4,475

South Londonderry, VT Homes

Section Image
  • /22

    $360,000 Sold Jun 20, 2025

    9 Mountain Acres Rd, Jamaica, VT 05343

    • 5 Beds
    • 2 Baths
    • 1,430 Sq Ft
    • Built 1960

    Last Sold Summary

    • 3% Below List Price
    • $252/SF
    • 112 Days On Market

    Current Estimated Value $375,451

    Last Listing Agent Helen Nault

    9 Mountain Acres Rd, Jamaica, VT 05343
    • /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

      • $309/SF
      • 102 Days On Market
      • Last Sold Price $550,000
      • Mar 28, 2025

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

  • /12

    $299,999

    • Land
    • 10.05 Acres
    • $29,851 per Acre

    00 Garden Loop Rd, Winhall, VT 05340

    The largest remaining vacant lot on the Stratton Mountain access road. Ten acres deeded for one magnificent home. The lot is wooded with some clearing on the east side. There's a roughed-in driveway here too, making it the best spot for construction. In the center of the property is a small pond--about a tenth of an acre--and west of that a scenic perennial creek winds its way downhill along the

    David White OwnerEntry.com

    00 Garden Loop Rd, Winhall, VT 05340
  • /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
      • Last Sold Price $115,000
      • Feb 20, 2025

      Last Listing Agent Thom Milke Fountains Land Inc.

  • /40

    $1,650,000 Under Contract

    • 9 Beds
    • 9 Baths
    • 8,054 Sq Ft

    207 Brooks Ln, Londonderry, VT 05148

    This extraordinary, fully furnished property boasts an abundance of amenities and natural splendor. Revel in the awe-inspiring views and the tranquil swimming pond spread across these extensive 69 acres. Delight in the winding trails that lead to 1,235 feet of pristine West River frontage, providing year-round outdoor activities for all. With three distinct residences and a charming cabin, it

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    207 Brooks Ln, Londonderry, VT 05148
  • /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 $1,335,445

    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

      • $268/SF
      • 22 Days On Market
      • Last Sold Price $185,000
      • Jun 10, 2024

      Last Listing Agent Christina Dryden Berkshire Hathaway HomeServices Stratton Home

  • /39

    $895,000 Under Contract

    • 4 Beds
    • 4 Baths
    • 2,673 Sq Ft

    F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340

    Own your piece of Piper Ridge, a prestigious condo complex, in Stratton, Vermont. This 4-bedroom, 4-bathroom townhome received significant improvements over the past two years, making it move-in ready for maximum relaxation in the mountains. This spacious open floor plan has been upgraded with new hardwood flooring on the first and second floors and kitchen renovations with new countertops and

    Mike England Michael England Real Estate

    F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340
  • /39

    $1,750,000 Sold May 09, 2025

    34 Mountain Reach Mews Rd, Stratton, VT 05155

    • 4 Beds
    • 4 Baths
    • 2,653 Sq Ft
    • Built 1986

    Last Sold Summary

    • 3% Below List Price
    • $660/SF
    • 87 Days On Market

    Last Listing Agent Heidi Zizza Four Seasons Sotheby's Int'l Realty

    34 Mountain Reach Mews Rd, Stratton, VT 05155
    • /22

      Est $217,235 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

      • 4% Above List Price
      • $236/SF
      • 8 Days On Market
      • Last Sold Price $208,000
      • Jan 30, 2025

      Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  • /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
  • /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 $448,702

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

    44 Lake Rd, Bondville, VT 05340
    • /59

      Est $5,492,716 Not Listed For Sale

      64 Tamarack Rd, Stratton, VT 05360

      • 9 Beds
      • 10.5 Baths
      • 7,498 Sq Ft
      • Built 2014
      64 Tamarack Rd, Stratton, VT 05360

      Last Sold Summary

      • 7% Above List Price
      • $687/SF
      • 93 Days On Market
      • Last Sold Price $5,150,000
      • Mar 12, 2025

      Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

  • /8

    $150,000

    • 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
  • /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
    • /27

      Not Listed For Sale

      771 Stratton Mnt Access Rd Unit 371, Stratton, VT 05155

      • 2 Beds
      • 2 Baths
      • 1,071 Sq Ft
      • Built 1999
      771 Stratton Mnt Access Rd Unit 371, Stratton, VT 05155

      Last Sold Summary

      • $567/SF
      • 8 Days On Market
      • Last Sold Price $607,500
      • Nov 26, 2024

