Windham County VT Houses for Sale

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  /33

  $799,000

  • 5 Beds
  • 2.5 Baths
  • 3,064 Sq Ft

  32 Old Town Rd, Dover, VT 05356

  Tucked away on a country road in Dover, Vermont, this inviting five bedroom, three bathroom home offers the perfect blend of comfort, functionality, and outdoor enjoyment. Set on a scenic open lot with a tranquil pond and open views, the property includes a spacious inlaw apartment on the walkout lower level ideal for guests, extended family, or potential rental income.The main home features

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  32 Old Town Rd, Dover, VT 05356
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  /60

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,520 Sq Ft

  96 E Brook Crossing Unit CHC209.000, Wilmington, VT 05363

  New Listing in Section C! Quiet corner of the Resort features this Classic Chalet with a mudroom entry, bedroom with slider to the deck, a full bath, open concept kitchen with wood cabinets and breakfast bar, dining area with a bay window, living area with vaulted ceiling, wood burning fireplace and slider to the deck. Upstairs has a full bath with skylight and two bedrooms, one with a skylight

  Sigrid Pickering Chimney Hill Realty

  96 E Brook Crossing Unit CHC209.000, Wilmington, VT 05363
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  /60

  $549,000

  • 3 Beds
  • 2.5 Baths
  • 3,415 Sq Ft

  23 Meeting House Ln, Brattleboro, VT 05301

  First Time on the Market – Premier Brattleboro Location!Nestled on one of the most desirable lots in one of Brattleboro’s finest neighborhoods, this well-maintained home is being offered for sale for the very first time! Custom-built by the current owner in 1970 with attention to detail, this spacious ranch offers comfort, functionality, and an impressive list of amenities.Perfect for

  Bert Inman RE/MAX Town & Country

  23 Meeting House Ln, Brattleboro, VT 05301
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  /17

  $625,000

  • 4 Beds
  • 2 Baths
  • 1,900 Sq Ft

  9 Cooper Hill Rd, Dover, VT 05341

  Welcome to your own private sanctuary, tucked away on six stunning acres of unspoiled natural beauty. This inviting 4-bedroom, 2-bathroom home offers the perfect balance of rustic charm and modern comfort, creating an ideal retreat for those seeking peace, privacy, and outdoor adventure.Surrounded by lush woods and open space, the property features a serene private pond, the soothing sounds

  Carrie Mathews Winhall Real Estate

  9 Cooper Hill Rd, Dover, VT 05341
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  /40

  $1,695,000

  • 7 Beds
  • 7.5 Baths
  • 8,364 Sq Ft

  251 Pratt Bridge Rd, Jamaica, VT 05343

  Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas & the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated B&B. Prepare to be Enchanted! An

  TG Glazer Winhall Real Estate

  251 Pratt Bridge Rd, Jamaica, VT 05343
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  /49

  $699,000

  • 2 Beds
  • 2 Baths
  • 2,144 Sq Ft

  956 Old Cheney Rd, West Townshend, VT 05359

  Experience Vermont living in this beautifully restored 1790 farmhouse, set on 44 acres, gardens, ponds, and stone walls. Just a short drive from Magic Mountain, Grafton Trails, Jamaica State Park, and the iconic Hamilton Falls, this property combines historic character with modern comforts in the heart of southern Vermont.Step inside and discover rich craftsmanship throughout: handmade doors,

  Kim Meeker Southern Vermont Realty Group

  956 Old Cheney Rd, West Townshend, VT 05359
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  /47

  $995,000

  • 5 Beds
  • 1 Bath
  • 1,224 Sq Ft

  6036 Jacksonville Stage Rd, Guilford, VT 05301

  Welcome to a rare and breathtaking slice of Vermont. This expansive 216-acre farm offers a beautiful mix of open pastures, mature woodlands, fruit trees, berry bushes, and a small section of scenic wetlands – a true haven for nature lovers and outdoor enthusiasts seeking peace and space in every direction. Set along a quiet dirt road near the Massachusetts border, with the added convenience of

  Melissa Nebelski Skihome Realty

  6036 Jacksonville Stage Rd, Guilford, VT 05301
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  /35

  $369,000

  • 5 Beds
  • 3 Baths
  • 3,364 Sq Ft

  21 Main St, Saxtons River, VT 05154

  Welcome to history, this 1830's colonial home has so much charm and character to offer! This home is situated in the quaint village of Saxtons River just feet from the Local market store as well as the admired and prestigious Vermont Academy School. With plenty of space to host whether it be in the large grand feeling living room with the original woodwork and fireplaces or the spacious back yard

  Thaddeus Abare Barrett and Valley Associates Inc.

