4,475

South Londonderry, VT Homes

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  • /2

    $210,000 Sold Aug 29, 2025

    0 Gold Medal Cir Unit 5027515, Stratton, VT 05155

    • Land
    • 2.1 Acres
    • $100,000 per Acre

    Last Sold Summary

    • 16% Below List Price
    • 190 Days On Market

    Last Listing Agent Ross Powers TPW Real Estate

    0 Gold Medal Cir Unit 5027515, Stratton, VT 05155
    • /40

      Est $543,433 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

      • 1% Above List Price
      • $359/SF
      • 44 Days On Market
      • Last Sold Price $540,000
      • Jan 11, 2024

      Last Listing Agent Chad Lackey Deerfield Valley Real Estate

  • /37

    $975,000 Under Contract

    • 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
  • /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 $868,204

    Last Listing Agent Helen Nault

    460 Stratton Gate Rd, Jamaica, VT 05343
    • /31

      Est $608,033 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
      • Aug 31, 2023

      Last Listing Agent Trent Stephens Wohler Realty Group

  • /60

    $979,000

    • 4 Beds
    • 3.5 Baths
    • 5,248 Sq Ft

    41-43 Cranberry Hill Rd, Winhall, VT 05340

    This is the ultimate modern Alpine chalet, fully renovated yet boasting the classic flat-sawn balusters characteristic of mountain homes in the Alps. Three expansive floors offer sunny, well-appointed space, beginning with a roomy mudroom, three bedrooms and two bathrooms (one en-suite). Head upstairs to join your friends and family in the open-concept European kitchen/living/dining room with

    Jamie Luke TPW Real Estate

    41-43 Cranberry Hill Rd, Winhall, VT 05340
  • /27

    $245,000 Sold Nov 14, 2025

    8365 Vt Route 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

    Current Estimated Value $241,876

    Last Listing Agent TG Glazer Winhall Real Estate

    8365 Vt Route 30, Jamaica, VT 05343
    • /25

      Est $752,750 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
      • Apr 15, 2024

      Last Listing Agent Helen Nault

  • /13

    $875,000

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

    43 Middle Ridge Rd Unit 209, Winhall, VT 05155

    Beautiful corner three bedroom, two bath condominium in one Stratton Mountain's most desirable neighborhoods. Heated parking garage, with two assigned spaces. Locker room for ski storage. Heated year round pool, hot tubs, sauna for Rising Bear and Hearthstone. Private shuttle to skier drop off area, or walk directly across street. Excellent potential as a rental property. Sold fully furnished.

    John Sikes Stratton Real Estate

    43 Middle Ridge Rd Unit 209, Winhall, VT 05155
  • /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
    • /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
      • Jun 16, 2023

      Last Listing Agent Rachel Febbie EXP Realty

  • /52

    $1,100,000 Under Contract

    • 3 Beds
    • 4.5 Baths
    • 4,279 Sq Ft

    3 Linscott Rd, Winhall, VT 05340

    Welcome home! This property is MOVE IN READY ! This exceptional contemporary is just minutes from the Stratton base lodge. Meticulously maintained and thoughtfully updated, this home is ideal for you and your guests! Designed for both relaxation and entertaining, the open-concept floor plan ensures everyone can gather with ease. Two spacious living areas provide wonderful flexibility for

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    3 Linscott 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 $663,071

    Last Listing Agent Jamie Wylie Stratton Real Estate

    5600 Pikes Falls Rd, Jamaica, VT 05343
    • /40

      Est $780,975 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

      • 6% Above List Price
      • $318/SF
      • 284 Days On Market
      • Last Sold Price $739,500
      • May 26, 2023

      Last Listing Agent Chuck Sweetman Mary Mitchell Miller Real Estate

  • /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
  • /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
    • /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
      • Jun 10, 2024

      Last Listing Agent Jamie Wylie Stratton Real Estate

  • /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
  • /30

    $1,550,000 Sold Apr 10, 2026

    147 High Meadow Rd, Winhall, VT 05340

    • 5 Beds
    • 5 Baths
    • 4,000 Sq Ft
    • Built 1984

    Last Sold Summary

    • 4% Above List Price
    • $388/SF
    • 9 Days On Market

    Current Estimated Value $1,149,442

    Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

    147 High Meadow Rd, Winhall, VT 05340
    • /21

      Est $241,667 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

      • 15% Below List Price
      • $891/SF
      • 15 Days On Market
      • Last Sold Price $285,000
      • Apr 25, 2023

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

  • /51

    $550,000

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

    1886 Winhall Hollow Rd, South Londonderry, VT 05155

    Optimal Location, Competitively priced, Exceptional property tucked amidst nature with views toward Magic. Offering Main Residence and a large oversized detached garage/ barn with upstairs finished space and plenty of space for snow mobiles, ATVs and all your mountain vehicles and outdoor toys. Whether you're a weekend warrior looking to enjoy everything the Green Mountains have to offer or

