Windsor County VT Homes for Sale

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  /49

  $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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  /47

  $149,000

  • 1 Bed
  • 1 Bath
  • 624 Sq Ft

  49 Clay Hill Rd, Hartland, VT 05048

  Partially finished circa 1998 26' x 24' ranch house on 2 lots totalling 1.76+/- acres. This fixer-upper has been lived in year round since its construction but never fully finished. The space consists of a kitchen that opens into a single main room being used as a living room, bedroom and dining area. Both the interior and exterior wall surfaces need finishing in places. The interior needs

  Steve Schoppmeyer BHG Masiello Brattleboro

  49 Clay Hill Rd, Hartland, VT 05048
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  /16

  $96,232 New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  517 Back Mountain Rd, Windsor, VT 05089

  Welcome to 517 Back Mountain Rd., Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  517 Back Mountain Rd, Windsor, VT 05089
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  /16

  $3,150,000

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

  00 Marsh Cross Rd, 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, Inc/Woodstock

  00 Marsh Cross Rd, Andover, VT 05143
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  /14

  $69,000

  • Land
  • 1.05 Acres
  • $65,714 per Acre

  Lot 49 Spring St, Stockbridge, VT 05772

  Attractive building lot in the desirable Highwood community. This lot offers potential long-range views and includes sewer rights in the Highwood community sewer system, sufficient for a three-bedroom residence. Architectural review and protective covenants ensure that the quality of life in this small community is always preserved. Highwood is adjacent to the Green Mountain Trail network for

  Kyle Kershner Killington Pico Realty

  Lot 49 Spring St, Stockbridge, VT 05772
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  /35

  $424,900

  • 1 Bed
  • 1.5 Baths
  • 1,255 Sq Ft

  71 Grouse Ln, Perkinsville, VT 05151

  This beautiful, expanded Cape is set in a quiet, peaceful location and is very well appointed throughout, offering a warm and welcoming place to call home. A charming covered front porch invites you to sit back and relax, while a thoughtfully designed entryway creates an easy and inviting transition into the living space. The interior has been extremely well maintained, blending modern comfort

  Thaddeus Abare Barrett and Valley Associates Inc.

  71 Grouse Ln, Perkinsville, VT 05151
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  /32

  $299,900

  • 3 Beds
  • 2.5 Baths
  • 1,614 Sq Ft

  127 Mountains Edge Rd Unit 211, Brownsville, VT 05037

  Immaculate end-unit condominium offering the ease of single-floor living at its finest. Thoughtfully maintained and move-in ready, this home impresses from the moment you walk in- tasteful finishes throughout create a polished, welcoming atmosphere. Newer windows flood the space with natural light, and a new heating system ensures year-round comfort. The primary suite features a beautifully

  Katie Ladue Gilbert BHHS Verani Upper Valley

  127 Mountains Edge Rd Unit 211, Brownsville, VT 05037
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  /49

  $449,000

  • 2 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  339 Ranney Rd, Stockbridge, VT 05772

  EXTRA ACRE! EXTRA VALUE. PROPERTY NOW INCLUDES one more acre than previously listed. Take a look at this home in central Vermont- close to the premier Killington Mountain Ski Resort. This property is on an open 3 acre lot with plenty of sun and space for renovations, pets, gardens, greenhouses or farm animals. This Stockbridge home has an in-law apartment below- accessible by a separate driveway.

  Risa Mornis Covered Bridge RE

  339 Ranney Rd, Stockbridge, VT 05772
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  /58

  $3,490,000

  • 4 Beds
  • 4.5 Baths
  • 2,894 Sq Ft

  1726 Skitchewaug Trail, Springfield, VT 05156

  A circa 1734 Cape, displaying museum quality authentic detailing, in a setting worthy of a Vermont Life Magazine cover! Originally sited in New Hampshire, the Cape was patiently dismantled, with components meticulously cataloged, and then relocated to an idyllic Vermont hilltop setting! The post and beam construction, gunstock corner posts, exposed beams, extraordinarily wide floor boards, 4

  John Wetmore Wetmore Real Estate

  1726 Skitchewaug Trail, Springfield, VT 05156
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  /14

  $289,000

  • 2 Beds
  • 2.5 Baths
  • 1,475 Sq Ft

  106 Contro Rd, Chester, VT 05143

  Sweet! An just in time for the holidays. This cabin has been lived in year round and has a drilled well, septic and electric. The basement has been partially finished with the fixtures of a 3/4 bath but no wall coverings, so the square footage is not counted here. The tenant does not have internet so it is best to check on phone/tv and internet from the providers. The property is being divided

  Christine Lewis Brattleboro Area Realty

  106 Contro Rd, Chester, VT 05143
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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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  /60

