1,910

Woodstock Town, VT Homes

Section Image
    • /40

      Not Listed For Sale

      327 Fletcher Schoolhouse Rd, Woodstock, VT 05071

      • 4 Beds
      • 3.5 Baths
      • 4,638 Sq Ft
      • Built 1797
      327 Fletcher Schoolhouse Rd, Woodstock, VT 05071

      Last Sold Summary

      • 121 Days On Market

      Last Listing Agent Story Jenks LandVest, Inc/Woodstock

  • /58

    $2,300,000

    • 5 Beds
    • 6 Baths
    • 3,489 Sq Ft

    915 Peterkin Hill Rd, South Woodstock, VT 05071

    Exceptional Views to Killington! Perched high on a private knoll and surrounded by open lush meadows and surrounded by antique stonewalls. This 5 bedroom, 4 bathroom extended cape styled home was renovated approx 15 years ago with handsome hardwood floors throughout. Large kitchen with Calcutta Marble, Electrolux stainless appliances and ample storage that opens into the dining room- The formal

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    915 Peterkin Hill Rd, South Woodstock, VT 05071
  • /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
    • /30

      Est $1,326,325

      Not Listed For Sale

      2409 South Rd, Woodstock, VT 05091

      • 4 Beds
      • 2.5 Baths
      • 2,758 Sq Ft
      • Built 1920
      2409 South Rd, Woodstock, VT 05091

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

  • /44

    $650,000

    • 2 Beds
    • 2 Baths
    • 1,044 Sq Ft

    35 White Loop Unit B101, Ludlow, VT 05149

    Winterplace on Okemo Mountain. This is a must see condominium at an unbeatable location on Okemo. Located at the top of the A & B quad which brings you directly to the Sunburst Six summit chairlift. Natural light fills the bright living space with an open floor plan for the living room, kitchen, and dining area. There is plenty of space for family and friends to gather. A few key features include

    Katherine Burns William Raveis Real Estate Vermont Properties

    35 White Loop Unit B101, Ludlow, VT 05149
  • /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 $1,339,753

      Not Listed For Sale

      282 Fletcher Hill Rd, Woodstock, VT 05091

      • 3 Beds
      • 3 Baths
      • 2,329 Sq Ft
      • Built 1986
      282 Fletcher Hill Rd, Woodstock, VT 05091

      Last Sold Summary

      • 92 Days On Market

      Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

  • /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
  • /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
    • /32

      Est $556,731

      Not Listed For Sale

      35 White Loop Unit B-102, Ludlow, VT 05149

      • 2 Beds
      • 2 Baths
      • 1,100 Sq Ft
      • Built 1988
      35 White Loop Unit B-102, Ludlow, VT 05149

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Katherine Burns William Raveis Real Estate Vermont Properties

  • /28

    $395,000

    • Land
    • 8 Acres
    • $49,375 per Acre

    0 Vermont 106, South Woodstock, VT 05071

    Rare opportunity to own 8 +/- acres of land in South Woodstock Village with easy access off of Rt. 106. This parcel is being divided off of a 10.87 acre lot. There is a wonderful , open site ideal for building your dream home offering privacy , trails and a short walk to the South Woodstock Country Store, Kedron Valley Inn , dining at the Ransom Tavern and a swim in the Kedron pond ! 5 miles into

    Carol Wood Williamson Group Sothebys Intl. Realty

    0 Vermont 106, South Woodstock, VT 05071
  • /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
    • /38

      Est $1,206,105

      Not Listed For Sale

      2876 Hartland Hill Rd, Woodstock, VT 05091

      • 4 Beds
      • 3.5 Baths
      • 3,350 Sq Ft
      • Built 1807
      2876 Hartland Hill Rd, Woodstock, VT 05091

      Last Sold Summary

      • 112 Days On Market

      Last Listing Agent Carol Wood 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
  • /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 $931,270

    Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

    348 Laughlin Rd, Woodstock, VT 05091
    • /40

      Est $432,907

      Not Listed For Sale

      1880 South Rd, Woodstock, VT 05091

      • 3 Beds
      • 2 Baths
      • 1,374 Sq Ft
      • Built 1900
      1880 South Rd, Woodstock, VT 05091

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Daniel Pol Killington Pico Realty

