Windham County VT Houses for Sale

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  /36

  $357,000

  $25K PRICE DROP

  • 6 Beds
  • 2.5 Baths
  • 3,590 Sq Ft

  88 Westminster St, Town of Rockingham, VT 05101

  Welcome to this stately New Englander located in the heart of Bellows Falls, offering the perfect blend of historic character and generous living space. With over 4,500 square feet, this grand home provides 15 rooms, 6 bedrooms and the potential for 4 bathrooms across multiple levels, giving plenty of room for family, guests, home office space, or multi-generational living. Beautiful period

  Jamie Watson BHG Masiello Keene

  88 Westminster St, Town of Rockingham, VT 05101
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  /29

  $325,000

  $55K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,750 Sq Ft

  34 Main St, Wardsboro, VT 05355

  Lovely late 1800s farmhouse conveniently located in the village of Wardsboro, Vermont, just a short drive to both Mount Snow and Stratton ski resorts. Meticulously maintained, the home sits on a well-positioned parcel with ample parking, private lawn space, and direct snowmobile trail access, plus easy walking access to the nearby convenience store for everyday necessities. Inside, the home

  Adam Palmiter Berkley & Veller Greenwood/Dover

  34 Main St, Wardsboro, VT 05355
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  /27

  $519,000

  • 3 Beds
  • 2.5 Baths
  • 1,784 Sq Ft

  56 Park Laughton Rd, East Dummerston, VT 05346

  A wonderful Colonial home in Dummerston Village Vermont. Classic layout with a huge primary bedroom with double closets, 2 additional generouslysized bedrooms and a full bath on the second floor. The first floor has a large family room, dining room, a full bath with laundry, and a lovely 1/2 bath. Freshly updated with a new roof, new Anderson windows, new high efficiency furnace, whole house

  Derek Greene Derek Greene

  56 Park Laughton Rd, East Dummerston, VT 05346
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  /60

  $549,000

  $76K PRICE DROP

  • 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
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  /35

  $2,399,000

  $100K PRICE DROP

  • 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
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  /23

  $325,000

  • 3 Beds
  • 2 Baths
  • 2,304 Sq Ft

  3156 Grafton Rd, Townshend, VT 05353

  Attractive Gambrel Style home with raised deck overlooking 1.5 acres offers private level backyard with babbling brook , apple trees and outbuilding. The first floor of this sweet primary home has a kitchen with custom cabinets, open dining area with access to the deck , full bathroom and large Livingroom . The second floor has 3 spacious bedrooms and another 3/4 bathroom . The walk -out basement

  Janet Lucier Barrett & Valley Assoc. Inc

  3156 Grafton Rd, Townshend, VT 05353
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  /60

  $1,600,000

  • 5 Beds
  • 5 Baths
  • 6,118 Sq Ft

  3 Eldredge Rd, Chester, VT 05143

  A rare opportunity to own a remarkable piece of Vermont and literary history. Lovingly designed and restored by the creators of the beloved Llama Llama children's book series and the accompanying Netflix animated series, this extraordinary mini-estate is offered for the first time by the family.The meticulously restored and maintained five-bedroom, five-bath, 6,100+ square foot post-and-beam

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  3 Eldredge Rd, Chester, VT 05143
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  /23

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 3,268 Sq Ft

  7 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 3 bedroom, 2.5 bath home has exposed natural woodwork throughout, a great open concept floor plan with large vaulted living room and wood burning fireplace on brick hearth,

  Adam Palmiter Berkley & Veller Greenwood/Dover

  7 Mill Rd, West Dover, VT 05356
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  /3

  $225,000

  $50K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft

  2173 Vermont 8a, Whitingham, VT 05361

  4 bedroom 2 bath home located on 4.7 acres. Has a ground level access. Level parking and garden spots. There are huge White Pine trees surrounding this home. Showings delayed until September 29, 2025 to allow for cleaning. License to Sell is needed and in progress, Expected in October.

  Mark Yule BHG Masiello Brattleboro

  2173 Vermont 8a, Whitingham, VT 05361
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  /54

  $498,750

  $46K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,263 Sq Ft

  1488 Hartley Hill Rd, Putney, VT 05346

  Welcome to this spacious contemporary home located on the desirable Hartley Hill Road, conveniently situated near Saxtons River, Bellows Falls, Putney, and I-91. Built in 2008, this well-maintained home offers quality craftsmanship including a brand new roof installed April 2026, high-end utilities, and modern comforts throughout. The finished, walk-out lower level features radiant heat, abundant

  Chelsea Richardson Barrett and Valley Associates Inc.

  1488 Hartley Hill Rd, Putney, VT 05346
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  /30

  $997,000

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 3,865 Sq Ft

  47 West Rd, Wilmington, VT 05363

  Be among the first to enjoy this brand-new mountain modern home in the sought-after Chimney Hill community, with an anticipated completion date of September 2026. Thoughtfully designed for both year-round living and weekend getaways, this 3-bedroom, 4-bath home offers a bright, open floor plan filled with natural light and clean, contemporary finishes.The main living area creates an inviting

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  47 West Rd, Wilmington, VT 05363
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  /23

  $255,000

  Open Sat 11AM - 1PM Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,683 Sq Ft

  159 Lower Bartonsville Rd, Chester, VT 05143

  Welcome to 159 Lower Bartonsville Road, a charming carriage house nestled along a scenic country farm road in Rockingham, Vermont, just moments from the picturesque restored Bartonsville covered bridge. This 3 bed, 1.5 bath property features authentic 1830s architecture and timeless rustic character, offering a solid structural foundation with much of its original detail preserved. Seamlessly

  Abby Gerbick Century 21 Highview Realty

  159 Lower Bartonsville Rd, Chester, VT 05143
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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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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 201 - 228, Page 6 of 6