Windsor County VT Houses for Sale

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  /33

  $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

  (802) 499-2434

  158 MacIntosh Hill Rd, Randolph, VT 05060
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  /58

  $1,400,000

  • 6 Beds
  • 5 Baths
  • 4,571 Sq Ft

  505 Deweys Mills Rd, Hartford, VT 05047

  The Dewey House joins timeless elegance with contemporary convenience. Situated on a quiet road adjacent to the Quechee Gorge waterfall in the charming town of Quechee, this property offers easy access to I-89, I-91, and Route 4. Nearby walking trails and direct water access lend themselves to outdoor pursuits, while the views from the house and its decks over the mill pond and hills create the

  

  Jennifer Falvey

  KW Vermont Woodstock

  (877) 419-4767

  505 Deweys Mills Rd, Hartford, VT 05047
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  /43

  $425,000

  • 5 Beds
  • 2 Baths
  • 1,982 Sq Ft

  176 Meadow Rd, Chester, VT 05143

  The Best of Both Worlds: Modern Comfort Meets Village Charm!Discover the perfect blend of contemporary upgrades and serene neighborhood. This meticulously updated raised ranch offers an expansive layout designed for both effortless entertaining and comfortable daily living.Step inside to find a light-filled open-concept living and dining area, anchored by stunning hickory hardwood floors

  

  Lauren Behm

  Berkshire Hathaway HomeServices Stratton Home

  (802) 416-3199

  176 Meadow Rd, Chester, VT 05143
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  /50

  $1,189,000

  • 5 Beds
  • 2.5 Baths
  • 2,662 Sq Ft

  63 Shiloh Ln, Norwich, VT 05055

  Tucked away on quiet Shiloh Lane in Norwich, VT, this exceptional 21.5-acre property offers a rare blend of privacy, usable land, and convenience—just minutes from Hanover and Dartmouth. The park-like setting features landscaped grounds, walking trails, garden areas, a greenhouse, a five-stall horse barn, and two potential pond sites—ideal for equestrian use, hobby farming, or enjoying Vermont’s

  

  Melissa Robinson

  Coldwell Banker LIFESTYLES - Hanover

  (802) 200-2465

  63 Shiloh Ln, Norwich, VT 05055
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  /21

  $75,000

  • 1,440 Sq Ft

  178 Church St, Bethel, VT 05032

  Looking for a Summer Project? Put your ambition and skills to work in this unfinished, single-story 30' x 24'+ wood framed shell constructed with beefy rough-cut lumber. Electric service provided by Green Mountain Power (meter on building). Public water service to, and public sewage disposal from, are available on site. Currently, there is no electrical wiring, plumbing pipes, nor fixtures, but

  

  Lori Holt

  BHHS Vermont Realty Group/Montpelier

  (802) 330-8205

  178 Church St, Bethel, VT 05032
• 

  

  /47

  $1,895,000

  • 3 Beds
  • 1 Bath
  • 1,708 Sq Ft

  196 Cowdrey Outlook, Bethel, VT 05032

  For the first time in over half a century, this extraordinary 100+ acre estate-level property in Barnard is being offered for sale. Cherished by the same family for generations, the property presents a rare opportunity to own one of Vermont’s most scenic and versatile landscapes. Commanding long-range mountain views define the setting, while several picturesque spring-fed ponds, rolling meadows,

  

  Susan Hickey

  Snyder Donegan Real Estate Group

  (802) 284-4197

  196 Cowdrey Outlook, Bethel, VT 05032
• 

  

  /17

  $239,000

  • 4 Beds
  • 2 Baths
  • 2,111 Sq Ft

  135 Wall St, Springfield, VT 05156

  Large, in town family home. Lots of room to spread out, 1st floor laundry, formal dining room, first floor bedroom, open second floor landing makes for a great space for a workspace, tv space or reading nook. All rooms are generous in size; large covered front porch makes for great place to hang out in rain or shine. Covered side entry into the home for convenience right off the driveway. Please

  

  Julie Buffum

  Buffum Realty

  (802) 613-9305

  135 Wall St, Springfield, VT 05156
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  /54

  $2,599,000

  • 9 Beds
  • 11 Baths
  • 5,993 Sq Ft

  41 Pleasant St, Woodstock, VT 05091

  This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont’s most beloved communities. Woodstock is often hailed as “the prettiest small town in America,” and for good reason. The village is a vibrant resort town with

  

  Jennifer Falvey

  KW Vermont Woodstock

  (802) 347-9544

  41 Pleasant St, Woodstock, VT 05091
• 

  

