2,306

Winhall, VT Homes

Section Image
    • /40

      Est $891,217

      Not Listed For Sale

      34 Raspberry Hill Rd, Winhall, VT 05340

      • 4 Beds
      • 3 Baths
      • 2,872 Sq Ft
      • Built 1975
      34 Raspberry Hill Rd, Winhall, VT 05340

      Last Sold Summary

      • 5 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
  • /33

    $485,000

    Sold Apr 20, 2026

    3 Strattonwald Rd, Winhall, VT 05340

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft
    • Built 1963

    Last Sold Summary

    • 8% Below List Price
    • $361/SF
    • 276 Days On Market

    Current Estimated Value $474,138

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

    3 Strattonwald Rd, Winhall, VT 05340
    • /25

      Est $355,565

      Not Listed For Sale

      84 Lower Taylor Hill Rd, Winhall, VT 05340

      • 4 Beds
      • Built 1900
      84 Lower Taylor Hill Rd, Winhall, VT 05340

      Last Sold Summary

      • 4 Days On Market

  • /38

    $375,000

    • Land
    • 1.23 Acres
    • $304,878 per Acre

    0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340

    Exceptional offering. This premier parcel defines phase II of Ravenwood, an enclave of distinctive and premier mountain residences. This notable site offers extraordinary mountain views, direct access from Winhall Hollow Road and still enjoys all the benefits and amenities of The Ravenwood Neighborhood Association. Combining, privacy, natural beauty and convenience, this well-established

    Kim Morgan-Wohler Wohler Realty Group

    0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340
  • /35

    $707,500

    Sold May 01, 2026

    9 Old Route 30, Winhall, VT 05340

    • 4 Beds
    • 2 Baths
    • 2,715 Sq Ft
    • Built 1948

    Last Sold Summary

    • 2% Above List Price
    • $261/SF
    • 4 Days On Market

    Current Estimated Value $649,092

    Last Listing Agent Carrie Mathews Winhall Real Estate

    9 Old Route 30, Winhall, VT 05340
    • /36

      Est $735,717

      Not Listed For Sale

      11 Todd Hill Rd, Winhall, VT 05340

      • 3 Beds
      • 2 Baths
      • 1,800 Sq Ft
      • Built 1973
      11 Todd Hill Rd, Winhall, VT 05340

      Last Sold Summary

      • 30 Days On Market

  • /33

    $1,399,999

    • 6 Beds
    • 4 Baths
    • 3,800 Sq Ft

    121 High Meadow Rd, Winhall, VT 05340

    Bring the whole household to this great place with lots of room for fun. A 6-bedroom, 4-bathroom Adirondack-style Ski Chalet located in a neighborhood just minutes from the Stratton Mountain Ski Resort, with free door-to-mountain shuttle service on select days. Amenities include four (4) fireplaces, best hot-tub on the market, an in home gym, electric sauna, pool table, SuperChexx Bubble Hockey

    Ralph Harvey Listwithfreedom.com

    121 High Meadow Rd, Winhall, VT 05340
  • /41

    $1,150,000

    Sold Jul 25, 2025

    35 Old Ridge Rd, Winhall, VT 05155

    • 4 Beds
    • 5.5 Baths
    • 4,826 Sq Ft
    • Built 1997

    Last Sold Summary

    • 38% Below List Price
    • $238/SF
    • 369 Days On Market

    Last Listing Agent Mike England Michael England Real Estate

    35 Old Ridge Rd, Winhall, VT 05155
    • /40

      Est $801,854

      Not Listed For Sale

      40 Loop Rd, Winhall, VT 05340

      • 3 Beds
      • 3 Baths
      • 2,196 Sq Ft
      • Built 2006
      40 Loop Rd, Winhall, VT 05340

      Last Sold Summary

      • 5 Days On Market

  • /4

    $400,000

    • Land
    • 8.01 Acres
    • $49,938 per Acre

    248 French Hollow Rd, Winhall, VT 05340

    Legacy family property, held until now for its premier location and extraordinary views of Stratton Mountain. Acreage offers a building site that is privately situated off the road with a 4 bedroom state septic permit and ready for the mountain home you have been hoping to create! A beautiful parcel with level plateau for building and a moderate slope down to its lower boundary. Surrounded by a

