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
/22
$850,000
- Land
- 67 Acres
- $12,687 per Acre
00 S Pine Banks Rd, Putney, VT 05346

Unleash the potential of this exceptional 60+ acre Vermont property, a rare offering brimming with diverse landscapes and endless possibilities. A well-maintained gravel driveway leads you into the heart of the land, complete with readily available power. Discover multiple potential building sites, each offering breathtaking views or secluded privacy, tailored to your preference. A charming

Ross Doody

Century 21 Highview Realty

(802) 499-2391

00 S Pine Banks Rd, Putney, VT 05346
/34
$369,000
- 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
/43
$565,000
- 4 Beds
- 2.5 Baths
- 2,149 Sq Ft
66 Hilltop Rd, Londonderry, VT 05155

This great home is a must see! Fully renovated in the past 8 months, from floor to ceilings, every inch has been updated. Brand new kitchen and baths, all new fixtures and appliances, this 4 bedroom 3 bath home is waiting for new owners to enjoy it! Great proximity to skiing, recreation, groceries and dining, yet private and set back from the road. Sold furnished with a pleasing neutral palate,

Alison Cummings

Cummings & Co

(802) 553-3290

66 Hilltop Rd, Londonderry, VT 05155
/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
/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
/36
$210,000
- Land
- 30.1 Acres
- $6,977 per Acre
184 Schoolhouse Rd, Jamaica, VT 05343

Jamaica, Vermont's hidden gem! Experience this wonderful 30.1+/- acre forested parcel with views of the local mountains. The land gently slopes to the southeast, perfect for solar, but better yet, utility lines are located along much of the frontage! Bounded on two sides by classic stone walls, there is a woods road that travels through the property making exploration easy. Jamaica has NO local

Curtis Trousdale

184 Schoolhouse Rd, Jamaica, VT 05343
/8
$275,000
- Land
- 34.53 Acres
- $7,964 per Acre
0 W Hill Rd, Jamaica, VT 05343

The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 3 is 34.53 acres, and is mostly forested near the access road. A driveway would need to be

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/11
$495,000
- Land
- 68.89 Acres
- $7,185 per Acre
0 W Hill Rd, Jamaica, VT 05343

The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 4 is 68.89 acres and is the largest of the five parcels for sale. This lot has a solid woods

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/7
$195,000
- Land
- 15.27 Acres
- $12,770 per Acre
0 W Hill Rd, Jamaica, VT 05343

The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 2 is 15.27 acres and is the first parcel found on the left side of the newly built 20 foot

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/15
$650,000
- Land
- 51.93 Acres
- $12,517 per Acre
0 W Hill Rd, Jamaica, VT 05343

The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 5 is 51.93 acres and is located at the top of the subdivision. This parcel is very unique, and

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/37
$874,000
- 6 Beds
- 3 Baths
- 2,900 Sq Ft
261 Handle Rd, Dover, VT 05356

Slopeside 6 Bedroom Ski Chalet at Carinthia Base, Mount Snow This ski chalet is perfectly positioned at the base of Carinthia, offering true slopeside access and unmatched convenience. Step out your door and onto the trails, with the Carinthia Base Lodge, terrain parks, lifts, and all the action of the mountain just steps away. Inside, the home blends classic chalet character with thoughtful

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

261 Handle Rd, Dover, VT 05356
/25
$349,000
- 2 Beds
- 2 Baths
- 1,012 Sq Ft
337 Handle Rd Unit Pines K, West Dover, VT 05356

Welcome to this beautifully updated two bedroom, two-bathroom condo in the desirable upper Snow Tree community. The home is perfectly positioned to capture incredible mountain views and the true essence of Mount Snow base area living. Step inside to find a bright, inviting interior featuring new efficient windows, a cozy gas fireplace, and beautiful cathedral ceiling that enhances the spacious

