Windsor County VT Homes for Sale with Acreage

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  /5

  $139,000

  • 2,144 Sq Ft

  73 Union St, Springfield, VT 05156

  Nice sized in-town home and yard with large 2 car garage and shed. Lots of room for your toys. The home is currently a 2-unit home but was originally a single-family home and could be changed back into a one family without a lot of effort. Home does need some work so cash buyers only please. This could be your chance to get into rental business. Lots of possibilities for this home.Home is

  

  Julie Buffum

  Buffum Realty

  (802) 423-2965

  73 Union St, Springfield, VT 05156
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  /3

  $170,000

  • Land
  • 10.04 Acres
  • $16,932 per Acre

  00 Will Dean Rd, Springfield, VT 05156

  Nice piece of land with some selected clearing done but more could be done with the potential of views. Land is both clear and wooded, level and sloping. Located on a quiet gravel road with a mix of single-family homes and small farms it is the perfect reflection of rural Vermont. Just minutes to I91and downtown Springfield makes this a great spot to set down roots.

  

  Julie Buffum

  Buffum Realty

  (802) 327-7566

  00 Will Dean Rd, Springfield, VT 05156
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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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  /6

  $172,000

  • Land
  • 4.3 Acres
  • $40,000 per Acre

  51 Loveland Rd, Norwich, VT 05055

  Fantastic opportunity to build your dream home on this 4.3 -acre lot in Norwich, Vermont, complete with full architectural plans for the exact home the sellers were planning to build, as shown in the photos and renderings. The property has already undergone significant preparation, including completed building designs and preliminary plans for the water and septic system along with other

  

  Spenser Molloy

  Nexthome Modern Realty

  (802) 214-8650

  51 Loveland Rd, Norwich, VT 05055
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  /48

  $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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  /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
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  /48

  $500,000

  • 3 Beds
  • 3 Baths
  • 1,826 Sq Ft

  789 Hammond Hill Rd, West Windsor, VT 05089

  "The Hideaway House - A Private Sanctuary”: This light-filled contemporary retreat located high on a hill in fashionable West Windsor is the quintessential "Goldilocks" Vermont property. It offers a private woodland sanctuary where quiet tranquility and architectural highlights meet. Tucked into a secluded 5.52-acre wooded bowl and set back over 200 ft. from the road, this tasteful 3BR/3BA home

  

  Ross Doody

  Century 21 Highview Realty

  (802) 523-2984

  789 Hammond Hill Rd, West Windsor, VT 05089
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  /4

  $160,000

  • Land
  • 6 Acres
  • $26,667 per Acre

  1901 Royalton Hill Rd, South Royalton, VT 05068

  Great opportunity to turn this private lot into your dream Vermont retreat. Just 10 minutes from the highway. Current owner has started some clearing and land prep.

  

  Steve Swanson

  EXP Realty

  (802) 215-3062

  1901 Royalton Hill Rd, South Royalton, VT 05068
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  /50

  $1,395,000

  • 4 Beds
  • 2.5 Baths
  • 2,710 Sq Ft

  187 Hopson Rd, Norwich, VT 05055

  This one-of-a-kind spacious home was designed by the architect, George T. Hathorn, and built by G.R. Porter and Sons - both of whom represent an era of home building quality unsurpassed to this day. As befits the climate, the centerpiece of this house is a woodstove, framed by a grand 3-story brick chimney and adjacent staircase – a unique layout that is both beautiful and wonderfully efficient

  Zoe Hathorn Washburn Snyder Donegan Real Estate Group

  187 Hopson Rd, Norwich, VT 05055
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  /46

  $8,000,000

  • 3 Beds
  • 3.5 Baths
  • 6,096 Sq Ft

  115 Eastman Rd, South Woodstock, VT 05071

  Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

  Keri Cole Williamson Group Sotheby's International Realty

  115 Eastman Rd, South Woodstock, VT 05071
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  /60

  $3,275,000

  • 4 Beds
  • 4.5 Baths
  • 4,708 Sq Ft

  207 Willey Hill Rd, Norwich, VT 05055

  207 WILLEY HILL ROAD- Gorgeous, recently updated, sophisticated home a stone's throw away from Norwich, Hanover, Dartmouth College, and the best of the Upper Valley. Expertly renovated by renowned builders O’Hara & Gercke, the result is a seamless blend of luxury, charm, and comfort. The sunlit gourmet kitchen is both functional and elegant and commands breathtaking views of the pond, with an