    Kim Morgan-Wohler Wohler Realty Group

    248 French Hollow Rd, Winhall, VT 05340
  • /37

    $777,500

    Sold Jun 01, 2026

    34 Mountain View Rd, Winhall, VT 05360

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft
    • Built 1980

    Last Sold Summary

    • 2% Below List Price
    • $311/SF
    • 15 Days On Market

    Last Listing Agent Jason Saphire www.HomeZu.com

    34 Mountain View Rd, Winhall, VT 05360
    • /39

      Est $768,556

      Not Listed For Sale

      28 W Branch Rd, Winhall, VT 05340

      • 4 Beds
      • 3.5 Baths
      • 2,300 Sq Ft
      • Built 1989
      28 W Branch Rd, Winhall, VT 05340

      Last Sold Summary

      • 8 Days On Market

  • /26

    $850,000

    • 3 Beds
    • 3 Baths
    • 2,598 Sq Ft

    46 Ridge Rd Unit C-4, Winhall, VT 05340

    Experience four-season Vermont living in this beautifully appointed end-unit townhome in the highly sought-after Highgate neighborhood at Piper Ridge, one of Stratton Mountain's premier resort communities. Ideally located in Winhall, Vermont, just minutes from Stratton Mountain Resort, this spacious 3-bedroom, 3-bath residence offers exceptional privacy, abundant natural light, The thoughtfully

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    46 Ridge Rd Unit C-4, Winhall, VT 05340
  • /43

    $755,000

    Sold Nov 14, 2025

    43 Hilltop Rd, Winhall, VT 05340

    • 4 Beds
    • 4 Baths
    • 3,020 Sq Ft
    • Built 1988

    Last Sold Summary

    • 2% Above List Price
    • $250/SF
    • 0 Days On Market

    Current Estimated Value $746,856

    Last Listing Agent Daniel Preston KW Vermont Woodstock

    43 Hilltop Rd, Winhall, VT 05340
    • /38

      Not Listed For Sale

      14 Middle Ridge Rd Unit 19A, Winhall, VT 05155

      • 4 Beds
      • 3.5 Baths
      • 2,160 Sq Ft
      • Built 1986
      14 Middle Ridge Rd Unit 19A, Winhall, VT 05155

      Last Sold Summary

      • 9 Days On Market

  • /59

    $899,000

    Under Contract
    • 5 Beds
    • 3.5 Baths
    • 4,000 Sq Ft

    178 High Meadow Rd, Winhall, VT 05340

    POSTPONED OPENHOUSE Spacious 4,000± sq. ft. contemporary home located in a sought-after ski resort community with convenient winter shuttle bus access to the slopes. Designed for both entertaining and everyday comfort, this property features an open-concept floor plan, abundant natural light, and generous living spaces throughout. The inviting family recreation room with bar offers the perfect

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    178 High Meadow Rd, Winhall, VT 05340
  • /59

    $1,082,500

    Sold Aug 29, 2025

    4 Garden Loop Rd, Winhall, VT 05340

    • 3 Beds
    • 3.5 Baths
    • 4,054 Sq Ft
    • Built 2005

    Last Sold Summary

    • 10% Below List Price
    • $267/SF
    • 45 Days On Market

    Current Estimated Value $1,138,416

    Last Listing Agent Lucy Ferrada Heney Realtors - Element Real Estate (Montpelier)

    4 Garden Loop Rd, Winhall, VT 05340
    • /60

      Est $1,980,483

      Not Listed For Sale

      18 Rocky Dell Rd, Winhall, VT 05340

      • 7 Beds
      • 5.5 Baths
      • 6,195 Sq Ft
      • Built 2007
      18 Rocky Dell Rd, Winhall, VT 05340

      Last Sold Summary

      • 246 Days On Market

  • /60

    $695,000

    $55K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    57 Pearl Buck Dr, Bondville, VT 05340

    WAKE UP TO UNPRECEDENTED MOUNTAIN VIEWS once called Terra Bella with ownership over four decades and now this can be the Winhall/Stratton residence you have been searching for. From the moment you drive in you are captivated with incredible scenery off prestigious Pearl Buck Drive. Offered on 3.5 acres.The main level boasts newly refinished oak floors, two bedrooms, a den or living area with

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    57 Pearl Buck Dr, Bondville, VT 05340
  • /33

