4,494

South Londonderry, VT Homes

Section Image
  • /46

    $299,000

    Sold Jan 22, 2026

    4410 Pikes Falls Rd, Jamaica, VT 05343

    • 3 Beds
    • 2 Baths
    • 2,194 Sq Ft
    • Built 1962

    Last Sold Summary

    • 5% Below List Price
    • $136/SF
    • 5 Days On Market

    Last Listing Agent Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

    4410 Pikes Falls Rd, Jamaica, VT 05343
    • /4

      Est $432,139

      Not Listed For Sale

      283 Main St, South Londonderry, VT 05155

      • 4 Beds
      • 3 Baths
      • 2,600 Sq Ft
      • Built 1825
      283 Main St, South Londonderry, VT 05155

      Last Sold Summary

      • 157 Days On Market

  • /15

    $650,000

    $200K PRICE DROP Under Contract
    • Land
    • 51.93 Acres
    • $12,517 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 5 is 51.93 acres and is located at the top of the subdivision. This parcel is very unique, and

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /31

    $405,000

    Sold Mar 05, 2026

    132 Pratt Bridge Rd, Jamaica, VT 05343

    • 3 Beds
    • 2 Baths
    • 1,814 Sq Ft
    • Built 1987

    Last Sold Summary

    • 13% Below List Price
    • $223/SF
    • 140 Days On Market

    Current Estimated Value $430,632

    Last Listing Agent Lisa Sullivan Four Seasons Sotheby's Int'l Realty

    132 Pratt Bridge Rd, Jamaica, VT 05343
    • /38

      Est $649,760

      Not Listed For Sale

      116 Deerwood Hill, South Londonderry, VT 05155

      • 3 Beds
      • 2.5 Baths
      • 1,856 Sq Ft
      • Built 1977
      116 Deerwood Hill, South Londonderry, VT 05155

      Last Sold Summary

      • 3 Days On Market

  • /26

    $450,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,215 Sq Ft

    36 Birch Hill Rd Unit 8 Red Maple, Winhall, VT 05340

    Exceptional Birch Hill residence showcasing one of the community’s most impressive renovations, designed for modern mountain living. At the heart of the home is a stunning kitchen that seamlessly blends style, function, and warmth — ideal for lively après-ski entertaining or relaxed Vermont weekends.With three well-appointed bedrooms plus an expansive den, there is ample space for family and

    Helen Nault

    36 Birch Hill Rd Unit 8 Red Maple, Winhall, VT 05340
  • /15

    $370,000

    Sold Aug 04, 2025

    761 Stratton Mountain Access Rd Unit 231, Stratton, VT 05360

    • 1 Bed
    • 1 Bath
    • 580 Sq Ft
    • Built 1999

    Last Sold Summary

    • 13% Below List Price
    • $638/SF
    • 120 Days On Market

    Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

    761 Stratton Mountain Access Rd Unit 231, Stratton, VT 05360
    • /37

      Est $498,601

      Not Listed For Sale

      76 Tallwood Cir, Londonderry, VT 05148

      • 3 Beds
      • 2 Baths
      • 976 Sq Ft
      • Built 1972
      76 Tallwood Cir, Londonderry, VT 05148

      Last Sold Summary

      • 4 Days On Market

  • /32

    $1,975,000

    • 4 Beds
    • 3 Baths
    • 3,212 Sq Ft

    74 N Brookwood Rd, Stratton, VT 05360

    PRIME LOCATION near the coveted STRATTON MOUNTAIN RESORT. This EXCEPTIONAL four bedroom three bathroom turn-key home is PRIVATELY SITUATED on 1.5 acres and READY TO BE ENJOYED YEAR ROUND. Snowmobile right from the house to access thousands of acres of pristine VAST snowmobile trails for ENDLESS WINTER ADVENTURE. Ski home to the Covered Bridge neighborhood or hop on the resort shuttle, which runs

    Paul Marino WWW.FLATFEEMLS4FREE.COM

    74 N Brookwood Rd, Stratton, VT 05360
  • /53

    $1,525,000

    Sold Sep 30, 2025

    3333 Under the Mountain Rd, Londonderry, VT 05148

    • 3 Beds
    • 3.5 Baths
    • 5,105 Sq Ft
    • Built 2003

    Last Sold Summary

    • $299/SF
    • 7 Days On Market

    Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    3333 Under the Mountain Rd, Londonderry, VT 05148
    • /29