  David Donegan Snyder Donegan Real Estate Group

  207 Willey Hill Rd, Norwich, VT 05055
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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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  /16

  $3,150,000

  • Land
  • 506 Acres
  • $6,225 per Acre

  Markham Mountain, Andover, VT 05143

  Red Top is a breathtaking 506 +/- acre parcel in the town of Andover and on the border of Weston. Here, the rugged grandeur of the Green Mountains unfolds, offering extraordinary views to the South, where the mountain silhouettes stretch across the skyline and the imposing profile of Glebe Mountain asserts its presence.This land's historical roots run deep, originally belonging to the Marsh

  Story Jenks LANDVEST

  Markham Mountain, Andover, VT 05143
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  /8

  $590,000

  • Land
  • 61.49 Acres
  • $9,595 per Acre

  0 Wild Apple Rd, Pomfret, VT 05067

  One of the most sought-after locations in the Woodstock area, this 61-acre property is accessed off of Wild Apple Road with a building site oriented to the south and east. At 1,600 feet in elevation, it enjoys sweeping views of Killington, Mount Ascutney, and the surrounding hills. The land offers complete privacy with a blend of woodlands, open fields, a stream, and a pond site. Bordering the

  Story Jenks LANDVEST

  0 Wild Apple Rd, Pomfret, VT 05067
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  /15

  $237,000

  • Land
  • 221 Acres
  • $1,072 per Acre

  0 New Boston Rd, Thetford, VT 05074

  IntroductionThe ownership is selling their property in two separate parcels, divided by the town line. The +/-60 acre Strafford parcel is well suited to future home development with paved town road frontage and roadside electric service. The +/-220 acre Thetford parcel is well suited to a camp or seasonal off-grid home development with beautiful local views.Both parcels have

  John Latham Fountains Land

  0 New Boston Rd, Thetford, VT 05074
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  /10

  $799,000

  • Land
  • 52.3 Acres
  • $15,277 per Acre

  00 Granite Ledge, Pomfret, VT 05059

  Pristine land with views of Ascutney! Build your dream home on this unspoiled parcel in one of Pomfret's most beautifully preserved and scenic locales. Surrounded by large landholdings and conserved farmland, but only ten minutes from Woodstock and with excellent access to Route 4and Quechee, the land comprises historic rock walls, mature hardwoods, a stream, and offers the potential for pastoral

  Keri Cole Williamson Group Sotheby's International Realty

  00 Granite Ledge, Pomfret, VT 05059
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  /22

  $140,000

  • Land
  • 12.9 Acres
  • $10,853 per Acre

  0 Woods Rd W Unit 5081865, Ludlow, VT 05149

  Can't find the right house, nor the right location? This coveted Farm Ridge Lot could solve all your problems. This 12.9 acre lot has various terrain and private wooded views. This lot is on a quiet cul-de-sac named Woods Road West. You can decide how much land to clear - it's begging to have the land opened up to reveal the stunning views that neighboring houses enjoy. The lot was previously

  Joseph Karl William Raveis Real Estate Vermont Properties

  0 Woods Rd W Unit 5081865, Ludlow, VT 05149
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  /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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  /54

  $1,000,000 Open Sat 10AM - 1PM

  • 12 Beds
  • 7 Baths
  • 3,883 Sq Ft

  299 Farrell Farm Rd, Norwich, VT 05055

  This fabulous 10-acre property, originally the site of Farrell Farm, offers a functional multi-unit setup with a strong rental history. The main residence is an 1850s antique Cape featuring six bedrooms, classic wood floors, and plenty of natural light. Attached to the house is a large barn that provides two-car garage space and a separate two-bedroom apartment, currently not rented and in need

  Rowan Carroll Coldwell Banker LIFESTYLES - Hanover

  299 Farrell Farm Rd, Norwich, VT 05055
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  /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. In a quiet Sharon cul-de-sac, this property has two 2-bedroom units, one on each floor. Newer roof, newer shared septic, poured concrete foundation. The lot includes 10.5 acres of land, majority of which abuts land owned by the Vermont Department of Fish & Wildlife, which connects to the White River.

