2,958

South Woodstock, VT Homes

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  • /27

    $639,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 2,183 Sq Ft

    19 Davry Way, Woodstock, VT 05091

    You know that feeling when you walk through a door and you can already see future memories being made? That's what you feel as you turn every corner of this gem. This thoughtfully updated raised ranch blends comfort, style, and convenience seamlessly with plenty of natural light filling much of the home. Recent improvements include beautifully renovated bathrooms, gleaming hardwood floors, a new

    Julie Davis KW Vermont Woodstock

    19 Davry Way, Woodstock, VT 05091
  • /57

    $1,710,000 Sold Dec 05, 2025

    20 The Green, Woodstock, VT 05091

    • 3 Beds
    • 2.5 Baths
    • 2,688 Sq Ft
    • Built 1826

    Last Sold Summary

    • 14% Below List Price
    • $636/SF
    • 139 Days On Market

    Current Estimated Value $1,747,990

    Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

    20 The Green, Woodstock, VT 05091
    • /37

      Est $857,905 Not Listed For Sale

      13 High St, Woodstock, VT 05091

      • 3 Beds
      • 2 Baths
      • 1,800 Sq Ft
      • Built 1900
      13 High St, Woodstock, VT 05091

      Last Sold Summary

      • 8% Below List Price
      • $519/SF
      • 14 Days On Market

      Last Sold Price $935,000

      Last Listing Agent Marni Rieger KW Vermont-Killington

  • /39

    $749,000

    • 3 Beds
    • 4 Baths
    • 1,660 Sq Ft

    37 South St, Woodstock, VT 05091

    Welcome to this beautifully renovated residence in the vibrant heart of Woodstock Village. Enjoy unparalleled convenience with a short stroll to the Elementary School, Woodstock Inn, the picturesque Green, and an array of charming shops, restaurants, and bakeries that define village living. Nestled directly across from Vail Field, this home offers easy access to playgrounds, ball fields, and

    Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

    37 South St, Woodstock, VT 05091
  • /36

    $440,000 Sold Jul 15, 2025

    215 Densmore Hill Rd, Hartland, VT 05048

    • 2 Beds
    • 2 Baths
    • 1,032 Sq Ft
    • Built 1990

    Last Sold Summary

    • $426/SF
    • 116 Days On Market

    Current Estimated Value $445,123

    Last Listing Agent Sue Starr-Adams EXP Realty

    215 Densmore Hill Rd, Hartland, VT 05048
    • /38

      Est $586,393 Not Listed For Sale

      39 South St, Woodstock, VT 05091

      • 2 Beds
      • 1.5 Baths
      • 1,020 Sq Ft
      • Built 1869
      39 South St, Woodstock, VT 05091

      Last Sold Summary

      • 23% Above List Price
      • $466/SF
      • 83 Days On Market

      Last Sold Price $475,000

      Last Listing Agent Holly Hall Hall Collins Real Estate Group

  • /45

    $725,000 Under Contract

    • 5 Beds
    • 3 Baths
    • 3,028 Sq Ft

    137 Laughlin Rd, Woodstock, VT 05091

    Charming property located just minutes from historic Woodstock Green. The main house first floor features 3 bedrooms/ 1bath with formal dining room, living room and kitchen on first level anchored by an expansive deck for entertaining or enjoying the afternoon sun. Handsome hardwood floors throughout, stainless appliances in the kitchen accented with granite countertops. The lower level is walk

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    137 Laughlin Rd, Woodstock, VT 05091
  • /40

    $750,000 Sold May 01, 2025

    6963 South Rd, Woodstock, VT 05071

    • 2 Beds
    • 1.5 Baths
    • 1,840 Sq Ft
    • Built 1970

    Last Sold Summary

    • 6% Below List Price
    • $408/SF
    • 43 Days On Market

    Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

    6963 South Rd, Woodstock, VT 05071
    • /39

      Est $3,545,484 Not Listed For Sale

      3 Church St, Woodstock, VT 05091

      • 10 Beds
      • 15 Baths
      • 10,206 Sq Ft
      • Built 1831
      3 Church St, Woodstock, VT 05091