      Est $263,370

      Not Listed For Sale

      398 Tallwood Cir, Londonderry, VT 05148

      • 2 Beds
      • 1 Bath
      • 696 Sq Ft
      • Built 1970
      398 Tallwood Cir, Londonderry, VT 05148

      Last Sold Summary

      • 47 Days On Market

  • /28

    $729,000

    Under Contract
    • 4 Beds
    • 2 Baths
    • 2,055 Sq Ft

    21 Burnt Hill Rd, Winhall, VT 05341

    Welcome to Gone Ski Inn, your cozy, all-season mountain retreat in the heart of Vermont! This charming home features four inviting bedrooms and two well-appointed bathrooms, offering plenty of space to unwind after a day of adventure. In the winter, cozy up by the crackling wood-burning fireplace , toasty wood stove or relax in the soothing hot tub under the stars. With ski trails just minutes

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    21 Burnt Hill Rd, Winhall, VT 05341
  • /51

    $434,000

    Sold Feb 27, 2026

    12 Stratton West Rd Unit 12, Winhall, VT 05340

    • 5 Beds
    • 2 Baths
    • 1,888 Sq Ft
    • Built 1968

    Last Sold Summary

    • 1% Below List Price
    • $230/SF
    • 6 Days On Market

    Last Listing Agent Robert Sabol Wohler Realty Group

    12 Stratton West Rd Unit 12, Winhall, VT 05340
    • /40

      Est $981,568

      Not Listed For Sale

      929 Middletown Rd, South Londonderry, VT 05155

      • 5 Beds
      • 3.5 Baths
      • 3,354 Sq Ft
      • Built 1850
      929 Middletown Rd, South Londonderry, VT 05155

      Last Sold Summary

      • 6 Days On Market

  • /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
  • /24

    $1,025,000

    Sold Oct 10, 2025

    10 Middle Ridge Rd, Winhall, VT 05155

    • 4 Beds
    • 3.5 Baths
    • 2,160 Sq Ft
    • Built 1988

    Last Sold Summary

    • 6% Above List Price
    • $475/SF
    • 5 Days On Market

    Last Listing Agent Christiane Carroccio TPW Real Estate

    10 Middle Ridge Rd, Winhall, VT 05155
    • /21

      Est $602,000

      Not Listed For Sale

      3378 Under the Mountain Rd, South Londonderry, VT 05155

      • 5 Beds
      • 4.5 Baths
      • 4,482 Sq Ft
      • Built 2007
      3378 Under the Mountain Rd, South Londonderry, VT 05155

      Last Sold Summary

      • 47 Days On Market

  • /7

    $875,000

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    447 Rock Bottom Ln, Peru, VT 05152

    toric Jack's Hill House, masterfully designed by Vermont Vernacular Designs. Nestled on approximately 21 private acres along a winding country road and bordered by National Forest, Still Meadows Farm offers a rare blend of timeless New England character, modern comfort, and unparalleled access to Vermont's outdoor lifestyle. Outdoor enthusiasts will appreciate the property's proximity to the

    Andy Reed Four Seasons Sotheby's Int'l Realty

    447 Rock Bottom Ln, Peru, VT 05152
  • /56

    $2,600,000

    Sold May 01, 2026

    25 Mountain Haunts Rd, Winhall, VT 05340

    • 6 Beds
    • 6.5 Baths
    • 6,650 Sq Ft
    • Built 1960

    Last Sold Summary

    • 13% Below List Price
    • $391/SF
    • 366 Days On Market

    Current Estimated Value $2,653,946

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    25 Mountain Haunts Rd, Winhall, VT 05340
    • /13

      Est $205,858

      Not Listed For Sale

      1797 Thompsonburg Rd, South Londonderry, VT 05155

      • 2 Beds
      • 1 Bath
      • 1,146 Sq Ft
      • Built 1956
      1797 Thompsonburg Rd, South Londonderry, VT 05155

      Last Sold Summary

      • 8 Days On Market

  • /55

    $2,950,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 3,762 Sq Ft

    59 Garden Loop Rd, Winhall, VT 05340

    Move into this brand new stunning custom contemporary set on over 3 acres in coveted Stratton ski country. This exceptional modern design offers elevated living with superior craftsmanship and sweeping endless views. Featuring four well appointed ensuites with polished baths boasting radiant heated floors, half bath, family room and dual laundry areas. The well designed kitchen with Italian

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    59 Garden Loop Rd, Winhall, VT 05340
  • /54

