Windsor County VT Homes for Sale

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  /52

  $849,000

  • 4 Beds
  • 4.5 Baths
  • 4,009 Sq Ft

  320 Old Bow Rd, Springfield, VT 05156

  Tucked away on a private road in Weathersfield, this property offers nearly 14 acres of open land, big sky, and clear views of Ascutney Mountain. A good portion of the land has already been cleared and is currently home to farm animals, so there is a head start here if that lifestyle appeals to you. You can keep it going as it is, expand into something more, or simply enjoy the open land for the

  

  Patrick Kelley

  Real Broker LLC

  (802) 392-2795

  320 Old Bow Rd, Springfield, VT 05156
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  /47

  $549,000

  $20K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,464 Sq Ft

  3341 Trebo Rd, Chester, VT 05143

  Set along a quiet country road, this inviting 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and Vermont charm. The open-concept layout features high ceilings and abundant natural light, creating a warm, airy feel throughout. A spacious primary suite includes a jetted tub and walk-in closet, providing a true retreat at day’s end. Step outside to a sunny, open lot with a

  Daire Gibney Barrett and Valley Associates Inc.

  3341 Trebo Rd, Chester, VT 05143
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  /41

  $349,000

  • 2 Beds
  • 2 Baths
  • 1,288 Sq Ft

  31 Northfield Dr, North Springfield, VT 05150

  First time on market! This custom-built home has had only one owner. Shows like a new home. The owners have meticulously maintained this home and are ready to pass it on for its next chapter. Situated in a neighborhood in North Springfield just off the beaten path you'll enjoy the neighborhood, great area for walking and nature is literally out your back door. This home features an efficient

  

  Julie Buffum

  Buffum Realty

  (802) 200-2986

  31 Northfield Dr, North Springfield, VT 05150
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  /60

  $1,300,000

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

  366 Knapp Pond Rd, Cavendish, VT 05142

  Did I read that right? 172 acres?! Impeccably renovated farmhouse on +-172 acres - what more could you ask for? ~131 acres of this property are located in Cavendish while the other ~41 are in Reading. Enjoy apples straight from the backyard. Listen and watch the brook babble down by the road and enjoy the peace that comes from this lovely home. All new Marvin Elevate windows, all new appliances,

  Franchesca Collins Hall Collins Real Estate Group

  366 Knapp Pond Rd, Cavendish, VT 05142
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  /60

  $2,495,000

  • 5 Beds
  • 9 Baths
  • 7,322 Sq Ft

  1497 Bowman Rd, Barnard, VT 05068

  Circa 1799 Vermont cape, thoughtfully restored and expanded to over 7,300 finished square feet on 12.5 private acres, minutes to Silver Lake and Woodstock village. Five bedrooms, nine baths, and a layout that balances everyday living with the ability to host. Original materials carry throughout, including wide pine floors, skim-coat plaster walls, hand-carved paneling, and period hardware, giving

  Richard Higgerson Higgerson & Company

  1497 Bowman Rd, Barnard, VT 05068
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  /46

  $1,325,000

  • 4 Beds
  • 2 Baths
  • 2,554 Sq Ft

  325 Cemetery Rd, West Windsor, VT 05089

  Farm at Gaelic Crossing is an equestrian property set on 26.72± acres, has dramatic views of Mount Ascutney and, after summer showers, the frequent and magical appearance of rainbows—often even double rainbows—across the wide, open sky. This updated c.1842 New England Cape offers 2,554 square feet of finished living space, including four bedrooms—two conveniently located on the first floor. Wide

  Story Jenks LandVest, Inc/Woodstock

  325 Cemetery Rd, West Windsor, VT 05089
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  /41

  $550,000

  • 3 Beds
  • 2 Baths
  • 1,939 Sq Ft

  105 Craigue Hill Rd, Springfield, VT 05156

  Located on 17 acres, but close to schools, shopping, medical services and recreation, this property offers privacy, views and a pond. This property also enjoys a beautiful guest house for visitors or a long-term rental. The main house is a traditional cape style with an abundance of porches for viewing wildlife. The entrance foyer and sitting area leads to the living room and the large dining

