472

Windham County VT Homes for Sale

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  • /43

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,312 Sq Ft

    96 Lower Bartonsville Rd, Chester, VT 05143

    This tastefully updated ranch-style home is set on a unique one-acre parcel with a convenient location to the Williams River. Three bedrooms and two baths, thoughtfully updated interior with inviting living spaces and the convenience of one level living. A full basement provides valuable additional space and could be finished to create a family room, home office, recreation area, or even a gym.

    Jessica Citera Cummings & Co

    96 Lower Bartonsville Rd, Chester, VT 05143
  • /29

    $420,000

    $169K PRICE DROP
    • 7 Beds
    • 5 Baths
    • 3,518 Sq Ft

    343 Haystack Rd, Wilmington, VT 05363

    An opportunity for investors or buyers seeking value. Main house offers four bedrooms, four baths; including a large primary suite. The basement has a kitchen, bath and living space with walkout access to the backyard. The three-car garage with a workshop is a great bonus for anyone who loves outdoor activities or needs extra storage space. Plus, the separate two bedroom, one bath apartment above

    Jessica Citera Cummings & Co

    343 Haystack Rd, Wilmington, VT 05363
  • /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
  • /60

    $995,000

    $205K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 3,906 Sq Ft

    8 Twin Rocks Rd, Dover, VT 05356

    Mountain Property w/ Stunning Barn. Convenient access to Mt Snow skiing & 18 hole golf course, also VT's renowned VAST Trails System. Mountain Retreat w/amazing Income & Expansion Potential. Tucked away at end of a quiet country road in desirable West Dover, this remarkable 5-bdrm, 5-bath contemporary offers the perfect blend of privacy, recreation & opportunity. This property is ideally

    Jen Baker Connecticut River Valley Realty

    8 Twin Rocks Rd, Dover, VT 05356
  • /14

    $210,000

    • Land
    • 35 Acres
    • $6,000 per Acre

    00 Vermont Route 100, Jamaica, VT 05343

    Discover the beauty and tranquility of this picturesque wooded parcel—approximately 35 acres—nestled along the serene Deerfield River and spanning the border of Jamaica and Wardsboro. Perfectly situated within easy reach of Mount Snow, Stratton, and Bromley, the property offers convenient access to year-round recreation while preserving the sense of peace and privacy that only a large forested

    Patrice Schneider Southern Vermont Realty Group

    00 Vermont Route 100, Jamaica, VT 05343
  • /29

    $825,000

    • 4 Beds
    • 3.5 Baths
    • 1,993 Sq Ft

    18 High Point Dr Unit 501, Stratton, VT 05360

    Located just one mile from Stratton’s Base Lodge and Village, this 4-bedroom, 3-bath end-unit Styles Brook townhome offers the perfect combination of convenience, comfort, and year-round mountain living. Spanning three levels, Unit 501 enjoys the added privacy, extra windows, and abundant natural light that come with end-unit ownership. The main level is designed for gathering, featuring

    Cheyanne Pugliese

    18 High Point Dr Unit 501, Stratton, VT 05360
  • /39

    $839,000

    Open Sun 11AM - 1PM
    • 5 Beds
    • 4.5 Baths
    • 3,840 Sq Ft

    42 Blackberry Ln, Jamaica, VT 05343

    Only 8 miles from Stratton Mountain, this extra-large expanded farmhouse provides ample space, quiet, and tons of classic Vermont charm. Set in a lush garden landscape surrounded by meadows, a stone wall, perennial gardens, an apple orchard, a barn, & multiple outbuildings, the home feels like old Vermont while being close to major amenities. The original home is from the 19th century but

    Cheyanne Pugliese

    42 Blackberry Ln, Jamaica, VT 05343
  • /17

    $110,000

    • Land
    • 5,227 Sq Ft
    • $916,667 per Acre

    117 * Fuller Dr, Brattleboro, VT 05301

    Nestled just behind 117 Fuller Drive, with privacy and easy access from the street, this property is the perfect spot for the tiny home you have been longing for. Water, sewer, and electric are all at the street, and the seller will help to keep the access accessible :) The subdivision has received preliminary approval from the town, with finalization to be completed prior to sale—giving you

    Rebecca Seymour Brattleboro Area Realty

    117 * Fuller Dr, Brattleboro, VT 05301
  • /25

    $679,000

    • 4 Beds
    • 3 Baths
    • 2,600 Sq Ft

    14A Grouse Ln Unit 14A, Dover, VT 05356

    Gorgeous Post and Beam style townhome overlooking spectacular views of the Hermitage Club ski trails and sunsets over the ridgeline. This private end unit features an amenity rich location thanks to direct VAST snowmobile trail access, easy nearby access to the Mount Snow ski resort, hiking and biking trails in the summer, and nearby convenience to the area's numerous lakes, dining and shopping.

