2,306

Winhall, VT Homes

Section Image
  • /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
    • /33

      Est $603,327

      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

      • 9 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
  • /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 $781,925

    Last Listing Agent Christiane Carroccio TPW Real Estate

    44 Hilltop Rd, Winhall, 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

      • 5 Days On Market

  • /16

    $139,000

    Pending
    • 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
  • /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
    • /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

      • 91 Days On Market

  • /59

    $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
  • /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 $337,654

    Last Listing Agent Alison Cummings Cummings & Co

    33 Aspen Ln, Bondville, 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

      • 145 Days On Market

  • /40

    $720,000

    $15K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,317 Sq Ft

    B2 Maple Ridge Rd, Winhall, VT 05155

    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 Ridge Rd, Winhall, VT 05155
  • /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 $629,023

    Last Listing Agent Mike England Michael England Real Estate

    3 Short Rd, Bondville, VT 05340
    • /40

      Est $965,353

      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

      • 29 Days On Market

  • /6

    $395,000

    $100K PRICE DROP
    • 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
  • /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 $554,977

    Last Listing Agent Carrie Mathews Winhall Real Estate

    22 Bromley Forest 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

      • 29 Days On Market

  • /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
  • /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 $831,204

    Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

    7 N Brookwood Rd, Winhall, VT 05340
    • /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

      • 10 Days On Market

  • /14

    $649,000

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

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

    Imagine Friday evening: you pull through the private gate, the tires of your car crunching over the paved lot, and you find that perfect spot right near the entrance. As you turn off the engine, a quiet stillness settles in. You won’t be reaching for those keys again until Monday.Welcome to your retreat at Village Watch. The ArrivalStep inside the dedicated mudroom, where there’s a place

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    792 Stratton Mtn Access Rd Unit 4310, 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
    • /15

      Est $429,014

      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

      • 13 Days On Market

  • /13

    $875,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    43 Middle Ridge Rd Unit 209, Winhall, VT 05155

    Beautiful corner three bedroom, two bath condominium in one Stratton Mountain's most desirable neighborhoods. Heated parking garage, with two assigned spaces. Locker room for ski storage. Heated year round pool, hot tubs, sauna for Rising Bear and Hearthstone. Private shuttle to skier drop off area, or walk directly across street. Excellent potential as a rental property. Sold fully furnished.

    John Sikes Stratton Real Estate

    43 Middle Ridge Rd Unit 209, Winhall, VT 05155
  • /39

    $875,000

    Sold May 21, 2026

    F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340

    • 4 Beds
    • 4 Baths
    • 2,673 Sq Ft
    • Built 1988

    Last Sold Summary

    • 2% Below List Price
    • $327/SF
    • 51 Days On Market

    Last Listing Agent Mike England Michael England Real Estate

    F2 Cobble Ridge Rd Unit F2, 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

      • 73 Days On Market

  • /12

    $95,000

    • Land
    • 1 Acre
    • $95,000 per Acre

    41 Moose Hollow Rd, Winhall, VT 05340

    Build your dream home on this ready-to-go 1-acre lot in the Green Mountains. Located on a private gravel road in Winhall, this mostly cleared parcel offers a gentle slope, power at the road, a nearby stream, and a state-issued 4-bedroom septic permit already in place. The setting provides a peaceful, natural feel while keeping you close to the best of Southern Vermont. Bromley Mountain is about

    Keith Nowak Four Seasons Sotheby's Int'l Realty

    41 Moose Hollow 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
    • /38

      Est $699,285

      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

      • 6 Days On Market

  • /40

    $475,000

    $35K PRICE DROP Under Contract
    • 4 Beds
    • 3 Baths
    • 1,680 Sq Ft

    7 Stratton West Rd Unit 7, Winhall, VT 05340

    This recently renovated 4/5 bedroom Stratton West home is located minutes to Stratton Resort for skiing, golf, and all your recreation activities. The new, custom-built kitchen offers an open layout with beautiful granite countertops. Front and back decks provides places to grill and relax on warm summer nights, or you can cozy up with the Harman pellet stove in the winter months. The first level

    Mike England Michael England Real Estate

    7 Stratton West Rd Unit 7, Winhall, VT 05340
  • /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 $2,205,251

    Last Listing Agent Christiane Carroccio TPW Real Estate

    19 Old Town Rd, Bondville, VT 05340
    • /40

      Est $855,019

      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

      • 8 Days On Market

  • /54

    $1,990,000

    • 6 Beds
    • 6.5 Baths
    • 5,896 Sq Ft

    27 Mountain View Rd, Winhall, VT 05360

    Direct views of Stratton Mountain set the stage for this exceptional post-and-beam residence, offering a rare combination of luxury living, entertaining space, and rental flexibility. Handcrafted timber framing creates warmth and character throughout, while four fireplaces including a gas fireplace in the primary suite enhance the home's mountain atmosphere. Designed for gathering, the lower

    Jamie Wylie Stratton Real Estate

    27 Mountain View Rd, Winhall, VT 05360
  • /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
    • /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

      • 4 Days On Market

  • /47

    $1,225,000

    • 4 Beds
    • 3 Baths
    • 3,357 Sq Ft

    153 High Meadow Rd, Winhall, VT 05340

    Located in Stratton Resort’s sought-after High Meadow community, this beautifully maintained and turnkey home offers the perfect blend of comfort, convenience, and mountain charm. Filled with natural light, the home features four bedrooms and three recently updated full baths, along with hardwood floors, cathedral ceilings, skylights, and a stunning floor-to-ceiling brick fireplace. Recent

    Britt Wohler

    153 High Meadow 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 $809,313

    Last Listing Agent Christina Dryden Berkshire Hathaway HomeServices Stratton Home

    6 Roundtree Rd, Winhall, VT 05340
    • /40

      Est $1,629,790

      Not Listed For Sale

      69 W Ridge Rd Unit 365, Winhall, VT 05340

      • 5 Beds
      • 5 Baths
      • 4,609 Sq Ft
      • Built 1971
      69 W Ridge Rd Unit 365, Winhall, VT 05340

      Last Sold Summary

      • 5 Days On Market

  • /39

    $798,000

    Under Contract
    • 3 Beds
    • 5 Baths
    • 3,100 Sq Ft

    52 High Meadow Rd Unit 11, Winhall, VT 05155

    Rarely available in Stratton’s sought-after Fairway Meadow neighborhood, this spacious 3-bedroom, 5-bath townhome offers the perfect balance of mountain retreat and year-round convenience. Ideally located adjacent to the Stratton Golf Course and just a short drive to the ski slopes and Village, this townhome is perfectly positioned to enjoy every season in Southern Vermont. The inviting interior

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    52 High Meadow Rd Unit 11, Winhall, VT 05155
  • /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 $871,583

    Last Listing Agent Carrie Mathews Winhall Real Estate

    5 Stratton Ridge Rd, Winhall, VT 05340

Showing Results 121 - 160, Page 4 of 18

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