      Last Listing Agent Robert Sabol Wohler Realty Group

  • /34

    $579,000

    • 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

    $389,000 Sold Feb 23, 2026

    2 Lower Stratton Valley Rd, Winhall, VT 05340

    • 4 Beds
    • 1.5 Baths
    • 1,344 Sq Ft
    • Built 1978

    Last Sold Summary

    • $289/SF
    • 26 Days On Market

    Current Estimated Value $402,301

    Last Listing Agent Mike Masters Four Seasons Sotheby's Int'l Realty

    2 Lower Stratton Valley Rd, Winhall, VT 05340
    • /33

      Not Listed For Sale

      792 Stratton Mountain Rd Unit 4527, Stratton, VT 05360

      • 2 Beds
      • 2 Baths
      • 1,208 Sq Ft
      • Built 1983
      792 Stratton Mountain Rd Unit 4527, Stratton, VT 05360

      Last Sold Summary

      • $650/SF
      • 7 Days On Market
      • Last Sold Price $785,000
      • Dec 04, 2024

      Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

  • /5

    $55,000

    • Land
    • 1 Acre
    • $55,000 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
  • /56

    $3,750,000 Sold Oct 30, 2025

    192 N Brookwood Rd, Stratton, VT 05360

    • 7 Beds
    • 7.5 Baths
    • 6,900 Sq Ft
    • Built 1988

    Last Sold Summary

    • $543/SF
    • 16 Days On Market

    Current Estimated Value $3,818,011

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    192 N Brookwood Rd, Stratton, VT 05360
    • /5

      Not Listed For Sale

      15 Mountain Reach Mews Unit 15, Stratton, VT 05360

      • 4 Beds
      • 6 Baths
      • 3,422 Sq Ft
      • Built 1986
      15 Mountain Reach Mews Unit 15, Stratton, VT 05360

      Last Sold Summary

      • $1,081/SF
      • 0 Days On Market
      • Last Sold Price $3,700,000
      • Oct 07, 2024

      Last Listing Agent Andrew King Stratton Real Estate

  • /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

    $422,000 Sold Oct 24, 2025

    486 Windy Rise Ln E, Londonderry, VT 05148

    • 3 Beds
    • 3 Baths
    • 1,600 Sq Ft
    • Built 1975

    Last Sold Summary

    • 15% Below List Price
    • $264/SF
    • 21 Days On Market

    Current Estimated Value $448,632

    Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    486 Windy Rise Ln E, Londonderry, VT 05148
    • /29

      Est $472,886 Not Listed For Sale

      10 Ober Tal Dr Unit B32, Stratton, VT 05360

      • 2 Beds
      • 2 Baths
      • 1,098 Sq Ft
      • Built 1983
      10 Ober Tal Dr Unit B32, Stratton, VT 05360

      Last Sold Summary

      • 1% Below List Price
      • $437/SF
      • 3 Days On Market
      • Last Sold Price $480,000
      • Nov 15, 2024

      Last Listing Agent Jamie Wylie Stratton Real Estate

  • /47

    $555,000 Under Contract

    • 3 Beds
    • 3 Baths
    • 2,341 Sq Ft

    49 High Point Dr Unit A122, Stratton, VT 05360

    Crown Point, Stratton Vermont. Enjoy this two-level, three bedroom, three bath condo and BONUS "4th" room with direct access to bath. This home has an upper and lower entry, both with plenty of storage for outdoor gear. The upper level opens into the kitchen, dining area, and living room with wood burning fireplace and a small deck. The primary ensuite bedroom, with a jacuzzi tub, is also on the

    Mike England Michael England Real Estate

    49 High Point Dr Unit A122, Stratton, VT 05360
  • /49

    $705,000 Sold Jan 06, 2026

    A6 Ridge Unit A6, Winhall, VT 05340

    • 4 Beds
    • 3 Baths
    • 2,118 Sq Ft
    • Built 1982

    Last Sold Summary

    • 12% Below List Price
    • $333/SF
    • 225 Days On Market

    Last Listing Agent Karin Hardy Berkshire Hathaway HomeServices Stratton Home

    A6 Ridge Unit A6, Winhall, VT 05340
    • /55

      Est $894,422 Not Listed For Sale

      45 Hilltop Rd, Winhall, VT 05340

      • 5 Beds
      • 4 Baths
      • 2,900 Sq Ft
      • Built 1996
      45 Hilltop Rd, Winhall, VT 05340

      Last Sold Summary

      • 1% Below List Price
      • $310/SF
      • 7 Days On Market
      • Last Sold Price $899,000
      • Jan 13, 2025

      Last Listing Agent Terry Hill Berkshire Hathaway HomeServices Stratton Home

  • /21

    $379,000

    • Land
    • 12.05 Acres
    • $31,452 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
  • /30

