Windham County VT Homes for Sale

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  $35,000

  • Land
  • 5 Acres
  • $7,000 per Acre

  0 Ober Hill Rd, Townshend, VT 05353

  Escape to your own private piece of Vermont with this beautiful 5-acre sloping wooded property. Located off the beaten path, yet conveniently close to route 30, you’ll find a peaceful forest of mature Oak, Ash and Pine trees. Whether you're a camping enthusiast or seeking a serene hideaway, this land offers a spectacular setting. Property is accessed at the end of an old town road that is no

  Rebecca Hiam Southern Vermont Realty Group

  0 Ober Hill Rd, Townshend, VT 05353
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  /9

  $118,000

  • Land
  • 10.04 Acres
  • $11,753 per Acre

  Lot 2 North St, Dover, VT 05431

  Discover the perfect Vermont retreat on this 10.48 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape. Whether you envision a

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 2 North St, Dover, VT 05431
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  /60

  $875,000

  • 5 Beds
  • 4.5 Baths
  • 3,840 Sq Ft

  42 Blackberry Ln, Jamaica, VT 05343

  Welcome to "Sweet Berry Farm", a charming Vermont homestead blending 1850s character with a spacious modern addition. Set on 5.7 private acres in Jamaica, this property offers abundant natural beauty—mature apple trees, blueberry and blackberry bushes and vibrant seasonal gardens. The expanded farmhouse provides exceptional space for living and entertaining. The main floor features an open living

  MaryKate Grey Stratton Real Estate

  42 Blackberry Ln, Jamaica, VT 05343
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  /45

  $798,000

  • 3 Beds
  • 2 Baths
  • 2,588 Sq Ft

  619 Stratton Arlington Rd, West Wardsboro, VT 05360

  Nestled between Stratton and Mount Snow and just minutes from Grout Pond, this timeless Vermont log home offers the perfect balance of rustic charm and modern comfort. Set on 7.90 beautifully landscaped acres with perennial gardens, a small pond, and mature fruit trees, the property captures the essence of mountain living.The main level features an open-concept layout with soaring beamed

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  619 Stratton Arlington Rd, West Wardsboro, VT 05360
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  /17

  $73,140

  • Land
  • 0.25 Acre
  • $292,560 per Acre

  Lot 4 -156 High Peak Way, Wilmington, VT 05363

  Lot 4 in the High Peak Development, a .25-acre wooded parcel offering an ideal opportunity to create your own Vermont getaway. Perfectly situated just a short drive from Mount Snow, The Hermitage Club, and the recreational offerings of the Deerfield Valley, this lot provides the charm of a cabin in the woods setting with exceptional convenience.With public sewer and public water access,

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 4 -156 High Peak Way, Wilmington, VT 05363
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  /23

  $3,500,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 7,000 Sq Ft

  29 Mountain Ridge Dr, Wilmington, VT 05363

  The Mountain Ridge community is newly developed and this is the first opportunity to enter this new prestigious location. 38 acres with 5 total lots, including a spectacular newly built luxury Timber Frame home being sold as-is near completion, with a builder on board ready to finish, plus 4 separate gorgeous mountain view building sites. Finish this home with the fixtures and finishes already

  Adam Palmiter Berkley & Veller Greenwood/Dover

  29 Mountain Ridge Dr, Wilmington, VT 05363
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  $382,000

  • 6 Beds
  • 2.5 Baths
  • 3,590 Sq Ft

  88 Westminster St, Town of Rockingham, VT 05101

  Welcome to this stately New Englander located in the heart of Bellows Falls, offering the perfect blend of historic character and generous living space. With over 4,500 square feet, this grand home provides 15 rooms, 6 bedrooms and the potential for 4 bathrooms across multiple levels, giving plenty of room for family, guests, home office space, or multi-generational living. Beautiful period