    $740,000

    Sold Jan 02, 2026

    G12 Cobble Ridge Rd, Winhall, VT 05340

    • 4 Beds
    • 4 Baths
    • 2,764 Sq Ft
    • Built 1985

    Last Sold Summary

    • 5% Below List Price
    • $268/SF
    • 1 Day On Market

    Current Estimated Value $770,333

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

    G12 Cobble Ridge Rd, Winhall, VT 05340
    • /21

      Not Listed For Sale

      38 Quarter Mile Rd, Winhall, VT 05360

      • 4 Beds
      • 4 Baths
      • 1,940 Sq Ft
      • Built 1970
      38 Quarter Mile Rd, Winhall, VT 05360

      Last Sold Summary

      • 9 Days On Market

  • /35

    $799,000

    Under Contract
    • 4 Beds
    • 3.5 Baths
    • 3,078 Sq Ft

    63 Raspberry Hill Rd, Winhall, VT 05340

    Spacious and light-filled four-bedroom home ideally located in desirable Strattonwald, offering both winter and summer enjoyment in a private, peaceful setting. Enjoy convenient access to the Stratton winter shuttle, as well as summer amenities including a private pond and tennis courts. The home features generous living spaces perfect for gathering and entertaining, including a cozy fireplace

    Carrie Mathews Winhall Real Estate

    63 Raspberry Hill Rd, Winhall, VT 05340
  • /8

    $50,000

    Sold Apr 15, 2026

    0 Stratton View Rd Unit 26, Winhall, VT 05340

    • Land
    • 1.02 Acres
    • $49,020 per Acre

    Last Sold Summary

    • 23% Below List Price
    • 218 Days On Market

    Last Listing Agent Mike England Michael England Real Estate

    0 Stratton View Rd Unit 26, Winhall, VT 05340
    • /40

      Est $1,730,237

      Not Listed For Sale

      82 High Meadow Rd, Winhall, VT 05340

      • 6 Beds
      • 5.5 Baths
      • 4,551 Sq Ft
      • Built 2002
      82 High Meadow Rd, Winhall, VT 05340

      Last Sold Summary

      • 126 Days On Market

  • /32

    $449,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 1,460 Sq Ft

    32 Aspen Ln, Winhall, VT 05340

    A Sanctuary for Every Season:Picture the moment you turn off the main road and onto tree-lined Aspen Lane. The frantic pace of the week instantly drops away as you pull into your driveway. Tucked into a lush, wooded lot, this four-bedroom chalet is designed for those who live for the outdoors. Whether you’re here to chase the morning light on the slopes of nearby Stratton Resort or to spend a

    Robin Apps Four Seasons Sotheby's Int'l Realty

    32 Aspen Ln, Winhall, VT 05340
  • /58

    $975,000

    Sold Nov 27, 2025

    20 Jamie Ln, Winhall, VT 05340

    • 5 Beds
    • 3.5 Baths
    • 3,500 Sq Ft
    • Built 1987

    Last Sold Summary

    • $279/SF
    • 38 Days On Market

    Current Estimated Value $956,981

    Last Listing Agent David Powers 42 North LP

    20 Jamie Ln, Winhall, VT 05340
    • /24

      Est $517,439

      Not Listed For Sale

      13 Lower Taylor Hill Rd, Winhall, VT 05340

      • 3 Beds
      • 2.5 Baths
      • 1,716 Sq Ft
      • Built 1967
      13 Lower Taylor Hill Rd, Winhall, VT 05340

      Last Sold Summary

      • 26 Days On Market

  • /37

    $575,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft

    30 Upper Woods and Water Rd, Winhall, VT 05340

    Perched to capture breathtaking long-range views, this striking ski home offers an unforgettable vantage point of Magic Mountain and Stratton, with Bromley visible to the northwest—a daily reminder that some of Southern Vermont’s best skiing and outdoor adventure are just minutes away. With its cool, modern vibe and classic alpine character, the home perfectly blends style, comfort, and mountain

    Carrie Mathews Winhall Real Estate

    30 Upper Woods and Water Rd, Winhall, VT 05340
  • /30

    $717,500

    Sold Feb 13, 2026

    32 Cobble Ridge Rd Unit D10, Winhall, VT 05155

    • 3 Beds
    • 3 Baths
    • 2,317 Sq Ft
    • Built 1985

    Last Sold Summary

    • 2% Below List Price
    • $310/SF
    • 60 Days On Market

    Last Listing Agent Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

    32 Cobble Ridge Rd Unit D10, Winhall, VT 05155
    • /31

      Not Listed For Sale

      71 Todd Hill Rd, Jamaica, VT 05343

      • 5 Beds
      • 5.5 Baths
      • 3,624 Sq Ft
      • Built 2006
      71 Todd Hill Rd, Jamaica, VT 05343