      Last Sold Summary

      • 9% Above List Price
      • $319/SF
      • 345 Days On Market

      Last Sold Price $3,255,000

      Last Listing Agent Story Jenks LandVest, Inc/Woodstock

  • /41

    $845,000 Pending

    • 2 Beds
    • 1.5 Baths
    • 1,714 Sq Ft

    403 Horse Shoe Way, Woodstock, VT 05071

    Totally secluded on a rolling hillside, just 10 minutes from the Woodstock Village Green, this storybook Post and Beam cottage awaits your vision. From the reclaimed centuries old barn frame to the massive fieldstone fireplace, every detail is well thought, and impeccably executed honoring the Vermont tradition of reclaiming and utilizing locally sourced materials.The home was carefully, and

    Danny Kogut Williamson Group Sothebys Intl. Realty

    403 Horse Shoe Way, Woodstock, VT 05071
  • /51

    $1,300,000 Sold Jul 02, 2025

    608 Fletcher Hill Rd, Woodstock, VT 05091

    • 4 Beds
    • 3.5 Baths
    • 4,228 Sq Ft
    • Built 1980

    Last Sold Summary

    • 13% Below List Price
    • $307/SF
    • 91 Days On Market

    Current Estimated Value $1,315,815

    Last Listing Agent Sandy Reavill

    608 Fletcher Hill Rd, Woodstock, VT 05091
    • /40

      Est $1,523,210 Not Listed For Sale

      26 River St, Woodstock, VT 05091

      • 6 Beds
      • 4 Baths
      • 3,719 Sq Ft
      • Built 1845
      26 River St, Woodstock, VT 05091

      Last Sold Summary

      • 38% Above List Price
      • $296/SF
      • 102 Days On Market

      Last Sold Price $1,100,000

      Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

  • /33

    $339,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    7 Best Rd, West Windsor, VT 05089

    Nestled on a picturesque 2.9 acres along Hartland-Brownsville Rd, this property offers the perfect blend of privacy and convenience offering sweeping views and mature trees. This unique property features a 1994 Skyline doublewide home with a newer attached 2 car garage. Step into the heart of the main home and be greeted by an abundance of natural light streaming through large windows that

    Seth Barbiero EXP Realty

    7 Best Rd, West Windsor, VT 05089
  • /24

    $230,000 Sold Jan 07, 2026

    42 Heritage Condo Way Unit 22, Woodstock, VT 05091

    • 1 Bed
    • 1 Bath
    • 816 Sq Ft
    • Built 1987

    Last Sold Summary

    • 6% Below List Price
    • $282/SF
    • 66 Days On Market

    Last Listing Agent Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

    42 Heritage Condo Way Unit 22, Woodstock, VT 05091
    • /29

      Est $773,942 Not Listed For Sale

      42 River St, Woodstock, VT 05091

      • 3 Beds
      • 2.5 Baths
      • 1,280 Sq Ft
      • Built 1890
      42 River St, Woodstock, VT 05091

      Last Sold Summary

      • 36% Above List Price
      • $445/SF
      • 84 Days On Market

      Last Sold Price $570,000

      Last Listing Agent Herb Hart Quechee Lakes Real Estate Center

  • /60

    $825,000 Under Contract

    • 5 Beds
    • 5 Baths
    • 3,886 Sq Ft

    3961 Hartland Hill Rd, Woodstock, VT 05091

    NEW PRICE! This lovely,expanded Cape sits just a half mile from Woodstock Village's East End.Surrounded by rolling green fields and wooded hillsides-this home offers a beautiful country setting less than a mile to village shopping, schools, dining and recreation. Updated with modern finishes to enhance accessibility and one level living-while maintaining the warm, country charm. First floor

