beds
- 1 Bath
- 1,030 Sq Ft
93 Clark St, Brattleboro, VT 05301

An affordable opportunity for a new beginning, for both you and the home! Located in an evolving neighborhood where a new generation is investing, walk to downtown. This corner lot has off street parking, a bit of yard for some planting or sunning, and what the current owner has used as a workshop. This one will take cash or a rehab loan, but is being occupied so systems are working. Please,

Christine Lewis Brattleboro Area Realty

93 Clark St, Brattleboro, VT 05301
/2
$89,000
- 4 Beds
- 3 Baths
- 2,108 Sq Ft
321 Williams St, Brattleboro, VT 05301

Great opportunity for starting or expanding your investment portfolio. Good rental income and affordable property. Nice location. Good parking for tenants and private porches. Minimal yard maintenance.

Susan Bellville Bellville Realty

321 Williams St, Brattleboro, VT 05301
/33
$515,000
- 3 Beds
- 2 Baths
- 2,016 Sq Ft
44 Tanglewood Ln Unit E, Dover, VT 05356

Welcome to the best Mount Snow view at Timber Creek! This 3 bedroom 2 bath condo has been owned and loved by the same family since its inception. You'll enjoy being right across the street from the North entrance to Mount Snow with access to a free shuttle, along with all the benefits of the Sugarhouse club house and sports complex. There's a basketball court, tennis/pickleball courts,

Mike Masters Four Seasons Sotheby's Int'l Realty

44 Tanglewood Ln Unit E, Dover, VT 05356
/5
$210,000
- 2 Beds
- 1 Bath
- 560 Sq Ft
1570 Somerset Rd, Wilmington, VT 05363

Somerset Wilderness,Close to the reservoir and Deerfield River. Boating. snowmobiling, hunting, and hiking. Open land with trails and apple trees. Abuts the National Forest.

Mark Yule BHG Masiello Brattleboro

1570 Somerset Rd, Wilmington, VT 05363
/21
$26,000
- 1 Bed
- 1 Bath
- 673 Sq Ft
222, Qtr 1 89 Grand Summit Way Unit 222, Dover, VT 05356

An opportunity to own at the beautiful and conveniently located trailside, Grand Summit Hotel. Enjoy the ski-on, ski-off lifestyle, while also experiencing the luxuries of hotel amenities with this spacious slope facing quarter share unit at the beautiful Grand Summit, directly at the base of Mount Snow! This sleep 6 unit is perfect for family, guests or great rental options. The unit features a

Prema Fitzpatrick Skihome Realty

222, Qtr 1 89 Grand Summit Way Unit 222, Dover, VT 05356
/55
$349,000
- 3 Beds
- 2 Baths
- 2,910 Sq Ft
597 Gates Pond Rd, Jacksonville, VT 05342

Classic Greek Revival Expanded in True New England Farmhouse Fashion w/Studios, Timber-Frame Barn, Workshop, & Greenhouse on 3+ surveyed Acres. This 3-bed, 2-bath offers approximately 3,000 square feet of finished living space w/ flowing layout connecting a series of versatile spaces—all under one roof. From the original formal rooms of the farmhouse, step into a sequence of functional bonus

Jacki Murano Southern Vermont Realty Group

597 Gates Pond Rd, Jacksonville, VT 05342
/47
$985,000
- 6 Beds
- 4.5 Baths
- 3,500 Sq Ft
5825 Vermont 30, Townshend, VT 05353

Equine Estate with 21 acres. 6+ Beds, 5 Baths! Unique and versatile property has been operated as a 501(c)(3) equine rescue facility since 2005. 3-bedroom MAIN HOUSE with attached 1-bedroom accessory unit, ideal for guests, staff, income. MAIN BARN w/8 box stalls and wash stall. Hay elevator, automatic water, heated tack rooms, office with a deck overlooking the public forest. The “CARRIAGE

Jacki Murano Southern Vermont Realty Group

5825 Vermont 30, Townshend, VT 05353
/47
$1,695,000
- 4 Beds
- 3.5 Baths
- 3,666 Sq Ft
3 Overbrook Dr, Dover, VT 05356

STUNNING NEW CONSTRUCTION, SPECTACULAR VIEWS, GREAT LOCATION! Open House Saturday, 7/5/2025, 12-2pm! Set against the backdrop of Mount Snow, this just completed luxury single-family home offers the perfect blend of modern design, spacious living.Located just minutes from the ski mountain, The Outlook at Mount Snow offers the perfect blend of mountain modern luxury and the ultimate

