4,494

South Londonderry, VT Homes

Section Image
  • /14

    $780,000

    Sold Nov 25, 2025

    19 Village Lodge Rd Unit 309, Stratton, VT 05155

    • 2 Beds
    • 2 Baths
    • 1,263 Sq Ft
    • Built 2000

    Last Sold Summary

    • 4% Below List Price
    • $618/SF
    • 46 Days On Market

    Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

    19 Village Lodge Rd Unit 309, Stratton, VT 05155
    • /60

      Est $1,980,483

      Not Listed For Sale

      18 Rocky Dell Rd, Winhall, VT 05340

      • 7 Beds
      • 5.5 Baths
      • 6,195 Sq Ft
      • Built 2007
      18 Rocky Dell Rd, Winhall, VT 05340

      Last Sold Summary

      • 246 Days On Market

  • /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
  • /40

    $1,000,000

    Sold Feb 24, 2026

    19 Roundtree Rd, Bondville, VT 05340

    • 4 Beds
    • 2.5 Baths
    • 3,086 Sq Ft
    • Built 1978

    Last Sold Summary

    • 2% Below List Price
    • $324/SF
    • 80 Days On Market

    Current Estimated Value $1,006,033

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    19 Roundtree Rd, Bondville, VT 05340
    • /21

      Not Listed For Sale

      38 Quarter Mile Rd, Winhall, VT 05360

      • 4 Beds
      • 4 Baths
      • 1,940 Sq Ft
      • Built 1970
      38 Quarter Mile Rd, Winhall, VT 05360

      Last Sold Summary

      • 9 Days On Market

  • /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
  • /44

    $702,000

    Sold Oct 24, 2025

    86 Benson Fuller Dr, Bondville, VT 05340

    • 4 Beds
    • 2 Baths
    • 2,040 Sq Ft
    • Built 1983

    Last Sold Summary

    • 6% Below List Price
    • $344/SF
    • 42 Days On Market

    Current Estimated Value $688,047

    Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    86 Benson Fuller Dr, Bondville, VT 05340
    • /40

      Est $1,730,237

      Not Listed For Sale

      82 High Meadow Rd, Winhall, VT 05340

      • 6 Beds
      • 5.5 Baths
      • 4,551 Sq Ft
      • Built 2002
      82 High Meadow Rd, Winhall, VT 05340

      Last Sold Summary

      • 126 Days On Market

  • /8

    $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
  • /20

    $500,000

    Sold Nov 26, 2025

    374 Winhall Hollow Rd, Winhall, VT 05340

    • 4 Beds
    • 3 Baths
    • 1,920 Sq Ft
    • Built 1986

    Last Sold Summary

    • 1% Above List Price
    • $260/SF
    • 3 Days On Market

    Current Estimated Value $495,313

    Last Listing Agent Annette Gallo Real Broker LLC

    374 Winhall Hollow Rd, Winhall, VT 05340
    • /24

      Est $517,439

      Not Listed For Sale

      13 Lower Taylor Hill Rd, Winhall, VT 05340

      • 3 Beds
      • 2.5 Baths
      • 1,716 Sq Ft
      • Built 1967
      13 Lower Taylor Hill Rd, Winhall, VT 05340

      Last Sold Summary

      • 26 Days On Market

  • /34

    $579,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,455 Sq Ft

    4 Pearl Buck Dr, Winhall, VT 05340

    Just minutes from the slopes of Stratton Mountain Resort, this three bedroom plus den, two bath home offers an easy four season retreat with stunning views of Stratton Mountain. Set on 2 acres, it gives you convenient access to everything the area is known for, from winter ski days to summer mountain biking, golf, hiking, and village events. The home has been thoughtfully improved over time,

    Andie Fusco Four Seasons Sotheby's Int'l Realty

    4 Pearl Buck Dr, Winhall, VT 05340
  • /22

    $445,000

    Sold Sep 16, 2025

    163 Vt Route 30, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,590 Sq Ft
    • Built 1970

    Last Sold Summary

    • 1% Below List Price
    • $280/SF
    • 13 Days On Market

    Current Estimated Value $442,030

    Last Listing Agent Timothy Apps Four Seasons Sotheby's Int'l Realty

    163 Vt Route 30, Winhall, VT 05340
    • /31

      Not Listed For Sale

      71 Todd Hill Rd, Jamaica, VT 05343

      • 5 Beds
      • 5.5 Baths
      • 3,624 Sq Ft
      • Built 2006
      71 Todd Hill Rd, Jamaica, VT 05343

