2,774

Woodstock, VT Homes

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  • /48

    $6,750,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 5,087 Sq Ft

    412 Skyland Ln, Woodstock, VT 05091

    Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 65 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains and

    Story Jenks LandVest, Inc/Woodstock

    412 Skyland Ln, Woodstock, VT 05091
  • /36

    $460,000 Sold Apr 18, 2025

    24 High St, Woodstock, VT 05091

    • 5 Beds
    • 2 Baths
    • 2,996 Sq Ft
    • Built 1840

    Last Sold Summary

    • 29% Below List Price
    • $154/SF
    • 325 Days On Market

    Current Estimated Value $472,307

    Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

    24 High St, Woodstock, VT 05091
    • /32

      Est $686,950 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,527 Sq Ft

      1207 Church Hill Rd, Woodstock, VT 05091

      1207 Church Hill Rd, Woodstock, VT 05091
  • /37

    $985,000

    • 4 Beds
    • 3 Baths
    • 2,785 Sq Ft

    1782 Randall Rd, Woodstock, VT 05091

    This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide

    Wade Treadway Wade I Treadway Real Estate

    1782 Randall Rd, Woodstock, VT 05091
  • /49

    $400,000 Sold Sep 30, 2025

    2 High St, Woodstock, VT 05091

    • 3 Beds
    • 3 Baths
    • 1,600 Sq Ft
    • Built 1890

    Last Sold Summary

    • 14% Below List Price
    • $250/SF
    • 89 Days On Market

    Last Listing Agent John Bassette Bassette Real Estate Group

    2 High St, Woodstock, VT 05091
    • /18

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,124 Sq Ft

      257 Riverbend Way, Woodstock, VT 05091

      257 Riverbend Way, Woodstock, VT 05091
  • /45

    $439,000

    • 4 Beds
    • 2 Baths
    • 1,617 Sq Ft

    5798 W Woodstock Rd, Woodstock, VT 05091

    Charming 4 bedroom farmhouse with attached barn/garage with lots of overhead storage is located across the road from the scenic Ottauquechee River. Minutes from Woodstock Village Green with all of its amenities and a short distance from Killington with its world renown Ski Resort. Year round activities abound ! The house has a sunny eat in kitchen, spacious dining room and a living room

    Carol Wood Williamson Group Sothebys Intl. Realty

    5798 W Woodstock Rd, Woodstock, VT 05091
  • /39

    $647,000 Sold Oct 06, 2025

    4165 Hartland Hill Rd, Woodstock, VT 05091

    • 4 Beds
    • 2 Baths
    • 1,654 Sq Ft
    • Built 1946

    Last Sold Summary

    • 5% Above List Price
    • $391/SF
    • 10 Days On Market

    Last Listing Agent John Wetmore Wetmore Real Estate

    4165 Hartland Hill Rd, Woodstock, VT 05091
    • /25

      Not Listed For Sale

      • 8 Beds
      • 5 Baths
      • 2,908 Sq Ft

      144 Town Farm Rd, Woodstock, VT 05071

      144 Town Farm Rd, Woodstock, VT 05071
  • /45

    $985,000

    • 3 Beds
    • 3 Baths
    • 1,920 Sq Ft

    72 Oakridge Way, Woodstock, VT 05091

    PRIME LOCATION! Tucked away at the end of a peaceful dead-end road in the Westerdale neighborhood is this Vermont Cape Cod home offers the perfect blend of privacy and convenience on just over 6 acres. Surrounded by mature trees and set on a wooded lot overlooking a tranquil pond, you’ll enjoy the calm of nature right outside your doorstep. The freshly installed deck provides a serene spot.

    Nancy Greenwood Watson Realty & Associates

    72 Oakridge Way, Woodstock, VT 05091
  • /27

    $900,000 Sold Oct 17, 2025

    19 Church St Unit EX, Woodstock, VT 05091

    • 5 Beds
    • 4.5 Baths
    • 3,486 Sq Ft
    • Built 1940

    Last Sold Summary

    • 25% Below List Price
    • $258/SF
    • 99 Days On Market

    Last Listing Agent John Snyder Snyder Donegan Real Estate Group

    19 Church St Unit EX, Woodstock, VT 05091
    • /11

      Not Listed For Sale

      • 11 Beds
      • 5 Baths
      • 6,095 Sq Ft

      7465 U S 4, Woodstock, VT 05091

      7465 U S 4, Woodstock, VT 05091
  • /60

    $1,995,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 5,573 Sq Ft

    851 Riverside Park Rd, Woodstock, VT 05091

    "All Seasons" is the ultimate Vermont retreat, designed for gatherings and getaways while seamlessly blending rustic charm with modern luxury. This 5,900-sq-ft barn-style home, just over five minutes from Woodstock Village via Route 4 and the Lincoln Covered Bridge, sits high on a knoll above the Ottauquechee River with views to Killington. A veritable mini-resort, the property offers

