4,492

South Londonderry, VT Homes

Section Image
  • /32

    $449,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 1,460 Sq Ft

    32 Aspen Ln, Winhall, VT 05340

    A Sanctuary for Every Season:Picture the moment you turn off the main road and onto tree-lined Aspen Lane. The frantic pace of the week instantly drops away as you pull into your driveway. Tucked into a lush, wooded lot, this four-bedroom chalet is designed for those who live for the outdoors. Whether you’re here to chase the morning light on the slopes of nearby Stratton Resort or to spend a

    Robin Apps Four Seasons Sotheby's Int'l Realty

    32 Aspen Ln, Winhall, VT 05340
  • /10

    $345,000

    Sold Nov 06, 2025

    85 E Birch Rd Unit 15, Stratton, VT 05360

    • 2 Beds
    • 2 Baths
    • 1,119 Sq Ft
    • Built 1982

    Last Sold Summary

    • 4% Below List Price
    • $308/SF
    • 22 Days On Market

    Last Listing Agent Edwin Kevil Stratton Real Estate

    85 E Birch Rd Unit 15, Stratton, VT 05360
    • /40

      Est $811,428

      Not Listed For Sale

      40 Loop Rd, Winhall, VT 05340

      • 3 Beds
      • 3 Baths
      • 2,196 Sq Ft
      • Built 2006
      40 Loop Rd, Winhall, VT 05340

      Last Sold Summary

      • 5 Days On Market

  • /40

    $469,000

    $20K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,560 Sq Ft

    494 W River St, Londonderry, VT 05155

    This comfortable home is situated in a peaceful and open sunny meadow surrounded by mature trees and 10 acres of Vermont woods offering total privacy. A view of Magic Mountain is a bonus as is the close proximity to shopping and dining. An important feature of the home is the newly added Lochinvar high efficiency propane boiler with on demand hot water installed in November of 2025. The 4

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    494 W River St, Londonderry, VT 05155
  • /36

    $2,500,000

    Sold Mar 02, 2026

    771 Stratton Mtn Access Unit 452, Stratton, VT 05155

    • 5 Beds
    • 5.5 Baths
    • 4,098 Sq Ft
    • Built 1999

    Last Sold Summary

    • $610/SF
    • 0 Days On Market

    Last Listing Agent Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    771 Stratton Mtn Access Unit 452, Stratton, VT 05155
    • /40

      Est $1,694,198

      Not Listed For Sale

      541 Mtn Acres Rd, Jamaica, VT 05343

      • 6 Beds
      • 6.5 Baths
      • 7,426 Sq Ft
      • Built 2018
      541 Mtn Acres Rd, Jamaica, VT 05343

      Last Sold Summary

      • 346 Days On Market

  • /60

    $1,160,000

    • 5 Beds
    • 4 Baths
    • 3,664 Sq Ft

    82 N Brookwood Rd, Stratton, VT 05360

    Location , Location , Location! Situated on North Brookwood just below the covered brige you'll enjoy easy access to the Wanderer ski trail as well as the resort shuttle that picks you up at your driveway! This iconic resort property features a great room with custom wood barrel cathedral ceilings, a wall of glass, wood burning fireplace and wrap around deck. Designed for the mountain enthusiast,

    Kim Morgan-Wohler Wohler Realty Group

    82 N Brookwood Rd, Stratton, VT 05360
  • /30

    $717,500

    Sold Feb 13, 2026

    32 Cobble Ridge Rd Unit D10, Winhall, VT 05155

    • 3 Beds
    • 3 Baths
    • 2,317 Sq Ft
    • Built 1985

    Last Sold Summary

    • 2% Below List Price
    • $310/SF
    • 60 Days On Market

    Last Listing Agent Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

    32 Cobble Ridge Rd Unit D10, Winhall, VT 05155
    • /14

      Not Listed For Sale

      47 High Point Dr Unit B-15, Stratton, VT 05360

      • 2 Beds
      • 2 Baths
      • 1,207 Sq Ft
      • Built 1985
      47 High Point Dr Unit B-15, Stratton, VT 05360

