Windsor County VT Homes for Sale

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  /12

  $79,000

  • 1 Bed
  • 192 Sq Ft

  324 Sunrise Rd, Bethel, VT 05032

  Located just minutes to I89 exit 3 yet off the path into the woods is this primitive camp on 10.06 acres to be developed or used as a recreational getaway. Car ready on good gravel roadway right to the property. Deed provides for septic on adjacent lot if a state approved system can be found. Access VAST trails directly or hunt right from your door. Sold As Is with furnishings and two generators

  Patricia Harvey Xsell Realty LLC

  324 Sunrise Rd, Bethel, VT 05032
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  /33

  $1,695,000

  • 5 Beds
  • 3 Baths
  • 5,086 Sq Ft

  775 E Lake Rd, Ludlow, VT 05149

  Enjoy year-round sunsets from this premier Lake Rescue location. With direct lake access, swim from your dock or launch your boat for a day on the lake. The sprawling flat yard is ideal for lakeside living, whether kicking a ball with the kids, playing badminton or for summer gatherings by the water. Recent improvements include a new 5-bedroom septic system, freshly painted exterior and main

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  775 E Lake Rd, Ludlow, VT 05149
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  /58

  $3,100,000

  • 5 Beds
  • 6 Baths
  • 4,843 Sq Ft

  66 Hollow Farm Rd, Woodstock, VT 05071

  CURTIS HOLLOW FARM- Exceptional estate on the western edge of Woodstock offering 105 diverse acres bordering Calvin Coolidge State Forest. The updated main house features 5 bedrooms and 4 baths, filled with abundant natural light and thoughtfully designed for both large gatherings and quiet retreat spaces. The open-concept main level includes a spacious living room with picture windows

  David Donegan Snyder Donegan Real Estate Group

  66 Hollow Farm Rd, Woodstock, VT 05071
• 

  

  

  /30

  $770,000

  • 3 Beds
  • 3 Baths
  • 1,820 Sq Ft

  2762 Route 12, Barnard, VT 05031

  Conveniently situated on a secluded knoll central to Woodstock Village and beautiful Silver Lake, this impeccably maintained 13.4 AC property offers privacy and convenience. The Classic Cape Home is spotless, and turn-key. The rooms are bright, and airy, with a great flow for everyday living and entertaining. The living room features a wood burning stove. The kitchen has quality appliances,

  Danny Kogut Williamson Group Sothebys Intl. Realty

  2762 Route 12, Barnard, VT 05031
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  /5

  $850,000

  • Land
  • 1.47 Acres
  • $578,231 per Acre

  97 Valley View Rd, Woodstock, VT 05091

  The justifiably proud owner of this property points out these features: Potential "Barnominium." Conveniently located just 1/4 mile from Woodstock Village town line and just 40 minutes from Killington Ski area. Built for an auto collection. Full bathroom, blown in insulation in ceiling, foam spray insulation in walls (with bug mesh in walls.) 3/4" sheet rock! All electrical is done in 3/4'

  John Wetmore Wetmore Real Estate

  97 Valley View Rd, Woodstock, VT 05091
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  /59

  $995,000

  • 6 Beds
  • 4 Baths
  • 3,052 Sq Ft

  181 Harrier Way, Plymouth, VT 05056

  Welcome to this beautifully updated Hawk home with expansive westerly mountain and valley views. Recent improvements throughout give the home a fresh, inviting feel while keeping its warm Vermont character. The renovated mudroom features custom live-edge maple walnut benches, shiplap walls, new lighting, shelving, and plenty of space for all your gear. The redesigned kitchen has granite counters,

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  181 Harrier Way, Plymouth, VT 05056
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  /60

  $510,000

  • 2 Beds
  • 3 Baths
  • 2,091 Sq Ft

  85 Townhouse Way Unit 18, Woodstock, VT 05091

  Enjoy the ease of townhouse living in this beautiful fully furnished end unit filled with natural light throughout. The setting is surrounded by woodlands and lovely landscaped grounds . The bright living room complete with wood burning fireplace steps down to a lovely kitchen with dining area .Walk out through double sliding doors onto a private deck for one of two outdoor living spaces. There

