Windsor County VT Houses for Sale

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  /48

  $847,000

  • 3 Beds
  • 2 Baths
  • 2,034 Sq Ft

  303 Woodbury Rd Unit 6/3/59, Springfield, VT 05156

  Lovely 1778 center chimney cape, antique charm remains after many thoughtful renovations to allow for comfortable modern living. Enjoy the views from the deck over the 40+- acres of rolling fields and forest. Most recently a horse farm this property offers abundant possibilities. Kitchen, sunroom, dining, living rooms 2 baths, laundry and primary bedroom on the first floor, 2 bedrooms upstairs

  Paula Waters Dark Horse Realty

  303 Woodbury Rd Unit 6/3/59, Springfield, VT 05156
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  /50

  $715,000

  • 3 Beds
  • 2 Baths
  • 1,882 Sq Ft

  162 Campbell Rd, Rochester, VT 05767

  This classic Vermont farmhouse has been lovingly renewed from the studs out, preserving its 19th-century charm while adding the comfort and convenience of modern living. Step inside and you’ll find warm hardwood floors crafted from ash, birch and cherry harvested right from the property, exposed beams, and a central brick hearth with a soapstone woodstove that invites you to gather around on

  Kyle Kershner Killington Pico Realty

  162 Campbell Rd, Rochester, VT 05767
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  /59

  $685,000

  • 3 Beds
  • 2 Baths
  • 2,205 Sq Ft

  688 Hidden Heights Rd, Chester, VT 05143

  Classic New England Salt Box - This charming home is nestled in a hillside neighborhood with wonderful western views and sunsets. Indoors you'll find a tidy mudroom entry with space for all your year round gear. Tiled heated floors lead you to the kitchen featuring newer stainless steel appliances. Vaulted ceilings draw you towards the open dining/living room where you'll be bathed in end of

  Joseph Karl William Raveis Real Estate Vermont Properties

  688 Hidden Heights Rd, Chester, VT 05143
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  /52

  $667,500 Open Sat 11AM - 1:30PM

  • 4 Beds
  • 3 Baths
  • 2,794 Sq Ft

  95 Church St, Chester, VT 05143

  Charming Renovated Farmhouse in the Heart of ChesterThis beautifully renovated farmhouse sits on a level half-acre lot just steps from Chester’s Village Green, shops, and local amenities. Offering the perfect blend of historic charm and modern updates, this 4-bedroom, 3-bath home is ideal for year-round living or a Vermont getaway.Inside, enjoy a spacious kitchen with custom

  McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

  95 Church St, Chester, VT 05143
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  /48

  $615,000

  • 3 Beds
  • 3 Baths
  • 2,680 Sq Ft

  1643 Hammond Hill Rd, West Windsor, VT 05089

  Welcome to your private 8-acre retreat in West Windsor, where craftsmanship, comfort, and self-sufficiency meet everyday adventure. Explore wooded trails, swim in the peaceful pond, or sip coffee on the sunny porch. Evenings glow around the fire pit, while a sturdy treehouse sparks play and gardens of flowers bloom through the seasons. Stone stairways, wooden benches, and camping spots complete

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  1643 Hammond Hill Rd, West Windsor, VT 05089
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  /60

  $749,000

  • 4 Beds
  • 3.5 Baths
  • 2,729 Sq Ft

  419 Baileys Mills Rd, Reading, VT 05062

  Welcome to this enchanting, historic Cape nestled on 75.56 pristine acres along the scenic Mill Brook. Ideally located just five miles from GMHA, the property spans both sides of Baileys Mill Road, offering abundant opportunities for equestrians, hobby farmers & nature lovers alike. The land is a rare mix of open pastures, mature woodlands, flowing streams, and panoramic valley views. A network