      Last Sold Summary

      • 4 Days On Market

  • /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
  • /43

    $547,500

    Sold Dec 29, 2025

    66 Hilltop Rd, Londonderry, VT 05155

    • 4 Beds
    • 2.5 Baths
    • 2,149 Sq Ft
    • Built 1970

    Last Sold Summary

    • 5% Below List Price
    • $255/SF
    • 49 Days On Market

    Last Listing Agent Alison Cummings Cummings & Co

    66 Hilltop Rd, Londonderry, VT 05155
    • /25

      Not Listed For Sale

      16 Ober Tal Dr Unit E35, Stratton, VT 05360

      • 2 Beds
      • 2 Baths
      • 1,096 Sq Ft
      • Built 1983
      16 Ober Tal Dr Unit E35, Stratton, VT 05360

      Last Sold Summary

      • 2 Days On Market

  • /5

    $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, 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 Mount Snow, ideal for

    Mike England Michael England Real Estate

    000F-320 Bourbon Run Rd, Jamaica, VT 05343
  • /29

    $526,000

    Sold Aug 08, 2025

    176 Pratt Bridge Rd, Jamaica, VT 05343

    • 3 Beds
    • 2.5 Baths
    • 1,620 Sq Ft
    • Built 1965

    Last Sold Summary

    • 4% Below List Price
    • $325/SF
    • 36 Days On Market

    Current Estimated Value $515,494

    Last Listing Agent Carrie Mathews Winhall Real Estate

    176 Pratt Bridge Rd, Jamaica, VT 05343
    • /21

      Not Listed For Sale

      61 Birch Hill Rd Unit 6, Winhall, VT 05340

      • 3 Beds
      • 2 Baths
      • 1,215 Sq Ft
      • Built 1968
      61 Birch Hill Rd Unit 6, Winhall, VT 05340

      Last Sold Summary

      • 42 Days On Market

  • /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
  • /2

    $205,000

    Sold Sep 15, 2025

    24 Stratton Rd W, Winhall, VT 05340

    • 2 Beds
    • 1 Bath
    • 665 Sq Ft
    • Built 1970

    Last Sold Summary

    • $308/SF
    • 0 Days On Market

    Current Estimated Value $206,029

    Last Listing Agent Cheyanne Pugliese

    24 Stratton Rd W, Winhall, VT 05340
    • /14

      Not Listed For Sale

      759 Stratton Mountain Access Rd Unit 331, Stratton, VT 05340

      • 3 Beds
      • 2.5 Baths
      • 1,780 Sq Ft
      • Built 2004
      759 Stratton Mountain Access Rd Unit 331, Stratton, VT 05340

      Last Sold Summary

      • 12 Days On Market

  • /21

    $340,000

    $39K PRICE DROP
    • Land
    • 12.05 Acres
    • $28,216 per Acre

    101 Catherine Rd, Jamaica, VT 05343

    Discover 12 scenic acres close to Stratton Mountain Resort with sweeping mountain views and endless potential. This unique property features a charming small treehouse and two Jamaica cottage structures set on permanent foundations ready to be finished. Cabin would be perfect for income producing tiny homes, storage, creative space, or future development. An active septic permit is already in

    Jamie Wylie Stratton Real Estate

    101 Catherine Rd, Jamaica, VT 05343
  • /53

    $775,000

    Sold Aug 13, 2025

    E12 Rock Ridge Rd, Winhall, VT 05155

    • 3 Beds
    • 3 Baths
    • 1,842 Sq Ft
    • Built 1986

    Last Sold Summary

    • 3% Below List Price
    • $421/SF
    • 7 Days On Market

    Last Listing Agent Cheyanne Pugliese

    E12 Rock Ridge Rd, Winhall, VT 05155
    • /53

      Not Listed For Sale

      324 Pikes Falls Rd, South Londonderry, VT 05155

      324 Pikes Falls Rd, South Londonderry, VT 05155

      Last Sold Summary

      • 102 Days On Market

  • /39

    $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
  • /2

    $400,000

    Sold Mar 09, 2026

    97 N Branch Rd, Winhall, VT 05155

    • Land
    • 1.18 Acres
    • $338,983 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 29 Days On Market

    Last Listing Agent John Sikes Stratton Real Estate

    97 N Branch Rd, Winhall, VT 05155
    • /30

      Not Listed For Sale

      21 Stratton Ridge Rd, Winhall, VT 05340

      • 3 Beds
      • 1.5 Baths
      • 1,088 Sq Ft
      • Built 1970
      21 Stratton Ridge Rd, Winhall, VT 05340

