4,489

South Londonderry, VT Homes

Section Image
    • /59

      Est $5,034,822

      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

      • 93 Days On Market

  • /41

    $1,498,500

    $252K PRICE DROP
    • 7 Beds
    • 5 Baths
    • 4,649 Sq Ft

    4669 Vermont Route 100, Londonderry, VT 05148

    Encompassing over 200 acres of pasture and forest, Timberland Farm is anchored by an early 1800s farmhouse that feels at once timeless and lived-in, a place shaped by centuries of stories, music, and shared meals. The living spaces feel both intimate and generous, framed by hand-hewn beams and original wide pine floors. From the dining room to the music room, wood-burning fireplaces crowned with

    Story Jenks LandVest, Inc/Woodstock

    4669 Vermont Route 100, Londonderry, VT 05148
  • /33

    $895,000

    Sold May 19, 2026

    3 Stratton Springs Rd Unit 3B, Stratton, VT 05360

    • 3 Beds
    • 2.5 Baths
    • 1,770 Sq Ft
    • Built 1999

    Last Sold Summary

    • 2% Above List Price
    • $506/SF
    • 2 Days On Market

    Last Listing Agent Andrew King Stratton Real Estate

    3 Stratton Springs Rd Unit 3B, Stratton, 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

      • 8 Days On Market

  • /27

    $609,000

    • 4 Beds
    • 3 Baths
    • 1,650 Sq Ft

    60 Hilltop Rd Unit 60, Winhall, VT 05340

    Turn-key Stratton retreat in one of the area’s most desirable year-round communities. This 4-bedroom, 3-bath Intervale townhome offers the perfect blend of comfort and convenience—just minutes to the slopes with seasonal shuttle service right from the community. The open-concept living area is ideal for gathering after a day on the mountain, while five mini-split systems provide efficient heating

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    60 Hilltop Rd Unit 60, 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 $400,109

    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

      • 7 Days On Market

  • /14

    $450,000

    $50K PRICE DROP
    • Land
    • 21.2 Acres
    • $21,226 per Acre

    56 Lower Taylor Hill Rd, Winhall, VT 05340

    Set along Lower Taylor Hill Road in Winhall, this 21.2 +/- acre offering captures the privacy, natural beauty, and four-season lifestyle that define Southern Vermont living. Rolling terrain, mature woodland, and natural clearings create an exceptional setting for a private Vermont retreat, with the potential for Bromley Mountain views depending on house placement and design.Supported by a

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    56 Lower Taylor Hill Rd, Winhall, VT 05340
  • /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 $4,101,631

    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

      • 0 Days On Market

  • /39

    $495,000

    Under Contract
    • 4 Beds
    • 2 Baths
    • 1,824 Sq Ft

    140 Vermont 30, Winhall, VT 05340

    Quintessential Vermont charm meets modern comfort in this beautifully updated New England farmhouse just minutes from Stratton Mountain. Ideally located only 1 mile from the Stratton Mountain Access Road and just 1/10 mile to the VAST snowmobile trail, this 4-bedroom, 2-bath home offers the perfect four-season retreat. Rich with character, the home features exposed beams, warm hardwood floors,

    Carrie Mathews Winhall Real Estate

    140 Vermont 30, Winhall, 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 $450,480

    Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

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

      Est $512,723

      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

      • 3 Days On Market

  • /49

    $675,000

    • 3 Beds
    • 2 Baths
    • 2,204 Sq Ft

    11 Stratton View Rd, Bondville, VT 05340

    This is not your average chalet. Tucked in the quiet Stratton View neighborhood, just 1 mile from the base of the Stratton Access Road, this 3-bedroom, 2-bath home offers the warmth and character of a classic Vermont chalet with updated systems, thoughtful improvements, two living spaces, and garage space for three vehicles. Offered fully furnished and truly turnkey --right down to the tractor,

    Cheyanne Pugliese

    11 Stratton View Rd, Bondville, VT 05340
  • /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 $944,237

      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

      • 7 Days On Market

  • /2

    $2,500

    $13K PRICE DROP Under Contract
    • Land
    • 7,840 Sq Ft
    • $13,889 per Acre

    0 Clayton Ln Unit 5094564, 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 Clayton Ln Unit 5094564, Jamaica, VT 05343
  • /29