John Redd Skihome Realty

3 Overbrook Dr, Dover, VT 05356
/53
$1,200,000
- 4 Beds
- 3 Baths
- 3,506 Sq Ft
339 Coldbrook Rd, Wilmington, VT 05363

Just a half mile from The Hermitage Club, 3.5 miles to Mount Snow, and only a mile from Haystack Golf Club, this 4 bedroom, 3 bathroom home on 10.1 acres offers the perfect blend of rustic charm and modern comfort. Direct access to the VAST snowmobile trails and mountain views makes this an outdoor enthusiast’s dream.Step inside to find warm wood finishes, exposed beams, and rich natural textures

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

339 Coldbrook Rd, Wilmington, VT 05363
/33
$799,000
- 5 Beds
- 2.5 Baths
- 3,064 Sq Ft
32 Old Town Rd, Dover, VT 05356

Tucked away on a country road in Dover, Vermont, this inviting five bedroom, three bathroom home offers the perfect blend of comfort, functionality, and outdoor enjoyment. Set on a scenic open lot with a tranquil pond and open views, the property includes a spacious inlaw apartment on the walkout lower level ideal for guests, extended family, or potential rental income.The main home features

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

32 Old Town Rd, Dover, VT 05356
/36
$529,000
- 3 Beds
- 3 Baths
- 1,510 Sq Ft
4A Junior's Way, Dover, VT 05356

This newly constructed 3-bedroom, 3-bath townhome, built in 2022, offers modern mountain living just minutes from the Mount Snow ski resort. With a convenient location, the slopes can easily be accessed via a short walk to the free MOOver Bus. The home boasts three levels of living, an open concept design with a fireplace, spacious living and dining areas, a beautiful updated kitchen, and a

Prema Fitzpatrick Skihome Realty

4A Junior's Way, Dover, VT 05356
/16
$259,900
- Land
- 29 Acres
- $8,901 per Acre
1270 Melendy Hill Rd, Guilford, VT 05301

A rare find! This amazing land has long range views, privacy and close to everything! There is a right of way for egress, and will be perfect for an off grid tuck away cabin or primary. A small meadow is part of the 2 acre exemption for house site, just at the end of the existing drive...easy to get to and just the beginning of the land. Mostly Black Birch, Sugar Maple and Hemlock, there is

Christine Lewis Brattleboro Area Realty

1270 Melendy Hill Rd, Guilford, VT 05301
/24
$33,000
- 1 Bed
- 2 Baths
- 709 Sq Ft
243/245 qtr 2, Grand Summit Way Unit 243/245, Dover, VT 05356

TRAILSIDE! A great and affordable opportunity to own the best location to be on the Mount Snow ski trails. Unit 243 boast a queen size Murphy bed, kitchenette and full bath. This unit sleeps 2 and has amazing views of the mountain. Unit 245 has 2 queen beds a full bath, a mini fridge and a private deck overlooking the ski trails. This lockout combination allows you to use the studio and the

Sheila Joyce-Albano Skihome Realty

243/245 qtr 2, Grand Summit Way Unit 243/245, Dover, VT 05356
/12
$315,000
- Land
- 19 Acres
- $16,640 per Acre
0 Forest Heights Rd, West Dover, VT 05356

Are you ready to turn your dream home into a reality? This expansive parcel of land, located just 2 miles from the slopes of Mount Snow, is waiting for your vision. The property offers an ideal combination of privacy and seclusion and with some clearing, you can unveil extraordinary views of the Mount Snow ski slopes, creating the perfect backdrop for your dream home. The property boasts

Michelle O'Neil Deerfield Valley Real Estate

0 Forest Heights Rd, West Dover, VT 05356
/60
$425,000
- 3 Beds
- 2 Baths
- 1,520 Sq Ft
96 E Brook Crossing Unit CHC209.000, Wilmington, VT 05363

New Listing in Section C! Quiet corner of the Resort features this Classic Chalet with a mudroom entry, bedroom with slider to the deck, a full bath, open concept kitchen with wood cabinets and breakfast bar, dining area with a bay window, living area with vaulted ceiling, wood burning fireplace and slider to the deck. Upstairs has a full bath with skylight and two bedrooms, one with a skylight

Sigrid Pickering Chimney Hill Realty

96 E Brook Crossing Unit CHC209.000, Wilmington, VT 05363
/60
$695,000
- 3 Beds
- 2.5 Baths
- 3,415 Sq Ft
23 Meeting House Ln, Brattleboro, VT 05301