    $1,875,000

    Sold May 08, 2026

    97 N Brookwood Rd, Stratton, VT 05360

    • 4 Beds
    • 4.5 Baths
    • 2,486 Sq Ft
    • Built 1968

    Last Sold Summary

    • 9% Below List Price
    • $754/SF
    • 170 Days On Market

    Current Estimated Value $1,620,250

    Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    97 N Brookwood Rd, Stratton, VT 05360
    • /18

      Est $559,803

      Not Listed For Sale

      155 Pratt Bridge Rd, Jamaica, VT 05343

      • 4 Beds
      • 2.5 Baths
      • 2,050 Sq Ft
      • Built 1971
      155 Pratt Bridge Rd, Jamaica, VT 05343

      Last Sold Summary

      • 3 Days On Market

  • /44

    $815,000

    Under Contract
    • 4 Beds
    • 4.5 Baths
    • 2,980 Sq Ft

    74 Pond View Rd, Winhall, VT 05340

    This spacious and well-maintained 4-bedroom, 4.5-bathroom condo in Stratton’s desirable Intervale community offers nearly 3,000 square feet of comfortable mountain living, just minutes from the Base Lodge with winter shuttle service. Nestled among the trees for added privacy, the home features an open-concept main level with cathedral ceilings, abundant natural light, a wood-burning fireplace,

    Christine Chovan

    74 Pond View Rd, Winhall, VT 05340
  • /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 $991,675

      Not Listed For Sale

      1223 Cole Pond Rd, Jamaica, VT 05343

      • 3 Beds
      • 4 Baths
      • 2,197 Sq Ft
      • Built 1970
      1223 Cole Pond Rd, Jamaica, VT 05343

      Last Sold Summary

      • 7 Days On Market

  • /27

    $379,000

    Pending
    • 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. 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 space for preparing meals and

    The Malley Group KW Vermont

    292 Tallwood Cir, Londonderry, VT 05148
  • /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
    • /34

      Est $349,339

      Not Listed For Sale

      6217 Vt Route 30, Jamaica, VT 05343

      • 2 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1969
      6217 Vt Route 30, Jamaica, VT 05343

      Last Sold Summary

      • 100 Days On Market

  • /40

    $899,000

    $301K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,252 Sq Ft

    E1 Rock Ridge Rd, Winhall, VT 05155

    Ideally situated near the renowned Stratton Mountain Resort and offering convenient shuttle service to the slopes, this spacious four-bedroom, three-bath ski condo is thoughtfully designed for year-round enjoyment. A true retreat for outdoor enthusiasts, the home provides effortless access to world-class skiing in the winter and outstanding hiking and mountain biking throughout the warmer months.

    Christine Chovan

    E1 Rock Ridge Rd, Winhall, VT 05155
  • /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
    • /34

      Not Listed For Sale

      498 Goodaleville Rd, South Londonderry, VT 05155

      • 8 Beds
      • 6 Baths
      • 4,600 Sq Ft
      • Built 1860
      498 Goodaleville Rd, South Londonderry, VT 05155

      Last Sold Summary

      • 22 Days On Market

  • /12

    $178,000

    $7K PRICE DROP
    • Land
    • 8 Acres
    • $22,250 per Acre

    4441 Vermont 30, Jamaica, VT 05343

    Set amidst a peaceful woodland setting, this 8.0± acre parcel offers the perfect balance of seclusion and convenience—tucked away for privacy yet easily accessible year-round.. Currently being subdivided from a larger tract, this parcel presents a rare chance to shape your vision from the ground up.A five-bedroom Wastewater Permit has been approved, and a professional boundary survey is

    Helen Nault

    4441 Vermont 30, Jamaica, VT 05343
  • /27

    $1,300,000

    Sold Jul 31, 2025

    0 W Hill Rd S Unit 5006431, Jamaica, VT 05343

    • Land
    • 591 Acres
    • $2,200 per Acre

    Last Sold Summary

    • 32% Below List Price
    • 136 Days On Market

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

    0 W Hill Rd S Unit 5006431, Jamaica, VT 05343
    • /40

      Est $497,396

      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

  • /37

    $690,000

    $40K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,635 Sq Ft

    341 Under the Mountain Rd, Londonderry, VT 05148

    Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly

    Andy Reed Four Seasons Sotheby's Int'l Realty

    341 Under the Mountain Rd, Londonderry, VT 05148
  • /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
    • /39

      Est $422,302

      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

  • /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
  • /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

Showing Results 41 - 80, Page 2 of 18

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