  /29

  $349,000

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

  447 Elm St, Chester, VT 05143

  Welcome to your dream home – This meticulously maintained and efficient New England-style gem is bursting with charm and modern convenience. Extra insulation, new windows and new hot water heater make this home as energy-efficient as it is beautiful. Picture yourself whipping up meals in a kitchen with custom Hugh Pennell solid wood cabinets, upgraded appliances and solid countertops. Be wowed by

  

  Lisa Kelley

  Cummings & Co

  (802) 200-2452

  447 Elm St, Chester, VT 05143
• 

  

  /41

  $1,495,000

  • 4 Beds
  • 1.5 Baths

  7 Slayton Terrace, Woodstock, VT 05091

  A rare in-village offering, 7 Slayton Terrace combines walkability, views, and beautifully renovated interiors—just steps from the heart of Woodstock. Sited on an oversized .79-acre lot overlooking Billings Farm, this 4-bedroom home offers the space and flexibility rarely found so close to the village center. The main house features a stunning new kitchen with high-end finishes and beautifully

  Keri Cole Williamson Group Sotheby's International Realty

  7 Slayton Terrace, Woodstock, VT 05091
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  /33

  $1,895,000

  • 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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  /44

  $849,900

  • 3 Beds
  • 3 Baths
  • 3,392 Sq Ft

  117 Horseshoe Dr, Brownsville, VT 05037

  Experience Vermont living at its finest in this custom-built home, thoughtfully designed by the builder for exceptional energy efficiency and year-round comfort. Perfect as a relaxing getaway, this property offers expansive sleeping spaces ideal for hosting family and friends. Spend your days exploring the nearby VAST Trail system or Ascutney Mountain, and your evenings unwinding by the

  Katie Ladue Gilbert BHHS Verani Upper Valley

  117 Horseshoe Dr, Brownsville, VT 05037
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  /60

  $2,450,000

  • 5 Beds
  • 6 Baths
  • 5,625 Sq Ft

  16 Olcott Rd, Norwich, VT 05055

  16 OLCOTT ROAD- Elegant, spacious, and immaculate reproduction colonial constructed by premier builder Douglas Gest in an idyllic location minutes to Norwich Village yet privately set with lovely westerly views. This gorgeous home is well-appointed, bright, and has fine finish work at every turn. The main level flows effortlessly from a spacious kitchen and pantry to open concept dining and

  David Donegan Snyder Donegan Real Estate Group

  16 Olcott Rd, Norwich, VT 05055
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  /53

  $595,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 2 Baths
  • 2,966 Sq Ft

  147 Pleasantview Ln, Chester, VT 05143

  Tucked away at the end of a quiet lane on three scenic acres, this well-maintained home offers a rare blend of privacy, versatility, and proximity to town. Set against the backdrop of the Williams River, the property delivers a peaceful setting with year-round interest: mature apple trees, open lawn, and seasonal views best enjoyed from the expansive back deck. Inside, over 2,500 square feet of

  Jay Farrar Four Seasons Sotheby's Int'l Realty

  147 Pleasantview Ln, Chester, VT 05143
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  /34

  $224,500

  • 2 Beds
  • 1 Bath
  • 1,356 Sq Ft

  15 Grove St, Springfield, VT 05156

  Tucked at the base of a quiet wooded hill in Springfield, this 1918 cottage has lived over a century and arrived at this moment looking its very best. It is the kind of home where original hardwood floors greet you at the door, where light through newer windows finds its way across fresh neutral paint, and where a pair of whimsical under-stair nooks sit beneath the staircase like a wink from

  Nick Sicard EXP Realty

  15 Grove St, Springfield, VT 05156
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  /38

  $895,000

  • 4 Beds
  • 1.5 Baths
  • 1,580 Sq Ft

  51 River St, Woodstock, VT 05091

  Beautiful residence with newer renovations...located in the heart of historic Woodstock. Sunlit rooms, open floor concept with handsome refinished original pine floors. Stunning kitchen with stainless appliances, oversized island and soapstone counters accent the new cabinetry. Large dining room for entertaining with lovely screened in porch with double doors that lead out to a privately enclosed

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  51 River St, Woodstock, VT 05091
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  /24

  $474,800

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft

  586 Ski Tow Rd, Brownsville, VT 05037

  Adorable partially furnished 3 bedroom, 2 bath home on landscaped 1.53 acres corner lot in the heart of Ascutney Mt Resort! Many upgrades including Bosch High Efficiency Propane Boiler, Mitsubishi heat pump/AC, Rinnai on demand hot water heater, new well tank & centrifuge filtration system, new fireplace & chimney with Woodstock soapstone woodstove flanked by custom cabinets on each side. Decks,