    Adam Palmiter Berkley & Veller Greenwood/Dover

    14A Grouse Ln Unit 14A, Dover, VT 05356
  • /5

    $150,000

    $25K PRICE DROP
    • Land
    • 23.4 Acres
    • $6,410 per Acre

    4125 Chester Hill Rd, Grafton, VT 05146

    Escape to nature at 4125 Chester Rd, Grafton, VT—a serene 23.4-acre retreat where peaceful living meets outdoor adventure. Enjoy the soothing sounds of Hall Brook as it winds through the property, perfect for quiet reflection and leisurely strolls. Embrace the winter wonderland with nearby snowmobile trails and take advantage of the location's proximity to Okemo Mountain for a variety of

    Jamie Watson BHG Masiello Keene

    4125 Chester Hill Rd, Grafton, VT 05146
  • /36

    $319,000

    • 3 Beds
    • 3.5 Baths
    • 2,000 Sq Ft

    12 Par Dr Unit 12, Wilmington, VT 05363

    Enjoy year-round Vermont living in this classic Spyglass townhome that is located right on the 10th fairway of the Haystack Golf course. Offering 3 bedrooms plus a sleeping loft and 3.5 baths. Designed for comfort and convenience, the main level features a mudroom, an open-concept living and dining area with vaulted ceilings, a fully equipped kitchen, and a cozy wood-burning fieldstone fireplace.

    Rich Caplan Deerfield Valley Real Estate

    12 Par Dr Unit 12, Wilmington, VT 05363
  • /31

    $649,000

    • 3 Beds
    • 2.5 Baths
    • 1,650 Sq Ft

    28 Styles Branch Rd Unit 305, Stratton, VT 05360

    Experience the ease of Stratton Mountain living from this inviting three-bedroom Styles Brook condominium, ideally located just moments from the lifts. Hop on the convenient winter shuttle or enjoy a pleasant walk to the base area, with Stratton's Sports Center, fitness facilities, and year-round amenities just a short stroll away.Designed for both comfort and entertaining, the spacious main

    Carrie Mathews Winhall Real Estate

    28 Styles Branch Rd Unit 305, Stratton, VT 05360
  • /10

    $149,000

    • 1 Bed
    • 1 Bath
    • 514 Sq Ft

    25 Elvas Way, Dover, VT 05341

    Remote cabin on 14.4 acres with the Bemis Brook running through. Trails and Class 4 Roads surround the property. Snowmobile and 4 Wheeler in the neighborhood.

    Mark Yule BHG Masiello Brattleboro

    25 Elvas Way, Dover, VT 05341
  • /34

    $699,000

    • 3 Beds
    • 4 Baths
    • 3,796 Sq Ft

    233 Poverty Row, Whitingham, VT 05361

    What a gem! This absolutely meticulously maintained 2015 farmhouse sits just up from Lake Sadawga and Harriman Reservoir on a private 2 acre parcel off a paved road. The curb appeal is beyond what most can dream of with gorgeous perennial gardens, split rail fencing, ample yard space, and total privacy. Features include a beautiful open floor plan with large living room and family room, beautiful

    Adam Palmiter Berkley & Veller Greenwood/Dover

    233 Poverty Row, Whitingham, VT 05361
  • /37

    $625,000

    • 4 Beds
    • 2 Baths
    • 2,070 Sq Ft

    239 Valley View Rd, Dover, VT 05356

    This contemporary 3-bedroom plus loft, 2-bath home in Dover Hills offers both comfort and convenience. The property features a detached 2-car garage with overhead storage, an additional carport, and a wood shed. The recently remodeled kitchen boasts new cabinets, countertops, and appliances, complemented by wood floors throughout and new skylights that fill the space with natural light. A gas

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    239 Valley View Rd, Dover, VT 05356
  • /8

    $225,000

    $70K PRICE DROP
    • Land
    • 54.8 Acres
    • $4,106 per Acre

    0 Townshend Dam Rd Unit 5066172, Wardsboro, VT 05355

    Perced in 2025 for a 5 bedroom home! Explore the potential of this beautiful 53.8 acre parcel just 3.5 miles from the scenic Townshend Dam. This expansive property offers a peaceful, wooded setting with ample privacy, ideal for recreation, a possible future homesite, or continued forest management. Currently enrolled in Vermont’s Current Use Program, the land offers significant tax savings and

    Carrie Mathews Winhall Real Estate

    0 Townshend Dam Rd Unit 5066172, Wardsboro, VT 05355
  • /60

    $999,000

    $89K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 5,828 Sq Ft

    151 Townshend Rd, Grafton, VT 05146

    STRONG RENTAL HISTORY & INVESTMENT OPPORTUNITY IN A TURN-KEY PROPERTY. Located in the heart of Grafton, Vermont, on a spacious one-acre, flat lot a quick stroll from town, this extensively renovated property offers exceptional flexibility and scale. The single family or multi-family property is configured to allow division into two condominium-style living spaces plus a separate artist loft or

