Windham County VT Homes for Sale

/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
/42
$499,000
- 4 Beds
- 2.5 Baths
- 1,986 Sq Ft
168 Howard Rd, Jamaica, VT 05343

This loving home has seen many years of enjoyment from its current owners. Four bedrooms, two and a half baths, large open kitchen dining area with a beautiful granite island to gather around. Separate living room space with beautiful stone fireplace and half bath all on the main floor. The four bedrooms with a lovely large primary suite with private bath, cathedral ceilings will be the perfect

Julie Lowe Lowe's Real Estate, LLC

168 Howard Rd, Jamaica, VT 05343
/26
$500,000
- 4 Baths
- 5,140 Sq Ft
18 Bridge St, Town of Rockingham, VT 05101

COMMERCIAL OR RESIDENTIAL: The Bellows Falls Times Building, constructed in 1932 for the Vermont Newspaper Corporation, stands proudly at the corner of Bridge and Island Streets in downtown Bellows Falls, Vermont. This three-part complex—comprising the main brick newspaper plant, an adjoining warehouse, and a former garage—occupies a compact 0.13-acre lot along the canal fringe Equipped with

Rob Weltz Barrett & Valley Assoc. Inc

18 Bridge St, Town of Rockingham, VT 05101
/60
$729,000
- 3 Beds
- 2 Baths
- 2,731 Sq Ft
49 Tyler St, Brattleboro, VT 05301

Rare opportunity to own this iconic Queen-Anne Victorian in Brattleboro’s coveted Tyler Street neighborhood. A remarkable and extremely rare blend of country and in-town living. Extraordinary and stunning views of the Connecticut River & Mount Wantastiquet. Lovingly cared for by the same owner for the past 29 yrs. This home sits proudly on the expansive 0.85-acre corner lot, in the core of

Dan Normandeau Berkley & Veller Greenwood Country

49 Tyler St, Brattleboro, VT 05301
/33
$235,000 Open Mon 1PM - 3PM
- 2 Beds
- 2.5 Baths
- 2,112 Sq Ft
116 Morningside Commons, Brattleboro, VT 05301

Yes! A coveted first floor single level unit! And not only that but an end unit, sweetly tucked away for privacy! Just follow the tree and flower lined path right to your door!2 bedrooms, one ensuite, with an additional bedroom, bath, large eat in kitchen, living room, and a stackable washer/dryer, all on the first floor! There are only a few condos here that have finished basement space and this

Rebecca Seymour Brattleboro Area Realty

116 Morningside Commons, Brattleboro, VT 05301
/51
$949,000
- 5 Beds
- 8 Baths
- 7,430 Sq Ft
925 Hinesburg Rd, Brattleboro, VT 05301

Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

Christine Lewis Brattleboro Area Realty

925 Hinesburg Rd, 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
- 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
/54
$645,000 Open Sat 11AM - 1PM
- 4 Beds
- 3 Baths
- 2,416 Sq Ft
22 Hillside Dr, Wilmington, VT 05363

This reimagined 1970s ski chalet blends timeless architecture with cutting-edge design, offering 4 bedrooms and 3 bathrooms across nearly 4 private acres. Thoughtfully curated for both personal enjoyment and short-term rental potential, the home is turnkey-ready—just bring your suitcase.The entry level features two ensuite bedrooms, each with fully renovated baths, and a spacious lounge

Lauren Niles Coldwell Banker LIFESTYLES - Quechee

22 Hillside Dr, Wilmington, VT 05363
/26
$497,500
- 4 Beds
- 3 Baths
- 1,776 Sq Ft
28 Country Club Rd, Dover, VT 05356

Beautifully updated and rustic chalet just south of Mount Snow and near the Mount Snow golf course and Valley Trail. This home sits on a wooded private lot but with amazing convenience just up from a MOOver shuttle drop off location, on a paved road, with easy access to nearby trails. Just about everything has been updated to make this a turn key property, and ready for immediate enjoyment.

