2,288

Winhall, VT Homes

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    • /31

      Est $564,935 Not Listed For Sale

      22 Little Brook Rd, Winhall, VT 05340

      • 3 Beds
      • 2 Baths
      • 1,896 Sq Ft
      • Built 2004
      22 Little Brook Rd, Winhall, VT 05340

      Last Sold Summary

      • 15% Above List Price
      • $258/SF
      • 10 Days On Market
      • Last Sold Price $490,000
      • Sep 06, 2024

      Last Listing Agent TG Glazer Winhall Real Estate

  • /11

    $2,425,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 4,536 Sq Ft

    6 Stone Lodge Rd, Winhall, VT 05340

    SHOWINGS BEGIN at Thursday February 12. Premier New Construction, offering 4500+ SF of luxury living on three levels, perched on 2.5 acres to maximize panoramic mountain and Bromley views. Just minutes to the Stratton Resort Base Lodge, this exceptional 4 bedroom/3.5 bath floor plan combines contemporary design, craftsmanship of the highest caliber and energy efficiency.Thoughtfully designed for

    Kim Morgan-Wohler Wohler Realty Group

    6 Stone Lodge Rd, 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 $491,724

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

    3 Strattonwald Rd, Winhall, VT 05340
    • /40

      Est $887,330 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

      • 10% Above List Price
      • $282/SF
      • 5 Days On Market
      • Last Sold Price $810,000
      • May 14, 2024

      Last Listing Agent Jamie Luke TPW Real Estate

  • /38

    $949,000

    • 4 Beds
    • 3 Baths
    • 3,252 Sq Ft

    E1 Rock Ridge Rd, Winhall, VT 05155

    Ideally situated near the renowned Stratton Mountain Resort and offering convenient shuttle service to the slopes, this spacious four-bedroom, three-bath ski condo is thoughtfully designed for year-round enjoyment. A true retreat for outdoor enthusiasts, the home provides effortless access to world-class skiing in the winter and outstanding hiking and mountain biking throughout the warmer months.

    Christine Chovan

    E1 Rock Ridge Rd, Winhall, VT 05155
  • /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 $644,570

    Last Listing Agent Carrie Mathews Winhall Real Estate

    9 Old Route 30, Winhall, VT 05340
    • /25

      Est $356,238 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

      • 53% Above List Price
      • $122/SF
      • 4 Days On Market
      • Last Sold Price $233,000
      • Dec 02, 2024

      Last Listing Agent Julie Lowe Lowe's Real Estate, LLC

  • /2

    $125,000

    • Land
    • 1.45 Acres
    • $86,207 per Acre

    L/O River Rd, Winhall, VT 05340

    This 1.45+/- acre building lot offers a rare combination of privacy, recreation, and convenience. An approved Vermont wastewater permit for a 3-bedroom single-family home is already in place, streamlining the path toward building a year-round residence or mountain getaway. The property is located just one mile from the base of the Stratton Access Road and only twenty minutes from Manchester’s

    Cheyanne Pugliese

    L/O River 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
    • /15

      Est $497,503 Not Listed For Sale

      6 Old Snow Valley Rd, Winhall, VT 05340

      • 2 Beds
      • 2 Baths
      • 1,416 Sq Ft
      • Built 1957
      6 Old Snow Valley Rd, Winhall, VT 05340

      Last Sold Summary

      • 96% Above List Price
      • $179/SF
      • 4 Days On Market
      • Last Sold Price $254,000
      • May 04, 2023

      Last Listing Agent Joseph Cajzer Josiah Allen Real Estate, Inc.

  • /55

    $975,000 Under Contract

    • 4 Beds
    • 4 Baths
    • 4,184 Sq Ft

    520 Moose Hollow Rd, Winhall, VT 05340

    This custom-built contemporary home was designed with large gatherings of family and friends in mind, offering a spacious layout and plenty of room to relax and entertain. You can’t beat the location - just minutes to Manchester, Bromley, and Stratton, and nestled in the heart of year-round recreation. The private setting has views of Bromley’s trails and is bordered by the National Forest. This

    Karin Hardy Berkshire Hathaway HomeServices Stratton Home

    520 Moose Hollow Rd, 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 $770,723

    Last Listing Agent Daniel Preston KW Vermont Woodstock

    43 Hilltop Rd, Winhall, VT 05340
    • /39

      Est $1,231,265 Not Listed For Sale

      19 Maple Hill Rd, Winhall, VT 05340

      • 3 Beds
      • 2.5 Baths
      • 2,814 Sq Ft
      • Built 1978
      19 Maple Hill Rd, Winhall, VT 05340

      Last Sold Summary

      • 1% Above List Price
      • $435/SF
      • 6 Days On Market
      • Last Sold Price $1,225,000
      • Jul 11, 2023

      Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

  • /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
  • /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 $1,103,341

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

    4 Garden Loop Rd, Winhall, VT 05340
    • /36

      Est $742,606 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

      • 2% Above List Price
      • $403/SF
      • 30 Days On Market
      • Last Sold Price $725,000
      • Jan 03, 2025

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

  • /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
  • /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 $728,333

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

    G12 Cobble Ridge Rd, Winhall, VT 05340
    • /40

      Est $801,412 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

      • $365/SF
      • 5 Days On Market
      • Last Sold Price $802,000
      • Apr 26, 2024

