2,288

Winhall, VT Homes

Section Image
  • /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 $344,282

    Last Listing Agent Alison Cummings Cummings & Co

    33 Aspen Ln, Bondville, VT 05340
    • /39

      Est $602,212 Not Listed For Sale

      22 Cranberry Hill Rd, Winhall, VT 05340

      • 3 Beds
      • 2.5 Baths
      • 1,512 Sq Ft
      • Built 1975
      22 Cranberry Hill Rd, Winhall, VT 05340

      Last Sold Summary

      • 8% Above List Price
      • $370/SF
      • 2 Days On Market
      • Last Sold Price $560,000
      • Jul 30, 2024

      Last Listing Agent Mike England Michael England Real Estate

  • /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
  • /60

    $625,000 Sold Nov 26, 2025

    3 Short Rd, Bondville, VT 05340

    • 3 Beds
    • 2.5 Baths
    • 2,034 Sq Ft
    • Built 1885

    Last Sold Summary

    • 12% Below List Price
    • $307/SF
    • 56 Days On Market

    Current Estimated Value $645,888

    Last Listing Agent Mike England Michael England Real Estate

    3 Short Rd, Bondville, VT 05340
    • /33

      Est $596,890 Not Listed For Sale

      1 Burnt Hill Ln, Winhall, VT 05340

      • 4 Beds
      • 2 Baths
      • 2,400 Sq Ft
      • Built 1975
      1 Burnt Hill Ln, Winhall, VT 05340

      Last Sold Summary

      • 22% Above List Price
      • $204/SF
      • 9 Days On Market
      • Last Sold Price $489,000
      • Aug 26, 2024

      Last Listing Agent Carrie Mathews Winhall Real Estate

  • /37

    $829,000 Under Contract

    • 4 Beds
    • 3 Baths
    • 2,797 Sq Ft

    13 Betty Johnson Ln, Bondville, VT 05340

    Experience the magic of Vermont in every season with this stunning four-bedroom, three-bathroom home directly on Stratton Mountain. Your ultimate year-round retreat. Nestled in the heart of Vermont, this property boasts two cozy fireplaces, perfect for warming up after a day of winter adventures or enjoying a crisp autumn evening. With two distinct living areas, you'll find the ideal spaces for

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    13 Betty Johnson Ln, Bondville, VT 05340
  • /31

    $555,000 Sold Feb 12, 2026

    22 Bromley Forest Rd, Bondville, VT 05340

    • 4 Beds
    • 2.5 Baths
    • 2,408 Sq Ft
    • Built 1988

    Last Sold Summary

    • 18% Below List Price
    • $230/SF
    • 185 Days On Market

    Current Estimated Value $578,301

    Last Listing Agent Carrie Mathews Winhall Real Estate

    22 Bromley Forest Rd, Bondville, VT 05340
    • /19

      Not Listed For Sale

      0 Birch Hill Rd Unit Sugar Maple 5003081, Winhall, VT 05340

      • 3 Beds
      • 2 Baths
      • 1,215 Sq Ft
      • Built 1968
      0 Birch Hill Rd Unit Sugar Maple 5003081, Winhall, VT 05340

      Last Sold Summary

      • $272/SF
      • 5 Days On Market
      • Last Sold Price $330,000
      • Aug 16, 2024

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

  • /56

    $929,000 Pending

    • 4 Beds
    • 3 Baths
    • 2,068 Sq Ft

    104 High Meadow Rd, Winhall, VT 05340

    Location says it all. This High Meadow mountain retreat is located in one of Stratton Resort’s premier locations. High Meadow offers winter weekend and holiday shuttle service to the slopes for your convenience. Bathed in sunshine thanks to its southern exposure, this contemporary home welcomes you with a seamless open floor plan that flows effortlessly from the kitchen into expansive

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    104 High Meadow Rd, Winhall, VT 05340
  • /45

    $849,000 Sold Dec 04, 2025

    7 N Brookwood Rd, Winhall, VT 05340

    • 4 Beds
    • 3.5 Baths
    • 2,028 Sq Ft
    • Built 1968

    Last Sold Summary

    • $419/SF
    • 12 Days On Market

    Current Estimated Value $845,468

    Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

    7 N Brookwood Rd, Winhall, VT 05340
    • /33

      Not Listed For Sale

      39 Todd Hill Rd, Jamaica, VT 05343

      • 3 Beds
      • 2 Baths
      • 812 Sq Ft
      • Built 1977
      39 Todd Hill Rd, Jamaica, VT 05343

      Last Sold Summary

      • $714/SF
      • 91 Days On Market
      • Last Sold Price $580,000
      • Oct 26, 2024

