2,306

Winhall, VT Homes

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  • /31

    $1,200,000

    • 1 Bath
    • 950 Sq Ft

    109 Winhall Hollow Rd, Winhall, VT 05340

    Experience the pinnacle of Green Mountain living on this extraordinary 23.5-acre property. Perfectly positioned to capture a stunning, direct-line-of-sight view of Stratton Mountain, this property is more than just a home—it is a private outdoor sanctuary meticulously designed by The Wadsworth Company for the modern adventurer. The centerpiece of the property is a striking, contemporary dwelling

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    109 Winhall Hollow Rd, Winhall, VT 05340
  • /22

    $445,000

    Sold Sep 16, 2025

    163 Vt Route 30, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,590 Sq Ft
    • Built 1970

    Last Sold Summary

    • 1% Below List Price
    • $280/SF
    • 13 Days On Market

    Current Estimated Value $442,030

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

    163 Vt Route 30, Winhall, VT 05340
    • /52

      Not Listed For Sale

      E11 Rock Ridge Rd, Winhall, VT 05155

      • 3 Beds
      • 3 Baths
      • 2,300 Sq Ft
      • Built 1986
      E11 Rock Ridge Rd, Winhall, VT 05155

      Last Sold Summary

      • 47 Days On Market

  • /38

    $625,000

    • 3 Beds
    • 2 Baths
    • 2,288 Sq Ft

    1 Beaver St, Bondville, VT 05340

    Ideally located between Manchester and the mountains, this home offers the perfect blend of convenience, comfort, and Vermont charm. Just 10 minutes to Stratton, 5 minutes to Bromley, and 12 minutes to Manchester, you’ll enjoy easy access to skiing, dining, shopping, and year-round recreation.Inside, the home features a spacious living room filled with natural light, creating a warm and

    Carrie Mathews Winhall Real Estate

    1 Beaver St, Bondville, VT 05340
  • /2

    $205,000

    Sold Sep 15, 2025

    24 Stratton Rd W, Winhall, VT 05340

    • 2 Beds
    • 1 Bath
    • 665 Sq Ft
    • Built 1970

    Last Sold Summary

    • $308/SF
    • 0 Days On Market

    Current Estimated Value $206,029

    Last Listing Agent Cheyanne Pugliese

    24 Stratton Rd W, Winhall, VT 05340
    • /39

      Not Listed For Sale

      5 Red Hickory Rd, Winhall, VT 05340

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

      Last Sold Summary

      • 24 Days On Market

  • /22

    $430,000

    • 5 Beds
    • 2 Baths
    • 1,664 Sq Ft

    13 Golden Triangle Rd, Winhall, VT 05340

    The ideal opportunity in a prime location, minutes from Stratton Mountain, Bromley Mountain, and the charming town of Manchester, this 5-bedroom, 2-bathroom home has what you need for your primary Vermont residence or a quiet place to getaway. The spacious living room and dining area is complimented by a wrap around porch. This home is low maintenance and setup well for those who want a

    Mike England Michael England Real Estate

    13 Golden Triangle Rd, Winhall, VT 05340
  • /53

    $775,000

    Sold Aug 13, 2025

    E12 Rock Ridge Rd, Winhall, VT 05155

    • 3 Beds
    • 3 Baths
    • 1,842 Sq Ft
    • Built 1986

    Last Sold Summary

    • 3% Below List Price
    • $421/SF
    • 7 Days On Market

    Last Listing Agent Cheyanne Pugliese

    E12 Rock Ridge Rd, Winhall, VT 05155
    • /55

      Est $878,901

      Not Listed For Sale

      45 Hilltop Rd, Winhall, VT 05340

      • 5 Beds
      • 4 Baths
      • 2,900 Sq Ft
      • Built 1996
      45 Hilltop Rd, Winhall, VT 05340

