Windham County VT Homes for Sale

/44
$375,000 Open Sun 2PM - 3:30PM
- 4 Beds
- 2.5 Baths
- 2,132 Sq Ft
156 Sherwood Cir, Brattleboro, VT 05301

YOU CAN GET THERE FROM HERE! NEW ENGLAND CHARM AND FLEXIBLE SPACES...YOUR LUSH RETREAT AWAITS! A short drive to the cultural and foodie hub of southeastern Vermont, this slice of heaven is where your dreams take root. Follow a scenic road to a vibrant green lot where a terraced rock wall dotted with ferns and hostas signals your arrival. A large covered porch invites you to pull up a chair,

Fine Homes Group International Keller Williams Realty-Metropolitan

156 Sherwood Cir, Brattleboro, VT 05301
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/59
$1,395,000
- 4 Beds
- 4 Baths
- 4,200 Sq Ft
11 Corriveau Way, Wilmington, VT 05363

Nestled in Vermont's Green Mountains, this stunning mountain home blends rustic beauty with modern luxury. Minutes from the exclusive Hermitage Club (property adjacent) in Wilmington, with private skiing, hiking, & a lifestyle enveloped in natural beauty. Built by Precision Craft Log & Timber Homes, the residence features hand-selected & hewned Idaho cedar logs & spans 4,125 square feet.

Steve Goldfarb Deerfield Valley Real Estate

11 Corriveau Way, Wilmington, VT 05363
/60
$635,000
- 3 Beds
- 2 Baths
- 3,000 Sq Ft
121 Dover Hill Rd, Dover, VT 05341

Nestled in the tranquil countryside of Vermont, this property blends an equestrian retreat, homestead and ski getaway. Set on 5 private acres with vibrant perennial gardens, and abundant raspberry canes, it offers a serene escape for all seasons. Dover is considered the gateway to Vermont’s Green Mountain National Forest, with easy access to Grout Pond, Stratton, Glastonbury and the Somerset

Nick Sicard EXP Realty

121 Dover Hill Rd, Dover, VT 05341
/41
$8,950,000
- 6 Beds
- 10 Baths
- 13,393 Sq Ft
370 Fischer Ln, Jamaica, VT 05343

Accessible, but miles from the everyday. Camp Endo’s mountain kingdom is minutes from Stratton Mtn. with a 21st century take on a mountain timberframe home, and 417+/- acres threaded with trails and ridgelines. Ski your own glades and rip the eight miles of custom-designed mountain biking terrain, or just pause to enjoy the vast views. The house reimagines a rustic lodge with classic wood, bark

Dia Jenks LandVest, Inc/Woodstock

370 Fischer Ln, Jamaica, VT 05343
/46
$210,000
- Land
- 30 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 Preferred Properties

184 Schoolhouse Rd, Jamaica, VT 05343
/37
$119,000
- Land
- 10 Acres
- $11,667 per Acre
1105 S Hill Rd, Jamaica, VT 05343

Explore this exciting wooded 10.2+/- acre lot in the desirable town of Jamaica, VT. Jamaica has NO local zoning, making for simplified development, multiple cabins, camping and more. Plenty of road frontage on a year-round town plowed and maintained road. Best of all it is paved all the way to Wardsboro eliminating the difficulties of Vermont Mud Season. Utilities are located across from the

Curtis Trousdale Preferred Properties

1105 S Hill Rd, Jamaica, VT 05343
/15
$850,000
- Land
- 52 Acres
- $16,368 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,

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/11
$665,000
- Land
- 69 Acres
- $9,653 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

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/8
$355,000
- Land
- 35 Acres
- $10,281 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
/7
$235,000
- Land
- 15 Acres
- $15,390 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
/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
/36
$539,500
- 3 Beds
- 2.5 Baths
- 1,930 Sq Ft
182 Eastman Rd, Grafton, VT 05146

Tucked away on 27 +acres this well-built retreat offers 3 bedrooms and 2.5 bathrooms. The custom crafted kitchen flows to a sunny dining room and wraps to a cozy living room with fireplace and efficient wood burning stove. A first-floor bedroom and bath, makes this open concept floor plan convenient. There is an additional 3 season bonus room which opens to a screen porch for relaxing on summer