      Last Listing Agent Cheyanne Pugliese

  • /38

    $4,999,000

    • 6 Beds
    • 7.5 Baths
    • 8,720 Sq Ft

    454 Mountain Rd, Stratton, VT 05155

    Welcome to a one-of-a-kind 141-acre mountaintop retreat at Stratton Mountain Resort - an extraordinary sanctuary with panoramic views of Stratton, Mount Snow, and Bromley. Designed for elegance and ease, this home is a rare blend of architectural beauty, comfort, and sophistication. A gracious entryway opens to a sunlit living room and library anchored by an 18-foot stone fireplace. Expansive

    Lisa Sullivan Four Seasons Sotheby's Int'l Realty

    454 Mountain Rd, Stratton, VT 05155
  • /10

    $385,000 Sold Sep 10, 2025

    0 River Rd, Winhall, VT 05340

    • Land
    • 24.54 Acres
    • $15,689 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 28 Days On Market

    Last Listing Agent Cheyanne Pugliese

    0 River Rd, Winhall, VT 05340
    • /40

      Not Listed For Sale

      D3 Cobble Ridge Rd, Winhall, VT 05340

      • 4 Beds
      • 3 Baths
      • 2,212 Sq Ft
      • Built 1988
      D3 Cobble Ridge Rd, Winhall, VT 05340

      Last Sold Summary

      • $366/SF
      • 145 Days On Market
      • Last Sold Price $810,000
      • Dec 06, 2024

      Last Listing Agent Carrie Mathews Winhall Real Estate

  • /37

    $975,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 2,280 Sq Ft

    17 Roundtree Rd, Winhall, VT 05340

    Contemporary ski chalet on shuttle route located on a short cul-de-sac in the coveted North Brookwood neighborhood, a stone's throw from the Stratton base lodge. This 4 bedroom, 3 1⁄2 bath home boasts an open plan, walls of windows, and floor-to-ceiling stone fireplace in the Great Room. The pass-through kitchen was fully renovated in 2021 in addition to many other upgrades. Test your skills at

    Sarah Nichols Winhall Real Estate

    17 Roundtree Rd, Winhall, VT 05340
  • /58

    $1,600,000 Sold Dec 19, 2025

    14 Stone House Rd, Winhall, VT 05155

    • 3 Beds
    • 4.5 Baths
    • 4,312 Sq Ft
    • Built 2000

    Last Sold Summary

    • 7% Below List Price
    • $371/SF
    • 8 Days On Market

    Last Listing Agent Jamie Wylie Stratton Real Estate

    14 Stone House Rd, Winhall, VT 05155
    • /40

      Est $948,184 Not Listed For Sale

      41 Rogues Ridge Rd, Winhall, VT 05340

      • 4 Beds
      • 3.5 Baths
      • 1,860 Sq Ft
      • Built 2005
      41 Rogues Ridge Rd, Winhall, VT 05340

      Last Sold Summary

      • 10% Below List Price
      • $565/SF
      • 29 Days On Market
      • Last Sold Price $1,050,000
      • Jul 29, 2024

      Last Listing Agent Christiane Carroccio TPW Real Estate

  • /5

    $375,000

    • 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
  • /44

    $2,200,000 Sold Oct 14, 2025

    19 Old Town Rd, Bondville, VT 05340

    • 5 Beds
    • 7 Baths
    • 7,625 Sq Ft
    • Built 2000

    Last Sold Summary

    • 21% Below List Price
    • $289/SF
    • 190 Days On Market

    Current Estimated Value $2,225,474

    Last Listing Agent Christiane Carroccio TPW Real Estate

    19 Old Town Rd, Bondville, VT 05340
    • /27

      Not Listed For Sale

      5 Oak Rd Unit 5, Winhall, VT 05340

      • 3 Beds
      • 2 Baths
      • 1,215 Sq Ft
      • Built 1968
      5 Oak Rd Unit 5, Winhall, VT 05340

      Last Sold Summary

      • $262/SF
      • 29 Days On Market
      • Last Sold Price $318,000
      • Jun 27, 2024

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

  • /16

    $139,000

    • Land
    • 1.62 Acres
    • $85,802 per Acre

    0 Lower Taylor Hill Rd Unit 19, Winhall, VT 05340

    wooded slightly elevated parcel. With clearing there should be some across valley views. Past soil test indicates proposed septic locations.Five-minute walk to Stratton snowmaking pond.