First Time on the Market – Premier Brattleboro Location!Nestled on one of the most desirable lots in one of Brattleboro’s finest neighborhoods, this well-maintained home is being offered for sale for the very first time! Custom-built by the current owner in 1970 with attention to detail, this spacious ranch offers comfort, functionality, and an impressive list of amenities.Perfect for

Bert Inman RE/MAX Town & Country

23 Meeting House Ln, Brattleboro, VT 05301
/25
$27,999
- 2 Beds
- 2 Baths
- 745 Sq Ft
304/306, Qtr 3 Grand Summit Way, Dover, VT 05356

Use it, Rent it, Trade it! Does 13 weeks of vacation year-round sound nice? This valley-side lockout unit on the top floor features an open-concept kitchen, dining, and living area with a Murphy bed, as well as a full bath. The adjoining room features two queen beds and an additional full bathroom. The lockout-style unit offers the option of using both sides or using one and renting the other

Patricia Fitzpatrick Skihome Realty

304/306, Qtr 3 Grand Summit Way, Dover, VT 05356
/40
$1,695,000
- 7 Beds
- 7.5 Baths
- 8,364 Sq Ft
251 Pratt Bridge Rd, Jamaica, VT 05343

Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas & the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated B&B. Prepare to be Enchanted! An

TG Glazer Winhall Real Estate

251 Pratt Bridge Rd, Jamaica, VT 05343
/33
$430,000
- 3 Beds
- 3 Baths
- 2,446 Sq Ft
211 Upper Dam Rd, Wilmington, VT 05363

Charming Saltbox Chalet located in the desirable Chimney Hill community. This classic chalet is just a short drive from Wilmington Village, Lake Whitingham, the Haystack Golf Course, and Mount Snow Ski Resort. The light-filled interior offers a welcoming open concept great room with vaulted ceilings, a wood-burning fireplace with brick hearth, and hardwood flooring. The kitchen features granite

Monique White Deerfield Valley Real Estate

211 Upper Dam Rd, Wilmington, VT 05363
/43
$725,000
- 2 Beds
- 2 Baths
- 2,144 Sq Ft
956 Old Cheney Rd, West Townshend, VT 05359

This 2-bed/2-bath, south-facing Vermont farmhouse sits on 41 acres with great views. Originally built in 1790, it’s had a thorough, sensitive restoration to preserve historical integrity while offering modern comfort. The house has an Energy Star® Tamko metal roof resembling the original slate, a new septic system (2022), whole house propane generator, partially spray foamed basement, and

Kim Meeker Southern Vermont Realty Group

956 Old Cheney Rd, West Townshend, VT 05359
/47
$995,000
- 5 Beds
- 1 Bath
- 1,224 Sq Ft
6036 Jacksonville Stage Rd, Guilford, VT 05301

Welcome to a rare and breathtaking slice of Vermont. This expansive 216-acre farm offers a beautiful mix of open pastures, mature woodlands, fruit trees, berry bushes, and a small section of scenic wetlands – a true haven for nature lovers and outdoor enthusiasts seeking peace and space in every direction. Set along a quiet dirt road near the Massachusetts border, with the added convenience of

Melissa Nebelski Skihome Realty

6036 Jacksonville Stage Rd, Guilford, VT 05301
/22
$56,800
- 3 Beds
- 3 Baths
- 1,323 Sq Ft
157/265/267qtr3 Grand Summit Way Unit 156/265/267, Dover, VT 05356

TRAILSIDE. Imagine the opportunity owning a unit at the Grand Summit that can be used as a studios sleep 4, a 1 bedroom sleep 6 or even host s 12 guests. Unit 157 has a sleep sofa and a Murphy bed, full kitchenette and a full bath. Unit 265 studio with a sleep sofa, Murphy bed, kitchenette and full bath, sleep 4. Unit 267 has 2 queen beds, sleep 4 and a balcony. Enjoy being at the best location

Sheila Joyce-Albano Skihome Realty

157/265/267qtr3 Grand Summit Way Unit 156/265/267, Dover, VT 05356
/10
$175,000
- Land
- 8 Acres
- $21,875 per Acre
680 W River Rd, Brattleboro, VT 05301

8 acres only 2 miles from Brattleboro situated across the road from the West River. Existing gated gravel driveway is in. Gravel on site and road roughed into a high plateau with designs for SIX 1-2 bedroom cottages. Topographical survey, septic design plans and other existing engineering are complete which make this an attractive option for someone looking to develop a parcel into a cottage

Chris Long BHG Masiello Brattleboro

680 W River Rd, Brattleboro, VT 05301
/35
$389,900
- 5 Beds
- 3 Baths
- 3,364 Sq Ft
21 Main St, Saxtons River, VT 05154

Welcome to history, this 1830's colonial home has so much charm and character to offer! This home is situated in the quaint village of Saxtons River just feet from the Local market store as well as the admired and prestigious Vermont Academy School. With plenty of space to host whether it be in the large grand feeling living room with the original woodwork and fireplaces or the spacious back yard

Thaddeus Abare Barrett and Valley Associates Inc.