      Last Sold Summary

      • 2 Days On Market

  • /47

    $1,450,000

    • 5 Beds
    • 4 Baths
    • 2,974 Sq Ft

    494-498 Goodaleville Rd, Jamaica, VT 05343

    OPEN HOUSE SATURDAY 8/1 FROM 3PM-5PM |10 MINUTES TO STRATTON RESORT | 4BR main house, 1BR barn apartment, and separate restored vintage barn | Just minutes from Stratton Mountain Resort, this beautifully restored Vermont farmhouse blends authentic character, exceptional craftsmanship, and modern comfort. Once the summer residence of renowned art historian Meyer Schapiro, the property retains the

    Cheyanne Pugliese

    494-498 Goodaleville Rd, Jamaica, VT 05343
  • /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 $1,979,716

      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

  • /32

    $1,275,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,814 Sq Ft

    19 Maple Hill Rd, Winhall, VT 05340

    Beautifully renovated in 2023, this 4-bedroom, 2-1/2 bathroom contemporary sits on 1.47 wooded acres with a sweeping circular driveway and genuine privacy — while still being on the Stratton shuttle route and just minutes from the base lodge on foot. The interior renovation was done right. Radiant heat floors run through the living room and kitchen, with two wood-burning fireplaces anchoring the

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    19 Maple Hill Rd, Winhall, VT 05340
  • /28

    $1,425,000

    Sold Jul 31, 2026

    43 Middle Ridge Rd Unit 415, Winhall, VT 05155

    • 4 Beds
    • 3.5 Baths
    • 2,363 Sq Ft
    • Built 2003

    Last Sold Summary

    • 16% Below List Price
    • $603/SF
    • 327 Days On Market

    Last Listing Agent Edwin Kevil Stratton Real Estate

    43 Middle Ridge Rd Unit 415, Winhall, VT 05155
    • /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

  • /17

    $729,000

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    778 Stratton Mountain Access Rd Unit 2103, Stratton, VT 05155

    Ski-In/Ski-Out Perfection: Your Premier Stratton Mountain Retreat! Experience the ultimate Vermont lifestyle in this rare 2-bedroom, 2-bathroom condo, perfectly positioned for true ski-in/ski-out convenience. Located just steps from the Villager Chairlift and the bustling heart of Stratton Village, this residence offers a seamless transition from the slopes to your front door.Designed with

    Robin Apps Four Seasons Sotheby's Int'l Realty

    778 Stratton Mountain Access Rd Unit 2103, Stratton, VT 05155
  • /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 $1,038,382

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    19 Roundtree Rd, Bondville, VT 05340
    • /40

      Est $1,683,608

      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

  • /9

    $374,900

    • Land
    • 2.31 Acres
    • $162,294 per Acre

    0 Wall St, Winhall, VT 05340

    Offered as a set, this property presents a rare opportunity to own two separately deeded parcels in a location that is only minutes from Stratton Mountain yet worlds away from the bustle of the resort. Totaling 2.31 acres, this land is situated high on River Road where neighboring homes enjoy spectacular views of Stratton. Conceptual rendering showing the potential view is based on the current

    Cheyanne Pugliese

    0 Wall St, Winhall, VT 05340
  • /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 $717,722

    Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    86 Benson Fuller Dr, Bondville, VT 05340
    • /24

      Est $512,149

      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

  • /38

    $795,000

    • 4 Beds
    • 3.5 Baths
    • 4,104 Sq Ft

    25 Benson Fuller Dr, Bondville, VT 05340

    Where Mountains Meet Modern Living: Perched just moments from the energy of Stratton Mountain Resort, this contemporary mountain home reimagines what a Vermont getaway feels like. From the moment you step inside, the design does exactly what a great contemporary home should: it steps back and lets nature take center stage. Massive, soaring windows act as living art pieces, framing sweeping,

    Robin Apps Four Seasons Sotheby's Int'l Realty

    25 Benson Fuller Dr, Bondville, 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 $516,522

    Last Listing Agent Annette Gallo Real Broker LLC

    374 Winhall Hollow Rd, 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

  • /46

    $1,599,000

    • 6 Beds
    • 5.5 Baths
    • 5,568 Sq Ft

    144 High Meadow Rd, Winhall, VT 05340

    Expansive Stratton Mountain Resort Residence with exceptional floor plan and renovation! Featuring an upscale redesign of two top floor primary suite bathrooms, updated kitchen and expanded finished lower level, this home is ready for mountain living and endless entertaining! Designed with multiple gathering rooms and fireplaces, you'll enjoy apres ski with and an incredible open floor plan. Game

