4,492

South Londonderry, VT Homes

Section Image
  • /40

    $595,000

    Sold Nov 10, 2025

    4A Ridge, Winhall, VT 05340

    • 3 Beds
    • 3 Baths
    • 1,886 Sq Ft
    • Built 1985

    Last Sold Summary

    • 3% Below List Price
    • $315/SF
    • 31 Days On Market

    Last Listing Agent Christiane Carroccio TPW Real Estate

    4A Ridge, Winhall, VT 05340
    • /40

      Est $532,369

      Not Listed For Sale

      886 Dalewood Rd, Jamaica, VT 05343

      • 3 Beds
      • 2.5 Baths
      • 768 Sq Ft
      • Built 1965
      886 Dalewood Rd, Jamaica, VT 05343

      Last Sold Summary

      • 3 Days On Market

  • /12

    $450,000

    • Land
    • 10.26 Acres
    • $43,860 per Acre

    4.1 Pearl Buck Dr, Winhall, VT 05340

    One of the last significant VIEW lots available on the mountain , with unrivaled 360 degree views, including dead on views of Stratton Mountain trails. The pinnacle of this 10.26 acre lot is deserving of an exceptionally designed and expansive home in this premium location with commanding views.Prime for a legacy property in a most desirable location, just 5 minutes to the Stratton Base Area,

    Kim Morgan-Wohler Wohler Realty Group

    4.1 Pearl Buck Dr, Winhall, VT 05340
  • /43

    $860,000

    Sold Jan 23, 2026

    8 E Birch Rd Unit 103, Stratton, VT 05360

    • 5 Beds
    • 4 Baths
    • 2,238 Sq Ft
    • Built 1979

    Last Sold Summary

    • 7% Below List Price
    • $384/SF
    • 111 Days On Market

    Last Listing Agent Cheyanne Pugliese

    8 E Birch Rd Unit 103, Stratton, VT 05360
    • /39

      Est $426,933

      Not Listed For Sale

      559 Pratt Bridge Rd, Jamaica, VT 05343

      • 4 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 1978
      559 Pratt Bridge Rd, Jamaica, VT 05343

      Last Sold Summary

      • 181 Days On Market

  • /38

    $375,000

    • Land
    • 1.23 Acres
    • $304,878 per Acre

    0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340

    Exceptional offering. This premier parcel defines phase II of Ravenwood, an enclave of distinctive and premier mountain residences. This notable site offers extraordinary mountain views, direct access from Winhall Hollow Road and still enjoys all the benefits and amenities of The Ravenwood Neighborhood Association. Combining, privacy, natural beauty and convenience, this well-established

    Kim Morgan-Wohler Wohler Realty Group

    0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340
  • /24

    $680,000

    Sold Apr 22, 2026

    761 Stratton Mountain Access Rd Unit 322, Stratton, VT 05360

    • 2 Beds
    • 2 Baths
    • 1,020 Sq Ft
    • Built 1998

    Last Sold Summary

    • $667/SF
    • 6 Days On Market

    Last Listing Agent Andrew King Stratton Real Estate

    761 Stratton Mountain Access Rd Unit 322, Stratton, VT 05360
    • /40

      Est $523,854

      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

      • 44 Days On Market

  • /57

    $850,000

    • 5 Beds
    • 4 Baths
    • 3,218 Sq Ft

    4880 Pikes Falls Rd, Jamaica, VT 05343

    Welcome to your perfect four-season retreat nestled just minutes from Stratton Mountain Ski Resort. This authentic 5-bedroom, 4-bathroom log cabin plenty of space throughout, with ample natural light and that signature Vermont charm and cozy ambiance. A large kitchen, combined with an open dining area and expansive wrap around deck, offer a multitude of opportunities for seasonal gatherings no

    Mike England Michael England Real Estate

    4880 Pikes Falls Rd, Jamaica, VT 05343
  • /16

    $600,000

    Sold Nov 07, 2025

    761 Stratton Mountain Access Rd Unit 240, Stratton, VT 05360

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

    Last Sold Summary

    • 6% Below List Price
    • $655/SF
    • 198 Days On Market

    Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

    761 Stratton Mountain Access Rd Unit 240, Stratton, VT 05360
    • /31

      Est $606,795

      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

      • 56 Days On Market

  • /33

    $1,399,999

    • 6 Beds
    • 4 Baths
    • 3,800 Sq Ft

    121 High Meadow Rd, Winhall, VT 05340

    Bring the whole household to this great place with lots of room for fun. A 6-bedroom, 4-bathroom Adirondack-style Ski Chalet located in a neighborhood just minutes from the Stratton Mountain Ski Resort, with free door-to-mountain shuttle service on select days. Amenities include four (4) fireplaces, best hot-tub on the market, an in home gym, electric sauna, pool table, SuperChexx Bubble Hockey