    Tambrey Vutech KW Vermont Woodstock

    3961 Hartland Hill Rd, Woodstock, VT 05091
  • /18

    $287,500 Sold Jan 05, 2026

    17 High St Unit 2, Woodstock, VT 05091

    • 2 Beds
    • 1 Bath
    • 1,040 Sq Ft
    • Built 1980

    Last Sold Summary

    • 4% Below List Price
    • $276/SF
    • 10 Days On Market

    Current Estimated Value $296,085

    Last Listing Agent Terry Davis Williamson Group Sothebys Intl. Realty

    17 High St Unit 2, Woodstock, VT 05091
    • /42

      Est $1,559,905 Not Listed For Sale

      33 River St, Woodstock, VT 05091

      • 4 Beds
      • 4 Baths
      • 4,378 Sq Ft
      • Built 1886
      33 River St, Woodstock, VT 05091

      Last Sold Summary

      • 1% Below List Price
      • $361/SF
      • 79 Days On Market

      Last Sold Price $1,580,000

      Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  • /55

    $915,000 Under Contract

    • 3 Beds
    • 3 Baths
    • 2,150 Sq Ft

    509 Church Hill Rd, Wood Stock, VT 05091

    Enjoy in-town ease of living combined with Vermont country charm. This well maintained , efficient home provides first floor living with an additional lower floor ensuite bedroom /sitting area with direct access to lovely grounds and gardens.The light filled home is in excellent condition and is surrounded by fabulous perennial gardens, mature maple trees, raspberry and blueberry bushes ,

    Carol Wood Williamson Group Sothebys Intl. Realty

    509 Church Hill Rd, Wood Stock, VT 05091
  • /34

    $679,000 Sold Aug 04, 2025

    294 Barberry Hill Rd, Woodstock, VT 05091

    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft
    • Built 1968

    Last Sold Summary

    • $319/SF
    • 49 Days On Market

    Current Estimated Value $700,004

    Last Listing Agent Bonnie Bergeron Snyder Donegan Real Estate Group

    294 Barberry Hill Rd, Woodstock, VT 05091
    • /40

      Est $861,538 Not Listed For Sale

      25 Slayton Terrace, Woodstock, VT 05091

      • 3 Beds
      • 1.5 Baths
      • 1,632 Sq Ft
      • Built 1925
      25 Slayton Terrace, Woodstock, VT 05091

      Last Sold Summary

      • 9% Below List Price
      • $579/SF
      • 15 Days On Market

      Last Sold Price $945,000

      Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  • /24

    $646,500

    • Land
    • 37.85 Acres
    • $17,081 per Acre

    0 South Rd, Woodstock, VT 05071

    Country land at the south end of Woodstock reaching from RT 106 to the top of the ridge. Potential for views with clearing at several levels. Trails through the property with access to the GMHA network. Stonewalls and a stream.About two miles to GMHA and South Woodstock village, one mile to VAST trail.40 minutes to skiing at Killington, less to Okemos. Seven miles into Woodstock Village.

    Matthew Spittle Vermont Horse Country Real Estate

    0 South Rd, Woodstock, VT 05071
  • /36

    $1,800,000 Sold May 23, 2025

    484 Carlton Hill Rd, Woodstock, VT 05091

    • 4 Beds
    • 5 Baths
    • 4,100 Sq Ft
    • Built 2008

    Last Sold Summary

    • $439/SF
    • 61 Days On Market

    Current Estimated Value $1,849,526

    Last Listing Agent Jennifer Kirkman KW Vermont Woodstock

    484 Carlton Hill Rd, Woodstock, VT 05091
    • /40

      Est $948,400 Not Listed For Sale

      77 Central St, Woodstock, VT 05091

      • 4 Beds
      • 1.5 Baths
      • 2,136 Sq Ft
      • Built 1826
      77 Central St, Woodstock, VT 05091