  • /47

    $795,000

    • 2 Beds
    • 3 Baths
    • 1,304 Sq Ft

    35 White Loop Unit B301, Ludlow, VT 05149

    Enjoy the best of the Okemo lifestyle at Winterplace B301, a tastefully updated slopeside condominium offering beautiful long-range mountain views and excellent rental potential. This inviting top-floor residence features two bedrooms plus a spacious loft, providing plenty of room for family and guests. The primary bedroom, second bedroom, and loft area each enjoy access to a private en-suite

    Sarah Sheehan William Raveis Real Estate Vermont Properties

    35 White Loop Unit B301, Ludlow, VT 05149
  • /41

    $780,000

    Sold Apr 10, 2026

    403 Horse Shoe Way, Woodstock, VT 05071

    • 2 Beds
    • 1.5 Baths
    • 1,714 Sq Ft
    • Built 1987

    Last Sold Summary

    • 8% Below List Price
    • $455/SF
    • 280 Days On Market

    Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

    403 Horse Shoe Way, Woodstock, VT 05071
    • /26

      Est $1,448,271

      Not Listed For Sale

      76 Grove Hill Rd, Woodstock, VT 05091

      • 3 Beds
      • 2.5 Baths
      • 2,443 Sq Ft
      • Built 1983
      76 Grove Hill Rd, Woodstock, VT 05091

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent John Snyder Snyder Donegan Real Estate Group

  • /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
  • /60

    $2,097,500

    Sold Mar 13, 2026

    1362 Barnard Rd, Woodstock, VT 05091

    • 6 Beds
    • 5 Baths
    • 3,645 Sq Ft
    • Built 1855

    Last Sold Summary

    • 19% Below List Price
    • $575/SF
    • 128 Days On Market

    Current Estimated Value $2,180,345

    Last Listing Agent Chris Lang

    1362 Barnard Rd, Woodstock, VT 05091
    • /40

      Not Listed For Sale

      418 Fletcher Hill Rd, South Woodstock, VT 05071

      • 3 Beds
      • 2.5 Baths
      • 2,434 Sq Ft
      • Built 2001
      418 Fletcher Hill Rd, South Woodstock, VT 05071

      Last Sold Summary

      • 43 Days On Market

      Last Listing Agent Terry Davis 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
  • /60

    $775,000

    Sold May 11, 2026

    3961 Hartland Hill Rd, Woodstock, VT 05091

    • 5 Beds
    • 5 Baths
    • 3,886 Sq Ft
    • Built 1964

    Last Sold Summary

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

    Current Estimated Value $830,055

    Last Listing Agent Tambrey Vutech KW Vermont Woodstock

    3961 Hartland Hill Rd, Woodstock, VT 05091
    • /40

      Not Listed For Sale

      486 Benedict Rd, South Woodstock, VT 05071

      • 6 Beds
      • 7 Baths
      • 6,040 Sq Ft
      • Built 1820
      486 Benedict Rd, South Woodstock, VT 05071

      Last Sold Summary

      • 210 Days On Market

      Last Listing Agent John Snyder 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
  • /40

    $740,000

    Sold Aug 18, 2025

    339 Gully Rd, Woodstock, VT 05091

    • 4 Beds
    • 2.5 Baths
    • 2,688 Sq Ft
    • Built 1975

    Last Sold Summary

    • 5% Below List Price
    • $275/SF
    • 67 Days On Market

    Current Estimated Value $855,349

    Last Listing Agent Derek Cosentino Four Seasons Sotheby's Int'l Realty

    339 Gully Rd, Woodstock, VT 05091
    • /20

      Est $2,411,790

      Not Listed For Sale

      3086 South Rd, Woodstock, VT 05091

      • 4 Beds
      • 4.5 Baths
      • 3,550 Sq Ft
      • Built 1986
      3086 South Rd, Woodstock, VT 05091

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent John Snyder Snyder Donegan Real Estate Group

  • /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
  • /35

    $462,000

    Sold May 28, 2026

    3364 W Woodstock Rd, Woodstock, VT 05091

    • 4 Beds
    • 3 Baths
    • 2,470 Sq Ft
    • Built 1840

    Last Sold Summary

    • 16% Below List Price
    • $187/SF
    • 241 Days On Market

    Current Estimated Value $494,817

    Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

    3364 W Woodstock Rd, Woodstock, VT 05091
    • /40

      Est $832,495

      Not Listed For Sale

      917 Carlton Hill Rd, Woodstock, VT 05091

      • 3 Beds
      • 2.5 Baths
      • 1,844 Sq Ft
      • Built 1975
      917 Carlton Hill Rd, Woodstock, VT 05091