Janet Lucier Barrett & Valley Assoc. Inc

182 Eastman Rd, Grafton, VT 05146
/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 chef’s dream kitchen

Leslie Fraser Four Seasons Sotheby's Int'l Realty

100 Mowing Way, Wilmington, VT 05363
/49
$759,000
- 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
/28
$525,000
- 2 Beds
- 2 Baths
- 1,096 Sq Ft
8 Ober Tal Dr Unit A32, Stratton, VT 05360

Located trailside at the Tamarack Lift, this two-bedroom, two-bathroom Ober Tal condo offers prime proximity to the slopes—no need to spend time driving or finding parking. Simply gear up from the comfort of your home and head straight to the lift. In the summer, you'll also have direct access to hiking, mountain biking, and seasonal events and concerts in Stratton Village. Inside, the condo

Cheyanne Pugliese

8 Ober Tal Dr Unit A32, Stratton, VT 05360
/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
/39
$599,000
- 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
$549,000
- 3 Beds
- 2.5 Baths
- 2,000 Sq Ft
2B Queen Anne's Way Unit 2B, Dover, VT 05356

Beautiful Kingswood townhouse ideally located between Mount Snow and Hermitage Club at Haystack Mountain. This Kingswood townhouse offers the perfect mountain getaway. The open-concept living area features vaulted ceiling and a stunning three-sided wood-burning fireplace with custom stone surround and wood mantle creating a warm, inviting atmosphere. Enjoy the well-appointed kitchen with center

Monique White Deerfield Valley Real Estate

2B Queen Anne's Way Unit 2B, Dover, VT 05356
/29
$625,000
- 4 Beds
- 2 Baths
- 2,437 Sq Ft
72 Colonial Ridge Rd, Dover, VT 05356

This turnkey mountain retreat is ready for you to enjoy! Nestled in the serene Dover Hills, this home is ideally located near Mount Snow, snowmobile trails, shopping, and dining. Featuring four inviting bedrooms and a game room on the lower level, there’s plenty of space for everyone to relax. Cozy up in front of the wood-burning fireplace or breathe in the fresh mountain air while soaking in the

Michelle O'Neil Deerfield Valley Real Estate

72 Colonial Ridge Rd, Dover, VT 05356
/23
$249,000
- 1 Bed
- 1 Bath
- 640 Sq Ft
9B Snow Mountain Village Unit 142, Dover, VT 05356

GORGEOUS VIEWS OF MOUNT SNOW from this bright, airy one-bedroom, top-floor, corner condo in Snow Mountain Village, just minutes to the base area! Recent updates to the building include a new roof and new skylights. The interior has been tastefully updated with wood-tone vinyl flooring, plush bedroom carpet, all new LG appliances, quartz countertop and kitchen cabinets, new bathroom vanity, new

Patricia Fitzpatrick Skihome Realty

9B Snow Mountain Village Unit 142, Dover, VT 05356
/40
$229,900
- 1 Bed
- 2 Baths
- 848 Sq Ft
11F Snow Tree Ln Unit F, Dover, VT 05356

Be in the heart of the action at the base area of Mount Snow in this light-filled 1-bedroom, 2-bath end unit in the sought-after Snowtree community. Step out your door, stroll across the bridge and parking lot, and hop on the Magic Carpet lift—no need to drive. This well-designed end unit offers extra windows for abundant natural light, a smart floor plan, generous closet space, and two cozy

Chad Lackey Deerfield Valley Real Estate

11F Snow Tree Ln Unit F, Dover, VT 05356
/26
$550,000
- 3 Beds
- 3 Baths
- 3,148 Sq Ft
672 E Orchard St, West Brattleboro, VT 05301

You can't beat this location, overlooking the Brattleboro Country Club golf course. This home was built circa 1919, and has many cool vintage features such as retro curved metal kitchen cabinets and baths. Generous rooms include a large living room with two field-stone fireplaces, a spacious family room. This is a 3 bedroom house with 3 full bathrooms, but it's really about how you configure

John Hatton Berkley & Veller Greenwood Country

672 E Orchard St, West Brattleboro, VT 05301
/34
$565,000
- 4 Beds
- 3.5 Baths
- 2,753 Sq Ft
52 View Rd, Wilmington, VT 05363

Gorgeous 2003 post and beam with mountain views and great privacy. This home is located at the end of a quiet road conveniently in the lower section of the Chimney Hill community with a double lot, easy access to Wilmington and Lake Whitingham, and just a short drive to the Mount Snow ski resort and Haystack Golf Club. Inside you are treated to exposed natural woodwork and joinery throughout the

Adam Palmiter Berkley & Veller Greenwood/Dover

52 View Rd, Wilmington, VT 05363
/51
$575,000 Open Fri 12PM - 2PM
- 3 Beds
- 2.5 Baths
- 2,494 Sq Ft
63 Cooper Hill Rd, Dover, VT 05356

Welcome to the original Cooper family homestead, a timeless treasure nestled on the highly sought-after Cooper Hill Road. This beautifully preserved antique home seamlessly blends historic character with thoughtful modern updates. A newly added composite deck with sleek cable railing is the perfect place to take in the stunning, long-range mountain views stretching over 100 miles toward NH’s Mt.