      Last Listing Agent Terry Hill Berkshire Hathaway HomeServices Stratton Home

  • /37

    $795,000 Pending

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

    34 Mountain View Rd, Winhall, VT 05360

    Stratton Chalet with INCREDIBLE Mountain Views! Recently renovated this VT mountain retreat is the perfect place to enjoy all seasons in Southern VT. Enjoy the majestic views of the summit from your hot tub and firepit all year long. The interior layout is wonderful for larger groups to gather with an expansive open entertainment area on the ground level including the kitchen, dining and living

    Jason Saphire www.HomeZu.com

    34 Mountain View Rd, Winhall, VT 05360
  • /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 $551,219 Not Listed For Sale

      381 Winhall Hollow Rd, Bondville, VT 05340

      • 5 Beds
      • 4 Baths
      • 3,024 Sq Ft
      • Built 1970
      381 Winhall Hollow Rd, Bondville, VT 05340

      Last Sold Summary

      • 38% Above List Price
      • $132/SF
      • 10 Days On Market
      • Last Sold Price $399,000
      • May 17, 2023

      Last Listing Agent Carrie Mathews Winhall Real Estate

  • /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
  • /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 $980,115

    Last Listing Agent David Powers 42 North LP

    20 Jamie Ln, Winhall, VT 05340
    • /39

      Est $770,429 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

      • 51% Below List Price
      • $678/SF
      • 8 Days On Market
      • Last Sold Price $1,560,000
      • Jun 23, 2023

      Last Listing Agent Jessica Marullo TPW Real Estate

  • /13

    $475,000

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

    10 Byington Unit F1, Winhall, VT 05340

    The first showings will be at the open house 3/8/26 from 2-4 pm.Welcome to your Vermont mountain retreat in the sought-after Winhall Acres community. This charming 3-bedroom plus loft, 2-bath condominium chalet offers the perfect blend of comfort, convenience, and year-round adventure.The home features a smart and inviting layout designed for both relaxing and entertaining. Three

    Carrie Mathews Winhall Real Estate

    10 Byington Unit F1, 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
    • /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

      • $463/SF
      • 9 Days On Market
      • Last Sold Price $1,000,000
      • Jun 22, 2023

      Last Listing Agent MaryKate Grey Stratton Real Estate

  • /50

    $750,000

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    57 Pearl Buck Dr Unit 33, 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 Unit 33, Bondville, VT 05340
  • /29

    $750,000 Sold May 12, 2025

    12 Jamie Ln, Jamaica, VT 05343

    • 4 Beds
    • 3.5 Baths
    • 3,084 Sq Ft
    • Built 2003

    Last Sold Summary

    • 6% Below List Price
    • $243/SF
    • 82 Days On Market

    Last Listing Agent Kevin Moran Four Seasons Sotheby's Int'l Realty

    12 Jamie Ln, Jamaica, VT 05343
    • /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

      • $389/SF
      • 9 Days On Market
      • Last Sold Price $755,000
      • Oct 27, 2023

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

  • /35

    $849,000 Under Contract

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

    24 Sugarbush Dr, Jamaica, VT 05343

    Nestled in the highly sought-after Forest Farms neighborhood on Stratton Mountain, this beautifully updated 5-bedroom, 3-bath mountain retreat on Sugarbush Drive offers the perfect blend of comfort, style, and breathtaking natural beauty. The home features an open-concept living space designed to showcase the stunning surroundings, highlighted by a dramatic wall of glass that frames gorgeous

    Carrie Mathews Winhall Real Estate

    24 Sugarbush Dr, Jamaica, VT 05343
  • /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 $1,013,886

    Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

    19 Roundtree Rd, Bondville, VT 05340
    • /40

      Est $1,674,297 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

      • 4% Above List Price
      • $355/SF
      • 126 Days On Market
      • Last Sold Price $1,615,000
      • Jul 31, 2024

      Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

  • /38

    $860,000

    • 4 Beds
    • 3.5 Baths
    • 4,104 Sq Ft

    25 Benson Fuller Dr, Jamaica, VT 05343

    Mountain paradise awaits in this magnificent 5,000 sq ft Winhall retreat! Perched on a private acre with breathtaking, panoramic mountain views, this 4-bedroom, 3.5-bath home is an entertainer's dream and a serene escape. Step inside to discover a grand living room, a cozy family room, and a luxurious primary ensuite bedroom, each featuring a crackling wood-burning fireplace, perfect for chilly

    Robin Apps Four Seasons Sotheby's Int'l Realty

    25 Benson Fuller Dr, Jamaica, VT 05343
  • /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 $698,335

    Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    86 Benson Fuller Dr, Bondville, VT 05340
    • /24

      Est $469,866 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

      • 9% Above List Price
      • $251/SF
      • 26 Days On Market
      • Last Sold Price $430,000
      • Mar 26, 2025

      Last Listing Agent Carrie Mathews Winhall Real Estate

  • /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
  • /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 $510,861

    Last Listing Agent Annette Gallo Real Broker LLC

    374 Winhall Hollow Rd, Winhall, VT 05340
    • /40

      Not Listed For Sale

      13 Old Ridge Rd, Winhall, VT 05155

      • 4 Beds
      • 4.5 Baths
      • 2,327 Sq Ft
      • Built 1996
      13 Old Ridge Rd, Winhall, VT 05155

      Last Sold Summary

      • $367/SF
      • 29 Days On Market
      • Last Sold Price $855,000
      • May 01, 2023

      Last Listing Agent Carrie Mathews Winhall Real Estate

Showing Results 41 - 80, Page 2 of 18

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