  Carol Wood Williamson Group Sothebys Intl. Realty

  85 Townhouse Way Unit 18, Woodstock, VT 05091
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  /26

  $299,900

  • 2 Beds
  • 1.5 Baths
  • 1,063 Sq Ft

  253 Old Quechee Rd Unit 6C, Hartford, VT 05001

  When we say turn-key, it is TURN-KEY! Come hang your clothes in the walk-in closet and put your feet up to enjoy this fully furnished Mill Run II condo in the beautiful Quechee Lakes community. This low-maintenance condo has been exceptionally well renovated. Some of the upgrades include: upgraded kitchen with granite counters, stainless steel appliances, wood floors, a propane push button stove

  Franchesca Collins Hall Collins Real Estate Group

  253 Old Quechee Rd Unit 6C, Hartford, VT 05001
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  /59

  $579,000

  Open Sat 11AM - 1PM

  • 4 Beds
  • 2 Baths
  • 1,914 Sq Ft

  23 Meadow View Ln, Hartland, VT 05048

  **Open House Sat 5/30/26 11a - 1p** From sunrise coffee on the deck to afternoons spent exploring nearby trails, this 4-bedroom Cape offers the space, recreation, and convenience that make Vermont living so special—all on 3 acres in Hartland and less than 30 minutes from DHMC and the Upper Valley. The main level features a kitchen that opens to the dining area and living room, creating

  Grant Tyler BHHS Verani Upper Valley

  23 Meadow View Ln, Hartland, VT 05048
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  /49

  $550,000

  • 3 Beds
  • 2.5 Baths
  • 1,724 Sq Ft

  1196 Marsh Family Rd Unit 7176, Hartford, VT 05001

  This charming chalet-style home at 1196 Marsh Family Road is beautifully sited near the top of the Marsh Family Road hill, on land once home to an apple orchard. Entertain guests on the spacious deck or gather inside around the striking living room fireplace, framed by dramatic chalet windows that fill the home with natural light. With three bedrooms and a spacious family room, made more cozy by

  Sandy Reavill

  1196 Marsh Family Rd Unit 7176, Hartford, VT 05001
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  /52

  $500,000

  • 3 Beds
  • 2 Baths
  • 2,008 Sq Ft

  352 Edwins Pond Rd, Rochester, VT 05767

  Tucked into the hills above Edwin’s Pond, this inviting Vermont home offers a rare combination of privacy, comfort, and immediate access to some of the region’s best outdoor recreation. Thoughtfully maintained and updated, the property features brand-new decks that create welcoming spaces to enjoy morning coffee, summer dinners, and the changing colors of the surrounding landscape. A new, high

  William Brokhof Vermont Backcountry Real Estate

  352 Edwins Pond Rd, Rochester, VT 05767
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  /20

  $83,000

  • Land
  • 5.4 Acres
  • $15,370 per Acre

  0 Vulture Mountain Rd, Stockbridge, VT 05772

  Two parcels offered together: The headliner is a cliffside building lot with a mesmerizing scenic view of the opposing mountains and the White River winding its way through the valley below. The second parcel sits diagonally across the road and is beneficial for utility purposes. Currently it has a well with an electrical junction box to power the pump, and this feeds fresh water to many of the

  David White OwnerEntry.com

  0 Vulture Mountain Rd, Stockbridge, VT 05772
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  /36

  $399,000

  Open Sat 12PM - 2PM Coming Soon

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

  1757 Wildlife Rd, White River Junction, VT 05001

  Privately set on 4 peaceful acres well off the road, this inviting home offers comfort, space, and a functional open-concept design. The main living area features a seamless flow between the kitchen, dining, and living spaces—ideal for everyday living and entertaining alike. A spacious mudroom entry provides practical storage and organization, complemented by a convenient laundry room and bath

