4,472

South Londonderry, VT Homes

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  • /51

    $1,125,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 2,588 Sq Ft

    3635 Under the Mountain Rd, Londonderry, VT 05148

    Set on 65 private acres along Vermont’s iconic Under the Mountain Road, this custom-designed modern retreat offers privacy, sweeping mountain views, and refined simplicity. Built in 2019, the 4-bedroom, 4-bath home was thoughtfully sited to blend seamlessly into its natural surroundings while maximizing light and year-round vistas. Wrapped in natural cedar siding with a metal roof, the home’s

    Christiane Carroccio TPW Real Estate

    3635 Under the Mountain Rd, Londonderry, VT 05148
  • /43

    $887,000 Sold Oct 17, 2025

    460 Stratton Gate Rd, Jamaica, VT 05343

    • 4 Beds
    • 3 Baths
    • 3,155 Sq Ft
    • Built 1992

    Last Sold Summary

    • 1% Below List Price
    • $281/SF
    • 12 Days On Market

    Current Estimated Value $975,095

    Last Listing Agent Helen Nault

    460 Stratton Gate Rd, Jamaica, VT 05343
    • /40

      Est $552,977 Not Listed For Sale

      482 Pratt Bridge Rd, Jamaica, VT 05343

      • 3 Beds
      • 2 Baths
      • 1,506 Sq Ft
      • Built 1988
      482 Pratt Bridge Rd, Jamaica, VT 05343

      Last Sold Summary

      • 2% Above List Price
      • $359/SF
      • 44 Days On Market

      Last Sold Price $540,000

      Last Listing Agent Chad Lackey Deerfield Valley Real Estate

  • /55

    $995,000

    • 5 Beds
    • 4.5 Baths
    • 2,321 Sq Ft

    24 N Branch Rd, Winhall, VT 05340

    Exceptional Renovation of a Stratton Resort Residence in the Stratton Quarter Mile neighborhood on Shuttle, just a short walk home from the Village. 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- this mountain chalet has been updated

    Kim Morgan-Wohler Wohler Realty Group

    24 N Branch Rd, Winhall, VT 05340
  • /27

    $245,000 Sold Nov 14, 2025

    8365 Vermont 30, Jamaica, VT 05343

    • 2 Beds
    • 1 Bath
    • 756 Sq Ft
    • Built 1967

    Last Sold Summary

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

    Last Listing Agent TG Glazer Winhall Real Estate

    8365 Vermont 30, Jamaica, VT 05343
    • /31

      Est $608,300 Not Listed For Sale

      81 Edie Ln, Jamaica, VT 05343

      • 3 Beds
      • 3 Baths
      • 2,593 Sq Ft
      • Built 1987
      81 Edie Ln, Jamaica, VT 05343

      Last Sold Summary

      • 14% Above List Price
      • $206/SF
      • 56 Days On Market

      Last Sold Price $535,000

      Last Listing Agent Trent Stephens Wohler Realty Group

  • /50

    $929,000 Open Sun 12PM - 2PM

    • 4 Beds
    • 3 Baths
    • 2,068 Sq Ft

    104 High Meadow Rd, Winhall, VT 05340

    Location says it all. This High Meadow mountain retreat is located in one of Stratton Resort’s premier locations. High Meadow offers winter weekend and holiday shuttle service to the slopes for your convenience. Bathed in sunshine thanks to its southern exposure, this contemporary home welcomes you with a seamless open floor plan that flows effortlessly from the kitchen into expansive

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    104 High Meadow Rd, Winhall, VT 05340
  • /25

    $360,000 Sold Feb 25, 2026

    00 Ross Rd, Winhall, VT 05340

    • Land
    • 41.1 Acres
    • $8,759 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 82 Days On Market

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

    00 Ross Rd, Winhall, VT 05340
    • /25

      Est $753,845 Not Listed For Sale

      110 Upper Taylor Hill Rd, Jamaica, VT 05343

      • 5 Beds
      • 3 Baths
      • 1,600 Sq Ft
      • Built 1968
      110 Upper Taylor Hill Rd, Jamaica, VT 05343