    Erin McCormick KW Vermont

    151 Townshend Rd, Grafton, VT 05146
  • /18

    $68,900

    • Land
    • 21,780 Sq Ft
    • $137,800 per Acre

    Lot 1 - 161 High Peak Way, Wilmington, VT 05363

    Introducing Lot #1 in the High Peak Development, .50-acre double lot offering the foundation for your future Vermont home. This wooded parcel provides the peaceful setting of a cabin in the woods while still being just minutes from Mount Snow, The Hermitage Club, and the year-round recreation of the Deerfield Valley.With public sewer and public water access, the building process is made

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    Lot 1 - 161 High Peak Way, Wilmington, VT 05363
  • /51

    $715,000

    • 3 Beds
    • 3.5 Baths
    • 2,895 Sq Ft

    106 Westminster Rd W, Putney, VT 05346

    Set on 25.8± scenic acres, this 3-bedroom, 3½-bath historic barn conversion offers long views across meadows to the surrounding hills within walking distance of Putney Village. It is a rare Putney combination: genuine privacy & room to explore, w/ village shops, food, arts, Putney Central School, and the town pool nearby. This property features approximately 2,300 sq ft of living space, with 595

    A.J. Bellville Bellville Realty

    106 Westminster Rd W, Putney, VT 05346
  • /26

    $494,000

    $5K PRICE DROP
    • 7 Beds
    • 2 Baths
    • 2,038 Sq Ft

    45 Blue Brook Rd, Dover, VT 05356

    Owners open to offers! A truly unique and eclectic ski chalet. The current owner has tastefully updated this home in order to foster a tremendous rental investment, but it could also work great for anyone looking for a spacious ski home with great access off a paved town road and tremendous mountain proximity. Easily accessible off a paved road, not far from shuttle service, and only a couple

    Adam Palmiter Berkley & Veller Greenwood/Dover

    45 Blue Brook Rd, Dover, VT 05356
  • /2

    $125,000

    • 4 Beds
    • 2 Baths
    • 2,644 Sq Ft

    54 Williams St Unit 56, Bellows Falls, VT 05101

    Offering over 2,500 square feet of potential. The 2.5-story layout with porches offers a project for buyers seeking sweat equity, rental income potential, or a large single-family home tailored to their needs. Located within walking distance of downtown Bellows Falls, you'll be close to shops, restaurants, the Connecticut River, and all the character this historic village has to offer. Please

    Shawna Fox BHHS Verani Upper Valley

    54 Williams St Unit 56, Bellows Falls, VT 05101
  • /29

    $19,500

    • 1 Bath
    • 332 Sq Ft

    218 Qtr.2 89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Valley side unit includes: Queen murphy bed, kitchen, eating area, balcony and a full bath. 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

    Kelly Agrillo Southern Vermont Realty Group

    218 Qtr.2 89 Grand Summit Way, Dover, VT 05356
  • /28

    $725,000

    • 3 Beds
    • 2.5 Baths
    • 2,692 Sq Ft

    858 Sheldon Hill Rd, Wardsboro, VT 05355

    A perfect example of the ideal Vermont home. Beautiful natural woodwork abounds in this post and beam/log home hybrid built in 2005. Conveniently located on a corner lot with tremendous privacy and a spacious cul-de-sac driveway, is this perfect home with perennial gardens, a natural wood facade, stone chimney, stone walkway, large entertaining deck, patio with hot tub, and an exterior elevator

    Adam Palmiter Berkley & Veller Greenwood/Dover

    858 Sheldon Hill Rd, Wardsboro, VT 05355
  • /18

    $250,000

    $30K PRICE INCREASE
    • 3 Beds
    • 1 Bath
    • 1,050 Sq Ft

    5362 Us Route 5, Westminster, VT 05158

    BRAND NEW SEPTIC SYSTEM!! Move-in ready home, ideally situated in the heart of picturesque Westminster. This 3-bedroom, 1-bath home offers the perfect blend of charm, comfort and convenience. Step inside from the sunny, porch into a bright and functional kitchen featuring new countertops and easy access to the first-floor laundry area and recently renovated full bath. The layout flows seamlessly

    Karen Hoppe Berkley & Veller Greenwood Country

    5362 Us Route 5, Westminster, VT 05158
  • /17

    $79,500

    • Land
    • 13,939 Sq Ft
    • $248,438 per Acre

    Lot 2 - 162 High Peak Way, Wilmington, VT 05363

    Discover the perfect opportunity to build your Vermont retreat on this .32 acre lot in the High Peak Development, ideally positioned adjacent to the Haystack Golf Course. This wooded parcel offers the privacy of a cabin-in-the-woods setting while still being just minutes from Mount Snow, The Hermitage Club, and all the four season recreation the Deerfield Valley offers. Charming downtown

