2,703

Woodstock, VT Homes

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  • /48

    $502,000

    $25K PRICE DROP Under Contract
    • 4 Beds
    • 2.5 Baths
    • 1,824 Sq Ft

    88 Happy Valley Rd, Woodstock, VT 05091

    Step into a rare offering where timeless New England charm meets contemporary comfort. Originally built in 1846 and thoughtfully reimagined, this exceptional Taftsville, Vermont residence is set along Happy Valley Brook, creating a private sanctuary defined by peace, beauty, and understated elegance. Historic character is beautifully complemented by carefully curated upgrades, including

    Julie Davis KW Vermont Woodstock

    88 Happy Valley Rd, Woodstock, VT 05091
  • /11

    $190,000

    Sold May 29, 2026

    99 Safford Commons Way, Woodstock, VT 05091

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Built 2025

    Last Sold Summary

    • $158/SF
    • 115 Days On Market

    Last Listing Agent Jane Darrach Martha E. Diebold/Hanover

    99 Safford Commons Way, Woodstock, VT 05091
    • /36

      Est $600,065

      Not Listed For Sale

      24 High St, Woodstock, VT 05091

      • 5 Beds
      • 2 Baths
      • 2,996 Sq Ft
      • Built 1840
      24 High St, Woodstock, VT 05091

      Last Sold Summary

      • 325 Days On Market

      Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

  • /51

    $6,673,000

    Pending
    • 5 Beds
    • 3.5 Baths
    • 4,165 Sq Ft

    2358 Long Hill Rd, Woodstock, VT 05091

    Framed by groves of mature birch trees, a winding drive descends into a private valley surrounded by pastures, apple orchards, a spring-fed pond, and sweeping mountain views, arriving at Birch Tree Farm. Spanning more than 465 acres, this extraordinary Vermont retreat offers an immersive four-season lifestyle -- from pressing fresh cider from the orchard and tapping maple trees for syrup to

    Story Jenks LandVest, Inc/Woodstock

    2358 Long Hill Rd, Woodstock, VT 05091
  • /48

    $705,000

    Sold Nov 26, 2025

    25 Linden Hill St, Woodstock, VT 05091

    • 3 Beds
    • 2 Baths
    • 1,694 Sq Ft
    • Built 1910

    Last Sold Summary

    • 11% Below List Price
    • $416/SF
    • 217 Days On Market

    Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

    25 Linden Hill St, Woodstock, VT 05091
    • /39

      Est $769,958

      Not Listed For Sale

      6 Highland Ave, Woodstock, VT 05091

      • 1 Bed
      • 1 Bath
      • 1,052 Sq Ft
      • Built 1930
      6 Highland Ave, Woodstock, VT 05091

      Last Sold Summary

      • 97 Days On Market

      Last Listing Agent John Wetmore Wetmore Real Estate

  • /11

    $779,000

    $200K PRICE INCREASE Pending
    • Land
    • 6.46 Acres
    • $120,588 per Acre

    0 Barnard Rd Unit 20.002, Woodstock, VT 05091

    A truly unique 6 acre parcel of land conveniently located in the heart of Woodstock! Tremendous development potential! Zoning allows both COMMERCIAL and RESIDENTIAL use! The 6 acres visually divide into 2 components with 2 diverse personalities. The 1st component is an extraordinary private building lot in the heart of Woodstock! Access to this 4 acre component initially leads through a pleasant

    John Wetmore Wetmore Real Estate

    0 Barnard Rd Unit 20.002, Woodstock, VT 05091
  • /30

    $405,000

    Sold Feb 17, 2026

    37 Atwood Ave, Woodstock, VT 05091

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1960

    Last Sold Summary

    • 16% Below List Price
    • $527/SF
    • 152 Days On Market

    Current Estimated Value $416,935

    Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

    37 Atwood Ave, Woodstock, VT 05091
    • /37

      Est $903,725

      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

      • 14 Days On Market

      Last Listing Agent Marni Rieger KW Vermont-Killington

  • /40

    $2,500,000

    $1M PRICE DROP Under Contract
    • 6 Beds
    • 6 Baths
    • 5,433 Sq Ft

    61 Academy Cir, Woodstock, VT 05071

    Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The

    Carol Wood Williamson Group Sothebys Intl. Realty

    61 Academy Cir, Woodstock, VT 05071
  • /11

    $190,000

    Sold May 15, 2026

    111 Safford Commons Way, Woodstock, VT 05091

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Built 2025

    Last Sold Summary

    • $158/SF
    • 101 Days On Market

    Last Listing Agent Jane Darrach Martha E. Diebold/Hanover

    111 Safford Commons Way, Woodstock, VT 05091
    • /38

      Est $602,962

      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

      • 83 Days On Market

      Last Listing Agent Holly Hall Hall Collins Real Estate Group

  • /14

    $238,000

    $2K PRICE INCREASE
    • 1 Bed
    • 1 Bath
    • 856 Sq Ft

    42 Heritage Condo Way Unit 24, Woodstock, VT 05091

    Amazing opportunity to own a property that is perfect as a full time home or a vacation get away, in the highly desired Heritage Condo community. Quiet setting in a low density area. This end unit condo has had many updates and is ready for new owners to add their personal touch. A private deck looking out to woodlands and lawn. The bright kitchen is a pleasure to work in . Upstairs the den with