  Devin Josler Black House Real Estate

  37 Dee Haven, Sharon, VT 05065
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  /55

  $1,285,000 Open Sat 11AM - 2PM

  • 4 Beds
  • 4 Baths
  • 3,782 Sq Ft

  57 Sundback Ln, Norwich, VT 05055

  This is a good one! Just ten minutes from Dan & Whit's General Store, 57 Sundback Lane sits on over three acres in a small subdivision off New Boston Road - the sweet spot where you get the warmth of neighbors and plenty of space to play and enjoy. The curb appeal makes a strong first impression. A well-designed circular drive welcomes you, and the property unfolds from there: gently rolling in

  Leah McLaughry Four Seasons Sotheby's Int'l Realty

  57 Sundback Ln, Norwich, VT 05055
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  /41

  $650,000

  • 3 Beds
  • 3.5 Baths
  • 2,129 Sq Ft

  149 Hawk Pond Rd, Plymouth, VT 05056

  This contemporary Hawk Resort home offers breathtaking open nature views from nearly every room. The main level welcomes you with a bright, open-concept living, dining, and kitchen area filled with natural light from expansive windows. The living room centers around a wood fireplace with brand-new insert, creating a warm and inviting focal point, and a convenient half bath completes this level.

  Mandolyn McIntyre Crow Real Broker LLC

  149 Hawk Pond Rd, Plymouth, VT 05056
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  /36

  $595,000

  • 3 Beds
  • 2 Baths
  • 2,568 Sq Ft

  75 Lyon Rd, South Royalton, VT 05068

  1798 Zebulon Lyon Farm awaits new owners with great taste in renovated, restored, and traditional features. This wonderful home features FIVE functional fireplaces completely rebuilt, expansive newer kitchen with open dining area, spacious bedrooms, and too many upgrades to list. The 24x24 garage/workshop, carport, wood boiler and wood storage gives easy access from the house mudroom w/ laundry.

  Dean Goulet Dunrovin Real Estate

  75 Lyon Rd, South Royalton, VT 05068
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  /33

  $1,200,000

  • 3 Beds
  • 2.5 Baths
  • 2,771 Sq Ft

  348 Fort Defiance Hill, Bethel, VT 05032

  You immediately become aware of the very special nature of this property the moment you turn onto the tree-lined driveway winding to the top of a mild grade where the home is perfectly sited. The barn garage section was built in 2010 and the main residence was added in 2019. The many features of this house make it a perfect primary residence or a welcoming vacation retreat. Open format

  Stan Butler Four Seasons Sotheby's Int'l Realty

  348 Fort Defiance Hill, Bethel, VT 05032
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  /11

  $149,900

  • Land
  • 12.7 Acres
  • $11,803 per Acre

  360 Dorman Rd, Andover, VT 05143

  Discover the perfect blend of privacy, natural beauty, and convenience on this stunning 12.7-acre parcel nestled in the heart of the Green Mountains in Andover. This mostly wooded property offers a peaceful, secluded setting with a cleared homesite ideally positioned for southern exposure and the potential for breathtaking long-range mountain views with additional clearing.A 5-bedroom

  Gary Coger Four Seasons Sotheby's Int'l Realty

  360 Dorman Rd, Andover, VT 05143
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  /54

  $1,395,000

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

  39 Wallis View Ln, Ludlow, VT 05149

  Set in the highly desirable South Hill Estates, this exceptional property pairs privacy with an unbeatable location just minutes from Okemo Mountain. Surrounded by nearly five acres, the home enjoys sweeping mountain views and a beautifully open landscape that invites year-round enjoyment. The yard is a true highlight—offering plenty of space to relax, entertain, and play. A picturesque pond