    Kim Morgan-Wohler Wohler Realty Group

    1886 Winhall Hollow Rd, South Londonderry, VT 05155
  • /33

    $485,000 Sold Apr 20, 2026

    3 Strattonwald Rd, Winhall, VT 05340

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft
    • Built 1963

    Last Sold Summary

    • 8% Below List Price
    • $361/SF
    • 276 Days On Market

    Current Estimated Value $491,724

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

    3 Strattonwald Rd, Winhall, VT 05340
    • /37

      Est $302,395 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

      • 4% Above List Price
      • $145/SF
      • 24 Days On Market
      • Last Sold Price $290,000
      • Dec 07, 2023

      Last Listing Agent Rachel Febbie EXP Realty

  • /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
  • /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 $752,308

    Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

    202 Pratt Bridge Rd, Jamaica, VT 05343
    • /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
      • May 30, 2024

      Last Listing Agent Christiane Carroccio TPW Real Estate

  • /59

    $1,300,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,900 Sq Ft

    51 Village Square, Stratton, VT 05360

    Experience this Extraordinary Location in the heart of the Stratton Resort Village from this RENOVATED and EXPANDED Village Square 4 bedroom unit where you can walk to everything and be on the lifts in just a few minutes. Nothing compares to trailside living in the VILLAGE where convenience abounds and you won't touch your car until it's time to hit the highway. Ski home for lunch and you'll have

    Kim Morgan-Wohler Wohler Realty Group

    51 Village Square, Stratton, VT 05360
  • /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
    • /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
      • Jul 31, 2024

      Last Listing Agent Mike England Michael England Real Estate

  • /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
  • /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 $770,723

    Last Listing Agent Daniel Preston KW Vermont Woodstock

    43 Hilltop Rd, Winhall, VT 05340
    • /40

      Est $2,349,437 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

      • 4% Above List Price
      • $399/SF
      • 18 Days On Market
      • Last Sold Price $2,250,000
      • Nov 03, 2023

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

  • /27

    $379,000

    • 4 Beds
    • 3 Baths
    • 1,720 Sq Ft

    292 Tallwood Cir, Londonderry, VT 05148

    Welcome to this charming chalet in the Sherwood Forest neighborhood of Londonderry! Come inside to a bright, open great room featuring living and dining areas, large windows, a cozy wood stove, and a breakfast bar that connects seamlessly to the kitchen. This inviting home is the perfect Vermont getaway for you or your guests. Just off the great room, the classic country kitchen offers an ideal

    The Malley Group KW Vermont

    292 Tallwood Cir, Londonderry, VT 05148
  • /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 $1,103,341

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

    4 Garden Loop Rd, Winhall, VT 05340
    • /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
      • Oct 03, 2023

      Last Listing Agent Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

  • /11

    $2,425,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 4,536 Sq Ft

    6 Stone Lodge Rd, Winhall, VT 05340

    SHOWINGS BEGIN at Thursday February 12. Premier New Construction, offering 4500+ SF of luxury living on three levels, perched on 2.5 acres to maximize panoramic mountain and Bromley views. Just minutes to the Stratton Resort Base Lodge, this exceptional 4 bedroom/3.5 bath floor plan combines contemporary design, craftsmanship of the highest caliber and energy efficiency.Thoughtfully designed for

    Kim Morgan-Wohler Wohler Realty Group

    6 Stone Lodge Rd, Winhall, VT 05340
  • /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
    • /29

      Est $700,579 Not Listed For Sale

      32 Beaver St, Bondville, VT 05340

      • 4 Beds
      • 2.5 Baths
      • 2,179 Sq Ft
      • Built 2008
      32 Beaver St, Bondville, VT 05340

      Last Sold Summary

      • 5% Above List Price
      • $307/SF
      • 7 Days On Market
      • Last Sold Price $668,000
      • Oct 04, 2024

      Last Listing Agent Jamie Wylie Stratton Real Estate

  • /54

    $2,050,000 Under Contract

    • 4 Beds
    • 4.5 Baths
    • 2,486 Sq Ft

    97 N Brookwood Rd, Stratton, VT 05360

    Welcome to your mountain chalet! 97 North Brookwood Road, one of the top most desirable locations on Stratton Mountain. Fully renovated and updated home, one of the eight original Austrian chalets on the mountain. Direct walk in and ski out to the Lower Wanderer trail. 4 bedroom in total with 3 en-suite bathrooms and 1 custom double bunk room with attached bathroom. Gorgeous great room with stone

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    97 N Brookwood Rd, Stratton, VT 05360
  • /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 $199,046

    Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

    440 Edie Ln, Jamaica, VT 05343

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