  Laird Bradley Williamson Group Sothebys Intl. Realty

  419 Baileys Mills Rd, Reading, VT 05062
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  /56

  $750,000

  • 4 Beds
  • 4 Baths
  • 3,300 Sq Ft

  477 Dunham Rd, Bethel, VT 05032

  A work of modern art. Words cannot describe the feeling you get when your eyes settle on this amazing place. Future owners need only appreciate the unique, creative, and thought provoking touches in this very interesting home.The builder/owners have created a family atmosphere centered around the massive stone fireplace, maple floor, open kitchen with impressive island, dining area, and a

  Dean Goulet Dunrovin Real Estate

  477 Dunham Rd, Bethel, VT 05032
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  /49

  $785,000

  • 3 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  228 Leonard Rd, Sharon, VT 05065

  Welcome to your private Vermont retreat on nearly 24 acres of open meadows, woods, and a pristine spring-fed pond. Tucked away in complete seclusion and surrounded by 500 acres of undeveloped maple forest, this peaceful property offers unrivaled privacy and natural beauty. The charming 3-bedroom home features hardwood floors, a cozy wood stove, and a beautifully renovated kitchen with granite

  Mandolyn McIntyre Crow Real Broker LLC

  228 Leonard Rd, Sharon, VT 05065
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  /36

  $799,900

  • 4 Beds
  • 4 Baths
  • 3,780 Sq Ft

  5 Malagash Rd, South Reading, VT 05153

  Set on a spacious and level lot in the scenic countryside of Reading, Vermont, this raised ranch offers room to spread out both inside and out. With 4 bedrooms and 4 bathrooms, the home provides flexible living options across two levels—perfect for larger households, multi-generational living, or hosting guests. The bright main floor features an open layout with a comfortable living area, an

  Katie Ladue Gilbert KW Vermont Woodstock

  5 Malagash Rd, South Reading, VT 05153
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  /22

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft

  690 Route 106, Reading, VT 05062

  Very inviting renovated 1850 Cape on .22a in Reading Village. This home offers the charm only found in a vintage home. Nice kitchen, open to dining room with Jotul woodstove, living room, first floor primary bedroom with balcony, full bath and laundry room. Upstairs you'll find 2 additional bedrooms and a 3/4 bath. Tile & hardwood flooring throughout. Many updates starting in 2017 including

  Dana Waters Dark Horse Realty

  690 Route 106, Reading, VT 05062
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  /28

  $449,000

  • 4 Beds
  • 2 Baths
  • 1,296 Sq Ft

  1668 Hartford Ave, Hartford, VT 05001

  Desirable Wilder location! Within walking distance to Kilowatt and Frost Parks, this charming home offers 4 bedrooms and 2 bathrooms with plenty of space for comfortable living. The recently remodeled kitchen opens seamlessly to the dining room, filling the main living area with natural light. Beautiful hardwood flooring runs throughout, and a spacious walk-up attic provides exciting potential

  Gerry Stark RE/MAX Upper Valley

  1668 Hartford Ave, Hartford, VT 05001
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  /51

  $549,000

  • 3 Beds
  • 2.5 Baths
  • 2,256 Sq Ft

  246 Putnam Hill Rd, Chester, VT 05143

  Discover the perfect balance of privacy, convenience, and sustainable living in this artisan-designed post and beam home. Thoughtfully sited on 10 acres at the end of a country road, this 3 bedroom, 3.5 bath farmhouse offers a rare sanctuary just a short stroll from the charming village center. Designed for today's lifestyle, the home is equipped with solar power and battery backup, ensuring

  Geralyn Donohue Engel & Völkers Okemo

  246 Putnam Hill Rd, Chester, VT 05143
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  /37

  $459,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft

  1979 N Hill Rd, Chester, VT 05143

  Welcome to this attractive Andover Contemporary home, perfectly suited for year-round living or as a Vermont vacation retreat. Built in 2005, this 3 bedroom, 2 bath residence offers modern comfort in a peaceful country setting on 2.1 acres while being just minutes from Okemo Mountain Resort and close to scenic snowmobile trails—ideal for outdoor enthusiasts in every season. The inviting