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  39 Wallis View Ln, Ludlow, VT 05149
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  /9

  $129,000

  • Land
  • 7.95 Acres
  • $16,226 per Acre

  0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143

  Nestled in the picturesque hills of Chester, this inviting 7.95+/- acre property offers the perfect blend of privacy, beauty, and potential. Wander through a peaceful forest where moss covered stones, classic Vermont stone walls, and soft woodland light create a truly serene setting. With some thoughtful clearing, this parcel could open up to stunning views overlooking the charming fields and

  Thaddeus Abare Barrett and Valley Associates Inc.

  0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143
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  /16

  $350,000

  • Land
  • 7.12 Acres
  • $49,157 per Acre

  Lots 2 & 3 Log Cabin Dr, Pomfret, VT 05067

  Discover an exceptional opportunity to own 7.12 acres in the heart of Pomfret, created by the seamless combination of two adjoining lots with an impressive 590’ of shared boundary. Offering both privacy and flexibility, this property is ideally suited for a luxury estate or multi-generation family compound on the VAST Trail. The land is enriched by the gentle flow of Barnard Brook, with a

  Sandy Reavill

  Lots 2 & 3 Log Cabin Dr, Pomfret, VT 05067
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  /44

  $425,000

  • 4 Beds
  • 2.5 Baths
  • 2,548 Sq Ft

  77 Wcfr Dr, Springfield, VT 05156

  Welcome to a property where Vermont’s natural beauty meets a lifestyle of quiet productivity and potential. Situated on 18.45+/- private acres in Springfield, this 1988-built home spans 2,548 square feet of living space designed to celebrate its surroundings. The heart of the residence is defined by its exceptional southern exposure; several sliding glass doors line the south-facing side of the

  Jill Lawrence The Real Estate Collaborative

  77 Wcfr Dr, Springfield, VT 05156
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  /44

  $675,000

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  518 Baltimore Rd, Chester, VT 05143

  Nestled on 10 picturesque rolling acres, just minutes from Chester Village Green and Okemo Mountain Resort, this beautiful country home offers the perfect blend of charm, comfort, and convenience. The property features established gardens, apple trees, blueberry bushes, and a stone patio—ideal for relaxing or entertaining.Inside, you’ll find two levels of well-designed living space. The

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

  518 Baltimore Rd, Chester, VT 05143
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  /11

  $249,000

  • Land
  • 57.2 Acres
  • $4,353 per Acre

  0 Masterson Unit 5080891, Barnard, VT 05031

  Discover 57.2 acres of exceptional forestland offering the perfect blend of privacy and convenience—tucked away yet less than half a mile from Vermont Route 12. This property provides an ideal setting for a private home or recreational retreat, with easy access to Barnard Village and Interstate 89. The recently cleared build site sits in a wonderful location above, yet not too far from Masterson

  Sophie Roya Berry Hill Real Estate

  0 Masterson Unit 5080891, Barnard, VT 05031
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  /38

  $875,000

  • 3 Beds
  • 3.5 Baths
  • 2,540 Sq Ft

  710 Meadowland Farms Rd, Hartford, VT 05001

  Sun-drenched post & beam Cape nicely situated on 5.44 acres with an open meadow and established gardens. This charming Cape offers the warmth of terracotta and wide-board wood floors under exposed beams. Whether you’re hosting in the formal dining room or relaxing by the fire, the south-facing windows ensure a bright, airy atmosphere. The first floor has a great layout with an eat-in kitchen with

  Rowan Carroll Coldwell Banker LIFESTYLES - Hanover

  710 Meadowland Farms Rd, Hartford, VT 05001
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  /28

  $675,000

  • 3 Beds
  • 2 Baths
  • 1,809 Sq Ft

  210 Holden Hill Rd, Weston, VT 05161

  Charming Vermont Ranch on 3.6 Acres with Stunning Mountain Views.Welcome to your peaceful retreat on desirable Holden Hill Road in Weston, Vermont. This beautifully maintained 3-bedroom, 2-bathroom ranch-style furnished home offers 1,809 square feet of thoughtfully designed living space, perfectly situated on 3.6 scenic acres with breathtaking mountain views.Built in 2019 with exceptional