    Ralph Harvey Listwithfreedom.com

    121 High Meadow Rd, Winhall, VT 05340
  • /4

    $225,000

    Sold Dec 19, 2025

    00 Margeaux Ln, Stratton, VT 05155

    • Land
    • 1.99 Acres
    • $113,065 per Acre

    Last Sold Summary

    • 189 Days On Market

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

    00 Margeaux Ln, Stratton, VT 05155
    • /30

      Est $618,086

      Not Listed For Sale

      5600 Pikes Falls Rd, Jamaica, VT 05343

      • 3 Beds
      • 2 Baths
      • 1,459 Sq Ft
      • Built 1977
      5600 Pikes Falls Rd, Jamaica, VT 05343

      Last Sold Summary

      • 170 Days On Market

  • /15

    $59,900

    $15K PRICE DROP
    • Land
    • 2 Acres
    • $29,950 per Acre

    585 Sawmill Rd, Stratton, VT 05360

    Ready to build your Vermont dream home! Perfectly positioned between Stratton Mountain and Mount Snow, this exceptional 2-acre property offers the ideal blend of privacy, recreation, and convenience in the highly desirable Snow Mountain Farms community.Set within a picturesque mountain setting, the property is already prepared for construction with a cleared building envelope, driveway,

    Carrie Mathews Winhall Real Estate

    585 Sawmill Rd, Stratton, VT 05360
  • /19

    $426,000

    Sold Jan 16, 2026

    46-48 Lower Taylor Hill Rd, Winhall, VT 05340

    • 2 Beds
    • 2 Baths
    • 1,798 Sq Ft
    • Built 1963

    Last Sold Summary

    • 1% Above List Price
    • $237/SF
    • 1 Day On Market

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

    46-48 Lower Taylor Hill Rd, Winhall, VT 05340
    • /25

      Est $753,210

      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

      • 15 Days On Market

  • /4

    $400,000

    • Land
    • 8.01 Acres
    • $49,938 per Acre

    248 French Hollow Rd, Winhall, VT 05340

    Legacy family property, held until now for its premier location and extraordinary views of Stratton Mountain. Acreage offers a building site that is privately situated off the road with a 4 bedroom state septic permit and ready for the mountain home you have been hoping to create! A beautiful parcel with level plateau for building and a moderate slope down to its lower boundary. Surrounded by a

    Kim Morgan-Wohler Wohler Realty Group

    248 French Hollow Rd, Winhall, VT 05340
  • /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
    • /13

      Not Listed For Sale

      234 Mountain Rd, Stratton, VT 05155

      234 Mountain Rd, Stratton, VT 05155

      Last Sold Summary

      • 501 Days On Market

  • /18

    $535,000

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft

    12 Ober Tal Dr Unit C14, Stratton, VT 05360

    Opportunity awaits in this trailside condominium at Stratton Mountain Resort. Ideally positioned for convenient access to the Tamarack Chairlift and Stratton Village, this residence offers the mountain lifestyle buyers seek with direct access to skiing, dining, shopping, and year-round resort amenities. Inside, a wood-burning fireplace anchors the living area, creating an inviting space to gather

    Timothy Mich Doddridge Stratton Real Estate

    12 Ober Tal Dr Unit C14, Stratton, VT 05360
  • /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 $919,703

    Last Listing Agent Helen Nault

    460 Stratton Gate Rd, Jamaica, VT 05343
    • /37

      Est $456,447

      Not Listed For Sale

      400 Edie Ln, Jamaica, VT 05343

      • 3 Beds
      • 2 Baths
      • 1,760 Sq Ft
      • Built 1987
      400 Edie Ln, Jamaica, VT 05343

      Last Sold Summary

      • 315 Days On Market

  • /22

    $595,000

    • 4 Beds
    • 2 Baths
    • 1,430 Sq Ft

    9 Mountain Acres Rd, Jamaica, VT 05343

    Completely renovated and move-in ready, this stunning mountain home offers the perfect blend of comfort and convenience. The full interior renovation includes a brand-new kitchen and bathroom (as well as an updated second bath) , updated bedrooms, new doors, fresh paint, and beautiful new flooring throughout. A propane fireplace adds warmth and charm, while a newly installed mini-split system

