2,274

Winhall, VT Homes

Section Image
    • /39

      Est $596,142 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

      • 6% Above List Price
      • $370/SF
      • 2 Days On Market

      Last Sold Price $560,000

      Last Listing Agent Mike England Michael England Real Estate

  • /31

    $475,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,570 Sq Ft

    5 Byington Ln, Winhall, VT 05340

    Built in the style of an Austrian ski chalet, this impeccable property is the perfect opportunity to own a mountain-modern Vermont home. Fully renovated and lovingly maintained, this chalet is stylish and functional for both entertaining and cozying up. With wifi, landscaping, snow removal, and trash managed by the association and included in the community's reasonable dues, ownership is turnkey.

    Jamie Luke TPW Real Estate

    5 Byington Ln, 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
    • /33

      Est $575,415 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

      • 18% Above List Price
      • $204/SF
      • 9 Days On Market

      Last Sold Price $489,000

      Last Listing Agent Carrie Mathews Winhall Real Estate

  • /37

    $849,000

    • 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
  • /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 $2,227,362

    Last Listing Agent Christiane Carroccio TPW Real Estate

    19 Old Town 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

      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
  • /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
    • /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

      Last Listing Agent Cheyanne Pugliese

  • /50

    $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
  • /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 $823,255

    Last Listing Agent Christina Dryden Berkshire Hathaway HomeServices Stratton Home

    6 Roundtree 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

      Last Listing Agent Carrie Mathews Winhall Real Estate

  • /5

    $440,000

    • Land
    • 5.54 Acres
    • $79,422 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
  • /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 $837,191

    Last Listing Agent Carrie Mathews Winhall Real Estate

    5 Stratton Ridge Rd, Winhall, VT 05340
    • /40

      Est $1,024,758 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

      • 2% Below List Price
      • $565/SF
      • 29 Days On Market

      Last Sold Price $1,050,000

      Last Listing Agent Christiane Carroccio TPW Real Estate

  • /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
  • /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 $1,088,597

    Last Listing Agent Carrie Mathews Winhall Real Estate

    6 Chad Cir, Winhall, 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

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

  • /6

    $470,000

    • Land
    • 6.93 Acres
    • $67,821 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 $323,294

    Last Listing Agent Cheyanne Pugliese

    19 Winhall Condo Rd Unit 5, 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

      • $265/SF
      • 10 Days On Market

      Last Sold Price $322,500

      Last Listing Agent Helen Nault

  • /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 $715,818

    Last Listing Agent Jamie Wylie Stratton Real Estate

    58 Todd Hill Rd, Bondville, VT 05340
    • /15

      Est $431,758 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

      • 4% Above List Price
      • $474/SF
      • 13 Days On Market

      Last Sold Price $415,000

      Last Listing Agent Christine Chovan

  • /12

    $95,000 Under Contract

    • 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
  • /51

    $1,300,000 Sold Aug 25, 2025

    33 Jamie Ln, Bondville, VT 05340

    • 4 Beds
    • 4.5 Baths
    • 4,541 Sq Ft
    • Built 2004

    Last Sold Summary

    • 19% Below List Price
    • $286/SF
    • 7 Days On Market

    Current Estimated Value $1,382,382

    Last Listing Agent Cynthia Mitrani Berkshire Hathaway HomeServices Stratton Home

    33 Jamie Ln, Bondville, 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

      Last Listing Agent Stephen Coombs Stratton Real Estate

  • /35

    $650,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,370 Sq Ft

    5 Linscott Rd, Jamaica, VT 05343

    PRICE ADJUSTMENT to $650,000.This irresistible renovated Forest Farms contemporary with 3 bedrooms and 2 and a half baths has an inviting ambiance as well as appealing floor plan flow. Past the foyer with half bath is the open living concept with white oak hardwood floors. The glow and warmth of the raised hearth stone fireplace in the living area is shared from windowed dining area to bright