    Mike England Michael England Real Estate

    0 Lower Taylor Hill Rd Unit 19, Winhall, VT 05340
  • /21

    $416,000 Sold Dec 12, 2025

    21 Deep Woods Cir Unit Lot 27, Winhall, VT 05255

    • 2 Beds
    • 1 Bath
    • 974 Sq Ft
    • Built 1976

    Last Sold Summary

    • 2% Below List Price
    • $427/SF
    • 17 Days On Market

    Last Listing Agent Patti Trudel RE/MAX Four Seasons

    21 Deep Woods Cir Unit Lot 27, Winhall, VT 05255
    • /28

      Not Listed For Sale

      61 Birch Hill Rd Unit 2 Shagbark HIckory, Winhall, VT 05340

      • 3 Beds
      • 2 Baths
      • 1,215 Sq Ft
      • Built 1968
      61 Birch Hill Rd Unit 2 Shagbark HIckory, Winhall, VT 05340

      Last Sold Summary

      • $265/SF
      • 10 Days On Market
      • Last Sold Price $322,500
      • May 10, 2024

      Last Listing Agent Helen Nault

  • /60

    $979,000

    • 4 Beds
    • 3.5 Baths
    • 5,248 Sq Ft

    41-43 Cranberry Hill Rd, Winhall, VT 05340

    This is the ultimate modern Alpine chalet, fully renovated yet boasting the classic flat-sawn balusters characteristic of mountain homes in the Alps. Three expansive floors offer sunny, well-appointed space, beginning with a roomy mudroom, three bedrooms and two bathrooms (one en-suite). Head upstairs to join your friends and family in the open-concept European kitchen/living/dining room with

    Jamie Luke TPW Real Estate

    41-43 Cranberry Hill Rd, Winhall, VT 05340
  • /28

    $815,000 Sold Oct 28, 2025

    6 Roundtree Rd, Winhall, VT 05340

    • 4 Beds
    • 2 Baths
    • 1,908 Sq Ft
    • Built 1971

    Last Sold Summary

    • 4% Below List Price
    • $427/SF
    • 93 Days On Market

    Current Estimated Value $815,563

    Last Listing Agent Christina Dryden Berkshire Hathaway HomeServices Stratton Home

    6 Roundtree Rd, Winhall, VT 05340
    • /15

      Est $446,446 Not Listed For Sale

      300 Vt Route 30, Bondville, VT 05340

      • 2 Beds
      • Built 1952
      300 Vt Route 30, Bondville, VT 05340

      Last Sold Summary

      • 8% Above List Price
      • $474/SF
      • 13 Days On Market
      • Last Sold Price $415,000
      • Apr 11, 2024

      Last Listing Agent Christine Chovan

  • /40

    $735,000

    • 4 Beds
    • 3 Baths
    • 2,317 Sq Ft

    B2 Maple Hill Rd, Winhall, VT 05340

    The Highgate Piper Ridge Townhome is ideally located just a short stroll from the exclusive sports center and provides convenient shuttle service to Stratton’s ski lifts during the winter season. This residence is filled with natural light and features a contemporary kitchen and bathrooms, polished hardwood floors, and elegant tile accents throughout. The one-car garage has been ingeniously

    Mike England Michael England Real Estate

    B2 Maple Hill Rd, Winhall, VT 05340
  • /28

    $770,000 Sold Jul 18, 2025

    5 Stratton Ridge Rd, Winhall, VT 05340

    • 4 Beds
    • 3 Baths
    • 3,676 Sq Ft
    • Built 1980

    Last Sold Summary

    • 4% Below List Price
    • $209/SF
    • 113 Days On Market

    Current Estimated Value $861,883

    Last Listing Agent Carrie Mathews Winhall Real Estate

    5 Stratton Ridge Rd, Winhall, VT 05340
    • /31

      Not Listed For Sale

      43 Middle Ridge Rd Unit 410, Winhall, VT 05155

      • 3 Beds
      • 3.5 Baths
      • 2,140 Sq Ft
      • Built 2004
      43 Middle Ridge Rd Unit 410, Winhall, VT 05155

      Last Sold Summary

      • $678/SF
      • 73 Days On Market
      • Last Sold Price $1,450,000
      • Jul 12, 2024

      Last Listing Agent Stephen Coombs Stratton Real Estate

  • /52

    $2,850,000 Pending

    • 4 Beds
    • 6 Baths
    • 5,082 Sq Ft

    41 Stark Farm Rd, Winhall, VT 05340

    41 Stark Farm is your next stop to happiness and joy. This one-of-a-kind property pairs a beautiful country farmhouse with an incredible party barn built for entertaining. Minutes from Stratton and Bromley to mention just a few major ski mountains and within a 15 minute drive of Manchester you cannot beat this location. On 7.8 landscaped acres with your own private pond large enough to host a

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    41 Stark Farm Rd, Winhall, VT 05340
  • /43