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  210 Holden Hill Rd, Weston, VT 05161
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  /38

  $424,000

  • 4 Beds
  • 2.5 Baths
  • 2,888 Sq Ft

  273 Route 5 N, Windsor, VT 05089

  A rare piece of Vermont history, thoughtfully preserved for modern living. Dating to 1790, this distinguished brick and frame Colonial stands as a testament to early New England craftsmanship — and it's ready for its next chapter. Meticulously maintained over the centuries and updated where it counts, this two-story home offers the warmth of wide-plank hardwood and softwood floors, the peace of

  Allison Griep BHHS Verani Upper Valley

  273 Route 5 N, Windsor, VT 05089
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  /13

  $229,000

  • Land
  • 4.1 Acres
  • $55,854 per Acre

  398 Valley View Rd, White River Junction, VT 05001

  Opportunity meets convenience on this versatile 4.10-acre property with both residential and commercial zoning, offering endless potential for your future plans. The lot includes an existing foundation along with utilities already in place, including power, spring well, and septic, giving buyers a valuable head start. Set adjacent to the highway for quick and easy access, the property enjoys

  Grayson VanHendrick Flex Realty

  398 Valley View Rd, White River Junction, VT 05001
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  /41

  $4,250,000

  • 7 Beds
  • 9 Baths
  • 9,615 Sq Ft

  5893 Stage Rd, Barnard, VT 05031

  Set on 54 exceptionally private acres, Long Way Hill is a a quietly luxurious Vermont country retreat overlooking a half-acre pond, with sweeping lawns, gardens, fields, and woodland trails. It is located minutes from Silver Lake and Twin Farms, and 15 minutes from Woodstock. Designed by David Beilman and built by Savelberg Construction in 2006, the home is defined by its high

  Story Jenks LandVest, Inc/Woodstock

  5893 Stage Rd, Barnard, VT 05031
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  /13

  $115,000

  • Land
  • 5 Acres
  • $23,000 per Acre

  3200 Baltimore Rd, Chester, VT 05143

  This lovely open lot offers many possibilities for future use. Facing South, the land is 80% open and bordered by beautiful stonewalls and mature Maple trees. The long range Mountain views are visible from many different locations on the land. A wonderful opportunity to own a piece of Vermont, nestled in the Green Mountains.

  Kate Jarvis Williamson Group Sothebys Intl. Realty

  3200 Baltimore Rd, Chester, VT 05143
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  /32

  $239,000

  • 1 Bed
  • 1 Bath
  • 856 Sq Ft

  42 Heritage Condo Way Unit 23 D, Woodstock, VT 05091

  Amazing opportunity to own a property that is perfect as a full time home or a vacation get away, in the highly desired Heritage Condo community. The setting is serene in a low density area. This condo has had many updates and is ready for new owners to add their personal touch. The charming living room complete with wood floors , a stone accent wall and double glass doors leading to a private

  Carol Wood Williamson Group Sothebys Intl. Realty

  42 Heritage Condo Way Unit 23 D, Woodstock, VT 05091
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  /17

  $49,000

  • Land
  • 1.46 Acres
  • $33,562 per Acre

  0 Kestrell Dr Unit 5079994, Plymouth, VT 05056

  Discover the perfect canvas for your Vermont dream home with this exceptional 1.46 +/- acre lot in Hawk Resort. Ideally situated between Okemo Mountain and Killington Resort, this location offers unmatched access to some of the region’s best year-round recreation. As a Hawk owner, enjoy access to the desirable lakes region, where outdoor adventure awaits in every season. Spend your days exploring

  Joseph Karl William Raveis Real Estate Vermont Properties

  0 Kestrell Dr Unit 5079994, Plymouth, VT 05056

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