South Londonderry, VT Homes for Sale with Acreage

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  $2,430,000

  $270K PRICE DROP

  • 9 Beds
  • 7 Baths
  • 4,996 Sq Ft

  494-564 Goodaleville Rd, Jamaica, VT 05343

  TWO HOMES | 1BR BARN APARTMENT | RESTORED VINTAGE BARN | 13+ ACRES. A rare Vermont multi-residence estate offering two beautifully renovated homes, a separate 1BR barn apartment, a restored vintage barn, and more than 13 acres along the Winhall River. Thoughtfully renovated by Vermont Country Builders, Winhall River Farm blends authentic character, exceptional craftsmanship, and modern

  Cheyanne Pugliese

  494-564 Goodaleville Rd, Jamaica, VT 05343
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  /31

  $1,200,000

  • 1 Bath
  • 950 Sq Ft

  109 Winhall Hollow Rd, Winhall, VT 05340

  Experience the pinnacle of Green Mountain living on this extraordinary 23.5-acre property. Perfectly positioned to capture a stunning, direct-line-of-sight view of Stratton Mountain, this property is more than just a home—it is a private outdoor sanctuary meticulously designed by The Wadsworth Company for the modern adventurer. The centerpiece of the property is a striking, contemporary dwelling

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  109 Winhall Hollow Rd, Winhall, VT 05340
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  $765,000

  • 3 Beds
  • 3 Baths
  • 2,322 Sq Ft

  72 Benson Fuller Dr, Winhall, VT 05340

  Set among the trees just minutes from Stratton Resort, this spacious 3-bedroom, 3-bath mountain home combines beautiful views, flexible living spaces and plenty of room for family and friends. The dramatic main living area features soaring vaulted ceilings, warm wood accents, a floor-to-ceiling stone fireplace and an impressive wall of windows that fills the home with natural light and brings the

  Christine Chovan

  72 Benson Fuller Dr, Winhall, VT 05340
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  $605,000

  $20K PRICE DROP

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

  1 Beaver St, Bondville, VT 05340

  Ideally located between Manchester and the mountains, this home offers the perfect blend of convenience, comfort, and Vermont charm. Just 10 minutes to Stratton, 5 minutes to Bromley, and 12 minutes to Manchester, you’ll enjoy easy access to skiing, dining, shopping, and year-round recreation.Inside, the home features a spacious living room filled with natural light, creating a warm and

  Carrie Mathews Winhall Real Estate

  1 Beaver St, Bondville, VT 05340
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  $4,500,000

  • 5 Beds
  • 5.5 Baths
  • 5,700 Sq Ft

  24 Sawmill Rd, Stratton, VT 05360

  Experience the ultimate Stratton Mountain lifestyle from this exceptional ski home, perfectly positioned in one of the resort's most coveted locations. Offering the rare advantage of deeded access to Stratton's impeccably groomed ski trail, this extraordinary property places world-class skiing just steps from your front door—an amenity few homes can claim and even fewer can match.Designed for

  Carrie Mathews Winhall Real Estate

  24 Sawmill Rd, Stratton, VT 05360
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  /40

  $1,325,000

  • 4 Beds
  • 3.5 Baths
  • 3,400 Sq Ft

  11 W Round Rd, Winhall, VT 05340

  11 Round Tree Road, Winhall, VT 05340A landmark on Round Tree Road, this house has inviting curb appeal with its stone façade and archway. With 1.83 acres the house has a very private setting in back for the patio, fire pit and hot tub. Unique U-shaped driveway has plenty of room for friends and family. Appropriately sized mud room for all the gear. Downstairs family room with fireplace and

  Andrew King Stratton Real Estate

  11 W Round Rd, Winhall, VT 05340
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  /9

  $195,000

  • Land
  • 1.2 Acres
  • $162,500 per Acre

  4769 Pikes Falls Rd, Jamaica, VT 05143

  This 1.2-acre parcel offers what few properties in Southern Vermont can—a front-row seat to one of the region’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this land enjoys immediate proximity to a setting protected by the Conservation Society of Southern Vermont. Glamping has become one of Vermont’s most sought-after experiences, and this