  Jamie Watson BHG Masiello Keene

  88 Westminster St, Town of Rockingham, VT 05101
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  /33

  $120,000

  • Land
  • 5 Acres
  • $24,000 per Acre

  0 Happy Haven Rd Unit 4998180, Wilmington, VT 05363

  Beautiful 5-Acre Lot with Mountain Views – Approved for Two Homes!Here’s your chance to own a truly special piece of Vermont! This gorgeous 5-acre parcel on Route 100, just north of Wilmington center, offers the perfect setting for your dream home—or two. Recent soil tests support two single-family homes, each with up to three bedrooms. The land features an open, sun-drenched meadow, gently

  Monique White Deerfield Valley Real Estate

  0 Happy Haven Rd Unit 4998180, Wilmington, VT 05363
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  /34

  $389,900

  • 2 Beds
  • 2 Baths
  • 1,076 Sq Ft

  295 Stratton Arlington Rd, West Wardsboro, VT 05360

  Beautifully renovated 2-bedroom, 2-bath cottage on 1.9 acres in Stratton. Ideally located just minutes from both Mount Snow and Stratton ski areas, with the Stratton Recreation Center conveniently down the road. Enter through the mudroom into a bright, open-concept kitchen and dining space featuring a cozy woodstove and 4 skylights. The living room is spacious with a mini split and also includes

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  295 Stratton Arlington Rd, West Wardsboro, VT 05360
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  /32

  $21,000

  • 1 Bed
  • 1 Bath
  • 671 Sq Ft

  302 Qtr.1, 89 Grand Summit Way, Dover, VT 05356

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Benefits of Grand Summit ownership include the best ski in/out mountain location available. Use of the Grand Summit amenities all year round including valet parking, owners private lounge, private owners library, full service spa with saunas hot tubs and outdoor heated pool, private owners only ski/golf locker rooms for year

  Kelly Agrillo Southern Vermont Realty Group

  302 Qtr.1, 89 Grand Summit Way, Dover, VT 05356
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  $299,900

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  10 King St, Bellows Falls, VT 05101

  Discover the ideal balance of privacy and convenience in this welcoming 4-bedroom, 2-bath home in the heart of Bellows Falls. Set on a spacious 1-acre lot, the 1,800-sq-ft interior provides generous room for comfortable everyday living. A private garage and secluded yard offer both practicality and serenity, while the large covered porch invites year-round enjoyment of the outdoors. With

  Floyd Amidon Maple Leaf Realty

  10 King St, Bellows Falls, VT 05101
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  /48

  $380,000

  • 3 Beds
  • 1.5 Baths
  • 2,433 Sq Ft

  183 Bear Hill Rd, Dummerston, VT 05301

  Discover a hidden gem nestled deep in the woods—a rustic retreat that’s entirely off-grid and 100% solar powered. Perfect for nature lovers, creative spirits, or anyone seeking serenity and self-sufficiency. This one-of-a-kind property features a charming main house with a two-bedroom loft attached, currently used for short-term rentals. The main cabin exudes classic Adirondack charm with

  Kate Barry EXP Realty

  183 Bear Hill Rd, Dummerston, VT 05301
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  /9

  $250,000

  • Land
  • 3.79 Acres
  • $65,963 per Acre

  000 Fort Dummer Heights, Brattleboro, VT 05301

  Easy to build!!! The land is open, so no fuss with a lot of prep. Beautiful high meadow, in a nice little neighborhood tucked up against the state park, what more could you want? This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor cooperation.

  Christine Lewis Brattleboro Area Realty

  000 Fort Dummer Heights, Brattleboro, VT 05301
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  /22

  $56,800

  • 3 Beds
  • 3 Baths
  • 1,323 Sq Ft

  157/265/267qtr3 Grand Summit Way Unit 157/265/267, Dover, VT 05356

  TRAILSIDE. Imagine the opportunity of owning a unit at the Grand Summit that can be used as studios that sleep 4, a 1 bedroom sleep 8 or even host 12 guests. Unit 157 sleeps 4 and has a sleep sofa and a Murphy bed, full kitchenette and a full bath. 157 connects via a flight of stairs to unit 267, another studio with a sleep sofa, Murphy bed, kitchenette and full bath, sleeps 4. Unit 265 has 2