Michelle O'Neil Deerfield Valley Real Estate

63 Cooper Hill Rd, Dover, VT 05356
/39
$525,000
- 3 Beds
- 3 Baths
- 2,364 Sq Ft
408 Dover Rd, South Newfane, VT 05351

This 1790's classic colonial farmhouse offers the ideal country setting in a small New England village location. Spacious rooms provide a gracious yet relaxed environment. The first floor offers the primary bedroom and living room - each with its own propane fireplace, updated chef's kitchen, and 3/4 bath. The dining room features floor to ceiling sliding French doors leading to a large deck

David Brown Berkley & Veller Greenwood Country

408 Dover Rd, South Newfane, VT 05351
/24
$579,000
- 3 Beds
- 2.5 Baths
- 2,000 Sq Ft
16 View Rd, Wilmington, VT 05363

Great Chimney Hill vacation home in Lower B section. Super layout where kitchen, counter conversers, dining room folks and living room relaxers can choose to interact as one happy group, or maintain their own separate activities. The pellet stove fireplace & vaulted ceiling in the living room make for such a relaxing space, while the steps that lead to the large loft above provides yet another

Michael Purcell Berkley & Veller Greenwood/Dover

16 View Rd, Wilmington, VT 05363
/32
$620,000
- 6 Beds
- 4 Baths
- 3,592 Sq Ft
1375 Sheldon Hill Rd, Wardsboro, VT 05355

Stunning unique 2024 renovated chalet with rare 2+ acre parcel and easy access to both Mount Snow and Stratton. This home exudes the vibe of a true Vermont ski retreat. Inside you are treated to a large open concept great room with vaulted ceilings, natural woodwork, and great natural light throughout thanks to large windows and transoms. There is a gas fireplace with stone hearth, upscale custom

Adam Palmiter Berkley & Veller Greenwood/Dover

1375 Sheldon Hill Rd, Wardsboro, VT 05355
/24
$599,000
- 3 Beds
- 3 Baths
- 2,625 Sq Ft
282 Pams Hill Rd, Wardsboro, VT 05355

As Vermonty as you can get! Located conveniently between Mount Snow and Stratton, for easy access to skiing, shopping, lakes, and summer fun, sits this idyllic log style chalet with tremendous personal use or rental potential. The home sits on a private parcel not far from the Snow Mountain Farms amenities including indoor pool and tennis court. There is ample parking thanks to a cul de sac

Adam Palmiter Berkley & Veller Greenwood/Dover

282 Pams Hill Rd, Wardsboro, VT 05355
/59
$549,000
- 3 Beds
- 2.5 Baths
- 2,500 Sq Ft
30 Big Bend Loop, Wilmington, VT 05363

Escape to the Green Mountains in this beautifully designed 3+ bedroom home with a spacious loft, 2 bonus rooms, and three finished levels in the sought-after Chimney Hill community, fully permitted for short-term rentals with strong income history—ideal for investors or second-home buyers looking to offset costs. Step inside the custom mudroom with built-in cubbies, bench, and closets, and enter

Chad Lackey Deerfield Valley Real Estate

30 Big Bend Loop, Wilmington, VT 05363
/38
$520,000
- 3 Beds
- 3 Baths
- 2,040 Sq Ft
829 Pennel Hill Rd, Halifax, VT 05342

Spacious cabin set on 16.4 acres with stream and pond. Open main living area features hardwood floors, vaulted ceilings with skylights, exposed beams, and an efficient wood stove. Updated kitchen includes stainless steel appliances and breakfast bar seating.Main level bedroom with shared en suite bathroom featuring claw foot tub and walk-in shower. Spiral staircase leads to primary suite with

Megan Quinn Southern Vermont Realty Group

829 Pennel Hill Rd, Halifax, VT 05342
/32
$598,000
- 5 Beds
- 2 Baths
- 2,892 Sq Ft
238 Hemlock Hill Rd, Wardsboro, VT 05355