21 Main St, Saxtons River, VT 05154
/31
$23,950
- 1 Bed
- 1 Bath
- 673 Sq Ft
356Qtr.1, 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

356Qtr.1, 89 Grand Summit Way, Dover, VT 05356
/40
$499,000
- 4 Beds
- 2 Baths
- 1,908 Sq Ft
119 Main St, Putney, VT 05346

MOTIVATED SELLERS! Built in 1798, 119 Main Street is the third oldest home in Putney. With its original beams, colonial architecture, and location on Main Street, it's a historic gem in waiting for new people to love it. The owner who resided here for many years, took pride in preserving and adding to the beautiful terraced perennial gardens throughout the large in-town lot, which is just under

Heather Gleim CENTURY 21 North East

119 Main St, Putney, VT 05346
/35
$949,000
- 4 Beds
- 3.5 Baths
- 2,272 Sq Ft
12 Encore Place, Dover, VT 05356

Mountain Modern Living with unmatched ski views of Mount Snow. Discover the perfect blend of luxury and nature in this 3 year young contemporary home ideally situated to capture breathtaking unobstructed views of Carinthia. This thoughtfully designed 4 bedroom home offers an open concept floor plan while still offering privacy and cozy spaces that highlight the beauty of the alpine landscape.

Heidi Zizza Four Seasons Sotheby's Int'l Realty

12 Encore Place, Dover, VT 05356
/55
$640,000
- 3 Beds
- 2.5 Baths
- 1,708 Sq Ft
15 Haymaker Ln Unit 6B, Wilmington, VT 05363

A Wonderfully well built and maintained spacious Townhome in Desired Powderhorn Condo Association! Nestled in the heart of Vermont’s breathtaking Green Mountains, this beautifully maintained 3-bedroom, 2.5-bathroom condo is your dream getaway. Located just moments from mountain biking, skiing, snowmobiling including VAST trails. Two minutes from 2 world class golf courses and the stunning

Steve Goldfarb Deerfield Valley Real Estate

15 Haymaker Ln Unit 6B, Wilmington, VT 05363
/5
$185,000
- Land
- 0.84 Acre
- $220,238 per Acre
1 Pinnacle View Ln, Dover, VT 05356

If it's close proximity you want to skiing Mt. Snow then this is your place to build your dream home. Just off a paved road in a small 5 lot subdivision. Underground utilities and sewer hookup available. Convenient to lakes, golf and restaurants, a diamond in the rough. Winter views of Mt. Snow (says owner)

Regina Perrotto Skihome Realty

1 Pinnacle View Ln, Dover, VT 05356
/21
$389,000
- 3 Beds
- 2.5 Baths
- 1,200 Sq Ft
5E Polar Bear N, Dover, VT 05356

Two-bedroom, one sleeping space loft, three-bath townhome in Bears Crossing, located minutes from Mount Snow. This unit includes access to a private Ski Home trail from the slopes and a seasonal shuttle to the mountain. The layout features a ground-level mudroom with bench seating and storage, two bedrooms—including a main-level bedroom with an en suite bath—and an additional full bath. The upper

Erica Reynolds Southern Vermont Realty Group

5E Polar Bear N, Dover, VT 05356
/43
$398,000
- 6 Beds
- 2 Baths
- 960 Sq Ft
247 Vt Route 100 N, Wilmington, VT 05363

Conveniently located on Route 100 between Wilmington Village and Mount Snow. Two separate 3 bedroom, totally renovated, units. This would be a wonderful multi-generational home, two family purchase, use one unit - rent one unit. Wheeler Farm view of pasture and mountain ranges. Exterior garden shed. Plenty of parking, an amazing view and waiting for you!