    $550,000

    Sold Jun 19, 2026

    9 F Cobble Ridge Rd, Winhall, VT 05340

    • 3 Beds
    • 3 Baths
    • 2,317 Sq Ft
    • Built 1986

    Last Sold Summary

    • 31% Below List Price
    • $237/SF
    • 293 Days On Market

    Last Listing Agent Carrie Mathews Winhall Real Estate

    9 F Cobble 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

      • 180 Days On Market

  • /59

    $2,350,000

    • 5 Beds
    • 3.5 Baths
    • 4,752 Sq Ft

    6 Sunset Ridge Rd, Winhall, VT 05340

    Set within the exclusive High Meadow community, one of Stratton's most prestigious mountain enclaves, 6 Sunset Ridge is an extraordinary resort residence of post and beam architecture & impeccable craftsmanship. Positioned to capture sweeping views of Stratton Mountain, this exceptional residence offers an unparalleled lifestyle in one of Stratton's most sought-after luxury neighborhoods. From

    Kim Morgan-Wohler Wohler Realty Group

    6 Sunset Ridge Rd, Winhall, VT 05340
  • /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 $776,889

    Last Listing Agent Christiane Carroccio TPW Real Estate

    44 Hilltop Rd, Winhall, VT 05340
    • /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

      • 43 Days On Market

  • /18

    $235,000

    $4K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,356 Sq Ft

    765 Thompsonburg Rd, South Londonderry, VT 05155

    Perfectly positioned in the heart of Vermont's sought-after Golden Triangle, this charming two-bedroom plus loft home offers the ideal balance of year-round recreation and cozy mountain living. Just minutes from Magic Mountain, Bromley Mountain, and Stratton Mountain, you'll enjoy easy access to skiing, hiking, golf, shopping, dining, and all the outdoor adventures Southern Vermont has to

    Carrie Mathews Winhall Real Estate

    765 Thompsonburg Rd, South Londonderry, VT 05155
  • /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 $216,000

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

    5997 Vt Route 30, Jamaica, VT 05343
    • /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

      • 9 Days On Market

  • /30

    $1,040,000

    • 5 Beds
    • 4.5 Baths
    • 3,363 Sq Ft

    1189 Cole Pond Rd, Jamaica, VT 05343

    Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts. The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a seamless

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    1189 Cole Pond Rd, Jamaica, VT 05343
  • /33

    $1,405,025

    Sold Apr 24, 2026

    7 Woodfern Run, Stratton, VT 05360

    • 4 Beds
    • 4 Baths
    • 2,377 Sq Ft
    • Built 2004

    Last Sold Summary

    • 4% Above List Price
    • $591/SF
    • 4 Days On Market

    Last Listing Agent Christiane Carroccio TPW Real Estate

    7 Woodfern Run, Stratton, VT 05360
    • /27

      Not Listed For Sale

      85 E Birch Rd Unit 7, Stratton, VT 05360

      • 2 Beds
      • 2 Baths
      • 1,111 Sq Ft
      • Built 1983
      85 E Birch Rd Unit 7, Stratton, VT 05360

      Last Sold Summary

      • 6 Days On Market

  • /33

    $649,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 1,650 Sq Ft

    39 Pond View Rd Unit 39, Winhall, VT 05340

    Set in a prime location along Stratton Access Road, this Intervale townhouse offers an easygoing mountain lifestyle with everything you need close at hand—including weekend and holiday winter shuttle service to the base lodge.The 3-bedroom + loft, 3-bath layout provides plenty of space for guests, while the open living area brings everyone together with a seamless flow between the kitchen,

    Carrie Mathews Winhall Real Estate

    39 Pond View Rd Unit 39, Winhall, VT 05340
  • /2

    $815,000

    Sold Mar 05, 2026

    B15 Maple Ridge Rd Unit B15, Winhall, VT 05340

    • 4 Beds
    • 3 Baths
    • 2,500 Sq Ft
    • Built 1985

    Last Sold Summary

    • 1% Above List Price
    • $326/SF
    • 0 Days On Market

    Last Listing Agent Andrew King Stratton Real Estate

    B15 Maple Ridge Rd Unit B15, Winhall, VT 05340
    • /26

      Not Listed For Sale

      219 Deerwood Hill, Londonderry, VT 05155

      • 1 Bed
      • 1 Bath
      • 460 Sq Ft
      • Built 2022
      219 Deerwood Hill, Londonderry, VT 05155

