South Londonderry, VT Homes for Sale with Acreage

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  /41

  $950,000

  • 4 Beds
  • 3.5 Baths
  • 3,031 Sq Ft

  7 Roundtree Rd, Winhall, VT 05340

  Discover the perfect mountain retreat at 7 Roundtree Road, a contemporary and beautifully designed 4-bedroom home set on 1.37 private acres in one of Stratton’s most sought-after neighborhoods. Ideally located just a quick drive to the Base Lodge—or simply hop on the convenient shuttle for effortless access to the slopes—this property offers the best of Stratton living in every season.Step

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  7 Roundtree Rd, Winhall, VT 05340
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  /9

  $85,000

  $30K PRICE INCREASE

  • Land
  • 1 Acre
  • $85,000 per Acre

  000F-320 Bourbon Run Rd, Jamaica, VT 05343

  This 1-acre wooded lot in Jamaica permitted for a 3 bedroom , Vermont offers a unique opportunity for peaceful living in a quiet town with no zoning restrictions. Jamaica maintains its own roads and is home to a State Park that provides excellent camping and summer recreational activities. The property is conveniently located near major ski resorts including Stratton, Bromley, Magic Mountain, and

  Mike England Michael England Real Estate

  000F-320 Bourbon Run Rd, Jamaica, VT 05343
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  /15

  $825,000

  • Land
  • 77.6 Acres
  • $10,631 per Acre

  0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340

  Large wooded parcel located in the heart of Southern Vermont’s ski country, just minutes from Stratton Mountain. This undeveloped Winhall property offers a rare opportunity for a variety of potential uses, from a private estate to recreational land or possible future development. The land consists primarily of wooded acreage with a gently rolling landscape and natural Vermont forest. Located on

  Trent Stephens Wohler Realty Group

  0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340
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  /41

  $1,600,000

  $150K PRICE DROP

  • 7 Beds
  • 5 Baths
  • 4,649 Sq Ft

  4669 Vermont Route 100, Londonderry, VT 05148

  Encompassing over 200 acres of pasture and forest, Timberland Farm is anchored by an early 1800s farmhouse that feels at once timeless and lived-in, a place shaped by centuries of stories, music, and shared meals. The living spaces feel both intimate and generous, framed by hand-hewn beams and original wide pine floors. From the dining room to the music room, wood-burning fireplaces crowned with

  Story Jenks LandVest, Inc/Woodstock

  4669 Vermont Route 100, Londonderry, VT 05148
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  /14

  $450,000

  $50K PRICE DROP

  • Land
  • 21.2 Acres
  • $21,226 per Acre

  56 Lower Taylor Hill Rd, Winhall, VT 05340

  Set along Lower Taylor Hill Road in Winhall, this 21.2 +/- acre offering captures the privacy, natural beauty, and four-season lifestyle that define Southern Vermont living. Rolling terrain, mature woodland, and natural clearings create an exceptional setting for a private Vermont retreat, with the potential for Bromley Mountain views depending on house placement and design.Supported by a

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  56 Lower Taylor Hill Rd, Winhall, VT 05340
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  /5

  $375,000

  $90K PRICE DROP

  • Land
  • 5.54 Acres
  • $67,690 per Acre

  Lot #4 Margeaux Ln, Stratton, VT 05155

  Nestled along a peaceful babbling brook, this 5.54-acre parcel offers an idyllic setting for building the home of your dreams. Surrounded by a serene wooded landscape, the property provides both privacy and tranquility, while still being just moments from the Sun Bowl at Stratton. With a septic permit already approved for a 4-bedroom home, this lot is ready for construction, allowing you to begin

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  Lot #4 Margeaux Ln, Stratton, VT 05155
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  /59

  $949,000

  $30K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 5,248 Sq Ft

  41-43 Cranberry Hill Rd, Winhall, VT 05340

  This is the ultimate modern Alpine chalet, fully renovated yet boasting the classic flat-sawn balusters characteristic of mountain homes in the Alps. Three expansive floors offer sunny, well-appointed space, beginning with a roomy mudroom, three bedrooms and two bathrooms (one en-suite). Head upstairs to join your friends and family in the open-concept European kitchen/living/dining room with