      Last Sold Summary

      • 6% Above List Price
      • $445/SF
      • 15 Days On Market

      Last Sold Price $711,500

      Last Listing Agent Helen Nault

  • /37

    $999,000

    • 4 Beds
    • 3.5 Baths
    • 2,280 Sq Ft

    17 Roundtree Rd, Winhall, VT 05340

    Contemporary ski chalet on shuttle route located on a short cul-de-sac in the coveted North Brookwood neighborhood, a stone's throw from the Stratton base lodge. This 4 bedroom, 3 1⁄2 bath home boasts an open plan, walls of windows, and floor-to-ceiling stone fireplace in the Great Room. The pass-through kitchen was fully renovated in 2021 in addition to many other upgrades. Test your skills at

    Sarah Nichols Winhall Real Estate

    17 Roundtree Rd, Winhall, VT 05340
  • /30

    $510,000 Sold Jun 05, 2025

    5600 Pikes Falls Rd, Jamaica, VT 05343

    • 3 Beds
    • 2 Baths
    • 1,459 Sq Ft
    • Built 1977

    Last Sold Summary

    • 24% Below List Price
    • $350/SF
    • 170 Days On Market

    Current Estimated Value $637,305

    Last Listing Agent Jamie Wylie Stratton Real Estate

    5600 Pikes Falls Rd, Jamaica, VT 05343
    • /35

      Not Listed For Sale

      15 Stratton View Rd, Bondville, VT 05340

      • 4 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1964
      15 Stratton View Rd, Bondville, VT 05340

      Last Sold Summary

      • 5% Below List Price
      • $250/SF
      • 1 Day On Market

      Last Sold Price $420,000

      Last Listing Agent Rachel Febbie EXP Realty

  • /14

    $649,000

    • 2 Beds
    • 2 Baths
    • 1,148 Sq Ft

    792 Stratton Mtn Access Rd Unit 4310, Stratton, VT 05155

    Maximize your time on the snow in this coveted two-bedroom village watch condo. Featuring a spacious, open layout, the interior boasts a classic wood-burning fireplace and a full kitchen perfect for entertaining. Forget the shuttle; enjoy the seamless convenience of a private ski locker and immediate access to both the lifts and the vibrant resort village. A perfect blend of convenience,

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    792 Stratton Mtn Access Rd Unit 4310, Stratton, VT 05155
  • /4

    $232,500 Sold Sep 18, 2025

    0 Gold Medal Cir Unit 5023219, Stratton, VT 05155

    • Land
    • 1.57 Acres
    • $148,089 per Acre

    Last Sold Summary

    • 7% Below List Price
    • 238 Days On Market

    Last Listing Agent Ross Powers TPW Real Estate

    0 Gold Medal Cir Unit 5023219, Stratton, VT 05155
    • /40

      Est $748,314 Not Listed For Sale

      954 South Rd, Peru, VT 05152

      • 5 Beds
      • 3 Baths
      • 2,327 Sq Ft
      • Built 1979
      954 South Rd, Peru, VT 05152

      Last Sold Summary

      • 1% Above List Price
      • $318/SF
      • 284 Days On Market

      Last Sold Price $739,500

      Last Listing Agent Chuck Sweetman Mary Mitchell Miller Real Estate

  • /24

    $849,000

    • 4 Beds
    • 2 Baths
    • 1,638 Sq Ft

    12 Ober Tal Dr Unit C/23C/24, Stratton, VT 05360

    Unmatched Comfort and Convenience at Stratton's Ober Tal – Walk to LiftDiscover the ideal ski retreat in this bright, spacious, one-of-a-kind double unit at Ober Tal, Building C. Just a short walk to the Tamarack ski lift, you’ll enjoy unbeatable access to the slopes and all the amenities in Stratton Village.Close enough to swing back for a quick lunch, this condo lets you make

