Windham County VT Homes for Sale

/18
$120,000
- Land
- 2.84 Acres
- $42,254 per Acre
111 Gib Lockerby Rd, Grafton, VT 05146

Nestled in the rolling hills of southern Vermont, just minutes above the charming center of Grafton, this professionally developed parcel of land beckons you to build your Vermont dream home. This open and sunny lot, complete with its own small apple orchard is surrounded by timeless stone walls and lovely woodlands. Choose the best building site for you; the cleared front acre, formerly a

Christopher Cummings

Cummings & Co

(802) 424-8491

111 Gib Lockerby Rd, Grafton, VT 05146
/54
$142,000
- Land
- 2.19 Acres
- $64,840 per Acre
192 Pingree Park Ln, Londonderry, VT 05148

2.19 acres with 199’ waterfront bordering the west bank of pristine Utley Brook with headwaters flowing from the national forestWaterfront parcel, septic fully engineered and permitted for a 4 bedroom home. Set at the end of a quiet, dead-end lane, this is a rare gem in Londonderry. Beautiful riverfront, convenient to everything in one of Vermont’s most sought-after mountain areas. Located

Alison Cummings

Cummings & Co

(802) 416-4003

192 Pingree Park Ln, Londonderry, VT 05148
/60
$4,950,000
- 4 Beds
- 8 Baths
- 16,736 Sq Ft
1950 Collins Rd, Brattleboro, VT 05301

Exceptional 177+ Acre Estate with Luxury Log Home, Event Venue & Craft Beverage Facilities. Experience unmatched luxury and opportunity on this remarkable 177+ acre estate. Featuring an 8,000+ sq ft timber frame log home, a 7,100 sq ft finished event venue, and on-site winery, craft brewery, and champagne-making facilities, this turn-key property is ideal as a private residence, retreat, or

Margretta Fischer

Wohler Realty Group

(802) 317-7158

1950 Collins Rd, Brattleboro, VT 05301
/56
$127,000
- Land
- 2.07 Acres
- $61,353 per Acre
191 Pingree Park Ln, Londonderry, VT 05148

2.07 acres with 140’ waterfront bordering the west bank of pristine Utley Brook with headwaters flowing from the national forest. Waterfront parcel, septic fully engineered and permitted for a 4 bedroom home. Set at the end of a quiet, dead-end lane, this is a rare gem in Londonderry. Beautiful riverfront, convenient to everything in one of Vermont’s most sought-after mountain areas. Located just

Alison Cummings

Cummings & Co

(802) 613-9168

191 Pingree Park Ln, Londonderry, VT 05148
/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
/35
$2,399,000
- 4 Beds
- 4.5 Baths
- 3,569 Sq Ft
662 Howe Farm Rd, Jamaica, VT 05343

Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, adding a touch of

Andie Fusco Four Seasons Sotheby's Int'l Realty

662 Howe Farm Rd, Jamaica, VT 05343
/33
$1,760,000
- 4 Beds
- 3.5 Baths
- 2,698 Sq Ft
89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360

Trailside!!! Ski in, ski out!! The very best Ski Direct Access at Stratton!! Most popular of luxury townhomes---offering an enlarged patio with Hot Tub, Open and Sunny, Four Bedrooms plus a Den Floorplan, Single Car Garage! Fully Furnished. Hardwood Flooring, floor to ceiling stone, wood burning fireplace! Enjoy this outstanding trailside location. And as an added benefit, the Stratton Training

Edwin Kevil Stratton Real Estate

89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360
/60
$849,000
- 5 Beds
- 4.5 Baths
- 3,840 Sq Ft
42 Blackberry Ln, Jamaica, VT 05343

Welcome to "Sweet Berry Farm", a charming Vermont homestead blending 1850s character with a spacious modern addition. Set on 5.7 private acres in Jamaica, this property offers abundant natural beauty—mature apple trees, blueberry and blackberry bushes and vibrant seasonal gardens. The expanded farmhouse provides exceptional space for living and entertaining. The main floor features an open living