Melissa Ellis Southern Vermont Realty Group

337 Handle Rd Unit Pines K, West Dover, VT 05356
/42
$574,900
- 3 Beds
- 2 Baths
- 1,850 Sq Ft
555 Vermont 9, Wilmington, VT 05363

Welcome to your dream home in the heart of Southern Vermont. This brand-new construction 3-bedroom, 2-bath residence seamlessly blends modern comfort with classic Vermont charm, perfect for year-round living or a weekend escape. Enjoy a spacious, open-concept layout filled with natural light, enhanced by high-quality Anderson windows and doors. The kitchen boasts brand new appliances, while the

Flex Realty Group Flex Realty

555 Vermont 9, Wilmington, VT 05363
/43
$619,900
- 3 Beds
- 3.5 Baths
- 2,250 Sq Ft
883 Smead Rd, Wardsboro, VT 05355

Enjoy Vermont living in this bright and inviting 3-bedroom, 4-bathroom home, ideally located 7 minutes from Mount Snow and just under 20 minutes from Stratton. The open-concept kitchen (completely renovated in 2021) and dining area are perfect for gatherings, with natural light enhancing the home’s warm and welcoming feel.A new heating system for efficient year-round comfort is complemented by a

Samantha Decker Deerfield Valley Real Estate

883 Smead Rd, Wardsboro, VT 05355
/41
$799,000
- 5 Beds
- 3 Baths
- 3,091 Sq Ft
798 Vermont Route 100, Wilmington, VT 05363

Multi-Family & Commercial Opportunity in Wilmington, VermontSet on 1.05 acres just outside Wilmington village, this versatile property offers two recently renovated apartments totaling five bedrooms, each with its own two-car garage perfect for owner occupancy, rental income, or staff housing.The main building features updated interiors with modern kitchens, stylish baths, and new

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

798 Vermont Route 100, Wilmington, VT 05363
/39
$312,000
- 2 Beds
- 2 Baths
- 860 Sq Ft
15 Mountain Village Unit 234, West Dover, VT 05356

Welcome to your mountain getaway! This 2-bedroom, 2-bath condo is perfectly situated at the base of Mount Snow. Enjoy your morning coffee or après-ski beverage on the private balcony while taking in the mountain air and breath taking views. Cozy up by the wood-burning fireplace, perfect for relaxing after a day on the mountain. Recent updates include new windows, slider doors, balcony, flooring

Jillian Wimmelman Deerfield Valley Real Estate

15 Mountain Village Unit 234, West Dover, VT 05356
/31
$735,000
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155

Nestled right on the slopes of Stratton Mountain Resort, this two bedroom two ensuite bathroom condominium offers true ski-in/ski-out convenience for your winter getaway. You'll find yourself just steps from the Villager chairlift, beginner ski area as well as a stone's throw to the shops and restaurants in the Stratton Village. An open-concept living/dinning/kitchen area that features a stone

Timothy Mich Doddridge Stratton Real Estate

778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155
/44
$599,000
- 4 Beds
- 4 Baths
- 4,060 Sq Ft
141 Piney Brook Way, Brattleboro, VT 05301

Set on 12 acres of wooded privacy in desirable Marlboro, this spacious and versatile property offers comfort, flexibility, and stunning natural surroundings. The main home features 3 bedrooms, a large family room and first-floor laundry, offering plenty of room for a growing household, guests, or multi-generational living. Cozy up by the wood stove on chilly evenings, and enjoy the peace of mind

Desiree Stango Berkley & Veller Greenwood Country

141 Piney Brook Way, Brattleboro, VT 05301
/40
$625,000
- 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
/51
$585,000
- 3 Beds
- 2 Baths
- 1,814 Sq Ft
1886 Winhall Hollow Rd, South Londonderry, VT 05155

Exceptional property tucked amidst nature with views toward Magic. Whether you're a weekend warrior looking to enjoy everything the Green Mountains have to offer or looking for a year round residence with great schools, this property offers an optimal location- convenient to Stratton, Bromley and Magic Mountains as well as Burr and Burton Academy and Floodbrook School. Gourmet kitchen with gas