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    12 Ober Tal Dr Unit C/23C/24, Stratton, VT 05360
  • /41

    $785,000 Sold Nov 21, 2025

    202 Pratt Bridge Rd, Jamaica, VT 05343

    • 3 Beds
    • 2.5 Baths
    • 2,800 Sq Ft
    • Built 1966

    Last Sold Summary

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

    Current Estimated Value $752,095

    Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

    202 Pratt Bridge Rd, Jamaica, VT 05343
    • /13

      Not Listed For Sale

      234 Mountain Rd, Stratton, VT 05155

      234 Mountain Rd, Stratton, VT 05155

      Last Sold Summary

      • 501 Days On Market

      Last Sold Price $620,000

      Last Listing Agent Jamie Wylie Stratton Real Estate

  • /26

    $325,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 976 Sq Ft

    9047 Vermont 30, Jamaica, VT 05155

    “The Yellow Sweetie” offers a rare blend of charm, convenience, and proven income potential. This stylish country-meets-shabby-chic retreat has been a high-income producing rental for many years, making it an excellent opportunity for investment, year-round living, or a Vermont vacation retreat.Ideally located near the base of Stratton Mountain, the property sits just one minute from the

    Carrie Mathews Winhall Real Estate

    9047 Vermont 30, Jamaica, VT 05155
  • /41

    $1,150,000 Sold Jul 25, 2025

    35 Old Ridge Rd, Winhall, VT 05155

    • 4 Beds
    • 5.5 Baths
    • 4,826 Sq Ft
    • Built 1997

    Last Sold Summary

    • 38% Below List Price
    • $238/SF
    • 369 Days On Market

    Last Listing Agent Mike England Michael England Real Estate

    35 Old Ridge Rd, Winhall, VT 05155
    • /21

      Est $245,773 Not Listed For Sale

      1406 Cole Pond Rd, Jamaica, VT 05343

      • 1 Bed
      • 1 Bath
      • 320 Sq Ft
      • Built 2015
      1406 Cole Pond Rd, Jamaica, VT 05343

      Last Sold Summary

      • 14% Below List Price
      • $891/SF
      • 15 Days On Market

      Last Sold Price $285,000

      Last Listing Agent Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  • /31

    $1,750,000

    • 4 Beds
    • 3.5 Baths
    • 2,698 Sq Ft

    148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360

    148B Sun Bowl Ridge Rd., Stratton Mountain, VT 05155, Solstice 148B Ski in, ski out directly from your private garage on a Stratton ski trail that has full snowmaking coverage. This home is in one of the most exclusive trailside communities in all of the Northeast! It has an open and sunny floorplan with large windows and a sliding glass door to the private patio with fire pit and hot tub.

    Andrew King Stratton Real Estate

    148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360
  • /43

    $755,000 Sold Nov 14, 2025

    43 Hilltop Rd, Winhall, VT 05340

    • 4 Beds
    • 4 Baths
    • 3,020 Sq Ft
    • Built 1988

    Last Sold Summary

    • 2% Above List Price
    • $250/SF
    • 0 Days On Market

    Current Estimated Value $752,401

    Last Listing Agent Daniel Preston KW Vermont Woodstock

    43 Hilltop Rd, Winhall, VT 05340
    • /24

      Est $417,423 Not Listed For Sale

      292 Tallwood Cir, Londonderry, VT 05148

      • 4 Beds
      • 3 Baths
      • 1,558 Sq Ft
      • Built 1970
      292 Tallwood Cir, Londonderry, VT 05148

      Last Sold Summary

      • 11% Above List Price
      • $241/SF
      • 4 Days On Market

      Last Sold Price $375,000

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

  • /39

    $735,000 Under Contract

    • 4 Beds
    • 3 Baths
    • 2,091 Sq Ft

    5 Wall St, Bondville, VT 05340

    While temperatures outside may be freezing, step inside and take in the incredible views of Stratton while basking in sunlight from the living room of this Vermont home. Located just one mile from the base of the Stratton Access Road and only 20 minutes from Manchester, the setting offers exceptional convenience while remaining peacefully tucked away in the private woods of Winhall. The main