  $420,000

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

  2451 Camp Brook Rd, Bethel, VT 05032

  This charming log home sits nestled off the main road, above the nearby Camp Brook, which meanders through the property. This home was thoughtfully built and lovingly cared for by it's current owner. The open living/dining room is light filled by skylights and sliding glass doors that lead to the back deck. Cozy up by the brick fireplace with stove insert. Sit and listen to the babbling brook on

  Suzi Lamson Vermont Heritage Real Estate

  2451 Camp Brook Rd, Bethel, VT 05032
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  /7

  $1,250,000

  • Land
  • 14,810 Sq Ft
  • $3,676,471 per Acre

  130 Main St, Ludlow, VT 05149

  For generations, the Pot Belly building was a familiar and beloved part of Ludlow Village—a place where locals and visitors gathered, stories were shared, and the energy of the village came to life. Today, the building may be gone, but the opportunity it created is just beginning.Now offered as a prime, cleared village lot, this property represents a rare chance to be part of Ludlow’s next

  Joseph Karl William Raveis Real Estate Vermont Properties

  130 Main St, Ludlow, VT 05149
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  /60

  $200,000

  • 3 Beds
  • 3 Baths
  • 2,011 Sq Ft

  625/627 Q3 Jackson Gore Adams House Unit 625/627 Q3, Ludlow, VT 05149

  Jackson Gore area of Okemo– Adams House Quarter Share Ownership, Unit 625/627 Quarter III (includes Christmas weeks for 2026). Enjoy slopeside living with mountain views in this three-bedroom, three-bathroom condominium with just over 2000 square feet of living space. Located within The Adams House at Jackson Gore on Okemo, offering direct slope access. Enjoy luxury living with full access to The

  Kevin Barnes William Raveis Real Estate Vermont Properties

  625/627 Q3 Jackson Gore Adams House Unit 625/627 Q3, Ludlow, VT 05149
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  /45

  $499,000

  • 3 Beds
  • 1.5 Baths
  • 2,656 Sq Ft

  2140 Brandon Mountain Rd, Rochester, VT 05767

  Tucked away on a picturesque 3-acre lot, this classic three-bedroom expanded Cape offers privacy, seclusion, and peaceful views in a beautiful Rochester valley setting. Set nearly 700 feet back from the road and bordering the Green Mountain National Forest, the property enjoys a tranquil natural backdrop where a scenic pond at the edge of the land attracts birds and wildlife. The main level

  Kyle Kershner Killington Pico Realty

  2140 Brandon Mountain Rd, Rochester, VT 05767
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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

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,489 Sq Ft

  6852 Us Route 4, Bridgewater, VT 05034

  This 1885 antique story and a half cape has been comprehensively updated during the long ownership of the sellers who made the home more energy efficient with all new windows, recent heating system, modern kitchen and bathrooms. The home creatively blends an historic floor plan defined by a traditional living room and dining room with the more casual lifestyle of today. The open concept Vermont

  Laird Bradley Williamson Group Sothebys Intl. Realty

  6852 Us Route 4, Bridgewater, VT 05034
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  /59

  $1,450,000

  • 3 Beds
  • 3 Baths
  • 1,836 Sq Ft

  144 Lodge Rd Unit 1, Ludlow, VT 05149

  Experience the ultimate in ski-on/ski-off living with this exceptional 3-bedroom, 3-bathroom slopeside condominium on Okemo Mountain, located in the sought-after SouthFace Village. Park with ease in your assigned covered space beneath the building, complete with a private storage closet for all your mountain gear. From there, take the elevator or walk up the stairs to this first-floor residence,

  Joseph Karl William Raveis Real Estate Vermont Properties

  144 Lodge Rd Unit 1, Ludlow, VT 05149
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  /8

  $125,000

  • Land
  • 7.5 Acres
  • $16,667 per Acre

  00 Howe Hill Rd, Sharon, VT 05065

  Vermont Retreat Awaits. A 7.5 acre wooded parcel with spectacular mountain view potential and five bedroom state waste water permit is ready for your vision. Located off town-maintained Howe Hill Road in Sharon, Vermont, via right of way from lower parcel. Convenient access to power and ultra-high speed fiber optic (EC Fiber) internet at the street, just one mile from I-89. Enjoy easy access to

  Joanne Kent Four Seasons Sotheby's Int'l Realty

  00 Howe Hill Rd, Sharon, VT 05065
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  /15

  $329,000

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

  40 Union St, White River Junction, VT 05001

  Good Cash Flow! Possibilty of Commercial business aspect exists with this property as its in the CB zone / Central Business district. This fully leased two unit property is an excellent chance for investors to add a consistent cash flowing building to their portfolio or for an onsite owner to occupy one unit and let the extra additional rent help pay for your housing. A fairly low maintenance

  Alex DeFelice The Clerkin Agency, P.C.