Janet Boyd Boyd Real Estate

247 Vt Route 100 N, Wilmington, VT 05363
/31
$459,000
- 4 Beds
- 3 Baths
- 1,854 Sq Ft
132 Sun and Ski Rd, Wilmington, VT 05363

Welcome to Chateau Chelsea! This charming three-level, 4-bedroom, 3-bathroom single-family home is situated in the heart of Vermont’s picturesqueGreen Mountains. Named after the owners' beloved pup, this property has been a cherished gathering place for family and friends year-round. Conveniently located just over 2 hours from Boston, 90 minutes from Hartford, CT, and less than 4 hours from NYC,

Patrice Schneider Southern Vermont Realty Group

132 Sun and Ski Rd, Wilmington, VT 05363
/6
$54,900
- Land
- 2.40 Acres
- $22,875 per Acre
0 Route 30 Unit 5048856, Jamaica, VT 05343

Tucked along a quiet, town-maintained road in Jamaica, Vermont, this beautifully wooded parcel places you right in the heart of southern Vermont’s legendary ski country. Stratton, Magic, and Bromley Mountains are each only minutes away, giving you three distinct downhill experiences—plus miles of lift-served mountain-bike trails—at your fingertips. Yet winter fun is just the beginning: the West

Joe Castaluccio Winhall Real Estate

0 Route 30 Unit 5048856, Jamaica, VT 05343
/21
$375,000
- 2 Beds
- 2 Baths
- 1,024 Sq Ft
6F Deer Creek Rd, Dover, VT 05356

A super location and a great value, just a few minute walk to the brand new Sundance Express high speed lifts at Mount Snow! Here is your opportunity to own a well maintained and ideally located condo with low HOA fees!This top floor, 2 bedroom plus loft unit offers cathedral ceilings, big windows, a wood burning fireplace and a balcony that directly faces towards the mountain across the

Prema Fitzpatrick Skihome Realty

6F Deer Creek Rd, Dover, VT 05356
/31
$947,000
- 5 Beds
- 3 Baths
- 3,015 Sq Ft
100 Mowing Way, Wilmington, VT 05363

Impeccably maintained golf course home nestled in the Vermont mountains just 5 miles from lakes, ski resorts, and scenic trails. Perfect for entertaining or quiet enjoyment, this elegant property combines luxury and comfort in a stunning natural setting. The soaring great room features beamed ceilings, radiant heated hickory floors, and a gas fireplace flanked by built ins. A chefs dream kitchen

Leslie Fraser Four Seasons Sotheby's Int'l Realty

100 Mowing Way, Wilmington, VT 05363
/49
$795,000
- 4 Beds
- 3.5 Baths
- 1,993 Sq Ft
65 Styles Branch Rd Unit 819, Stratton, VT 05360

Welcome to Styles Brook 819, an impeccably maintained end unit townhome nestled in the heart of Stratton Mountain Resort. This spacious and light filled 4 bedroom, 3.5 bath residence offers everything you need for four season mountain living, whether you're hitting the slopes in winter or enjoying the cool summer breeze from your private deck. Soak, unwind and recharge after a day on the mtn in

Terry Hill Berkshire Hathaway HomeServices Stratton Home

65 Styles Branch Rd Unit 819, Stratton, VT 05360
/15
$18,500
- 1 Bath
- 421 Sq Ft
89 Grand Summit Way Unit 212, Dover, VT 05356

Quarter share (deeded interval 2) ownership at the Grand Summit offers 13 weeks of vacation per year on a rotating schedule that can be used, rented, or traded as you desire. This second floor (Unit 212) sleep two studio unit is 421 sq ft and has a king bed in the living area, a kitchen/dining area, and a full bath. Experience the mountain resort lifestyle affordably!! Enjoy the best ski in/out

Jennifer Hovey-Densmore Deerfield Valley Real Estate

89 Grand Summit Way Unit 212, Dover, VT 05356
/30
$750,000
- 3 Beds
- 2 Baths
- 2,198 Sq Ft
340 Melendy Hill Rd, Londonderry, VT 05155

340 Melendy Hill Road, South Londonderry, VT40 Acres | 3 Beds | 2 Baths | Expansive Barn | Mountain ViewsTucked away in the hills of South Londonderry, this charming three-bedroom, two-bath cabin offers the perfect balance of privacy, natural beauty, and quintessential Vermont living. Sited on 40 peaceful acres with sweeping mountain views, the property feels like a private

Bob Maisey Berkshire Hathaway HomeServices Stratton Home

340 Melendy Hill Rd, Londonderry, VT 05155

Showing Results 121 - 160, Page 4 of 11

Vermont Windham County

How to Buy a Home How to Finance a Home How to Sell a Home

Windham County Types of Homes for Sale

Windham County Real Estate Listings

Windham County New Construction Homes

More About Living in Windham County

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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.