Kim Morgan-Wohler Wohler Realty Group

1886 Winhall Hollow Rd, South Londonderry, VT 05155
/35
$579,000
- 4 Beds
- 1 Bath
- 1,560 Sq Ft
104 Karen Day Rd, Halifax, VT 05342

1860's Colonial/Farmhouse situated on nearly 37 acres of gorgeous land. This location, exposure, access and overall site characteristics is truly one of a kind. Ultimate privacy due to the town-maintained road (Karen Day Road) running from Larrabee Road all the way to the house and compound with no other houses along the road or in sight whatsoever. The land is remarkable with level open fields,

Chris Long BHG Masiello Brattleboro

104 Karen Day Rd, Halifax, VT 05342
/45
$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
/60
$645,000
- 3 Beds
- 3.5 Baths
- 2,472 Sq Ft
38 Greenspring Rd, Dover, VT 05356

Welcome to Greensprings one of Mount Snow’s most sought-after communities offering the perfect blend of mountain convenience and Vermont charm. This spacious 3 bedroom, 4 bath townhome features stunning mountain views and an inviting open-concept living area with vaulted wood ceilings, a dramatic wall of windows, and a floor-to-ceiling wood-burning fireplace.The main level is ideal for

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

38 Greenspring Rd, Dover, VT 05356
/38
$639,000
- 3 Beds
- 2.5 Baths
- 3,113 Sq Ft
1382 Grassy Brook Rd, Brookline, VT 05345

Beautiful Brookline! Lovingly developed by the current owners over the past 40 years, this remarkable property offers a rare opportunity—ideal for a builder, contractor, skier, snowmobiler, or anyone seeking space for equipment storage. Arrive by crossing a charming stream and following a gentle rise to the main home, which includes a one-car attached garage in the basement. Inside, the finished

Thomas Dahlin Berkley & Veller Greenwood Country

1382 Grassy Brook Rd, Brookline, VT 05345
/29
$649,000
- 5 Beds
- 3.5 Baths
- 2,706 Sq Ft
916 Wiswall Hill Rd, Townshend, VT 05353

Escape to the peace and beauty of Townshend, Vermont, where this spacious 5-bedroom home offers the perfect blend of privacy, comfort, and craftsmanship. Located on a publicly maintained dead-end road, the property enjoys a quiet, secluded country setting while still providing the reassurance of year-round access. Thoughtfully designed and well-built, the home welcomes you with warmth and

Mike Masters Four Seasons Sotheby's Int'l Realty

916 Wiswall Hill Rd, Townshend, VT 05353
/32
$560,000
- 2 Beds
- 2 Baths
- 1,775 Sq Ft
162 Buttonwood Dr, Brattleboro, VT 05301

BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

Dan Normandeau Berkley & Veller Greenwood Country

162 Buttonwood Dr, Brattleboro, VT 05301
/34
$585,000
- 2 Beds
- 2 Baths
- 1,775 Sq Ft
24 Dogwood Dr, Brattleboro, VT 05301

BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

Dan Normandeau Berkley & Veller Greenwood Country

24 Dogwood Dr, Brattleboro, VT 05301
/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

Adam Palmiter Berkley & Veller Greenwood/Dover

12 Three Streams Way, Wilmington, VT 05363
/32
$585,000
- 2 Beds
- 2 Baths
- 1,775 Sq Ft
161 Buttonwood Dr, Brattleboro, VT 05301

BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

Dan Normandeau Berkley & Veller Greenwood Country

161 Buttonwood Dr, Brattleboro, VT 05301
/39
$625,000
- 5 Beds
- 4 Baths
- 3,748 Sq Ft
58 Oak St, Brattleboro, VT 05301

Come experience the elegance and charm of this stunning in-town retreat! Close to the town common and vibrant downtown Brattleboro—home to fine dining, galleries, quaint shops, and live music venues. Step inside the main house and be welcomed by a country kitchen featuring a large island, ideal for gatherings. The home exudes Victorian character with soaring ceilings, hardwood floors, and