MaryKate Grey Stratton Real Estate

42 Blackberry Ln, Jamaica, VT 05343
/79
$275,000
- Land
- 22.32 Acres
- $12,321 per Acre
81 Parish Hill Rd Unit 26, Newfane, VT 05345

Tucked away in the quiet hills of South Newfane, Vermont, this property presents an excellent opportunity to own a secluded off-grid retreat with endless potential. Spanning 22.32 acres of mixed timberland, the land offers both natural beauty and outdoor recreation, while the cabin provides a comfortable base that is already well on its way to completion.The cabin itself measures 715 square feet

Chad Bruyette Whitetail Properties Real Estate

81 Parish Hill Rd Unit 26, Newfane, VT 05345
/12
$999,000
- Land
- 12.2 Acres
- $81,885 per Acre
Higley Hill Rd, Wilmington, VT 05363

Looking for Vermont land with privacy, natural beauty, and development potential? This 12.2-acre parcel in Windham County offers a peaceful escape tucked into the woods, ideal for buyers seeking recreational land, a homestead site, or a rural retreat. With 250 ft of road frontage on Higley Hill Rd, the property is easily accessible while still offering seclusion.The terrain is wooded and

Community Lands Community Lands

Higley Hill Rd, Wilmington, VT 05363
/26
$599,000
- 4 Beds
- 3 Baths
- 2,600 Sq Ft
10 Grouse Ln Unit 10A, Dover, VT 05356

Owners open to offers! 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

Adam Palmiter Berkley & Veller Greenwood/Dover

10 Grouse Ln Unit 10A, Dover, VT 05356
/51
$550,000
- 3 Beds
- 2 Baths
- 1,814 Sq Ft
1886 Winhall Hollow Rd, South Londonderry, VT 05155

Optimal Location, Competitively priced, Exceptional property tucked amidst nature with views toward Magic. Offering Main Residence and a large oversized detached garage/ barn with upstairs finished space and plenty of space for snow mobiles, ATVs and all your mountain vehicles and outdoor toys. Whether you're a weekend warrior looking to enjoy everything the Green Mountains have to offer or

Kim Morgan-Wohler Wohler Realty Group

1886 Winhall Hollow Rd, South Londonderry, VT 05155
/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
/41
$899,000
- 4 Beds
- 4 Baths
- 3,200 Sq Ft
9 Windham Way, Dover, VT 05356

This upgraded new style Greenspring townhome has direct views of Mount Snow and door to door shuttle service to and from the unit and the base area. A well updated 4+ bedroom, 4 bath unit with lots of bonus space, many recent updates and unique features. These include an open concept great room with vaulted ceiling, sunny exposure and sunset/ski trail views, wood burning fireplace unique against

Adam Palmiter Berkley & Veller Greenwood/Dover

9 Windham Way, Dover, VT 05356
/29
$625,000
- 5 Beds
- 2 Baths
- 2,774 Sq Ft
618 Shearer Hill Rd, Brattleboro, VT 05301

Discover the Best of Southern Vermont Living! Nestled in a bucolic country setting, this versatile property offers breathtaking views of a neighboring classic Sugar House and a large beaver pond that is the headwaters of the Green River. Whether you're seeking a serene country retreat, a dedicated ski house, or a comfortable year-round home, this classic cape checks all the boxes. The bright,

Thomas Dahlin Berkley & Veller Greenwood Country

618 Shearer Hill Rd, Brattleboro, VT 05301
/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
/26
$629,000
- 3 Beds
- 3 Baths
- 2,170 Sq Ft
14 Johnson Hill Rd, Dover, VT 05356

Unique contemporary chalet just a short drive from the Mount Snow Ski Resort and village Wilmington, and with direct snowmobile trail access. This very cool open concept home has been completely renovated and upgraded, and sits on a on a private lot in the Dover Hills with beautiful lawn space and cul de sac driveway. Walk in through the spacious mudroom with plenty of room for gear, and head up