Adam Palmiter Berkley & Veller Greenwood/Dover

28 Country Club Rd, Dover, VT 05356
/39
$525,000 Open House 6/22
- 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
/57
$859,000
- 3 Beds
- 3.5 Baths
- 3,212 Sq Ft
104 Juniper Ridge Rd, Brattleboro, VT 05301

Welcome to Juniper Ridge! Where you will find superior craftsmanship, a private haven, and neighbors only one can dream of. As you enter the foyer of this custom built home, you'll feel its character & elegance with vaulted ceilings, arched doorways, terracotta tile and balconies lined with bookshelves. The home was built with attention to the flow, energy and natural light. The kitchen has

Kristen Ziter Taylor Brattleboro Area Realty

104 Juniper Ridge Rd, Brattleboro, VT 05301
/60
$995,000
- 3 Beds
- 3 Baths
- 2,258 Sq Ft
266 Ursa Ridge Rd, Dummerston, VT 05301

Homes surrounded by nature's tranquility are plentiful. However, this fabulous, 51+/- acre property is enveloped within an additional 100 acres of deeded building-restricted land. Serenity, never to be threatened, is your guarantee. Cedar, pine, maple, walnut, beech, hickory, birch and oak are featured throughout this home. The owner-builder inter-laced timbers from the land to create a

Randi Ziter Brattleboro Area Realty

266 Ursa Ridge Rd, Dummerston, VT 05301
/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
/59
$547,000
- 5 Beds
- 4.5 Baths
- 5,850 Sq Ft
628 S Main St, Brattleboro, VT 05301

Absolutely Gorgeous In-Town Home with Exceptional Attention to Detail.This stunning residence offers over 5,000 square feet of meticulously designed living space in the main house, plus a fully separate accessory dwelling with two independent living areas—ideal for extended family, guests, or producing income. Additionally there is a two-car garage with an integrated service pit for convenient

Kerry Mulverhill Brattleboro Area Realty

628 S Main St, Brattleboro, VT 05301
/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
/41
$560,000
- 4 Beds
- 2 Baths
- 2,450 Sq Ft
441 Guilford St, Brattleboro, VT 05301

Perched proudly on a knoll, this mid-19th-century colonial was one of two farmsteads in this neighborhood of Brattleboro, VT. This stunning, 4-BR, 2-BA hip roof colonial & spacious, 2-story barn have been lovingly cared for by the same owner for 56 years! Now is your opportunity to own a New England classic in a neighborhood setting, but country feel - all w/in very close proximity to town

Dan Normandeau Berkley & Veller Greenwood Country

441 Guilford St, Brattleboro, VT 05301
/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
/58
$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 aprés 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
/29
$549,000
- 3 Beds
- 2.5 Baths
- 1,620 Sq Ft
176 Pratt Bridge Rd, Jamaica, VT 05343

Meticulously maintained and in pristine condition, this exceptional home has been lovingly cared for by the same family for over 50 years. Set back on a level, tree-lined lot on a quiet dead-end road, the home offers serenity and privacy while still being just a short drive to Stratton Mountain. Oversized windows throughout flood the interior with natural light, highlighting the soaring cathedral

Carrie Mathews Winhall Real Estate

176 Pratt Bridge Rd, Jamaica, VT 05343
/28
$599,000
- 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 purchase

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

8577 Vermont 30 Unit H, Jamaica, VT 05343
/17
$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
/24
$26,500
- 1 Bed
- 2 Baths
- 840 Sq Ft
89 236 Qtr. 2 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

89 236 Qtr. 2 Grand Summit Way, Dover, VT 05356
/29
$290,000
- 3 Beds
- 1 Bath
- 1,392 Sq Ft
403 Tyler Hill Rd, Vernon, VT 05354

Welcome to this sweet and inviting 3-bedroom, 1-bath home, beautifully updated around 2015 and ready for new memories! Nestled on a generous lot, this home offers both comfort and functionality with a bright, open layout and thoughtful improvements throughout.Enjoy relaxing or entertaining on the deck overlooking a spacious yard with a babbling brook—perfect for peaceful mornings or summer

Kerry Mulverhill Brattleboro Area Realty

403 Tyler Hill Rd, Vernon, VT 05354
/27
$3,125,000
- 4 Beds
- 4 Baths
- 4,333 Sq Ft
56 Coldbrook Crossing, Wilmington, VT 05363