      Last Sold Summary

      • 7 Days On Market

  • /12

    $150,000

    $25K PRICE DROP
    • Land
    • 2.26 Acres
    • $66,372 per Acre

    0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340

    Welcome to the Stratton Gardens Community. Build your Vermont home on this 2+ acre parcel in Stratton Gardens. Ease of access right off the Stratton Mountain Access Road, and all the amenities of Stratton Gardens Association- highlights include-Private Shuttle Bus service to the Mountain, Road Maintenance, Plowing, Landscaping, and Trash removal.State Waste Water Permit in place for approved

    Tara van de Velde Four Seasons Sotheby's Int'l Realty

    0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340
  • /2

    $400,000

    Sold Mar 09, 2026

    97 N Branch Rd, Winhall, VT 05155

    • Land
    • 1.18 Acres
    • $338,983 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 29 Days On Market

    Last Listing Agent John Sikes Stratton Real Estate

    97 N Branch Rd, Winhall, VT 05155
    • /35

      Est $593,187

      Not Listed For Sale

      20 Deep Woods Cir, Winhall, VT 05255

      • 3 Beds
      • 2 Baths
      • 1,592 Sq Ft
      • Built 2005
      20 Deep Woods Cir, Winhall, VT 05255

      Last Sold Summary

      • 8 Days On Market

  • /41

    $950,000

    • 4 Beds
    • 3.5 Baths
    • 3,031 Sq Ft

    7 Roundtree Rd, Winhall, VT 05340

    Discover the perfect mountain retreat at 7 Roundtree Road, a contemporary and beautifully designed 4-bedroom home set on 1.37 private acres in one of Stratton’s most sought-after neighborhoods. Ideally located just a quick drive to the Base Lodge—or simply hop on the convenient shuttle for effortless access to the slopes—this property offers the best of Stratton living in every season.Step

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    7 Roundtree Rd, Winhall, VT 05340
  • /22

    $265,500

    Sold Jul 15, 2025

    18 Stratton Ridge Rd, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,332 Sq Ft
    • Built 1970

    Last Sold Summary

    • 16% Below List Price
    • $199/SF
    • 72 Days On Market

    Last Listing Agent Derek Greene Derek Greene

    18 Stratton Ridge Rd, Winhall, VT 05340
    • /30

      Not Listed For Sale

      20 Maple Beech Rd Unit 20, Winhall, VT 05340

      • 3 Beds
      • 3 Baths
      • 1,650 Sq Ft
      • Built 1984
      20 Maple Beech Rd Unit 20, Winhall, VT 05340

      Last Sold Summary

      • 4 Days On Market

  • /15

    $825,000

    • Land
    • 77.6 Acres
    • $10,631 per Acre

    0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340

    Large wooded parcel located in the heart of Southern Vermont’s ski country, just minutes from Stratton Mountain. This undeveloped Winhall property offers a rare opportunity for a variety of potential uses, from a private estate to recreational land or possible future development. The land consists primarily of wooded acreage with a gently rolling landscape and natural Vermont forest. Located on

    Trent Stephens Wohler Realty Group

    0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340
  • /46

    $1,270,000

    Sold Mar 20, 2026

    33 Forest Haunts Rd, Winhall, VT 05340

    • 4 Beds
    • 4 Baths
    • 4,640 Sq Ft
    • Built 1989

    Last Sold Summary

    • 15% Below List Price
    • $274/SF
    • 487 Days On Market

    Current Estimated Value $1,320,511

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

    33 Forest Haunts Rd, Winhall, VT 05340
    • /25

      Not Listed For Sale

      0 Cobble Ridge Rd Unit D2, Winhall, VT 05340

      • 4 Beds
      • 3 Baths
      • 2,317 Sq Ft
      • Built 1988
      0 Cobble Ridge Rd Unit D2, Winhall, VT 05340

      Last Sold Summary

      • 135 Days On Market

  • /60

    $1,395,000

    • 2 Beds
    • 3.5 Baths
    • 3,873 Sq Ft

    181 Route 11, Winhall, VT 05340

    Perched on 6.3 private acres with sweeping views of Mt. Equinox, this custom post-and-beam home offers a rare combination of craftsmanship, energy efficiency, and natural beauty. Bordering the Green Mountain National Forest on two sides and located just minutes from Manchester, Bromley, and Stratton, the property delivers a secluded mountain retreat without sacrificing convenience. Built in 2012,