      Last Sold Summary

      • 5% Below List Price
      • $468/SF
      • 4 Days On Market

      Last Sold Price $1,000,000

      Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  • /19

    $275,000

    • Land
    • 5 Acres
    • $55,000 per Acre

    95 Jenne Rd, Hartland, VT 05048

    5 acres of peacefully quiet land that are situated in an area well known to the equestrian community! Both the surrounding neighbors, on this seldom traveled country road, and numerous other properties in this broad community present as substantial privately sited homes. As you meander up Jenne Road to reach the parcel the classic large maple trees that typify the borders of pastoral Vermont

    John Wetmore Wetmore Real Estate

    95 Jenne Rd, Hartland, VT 05048
  • /20

    $2,900,000 Sold May 05, 2025

    3086 South Rd, Woodstock, VT 05091

    • 4 Beds
    • 4.5 Baths
    • 3,550 Sq Ft
    • Built 1986

    Last Sold Summary

    • 12% Above List Price
    • $817/SF
    • 0 Days On Market

    Current Estimated Value $2,968,328

    Last Listing Agent John Snyder Snyder Donegan Real Estate Group

    3086 South Rd, Woodstock, VT 05091
    • /47

      Est $872,395 Not Listed For Sale

      3894 Rush Meadow Rd, West Windsor, VT 05089

      • 4 Beds
      • 2 Baths
      • 2,000 Sq Ft
      • Built 1850
      3894 Rush Meadow Rd, West Windsor, VT 05089

      Last Sold Summary

      • 6% Below List Price
      • $462/SF
      • 42 Days On Market

      Last Sold Price $925,000

      Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

  • /45

    $675,000

    • 4 Beds
    • 3 Baths
    • 3,190 Sq Ft

    598 E Woodstock Rd, Woodstock, VT 05091

    Historic Woodstock, Vermont – Spacious Home on Nearly 3 Acres. Welcome to a rare opportunity in the heart of Woodstock, one of Vermont’s most picturesque and sought-after villages. This expansive home offers generous living space with many rooms, providing flexibility for a large household, home offices, guest quarters, or the potential to create multiple apartments (buyer to verify local

    Erika Smith Coldwell Banker LIFESTYLES - Hanover

    598 E Woodstock Rd, Woodstock, VT 05091
  • /31

    $920,000 Sold Nov 17, 2025

    348 Laughlin Rd, Woodstock, VT 05091

    • 4 Beds
    • 3 Baths
    • 2,882 Sq Ft
    • Built 1972

    Last Sold Summary

    • 1% Below List Price
    • $319/SF
    • 7 Days On Market

    Current Estimated Value $877,298

    Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

    348 Laughlin Rd, Woodstock, VT 05091
    • /33

      Est $911,867 Not Listed For Sale

      5434 Rush Meadow Rd, West Windsor, VT 05089

      • 3 Beds
      • 2.5 Baths
      • 2,988 Sq Ft
      • Built 2003
      5434 Rush Meadow Rd, West Windsor, VT 05089

      Last Sold Summary

      • 6% Below List Price
      • $326/SF
      • 6 Days On Market

      Last Sold Price $975,000

      Last Listing Agent David Donegan Snyder Donegan Real Estate Group

  • /6

    $560,000

    • Land
    • 50 Acres
    • $11,200 per Acre

    90 Reading Farms Rd, Reading, VT 05062

    Exceptional Private Land Offering with Southern Views. A rare opportunity to acquire a private parcel of land located directly off a paved, State maintained road. The property features beautiful southern exposure with multiple potential pond sites and a gently varied landscape ideal for estate development. Surrounded by large, protected, multi-million-dollar estates, the setting offers

    Derek Eisenberg Continental Real Estate Group, Inc.