  Geralyn Donohue Engel & Völkers Okemo

  1979 N Hill Rd, Chester, VT 05143
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  /29

  $299,000 Open Sun 10AM - 12PM

  • 3 Beds
  • 3 Baths
  • 1,260 Sq Ft

  56 Grace Dr, Perkinsville, VT 05151

  3-bedroom, 3-bath Ranch-style home in a quiet North Springfield neighborhood with garage. This single-level rambler offers ease of living with a functional floor plan. Includes a partially finished basement with 3/4 bathroom.Set on a beautiful lot complete with sugar maples, pear, plum, and peach trees, a 21' round above ground pool with decking, and patio area with firepit to enjoy the

  Katie Ladue Gilbert KW Vermont Woodstock

  56 Grace Dr, Perkinsville, VT 05151
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  /60

  $535,000

  • 4 Beds
  • 3.5 Baths
  • 2,865 Sq Ft

  1016 Cherry Hill, Springfield, VT 05156

  Enjoy the best of both worlds with this special property: that top of the world feeling yet only 3 minutes to town! Perched on 7.7 acres over open meadows and mountain views, this spacious Colonial offers exceptional interior and exterior living space, ideal for comfort, flexibility, and entertaining. At one end of the home, a bright and open kitchen/living/dining area maximizes daily living

  Jessica Landers Barrett and Valley Associates Inc.

  1016 Cherry Hill, Springfield, VT 05156
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  /29

  $530,000

  • 3 Beds
  • 2.5 Baths
  • 4,020 Sq Ft

  28 Fairview Terrace, Royalton, VT 05068

  This 3-bedroom, 2.5-bath home is full of potential, with the option to create an auxiliary dwelling for added flexibility. The current owner saw the promise in this gem and has already invested in the important updates: fresh exterior paint, a brand-new septic system, a new roof, upgraded electrical, and other quality improvements. With much of the essential work complete, the next owner has the

  Wendie Wright Coldwell Banker LIFESTYLES - Hanover

  28 Fairview Terrace, Royalton, VT 05068
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  /39

  $435,000

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  22 Birchwood Dr, Perkinsville, VT 05151

  Tucked away at the end of a quiet cul-de-sac, this charming 3-bedroom, 2-bathroom log home offers the perfect blend of privacy, comfort, and convenience. Set on 3.88 acres, this property provides a peaceful retreat with easy access to everyday essentials. Step inside to find warm wood tones, spacious living areas, and classic log home character throughout. The open-concept layout is ideal for

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  22 Birchwood Dr, Perkinsville, VT 05151
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  /42

  $349,000

  • 2 Beds
  • 1 Bath
  • 803 Sq Ft

  1470 Flamstead Rd, Chester, VT 05143

  Beautifully set in total privacy, this cozy cabin is the perfect retreat! Nestled on a secluded, level lot, this charming home offers a peaceful escape surrounded by nature. Inside, you’ll find wide pine floors, granite countertops, and a freshly painted interior and exterior that give the space an updated feel. The spacious layout includes large rooms and a versatile loft ideal for guests, a

  Thaddeus Abare Barrett and Valley Associates Inc.

  1470 Flamstead Rd, Chester, VT 05143
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  /27

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft

  447 Elm St, Chester, VT 05143

  Welcome to your dream home – This meticulously maintained New England-style gem is bursting with charm and modern convenience. Picture yourself whipping up meals in a kitchen with custom Hugh Pennell solid wood cabinets, upgraded appliances and solid countertops. Be wowed by the beautiful hardwood floors that add warmth and character to every room.Bask in the great natural light that fills

  Lisa Kelley Cummings & Co

  447 Elm St, Chester, VT 05143
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  /21

  $215,000

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  257 Hillside Rd, Springfield, VT 05156

  Don’t miss this opportunity to own a move-in ready home in a peaceful neighborhood! Enjoy the ease of single-level living with laundry on the main floor, while the full basement provides excellent potential for additional finished space. The sellers have already added a fenced backyard, perfect for children, pets, and outdoor enjoyment. Conveniently located near Chester, North Springfield,

  Chelsea Richardson Barrett and Valley Associates Inc.