Adam Palmiter Berkley & Veller Greenwood/Dover

14 Johnson Hill Rd, Dover, VT 05356
/35
$899,900
- 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
/37
$730,000
- 5 Beds
- 3 Baths
- 2,635 Sq Ft
341 Under the Mountain Rd, Londonderry, VT 05148

Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly

Andy Reed Four Seasons Sotheby's Int'l Realty

341 Under the Mountain Rd, Londonderry, VT 05148
/60
$650,000
- 4 Beds
- 4 Baths
- 2,978 Sq Ft
23 Brook Rd, Saxtons River, VT 05154

Includes 1-Year Home Warranty. A Distinctive Country Retreat on 6.8± private acres in the heart of the historic village of Saxtons River. This idyllic country estate offers year-round views, exquisite perennial gardens, & two beautifully integrated wings—the timeless Cape & the charming Carriage House. Inside of the Cape wing is a sunlit eat-in kitchen, KraftMaid cherry cabinetry & Silestone

Isabella Luhrs BHG Masiello Keene

23 Brook Rd, Saxtons River, VT 05154
/60
$549,000
- 2 Beds
- 2 Baths
- 850 Sq Ft
794 White Rd, Windham, VT 05359

Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out—new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam

Erica Reynolds Southern Vermont Realty Group

794 White Rd, Windham, VT 05359
/29
$569,000
- 4 Beds
- 3 Baths
- 2,050 Sq Ft
39B Kingswood Rd, Dover, VT 05356

An impeccably maintained, beautifully furnished, and recently painted Kingswood townhome is conveniently located just minutes from Mount Snow and the Hermitage Club. This townhome features four bedrooms; an open-concept living area on the main level; a kitchen with a large island, granite countertops, and a vaulted ceiling; a wood-burning fireplace; and sliding doors leading to a private deck

Patricia Fitzpatrick Skihome Realty

39B Kingswood Rd, Dover, VT 05356
/30
$698,000
- 4 Beds
- 3 Baths
- 2,600 Sq Ft
10 Grouse Ln, Dover, VT 05356

Welcome to your perfect Vermont getaway! This spacious 4 bedroom, 3 bathroom townhome is ideally located adjacent to the Mount Snow Golf Course, offering year-round enjoyment. Just a short drive to both Mount Snow and The Hermitage Club, you'll have easy access skiing, golfing, dining, and all that Southern Vermont has to offer.Step inside to find a warm and inviting interior, highlighted by

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

10 Grouse Ln, Dover, VT 05356
/32
$675,000
- 3 Beds
- 3 Baths
- 2,216 Sq Ft
12 Three Streams Way, Wilmington, VT 05363

Beautiful 2006 chalet in the Chimney Hill community just a short drive from the Mount Snow Ski Resort and village Wilmington. This meticulous turn key home has been completely renovated and upgraded, and sits on a on a private lot in the Chimney Hill community on a quiet side road with access to snowmobile trails and winter views. Inside is a gorgeous great room space with vaulted ceilings and

Tamara Purcell Berkley & Veller Greenwood Country

12 Three Streams Way, Wilmington, VT 05363
/43
$625,000
- 5 Beds
- 3 Baths
- 2,600 Sq Ft
15 Bills Rd, West Wardsboro, VT 05360

This spacious five-bedroom, three-bath Cape-style home offers a wonderful Vermont retreat, ideally located just minutes from the Stratton Mountain Resort Sun Bowl and the scenic Grout Pond Recreation Area, and only about 10 minutes from Mount Snow Resort. With immediate access to nearby snowmobile trails, it’s perfectly suited for year-round outdoor enthusiasts. Nicely landscaped yard with