Spectacular custom home at the base of the Hermitage Club in the Coldbrook Crossing community, adjacent to the base of Haystack mountain. This is a stunning lot overlooking the trails and sunsets beyond, with easy mountain access, snowmobile trail access, and views unimpeded by any other homes. The luxurious features include a vaulted great room with exposed natural wood beams and stone hearth

Adam Palmiter Berkley & Veller Greenwood/Dover

56 Coldbrook Crossing, Wilmington, VT 05363
/27
$359,000
- 3 Beds
- 2.5 Baths
- 1,266 Sq Ft
7271 Windham Hill Rd, West Townshend, VT 05359

Charming and meticulously maintained, this classic Vermont A-frame with a tasteful addition offers the perfect blend of character and comfort. Nestled on just under 2 acres, the home features 3 cozy bedrooms, warm wood accents, and inviting living spaces filled with natural light. Whether you're enjoying a quiet morning on the deck or taking in the peaceful surroundings, this property is a true

Carrie Mathews Winhall Real Estate

7271 Windham Hill Rd, West Townshend, VT 05359
/50
$318,000
- 3 Beds
- 1 Bath
- 1,222 Sq Ft
1082 W River Rd, Brattleboro, VT 05301

Welcome to 1082 West River Road — a peaceful, well-located gem just minutes from downtown Brattleboro. This charming home offers the perfect blend of convenience, outdoor space, and natural beauty. Set on a spacious lot with a large, open yard, there's room to garden, gather, or simply relax and enjoy the Vermont seasons. The private river access makes it easy to enjoy kayaking, swimming, or

Kate Barry EXP Realty

1082 W River Rd, Brattleboro, VT 05301
/46
$299,900
- 6 Beds
- 4 Baths
- 3,581 Sq Ft
27 Westminster Terrace, Bellows Falls, VT 05101

Don't miss this rare opportunity to own a 3-story Victorian multi-family home, perfectly situated in the heart of town. This classic property features four fully occupied rental units generating a solid net income of $32,142 per year. Unit #4 is not fully independent as it has no kitchen and shares the kitchen with family members renting unit 1 . Each unit showcases original hardwood floors,

Jon Tourville BHG Masiello Brattleboro

27 Westminster Terrace, Bellows Falls, VT 05101
/26
$349,900
- 3 Beds
- 1.5 Baths
- 1,370 Sq Ft
749 Vermont Route 100, Wardsboro, VT 05355

This charming, updated 3-bedroom, 2-bath Cape style home sits on 0.17 acres in the heart of Vermont's ski country. Filled with natural light, the warm and inviting interior features a main-level bedroom, while two additional upstairs bedrooms are perfect for guests. After a day on the slopes, unwind by the cozy gas fireplace. Enjoy your morning coffee on the covered porch, or spend evenings

Cassandra Ehrlich BHG Masiello Brattleboro

749 Vermont Route 100, Wardsboro, VT 05355
/12
$19,999
- Land
- 2.00 Acres
- $10,000 per Acre
14 Brickyard Rd, Dover, VT 05341

Beautiful hillside parcel less than ten minutes from Mount Snow but outside the direct path of heavy tourist traffic. Brickyard Road is a winding packed-gravel road dotted sparsely with homes for full-time Dover residents, each with plenty of land and privacy.From the roadside the topography dips down about 5 feet, then quickly comes to a much more gradual slope which continues for approximately

David White OwnerEntry.com

14 Brickyard Rd, Dover, VT 05341
/10
$35,000
- Land
- 1.10 Acres
- $31,818 per Acre
4 Antler Loop, Dover, VT 05356

Wooded Acre Close to Skiing at Mount SnowBeautiful wooded parcel less than ten minutes from skiing at Mount Snow and all the attractions in downtown Dover.While the property's address is technically 4 Antler Loop, it's much easier to access off the end of Timberview Road, which is one street up the hill. After passing by a gorgeous home at 15 Timberview, the road swaps over from gravel to grassy.

David White OwnerEntry.com

4 Antler 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.