      Last Sold Summary

      • 6 Days On Market

  • /5

    $375,000

    $90K PRICE DROP
    • Land
    • 5.54 Acres
    • $67,690 per Acre

    Lot #4 Margeaux Ln, Stratton, VT 05155

    Nestled along a peaceful babbling brook, this 5.54-acre parcel offers an idyllic setting for building the home of your dreams. Surrounded by a serene wooded landscape, the property provides both privacy and tranquility, while still being just moments from the Sun Bowl at Stratton. With a septic permit already approved for a 4-bedroom home, this lot is ready for construction, allowing you to begin

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    Lot #4 Margeaux Ln, Stratton, VT 05155
  • /33

    $50,000

    Sold Dec 05, 2025

    33 W River St, Londonderry, VT 05155

    • 2 Beds
    • 0.5 Baths
    • 414 Sq Ft
    • Built 1952

    Last Sold Summary

    • 17% Below List Price
    • $121/SF
    • 43 Days On Market

    Last Listing Agent Christine Chovan

    33 W River St, Londonderry, VT 05155
    • /21

      Not Listed For Sale

      85 E Birch Rd Unit 4, Stratton, VT 05360

      • 2 Beds
      • 2 Baths
      • 1,111 Sq Ft
      • Built 1983
      85 E Birch Rd Unit 4, Stratton, VT 05360

      Last Sold Summary

      • 3 Days On Market

  • /51

    $5,100,000

    • 10 Beds
    • 9.5 Baths
    • 6,648 Sq Ft

    15 Sawmill Rd, Stratton, VT 05155

    Location, Location, Location. Representing the pinnacle of Stratton Mountain trailside living, 15 Sawmill is a generational property where unrivaled ski-in/ski-out access creates one of Stratton's most exceptional legacy offerings. This is one of the few homes located along the trail - one you admire and wish was yours when you ski by it all winter season! Perfectly positioned directly on the ski

    Kim Morgan-Wohler Wohler Realty Group

    15 Sawmill Rd, Stratton, VT 05155
  • /35

    $339,000

    Sold Oct 20, 2025

    33 Aspen Ln, Bondville, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 1970

    Last Sold Summary

    • 6% Below List Price
    • $303/SF
    • 37 Days On Market

    Current Estimated Value $352,063

    Last Listing Agent Alison Cummings Cummings & Co

    33 Aspen Ln, Bondville, VT 05340
    • /10

      Not Listed For Sale

      0 Mowrey Rd Unit 5012138, Jamaica, VT 05343

      0 Mowrey Rd Unit 5012138, Jamaica, VT 05343

      Last Sold Summary

      • 2 Days On Market

  • /60

    $2,700,000

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

    23 Valley View Rd, Winhall, VT 05340

    Where Eagles Soar! This unsurpassed, top of the mountain panorama stretches for over 40 miles! Located comfortably between Stratton and Manchester on 28 acres perfecting privacy as it's gently rising paved approach sets the tone for this 4000 SF luxury retreat that shall call one back to Vermont over and over again! Memories are made here as this property proves ideal for entertaining or personal

    Laura Beckwith Josiah Allen Real Estate, Inc.

    23 Valley View Rd, Winhall, VT 05340
  • /21

    $590,000

    Sold Nov 25, 2025

    771 Stratton Mountain Access Rd Unit 261, Stratton, VT 05360

    • 2 Beds
    • 2 Baths
    • 916 Sq Ft
    • Built 1999

    Last Sold Summary

    • 6% Below List Price
    • $644/SF
    • 306 Days On Market

    Last Listing Agent Andrew King Stratton Real Estate

    771 Stratton Mountain Access Rd Unit 261, Stratton, VT 05360
    • /10

      Est $464,494

      Not Listed For Sale

      16 Ober Tal Dr Unit E-13, Stratton, VT 05360

      • 1 Bed
      • 1 Bath
      • 850 Sq Ft
      • Built 1983
      16 Ober Tal Dr Unit E-13, Stratton, VT 05360

      Last Sold Summary

      • 10 Days On Market

Showing Results 241 - 280, Page 7 of 18

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