    Ara Cardew BHG Masiello Keene

    42 Heritage Condo Way Unit 24, Woodstock, VT 05091
  • /60

    $1,080,000

    Sold Jul 24, 2026

    2 High St, Woodstock, VT 05091

    • 3 Beds
    • 3 Baths
    • 1,950 Sq Ft
    • Built 1890

    Last Sold Summary

    • 10% Below List Price
    • $554/SF
    • 12 Days On Market

    Current Estimated Value $803,566

    Last Listing Agent John Bassette Bassette Real Estate Group

    2 High St, Woodstock, VT 05091
    • /30

      Est $853,336

      Not Listed For Sale

      1 Border Ln, Woodstock, VT 05091

      • 3 Beds
      • 1.5 Baths
      • 1,368 Sq Ft
      • Built 1966
      1 Border Ln, Woodstock, VT 05091

      Last Sold Summary

      • 185 Days On Market

      Last Listing Agent Dan Noble Snyder Donegan Real Estate Group

  • /46

    $718,500

    $31K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,660 Sq Ft

    37 South St, Woodstock, VT 05091

    Great new price! Nestled in the vibrant heart of Woodstock Village, this beautifully renovated residence offers the ultimate "walk to all" lifestyle.Stepping inside, newly installed pine flooring guides you through an inviting main level designed for both daily living and effortless entertaining. The cozy living room anchors the home with its warm gas fireplace, while the spacious dining area

    Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

    37 South St, 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 $1,577,296

    Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

    20 The Green, Woodstock, VT 05091
    • /39

      Est $3,534,364

      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

      • 345 Days On Market

      Last Listing Agent Story Jenks LandVest, Inc/Woodstock

  • /30

    $799,000

    • 3 Beds
    • 3 Baths
    • 2,004 Sq Ft

    1326 Curtis Hollow Rd, Woodstock, VT 05091

    If you've been dreaming of the quintessential Vermont lifestyle, this exceptional property delivers the perfect blend of privacy, charm, and convenience. Nestled on over 30 acres in Woodstock, this classic farmhouse is surrounded by beautiful open fields, mature trees, and peaceful natural beauty. Inside, you'll find a spacious eat-in kitchen that's perfect for gathering with family and friends,

    Mandolyn McIntyre Crow Real Broker LLC

    1326 Curtis Hollow Rd, Woodstock, VT 05091
  • /43

    $515,000

    Sold May 29, 2026

    1514 South Rd, Woodstock, VT 05091

    • 3 Beds
    • 2 Baths
    • 1,920 Sq Ft
    • Built 1965

    Last Sold Summary

    • 26% Below List Price
    • $268/SF
    • 226 Days On Market

    Current Estimated Value $544,303

    Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

    1514 South Rd, Woodstock, VT 05091
    • /40

      Est $1,577,430

      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

      • 102 Days On Market

      Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

  • /22

    $799,999

    $5K PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    3036 W Woodstock Rd, Woodstock, VT 05091

    On a small hill, amongst trees and beautiful gardens, sits this beautifully maintained log cabin with sweeping views of the surrounding mountains and river valley. Just a short drive outside of Woodstock Village, this cabin offers the perfect blend of privacy and convenience. Built in 1996, this thoughtfully crafted home features approximately 2,600 square feet of living space on 2.9 acres. The

    Jennifer Kirkman KW Vermont Woodstock

    3036 W Woodstock Rd, Woodstock, VT 05091
  • /26

    $456,250

    Sold May 15, 2026

    57 Townhouse Way Unit 9, Woodstock, VT 05091

    • 3 Beds
    • 2.5 Baths
    • 1,728 Sq Ft
    • Built 1978

    Last Sold Summary

    • 2% Below List Price
    • $264/SF
    • 11 Days On Market

    Current Estimated Value $454,687

    Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

    57 Townhouse Way Unit 9, Woodstock, VT 05091
    • /29

      Est $823,652

      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

      • 84 Days On Market

      Last Listing Agent Herb Hart Quechee Lakes Real Estate Center

  • /33

    $695,000

    $55K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,285 Sq Ft

    47 Pleasant St, Woodstock, VT 05091

    Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space downstairs (which previously has been living space), combined with a separate two-bedroom apartment (with its own access) upstairs. The 1,335 sf lower level (Unit C) is currently a chiropractor's office space and was previously used