  Sheila Joyce-Albano Skihome Realty

  157/265/267qtr3 Grand Summit Way Unit 157/265/267, Dover, VT 05356
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  /45

  $1,470,000

  • 5 Beds
  • 4.5 Baths
  • 5,160 Sq Ft

  224 Cobble Ridge Rd, Londonderry, VT 05148

  Perched on scenic Cobble Ridge, this custom five-bedroom, four-and-a-half-bath retreat embodies balance, light, and renewal in the heart of Southern Vermont. Set on seven private, fenced acres framed by stone walls and dual gated entries, the property enjoys southwest exposure with soft, filtered ridgeline views that evolve beautifully through the seasons. Inside, a brick fireplace anchors the

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  224 Cobble Ridge Rd, Londonderry, VT 05148
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  $599,000

  • 3 Beds
  • 2.5 Baths
  • 2,782 Sq Ft

  628 Townshend Rd, Grafton, VT 05146

  One of only two stone houses in the charming town of Grafton, this stately home is a truly special opportunity. Perched on a hill across from the renowned Grafton Cheese Company, the property offers easy access to village amenities and year-round recreation at Grafton Ponds Outdoor Center. Inside, you'll find a spacious and inviting layout: Large front living room with exposed beams, a beautiful

  Jessica Landers Barrett and Valley Associates Inc.

  628 Townshend Rd, Grafton, VT 05146
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  $895,000

  • 3 Beds
  • 4.5 Baths
  • 3,318 Sq Ft

  42 Sugar House Rd, West Dover, VT 05356

  Tucked into the serene hills of Dover, Vermont, this custom crafted mountain home offers the ideal blend of rustic charm and modern comfort just minutes from Mount Snow and The Hermitage Club. Set on a private lot with winter views of both ski mountains, this 3-bedroom(+bonus bedroom), 4.5-bath home features an open-concept layout with soaring cathedral ceilings, exposed beams, and a stunning

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  42 Sugar House Rd, West Dover, VT 05356
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  $295,000

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  70 Overlook Dr, Londonderry, VT 05148

  Located close to town but in a private and quiet area, this property offers an affordable option for locals and first-time homebuyers who want to be in one of Vermont’s best little communities and are willing to make the time and investment to turn this house into a home. The house is solid and has been well-maintained, and there are three bedrooms and 1.5 bathrooms and a nice one-level layout

  Claudia Harris Mary Mitchell Miller Real Estate

  70 Overlook Dr, Londonderry, VT 05148
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  /3

  $275,000

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft

  2173 Vermont 8a, Whitingham, VT 05361

  4 bedroom 2 bath home located on 4.7 acres. Has a ground level access. Level parking and garden spots. There are huge White Pine trees surrounding this home. Showings delayed until September 29, 2025 to allow for cleaning. License to Sell is needed and in progress, Expected in October.

  Mark Yule BHG Masiello Brattleboro

  2173 Vermont 8a, Whitingham, VT 05361
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  $57,000

  • 2 Beds
  • 1 Bath
  • 844 Sq Ft

  2036 Vermont 30, Jamaica, VT 05343

  A cozy base for days spent enjoying Vermont country life warmed by a cozy wood stove and enjoying countless meals prepared together in the upgraded cherry and tile kitchen. Property has direct access to the West River. a nice deck to sit on in the back and a nice sitting platform overlooking river. Two bedroom one bath mobile home. Six months occupancy per year. New tenants must be approved by

  Mike England Michael England Real Estate

  2036 Vermont 30, Jamaica, VT 05343
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  $625,000

  • 5 Beds
  • 4 Baths
  • 3,748 Sq Ft

  58 Oak St, Brattleboro, VT 05301

  Come experience the elegance and charm of this stunning in-town retreat! Close to the town common and vibrant downtown Brattleboro—home to fine dining, galleries, quaint shops, and live music venues. Step inside the main house and be welcomed by a country kitchen featuring a large island, ideal for gatherings. The home exudes Victorian character with soaring ceilings, hardwood floors, and

