South Londonderry, VT Homes

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  /31

  $895,000 Sold Dec 12, 2025

  73 Cranberry Hill Rd, Winhall, VT 05340

  • 4 Beds
  • 4.5 Baths
  • 2,658 Sq Ft
  • Built 1984

  Last Sold Summary

  • 8% Below List Price
  • $337/SF
  • 222 Days On Market

  Last Listing Agent Carrie Mathews Winhall Real Estate

  73 Cranberry Hill Rd, Winhall, VT 05340
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• 

  

  

  /4

  Est $427,738 Not Listed For Sale

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

  283 Main St, South Londonderry, VT 05155

  283 Main St, South Londonderry, VT 05155
• 

  

  

  /51

  $585,000

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

  1886 Winhall Hollow Rd, South Londonderry, VT 05155

  Exceptional property tucked amidst nature with views toward Magic. Whether you're a weekend warrior looking to enjoy everything the Green Mountains have to offer or looking for a year round residence with great schools, this property offers an optimal location- convenient to Stratton, Bromley and Magic Mountains as well as Burr and Burton Academy and Floodbrook School. Gourmet kitchen with gas

  Kim Morgan-Wohler Wohler Realty Group

  1886 Winhall Hollow Rd, South Londonderry, VT 05155
• 

  

  

  /22

  $450,000 Sold Jan 31, 2025

  8 Ober Tal Dr Unit A24, Stratton, VT 05360

  • 1 Bed
  • 2 Baths
  • 850 Sq Ft
  • Built 1983

  Last Sold Summary

  • 3% Below List Price
  • $529/SF
  • 155 Days On Market

  Current Estimated Value $455,682

  Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

  8 Ober Tal Dr Unit A24, Stratton, VT 05360
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  /38

  Est $691,051 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,856 Sq Ft

  116 Deerwood Hill, South Londonderry, VT 05155

  116 Deerwood Hill, South Londonderry, VT 05155
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  /46

  $315,000 Under Contract

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

  4410 Pikes Falls Rd, Jamaica, VT 05343

  This charming cabin in the woods is the perfect retreat for those seeking adventure and tranquility alike. Surrounded by 10.7 acres of forest, it offers a cozy haven just a short walk from the breathtaking Pikes Falls and is 5 minutes to Stratton Mountain, ideal for skiing enthusiasts during the winter months. In warmer weather, the nearby trails beckon hikers and mountain bikers to explore the

  Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

  4410 Pikes Falls Rd, Jamaica, VT 05343
• 

  

  /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
• 

  

  /23

  Est $258,876 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  534 Sherwood Forest, Londonderry, VT 05148

  534 Sherwood Forest, Londonderry, VT 05148
• 

  

  /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
• 

  

  /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
• 

  

  /37

  Est $532,107 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 976 Sq Ft

  76 Tallwood Cir, Londonderry, VT 05148

  76 Tallwood Cir, Londonderry, VT 05148
• 

  

  /31

  $435,000

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

  132 Pratt Bridge Rd, Jamaica, VT 05343

  Welcome to this charming Vermont getaway, custom - built and lovingly maintained by the original owners. Ideally located just minutes from Stratton Mountain and within easy reach of Bromley and Magic for a full season of winter adventure. In the warmer months, enjoy nearby lakes perfect for swimming, paddling, or simply relaxing by the water.Inside, the home offers 3 bedrooms and 2 full

  Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  132 Pratt Bridge Rd, Jamaica, VT 05343
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  /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
• 

  

  /29

  Est $276,853 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 696 Sq Ft

  398 Tallwood Cir, Londonderry, VT 05148

  398 Tallwood Cir, Londonderry, VT 05148
• 

  

  /59

  $1,300,000

  • 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
• 

  

  /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 $1,003,165 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,354 Sq Ft

  929 Middletown Rd, South Londonderry, VT 05155

  929 Middletown Rd, South Londonderry, VT 05155
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  /51

  $439,000 Under Contract

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

  12 Stratton West Rd Unit 12, Winhall, VT 05340

  This 5 bedroom, 2 full bath townhouse is the perfect getaway for ski enthusiasts and nature lovers alike. It is conveniently located just minutes to Stratton Mountain Resort. You'll enjoy year-round access to skiing, hiking, paddling, golfing, and many additional Southern Vermont area amenities. Enjoy three floors of spacious living. Enter through the large mudroom with exceptional storage for

  Robert Sabol Wohler Realty Group

  12 Stratton West Rd Unit 12, Winhall, VT 05340
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  /52

  $800,000 Sold Feb 13, 2025

  E11 Rock Ridge Rd, Winhall, VT 05155

  • 3 Beds
  • 3 Baths
  • 2,300 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $348/SF
  • 47 Days On Market

