4,489

South Londonderry, VT Homes

Section Image
  • /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 $212,801

    Last Listing Agent Cheyanne Pugliese

    24 Stratton Rd W, Winhall, VT 05340
    • /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

  • /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
  • /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
    • /17

      Not Listed For Sale

      771 Stratton Mt Access Rd Unit 369-S, Stratton, VT 05155

      • 1 Bed
      • 1 Bath
      • 675 Sq Ft
      • Built 2000
      771 Stratton Mt Access Rd Unit 369-S, Stratton, VT 05155

      Last Sold Summary

      • 37 Days On Market

  • /2

    $45,000

    Under Contract
    • Land
    • 1 Acre
    • $45,000 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    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% of the towns registered voters, the select, Board cannot just sell the property,

    Carrie Mathews Winhall Real Estate

    0 W Hill Rd, Jamaica, VT 05343
  • /20

    $765,000

    Sold Jul 09, 2026

    761 Stratton Mountain Rd Unit 437, Stratton, VT 05155

    • 2 Beds
    • 2 Baths
    • 975 Sq Ft
    • Built 2000

    Last Sold Summary

    • 3% Below List Price
    • $785/SF
    • 29 Days On Market

    Last Listing Agent Edwin Kevil Stratton Real Estate

    761 Stratton Mountain Rd Unit 437, Stratton, VT 05155
    • /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

  • /38

    $625,000

    • 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
  • /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
    • /9

      Not Listed For Sale

      0 Sugarbush Dr Unit Lot D 5025410, Winhall, VT 05340

      0 Sugarbush Dr Unit Lot D 5025410, Winhall, VT 05340

      Last Sold Summary

      • 16 Days On Market

  • /34

    $949,000

    • 3 Beds
    • 3.5 Baths
    • 1,800 Sq Ft

    56 Shattarack Rd Unit D6, Stratton, VT 05360

    Experience ultimate year-round luxury in this tastefully renovated townhome at Slopeside, featuring convenient trail access. Perfectly blending comfort and convenience, this inviting mountain retreat features an updated kitchen and baths, a cozy wood-burning fireplace, and mini-splits for efficient summer cooling. The spacious layout offers three bedrooms plus a private loft complete with its own

    Christina Dryden Berkshire Hathaway HomeServices Stratton Home

    56 Shattarack Rd Unit D6, Stratton, VT 05360
  • /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
    • /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

  • /22

    $430,000

    • 5 Beds
    • 2 Baths
    • 1,664 Sq Ft

    13 Golden Triangle Rd, Winhall, VT 05340

    The ideal opportunity in a prime location, minutes from Stratton Mountain, Bromley Mountain, and the charming town of Manchester, this 5-bedroom, 2-bathroom home has what you need for your primary Vermont residence or a quiet place to getaway. The spacious living room and dining area is complimented by a wrap around porch. This home is low maintenance and setup well for those who want a

    Mike England Michael England Real Estate

    13 Golden Triangle 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
    • /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

  • /53

    $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
  • /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 $650,291

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

    282 Melendy Hill Rd, South Londonderry, VT 05155
    • /48

      Not Listed For Sale

      3702 Vermont Route 100, Londonderry, VT 05148

      • 3 Beds
      • 2 Baths
      • 2,000 Sq Ft
      • Built 1970
      3702 Vermont Route 100, Londonderry, VT 05148

      Last Sold Summary

      • 13 Days On Market

  • /11

    $260,000

    • Land
    • 3.3 Acres
    • $78,788 per Acre

    0 Mountain Haunts Unit 5099438, Winhall, VT 05340

    The 3.3-acre parcel of land located on Mt Haunts Road in Winhall has received approval for the construction of a four-bedroom residence, presenting an outstanding opportunity for prospective homeowners. This exceptional site boasts views of Stratton Mountain Resort, allowing residents to monitor the mountain's snow conditions from the comfort of their own home each morning, as well as enjoy views

    Mike England Michael England Real Estate

    0 Mountain Haunts Unit 5099438, Winhall, VT 05340
  • /35

    $799,000

    Sold Jul 17, 2026

    63 Raspberry Hill Rd, Winhall, VT 05340

    • 4 Beds
    • 3.5 Baths
    • 3,078 Sq Ft
    • Built 1980

    Last Sold Summary

    • $260/SF
    • 9 Days On Market

    Last Listing Agent Carrie Mathews Winhall Real Estate

    63 Raspberry Hill Rd, Winhall, VT 05340
    • /29

      Not Listed For Sale

      43 Styles Branch Rd Unit 1008, Stratton, VT 05360

      • 3 Beds
      • 2.5 Baths
      • 1,778 Sq Ft
      • Built 1979
      43 Styles Branch Rd Unit 1008, Stratton, VT 05360

      Last Sold Summary

      • 102 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
  • /27

    $300,000

    Sold Dec 11, 2025

    0 Rock Bottom Ln, Peru, VT 05152

    • Land
    • 53 Acres
    • $5,660 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 156 Days On Market

    Last Listing Agent David Shehadi Josiah Allen Real Estate, Inc.