  Rebecca Seymour Brattleboro Area Realty

  58 Oak St, Brattleboro, VT 05301
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  /23

  $135,000

  • Land
  • 5.1 Acres
  • $26,471 per Acre

  1192 Haven Hill Rd, South Londonderry, VT 05155

  This 5+ acre building lot is ready for planning and designing your 5 bedroom dream-home, WW-2-3657 on a quiet country road, and Land Use Permit 2W0032-3. Just minutes to Gale Meadows and Stratton Mountain Resort, there are plenty of summer and winter outdoor adventures to embark on from hiking, kayaking, and fishing in the summer to skiing and snowshoeing in the winter. Only 25-minutes from

  Mike England Michael England Real Estate

  1192 Haven Hill Rd, South Londonderry, VT 05155
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  /18

  $24,000

  • 1 Bed
  • 2 Baths
  • 709 Sq Ft

  106/108 Q3, 89 Grand Summit Way Unit 106/108, Dover, VT 05356

  Enjoy the ski-on, ski-off lifestyle, while also experiencing the luxuries of hotel amenities with this spacious valley facing quarter share unit at the beautiful Grand Summit Hotel, directly at the base of Mount Snow! This unit features TWO decks, one off of each unit, great for après ski and hanging with friends. This sleep 6, lockout unit is perfect for family, guests or great rental options.

  Prema Fitzpatrick Real Broker LLC

  106/108 Q3, 89 Grand Summit Way Unit 106/108, Dover, VT 05356
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  $125,000

  • Land
  • 1.31 Acres
  • $95,420 per Acre

  118 Chimney Hill Rd, Wilmington, VT 05363

  Brand new Quad Lot right on Chimney Hill Road! Former lots M118 & M119 have had two additional parcels added on each end to form a 1.31-Acre Lot suitable for a three-bedroom single family home. Build your dream home and live the all-season resort lifestyle. Chimney Hill Owners Association is located on 1,200 acres adjacent to the Green Mt. National Forest, with 550 acres owned in common by the

  Sigrid Pickering Chimney Hill Realty

  118 Chimney Hill Rd, Wilmington, VT 05363
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  $795,000

  • 3 Beds
  • 3.5 Baths
  • 1,730 Sq Ft

  2A Townhouse Square Unit T-4, Dover, VT 05356

  Experience the best of all worlds! Just 100 feet from your front door, you can hop onto a Mount Snow ski trail, or take a short walk to the newly renovated and expanded, on-site Amenities Center, featuring an indoor pool, outdoor pool, exercise room, saunas, lockers, and more. This beautifully appointed, fully furnished townhome is truly turnkey. Inside, you’ll find two fireplaces—including one

  John Redd Skihome Realty

  2A Townhouse Square Unit T-4, Dover, VT 05356
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  $389,000

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft

  137 Pleasant Valley Rd, Brattleboro, VT 05301

  Welcome to Pleasant Valley Road in beautiful West Brattleboro, Vermont! Lovingly created by the current owner, this incredibly efficient, timber frame home is custom built by a team of local craftsmen. A rare find, designed as an open concept with generous windows providing extraordinary light and connecting you to the outdoors. Insulated beyond expectation, 16 solar panels providing plentiful

  Christine Lewis Brattleboro Area Realty

  137 Pleasant Valley Rd, Brattleboro, VT 05301
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  /39

  $585,000

  • Land
  • 67.63 Acres
  • $8,650 per Acre

  932 Middle Rd, Dummerston, VT 05301

  Discover the perfect blend of peace, privacy, and potential on this 67.63-acre privately owned parcel of land. Nestled in a scenic and serene setting, this expansive property is a rare opportunity to build your dream home, estate, or getaway retreat. Two picturesque ponds – ideal for fishing, wildlife watching, or just enjoying the view. The main home site has amazing mountain views and sits