    Diana Stugger Four Seasons Sotheby's Int'l Realty

    5 Linscott Rd, Jamaica, VT 05343
  • /58

    $600,000 Sold Feb 17, 2026

    11 Pond View Rd, Winhall, VT 05340

    • 3 Beds
    • 3 Baths
    • 1,650 Sq Ft
    • Built 1985

    Last Sold Summary

    • 5% Below List Price
    • $364/SF
    • 270 Days On Market

    Current Estimated Value $607,182

    Last Listing Agent Terry Hill Berkshire Hathaway HomeServices Stratton Home

    11 Pond View Rd, Winhall, VT 05340
    • /38

      Est $694,469 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

      Last Listing Agent Jamie Luke TPW Real Estate

  • /49

    $510,000

    • 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
  • /55

    $2,150,000 Sold Feb 12, 2026

    16 Hunter Ridge Rd, Bondville, VT 05340

    • 4 Beds
    • 4.5 Baths
    • 5,000 Sq Ft
    • Built 2011

    Last Sold Summary

    • 3% Below List Price
    • $430/SF
    • 165 Days On Market

    Current Estimated Value $2,035,736

    Last Listing Agent Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    16 Hunter Ridge Rd, Bondville, VT 05340
    • /40

      Est $872,478 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

      • 2% Above List Price
      • $424/SF
      • 8 Days On Market

      Last Sold Price $855,000

      Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

  • /9

    $65,000 Under Contract

    • Land
    • 0.74 Acre
    • $87,838 per Acre

    0 Stratton View Rd Unit 25, Winhall, VT 05340

    Stratton View Rd Lot # 58 , .74 +- acres wooded parcel. Just 3 minutes to Stratton access road. Minutes to the snow making pond, great for walking and a dip in. the summer. There are 3 ski resorts with in 15 minutes as well as Manchester for shopping and dining. Addition Lot MLS #5036984 available. Own your piece of Vermont.

    Mike England Michael England Real Estate

    0 Stratton View Rd Unit 25, Winhall, VT 05340
  • /33

    $951,014 Sold Oct 24, 2025

    14 Mountain Haunts, Winhall, VT 05340

    • 5 Beds
    • 3 Baths
    • 3,238 Sq Ft
    • Built 1987

    Last Sold Summary

    • 9% Above List Price
    • $294/SF
    • 4 Days On Market

    Current Estimated Value $923,582

    Last Listing Agent Carrie Mathews Winhall Real Estate

    14 Mountain Haunts, 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

      Last Listing Agent Carrie Mathews Winhall Real Estate

  • /33

    $775,000

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

    0 Maple Ridge Rd Unit B-2, Winhall, VT 05340

    Beautifully updated Piper Ridge townhouse just steps from the private sports center and offering weekend/holiday shuttle service to Stratton’s lifts in winter. This light-filled home features an updated kitchen and baths, gleaming hardwood floors, and elegant tilework throughout. The one-car garage has been thoughtfully converted into a spacious ski room plus a large storage or owner’s

    Carrie Mathews Winhall Real Estate

    0 Maple Ridge Rd Unit B-2, Winhall, VT 05340
  • /43

    $1,603,000 Sold Jan 28, 2026

    143 Stratton Mountain Access Rd, Winhall, VT 05340

    • 5 Beds
    • 4.5 Baths
    • 3,688 Sq Ft
    • Built 2025

    Last Sold Summary

    • 5% Below List Price
    • $435/SF
    • 103 Days On Market

    Current Estimated Value $1,175,078

    Last Listing Agent Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    143 Stratton Mountain Access Rd, Winhall, VT 05340
    • /40

      Est $1,619,109 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

      • 3% Above List Price
      • $342/SF
      • 5 Days On Market

      Last Sold Price $1,575,000

      Last Listing Agent Diana Stugger Four Seasons Sotheby's Int'l Realty

Showing Results 121 - 160, Page 4 of 18

How to Buy a Home How to Finance a Home How to Sell a Home