      Last Sold Summary

      • 115 Days On Market

  • /27

    $609,000

    • 4 Beds
    • 3 Baths
    • 1,650 Sq Ft

    60 Hilltop Rd Unit 60, Winhall, VT 05340

    Turn-key Stratton retreat in one of the area’s most desirable year-round communities. This 4-bedroom, 3-bath Intervale townhome offers the perfect blend of comfort and convenience—just minutes to the slopes with seasonal shuttle service right from the community. The open-concept living area is ideal for gathering after a day on the mountain, while five mini-split systems provide efficient heating

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    60 Hilltop Rd Unit 60, Winhall, VT 05340
  • /12

    $935,000

    Sold Mar 31, 2026

    759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340

    • 3 Beds
    • 3 Baths
    • 1,501 Sq Ft
    • Built 2005

    Last Sold Summary

    • 15% Below List Price
    • $623/SF
    • 313 Days On Market

    Last Listing Agent John Sikes Stratton Real Estate

    759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340
    • /39

      Not Listed For Sale

      52 Snow Bridge Rd, Stratton, VT 05360

      • 4 Beds
      • 3.5 Baths
      • 2,244 Sq Ft
      • Built 1997
      52 Snow Bridge Rd, Stratton, VT 05360

      Last Sold Summary

      • 10 Days On Market

  • /15

    $500,000

    • Land
    • 21.2 Acres
    • $23,585 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
  • /22

    $407,000

    Sold Oct 08, 2025

    7 Wanderer Rd Unit 7, Stratton, VT 05155

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1970

    Last Sold Summary

    • 5% Above List Price
    • $291/SF
    • 6 Days On Market

    Last Listing Agent Dan McKenna Cummings & Co

    7 Wanderer Rd Unit 7, Stratton, VT 05155
    • /5

      Not Listed For Sale

      0 Karen Dr Unit Lot 12 5021748, Jamaica, VT 05343

      0 Karen Dr Unit Lot 12 5021748, Jamaica, VT 05343

      Last Sold Summary

      • 11 Days On Market

  • /55

    $950,000

    $45K PRICE DROP Under Contract
    • 5 Beds
    • 4.5 Baths
    • 2,321 Sq Ft

    24 N Branch Rd, Winhall, VT 05340

    Location says it all ! Stratton Quarter Mile neighborhood on Shuttle, just a short walk home from the Village. This exceptional renovation offers an expanded floor plan with a third level.Beautiful upscale baths with tile work and craftsmanship of the highest caliber. Wood floors throughout. Open gourmet kitchen makes for premier apres ski gatherings. With 5 bedrooms/4 baths and multiple ensuite-

    Kim Morgan-Wohler Wohler Realty Group

    24 N Branch Rd, Winhall, VT 05340
  • /22

    $265,500

    Sold Jul 15, 2025

    18 Stratton Ridge Rd, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,332 Sq Ft
    • Built 1970

    Last Sold Summary

    • 16% Below List Price
    • $199/SF
    • 72 Days On Market

    Last Listing Agent Derek Greene Derek Greene

    18 Stratton Ridge Rd, Winhall, VT 05340
    • /52

      Not Listed For Sale

      E11 Rock Ridge Rd, Winhall, VT 05155

      • 3 Beds
      • 3 Baths
      • 2,300 Sq Ft
      • Built 1986
      E11 Rock Ridge Rd, Winhall, VT 05155

      Last Sold Summary

      • 47 Days On Market

  • /39

    $495,000

    Under Contract
    • 4 Beds
    • 2 Baths
    • 1,824 Sq Ft

    140 Vermont 30, Winhall, VT 05340

    Quintessential Vermont charm meets modern comfort in this beautifully updated New England farmhouse just minutes from Stratton Mountain. Ideally located only 1 mile from the Stratton Mountain Access Road and just 1/10 mile to the VAST snowmobile trail, this 4-bedroom, 2-bath home offers the perfect four-season retreat. Rich with character, the home features exposed beams, warm hardwood floors,

    Carrie Mathews Winhall Real Estate

    140 Vermont 30, Winhall, VT 05340
  • /35

    $649,000

    Sold Dec 04, 2025

    282 Melendy Hill Rd, South Londonderry, VT 05155

    • 3 Beds
    • 3 Baths
    • 2,939 Sq Ft
    • Built 1991

    Last Sold Summary

    • $221/SF
    • 26 Days On Market

    Current Estimated Value $636,661

    Last Listing Agent Kevin Moran Four Seasons Sotheby's Int'l Realty

    282 Melendy Hill Rd, South Londonderry, VT 05155

Showing Results 161 - 200, Page 5 of 18

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