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  932 Middle Rd, Dummerston, VT 05301
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  $879,900

  • 4 Beds
  • 3.5 Baths
  • 3,300 Sq Ft

  7 Yodeling Ln, West Dover, VT 05356

  Charming Log Home with Modern Comfort and Prime Location. This warm and inviting log home offers the perfect blend of rustic charm and modern style. Nestled on a level lot with ample parking, it features a large covered front porch and a spacious rear deck, ideal for enjoying the beautiful outdoors. Step inside to the main level, where you'll find a welcoming living room anchored by a stunning

  Rich Caplan Deerfield Valley Real Estate

  7 Yodeling Ln, West Dover, VT 05356
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  /29

  $199,000

  • 2 Beds
  • 1 Bath
  • 844 Sq Ft

  8577 Vermont 30 Unit H, Jamaica, VT 05343

  Welcome to The Willows. Where convenience, comfort, and value come together in this well-appointed Condo featuring 2 bedrooms, 1 full bathroom with washer and dryer and updated appliances. Set privately back from Route 30, this thoughtfully maintained unit offers peaceful surroundings just two minutes from Stratton Access Road and within easy reach of Jamaica State Park and the West River. Ideal

  Tara van de Velde Four Seasons Sotheby's Int'l Realty

  8577 Vermont 30 Unit H, Jamaica, VT 05343
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  /35

  $475,000

  • 3 Beds
  • 2 Baths
  • 2,016 Sq Ft

  44 Tanglewood Ln Unit E, Dover, VT 05356

  Welcome to the best Mount Snow view at Timber Creek! This 3 bedroom 2 bath condo has been owned and loved by the same family since its inception. You'll enjoy being right across the street from the North entrance to Mount Snow with access to a free shuttle, along with all the benefits of the Sugarhouse club house and sports complex. There's a basketball court, tennis/pickleball courts,

  Mike Masters Four Seasons Sotheby's Int'l Realty

  44 Tanglewood Ln Unit E, Dover, VT 05356
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  /27

  $2,990,000

  • 4 Beds
  • 4 Baths
  • 4,333 Sq Ft

  56 Coldbrook Crossing, Wilmington, VT 05363

  Spectacular custom home at the base of the Hermitage Club in the Coldbrook Crossing community, adjacent to the base of Haystack mountain. This is a stunning lot overlooking the trails and sunsets beyond, with easy mountain access, snowmobile trail access, and views unimpeded by any other homes. The luxurious features include a vaulted great room with exposed natural wood beams and stone hearth

  Adam Palmiter Berkley & Veller Greenwood/Dover

  56 Coldbrook Crossing, Wilmington, VT 05363
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  /14

  $1,750,000

  • 4 Beds
  • 3.5 Baths
  • 2,698 Sq Ft

  63 Sunbowl Ridge Rd Unit 63A, Stratton, VT 05360

  The absolute best location in one of Stratton's most desirable communities!This four bedroom, three and one half bath townhome is located directly on the ski trail. Immaculate interior. Bright sunny interior with eastern and southern exposure. One car garage, family room, back patio with new hot tub. Private pool and hot tubs located a short walk away. Shuttle service to Stratton base area

  John Sikes Stratton Real Estate

  63 Sunbowl Ridge Rd Unit 63A, Stratton, VT 05360
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  /40

  $849,000

  • 5 Beds
  • 3.5 Baths
  • 3,436 Sq Ft

  67 Castle Hill Rd, Wilmington, VT 05363

  Rare opportunity to own a meticulous 1830s vintage farmhouse, completely turn-key with extensive updates, renovations, and modern amenities. Conveniently located just outside the country village of Wilmington for shopping and great dining options, a short drive to the Mount Snow ski resort, and just up the street from the Lake Whitingham boat launch and beach areas, for true four season