Jennifer Hovey-Densmore Deerfield Valley Real Estate

15 Bills Rd, West Wardsboro, VT 05360
/50
$565,000
- 3 Beds
- 2 Baths
- 1,944 Sq Ft
3148 Route 11, Londonderry, VT 05148

Looking for a piece of Vermont to call your own? Look no further then this beautiful home looking for new owners to love and enjoy it like the current owners have. Perfectly situated in Londonderry, Vermont near Bromley, Stratton, Okemo, and Magic Mountains. The sellers have done updates to the home and property but have left spots for the new owners to still put their own finishing touches on

Erin Kendall EXP Realty

3148 Route 11, Londonderry, VT 05148
/26
$625,000
- 3 Beds
- 2 Baths
- 2,360 Sq Ft
68 Ellis Brook Rd, Dover, VT 05341

Gorgeous updated chalet on a private 2-acre parcel with mountain views and easy access to Mount Snow. Nestled in the desirable Dover Hills, this charming country retreat offers privacy befitting a year-round getaway, yet is just a short drive to the Mount Snow ski resort. Ample parking off a paved road, generous lawn space for play or pets, a garden shed, and excellent sun exposure complete the

Adam Palmiter Berkley & Veller Greenwood/Dover

68 Ellis Brook Rd, Dover, VT 05341
/32
$549,000
- 4 Beds
- 2 Baths
- 1,617 Sq Ft
13 Yodeling Ln, Dover, VT 05356

Tremendous opportunity to own an updated A-frame chalet at the base of Mount Snow ski resort and the Carinthia Freestyle Terrain Park. This lovely Vermont home sits nestled on a quiet loop just south of the mountain, with direct walking and hiking trail access.The open floor plan features an updated kitchen with stainless appliances, copper counters, and a vent hood, along with a living room

Adam Palmiter Berkley & Veller Greenwood/Dover

13 Yodeling Ln, Dover, VT 05356
/60
$599,000
- 5 Beds
- 2.5 Baths
- 3,000 Sq Ft
673 Vermont 121, Grafton, VT 05146

Historic Charmer, this c. 1830 farmhouse has been loved and stewarded by its current owners for half a century. It is time to pass this amazing vintage home on to another lucky family. The house has original features including 2 fireplaces, curved plaster walls and beautiful honey colored wide pine floors. The first floor offers an eat-in- kitchen, formal dining room, spacious sunny living room

Janet Lucier Barrett & Valley Assoc. Inc

673 Vermont 121, Grafton, VT 05146
/23
$649,000
- 3 Beds
- 2.5 Baths
- 1,874 Sq Ft
457 Ray Hill Rd, Wilmington, VT 05363

Owners will consider reasonable offers. Lovely expanded farmhouse just up from the village of Wilmington and with mountain views and gorgeous exposure on 2.7 acres of private open land. This charming home is just a short drive to both the Mount Snow and Hermitage Club ski resorts, and nearby lakes, with easy access despite it's private location. The home sits on a pastoral lot with gorgeous

Adam Palmiter Berkley & Veller Greenwood/Dover

457 Ray Hill Rd, Wilmington, VT 05363
/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
/39
$575,000
- 3 Beds
- 2 Baths
- 1,957 Sq Ft
256 Potter Rd, Wardsboro, VT 05355

Built with a decade of love and care, this custom 3-bedroom, 2-bath hybrid timber frame home showcases quality craftsmanship and a deep connection to nature. Designed with natural materials to harmonize with the surrounding landscape, this inviting home offers peace and comfort both inside and out. Fall asleep to the soothing sound of the river that flows the length of the property. The main

Jennifer Hovey-Densmore Deerfield Valley Real Estate

256 Potter Rd, Wardsboro, VT 05355
/32
$559,000
- 3 Beds
- 3 Baths
- 2,080 Sq Ft
9 Greer Ct, Wilmington, VT 05363

Charming 2007 home with recent renovations nestled in the Chimney Hill community just a short drive from the Mount Snow ski resort, country village of Wilmington, and nearby lakes and amenities. This home sits on a private dead end parcel and has unique privacy and curb appeal. Inside you are treated to a large vaulted great room with expansive windows, exposed natural wood ceilings, and great