    Jonathan Minerick

    181 Route 11, Winhall, VT 05340
  • /43

    $1,374,000

    Sold May 21, 2026

    12 Sunny Hill Rd, Manchester Center, VT 05255

    • 4 Beds
    • 3.5 Baths
    • 5,397 Sq Ft
    • Built 1976

    Last Sold Summary

    • 2% Below List Price
    • $255/SF
    • 50 Days On Market

    Current Estimated Value $793,543

    Last Listing Agent Carrie Mathews Winhall Real Estate

    12 Sunny Hill Rd, Manchester Center, VT 05255
    • /30

      Est $662,353

      Not Listed For Sale

      6 Golden Triangle Rd, Winhall, VT 05340

      • 3 Beds
      • 3 Baths
      • 1,680 Sq Ft
      • Built 2004
      6 Golden Triangle Rd, Winhall, VT 05340

      Last Sold Summary

      • 10 Days On Market

  • /27

    $609,000

    • 4 Beds
    • 3 Baths
    • 1,650 Sq Ft

    60 Hilltop Rd Unit 60, Winhall, VT 05340

    Turn-key Stratton retreat in one of the area’s most desirable year-round communities. This 4-bedroom, 3-bath Intervale townhome offers the perfect blend of comfort and convenience—just minutes to the slopes with seasonal shuttle service right from the community. The open-concept living area is ideal for gathering after a day on the mountain, while five mini-split systems provide efficient heating

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    60 Hilltop Rd Unit 60, Winhall, VT 05340
  • /35

    $870,000

    Sold May 13, 2026

    24 Sugarbush Dr, Jamaica, VT 05343

    • 5 Beds
    • 3 Baths
    • 2,897 Sq Ft
    • Built 1974

    Last Sold Summary

    • 2% Above List Price
    • $300/SF
    • 8 Days On Market

    Last Listing Agent Carrie Mathews Winhall Real Estate

    24 Sugarbush Dr, Jamaica, VT 05343
    • /32

      Not Listed For Sale

      1 Silver Birch Rd, Winhall, VT 05340

      • 3 Beds
      • 2 Baths
      • 1,215 Sq Ft
      • Built 1968
      1 Silver Birch Rd, Winhall, VT 05340

      Last Sold Summary

      • 61 Days On Market

  • /15

    $500,000

    • Land
    • 21.2 Acres
    • $23,585 per Acre

    56 Lower Taylor Hill Rd, Winhall, VT 05340

    Set along Lower Taylor Hill Road in Winhall, this 21.2 +/- acre offering captures the privacy, natural beauty, and four-season lifestyle that define Southern Vermont living. Rolling terrain, mature woodland, and natural clearings create an exceptional setting for a private Vermont retreat, with the potential for Bromley Mountain views depending on house placement and design.Supported by a

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    56 Lower Taylor Hill Rd, Winhall, VT 05340
  • /41

    $1,775,000

    Sold May 08, 2026

    43 Middle Ridge Rd Unit 416, Winhall, VT 05155

    • 4 Beds
    • 4 Baths
    • 2,401 Sq Ft
    • Built 2004

    Last Sold Summary

    • $739/SF
    • 2 Days On Market

    Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

    43 Middle Ridge Rd Unit 416, Winhall, VT 05155
    • /60

      Est $862,452

      Not Listed For Sale

      53 Stratton View Rd, Bondville, VT 05340

      • 4 Beds
      • 3.5 Baths
      • 3,772 Sq Ft
      • Built 1989
      53 Stratton View Rd, Bondville, VT 05340

      Last Sold Summary

      • 30 Days On Market

  • /55

    $950,000

    $45K PRICE DROP Under Contract
    • 5 Beds
    • 4.5 Baths
    • 2,321 Sq Ft

    24 N Branch Rd, Winhall, VT 05340

    Location says it all ! Stratton Quarter Mile neighborhood on Shuttle, just a short walk home from the Village. This exceptional renovation offers an expanded floor plan with a third level.Beautiful upscale baths with tile work and craftsmanship of the highest caliber. Wood floors throughout. Open gourmet kitchen makes for premier apres ski gatherings. With 5 bedrooms/4 baths and multiple ensuite-