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    Lot 2 - 162 High Peak Way, Wilmington, VT 05363
  • /12

    $422,000

    $43K PRICE DROP
    • 3,756 Sq Ft

    820 Western Ave, Brattleboro, VT 05301

    Exceptional cash flow meets classic Vermont charm in this well-maintained 4-unit property in the heart of Brattleboro. The building features a desirable unit mix with two 2-bedroom, 1-bath apartments and two 1-bedroom, 1-bath apartments. Recent improvements include a freshly painted exterior in 2025 and bathroom renovations completed in 2023, reflecting pride of ownership and minimizing near-term

    The Nancy Jenkins Team Nancy Jenkins Real Estate

    820 Western Ave, Brattleboro, VT 05301
  • /24

    $28,995

    • 2 Beds
    • 2 Baths
    • 745 Sq Ft

    304/06 Qtr.2,89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This sleep 6 unit consists of two adjoining units Studio unit (306) Queen murphy bed , kitchenette and full bathroom. Hotel unit (304) Two king beds and full bathroom. Units are located the valley side of the hotel . Lock out units has the benefit of using the unit as a whole or stay in one side and rent the other side out.

    Kelly Agrillo Southern Vermont Realty Group

    304/06 Qtr.2,89 Grand Summit Way, Dover, VT 05356
  • /34

    $299,000

    • 3 Beds
    • 1.5 Baths
    • 1,296 Sq Ft

    170 River Rd, Jamaica, VT 05343

    Charming cape style modular home set on a beautiful, level 3.67 acre parcel. The expansive yard is framed by a stunning mountain backdrop that gives the entire property a peaceful, protected feel. Inside, you’ll find a bright and welcoming three bedroom, one and a half bath layout with plenty of natural light and comfortable living spaces. Mudroom entryway offers nice closet space and washer

    Julie Lowe Lowe's Real Estate, LLC

    170 River Rd, Jamaica, VT 05343
  • /25

    $219,000

    • Land
    • 16.9 Acres
    • $12,959 per Acre

    00 Howe Farm Rd, Jamaica, VT 05343

    Discover the possibilities on this exceptional 16.9-acre Vermont property, where privacy, natural beauty, and year-round recreation come together. With nearly 300 feet of town-maintained road frontage and accessible utilities, this parcel is ready for your vision. Thoughtfully shaped by nature, the land offers three potential building sites, making it ideal for a family compound,

    Patrice Schneider Southern Vermont Realty Group

    00 Howe Farm Rd, Jamaica, VT 05343
  • /47

    $1,995,000

    • 6 Beds
    • 6.5 Baths
    • 5,545 Sq Ft

    420 Ray Hill Rd, Wilmington, VT 05363

    This impressive 6-bedroom, 7-bath farm-style timber frame home, built by Davis Frame and featured on their website as “The Great White Barn,” sits on 3.51 acres just minutes from the Hermitage Club, Mount Snow, downtown Wilmington, lakes, hiking, golf, and VAST trails. Formerly known by its previous owners as “La Maison de Pommes” (House of Apples) for its old apple orchard setting, the home was

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    420 Ray Hill Rd, Wilmington, VT 05363
  • /28

    $480,000

    • 5 Beds
    • 2 Baths
    • 2,194 Sq Ft

    3327 Route 30, Jamaica, VT 05343

    Nestled on 1.25 flat and beautifully maintained acres and just 1/2 mile from the village, this spacious 5-bedroom home offers the perfect blend of charm, convenience, and Vermont lifestyle. The lovely yard features a mature raspberry patch, ample space for gardens, outdoor entertaining, or simply enjoying the peaceful setting. Ideally located just 1/2 mile from the heart of Jamaica Village and

    Carrie Mathews Winhall Real Estate

    3327 Route 30, Jamaica, VT 05343
  • /60

    $319,000

    • 2 Beds
    • 2 Baths
    • 1,164 Sq Ft

    3185 Higley Hill Rd, West Marlboro, VT 05363

    Vermont A-Frame Retreat in Marlboro! Escape to this charming 2-bedroom, 2-bath A-frame set on 2.18 wooded acres in scenic Marlboro, Vermont. With a stream, deck, and peaceful natural setting, this property offers the perfect blend of privacy and character. Inside, you’ll find 1,164 square feet of furnished living space featuring natural light, a wood fireplace, first-floor laundry, and a

    Grayson VanHendrick Flex Realty

    3185 Higley Hill Rd, West Marlboro, VT 05363

Showing Results 441 - 472, Page 12 of 12

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