  40 Union St, White River Junction, VT 05001
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  /23

  $650,000

  • 2,674 Sq Ft

  5863 Vermont 14, Royalton, VT 05068

  Overlooking the magnificent White River and Second Branch, this attractive older home has been a labor of love for the past 30 years. The long list of upgrades, additions, improvements, etc. speak for themselves. The spacious first floor has been used as home occupation featuring a 350 sq. ft. impressive office space. Own your own island in the White River and enjoy the rich gardening soil in the

  Dean Goulet Dunrovin Real Estate

  5863 Vermont 14, Royalton, VT 05068
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  /41

  $399,000

  • 5 Beds
  • 3.5 Baths
  • 2,200 Sq Ft

  109 Park Row, Rochester, VT 05767

  The Richard Steele Hubbard home, ideally situated just off the park in the charming village of Rochester, Vermont, is a fine example of the American Foursquare style popular in the late 19th and early 20th centuries. This five-bedroom residence retains many period details, including handcrafted woodwork, hardwood floors, coffered ceilings, stamped tin, and decorative moldings. Thoughtful updates

  Kyle Kershner Killington Pico Realty

  109 Park Row, Rochester, VT 05767
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  /24

  $675,000

  • Land
  • 41.9 Acres
  • $16,110 per Acre

  8 Grout Rd, Hartland, VT 05048

  Rare, one-of-a-kind land offering with close proximity to Quechee and Hartland.Beautiful building site with Western exposure and exceptional views to the West and North. Pastureland and open meadows for any farming and cultivation needs. Easy construction for additional out buildings or subdivision is possible.Road frontage on Grout Road and the Quechee Hartland road.Private, with

  Charles Bacon Quechee Lakes Real Estate Center

  8 Grout Rd, Hartland, VT 05048
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  /48

  $589,000

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

  530 West Rd, Barnard, VT 05031

  Conveniently located less than a mile from Barnard General Store and Silver Lake, this charming 3 bedroom cape sits on just over 3 acres of land with tiered stone walls and green lawn circling the house. Mature trees surround the yard and there is view potential with minor clearing and thinning. The full length back deck offers private outdoor space including a covered grilling area just steps

  Dan Noble Snyder Donegan Real Estate Group

  530 West Rd, Barnard, VT 05031
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  /13

  $489,000

  • 8 Beds
  • 4 Baths
  • 3,483 Sq Ft

  13 Hawthorn St, Hartford, VT 05001

  Strong Cash Flow! Profitable Investment Opportunity! This four unit multifamily property is an excellent chance for investors to add a consistent cash flowing building to their portfolio or for an on site owner occupancy and the extra rents to pay for your housing.Located in charming Wilder village on a generous .25 +/- acre in town lot. The units consist of three bedroom, two bedrooms and a

  Alex DeFelice The Clerkin Agency, P.C.

  13 Hawthorn St, Hartford, VT 05001
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  /14

  $1,560,000 New Construction

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

  7034 Hiram Atkins Byway Rd Unit 7043, Hartford, VT 05059

  The Thistle at Mountain Stream — To be built by Mountain Stream at Quechee Lakes, the Thistle offers 3,120 square feet of contemporary living across two levels, paired with a single-bay tuck-under garage, separate heated storage with optional rec-room conversion, and a detached two-car garage. A long, low silhouette under a sweeping shed roof, vertical board-and-batten siding, and a dramatic

  Richard Higgerson Higgerson & Company

  7034 Hiram Atkins Byway Rd Unit 7043, Hartford, VT 05059
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  /11

  $1,620,000

  • Land
  • 153.73 Acres
  • $10,538 per Acre

  0 Vermont 106, Reading, VT 05062

  Tucked away near the sought-after communities of Woodstock, West Windsor, and Ludlow, this untouched parcel invites endless possibilities. From its elevated perch, it offers sweeping views of Mt. Ascutney and the Connecticut River Valley in every direction. The Northern New England forested landscape is crisscrossed with trails, old roads, and natural springs, perfect for exploration. There are

  Laird Bradley Williamson Group Sothebys Intl. Realty

  0 Vermont 106, Reading, VT 05062
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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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  /28

  $4,500,000

  • Land
  • 127 Acres
  • $35,433 per Acre

  85 Pallottas Hill Rd, Ludlow, VT 05149

  MAJOR 7 FIGURE PRICE REDUCTION! Live, Build, Develop - 127 Acres at Okemo's Doorstep. ~Prime Development Opportunity at the Base of Okemo Mountain. A rare and highly developable 127-acre parcel located just 2 minutes from downtown Ludlow at the foot of world-renowned Okemo Mountain. ~Preliminary engineering, structural work and surveys are complete making this a premier opportunity for a luxury