    Kim Morgan-Wohler Wohler Realty Group

    24 N Branch Rd, Winhall, VT 05340
  • /32

    $350,000

    Sold Mar 20, 2026

    44 Lake Rd, Bondville, VT 05340

    • 5 Beds
    • 3 Baths
    • 2,303 Sq Ft
    • Built 1976

    Last Sold Summary

    • 22% Below List Price
    • $152/SF
    • 5 Days On Market

    Current Estimated Value $375,342

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

    44 Lake Rd, Bondville, VT 05340
    • /40

      Est $908,995

      Not Listed For Sale

      36 Road To Millbrook, Winhall, VT 05340

      • 4 Beds
      • 3.5 Baths
      • 3,119 Sq Ft
      • Built 1996
      36 Road To Millbrook, Winhall, VT 05340

      Last Sold Summary

      • 168 Days On Market

  • /39

    $495,000

    Under Contract
    • 4 Beds
    • 2 Baths
    • 1,824 Sq Ft

    140 Vermont 30, Winhall, VT 05340

    Quintessential Vermont charm meets modern comfort in this beautifully updated New England farmhouse just minutes from Stratton Mountain. Ideally located only 1 mile from the Stratton Mountain Access Road and just 1/10 mile to the VAST snowmobile trail, this 4-bedroom, 2-bath home offers the perfect four-season retreat. Rich with character, the home features exposed beams, warm hardwood floors,

    Carrie Mathews Winhall Real Estate

    140 Vermont 30, Winhall, VT 05340
  • /26

    $795,000

    Sold Aug 21, 2025

    5 Founders Hill Rd, Winhall, VT 05360

    • 3 Beds
    • 3 Baths
    • 1,624 Sq Ft
    • Built 1970

    Last Sold Summary

    • $490/SF
    • 0 Days On Market

    Last Listing Agent Jamie Wylie Stratton Real Estate

    5 Founders Hill Rd, Winhall, VT 05360
    • /14

      Not Listed For Sale

      00 Kendall Farm To Black Cherry Ridge Rd, Winhall, VT 05340

      00 Kendall Farm To Black Cherry Ridge Rd, Winhall, VT 05340

      Last Sold Summary

      • 120 Days On Market

  • /33

    $649,000

    • 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
  • /22

    $389,000

    Sold Feb 23, 2026

    2 Lower Stratton Valley Rd, Winhall, VT 05340

    • 4 Beds
    • 1.5 Baths
    • 1,344 Sq Ft
    • Built 1978

    Last Sold Summary

    • $289/SF
    • 26 Days On Market

    Current Estimated Value $385,018

    Last Listing Agent Mike Masters Four Seasons Sotheby's Int'l Realty

    2 Lower Stratton Valley Rd, Winhall, VT 05340
    • /11

      Not Listed For Sale

      E3 Nearing Rd, Winhall, VT 05340

      E3 Nearing Rd, Winhall, VT 05340

      Last Sold Summary

      • 212 Days On Market

  • /37

    $829,000

    $20K PRICE DROP 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
  • /49

    $705,000

    Sold Jan 06, 2026

    A6 Ridge Unit A6, Winhall, VT 05340

    • 4 Beds
    • 3 Baths
    • 2,118 Sq Ft
    • Built 1982

    Last Sold Summary

    • 12% Below List Price
    • $333/SF
    • 225 Days On Market

    Last Listing Agent Karin Hardy Berkshire Hathaway HomeServices Stratton Home

    A6 Ridge Unit A6, Winhall, VT 05340
    • /39

      Est $627,384

      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

      • 2 Days On Market

  • /38

    $4,999,000

    $2M PRICE DROP Under Contract
    • 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

Showing Results 81 - 120, Page 3 of 18

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