  Jamie Luke TPW Real Estate

  41-43 Cranberry Hill Rd, Winhall, VT 05340
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  /2

  $50,000

  • Land
  • 28 Acres
  • $1,786 per Acre

  non Pikes Falls Rd, Jamaica, VT 05343

  This is a land locked parcel. There is no right of way or easement to access it. This is a town sale property. There is a 30 day waiting period after a fully executed contract. The 30 days is a window for public feedback. Under the statute, if Town residence object to the sale, they have 30 days from the date of the notice to submit a petition to the Town. If a petition is signed by at least 5%

  Carrie Mathews Winhall Real Estate

  non Pikes Falls Rd, Jamaica, VT 05343
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  /6

  $395,000

  $100K PRICE DROP

  • Land
  • 6.93 Acres
  • $56,999 per Acre

  lot#2 Margeaux Ln, Stratton, VT 05155

  This stunning 6.93-acre parcel offers the perfect setting to build the home of your dreams, just moments from the Sun Bowl at Stratton. Nestled in a serene wooded landscape, the property provides both privacy and tranquility while being ideally located for easy access to all that Stratton has to offer. With a septic permit already approved for a 4-bedroom home, this lot is ready for you to begin

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  lot#2 Margeaux Ln, Stratton, VT 05155
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  /21

  $160,000

  • Land
  • 11.08 Acres
  • $14,440 per Acre

  0 Rose Ln Unit 5097818, Londonderry, VT 05148

  This 11-acre parcel is situated near Cole Pond, only a few miles from the Stratton Mountain Access Road. The lot offers several potential building sites, including an elevated area that boasts stunning views, as well as a lower option. A driveway extends approximately halfway up the property, providing access to the upper site, which features a remarkable vista of Bromley Mountain. As one

  Mike England Michael England Real Estate

  0 Rose Ln Unit 5097818, Londonderry, VT 05148
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  /54

  $1,990,000

  • 6 Beds
  • 6.5 Baths
  • 5,896 Sq Ft

  27 Mountain View Rd, Winhall, VT 05360

  Direct views of Stratton Mountain set the stage for this exceptional post-and-beam residence, offering a rare combination of luxury living, entertaining space, and rental flexibility. Handcrafted timber framing creates warmth and character throughout, while four fireplaces including a gas fireplace in the primary suite enhance the home's mountain atmosphere. Designed for gathering, the lower

  Jamie Wylie Stratton Real Estate

  27 Mountain View Rd, Winhall, VT 05360
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  /47

  $1,225,000

  • 4 Beds
  • 3 Baths
  • 3,357 Sq Ft

  153 High Meadow Rd, Winhall, VT 05340

  Located in Stratton Resort’s sought-after High Meadow community, this beautifully maintained and turnkey home offers the perfect blend of comfort, convenience, and mountain charm. Filled with natural light, the home features four bedrooms and three recently updated full baths, along with hardwood floors, cathedral ceilings, skylights, and a stunning floor-to-ceiling brick fireplace. Recent

  Britt Wohler

  153 High Meadow Rd, Winhall, VT 05340
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  /37

  $839,000

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

  42 Blackberry Ln, Jamaica, VT 05343

  Only 8 miles from Stratton Mountain, this extra-large expanded farmhouse provides ample space, quiet, and tons of classic Vermont charm. Set in a lush garden landscape surrounded by meadows, a stone wall, perennial gardens, an apple orchard, a barn, & multiple outbuildings, the home feels like old Vermont while being close to major amenities. The original home is from the 19th century but

  Cheyanne Pugliese

  42 Blackberry Ln, Jamaica, VT 05343
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  /15

  $215,000

  • 2 Beds
  • 1 Bath
  • 691 Sq Ft

  8581 Vermont 30 Unit B, Jamaica, VT 05343

  Escape to the mountains in this charming 2-bedroom/1 bath condominium conveniently located near premier ski areas and year-round outdoor recreation. It's only 15 minutes to Stratton, 20 minutes to Bromley, and 10 to the Jamaica State Park. Enjoy easy access to skiing, hiking, biking, golf, and snowmobile trails, all just minutes from your door, and Manchester's shopping and dining are 30 minutes

  Deborah Hanst

  8581 Vermont 30 Unit B, Jamaica, VT 05343

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