  257 Hillside Rd, Springfield, VT 05156
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  /48

  $328,000

  • 4 Beds
  • 2 Baths
  • 1,260 Sq Ft

  107 Vermont Route 100, Weston, VT 05161

  This charming saltbox cape contains four bedrooms and two bathrooms. Situated high above and overlooking the West River, this house has a level yard and year-round possibilities.An open concept main level with a wood stove, a bedroom, and a full bath. Upstairs, you'll find three additional bedrooms and a second bathroom. The unfinished full basement is your blank canvas! The backyard is

  Joseph Karl William Raveis Real Estate Vermont Properties

  107 Vermont Route 100, Weston, VT 05161
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  /39

  $599,900

  • 4 Beds
  • 3 Baths
  • 2,689 Sq Ft

  1573 Flamstead Rd, Chester, VT 05143

  You have got to see this stunning, fully renovated home, rebuilt from the studs up with meticulous attention to detail while maintaining its classic New England charm! Perfectly perched on the picturesque rolling hills of desirable Chester, this 4bdrm, 3bath beauty offers the ideal balance of comfort, elegance, and modern functionality. Set on 6 private acres overlooking open fields and peaceful

  Jamie Watson BHG Masiello Keene

  1573 Flamstead Rd, Chester, VT 05143
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  /4

  $1,495,000

  • 3 Beds
  • 4.5 Baths
  • 3,120 Sq Ft

  4070 Tichnor Rd Unit 4070, Hartford, VT 05001

  New Construction in Quechee Lakes! Introducing Mountain Stream at Quechee Lakes where modern architecture meets the natural beauty of Vermont’s premier four-season resort community. With more than 200 homesites and five distinct home styles, Mountain Stream offers thoughtfully designed residences that blend contemporary comfort with timeless surroundings. Each home features open-concept layouts,

  Richard Higgerson Higgerson & Company

  4070 Tichnor Rd Unit 4070, Hartford, VT 05001
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  /4

  $1,199,000

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft

  289 Taft Family Rd Unit 7118, Hartford, VT 05059

  New Construction in Quechee Lakes! Introducing Mountain Stream at Quechee Lakes where modern architecture meets the natural beauty of Vermont’s premier four-season resort community. With more than 200 homesites and five distinct home styles, Mountain Stream offers thoughtfully designed residences that blend contemporary comfort with timeless surroundings. Each home features open-concept layouts,

  Richard Higgerson Higgerson & Company

  289 Taft Family Rd Unit 7118, Hartford, VT 05059
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  /6

  $1,625,000

  • 5 Beds
  • 4 Baths
  • 3,837 Sq Ft

  7074 Robert Frost Ln Unit 7074, Hartford, VT 05001

  New Construction in Quechee Lakes! Introducing Mountain Stream at Quechee Lakes where modern architecture meets the natural beauty of Vermont’s premier four-season resort community. With more than 200 homesites and five distinct home styles, Mountain Stream offers thoughtfully designed residences that blend contemporary comfort with timeless surroundings. Each home features open-concept layouts,

  Richard Higgerson Higgerson & Company

  7074 Robert Frost Ln Unit 7074, Hartford, VT 05001
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  /11

  $1,525,500

  • 4 Beds
  • 4 Baths
  • 2,752 Sq Ft

  5677 Hendee Way Unit 5677, Hartford, VT 05001

  New Construction in Quechee! Introducing Mountain Stream at Quechee Lakes, where modern architecture meets the natural beauty of Vermont’s premier four-season resort community. With more than 200 homesites and five distinct home styles, Mountain Stream offers thoughtfully designed residences that blend contemporary comfort with timeless surroundings. Each home features open-concept layouts,

  Richard Higgerson Higgerson & Company

  5677 Hendee Way Unit 5677, Hartford, VT 05001
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  /58

  $1,150,000 Open Sat 11AM - 2PM

  • 4 Beds
  • 4 Baths
  • 2,640 Sq Ft

  307 Remick Rd Unit 14-27-2, White River Junction, VT 05001

  OPEN HOUSE 9/20/25 11 AM TO 2 PM: Enjoy the tranquil seclusion of this authentic colonial-style home, built in 2004 with remarkable attention to detail. Designed to mirror the craftsmanship of the period while offering the comfort, efficiency, and conveniences of modern living, this home is truly the best of both worlds. Set on 68 private acres at the end of a dead-end road, the property is