  Jessica Dolan Dolan Real Estate

  1757 Wildlife Rd, White River Junction, VT 05001
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  /60

  $225,000

  • 6 Beds
  • 2 Baths
  • 2,254 Sq Ft

  761 Main St, Cavendish, VT 05153

  Character and Charm are the two things that best describe this antique village home. This prime location is walking distance to all of the great amenities Proctorsville has to offer. Including Singleton's Store Murdoch's On The Green and Outer Limits Brewery to name a few. This home has been well cared and loved for generations. Although move in ready, this home has it's quirks/character. Fully

  Frank Provance Diamond Realty

  761 Main St, Cavendish, VT 05153
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  /55

  $2,195,000

  • 5 Beds
  • 5 Baths
  • 7,374 Sq Ft

  1702 N Puckerbrush Rd, Reading, VT 05062

  Perched on a private hilltop and surrounded by nature, this stunning recently renovated home offers over 141 acres of open and wooded land enrolled in Vermont’s Current Use Forestry Program. Thoughtfully designed by Beilman Design, the residence features gracious living spaces filled with natural light and an exceptional floor plan ideal for entertaining.The handsome chef’s kitchen is

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  1702 N Puckerbrush Rd, Reading, VT 05062
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  /47

  $399,000

  • 3 Beds
  • 3 Baths
  • 2,184 Sq Ft

  1319 Brandon Mountain Rd, Rochester, VT 05767

  Set back from the highway on a gently elevated site, this beautifully maintained three-bedroom home captures sweeping views of the surrounding Green Mountains and the White River Valley. The inviting open floor plan is ideal for entertaining and relaxed family gatherings alike. The updated kitchen features attractive hardwood cabinetry, granite counters and stainless steel appliances, while the

  Kyle Kershner Killington Pico Realty

  1319 Brandon Mountain Rd, Rochester, VT 05767
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  /42

  $599,000

  • 2 Beds
  • 2 Baths
  • 2,358 Sq Ft

  141 Great Hawk Rd, Rochester, VT 05767

  Welcome to 141 Great Hawk Road! This home boasts tons of windows, soaring vaulted ceilings, hardwood floors, and a dramatic fieldstone fireplace that anchors the open-concept living space with classic Vermont charm. Gorgeous built-in cherry bookshelves, a charming sleeping loft, and sliders to an expansive sunny deck with a hot tub and seasonal views that set this beautiful home apart from its

  Cheryl Lee Tyminski Remax Summit

  141 Great Hawk Rd, Rochester, VT 05767
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  /37

  $375,000

  • 3 Beds
  • 1 Bath
  • 2,128 Sq Ft

  1057 Brockway Mills Rd, Springfield, VT 05156

  Conveniently located between Rockingham, Springfield, and Chester, this sweet 3-bedroom ranch sits on 1.5 +/- acres of mostly open, level land. The home has seen many recent upgrades, including fresh paint inside and out, beautifully refinished wood floors in select rooms, and new click-lock flooring in others. What was once attic space has been thoughtfully converted into additional finished

  Chelsea Richardson Barrett and Valley Associates Inc.

  1057 Brockway Mills Rd, Springfield, VT 05156
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  /34

  $850,000

  • 3 Beds
  • 3 Baths
  • 2,294 Sq Ft

  66 Scott's Landing, Ludlow, VT 05149

  Nestled among the trees in a serene country setting, this inviting home with walls of windows is filled with abundant natural light and offers the perfect balance of peaceful retreat and year-round recreation. Enjoy lake living with your own dock, with a dock slip, ideal for boating, relaxing, and taking in the tranquil surroundings. Located near Okemo Mountain Resort, this property is a true

  Katherine Burns William Raveis Real Estate Vermont Properties

  66 Scott's Landing, Ludlow, VT 05149
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  /56

  $1,649,000

  • 4 Beds
  • 3.5 Baths
  • 3,456 Sq Ft

  140 Echo View Dr, Ludlow, VT 05149

  Experience the perfect blend of luxury, comfort, and Vermont charm in this exceptional 3,456-square-foot home. Built with superior craftsmanship and meticulous attention to detail, this residence reflects a commitment to quality where every finish was carefully selected and thoughtfully executed. No detail was overlooked, with premium materials and high-end finishes throughout, creating a home