  Carol Cole BHG Masiello Brattleboro

  105 Craigue Hill Rd, Springfield, VT 05156
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  /59

  $1,690,000

  • 10 Beds
  • 8 Baths
  • 7,566 Sq Ft

  156 Main St, Ludlow, VT 05149

  In the heart of the ever-popular Ludlow, Vermont, sits an 11,409 square foot commercial building with 7,566 square feet of finished space. Built in 1990, it is situated in a prime location on Main Street in the center of the village providing it with excellent visibility, walkability, and proximity to Ludlow’s charming boutiques and local dining. It is full of investment possibilities with seven

  John Napier TPW Real Estate

  156 Main St, Ludlow, VT 05149
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  /55

  $399,000

  • 2 Beds
  • 1 Bath
  • 1,024 Sq Ft

  1013 Jericho Rd, White River Junction, VT 05001

  Wonderful Ranch style home conveniently located on the picturesque Jericho Road in Hartford VT. This two bedroom, one bath home situated on 2.9 +/- acres radiates warmth and hospitality and could be perfect for buyers looking for single level living! This is a rare opportunity to own a more affordable home in the Jericho district. This unique home has been totally renovated / updated over the

  Alex DeFelice The Clerkin Agency, P.C.

  1013 Jericho Rd, White River Junction, VT 05001
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  /46

  $1,195,000

  $130K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,913 Sq Ft

  177 Old Tavern Rd, Weston, VT 05161

  Renovated in 2024, this timber frame sits on 5.75 pastural acres. This property offers sunrise views, beautiful sun all day and a peaceful setting with pond on a quiet country road. The house has 3 bedrooms, 3 full baths, and an office. Wide plank original pine floors, open timber frame concept and all new baths with heated floors. Custom white oak cabinets in the kitchen and baths, with

  Jessica Marullo TPW Real Estate

  177 Old Tavern Rd, Weston, VT 05161
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  /4

  $250,000

  • Land
  • 8.95 Acres
  • $27,933 per Acre

  3803 Vermont Route 132, Sharon, VT 05065

  COME AND CHECK OUT THIS SPECTACULAR PROPERTY WHERE YOU CAN BUILD YOUR DREAM HOME. THE PRIVATE SHARED ROAD TO THE PARCEL IS COMPLETE. FANTASTIC VIEWS OF THE GREEN MOUNTAINS. QUICK ACCESS TO NORWICH VIA BEAVER MEADOW RD. OR I 89 JUST DOWN THE ROAD. PRETTY LEVEL AT THE CLEARED TOP. VERY QUIET AND PEACEFUL SPOT. NEW SEPTIC DESIGN IN HAND.

  Liam McCarthy Coldwell Banker LIFESTYLES - Hanover

  3803 Vermont Route 132, Sharon, VT 05065
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  /10

  $229,000

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  29 National St, Windsor, VT 05089

  Take a look at this rare chance to own a BRAND NEW home in the heart of Windsor. Built for efficiency, the house features a raised foundation to keep it out of the flood zone for extra peace of mind. The layout is practical and spacious, offering an open-concept first floor and large bedrooms upstairs.You are within walking distance to the Amtrak station and downtown, and our local Moover

  Chelsea Bevis KW Vermont Woodstock

  29 National St, Windsor, VT 05089
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  /13

  $229,000

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  15 National St, Windsor, VT 05089

  Experience the rare opportunity to own a BRAND NEW home, located in the heart of Windsor. This home seamlessly blends efficiency with style, featuring a thoughtfully elevated foundation designed to sit securely out of the flood zone for total peace of mind. The interior offers open living on the first level, and generous sized bedrooms upstairs, maximizing all the available space. The exterior

  Chelsea Bevis KW Vermont Woodstock

  15 National St, Windsor, VT 05089
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  /19

  $345,000

  • Land
  • 6.48 Acres
  • $53,241 per Acre

  0 Oakridge Way, Woodstock, VT 05091

  Your dream home starts right here — with a blank canvas in one of Vermont's most coveted communities. This exceptional buildable lot on Oak Ridge Way presents a rare opportunity to design and construct your ideal residence on a quiet side road in Woodstock. Nestled within a highly sought-after neighborhood, surrounded by million dollar homes, this property offers the kind of setting that inspires