    Cheyanne Pugliese

    5 Wall St, Bondville, VT 05340
  • /59

    $1,082,500 Sold Aug 29, 2025

    4 Garden Loop Rd, Winhall, VT 05340

    • 3 Beds
    • 3.5 Baths
    • 4,054 Sq Ft
    • Built 2005

    Last Sold Summary

    • 10% Below List Price
    • $267/SF
    • 45 Days On Market

    Current Estimated Value $1,110,307

    Last Listing Agent Lucy Ferrada Heney Realtors - Element Real Estate (Montpelier)

    4 Garden Loop Rd, Winhall, VT 05340
    • /37

      Est $305,453 Not Listed For Sale

      176 Melendy Hill Rd, South Londonderry, VT 05155

      • 5 Beds
      • 3 Baths
      • 2,000 Sq Ft
      • Built 1900
      176 Melendy Hill Rd, South Londonderry, VT 05155

      Last Sold Summary

      • 5% Above List Price
      • $145/SF
      • 24 Days On Market

      Last Sold Price $290,000

      Last Listing Agent Rachel Febbie EXP Realty

  • /51

    $585,000

    • 3 Beds
    • 2 Baths
    • 1,814 Sq Ft

    1886 Winhall Hollow Rd, South Londonderry, VT 05155

    Exceptional property tucked amidst nature with views toward Magic. Whether you're a weekend warrior looking to enjoy everything the Green Mountains have to offer or looking for a year round residence with great schools, this property offers an optimal location- convenient to Stratton, Bromley and Magic Mountains as well as Burr and Burton Academy and Floodbrook School. Gourmet kitchen with gas

    Kim Morgan-Wohler Wohler Realty Group

    1886 Winhall Hollow Rd, South Londonderry, VT 05155
  • /28

    $518,000 Sold Sep 19, 2025

    8 Ober Tal Unit A-32, Stratton, VT 05155

    • 2 Beds
    • 2 Baths
    • 1,096 Sq Ft
    • Built 1983

    Last Sold Summary

    • 1% Below List Price
    • $473/SF
    • 40 Days On Market

    Last Listing Agent Cheyanne Pugliese

    8 Ober Tal Unit A-32, Stratton, VT 05155
    • /34

      Not Listed For Sale

      291 Pikes Falls Rd, Stratton, VT 05360

      • 6 Beds
      • 3 Baths
      • 2,400 Sq Ft
      • Built 1964
      291 Pikes Falls Rd, Stratton, VT 05360

      Last Sold Summary

      • $390/SF
      • 33 Days On Market

      Last Sold Price $935,000

      Last Listing Agent Christiane Carroccio TPW Real Estate

  • /59

    $2,800,000

    • 3 Beds
    • 3.5 Baths
    • 3,938 Sq Ft

    23 Valley View Rd, Winhall, VT 05340

    Set at the end of a long, private driveway, this remarkable property unveils dramatic panoramic vistas that stretch nearly 40 miles. Offering a rare sense of seclusion & grandeur, the home is an ideal retreat where nature, privacy, and beauty converge.Designed w/a modern aesthetic,an expansive open-concept layout, the main floor features a stunning stone fireplace , enhanced by soaring ceilings

    Kim Morgan-Wohler Wohler Realty Group

    23 Valley View Rd, Winhall, VT 05340
  • /4

    $170,000 Sold Nov 07, 2025

    440 Edie Ln, Jamaica, VT 05343

    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft
    • Built 1971

    Last Sold Summary

    • 19% Below List Price
    • $81/SF
    • 16 Days On Market

    Current Estimated Value $241,932

    Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

    440 Edie Ln, Jamaica, VT 05343
    • /28

      Not Listed For Sale

      43 Middle Ridge Rd Unit 312, Winhall, VT 05155

      • 2 Beds
      • 2 Baths
      • 1,014 Sq Ft
      • Built 2004
      43 Middle Ridge Rd Unit 312, Winhall, VT 05155