  Mendi Michael Engel & Völkers Okemo

  140 Echo View Dr, Ludlow, VT 05149
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  /45

  $525,000

  • 4 Beds
  • 3 Baths
  • 2,408 Sq Ft

  20 Gill Terrace, Ludlow, VT 05149

  Ideally located near Okemo Mountain Resort and the charm of the village, this highly desirable property offers both convenience and a true Vermont lifestyle. Thoughtfully updated in recent years, the home features a newer heating system, durable Hardie board siding, a standing seam metal roof, and a recently added hot tub. Spanning three levels of living space, the home offers multiple sleeping

  Katherine Burns William Raveis Real Estate Vermont Properties

  20 Gill Terrace, Ludlow, VT 05149
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  /23

  $95,000

  • 1 Bed
  • 1 Bath
  • 542 Sq Ft

  145 Main St Unit 308, Ludlow, VT 05149

  Location, location! Enjoy convenient living in the heart of the Okemo Valley on the Okemo Mountain shuttle route. This top-floor one-bedroom condominium offers an ideal in-town location close to skiing, dining, shopping, and year-round recreation. The complex is known for easy ownership with association fees that include heat and hot water. An excellent opportunity at an attractive price point.

  Katherine Burns William Raveis Real Estate Vermont Properties

  145 Main St Unit 308, Ludlow, VT 05149
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  /59

  $455,000

  • 5 Beds
  • 1.5 Baths
  • 2,205 Sq Ft

  191 Route 100 N, Ludlow, VT 05149

  Nestled between Okemo Mountain and the lakes region, this inviting 5-bedroom home sits on 2 peaceful acres framed by mature trees and an expansive open yard. Filled with warmth and character, the home is a charming reminder of simpler times, offering large sun-filled rooms and generous gathering spaces throughout. At the heart of the home is the open kitchen and family room, where a cozy wood

  Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

  191 Route 100 N, Ludlow, VT 05149
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  /60

  $2,300,000

  • 6 Beds
  • 4.5 Baths
  • 8,656 Sq Ft

  55 Cherry Hill, Springfield, VT 05156

  Steeped in history and timeless elegance, this extraordinary circa-1860 Georgian Colonial estate offers over 8,000 square feet of refined living space where classic architecture meets remarkable craftsmanship. From the moment you enter, you are greeted by stunning period details including exquisite crown moldings, grand proportions, soaring ceilings, and beautifully preserved finishes that

  Joe Castaluccio Winhall Real Estate

  55 Cherry Hill, Springfield, VT 05156
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  /59

  $495,000

  • 4 Beds
  • 3.5 Baths
  • 3,356 Sq Ft

  990 Main St, Cavendish, VT 05142

  If you're looking for the ultime village ski house look no more! This four bedroom three and a half bath TURN KEY home is nestled in the village of Proctorsville. Home to Singletons Store, Outer Limits Brewery, Murdoch's On The Green and much more walking distance away. Step into this lovely well appointed home and you'll feel right at home. The kitchen boasts granite counters with a large

  Frank Provance Diamond Realty

  990 Main St, Cavendish, VT 05142
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  /29

  $153,000

  • Land
  • 4.7 Acres
  • $32,553 per Acre

  250 Fenton Rd, Chester, VT 05143

  Welcome to a place where the sound of the river becomes part of your daily rhythm. This 4.7-acre parcel with an end-of-road location offers an extraordinary 1,400 feet of frontage on the Williams River, creating a private and tranquil retreat just five minutes from the quintessential Vermont charm of Chester Village. The land unfolds beautifully: wide, flat, sun-filled fields stretch toward the

  Rachel Febbie EXP Realty

  250 Fenton Rd, Chester, VT 05143
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  /10

  $115,000

  • Land
  • 2.58 Acres
  • $44,574 per Acre

  Lot 30 Cedar, Ludlow, VT 05149

  End of cul de sac 2.5 +/- acre lot on town sewer in well established neighborhood. Rare building lot opportunity on town sewer with close proximity to Okemo, the lakes region, golf, and village amenities.