This spacious 5 bedroom home is located on a private lot in the popular Snow Mountain Farms community. The three levels offer privacy and quiet with an outdoor fire pit, garden shed, and access to the VAST snowmobile trails. Its open floor plan with vaulted ceilings and stone hearth gas fireplace is perfect for apres ski gatherings, and the large open kitchen is ready to accommodate cooking for a

Jeffrey Sheehan Cummings & Co

238 Hemlock Hill Rd, Wardsboro, VT 05355
/28
$555,000
- 6 Beds
- 3.5 Baths
- 2,766 Sq Ft
624 Boyd Hill Rd, Wilmington, VT 05363

Spacious 6-Bedroom Ski & Lake Home in Vermont – Perfect for All Seasons Escape to the beauty of Vermont in this stunning 6-bedroom, 4-bathroom retreat—perfectly situated for year-round adventure between the slopes and the lake. While you’re gathering with loved ones, this warm and welcoming home offers space, style, and all the comforts you need to relax and reconnect. Inside, enjoy a chef’s

Jason Saphire www.HomeZu.com

624 Boyd Hill Rd, Wilmington, VT 05363
/28
$195,000
- 2 Beds
- 2 Baths
- 1,098 Sq Ft
274/76Qtr.1-4 Grand Summit Way, Dover, VT 05356

FULL ownership of this sleep 10 condo comprises of two units. Unit 276 has a private bedroom with a queen bed, queen sleeper sofa and queen murphy bed in the living area. Kitchenet and a full bath with an extra large covered balcony. Adjoining room 274 has 2 king beds and a full bath. Units are located on the base area side of the hotel. Wake up to the Grand Summit Express and the Bluebird lifts

Kelly Agrillo Southern Vermont Realty Group

274/76Qtr.1-4 Grand Summit Way, Dover, VT 05356
/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
/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
/57
$350,000
- 4 Beds
- 2 Baths
- 2,472 Sq Ft
16 Pearce Cir, Bellows Falls, VT 05101

Charming Split-Level Ranch in Desirable Bellows Falls Neighborhood Set on a spacious 0.39-acre corner lot, this well-kept split-level ranch offers comfort, versatility, and great curb appeal. Mature hedges provide privacy in the backyard, creating a peaceful outdoor space. Inside, you'll find four generous bedrooms and two full baths across a thoughtful layout. A convenient

Rob Weltz Barrett & Valley Assoc. Inc

16 Pearce Cir, Bellows Falls, VT 05101
/14
$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
/56
$1,330,500
- 4 Beds
- 4.5 Baths
- 3,692 Sq Ft
225 W Jamaica Rd, Stratton, VT 05360

Perfectly situated between Mount Snow and Stratton Resort, and just a short drive to scenic Grout Pond and the National Forest, this Stratton, Vermont retreat offers the ideal balance of privacy, recreation, and comfort. Set on landscaped grounds with a tranquil pond, the main residence features four spacious bedrooms, two of which are en suite and four bathrooms. The open concept great room

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

225 W Jamaica Rd, Stratton, VT 05360
/46
$75,000
- 2 Beds
- 2 Baths
- 1,271 Sq Ft
315, Qtr 1 89 Grand Summit Way, Dover, VT 05356

Enjoy all the perks of slope-side living with no upkeep in this unique top-floor 2-bedroom, 2-bathroom quarter share suite at the Grand Summit Resort Hotel. This spacious condo is just one level below the penthouse, sleeps up to 10 people, and features a full kitchen, gas fireplace, and private deck with stunning views overlooking the ski slopes.The large primary suite offers a peaceful

Patricia Fitzpatrick Skihome Realty

315, Qtr 1 89 Grand Summit Way, Dover, VT 05356
/37
$699,000
- 3 Beds
- 3 Baths
- 1,400 Sq Ft
5Q Northbrook Village Rd Unit A33, Dover, VT 05356

One of a kind opportunity to be trailside at Mount Snow. This is a lofted 3 bedroom, 3 bath unit, and is one of the closest buildings at Seasons to the newly renovated amenities, meaning you can go to the pools, gym, hot tubs, and more, without having to get in your car on days when you take a break from skiing. Enjoy the large vaulted living space with stone floor to ceiling wood burning

Adam Palmiter Berkley & Veller Greenwood/Dover

5Q Northbrook Village Rd Unit A33, 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.