  Rachel Febbie EXP Realty

  4769 Pikes Falls Rd, Jamaica, VT 05143
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  /12

  $150,000

  $25K PRICE DROP

  • Land
  • 2.26 Acres
  • $66,372 per Acre

  0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340

  Welcome to the Stratton Gardens Community. Build your Vermont home on this 2+ acre parcel in Stratton Gardens. Ease of access right off the Stratton Mountain Access Road, and all the amenities of Stratton Gardens Association- highlights include-Private Shuttle Bus service to the Mountain, Road Maintenance, Plowing, Landscaping, and Trash removal.State Waste Water Permit in place for approved

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

  0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340
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  $910,000

  $40K PRICE DROP

  • 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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  $599,000

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  33 Burnt Hill Ln, Winhall, VT 05340

  Experience four season Vermont living at 33 Burnt Hill Road in Strattonwald, a recreational community in Winhall just minutes from Stratton Mountain. Set on 1.09 wooded acres, this three bedroom, two bath mountain home combines privacy and Vermont character with access to the Strattonwald swimming pond and beach, tennis courts and winter shuttle service to Stratton.Inside, natural wood,

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  33 Burnt Hill Ln, Winhall, VT 05340
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  $5,575,000

  • 7 Beds
  • 9.5 Baths
  • 9,915 Sq Ft

  159 Winhall Hollow Rd, Bondville, VT 05340

  Privately situated in a most beautiful setting, this grand Vermont estate commands a remarkable landscape, with Stratton Mountain rising majestically beyond the tree line. A sweeping private drive sets the tone for an extraordinary arrival; open meadows, a serene pond, and beautifully preserved grounds before revealing the 9915 SF residence itself and massive barn. There's an immediate sense of

  Kim Morgan-Wohler Wohler Realty Group

  159 Winhall Hollow Rd, Bondville, VT 05340
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  $65,000

  $10K PRICE INCREASE

  • Land
  • 1 Acre
  • $65,000 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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  /11

  $240,000

  • Land
  • 10.06 Acres
  • $23,857 per Acre

  0 Stratton Gardens Rd Unit 35, Winhall, VT 05340

  This expansive building lot, situated just off the Stratton Access Road, offers breathtaking views of Bromley Mountain, presenting an ideal opportunity to construct your dream home in the picturesque setting of Stratton, Vermont. The property is designated for a five-bedroom residence, with the necessary State Waste permit (WW-2-1972-14) already in place, ensuring a smooth development process.

  Mike England Michael England Real Estate

  0 Stratton Gardens Rd Unit 35, Winhall, VT 05340
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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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  $1,150,000

  • 4 Beds
  • 5.5 Baths
  • 3,206 Sq Ft

  11 Spruce High Rd, Winhall, VT 05340

  Discover this truly exceptional Vermont Mountain Retreat just seven miles from Stratton Mountain, perfectly located for four-season living! Boasting an inviting open layout great for spending time together, southern exposure and an abundance of natural light this beautifully renovated home has been updated in a sophisticated Vermont rustic style with all the comforts. Enjoy the Luxurious primary

  Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

  11 Spruce High 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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  $5,100,000

  • 10 Beds
  • 9.5 Baths
  • 6,648 Sq Ft

  15 Sawmill Rd, Stratton, VT 05155

  Location, Location, Location. Representing the pinnacle of Stratton Mountain trailside living, 15 Sawmill is a generational property where unrivaled ski-in/ski-out access creates one of Stratton's most exceptional legacy offerings. This is one of the few homes located along the trail - one you admire and wish was yours when you ski by it all winter season! Perfectly positioned directly on the ski

  Kim Morgan-Wohler Wohler Realty Group

  15 Sawmill Rd, Stratton, VT 05155
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  $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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  $152,000

  $8K PRICE DROP

  • Land
  • 11.08 Acres
  • $13,718 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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  $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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  $799,000

  $40K PRICE DROP

  • 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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  $500,000

  • Land
  • 20.2 Acres
  • $24,752 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  Mike England Michael England Real Estate

  0 W Hill Rd, Jamaica, VT 05343

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