  21 Main St, Saxtons River, VT 05154
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  /34

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 2,033 Sq Ft

  64 Gleason Farm Ln, Jamaica, VT 05343

  Nestled on nearly 2 flat acres, this beautifully maintained South-facing New England Cape Cod farmhouse is a rare find in the mountains. Located on a private dead-end road, the home offers peaceful seclusion while being just a short drive to Stratton Mountain for skiing and tubing in the winter and Jamaica State Park for hiking and stunning waterfalls in the warmer months. With only one owner,

  Carrie Mathews Winhall Real Estate

  64 Gleason Farm Ln, Jamaica, VT 05343
• 

  

  /40

  $450,000

  • 4 Beds
  • 2 Baths
  • 1,908 Sq Ft

  119 Main St, Putney, VT 05346

  MOTIVATED SELLERS! Built in 1798, 119 Main Street is the third oldest home in Putney. With its original beams, colonial architecture, and location on Main Street, it's a historic gem in waiting for new people to love it. The owner who resided here for many years, took pride in preserving and adding to the beautiful terraced perennial gardens throughout the large in-town lot, which is just under

  Heather Gleim CENTURY 21 North East

  119 Main St, Putney, VT 05346
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  /35

  $949,000

  • 4 Beds
  • 3.5 Baths
  • 2,272 Sq Ft

  12 Encore Place, Dover, VT 05356

  Mountain Modern Living with unmatched ski views of Mount Snow. Discover the perfect blend of luxury and nature in this 3 year young contemporary home ideally situated to capture breathtaking unobstructed views of Carinthia. This thoughtfully designed 4 bedroom home offers an open concept floor plan while still offering privacy and cozy spaces that highlight the beauty of the alpine landscape.

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  12 Encore Place, Dover, VT 05356
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  /43

  $398,000

  • 6 Beds
  • 2 Baths
  • 1,920 Sq Ft

  247 Vt Route 100 N, Wilmington, VT 05363

  Conveniently located on Route 100 between Wilmington Village and Mount Snow. Two separate 3 bedroom, totally renovated, units. This would be a wonderful multi-generational home, two family purchase, use one unit - rent one unit. Wheeler Farm view of pasture and mountain ranges. Exterior garden shed. Plenty of parking, an amazing view and waiting for you!

  Janet Boyd Boyd Real Estate

  247 Vt Route 100 N, Wilmington, VT 05363
• 

  

  /31

  $445,000

  • 4 Beds
  • 3 Baths
  • 1,854 Sq Ft

  132 Sun and Ski Rd, Wilmington, VT 05363

  Welcome to Chateau Chelsea! This charming three-level, 4-bedroom, 3-bathroom single-family home is situated in the heart of Vermont’s picturesqueGreen Mountains. Named after the owners' beloved pup, this property has been a cherished gathering place for family and friends year-round. Conveniently located just over 2 hours from Boston, 90 minutes from Hartford, CT, and less than 4 hours from NYC,

  Patrice Schneider Southern Vermont Realty Group

  132 Sun and Ski Rd, Wilmington, VT 05363
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  /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 chefs dream kitchen

  Leslie Fraser Four Seasons Sotheby's Int'l Realty

  100 Mowing Way, Wilmington, VT 05363
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  /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
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  /39

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  156 Mountain View Rd, Wilmington, VT 05363

  This charming Cape-style home offers three bedrooms and two full baths across the first two floors, featuring bamboo hardwood floors throughout and abundant natural light. Upstairs bedrooms have built in dressers. The living room boasts a cozy gas fireplace and flows seamlessly into the open-concept kitchen and dining area. A MAJOR highlight is the deeded lake rights to the picturesque Lake

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  156 Mountain View Rd, Wilmington, VT 05363
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  /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
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  /31

  $499,000

  • 3 Beds
  • 2 Baths
  • 2,372 Sq Ft

  285 Chimney Hill Rd, Wilmington, VT 05363

  Contemporary retreat in the heart of Chimney Hill. Set on a double lot along a paved road offering the perfect balance of comfort, style and year round convenience. Located just minutes from Wilmington village, Lake Whitingham, Mount Snow and scenic trail that leads to the summit of Haystack Peak in the Green mountain National Forest. The bright, open concept interior is filled with natural