Adam Palmiter Berkley & Veller Greenwood/Dover

9 Greer Ct, Wilmington, VT 05363
/60
$549,000
- 2 Beds
- 2 Baths
- 2,016 Sq Ft
35 Upper Bartonsville Rd, Chester, VT 05143

Looking for a turn key Vermont retreat to call your own? This beautiful home built in 2009 and complete with a newer barn, chicken coop, treehouse, and storage shed could be what you have been dreaming of. Conveniently located just a short drive to 91, not far to the Vast trail access for snowmobiling, and near to many Vermont mountains for skiing or snowboarding. The warm and welcoming home

Erin Kendall EXP Realty

35 Upper Bartonsville Rd, Chester, VT 05143
/48
$644,000
- 3 Beds
- 2.5 Baths
- 2,329 Sq Ft
774 Stratton Arlington Rd, Stratton, VT 05360

Charming Log Cabin Compound Near Stratton and Mount SnowEscape to this quintessential Vermont retreat nestled on 1.2 private acres just minutes from Grout Pond, the Green Mountain National Forest, and a short drive to both Stratton and Mount Snow Resorts.The main log home offers three bedrooms and two baths with a warm, inviting open-concept living space. A stone fireplace anchors the

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

774 Stratton Arlington Rd, Stratton, VT 05360
/21
$489,000
- 3 Beds
- 2 Baths
- 2,003 Sq Ft
12 Lilla Ln, Wilmington, VT 05363

Beautiful woodsy contemporary chalet located just down from the Chimney Hill Clubhouse in Wilmington. This charming home has nearby access to the country village of Wilmington, Lake Whitingham, is a short drive to the Mt Snow ski resort, and has nearby to one of the best hiking areas in Southern Vermont, thanks to the community adjacent Green Mountain National Forest. It sits nestled on a private

Adam Palmiter Berkley & Veller Greenwood/Dover

12 Lilla Ln, Wilmington, VT 05363
/31
$1,750,000
- 4 Beds
- 3.5 Baths
- 2,698 Sq Ft
148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360

148B Sun Bowl Ridge Rd., Stratton Mountain, VT 05155, Solstice 148B Ski in, ski out directly from your private garage on a Stratton ski trail that has full snowmaking coverage. This home is in one of the most exclusive trailside communities in all of the Northeast! It has an open and sunny floorplan with large windows and a sliding glass door to the private patio with fire pit and hot tub.

Andrew King Stratton Real Estate

148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360
/15
$67,500
- Land
- 3.5 Acres
- $19,286 per Acre
0 Dover Rd Unit 5054979, Newfane, VT 05345

Welcome to your future home in the heart of a picturesque Vermont village! These exquisite land lots, thoughtfully designed by the architect-owner, offer a unique opportunity to build your dream home in a setting that perfectly captures the quintessential charm of small-town Vermont. Each lot is meticulously planned to adhere to the timeless "Vermont Vernacular" style, ensuring that your new home

Keith Nowak Four Seasons Sotheby's Int'l Realty

0 Dover Rd Unit 5054979, Newfane, VT 05345
/46
$495,000
- 4 Beds
- 2.5 Baths
- 2,756 Sq Ft
214 Putney Rd, Brattleboro, VT 05301

Step back in time and discover the enchanting potential of this distinguished 1940 Colonial, perfectly positioned to capture the spirit of Brattleboro. Perched on a generous 0.79-acre level lot, this home offers a rare blend of expansive personal space and convenient in-town living. From the moment you arrive, the classic lines, wood siding, and enduring slate roof hint at the craftsmanship of a

Keith Nowak Four Seasons Sotheby's Int'l Realty

214 Putney Rd, Brattleboro, VT 05301
/30
$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

Showing Results 1 - 40, Page 1 of 9

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