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  • /19

    $529,000

    $50K PRICE DROP
    • Land
    • 60.57 Acres
    • $8,734 per Acre

    0 Noah Wood Rd, Woodstock, VT 05071

    Incredible location! 60+ acres situated on the corner of South Rd. (106) and Noah Wood Rd. in beautiful South Woodstock. The land rises from the roads to the crest of the hilltop with amazing view potential looking to the Northeast. Multiple building sites can be found throughout the property which offers great recreational opportunities including direct access to the VAST trail on the lower

    Dan Noble Snyder Donegan Real Estate Group

    0 Noah Wood Rd, Woodstock, VT 05071
  • /50

    $875,000

    Sold Feb 10, 2026

    100 Pomfret Rd, Woodstock, VT 05091

    • 4 Beds
    • 2.5 Baths
    • 2,044 Sq Ft
    • Built 1930

    Last Sold Summary

    • 7% Below List Price
    • $428/SF
    • 163 Days On Market

    Current Estimated Value $863,823

    Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

    100 Pomfret Rd, Woodstock, VT 05091
    • /40

      Not Listed For Sale

      587 Old River Rd, Woodstock, VT 05091

      • 5 Beds
      • 5.5 Baths
      • 6,799 Sq Ft
      • Built 1850
      587 Old River Rd, Woodstock, VT 05091

      Last Sold Summary

      • 473 Days On Market

      Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

  • /58

    $2,950,000

    • 8 Beds
    • 8 Baths
    • 6,200 Sq Ft

    5798 South Rd, Woodstock, VT 05071

    Kedron Valley Farm c1850: A classic beauty, perched on a knoll overlooking the idyllic hills and lush meadows of the valley with approx 32 acres. This stunning extended antique post and beam cape is complete with a large traditional 4 story barn with 6 horse stables and equipment sheds offers everything one could wish for in a country property. The grounds include gracious old maples, beautiful

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    5798 South Rd, Woodstock, VT 05071
  • /26

    $205,000

    Sold Nov 21, 2025

    33 Heritage Condos Way Unit 33D, Woodstock, VT 05091

    • 1 Bed
    • 1 Bath
    • 856 Sq Ft
    • Built 1984

    Last Sold Summary

    • 2% Below List Price
    • $239/SF
    • 10 Days On Market

    Last Listing Agent Jennifer Falvey KW Vermont Woodstock

    33 Heritage Condos Way Unit 33D, Woodstock, VT 05091
    • /38

      Est $833,519

      Not Listed For Sale

      506 Westerdale Rd, Woodstock, VT 05091

      • 3 Beds
      • 2 Baths
      • 1,492 Sq Ft
      • Built 1987
      506 Westerdale Rd, Woodstock, VT 05091

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  • /60

    $525,000

    $70K PRICE DROP
    • Land
    • 20.2 Acres
    • $25,990 per Acre

    00 Long Hill Rd, Woodstock, VT 05071

    Discover the perfect blend of privacy and convenience with this exceptional 20.2-acre parcel, combining two lots into one remarkable opportunity. Featuring a 50 foot right-of-way for access, this wooded retreat offers multiple prime building sites. With selective clearing, you can take in breathtaking views in your choice of direction; east, south, north, or west. Located just minutes from South

    Eric Johnston Four Seasons Sotheby's Int'l Realty

    00 Long Hill Rd, Woodstock, VT 05071
  • /40

    $660,000

    Sold Apr 30, 2026

    3914 South Rd, Woodstock, VT 05091

    • 4 Beds
    • 3 Baths
    • 3,584 Sq Ft
    • Built 1984

    Last Sold Summary

    • 9% Below List Price
    • $184/SF
    • 142 Days On Market

    Current Estimated Value $713,570

    Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

    3914 South Rd, Woodstock, VT 05091
    • /40

      Est $681,144

      Not Listed For Sale

      64 Fowler Rd Unit Q104, Ludlow, VT 05149

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1989
      64 Fowler Rd Unit Q104, Ludlow, VT 05149

      Last Sold Summary

      • 101 Days On Market

      Last Listing Agent Joseph Karl William Raveis Real Estate Vermont Properties

Showing Results 41 - 80, Page 2 of 18

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