    0 Rock Bottom Ln, Peru, VT 05152
    • /7

      Not Listed For Sale

      0 W Hill Rd S Unit 5021406, Jamaica, VT 05343

      0 W Hill Rd S Unit 5021406, Jamaica, VT 05343

      Last Sold Summary

      • 64 Days On Market

  • /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
  • /46

    $1,270,000

    Sold Mar 20, 2026

    33 Forest Haunts Rd, Winhall, VT 05340

    • 4 Beds
    • 4 Baths
    • 4,640 Sq Ft
    • Built 1989

    Last Sold Summary

    • 15% Below List Price
    • $274/SF
    • 487 Days On Market

    Current Estimated Value $1,333,813

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

    33 Forest Haunts Rd, Winhall, VT 05340
    • /22

      Not Listed For Sale

      8581 Vt Route 30 Unit B, Jamaica, VT 05343

      • 2 Beds
      • 1 Bath
      • 691 Sq Ft
      • Built 1982
      8581 Vt Route 30 Unit B, Jamaica, VT 05343

      Last Sold Summary

      • 22 Days On Market

  • /41

    $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
  • /35

    $870,000

    Sold May 13, 2026

    24 Sugarbush Dr, Jamaica, VT 05343

    • 5 Beds
    • 3 Baths
    • 2,897 Sq Ft
    • Built 1974

    Last Sold Summary

    • 2% Above List Price
    • $300/SF
    • 8 Days On Market

    Last Listing Agent Carrie Mathews Winhall Real Estate

    24 Sugarbush Dr, Jamaica, VT 05343
    • /39

      Not Listed For Sale

      5 Red Hickory Rd, Winhall, VT 05340

      • 3 Beds
      • 2 Baths
      • 1,215 Sq Ft
      • Built 1968
      5 Red Hickory Rd, Winhall, VT 05340

      Last Sold Summary

      • 24 Days On Market

  • /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
  • /41

    $1,775,000

    Sold May 08, 2026

    43 Middle Ridge Rd Unit 416, Winhall, VT 05155

    • 4 Beds
    • 4 Baths
    • 2,401 Sq Ft
    • Built 2004

    Last Sold Summary

    • $739/SF
    • 2 Days On Market

    Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

    43 Middle Ridge Rd Unit 416, Winhall, VT 05155
    • /54

      Est $980,547

      Not Listed For Sale

      13 Windtree Rd, Bondville, VT 05340

      • 4 Beds
      • 3.5 Baths
      • 2,672 Sq Ft
      • Built 1994
      13 Windtree Rd, Bondville, VT 05340

      Last Sold Summary

      • 120 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
  • /32

    $350,000

    Sold Mar 20, 2026

    44 Lake Rd, Bondville, VT 05340

    • 5 Beds
    • 3 Baths
    • 2,303 Sq Ft
    • Built 1976

    Last Sold Summary

    • 22% Below List Price
    • $152/SF
    • 5 Days On Market

    Current Estimated Value $378,863

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

    44 Lake Rd, Bondville, VT 05340
    • /22

      Est $230,002

      Not Listed For Sale

      3389 Vt Route 100 N, Londonderry, VT 05148

      • 1 Bed
      • 1 Bath
      • 880 Sq Ft
      • Built 1979
      3389 Vt Route 100 N, Londonderry, VT 05148

      Last Sold Summary

      • 8 Days On Market

  • /55

    $559,000

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

    155 Pratt Bridge Rd, Jamaica, VT 05343

    You may wake up to the singing of Cole Pond resident loons at your next VT home awaiting you just minutes from the Stratton Access road. Tucked away on a quiet country road this inviting 4 bedroom, 2.5 bath home offers the perfect balance of comfort, convenience and charm. Designed for gathering with friends and family, entry level offers a family room with woodstove , open concept on main level

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    155 Pratt Bridge Rd, Jamaica, VT 05343
  • /26

    $795,000

    Sold Aug 21, 2025

    5 Founders Hill Rd, Winhall, VT 05360

    • 3 Beds
    • 3 Baths
    • 1,624 Sq Ft
    • Built 1970

    Last Sold Summary

    • $490/SF
    • 0 Days On Market

    Last Listing Agent Jamie Wylie Stratton Real Estate

    5 Founders Hill Rd, Winhall, VT 05360

Showing Results 201 - 240, Page 6 of 18

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