  Frank Provance Diamond Realty

  85 Pallottas Hill Rd, Ludlow, VT 05149
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  /2

  $221,000

  • Land
  • 8.52 Acres
  • $25,939 per Acre

  0 Barrister Dr Unit 3, Hartford, VT 05001

  In-town building lot opportunity! Don't miss this chance to build your single family home or possibly a multifamily project in the Barrister Drive area of Wider, VT. A nice 8.52 +/- acre in-town lot located at the end of Palmer Court or Barrister Drive. This property is adjacent to an additional 25 +/- acre Norwich, VT. lot that is also for sale at $159,000. and could possibly be used for an

  Alex DeFelice The Clerkin Agency, P.C.

  0 Barrister Dr Unit 3, Hartford, VT 05001
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  /37

  $1,995,000

  • 4 Beds
  • 2.5 Baths
  • 3,839 Sq Ft

  198 Piper Hill Rd, Weston, VT 05161

  Uplands is a gracious 105-acre hill farm on the south-facing slope of Markham Mountain, located just outside the historic village of Weston. Anchored by an 1800s farmhouse, the main residence has been thoughtfully added on to and renovated over the years and offers over 3,839 square feet of living space, including four bedrooms, three fireplaces and an attached two bay garage. The guest house

  Story Jenks LandVest, Inc/Woodstock

  198 Piper Hill Rd, Weston, VT 05161
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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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  /51

  $390,000

  • 3 Beds
  • 2 Baths
  • 1,304 Sq Ft

  663 Depot St, Chester, VT 05143

  Fully renovated from top to bottom, this Chester property offers the kind of peace of mind that’s hard to find in an older Vermont home. Major systems including electrical, plumbing, heating, insulation, drywall, and windows, have all been updated, allowing the next owner to step in without a long to-do list. Inside, the home strikes a thoughtful balance between character and clean updates.

  Betsy Adamovich Real Broker LLC

  663 Depot St, Chester, VT 05143
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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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  /60

  $4,775,000

  • 7 Beds
  • 6.5 Baths
  • 6,624 Sq Ft

  924 Okemo Ridge Rd Unit S 11, Ludlow, VT 05149

  Perched in Solitude, one of Okemo’s most sought-after on-mountain neighborhoods, 924 Okemo Ridge Road offers exceptional slope access, sweeping long-range views, and the scale to comfortably bring generations together under one roof. With 7 bedrooms and 6.5 bathrooms, this is a true ski home—designed for gathering, hosting, and making memories year after year. The home delivers classic ski lodge

  Katherine Burns William Raveis Real Estate Vermont Properties

  924 Okemo Ridge Rd Unit S 11, Ludlow, VT 05149
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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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  /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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  /46

  $195,000

  • 3 Beds
  • 3 Baths
  • 1,670 Sq Ft

  335/337 Qtr I V Jackson Gore Inn, Ludlow, VT 05149

  Jackson Gore Inn Unit 335/337 Quarter I V : Beautifully appointed 3-bedroom, 3-bathroom unit located in the highly desirable Jackson Gore area, offering stunning slope views and a private deck to enjoy all seasons. Perfectly situated in the charming stone archway, this residence provides both convenience and a classic mountain feel. The spacious layout comfortably sleeps 12, making it ideal for

  Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

  335/337 Qtr I V Jackson Gore Inn, Ludlow, VT 05149
• 

  

  /41

  $999,500

  • 3,218 Sq Ft

  1 Depot St, Hartford, VT 05001

  Excellent Upper Valley investment opportunity! This well-maintained six-unit multifamily property features a desirable mix of 3 one-bedroom apartments and 3 two-bedroom apartments, ideally situated in the heart of Wilder. The property sits directly across from the bus stop and offers convenient access to major employers and amenities — just 9 minutes (4.2 miles) from Dartmouth College and 17

  Loren Wehmeyer Tesla Realty Group, LLC

  1 Depot St, Hartford, VT 05001
• 

  

  /50

  $199,000

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft

  95 Union St, Springfield, VT 05156

  CASH ONLY. This well-priced home is full of potential and ready for your cosmetic upgrades and a bit of sweat equity. Offering three bedrooms and two baths on a generous lot, it’s conveniently located near the hospital, shopping, and essential amenities. The spacious master bedroom features an ensuite bath, while the additional partially finished attic provides room for expansion or storage.

  Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  95 Union St, Springfield, VT 05156

Showing Results 81 - 120, Page 3 of 11