  Nancy Greenwood Watson Realty & Associates

  0 Oakridge Way, Woodstock, VT 05091
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  /60

  $474,900

  $24K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  547 Williams Rd, Chester, VT 05143

  MOTIVATED SELLERS welcome you to this meticulously maintained chalet in gorgeous Chester, Vermont! Private and secluded, direct access to VAST, located less than an hour from six renowned ski resorts and amenities. So many updates in the past two years; fully remodeled kitchen and bathrooms, fresh paint, new flooring along with numerous updates (list attached in associate documents); modern and

  Terri Edgerley Edge Realty Vermont

  547 Williams Rd, Chester, VT 05143
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  /48

  $527,000

  • 4 Beds
  • 2.5 Baths
  • 1,824 Sq Ft

  88 Happy Valley Rd, Woodstock, VT 05091

  Step into a rare offering where timeless New England charm meets contemporary comfort. Originally built in 1846 and thoughtfully reimagined, this exceptional Taftsville, Vermont residence is set along Happy Valley Brook, creating a private sanctuary defined by peace, beauty, and understated elegance. Historic character is beautifully complemented by carefully curated upgrades, including

  Julie Davis KW Vermont Woodstock

  88 Happy Valley Rd, Woodstock, VT 05091
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  /6

  $189,900

  • 3 Beds
  • 2 Baths
  • 980 Sq Ft

  28 Thetford Ln, Bethel, VT 05032

  On owned land 3 bedroom two bath mobile home on a concrete pad. 1.64 acres surveyed land. owner will consider owner financing with first mortgage. owner can help with qualifying. occupancy at closing. home has stand and seam metal roof, 2 sheds. estimated payment is 1,544.00 / month depending on rate, down payment etc.

  Derek Greene Derek Greene

  28 Thetford Ln, Bethel, VT 05032
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  /13

  $189,000

  • Land
  • 1.7 Acres
  • $111,176 per Acre

  0 Meadow Ln, Hartford, VT 05001

  This 1.7-acre parcel on Meadow Lane offers a great opportunity to build in a quiet Hartford setting while still being close to everything the Upper Valley has to offer. The lot is tucked away at the end of the road, providing a bit more privacy while still being just a short drive to shopping, dining, and everyday conveniences in White River Junction and the surrounding area. Whether you're

  Randy Snelling KW Coastal and Lakes & Mountains Realty/Hanover

  0 Meadow Ln, Hartford, VT 05001
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  /14

  $239,000

  • Land
  • 10.1 Acres
  • $23,663 per Acre

  0 Christian St Unit 5084994, Hartford, VT 05001

  Beautiful, in town location. A very rare opportunity to own an in town Christian Street parcel of land. If you've been having a hard time finding the right home in this very tight housing market Or if you've been dreaming about new construction in the Hartford / Upper Valley area than look no further. This land parcel is conveniently located only minutes from Downtown White River Junction, VT. .

  Alex DeFelice The Clerkin Agency, P.C.

  0 Christian St Unit 5084994, Hartford, VT 05001
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  /40

  $729,000

  $20K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,423 Sq Ft

  441 Rhoades Hill Rd, Bethel, VT 05032

  Set within the scenic landscape of Barnard, this beautifully updated 3-bedroom, 3-bath home offers the perfect blend of Vermont charm and modern comfort. Surrounded by peaceful countryside and sweeping views, the property invites you to slow down and enjoy every season. Inside, the home is filled with warmth and character, featuring hardwood floors, natural woodwork, exposed beams, and an

  Daniel Preston KW Vermont Woodstock

  441 Rhoades Hill Rd, Bethel, VT 05032
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  /60

  $730,000

  • 4 Beds
  • 3.5 Baths
  • 3,453 Sq Ft

  1432 Union Village Rd, Norwich, VT 05055

  Classic New England home with lots of space, historic charm, and beautiful light. A bright, practical mudroom entry welcomes you, leading to a flexible floor plan anchored by a homey kitchen with a large pantry and eat in space. The property enjoys a spacious family room, a big deck, and a level back yard - an ideal setting for effortless indoor-outdoor entertaining. Upstairs, retreat to a