  Monique White Deerfield Valley Real Estate

  285 Chimney Hill Rd, Wilmington, VT 05363
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  /60

  $899,000

  • 5 Beds
  • 4.5 Baths
  • 5,000 Sq Ft

  42 Blackberry Ln, Jamaica, VT 05343

  Idyllic, Picturesque, Expansive, Vast Family Farm with outbuildings and Large Farmhouse! Known to some as Sweet Berry Farm the blueberries and blackberries are plentiful along with many other productive fruits trees, a grove of 20 mature apple trees with many over 30 years old, , flowers and veggies in the gardens. This location just off of Route 30 is perfect for ALL of your Vermont dreams and

  Steve Goldfarb Deerfield Valley Real Estate

  42 Blackberry Ln, Jamaica, VT 05343
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  /35

  $454,000

  • 4 Beds
  • 2.5 Baths
  • 1,374 Sq Ft

  38 Snow Rd, Dover, VT 05356

  Quintessential Vermont chalet with stunning southern views over rolling meadows and distant ridgelines without a neighbor in sight. Privately nestled in a serene country setting, this sweet chalet exudes warmth and character with wood flooring, a classic fieldstone wood-burning fireplace, exposed beam ceilings, and a sunlit dining area. The main level includes a thoughtfully updated kitchen with

  Monique White Deerfield Valley Real Estate

  38 Snow Rd, Dover, VT 05356
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  /49

  $475,000

  • 3 Beds
  • 3 Baths
  • 2,463 Sq Ft

  1591 Higley Hill, Marlboro, VT 05344

  Wonderful home on 11.2 acres in a peaceful setting on Higley Hill in Marlboro. The main level boasts a beautiful family room addition with lots of windows and a gas fireplace, galley kitchen with stainless appliances, dining area, 3/4 bath with laundry, living room with gas stove, 3/4 bath with sitting area and a primary bedroom with ensuite full bath. A loft area that can be used as a bedroom or

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  1591 Higley Hill, Marlboro, VT 05344
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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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  /40

  $809,000

  • 3 Beds
  • 3 Baths
  • 3,606 Sq Ft

  46 Scattered Timber Rd, Wilmington, VT 05363

  Escape to the Green Mountains with this custom-built Moose Head Cedar Log Cabin, beautifully sited on a private wooded lot in the sought-after Chimney Hill community. Enjoy ridgeline views, peaceful surroundings, and the fresh Vermont air. Inside, the offers timeless craftsmanship and open-concept living, featuring soaring post and beam construction with vaulted ceilings, floor-to-ceiling windows

  Monique White Deerfield Valley Real Estate

  46 Scattered Timber Rd, Wilmington, VT 05363
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  /38

  $1,750,000

  • 4 Beds
  • 3.5 Baths
  • 2,862 Sq Ft

  161 Depot Rd, Williamsville, VT 05362

  Perched high above the enchanting hills of Newfane, VT, lies a truly one-of-a-kind property. This meticulously crafted home offers an off-grid, private retreat with breathtaking views of the surrounding landscape. Constructed in 2003, the post and beam design incorporates wood and stone harvested from its expansive219-acre setting, showcasing a harmonious blend of nature and architecture. This

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  161 Depot Rd, Williamsville, VT 05362
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  /46

  $990,500

  • 3 Beds
  • 4.5 Baths
  • 3,318 Sq Ft

  42 Sugar House Rd, West Dover, VT 05356

  Tucked into the serene hills of Dover, Vermont, this custom crafted mountain home offers the ideal blend of rustic charm and modern comfort just minutes from Mount Snow and The Hermitage Club. Set on a private lot with winter views of both ski mountains, this 3-bedroom(+bonus bedroom), 4.5-bath home features an open-concept layout with soaring cathedral ceilings, exposed beams, and a stunning

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  42 Sugar House Rd, West Dover, VT 05356
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  /6

  $795,000

  • 3 Beds
  • 2 Baths
  • 1,267 Sq Ft

  635 Vermont Route 100, Wardsboro, VT 05355

  Great short term or long term rental for investment or use by a large family. Rent one and enjoy the other. Located 1.6 miles north of Mt. Snow with direct access to VAST from this property. This home was renovated in 2014 including a new roof, windows and doors. Current owners replaced hot tub 2 years ago and a tankless water heater 3 years ago. THIS PROPERTY IS ALSO BEING SOLD WITH LISTING