    John Snyder Snyder Donegan Real Estate Group

    47 Pleasant St, Woodstock, VT 05091
  • /24

    $629,500

    Sold Sep 12, 2025

    40 Pomfret Rd, Woodstock, VT 05091

    • 3 Beds
    • 1.5 Baths
    • 1,650 Sq Ft
    • Built 1885

    Last Sold Summary

    • $382/SF
    • 17 Days On Market

    Current Estimated Value $644,109

    Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

    40 Pomfret Rd, Woodstock, VT 05091
    • /42

      Est $1,628,033

      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

      • 79 Days On Market

      Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  • /39

    $595,000

    $100K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,288 Sq Ft

    11 Maple St, Woodstock, VT 05091

    A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is conveniently nearby! For children in Maple Street's Neighborhood, Woodstock Elementary School is just a short walk away. Currently the residence is configured as home to 2 generations of occupants. A ground floor apartment conveniently

    John Wetmore Wetmore Real Estate

    11 Maple St, Woodstock, VT 05091
  • /38

    $400,000

    Sold Jan 09, 2026

    144 Butternut Ln, Woodstock, VT 05091

    • 4 Beds
    • 3 Baths
    • 2,557 Sq Ft
    • Built 1846

    Last Sold Summary

    • 47% Below List Price
    • $156/SF
    • 190 Days On Market

    Current Estimated Value $440,874

    Last Listing Agent Scott Monahan Williamson Group Sothebys Intl. Realty

    144 Butternut Ln, Woodstock, VT 05091
    • /40

      Est $862,527

      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

      • 15 Days On Market

      Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  • /31

    $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. About 20 minutes to Ascutney

    Matthew Spittle Vermont Horse Country Real Estate

    0 South Rd, Woodstock, VT 05071
  • /27

    $630,000

    Sold May 11, 2026

    19 Davry Way, Woodstock, VT 05091

    • 3 Beds
    • 2 Baths
    • 2,183 Sq Ft
    • Built 1999

    Last Sold Summary

    • 1% Below List Price
    • $289/SF
    • 2 Days On Market

    Current Estimated Value $634,413

    Last Listing Agent Julie Davis KW Vermont Woodstock

    19 Davry Way, Woodstock, VT 05091
    • /40

      Est $1,004,608

      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

      • 4 Days On Market

      Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  • /41

    $659,000

    $30K PRICE DROP Under Contract
    • 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
  • /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
    • /37

      Est $968,260

      Not Listed For Sale

      4 River St, Woodstock, VT 05091

      • 2 Beds
      • 2.5 Baths
      • 2,176 Sq Ft
      • Built 1847
      4 River St, Woodstock, VT 05091

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

  • /60

    $2,225,000

    • 4 Beds
    • 3 Baths
    • 3,867 Sq Ft

    473 Kendall Rd, Woodstock, VT 05091

    Nestled in amongst flowering lilacs, ancient apple trees, and terraced English perennial gardens, this lovingly restored classic antique stone cape has all the conveniences of modern living, while honoring and preserving the charming period detail. Built in 1860, the home is an impressive example of snecked ashlar stone construction, which was introduced to this region by Scottish immigrants in

    Danny Kogut Williamson Group Sothebys Intl. Realty

    473 Kendall Rd, Woodstock, VT 05091
  • /45

    $712,000

    Sold Apr 30, 2026

    137 Laughlin Rd, Woodstock, VT 05091

    • 5 Beds
    • 3 Baths
    • 3,028 Sq Ft
    • Built 1972

    Last Sold Summary

    • 2% Below List Price
    • $235/SF
    • 20 Days On Market

    Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

    137 Laughlin Rd, Woodstock, VT 05091
    • /39

      Est $1,045,808

      Not Listed For Sale

      13 River St, Woodstock, VT 05091

      • 3 Beds
      • 3.5 Baths
      • 2,894 Sq Ft
      • Built 2021
      13 River St, Woodstock, VT 05091

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent John Snyder Snyder Donegan Real Estate Group

  • /57

    $839,500

    Under Contract
    • 3 Beds
    • 3 Baths
    • 2,667 Sq Ft

    217 S Perry Rd, Woodstock, VT 05091

    This spacious, well-maintained Gambrel-style home is designed for gracious country living, with a post-and-beam frame that creates large gathering spaces accented by two fireplaces, thoughtful features, and abundant natural light. The private parcel, landscaped with perennials and flowering shrubs, is positioned on a rise overlooking the Barnard Valley towards Woodstock, a few miles south. The

    Laird Bradley Williamson Group Sothebys Intl. Realty

    217 S Perry Rd, Woodstock, VT 05091

Showing Results 41 - 80, Page 2 of 18

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