  Heidi Ruth Coldwell Banker LIFESTYLES - Hanover

  1432 Union Village Rd, Norwich, VT 05055
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  /21

  $259,000

  • 2 Beds
  • 1 Bath
  • 880 Sq Ft

  574 Willard Rd Unit 3F, Quechee, VT 05059

  Welcome to Unit 3F at Quechee Hollow Condominiums, a beautifully reimagined two-bedroom residence in the heart of Quechee Lakes—Vermont’s premier four-season resort community in the Upper Valley. Thoughtfully renovated in 2021 in a striking modern European style, this light-filled end unit offers a rare blend of contemporary design, craftsmanship, and resort living. The extensive renovation

  Sandy Reavill

  574 Willard Rd Unit 3F, Quechee, VT 05059
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  /37

  $455,000

  • 1 Bed
  • 1 Bath
  • 824 Sq Ft

  15 Railroad Row Unit 2C1, White River Junction, VT 05001

  Make your new home or pied-à-terre one of the few industrial loft condo units in the entire upper valley, right in the heart of thriving White River Junction. Great views from your own personal rooftop deck! If you like art, great restaurants, theater, good healthy shopping options and walking to all of them, this could be your new place. In 2006, five condos were built at Railroad Row as part of

  Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  15 Railroad Row Unit 2C1, White River Junction, VT 05001
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  /2

  $27,900

  $1K PRICE DROP

  • Land
  • 1.9 Acres
  • $14,684 per Acre

  223 Falcon Loop Rd E, Rochester, VT 05767

  Build your Vermont retreat on this 1.90-acre wooded lot in thedesirable Great Hawk community in Rochester. Surrounded by natural beauty, this property offers a peaceful setting with access to hiking, skiing, and year-round outdoor recreation, plus nearby attractions like the Green Mountain National Forest and scenic Route 100. Rochester is loved for its quiet charm, local farms, and

  Derek Greene Derek Greene

  223 Falcon Loop Rd E, Rochester, VT 05767
• 

  

  /22

  $279,900

  • Land
  • 9.4 Acres
  • $29,777 per Acre

  320 W Rowe Hill Rd, West Windsor, VT 05037

  On VAST trail, great trail location close to GMHA & Ascutney Outdoors, ride your horse, bike or sled from your door. A rare opportunity to shape a home or getaway that fits your lifestyle on 9.4 acres on class 4 road. The sellers have used all quality materials in a wonderful 24'x34' unfinished pole building, road upgrades to the property are done, state WW permit allows for 3 BR septic system,

  Dana Waters Dark Horse Realty

  320 W Rowe Hill Rd, West Windsor, VT 05037
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  /27

  $85,000

  • Land
  • 3.99 Acres
  • $21,303 per Acre

  00 Simonsville Rd, Andover, VT 05143

  3.99 +/- acres in Andover close to skiing and year round recreation. This lot is approved for a 4 bedroom home and has been updated with a new survey. A revised site plan is in process. 1080' of river bank to enjoy along the Williams River. A driveway (now grassed over) opens to a field and mowing path that leads to two separate meadows and the building site. Take your pick of 4 nearby ski

  Geralyn Donohue Engel & Völkers Okemo

  00 Simonsville Rd, Andover, VT 05143
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  /24

  $289,000

  • 1 Bed
  • 1 Bath
  • 624 Sq Ft

  38 Okemo Trailside Extension Unit 8A, Ludlow, VT 05149

  Sun-drenched and thoughtfully designed, this one-bedroom condo is ideally located in the sought-after Trailside community, just moments from the Sachem Trail, the new in-ground swimming pool, tennis courts, and additional parking. Offering true four-season appeal, it provides effortless access to Okemo Mountain while also serving as a comfortable year-round retreat. The open-concept layout is