  Dana Waters Dark Horse Realty

  586 Ski Tow Rd, Brownsville, VT 05037
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  /43

  $359,000

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft

  919 Vt Route 100 S, Rochester, VT 05767

  Set on a sun-drenched, level lot, this beautifully updated ranch offers effortless living with modern upgrades throughout. Recent improvements include new electrical and heating systems, a water heater, insulation, siding, doors, and double-pane windows—providing both comfort and efficiency. Inside, you’ll find warm hardwood floors, recessed lighting, and a spacious, inviting kitchen perfect for

  Christopher King King Real Estate

  919 Vt Route 100 S, Rochester, VT 05767
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  /19

  $525,000

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

  175 Pleasant Valley Rd, Springfield, VT 05156

  Welcome to your own peaceful, private homestead. Set on 7.5 acres of wooded and open land this property is truly a respite from the stresses of the world. This multi-level 3-bedroom, 3 bath home offers convenience and options. The spacious living room with hardwood floors leads to a large eat-in kitchen with ample storage and room for an island if desired. Step into the Family room or a large

  Carol Cole BHG Masiello Brattleboro

  175 Pleasant Valley Rd, Springfield, VT 05156
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  /14

  $89,000

  • 2 Beds
  • 1 Bath
  • 1,670 Sq Ft

  1526 Old River Rd, Hartford, VT 05001

  This 2 bedroom/1 bath home with 1,670 sq ft on 6.7 wooded acres in the White River Junction area. The interior offers a functional layout with a kitchen featuring wood cabinets, laminate countertops, and tile flooring, a living area with a wall-mounted heater, and a half bath with tile flooring, providing a solid starting point for updates and customization to suit your vision. Set on a hillside,

  Derek Greene Derek Greene

  1526 Old River Rd, Hartford, VT 05001
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  /48

  $500,000

  • 3 Beds
  • 2.5 Baths
  • 1,558 Sq Ft

  501 Stoughton Pond Rd, Perkinsville, VT 05151

  Tucked into the charming village of Perkinsville on 3.8 acres, this unique residential and commercial property offers the perfect balance of opportunity, lifestyle, and connection. You will be moments away from Stoughton Pond, hiking trails, and within driving distance to some of Vermont’s most sought-after ski resorts. For years, this property has been a gathering place—Saturday nights around

  Marie Potter EXP Realty

  501 Stoughton Pond Rd, Perkinsville, VT 05151
• 

  

  /50

  $325,000

  • 4 Beds
  • 2 Baths
  • 2,520 Sq Ft

  2218 Main St, Cavendish, VT 05142

  Terrific village home with bright, open living spaces! This property offers the perfect backdrop for sun-drenched days, featuring charming gingerbread trim and a unique, versatile room above the porch. As you enter through the welcoming sunroom, you’ll immediately enjoy the airy, open layout that connects the sunroom, dining room, and kitchen—perfect for breezy, seasonal gatherings. The first

  Jill Lawrence The Real Estate Collaborative

  2218 Main St, Cavendish, VT 05142
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  /51

  $719,000

  • 3 Beds
  • 2.5 Baths
  • 2,019 Sq Ft

  455 Hawk Pine Rd, Norwich, VT 05055

  Well cared for energy efficient three bedroom two+ bath cape in a wonderful country setting! Set on 1.38 acres of gorgeously landscaped grounds, this home is a six minute drive to Marion Cross School and Norwich’s favorite store, Dan & Whit’s. Ten minutes to Dartmouth College. Norwich is part of the Dresden interstate School District and students attend Hanover for middle and high school. The

  Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  455 Hawk Pine Rd, Norwich, VT 05055
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  /60

  $3,350,000

  • 5 Beds
  • 5 Baths
  • 3,212 Sq Ft

  166 Jewett Rd, Brownsville, VT 05037

  Stately hilltop home built by Silas Banister c.1800, recently undergone a complete restoration. Quality materials & craftsmanship throughout. It has gorgeous views of nearby Ascutney Mountain & long-range views of NH. The property consists of 98 acres made up of fields, hard & softwoods, trails, a large sugarbush (potential for a future boiling operation). Conserved by Upper Valley Land Trust,