    $330,000 Sold May 09, 2025

    21 Stratton Ridge Rd, Winhall, VT 05340

    • 3 Beds
    • 1.5 Baths
    • 1,088 Sq Ft
    • Built 1970

    Last Sold Summary

    • 13% Below List Price
    • $303/SF
    • 115 Days On Market

    Last Listing Agent Andie Fusco Four Seasons Sotheby's Int'l Realty

    21 Stratton Ridge Rd, Winhall, VT 05340
    • /19

      Not Listed For Sale

      47 High Point Dr Unit B21, Stratton, VT 05360

      • 3 Beds
      • 3 Baths
      • 1,811 Sq Ft
      • Built 1986
      47 High Point Dr Unit B21, Stratton, VT 05360

      Last Sold Summary

      • $323/SF
      • 180 Days On Market
      • Last Sold Price $585,000
      • Apr 01, 2025

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

  • /24

    $225,000 Under Contract

    • 1 Bed
    • 1 Bath
    • 265 Sq Ft

    2053 Pikes Falls Rd, Jamaica, VT 05343

    A unique tiny house offering contemporary, Vermont farmhouse luxury in the Green Mountains. Featured on A & E's Living Smaller!This is tiny house vacation living at its finest. The house offers a full kitchen with four-burner gas stove and oven, farmhouse sink, butcher-block countertops, electric fireplace, AC, 40” Smart TV, Starlink WiFi, small soaking bathtub with shower. The bedroom loft

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    2053 Pikes Falls Rd, Jamaica, VT 05343
  • /15

    $159,500 Sold May 14, 2025

    000 Rose Ln, Londonderry, VT 05148

    • Land
    • 11.08 Acres
    • $14,395 per Acre

    Last Sold Summary

    • 47% Below List Price
    • 440 Days On Market

    Last Listing Agent Rachel Febbie EXP Realty

    000 Rose Ln, Londonderry, VT 05148
    • /25

      Not Listed For Sale

      761 Stratton Mountain Access Rd Unit 443 / 444, Stratton, VT 05360

      • 3 Beds
      • 2 Baths
      • 1,383 Sq Ft
      • Built 1998
      761 Stratton Mountain Access Rd Unit 443 / 444, Stratton, VT 05360

      Last Sold Summary

      • $602/SF
      • 43 Days On Market
      • Last Sold Price $832,000
      • Nov 22, 2024

      Last Listing Agent Andrew King Stratton Real Estate

  • /54

    $3,495,000

    • 6 Beds
    • 6.5 Baths
    • 5,660 Sq Ft

    168 Sunbowl Ridge Rd Unit 168 AB, Stratton, VT 05360

    Experience true mountain luxury in this stunning six bedroom six bathroom slope side single family home, perfectly positioned for effortless access to world-class skiing and snowboarding at the Stratton Mountain Resort. Designed with comfort and style in mind, this residence combines refined alpine architecture with modern amenities including a gym, steam shower, pool table that doubles as table

    Timothy Mich Doddridge Stratton Real Estate

    168 Sunbowl Ridge Rd Unit 168 AB, Stratton, VT 05360
  • /38

    $779,000 Sold Oct 31, 2025

    44 Hilltop Rd, Winhall, VT 05340

    • 4 Beds
    • 4 Baths
    • 2,997 Sq Ft
    • Built 1996

    Last Sold Summary

    • 1% Below List Price
    • $260/SF
    • 22 Days On Market

    Current Estimated Value $799,193

    Last Listing Agent Christiane Carroccio TPW Real Estate

    44 Hilltop Rd, Winhall, VT 05340
    • /27

      Not Listed For Sale

      19 Village Lodge Rd Unit 301, Stratton, VT 05155

      • 2 Beds
      • 2 Baths
      • 1,207 Sq Ft
      • Built 2004
      19 Village Lodge Rd Unit 301, Stratton, VT 05155

      Last Sold Summary

      • $571/SF
      • 9 Days On Market
      • Last Sold Price $689,000
      • Oct 10, 2024

      Last Listing Agent Jamie Wylie Stratton Real Estate

  • /13

    $135,000 Under Contract

    • Land
    • 1.36 Acres
    • $99,265 per Acre

    0 Stratton View Rd Unit 14, Winhall, VT 05340

    Stratton View Road lives up to its name. Big Views of Stratton, just 3 minutes to Stratton access road. Minutes to the snow making pond, great for walking and a dip in. the summer. There are 3 ski resorts with in 15 minutes as well as Manchester for shopping and dining. Own your piece of Vermont.

    Mike England Michael England Real Estate

    0 Stratton View Rd Unit 14, Winhall, VT 05340
  • /17

    $215,000 Sold Nov 21, 2025

    5997 Vt Route 30, Jamaica, VT 05343

    • 3 Beds
    • 2 Baths
    • 1,387 Sq Ft
    • Built 1999

    Last Sold Summary

    • 13% Above List Price
    • $155/SF
    • 0 Days On Market

    Current Estimated Value $362,201

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

    5997 Vt Route 30, Jamaica, VT 05343

Showing Results 201 - 240, Page 6 of 18

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