  Ginny Read Read Realty LTD

  635 Vermont Route 100, Wardsboro, VT 05355
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  /8

  $795,000

  • 4 Beds
  • 3 Baths
  • 2,142 Sq Ft

  633 Route 100, West Wardsboro, VT 05360

  Great short or long term rental for investment or use by a large family. Rent one and enjoy the other. Located 1.6 miles north of Mount Snow and with direct access to VAST from this property. This home was renovated in 2014 including new ro0f, windows & doors. Current owners replaced the hot tub 1 year ago and the tankless water heater 3 years ago. Being sold furnished and ready for family,

  Ginny Read Read Realty LTD

  633 Route 100, West Wardsboro, VT 05360
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  /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

  $349,000

  • 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
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  /26

  $299,900

  • 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
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  /51

  $899,800

  • 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
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  /56

  $519,000

  • 3 Beds
  • 2.5 Baths
  • 2,494 Sq Ft

  63 Cooper Hill Rd, Dover, VT 05356

  New Price Improvement!!! 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

  Michelle O'Neil Deerfield Valley Real Estate

  63 Cooper Hill Rd, Dover, VT 05356
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  /60

  $335,000

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft

  108 Spruce Grove Rd Unit M286, Wilmington, VT 05363

  This house sits on a lot that is surrounded by common land so it feels very secluded and private. Newer septic, roof, and main level flooring, and the prior owner did a lot of custom wood paneling with built-ins, and creative decorating which add to its charm. The main level has a mudroom entry with laundry and storage space, full bath, kitchen with open shelving above and cabinets below, newer

  Sigrid Pickering Chimney Hill Realty

  108 Spruce Grove Rd Unit M286, Wilmington, VT 05363
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  /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
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  /60

  $749,000

  • 3 Beds
  • 2 Baths
  • 2,170 Sq Ft

  27 Stearns Ave, Wilmington, VT 05363

  Nestled in the heart of Vermont’s Green Mountains, check out this stunning Moosehead log home. With private, shared access to Lake Raponda just a short walk away, this inviting single-family home seamlessly blends rustic charm, modern comfort, and a serene natural setting. With 2,170 sq. ft. of living space, this 3-bedroom, 2-bath home welcomes you with warmth and tranquility from the moment you

  John Redd Skihome Realty

  27 Stearns Ave, Wilmington, VT 05363
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  /29

  $279,900

  • 3 Beds
  • 2 Baths
  • 1,183 Sq Ft

  4322 Augur Hole Rd, Brattleboro, VT 05301

  Super location! Easy access to Rt 9 and Rt 30 but tucked into nearly a level acre in a lovely country setting. You can tell the previous occupants loved their gardens and a bit of work would restore the blooms to full glory. The pool is a bonus but is waiting for some care to get up and running...The home has emerged from a fun loving schoolhouse filled with learning and joy to a cozy,

  Christine Lewis Brattleboro Area Realty

  4322 Augur Hole Rd, Brattleboro, VT 05301
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  /60

  $895,000

  • 3 Beds
  • 3 Baths
  • 2,258 Sq Ft

  266 Ursa Ridge Rd, Dummerston, VT 05301

  This home is living art, tucked away at the end of the road of lovely homes & hundreds of acres ridgetop, yet only 10 minutes from downtown Brattleboro. Built by a craftsman this home is gracious & energy efficient. Building materials have been harvested from it's 51-1/2 acre woodland. Rooms are thoughtfully designed awash with natural light. Walk up the covered, stone walkway to enter the

  Randi Ziter Brattleboro Area Realty

  266 Ursa Ridge Rd, Dummerston, VT 05301
• 

  

  /27

  $559,000

  • 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
• 

  

  /18

  $319,900

  • 3 Beds
  • 1 Bath
  • 1,323 Sq Ft

  164 Chestnut St, Brattleboro, VT 05301

  Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with

  Christine Lewis Brattleboro Area Realty

  164 Chestnut St, Brattleboro, VT 05301
• 

  

  /35

  $795,000

  • 4 Beds
  • 5 Baths
  • 3,129 Sq Ft

  20 Ray Hill Rd, Wilmington, VT 05363

  Rare opportunity to own a completely remodeled and updated vintage farmhouse, completely turn key. This stunning home sits just up from the country village of Wilmington with easy access to dining and shopping, a short drive to Mount Snow, and near the amazing Lake Whitingham, for true four season enjoyment. The interior features meticulously updated open concept living areas, a chef's kitchen

  Adam Palmiter Berkley & Veller Greenwood/Dover

  20 Ray Hill Rd, Wilmington, VT 05363

Showing Results 121 - 160, Page 4 of 6