  Dana Waters Dark Horse Realty

  166 Jewett Rd, Brownsville, VT 05037
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  /26

  $309,000

  • 3 Beds
  • 3 Baths
  • 1,594 Sq Ft

  70 Mountains Edge Rd Unit 606, West Windsor, VT 05037

  Tucked away from the other buildings, this unique three-bedroom, three-bath condominium offers a peaceful setting with wooded views from all three private balconies. Thoughtfully remodeled, the home features newer hardwood flooring, updated carpeting, and tastefully renovated bathrooms. The open-concept main level includes a comfortable kitchen with a breakfast bar, a dedicated dining area, and

  Gerry Stark RE/MAX Upper Valley

  70 Mountains Edge Rd Unit 606, West Windsor, VT 05037
• 

  

  /13

  $172,900

  • 3 Beds
  • 2 Baths
  • 1,359 Sq Ft

  136 Store Hill Rd, Bethel, VT 05032

  Property being sold "AS IS".State septic permitting is in progress. Located in quaint E. Bethel Village, this 1825 farmhouse offers an opportunity to finish to your taste.

  Dean Goulet Dunrovin Real Estate

  136 Store Hill Rd, Bethel, VT 05032
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  /59

  $930,000

  • 4 Beds
  • 2.5 Baths
  • 2,352 Sq Ft

  567 Churchill Rd, Brownsville, VT 05037

  Discover a truly rare opportunity to own an extraordinary piece of Vermont countryside. This 4-bedroom, 3-bath home is set on 80 acres of pristine woodland with nearly a full mile of road frontage for exceptional accessibility and future potential. Lovingly held by the same family for over 60 years, the property is rich in history, with classic stone wall boundary lines that echo its past. This

  Julie Davis KW Vermont Woodstock

  567 Churchill Rd, Brownsville, VT 05037
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  /17

  $99,000

  • 3 Beds
  • 1 Bath
  • 1,069 Sq Ft

  284 Kirk Meadow Rd, Springfield, VT 05156

  Investor special with strong value add potential! This property already has key improvements underway, including sections of new sheetrock and refinished hardwood floors saving time and upfront renovation costs. The layout includes a desirable three-season porch, adding usable space and storage. The property features a drilled well and private septic, with a nice lot offering privacy and

  Thaddeus Abare Barrett and Valley Associates Inc.

  284 Kirk Meadow Rd, Springfield, VT 05156
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  /50

  $650,000

  • 3 Beds
  • 4 Baths
  • 3,336 Sq Ft

  2145 Tarbell Hill Rd Unit 20, Cavendish, VT 05142

  Beautiful Cape-style home set in picturesque Cavendish, Vermont, offering a seamless blend of modern design and Craftsman-quality finishes. This thoughtfully designed home features a striking dual fireplace and a unique dual-access kitchen with counters on both sides—ideal for entertaining. The kitchen is equipped with stainless steel appliances, including a gas stove, perfect for the home chef.

  Cyd Scott Cohn & Company

  2145 Tarbell Hill Rd Unit 20, Cavendish, VT 05142
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  /60

  $525,000

  • 4 Beds
  • 1.5 Baths
  • 2,238 Sq Ft

  30 Vermont Route 12, Hartland, VT 05048

  Classic 1880 New Englander set on a level 1 acre lot in downtown Hartland. Walk to everything! This 1.75-story Cape offers approximately 2,238 SF with 4 Bedrooms and a welcoming wraparound covered porch that adds both charm & functional outdoor living space. Interior features include a traditional layout with a nice flow from room to room. The Laundry/Mudroom area provides pantry storage and easy

  John Bassette Bassette Real Estate Group

  30 Vermont Route 12, Hartland, VT 05048
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  /59

  $455,000

  • 4 Beds
  • 3 Baths
  • 2,352 Sq Ft

  200 Lambert Rd, Springfield, VT 05156

  Tucked into a peaceful Springfield neighborhood, this spacious 4-bedroom, 3-bathroom home combines comfort, style, and a host of recent upgrades. Set on a serene lot with local views, the property features a brand-new roof on both the house and garage, a newly installed woodstove, and a new chimney liner and masonry, perfect for cozy evenings. The brand-new septic system adds peace of mind, while

  Lucas deSousa Vermont Real Estate Company

  200 Lambert Rd, Springfield, VT 05156
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  /51

  $895,000

  • 4 Beds
  • 4 Baths
  • 2,528 Sq Ft

  132 Loveland Hill Rd, White River Junction, VT 05001

  Set high on a south-facing hillside in Hartford, Vermont—just fifteen minutes from Dartmouth College and downtown Hanover, yet a world away—132 Loveland Hill Road is a striking contemporary defined by its dramatic A-frame glass curtain wall. Floor-to-ceiling glazing fills the cathedral-ceilinged living space with natural light and frames long views across the surrounding woodland, with the peak