Rebecca Seymour Brattleboro Area Realty

58 Oak St, Brattleboro, VT 05301
/60
$579,000
- 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
/43
$599,000
- 3 Beds
- 2.5 Baths
- 2,720 Sq Ft
58 Buckboard Dr, Dover, VT 05356

58 Buckboard | Dover, VermontSet on 1.46 private acres with sweeping mountain views, this beautifully updated 3 bedroom, 3 bath home offers a perfect blend of modern style and Vermont warmth.Inside, the heart of the home is the newly renovated kitchen, featuring a center island with quartz countertops, stainless steel appliances, and open shelving. The kitchen flows seamlessly into the

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

58 Buckboard Dr, Dover, VT 05356
/26
$649,000
- 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
/49
$695,000
- 4 Beds
- 2.5 Baths
- 3,104 Sq Ft
153 Westminster Rd, Putney, VT 05346

Combining the charm of an 1820's fully restored historic home, with a 1,600 sq. ft. addition (built in 2016), this fabulous property, close to the Putney Village, offers the best of both worlds. Wide pine flooring and exposed beams in the restored front half blend beautifully with the newly built addition, featuring 9’ ceilings, hardwood floors and a handsome stone fireplace. The expansive

Heidi Bernier Berkley & Veller Greenwood Country

153 Westminster Rd, Putney, VT 05346
/59
$599,000
- 3 Beds
- 2.5 Baths
- 2,782 Sq Ft
628 Townshend Rd, Grafton, VT 05146

One of only two stone houses in the charming town of Grafton, this stately home is a truly special opportunity. Perched on a hill across from the renowned Grafton Cheese Company, the property offers easy access to village amenities and year-round recreation at Grafton Ponds Outdoor Center. Inside, you'll find a spacious and inviting layout: Large front living room with exposed beams, a beautiful

Jessica Landers Barrett and Valley Associates Inc.

628 Townshend Rd, Grafton, VT 05146
/3
$60,000
- Land
- 1.1 Acres
- $54,545 per Acre
63 Villager Loop, Dover, VT 05356

Lovely wooded building site not far from the Mount Snow ski resort, nearby lakes, villages, shopping, and dining. View potential and easy access off a paved road, with a large corner lot location, looking to the west over the ski mountains and sunsets.

Adam Palmiter Berkley & Veller Greenwood/Dover

63 Villager Loop, Dover, VT 05356
/40
$389,000
- 3 Beds
- 2.5 Baths
- 2,146 Sq Ft
49 Whitetail Dr, Vernon, VT 05354

Welcome to this very special neighborhood and home, still owned and loved by the original owners. Enter through an oversized two-car garage into a lovely tile foyer and a half bath. The open concept is warm and inviting with an efficient pellet stove. The Dining area has a slider out to an impressive 12x32-foot deck overlooking a nice combination of a level lawn and woods. For the past 20 years

Kristen Ziter Taylor Brattleboro Area Realty

49 Whitetail Dr, Vernon, VT 05354
/38
$475,000
- Land
- 133.1 Acres
- $3,569 per Acre
40 E Putney Brook Rd, Putney, VT 05346

Awesome 133± Acre Country Parcel in Putney, Vermont. A rare opportunity to own 133± acres of picturesque Vermont land in highly desirable Putney. This large country parcel offers multiple access points, including generous frontage on a major road as well as two unpaved roads. Existing logging roads weave through the property, leading to several clearings ideal for building, recreation, or

Geralyn Donohue Engel & Völkers Okemo

40 E Putney Brook Rd, Putney, VT 05346

Showing Results 1 - 40, Page 1 of 11

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