  Richard Ballou RE/MAX Upper Valley

  307 Remick Rd Unit 14-27-2, White River Junction, VT 05001
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  /24

  $399,000

  • 3 Beds
  • 2 Baths
  • 2,446 Sq Ft

  158 MacIntosh Hill Rd, Randolph, VT 05060

  Charming 1820's antique farmhouse with handcrafted cabinets and wide board floors. The home has updated systems including Viessmann on demand water heater, holding tank, pressure tank, newer electrical. Fabulous upgraded bathroom. There is a space of many uses that could be a studio, master suite, in law/guest suite. Also the most lovely screened in back sitting porch overlooking the pastures.

  Sherri McPhetres Vermont Heritage Real Estate

  158 MacIntosh Hill Rd, Randolph, VT 05060
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  $1,900,000

  • 2 Beds
  • 2.5 Baths
  • 2,944 Sq Ft

  2394 Fletcher Hill Rd, Woodstock, VT 05091

  Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is

  John Snyder Snyder Donegan Real Estate Group

  2394 Fletcher Hill Rd, Woodstock, VT 05091
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  /39

  $875,000

  • 3 Beds
  • 2.5 Baths
  • 3,088 Sq Ft

  2243 Quechee Main St, Hartford, VT 05047

  This is a quality and well cared for home with some views of surrounding area. A private lot in the village with natural light throughout the house. Spacious primary suite on living level with walk-in closet. Open living and kitchen floor plan with dining room off to side. Mud room entry laundry/utility room and half bath also on living level. Off kitchen is 15 x 20 deck with awning. Large

  Chris Crowe Quechee Lakes Real Estate Center

  2243 Quechee Main St, Hartford, VT 05047
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  /52

  $1,250,000

  • 4 Beds
  • 3.5 Baths
  • 4,177 Sq Ft

  166 Woods Rd W, Ludlow, VT 05149

  Perched high on the hillside, this home offers expansive views of the lakes and mountains. Located at the end of a quiet road in the Farm Ridge Community just under 5 miles from the base of Okemo Mountain and 4 miles to Plymouth State Park for boating and swimming in the warmer months. The maintained trails on it's 16.15 acres makes it easy to explore, while the deck is a perfect place to

  Jessica Citera Cummings & Co

  166 Woods Rd W, Ludlow, VT 05149
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  /46

  $265,000

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft

  2665 Brook Rd, Cavendish, VT 05142

  Country home ready for your vision. This 2 level, 2 bedroom, 2 bath home is located in a very pretty spot on Brooks Road in Cavendish. You are welcomed by a screened-in porch, wrap around deck,and an open kitchen/living area, with warming pellet stove. A bedroom exists on the main level and a full bath. The laundry is also located on the main level. The lower level will need your TLC to finish.

  Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

  2665 Brook Rd, Cavendish, VT 05142
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  /36

  $139,000

  • 1 Bed
  • 1 Bath
  • 240 Sq Ft

  505 Back Mountain Rd Unit 14, Windsor, VT 05089

  This beautifully crafted 2024 “Incredible Tiny Home,” built by Amish artisans, is ready for its next owner. Thoughtfully designed for efficiency and comfort, the home features a convenient kitchen, a spacious bathroom, and a loft sleeping area with stairs for easy access. A mini-split system provides both heating and cooling, ensuring year-round comfort.Step outside to enjoy the well-built

  Jenna Luce RE/MAX Upper Valley

  505 Back Mountain Rd Unit 14, Windsor, VT 05089
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  /18

  $199,000

  • 1 Bed
  • 1 Bath
  • 708 Sq Ft

  221A Southridge St, Springfield, VT 05156

  This sweet little bungalow is a true work in progress — and it’s almost ready to welcome its next owner! Whether you’re searching for your very first home, looking to downsize, or dreaming of a Vermont retreat, this property is full of charm and possibility. Thoughtful updates are well underway, including a new roof, electrical, plumbing, heating, insulation, windows, flooring, and sheetrock, so