  Karen Wilson TPW Real Estate

  38 Okemo Trailside Extension Unit 8A, Ludlow, VT 05149
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  /34

  $299,000

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

  39 Safford St, Royalton, VT 05068

  A good investment opportunity! Conveniently located, in the heart of South Royalton Village, is a traditional 3 bedroom home with the bonus of a detached garage that has a studio apartment above it. Within level walking distance from this property are the Vermont Law and Graduate School, the White River Valley High School, the South Royalton Health Center and shopping and dining in South Royalton

  John Wetmore Wetmore Real Estate

  39 Safford St, Royalton, VT 05068
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  /12

  $178,000

  • Land
  • 28.74 Acres
  • $6,193 per Acre

  00 Dairy Hill Rd Unit 7 and 8, Royalton, VT 05068

  Offering 28.7 acres of surveyed land comprised of two adjoining parcels with frontage on both Dairy Hill Road and Sherlock Road in the town of Royalton. This versatile property features a mix of open pastureland along the Dairy Hill side and predominantly wooded acreage along Sherlock Road, providing a balance of usability and privacy and has a small stream running through it. With multiple

  Eric Kenyon Rural Vermont Real Estate

  00 Dairy Hill Rd Unit 7 and 8, Royalton, VT 05068
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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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  /12

  $300,000

  • Land
  • 36.9 Acres
  • $8,130 per Acre

  1441 Jerusalem Hill, Rochester, VT 05767

  Set on 37± acres on the edge of Rochester’s wild landscape, this property offers a rare combination of immediate usability and long-term upside. Tucked just off the road for privacy, the land unfolds as a mix of rolling terrain, mature woods, and open pockets that invite exploration, recreation, and thoughtful development. At the center of it all is a rustic camp—simple, functional, and ready to

  William Brokhof Vermont Backcountry Real Estate

  1441 Jerusalem Hill, Rochester, VT 05767
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  /24

  $217,500

  • Land
  • 94 Acres
  • $2,314 per Acre

  6416 Vermont 107, Stockbridge, VT 05772

  Nestled among natural streams in the rolling hills of Vermont’s Green Mountains, this remarkable 94-acre parcel offers sweeping views overlooking the White River. Rich with potential for residential use or future development, the property includes a private septic system and a drilled well already in place. With 670 feet of frontage along VT Route 107, the land provides convenient access while

  Kate Jarvis Williamson Group Sothebys Intl. Realty

  6416 Vermont 107, Stockbridge, VT 05772
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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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  /48

  $2,500,000

  • 6 Beds
  • 6 Baths
  • 7,019 Sq Ft

  5518 Vermont 12, Barnard, VT 05031

  This gracious 1796 Brick Federal homestead was transformed into a popular gathering spot more than 60 years ago. The Barnard Inn has long been considered among the finest dining and hospitality venues in Vermont. It is currently operated as an event destination by the chef-owner and his family. Now, with children grown and off on their own paths, it is time to pass stewardship of the historic

  Laird Bradley Williamson Group Sothebys Intl. Realty

  5518 Vermont 12, Barnard, VT 05031
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  /19

  $499,500

  $26K PRICE DROP

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

  175 Pleasant Valley Rd, Springfield, VT 05156

  MOTIVATED SELLERS!!! This could be your escape 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.

  Carol Cole BHG Masiello Brattleboro

  175 Pleasant Valley Rd, Springfield, VT 05156
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  /55

  $1,359,000

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

  1355 Podunk Rd, White River Junction, VT 05001

  Perched in the hills of Norwich, Vermont, this curated "Scandinavian-esk" property offers exceptional contemporary living surrounded by nature's inspiring beauty. Architecturally redesigned by Smith and Vansant in 2010, this home offers an open floor plan with easy gathering spaces bathed in natural light and warmed by the Finnish Tulikivi soapstone stove. The French doors open to a patio, an

  Wynne Washburn Coldwell Banker LIFESTYLES - Hanover

  1355 Podunk Rd, White River Junction, 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
• 

  

  /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
• 

  

  /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

Showing Results 121 - 160, Page 4 of 12