  Richard Higgerson Higgerson & Company

  132 Loveland Hill Rd, White River Junction, VT 05001
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  /60

  $1,150,000

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

  764 Upper Sparrow Hawk Rd, Rochester, VT 05767

  Where Mountain Living Meets Modern Design. Set on 7.3± private acres in the heart of Vermont’s premier ski country, this extraordinary retreat offers a rare blend of refined luxury and natural beauty. Thoughtfully renovated and expanded, the home showcases over 2,500 finished square feet of curated living space with sweeping views of Killington and Pico, and seasonal glimpses of Camel’s Hump and

  The Hammond Team KW Vermont

  764 Upper Sparrow Hawk Rd, Rochester, VT 05767
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  /20

  $405,000

  • 576 Sq Ft

  126 Red Bridge Rd, Ludlow, VT 05149

  Welcome to the ULTIMATE Summer Camp! With 430 feet of shoreline access where you'll have a gateway way to the lakes. From your frontage you have direct access to the Red Bridge Spillway with easy swimming access to Lake Rescue or portage over your canoe, kayak or paddle board. The flat yard and wooded buffer from the road gives this property the feel of a private Idaho. Enjoy endless summer days

  Frank Provance Diamond Realty

  126 Red Bridge Rd, Ludlow, VT 05149
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  /39

  $849,000

  • 4 Beds
  • 4 Baths
  • 2,534 Sq Ft

  732 Bridgewater Center Rd, Bridgewater Corners, VT 05035

  Turn-key mountain retreat just minutes from Killington or Woodstock! Completely renovated 4-bedroom, 4-bath home blends modern updates with classic Vermont character - featuring an updated kitchen, new bathrooms, a large mudroom with built-in ski storage, and scenic mountain views showcased by oversized custom windows that fill the home with natural light. Multiple living spaces and the expansive

  Alex Shaffer Four Corner Properties LLC

  732 Bridgewater Center Rd, Bridgewater Corners, VT 05035
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  /52

  $847,000

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

  303 Woodbury Rd, 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, Springfield, VT 05156
• 

  

  /40

  $500,000

  • 3 Beds
  • 2.5 Baths
  • 1,268 Sq Ft

  20 Edwins Pond Rd, Rochester, VT 05767

  Set on a quiet, rural corner lot just off Middle Hollow Road, this contemporary Vermont home offers a compelling blend of efficiency, flexibility, and long-term upside. Built in 1989 with a durable standing seam metal roof and solid wood-frame construction, the home provides 3+ bedrooms and 2.5 baths across a thoughtfully scaled footprint, with additional finished space in the walkout lower

  William Brokhof Vermont Backcountry Real Estate

  20 Edwins Pond Rd, Rochester, VT 05767
• 

  

  /24

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,992 Sq Ft

  37 Dee Haven, Sharon, VT 05065

  Looking to start your investment portfolio? This property is a great place to start, with opportunity to purchase two additional units that share the septic. In a quiet Sharon cul-de-sac, this property has two, two-bedroom units, one on each floor. Newer roof, newer shared septic, poured concrete foundation. Lot includes 10 acres of land that abuts land owned by the VT Dept. of Fish & Wildlife,

  Devin Josler Black House Real Estate

  37 Dee Haven, Sharon, VT 05065
• 

  

  /25

  $339,000

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

  74 Union St, Windsor, VT 05089

  Discover space, flexibility, and everyday convenience in this charming 4-bedroom, 2-bath home in the heart of Windsor. Thoughtfully designed with a spacious floor plan, the main living area features warm hardwood floors and abundant natural light, creating a bright and welcoming atmosphere throughout. The formal dining area flows seamlessly into the living room, perfect for both everyday living

  Chelsea Bevis KW Vermont Woodstock

  74 Union St, Windsor, VT 05089
• 

  

  /47

  $649,900

  • 4 Beds
  • 4 Baths
  • 2,904 Sq Ft

  5 Malagash Rd, South Reading, VT 05153

  Tucked within the peaceful hamlet of South Reading, this inviting property offers a lifestyle where the pace slows, and everyday living feels a bit more enjoyable. Set on over three acres, this spacious four-bedroom, four-bath home combines comfort, functionality, and natural beauty. The true highlight is the backyard oasis—featuring a tranquil pond, a generous deck ideal for entertaining, a

  Kevin Barnes William Raveis Real Estate Vermont Properties

  5 Malagash Rd, South Reading, VT 05153

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