  Adam Palmiter Berkley & Veller Greenwood/Dover

  67 Castle Hill Rd, Wilmington, VT 05363
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  $205,000

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft

  12 Laurel Ave, Bellows Falls, VT 05101

  Move-in ready and full of charm! This well-maintained, beautifully decorated home offers both comfort and convenience in the heart of Bellows Falls. Set on a corner lot within walking distance to town amenities, it features a generously sized kitchen complete with a beverage station and three upstairs bedrooms, providing plenty of space to fit your needs. The manageable lot requires very little

  Linda Benoit Highland Realty

  12 Laurel Ave, Bellows Falls, VT 05101
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  $380,000

  • 7 Beds
  • 5 Baths
  • 3,518 Sq Ft

  343 Haystack Rd, Wilmington, VT 05363

  A perfect home for those looking to renovate and add value. A home with an apartment is located near outdoor recreation spots like Mount Snow and Haystack Country Club ~ mountain riding, state park hiking across from driveway and snowmobile right from your yard. Tucked back on 3 acres with wooded surroundings offering privacy amongst the trees. The main house offers four bedrooms, four baths;

  Jessica Citera Cummings & Co

  343 Haystack Rd, Wilmington, VT 05363
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  /3

  $60,000

  • Land
  • 1.1 Acres
  • $54,545 per Acre

  63 Villager Loop, Dover, VT 05356

  Lovely wooded building site not far from the Mount Snow ski resort, nearby lakes, villages, shopping, and dining. View potential and easy access off a paved road, with a large corner lot location, looking to the west over the ski mountains and sunsets.

  Adam Palmiter Berkley & Veller Greenwood/Dover

  63 Villager Loop, Dover, VT 05356
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  /14

  $210,000

  • Land
  • 35 Acres
  • $6,000 per Acre

  00 Vermont Route 100, Jamaica, VT 05343

  Discover the beauty and tranquility of this picturesque wooded parcel—approximately 35 acres—nestled along the serene Deerfield River and spanning the border of Jamaica and Wardsboro. Perfectly situated within easy reach of Mount Snow, Stratton, and Bromley, the property offers convenient access to year-round recreation while preserving the sense of peace and privacy that only a large forested

  Patrice Schneider Southern Vermont Realty Group

  00 Vermont Route 100, Jamaica, VT 05343
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  /12

  $675,000

  • Land
  • 45 Acres
  • $15,000 per Acre

  000 Under the Mountain Rd, South Londonderry, VT 05155

  Travel down a quiet, tree-lined country road past historic homes, horse farms, and a large nature preserve to discover this magnificent property with views of Stratton and Bromley mountains in the distance. A large open field graced with wild flowers, apple trees and classic Vermont rock walls provides an ideal level home site, protected on three sides by extensive mature woods. The parcel has

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  000 Under the Mountain Rd, South Londonderry, VT 05155
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  /32

  $25,000

  • Land
  • 0.56 Acre
  • $44,643 per Acre

  25 Upper Howes Way, Wilmington, VT 05363

  BUILD your Getaway Section A! Buyer assumes responsibility for pursuing a septic plan and permit, and all costs associated with permitting and building. Lots 25 & 26 are also available and can be combined for a double or triple lot at the end of the road/world. Enjoy the wellness VT lifestyle and all the 1,200-acre resort with our exclusive member-only clubhouse located at 200'

  Sigrid Pickering Chimney Hill Realty

  25 Upper Howes Way, Wilmington, VT 05363
• 

  

  /16

  $19,900

  • Land
  • 0.46 Acre
  • $43,261 per Acre

  00 Country Ct Unit 693, Wilmington, VT 05363

  Attention skiers, golfers, hikers, boaters, VAST lovers, and more! Discover the perfect blend of a country setting, amenities, and convenience with this exceptional land opportunity! This nearly half-acre lot is admirably located within Chimney Hill’s 1,200-acre private resort community with access to a wide range of recreational amenities for both summer and winter enjoyment. Located at the

  Casey Scott Southern Vermont Realty Group

  00 Country Ct Unit 693, Wilmington, VT 05363

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