      Last Sold Summary

      • 4 Days On Market

  • /32

    $1,275,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,814 Sq Ft

    19 Maple Hill Rd, Winhall, VT 05340

    Beautifully renovated in 2023, this 4-bedroom, 2-1/2 bathroom contemporary sits on 1.47 wooded acres with a sweeping circular driveway and genuine privacy — while still being on the Stratton shuttle route and just minutes from the base lodge on foot. The interior renovation was done right. Radiant heat floors run through the living room and kitchen, with two wood-burning fireplaces anchoring the

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    19 Maple Hill Rd, Winhall, VT 05340
  • /40

    $1,000,000

    Sold Feb 24, 2026

    19 Roundtree Rd, Bondville, VT 05340

    • 4 Beds
    • 2.5 Baths
    • 3,086 Sq Ft
    • Built 1978

    Last Sold Summary

    • 2% Below List Price
    • $324/SF
    • 80 Days On Market

    Current Estimated Value $1,006,033

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    19 Roundtree Rd, Bondville, VT 05340
    • /21

      Not Listed For Sale

      61 Birch Hill Rd Unit 6, Winhall, VT 05340

      • 3 Beds
      • 2 Baths
      • 1,215 Sq Ft
      • Built 1968
      61 Birch Hill Rd Unit 6, Winhall, VT 05340

      Last Sold Summary

      • 42 Days On Market

  • /5

    $374,900

    • Land
    • 2.31 Acres
    • $162,294 per Acre

    0 Wall St, Winhall, VT 05340

    Offered as a set, this property presents a rare opportunity to own two separately deeded parcels in a location that is only minutes from Stratton Mountain yet worlds away from the bustle of the resort. Totaling 2.31 acres, this land is situated high on River Road where neighboring homes enjoy spectacular views of Stratton. The engineering has already been completed, with each lot having a

    Cheyanne Pugliese

    0 Wall St, Winhall, VT 05340
  • /44

    $702,000

    Sold Oct 24, 2025

    86 Benson Fuller Dr, Bondville, VT 05340

    • 4 Beds
    • 2 Baths
    • 2,040 Sq Ft
    • Built 1983

    Last Sold Summary

    • 6% Below List Price
    • $344/SF
    • 42 Days On Market

    Current Estimated Value $688,047

    Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    86 Benson Fuller Dr, Bondville, VT 05340
    • /10

      Not Listed For Sale

      Lot 44 Moose Hollow Rd, Winhall, VT 05340

      Lot 44 Moose Hollow Rd, Winhall, VT 05340

      Last Sold Summary

      • 114 Days On Market

  • /12

    $299,999

    • Land
    • 10.05 Acres
    • $29,851 per Acre

    00 Garden Loop Rd, Winhall, VT 05340

    The largest remaining vacant lot on the Stratton Mountain access road. Ten acres deeded for one magnificent home. The lot is wooded with some clearing on the east side. There's a roughed-in driveway here too, making it the best spot for construction. In the center of the property is a small pond--about a tenth of an acre--and west of that a scenic perennial creek winds its way downhill along the

    David White OwnerEntry.com

    00 Garden Loop Rd, Winhall, VT 05340
  • /20

    $500,000

    Sold Nov 26, 2025

    374 Winhall Hollow Rd, Winhall, VT 05340

    • 4 Beds
    • 3 Baths
    • 1,920 Sq Ft
    • Built 1986

    Last Sold Summary

    • 1% Above List Price
    • $260/SF
    • 3 Days On Market

    Current Estimated Value $495,313

    Last Listing Agent Annette Gallo Real Broker LLC

    374 Winhall Hollow Rd, Winhall, VT 05340
    • /30

      Not Listed For Sale

      21 Stratton Ridge Rd, Winhall, VT 05340

      • 3 Beds
      • 1.5 Baths
      • 1,088 Sq Ft
      • Built 1970
      21 Stratton Ridge Rd, Winhall, VT 05340

      Last Sold Summary

      • 115 Days On Market

Showing Results 41 - 80, Page 2 of 18

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