    90 Reading Farms Rd, Reading, VT 05062
  • /17

    $86,500 Sold May 16, 2025

    132 Riverbend Way, Woodstock, VT 05091

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 2011

    Last Sold Summary

    • 13% Below List Price
    • $77/SF
    • 86 Days On Market

    Last Listing Agent Jenna Luce RE/MAX Upper Valley

    132 Riverbend Way, Woodstock, VT 05091
    • /40

      Est $549,106 Not Listed For Sale

      3052 Brownsville Hartland Rd, West Windsor, VT 05089

      • 2 Beds
      • 2 Baths
      • 2,012 Sq Ft
      • Built 1965
      3052 Brownsville Hartland Rd, West Windsor, VT 05089

      Last Sold Summary

      • 13% Above List Price
      • $241/SF
      • 64 Days On Market

      Last Sold Price $485,000

      Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

  • /24

    $452,600

    • 2,915 Sq Ft

    282 Skunk Hollow Rd, Hartland, VT 05048

    Two buildings on one parcel in desirable Hartland, Vermont! This flexible and well-maintained property includes a single-family home and a duplex, offering outstanding potential for owner occupancy, multi-generational living, or investment income. Ideally situated just 25 minutes from Hanover, NH, and 10 minutes from Woodstock, VT, this location provides the perfect balance of convenience and

    Loren Wehmeyer Tesla Realty Group, LLC

    282 Skunk Hollow Rd, Hartland, VT 05048
  • /25

    $525,000 Sold Oct 16, 2025

    19 Prospect St, Wood Stock, VT 05091

    • 2 Beds
    • 2 Baths
    • 1,482 Sq Ft
    • Built 1970

    Last Sold Summary

    • $354/SF
    • 2 Days On Market

    Current Estimated Value $517,425

    Last Listing Agent Katie McFadden RE/MAX North Professionals

    19 Prospect St, Wood Stock, VT 05091
    • /30

      Est $444,850 Not Listed For Sale

      6293 Route 106, Reading, VT 05062

      • 2 Beds
      • 2 Baths
      • 1,248 Sq Ft
      • Built 1989
      6293 Route 106, Reading, VT 05062

      Last Sold Summary

      • 10% Above List Price
      • $325/SF
      • 5 Days On Market

      Last Sold Price $405,000

      Last Listing Agent Kevin Barnes William Raveis Real Estate Vermont Properties

  • /40

    $695,000 Under Contract

    • 4 Beds
    • 3 Baths
    • 3,584 Sq Ft

    3914 South Rd, Woodstock, VT 05091

    This South Woodstock contemporary residence was designed by the original architect-owner to showcase Vermont’s changing seasons and capture views of the Kedron Brook as it wanders through the property past small meadows tucked in along the banks. The home can be accessed privately at grade level through the heated garage and mudroom, while guests enter via a covered entry to the upper level. The

    Laird Bradley Williamson Group Sothebys Intl. Realty

    3914 South Rd, Woodstock, VT 05091
  • /43

    $480,000 Sold Sep 26, 2025

    371 Vermont 12, Hartland, VT 05048

    • 3 Beds
    • 2 Baths
    • 2,616 Sq Ft
    • Built 1947

    Last Sold Summary

    • 12% Below List Price
    • $183/SF
    • 39 Days On Market

    Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

    371 Vermont 12, Hartland, VT 05048
    • /40

      Est $336,698 Not Listed For Sale

      4157 Route 106, Reading, VT 05062

      • 3 Beds
      • 1 Bath
      • 835 Sq Ft
      • Built 1961
      4157 Route 106, Reading, VT 05062

      Last Sold Summary

      • 22% Above List Price
      • $329/SF
      • 19 Days On Market

      Last Sold Price $275,000

      Last Listing Agent Frank Provance Diamond Realty

  • /44

    $730,000

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    46 Fowler Rd Unit O-205, Ludlow, VT 05149

    Winterplace at Okemo Mountain - Experience the ultimate in slopeside convenience, widely regarded as one of the most accessible locations on the mountain, with rare access to five chairlifts and nearby trail connections that bring you directly onto the slopes. This inviting three-bedroom, two-bathroom condo features an open-concept living area highlighted by a wood-burning fireplace—perfect for

    Katherine Burns William Raveis Real Estate Vermont Properties

    46 Fowler Rd Unit O-205, Ludlow, VT 05149

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