    $1,050,000 Sold Feb 27, 2026

    6 Chad Cir, Winhall, VT 05340

    • 5 Beds
    • 4 Baths
    • 4,788 Sq Ft
    • Built 1983

    Last Sold Summary

    • 5% Below List Price
    • $219/SF
    • 61 Days On Market

    Current Estimated Value $1,095,086

    Last Listing Agent Carrie Mathews Winhall Real Estate

    6 Chad Cir, Winhall, VT 05340
    • /38

      Est $694,342 Not Listed For Sale

      28 Redbrook Rd, Winhall, VT 05340

      • 3 Beds
      • 3 Baths
      • 1,220 Sq Ft
      • Built 1979
      28 Redbrook Rd, Winhall, VT 05340

      Last Sold Summary

      • 12% Above List Price
      • $508/SF
      • 6 Days On Market
      • Last Sold Price $620,000
      • May 03, 2024

      Last Listing Agent Jamie Luke TPW Real Estate

  • /6

    $395,000

    • Land
    • 6.93 Acres
    • $56,999 per Acre

    lot#2 Margeaux Ln, Stratton, VT 05155

    This stunning 6.93-acre parcel offers the perfect setting to build the home of your dreams, just moments from the Sun Bowl at Stratton. Nestled in a serene wooded landscape, the property provides both privacy and tranquility while being ideally located for easy access to all that Stratton has to offer. With a septic permit already approved for a 4-bedroom home, this lot is ready for you to begin

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    lot#2 Margeaux Ln, Stratton, VT 05155
  • /30

    $325,000 Sold Dec 19, 2025

    19 Winhall Condo Rd Unit 5, Winhall, VT 05340

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft
    • Built 1978

    Last Sold Summary

    • $339/SF
    • 12 Days On Market

    Current Estimated Value $325,273

    Last Listing Agent Cheyanne Pugliese

    19 Winhall Condo Rd Unit 5, Winhall, VT 05340
    • /40

      Est $795,372 Not Listed For Sale

      17 Cranberry Hill Rd, Winhall, VT 05340

      • 4 Beds
      • 3.5 Baths
      • 2,017 Sq Ft
      • Built 1967
      17 Cranberry Hill Rd, Winhall, VT 05340

      Last Sold Summary

      • 7% Below List Price
      • $424/SF
      • 8 Days On Market
      • Last Sold Price $855,000
      • Apr 19, 2024

      Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

  • /15

    $99,500

    • Land
    • 1.2 Acres
    • $82,917 per Acre

    23 Moose Hollow Rd, Winhall, VT 05340

    Beautiful parcel located in a highly desirable Winhall neighborhood, just minutes to Bromley and Stratton Mountains, and a short drive to Manchester’s shops and dining. This property offers a State of Vermont potable water supply and wastewater permit in place for a 4-bedroom home. The lot is cleared and ready for construction—an ideal opportunity to build your Vermont retreat.

    Carrie Mathews Winhall Real Estate

    23 Moose Hollow Rd, Winhall, VT 05340
  • /39

    $590,000 Sold Mar 05, 2026

    17 Signal Hill Rd, Winhall, VT 05340

    • 5 Beds
    • 3.5 Baths
    • 2,468 Sq Ft
    • Built 1989

    Last Sold Summary

    • 9% Below List Price
    • $239/SF
    • 104 Days On Market

    Current Estimated Value $594,114

    Last Listing Agent Christiane Carroccio TPW Real Estate

    17 Signal Hill Rd, Winhall, VT 05340
    • /38

      Not Listed For Sale

      233 Vermont 30, Winhall, VT 05340

      • 3 Beds
      • 3 Baths
      • 1,344 Sq Ft
      • Built 1989
      233 Vermont 30, Winhall, VT 05340

      Last Sold Summary

      • $436/SF
      • 4 Days On Market
      • Last Sold Price $585,750
      • May 02, 2024

      Last Listing Agent Carrie Mathews Winhall Real Estate

  • /14

    $649,000

    • 2 Beds
    • 2 Baths
    • 1,148 Sq Ft

    792 Stratton Mtn Access Rd Unit 4310, Stratton, VT 05155

    Maximize your time on the snow in this coveted two-bedroom village watch condo. Featuring a spacious, open layout, the interior boasts a classic wood-burning fireplace and a full kitchen perfect for entertaining. Forget the shuttle; enjoy the seamless convenience of a private ski locker and immediate access to both the lifts and the vibrant resort village. A perfect blend of convenience,

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    792 Stratton Mtn Access Rd Unit 4310, Stratton, VT 05155
  • /36

    $720,000 Sold Oct 21, 2025

    58 Todd Hill Rd, Bondville, VT 05340

    • 4 Beds
    • 4 Baths
    • 2,389 Sq Ft
    • Built 1989

    Last Sold Summary

    • $301/SF
    • 5 Days On Market

    Current Estimated Value $727,863

    Last Listing Agent Jamie Wylie Stratton Real Estate

    58 Todd Hill Rd, Bondville, VT 05340

Showing Results 121 - 160, Page 4 of 18

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