    Kim Morgan-Wohler Wohler Realty Group

    144 High Meadow Rd, Winhall, VT 05340
  • /59

    $949,000

    Sold Jul 10, 2026

    178 High Meadow Rd, Winhall, VT 05340

    • 5 Beds
    • 3.5 Baths
    • 4,000 Sq Ft
    • Built 1987

    Last Sold Summary

    • 6% Above List Price
    • $237/SF
    • 6 Days On Market

    Current Estimated Value $922,398

    Last Listing Agent Terry Hill Berkshire Hathaway HomeServices Stratton Home

    178 High Meadow Rd, Winhall, VT 05340
    • /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

  • /40

    $1,500,000

    • 7 Beds
    • 7.5 Baths
    • 8,364 Sq Ft

    251 Pratt Bridge Rd, Jamaica, VT 05343

    Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas & the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated B&B. Prepare to be Enchanted! An

    TG Glazer Winhall Real Estate

    251 Pratt Bridge Rd, Jamaica, VT 05343
  • /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 $452,246

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

    163 Vt Route 30, Winhall, VT 05340
    • /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

  • /18

    $409,000

    Under Contract
    • 1 Bed
    • 1 Bath
    • 675 Sq Ft

    771 Stratton Mountain Access Rd Unit 468, Stratton, VT 05360

    Perfectly positioned in the heart of Stratton Mountain Resort, this well-maintained fourth-floor Long Trail condominium offers the mountain lifestyle you are looking for. Enjoy partial views of the mountain from your retreat while being just a short walk to Stratton's ski slopes, Village shops, restaurants, year-round events, and outdoor activities. Whether you're heading out for first tracks,

    Carrie Mathews Winhall Real Estate

    771 Stratton Mountain Access Rd Unit 468, Stratton, VT 05360
  • /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
    • /23

      Not Listed For Sale

      133 Quarter Mile Rd Unit Black Bear, Stratton, VT 05340

      • 3 Beds
      • 2 Baths
      • 1,300 Sq Ft
      • Built 1968
      133 Quarter Mile Rd Unit Black Bear, Stratton, VT 05340

      Last Sold Summary

      • 6 Days On Market

  • /15

    $415,000

    • 1 Bed
    • 1 Bath
    • 560 Sq Ft

    761 Stratton Mountain Access Rd Unit 333, Stratton, VT 05360

    Enjoy the convenience of mountain living from this well-positioned residence in Long Trail House. Overlooking the peaceful Commons Pond, this home offers a relaxing setting while placing you directly across the street from Stratton Village and the ski slopes.The functional floor plan provides comfortable living with easy access to outdoor space, making it simple to enjoy every season. Whether

    Jamie Wylie Stratton Real Estate

    761 Stratton Mountain Access Rd Unit 333, Stratton, VT 05360
  • /21

    $250,000

    Sold Jun 15, 2026

    771 Stratton Mountain Access Rd Unit 358, Stratton, VT 05360

    • 1 Bed
    • 1 Bath
    • 522 Sq Ft
    • Built 2001

    Last Sold Summary

    • 14% Above List Price
    • $479/SF
    • 3 Days On Market

    Last Listing Agent Andrew King Stratton Real Estate

    771 Stratton Mountain Access Rd Unit 358, Stratton, VT 05360
    • /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

  • /38

    $775,000

    • 4 Beds
    • 4 Baths
    • 3,520 Sq Ft

    12 Stratton Ridge Rd, Winhall, VT 05340

    First time on the market, this spacious mountain home has been lovingly maintained by one family since it was built in 1980. Tucked away on a generous double lot at the dead end of a private road, the setting offers privacy along with a true Vermont feel—quiet and peaceful.Inside, the home features a bright, open layout with abundant natural light and warm woodwork throughout, creating an

    Carrie Mathews Winhall Real Estate

    12 Stratton Ridge Rd, Winhall, VT 05340
  • /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 $508,196

    Last Listing Agent Carrie Mathews Winhall Real Estate

    176 Pratt Bridge Rd, Jamaica, VT 05343
    • /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

  • /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

Showing Results 161 - 200, Page 5 of 18

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