  Linda Benoit Highland Realty

  221A Southridge St, Springfield, VT 05156
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  /58

  $2,250,000

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

  2651 Twenty Mile Stream Rd, Cavendish, VT 05142

  An unrivaled example of Snecked Ashlar building technique, built by Scottish masons back in the mid 1800's. Enjoy this completely renovated home with clever blends of modern technology, conveniences and old world country charm. Situated on renown Twenty Mile Stream Road, this home is surrounded by 172 acres featuring meadows, streams, deciduous forest and VAST access. Enter the home and you'll

  Joseph Karl William Raveis Real Estate Vermont Properties

  2651 Twenty Mile Stream Rd, Cavendish, VT 05142
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  /37

  $585,000

  • 4 Beds
  • 4 Baths
  • 3,934 Sq Ft

  46 Runnals Rd, White River Junction, VT 05001

  Step into timeless character and modern comfort in this unique 4-bedroom, 4-bathroom home. A thoughtful 1984 expansion preserved the original home's historic core featuring a rare early American beehive oven and three-hearth fireplace, while adding over 3,200 sq. ft. of spacious living and a 1,000 sq. ft. in-law apartment. There’s room for everyone here. The sun-drenched kitchen and dining area

  Cheryl Herrmann RE/MAX Group One Realtors

  46 Runnals Rd, White River Junction, VT 05001
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  /60

  $919,000

  • 5 Beds
  • 5 Baths
  • 3,886 Sq Ft

  3961 Hartland Hill Rd, Woodstock, VT 05091

  This lovely,expanded Cape sits just a half mile from Woodstock Village's East End.Surrounded by rolling green fields and wooded hillsides-this home offers a beautiful country setting less than a mile to village shopping, schools, dining and recreation. Updated with modern finishes to enhance accessibility and one level living-while maintaining the warm, country charm. First floor features a

  Tambrey Vutech KW Vermont Woodstock

  3961 Hartland Hill Rd, Woodstock, VT 05091
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  /60

  $1,450,000

  • 4 Beds
  • 4 Baths
  • 5,838 Sq Ft

  44 John Deere Dr, Ludlow, VT 05149

  Exquisite Vermont Estate with Okemo and Reservoir views! Discover refined four season Vermont living in this multi-level residence. Blending rustic elegance with modern comfort, the light-filled home showcases rich wood flooring, striking log beam accents, and a dramatic stone- backed gas fireplace as the centerpiece of its open living spaces. French doors connect the kitchen, dining and living

  Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

  44 John Deere Dr, Ludlow, VT 05149
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  /12

  $245,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  891 Vermont Route 100, Weston, VT 05161

  Charming and efficient, this 2-bedroom, 1-bath home offers a cozy retreat in the heart of Weston, Vermont. Designed for single-level living and low maintenance, the layout makes the most of its space. The main living area features an open flow between the living room and eat-in kitchen, leading to a deck that is perfect for morning coffee or outdoor grilling. Two bedrooms and a full bath complete

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  891 Vermont Route 100, Weston, VT 05161
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  /50

  $2,400,000

  • 5 Beds
  • 4.5 Baths
  • 4,832 Sq Ft

  1059 Carlton Hill Rd, Woodstock, VT 05091

  Set on over two picturesque acres along one of the most beautiful country roads in the area, this spacious and impeccably renovated contemporary farmhouse offers the perfect balance of charm and modern comfort. Just minutes from Woodstock and South Woodstock, the property enjoys both convenience and a peaceful setting.Completely remodeled in 2016 by Sargent Design Company, the home

  Keri Cole Williamson Group Sothebys Intl. Realty

  1059 Carlton Hill Rd, Woodstock, VT 05091

Showing Results 41 - 80, Page 2 of 8