      Last Sold Summary

      • $626/SF
      • 46 Days On Market

      Last Sold Price $635,000

      Last Listing Agent Mike England Michael England Real Estate

  • /31

    $435,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,814 Sq Ft

    132 Pratt Bridge Rd, Jamaica, VT 05343

    Welcome to this charming Vermont getaway, custom - built and lovingly maintained by the original owners. Ideally located just minutes from Stratton Mountain and within easy reach of Bromley and Magic for a full season of winter adventure. In the warmer months, enjoy nearby lakes perfect for swimming, paddling, or simply relaxing by the water.Inside, the home offers 3 bedrooms and 2 full

    Lisa Sullivan Four Seasons Sotheby's Int'l Realty

    132 Pratt Bridge Rd, Jamaica, VT 05343
  • /33

    $740,000 Sold Jan 02, 2026

    G12 Cobble Ridge Rd, Winhall, VT 05340

    • 4 Beds
    • 4 Baths
    • 2,764 Sq Ft
    • Built 1985

    Last Sold Summary

    • 5% Below List Price
    • $268/SF
    • 1 Day On Market

    Current Estimated Value $728,333

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

    G12 Cobble Ridge Rd, Winhall, VT 05340
    • /40

      Est $2,305,515 Not Listed For Sale

      95 Winhall Hollow Rd, Bondville, VT 05340

      • 7 Beds
      • 9.5 Baths
      • 5,641 Sq Ft
      • Built 2001
      95 Winhall Hollow Rd, Bondville, VT 05340

      Last Sold Summary

      • 2% Above List Price
      • $399/SF
      • 18 Days On Market

      Last Sold Price $2,250,000

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

  • /51

    $439,000 Under Contract

    • 5 Beds
    • 2 Baths
    • 1,888 Sq Ft

    12 Stratton West Rd Unit 12, Winhall, VT 05340

    This 5 bedroom, 2 full bath townhouse is the perfect getaway for ski enthusiasts and nature lovers alike. It is conveniently located just minutes to Stratton Mountain Resort. You'll enjoy year-round access to skiing, hiking, paddling, golfing, and many additional Southern Vermont area amenities. Enjoy three floors of spacious living. Enter through the large mudroom with exceptional storage for

    Robert Sabol Wohler Realty Group

    12 Stratton West Rd Unit 12, Winhall, VT 05340
  • /20

    $590,000 Sold Nov 19, 2025

    771 Stratton Mountain Access Rd Unit 361, Stratton, VT 05360

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

    Last Sold Summary

    • $641/SF
    • 59 Days On Market

    Last Listing Agent Christiane Carroccio TPW Real Estate

    771 Stratton Mountain Access Rd Unit 361, Stratton, VT 05360
    • /30

      Not Listed For Sale

      13 Stratton Rd W Unit 13, Winhall, VT 05340

      • 5 Beds
      • 3 Baths
      • 1,785 Sq Ft
      • Built 1970
      13 Stratton Rd W Unit 13, Winhall, VT 05340

      Last Sold Summary

      • $202/SF
      • 4 Days On Market

      Last Sold Price $360,000

      Last Listing Agent Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

  • /56

    $2,999,000 Under Contract

    • 6 Beds
    • 6.5 Baths
    • 6,650 Sq Ft

    25 Mountain Haunts Rd, Winhall, VT 05340

    Exceptional 40.8 acre newly expanded and renovated Stratton Mountain estate with unrivaled views of Stratton just minutes from the Base Lodge or Sun Bowl. This is your own personal winter playground where you can hit the slopes or snowmobile and hike on your own land with additional acreage available.This Grand Lodge NOW BOASTS 4 ensuite bedroom, 3 stone fireplaces, huge lodge room w/ large beams

    Kim Morgan-Wohler Wohler Realty Group

    25 Mountain Haunts Rd, Winhall, VT 05340

Showing Results 81 - 120, Page 3 of 18

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