  Andre Menard Mary W. Davis Realtor & Assoc., Inc.

  Lot 30 Cedar, Ludlow, VT 05149
• 

  

  /19

  $215,000

  • 4 Beds
  • 2 Baths
  • 1,338 Sq Ft

  16 Harlow Rd, Springfield, VT 05156

  Perfect location, nice neighborhood, near the hospital, downtown and minutes to the interstate! Featuring a first floor bed and 3/4 bath, it is perfect for aging in place. Eat in kitchen/dining convenient for those who love to cook. And, the living room is huge. Sporting a front porch, a bit of a yard and extra parking in the back, there is plenty of room for gatherings. This home still has some

  Christine Lewis Brattleboro Area Realty

  16 Harlow Rd, Springfield, VT 05156
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  /49

  $2,575,000

  • 5 Beds
  • 5.5 Baths
  • 6,716 Sq Ft

  463 North Rd, Bethel, VT 05032

  463 NORTH ROAD — Set on 45 private acres with sweeping long-range mountain views, this custom-designed five-bedroom residence offers exceptional privacy, craftsmanship, and convenience. Enjoy direct walking access to Silver Lake and Barnard Village, just 15 minutes to Woodstock and 30 minutes to Hanover and Dartmouth College.The original timber frame home is filled with warmth and natural

  John Snyder Snyder Donegan Real Estate Group

  463 North Rd, Bethel, VT 05032
• 

  

  /30

  $350,000

  • 4 Beds
  • 2 Baths
  • 1,373 Sq Ft

  35 Andover St, Ludlow, VT 05149

  This is a great opportunity. A turnkey unit in a super location in the village where you can walk to restaurants, shops, little league field and pickle ball courts all within a single block. It doesn't get any better. There are four units in the building. All of them are upstairs/downstairs unit. No chance of someone above or below you disrupting your peace and quiet. On the first level is the

  Betty McEnaney Diamond Realty

  35 Andover St, Ludlow, VT 05149
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  /8

  $399,000

  • Land
  • 22.1 Acres
  • $18,054 per Acre

  1985 Gee Hill Rd, Royalton, VT 05068

  This breathtaking parcel is ready for you to hit the ground running—literally. The driveway is in, the house site is cleared, and the sweeping mountain views are already on full display from ground level. Designed with a walk-out basement in mind, the layout is perfect for maximizing both light and landscape. Fully permitted for a 5-bedroom septic system, with a second 5-bedroom design underway

  Holly Hall Hall Collins Real Estate Group

  1985 Gee Hill Rd, Royalton, VT 05068
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  /27

  $259,000

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  250 Sand Hill Rd, Bethel, VT 05032

  Built in 2004, this well-maintained single-family home offers easy, low-maintenance living in a convenient location just minutes from downtown Bethel and local recreation fields. Situated on a hillside, the property enjoys a pleasant elevated position while remaining close to everyday amenities.The manageable yard includes a dedicated garden space — a rare find for buyers looking to grow

  Carter Auch BHHS Verani Upper Valley

  250 Sand Hill Rd, Bethel, VT 05032
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  /60

  $675,000

  • 3 Beds
  • 3.5 Baths
  • 2,936 Sq Ft

  12 Plumley Ave, Ludlow, VT 05149

  Tucked away on a dead-end road in Ludlow Village, this classic New Englander offers the rare combination of village convenience and a peaceful setting. Just minutes to Okemo Mountain Resort, local restaurants, shopping, and year-round recreation, the property is ideally located while still feeling private and removed from the activity of town. A welcoming farmer’s porch creates the perfect place

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  12 Plumley Ave, Ludlow, VT 05149
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  /33

  $750,000

  • 3 Beds
  • 1.5 Baths
  • 2,285 Sq Ft

  47 Pleasant St, Woodstock, VT 05091

  Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space downstairs (which previously has been living spacce), combined with a separate two-bedroom apartment (with its own access) upstairs. The 1,335 sf lower level (Unit C) is currently a chiropractor's office space and was previously used