    Carrie Mathews Winhall Real Estate

    9 Mountain Acres Rd, Jamaica, VT 05343
  • /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 $236,680

    Last Listing Agent TG Glazer Winhall Real Estate

    8365 Vt Route 30, Jamaica, VT 05343
    • /37

      Est $355,202

      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

      • 24 Days On Market

  • /13

    $120,000

    • Land
    • 4.68 Acres
    • $25,641 per Acre

    8559 Vt Route 30, Jamaica, VT 05343

    Double the Lots, Half the Drama.Why buy one lot when you can have two for the price of... well, this one? Here are 4.68 acres of "ready-to-go" land. Permits are secured for a 3 bedroom house on each lot, and the septic is already there, so you don't have to spend your weekends at town hall meetings. Build on both, or build on one and sell the other to that friend who always "forgets" their

    TG Glazer Winhall Real Estate

    8559 Vt Route 30, Jamaica, VT 05343
  • /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
    • /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

      • 33 Days On Market

  • /31

    $680,000

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

    778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155

    Nestled right on the slopes of Stratton Mountain Resort, this two bedroom two ensuite bathroom condominium offers true ski-in/ski-out convenience for your winter getaway. You'll find yourself just steps from the Villager chairlift, beginner ski area as well as a stone's throw to the shops and restaurants in the Stratton Village. An open-concept living/dinning/kitchen area that features a stone

    Timothy Mich Doddridge Stratton Real Estate

    778 Stratton Mountain Access Rd Unit 2302, 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
    • /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

      • 46 Days On Market

  • /50

    $1,800,000

    • 4 Beds
    • 5 Baths
    • 4,853 Sq Ft

    95 Middletown Rd, South Londonderry, VT 05155

    One-of-a-Kind Vermont Lifestyle PropertyHome, Income & Creative Opportunity Welcome to an exceptional Southern Vermont offering that blends refined country living with rare income and lifestyle flexibility. Set on 2.4 picturesque acres in South Londonderry, this beautifully restored 1865 property is first and foremost a warm and inviting 4-bedroom home—rich in character, thoughtfully updated,

    Eric Nathan Nathan Auction & Real Estate Inc.

    95 Middletown Rd, South Londonderry, VT 05155
  • /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 $1,341,298

    Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

    147 High Meadow Rd, Winhall, VT 05340
    • /40

      Est $2,209,226

      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

      • 18 Days On Market

  • /16

    $365,000

    $25K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,536 Sq Ft

    120 Green Mountain Trail, Londonderry, VT 05148

    Set on 3.9 level acres in a quiet neighborhood just minutes from the village of Londonderry, this four-bedroom, two-bath chalet offers comfortable year-round living or an ideal Vermont getaway. The home features a functional floor plan with four bedrooms, generous living space, and family room Recent improvements include a brand-new roof (2026) and the added peace of mind of a fully operational

    Wilkie Bushby TPW Real Estate

    120 Green Mountain Trail, Londonderry, VT 05148
  • /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 $494,496

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

    3 Strattonwald Rd, Winhall, VT 05340
    • /25

      Not Listed For Sale

      75 E Birch Rd Unit 21, Stratton, VT 05360

      • 2 Beds
      • 2 Baths
      • 1,150 Sq Ft
      • Built 1983
      75 E Birch Rd Unit 21, Stratton, VT 05360

      Last Sold Summary

      • 82 Days On Market

  • /26

    $850,000

    • 3 Beds
    • 3 Baths
    • 2,598 Sq Ft

    C-4 Ridge Rd Unit C-4, Winhall, VT 05340

    Experience four-season Vermont living in this beautifully appointed end-unit townhome in the highly sought-after Highgate neighborhood at Piper Ridge, one of Stratton Mountain's premier resort communities. Ideally located in Winhall, Vermont, just minutes from Stratton Mountain Resort, this spacious 3-bedroom, 3-bath residence offers exceptional privacy, abundant natural light, The thoughtfully

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    C-4 Ridge Rd Unit C-4, Winhall, VT 05340
  • /2

    $395,000

    Sold May 11, 2026

    75 E Birch Rd Unit 35, Stratton, VT 05360

    • 2 Beds
    • 2 Baths
    • 1,119 Sq Ft
    • Built 1983

    Last Sold Summary

    • 1% Below List Price
    • $353/SF
    • 22 Days On Market

    Last Listing Agent Kristin Pirie

    75 E Birch Rd Unit 35, Stratton, VT 05360

Showing Results 81 - 120, Page 3 of 18

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