  Last Listing Agent Terry Hill Berkshire Hathaway HomeServices Stratton Home

  E11 Rock Ridge Rd, Winhall, VT 05155
• 

  

  /21

  Est $519,500 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,482 Sq Ft

  3378 Under the Mountain Rd, South Londonderry, VT 05155

  3378 Under the Mountain Rd, South Londonderry, VT 05155
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  /56

  $2,999,000

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

  25 Mountain Haunts Rd, Winhall, VT 05340

  Attend the PUBLIC OPEN HOUSE Monday February 17 from 10:00-2:00. 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

  Kim Morgan-Wohler Wohler Realty Group

  25 Mountain Haunts Rd, Winhall, VT 05340
• 

  

  /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
• 

  

  /29

  Est $822,432 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,156 Sq Ft

  109 Fieldstone Way, South Londonderry, VT 05155

  109 Fieldstone Way, South Londonderry, VT 05155
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  /54

  $2,050,000

  • 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
• 

  

  /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
• 

  

  /13

  Est $159,218 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,146 Sq Ft

  1797 Thompsonburg Rd, South Londonderry, VT 05155

  1797 Thompsonburg Rd, South Londonderry, VT 05155
• 

  

  /43

  $890,000 Under Contract

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

  8 E Birch Rd Unit 103, Stratton, VT 05360

  Rare 5BR/4BA Stratton Townhome | Ski-Back Access | Designer Furnished | Spacious, fully renovated 5-bedroom, 4-bath townhome at Stratton with ski-back access. Professionally designed and furnished by ACK Design, this move-in-ready home blends mountain charm with modern finishes. The main level features hardwood floors, a stunning floor-to-ceiling stone fireplace, and a granite kitchen with

  Cheyanne Pugliese

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

  

  /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
• 

  

  /18

  Est $560,117 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,050 Sq Ft

  155 Pratt Bridge Rd, Jamaica, VT 05343

  155 Pratt Bridge Rd, Jamaica, VT 05343
• 

  

  /9

  $185,000

  • Land
  • 8 Acres
  • $23,125 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
• 

  

  /60

  $2,100,000 Sold May 02, 2025

  18 Rocky Dell Rd, Winhall, VT 05340

  • 7 Beds
  • 5.5 Baths
  • 6,195 Sq Ft
  • Built 2007

  Last Sold Summary

  • 14% Below List Price
  • $339/SF
  • 246 Days On Market

  Current Estimated Value $2,061,985

  Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

  18 Rocky Dell Rd, Winhall, VT 05340
• 

  

  /40

  Est $928,879 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,197 Sq Ft

  1223 Cole Pond Rd, Jamaica, VT 05343

  1223 Cole Pond Rd, Jamaica, VT 05343
• 

  

  /15

  $470,000

  • 2 Beds
  • 2 Baths
  • 1,353 Sq Ft

  49 High Point Dr Unit A-14, Stratton, VT 05360

  49 High Point Drive, Crown Point A14, Stratton, VTIncredible opportunity to make Stratton Mountain Resort a place to call home. Nestled in the Green Mountains of Vermont, Crown Point offers easy condominium living close to the Stratton Mountain Resort Village. Shuttle service to the base area for skiing and riding. An outdoor pool and BBQ area is inviting for summer use. This one-level 2

  Andrew King Stratton Real Estate

  49 High Point Dr Unit A-14, Stratton, VT 05360
• 

  /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
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  /34

  Not Listed For Sale

  • 8 Beds
  • 6 Baths
  • 4,600 Sq Ft

  498 Goodaleville Rd, South Londonderry, VT 05155

  498 Goodaleville Rd, South Londonderry, VT 05155
• 

  

  /19

  $420,000 Under Contract

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

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

  Escape to a charming two-bedroom adorable chalet where function meets tranquility. The living room is enhanced by exposed beams and skylights that welcome abundant natural light. The traditional fireplace adorned with decorative tile invites cozy conversation on snow filled nights. The This home features 1.75 baths, a dedicated laundry room, and a versatile flex space ready to be your home office

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  46-48 Lower Taylor Hill 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

  Last Listing Agent Helen Nault

  460 Stratton Gate Rd, Jamaica, VT 05343
• 

  

  /40

  Est $630,048 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 768 Sq Ft

  886 Dalewood Rd, Jamaica, VT 05343

  886 Dalewood Rd, Jamaica, VT 05343
• 

  

  /37

  $730,000

  • 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
• 

  

  /27

  $245,000 Sold Nov 14, 2025

  8365 Vermont 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

  Last Listing Agent TG Glazer Winhall Real Estate

  8365 Vermont 30, Jamaica, VT 05343

Showing Results 41 - 80, Page 2 of 18