  John Snyder Snyder Donegan Real Estate Group

  47 Pleasant St, Woodstock, VT 05091
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  /21

  $99,000

  • Land
  • 1.52 Acres
  • $65,132 per Acre

  0 Gold Coast Rd Unit 5089928, Bridgewater, VT 05035

  For many years the owners have enjoyed the serenity of this beloved campsite, as their Vermont Summer retreat. Now the time has come to pass their property on, for new owners to establish vacation memories of their own. The 1.5 acre parcel is wonderfully diverse! Near the height of the land an open area could well be the site for constructing a cabin. When facing South from this area a pleasant

  John Wetmore Wetmore Real Estate

  0 Gold Coast Rd Unit 5089928, Bridgewater, VT 05035
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  /41

  $5,150,000

  • 8 Beds
  • 7.5 Baths
  • 10,062 Sq Ft

  3800 Weston-Andover Rd, Andover, VT 05143

  Escape to Moosewalk Lane. This ultimate family compound is a fully furnished and equipped rural retreat in Andover, Vermont. Set on 384 acres rising to 2,200 feet, the tract blends seclusion and timeless craftsmanship, with miles of private trails for winter sports, horseback riding and recreational vehicles, all threading through open meadows, historic stone walls, and woodlands, with direct

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  3800 Weston-Andover Rd, Andover, VT 05143
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  /57

  $3,749,000

  • 5 Beds
  • 5.5 Baths
  • 8,122 Sq Ft

  5685 Vermont 12, Barnard, VT 05031

  “HIGHLAND GLEN” – Rarely does a property capture the essence of Vermont as beautifully as Highland Glen. Set on twelve picturesque acres in the charming town of Barnard, this extraordinary estate blends timeless New England character with exceptional comfort, privacy, and recreation.Arrive by the iconic red barn and discover stunning gardens, apple orchard, meandering stone walls, flowing

  John Snyder Snyder Donegan Real Estate Group

  5685 Vermont 12, Barnard, VT 05031
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  /58

  $749,000

  • 3 Beds
  • 3 Baths
  • 2,697 Sq Ft

  1641 W Hill Rd, Rochester, VT 05767

  Welcome to The Birches — a peaceful end-of-road retreat where serenity, privacy, and Vermont’s natural beauty come together. Surrounded by more than 7,000 acres of conserved national forest land, this exceptional property offers unmatched tranquility, abundant wildlife, and direct access to outdoor adventure in every season.Set in a quiet mountain setting, this thoughtfully designed

  Brandon Fowler RE/MAX North Professionals

  1641 W Hill Rd, Rochester, VT 05767
• 

  

  /19

  $250,000

  • 2 Beds
  • 1 Bath
  • 968 Sq Ft

  133 Colonial Dr Unit 403, White River Junction, VT 05001

  *OFFER DEADLINE - 5/26 AT 5PM* Welcome to Oak Knoll Condominiums in White River Junction, VT. This 2 bedroom, 1 bathroom condo has been well updated and is ready for its next owner. New flooring on both levels, new appliances, and a custom laundry closet. The furnace is under four years old and the hot water tank was replaced two years ago, so the big ticket items are already done. Come check out

  Devin Josler Black House Real Estate

  133 Colonial Dr Unit 403, White River Junction, VT 05001
• 

  

  /36

  $449,000

  $30K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,094 Sq Ft

  75 Naulahka Ln, Hartford, VT 05059

  This Quechee retreat feels like a tree house. Combining three lots provides a level of privacy that is becoming increasingly rare in the Upper Valley, and the vertical layout makes excellent use of that wooded backdrop.By placing the Great Room behind two large picture windows, the design creates a seamless visual transition between the interior and the forest canopy.With a bedroom and full bath

  Linda Hicks Quechee Lakes Real Estate Center

  75 Naulahka Ln, Hartford, VT 05059

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