    Richard Higgerson Higgerson & Company

    851 Riverside Park Rd, Woodstock, VT 05091
  • /43

    $1,850,000 Sold Oct 24, 2025

    4945 South Rd, Woodstock, VT 05071

    • 5 Beds
    • 3.5 Baths
    • 3,502 Sq Ft
    • Built 1811

    Last Sold Summary

    • 26% Below List Price
    • $528/SF
    • 228 Days On Market

    Last Listing Agent Story Jenks LandVest, Inc/Woodstock

    4945 South Rd, Woodstock, VT 05071
    • /10

      Est $283,703 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 1,024 Sq Ft

      139 Doe Hill Way, Woodstock, VT 05091

      139 Doe Hill Way, Woodstock, VT 05091
  • /33

    $525,000 Sold Dec 22, 2025

    75 Pleasant St, Woodstock, VT 05091

    • 3 Beds
    • 1 Bath
    • 1,064 Sq Ft
    • Built 2020

    Last Sold Summary

    • $493/SF
    • 3 Days On Market

    Last Listing Agent Zoe Hathorn Washburn Snyder Donegan Real Estate Group

    75 Pleasant St, Woodstock, VT 05091
    • /40

      Est $567,066 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 1,296 Sq Ft

      4662 W Woodstock Rd, Woodstock, VT 05091

      4662 W Woodstock Rd, Woodstock, VT 05091
  • /35

    $499,000 Sold Dec 01, 2025

    85 Townhouse Way Unit 13, Woodstock, VT 05091

    • 2 Beds
    • 3 Baths
    • 2,209 Sq Ft
    • Built 1978

    Last Sold Summary

    • $226/SF
    • 6 Days On Market

    Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

    85 Townhouse Way Unit 13, Woodstock, VT 05091
    • /26

      Est $633,531 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 2,032 Sq Ft

      2456 Cox District Rd Unit 250.32.02.01, Woodstock, VT 05091

      2456 Cox District Rd Unit 250.32.02.01, Woodstock, VT 05091
  • /52

    $545,000 Sold Aug 06, 2025

    1613 W Woodstock Rd, Woodstock, VT 05091

    • 3 Beds
    • 1.5 Baths
    • 2,240 Sq Ft
    • Built 1944

    Last Sold Summary

    • 1% Below List Price
    • $243/SF
    • 53 Days On Market

    Current Estimated Value $523,638

    Last Listing Agent Holly Hall Hall Collins Real Estate Group

    1613 W Woodstock Rd, Woodstock, VT 05091
    • /40

      Est $333,622 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 868 Sq Ft

      1747 Long Hill Rd, Woodstock, VT 05091

      1747 Long Hill Rd, Woodstock, VT 05091
  • /42

    $587,715 Sold Dec 19, 2025

    93 Blake Hill Rd Unit B, Woodstock, VT 05091

    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft
    • Built 1981

    Last Sold Summary

    • 2% Below List Price
    • $280/SF
    • 18 Days On Market

    Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

    93 Blake Hill Rd Unit B, Woodstock, VT 05091
    • /39

      Est $873,953 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,894 Sq Ft

      13 River St, Woodstock, VT 05091

      13 River St, Woodstock, VT 05091
  • /43

    $700,000 Sold Feb 14, 2025

    944 College Hill Rd, Woodstock, VT 05091

    • 4 Beds
    • 2.5 Baths
    • 2,616 Sq Ft
    • Built 1988

    Last Sold Summary

    • 4% Below List Price
    • $268/SF
    • 15 Days On Market

    Current Estimated Value $740,836

    Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

    944 College Hill Rd, Woodstock, VT 05091
    • /30

      Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,152 Sq Ft

      5770 Stage Rd, Woodstock, VT 05091

      5770 Stage Rd, Woodstock, VT 05091
  • /50

    $2,220,000 Sold Nov 24, 2025

    1059 Carlton Hill Rd, Woodstock, VT 05091

    • 5 Beds
    • 4.5 Baths
    • 4,832 Sq Ft
    • Built 2005

    Last Sold Summary

    • 8% Below List Price
    • $459/SF
    • 37 Days On Market

    Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

    1059 Carlton Hill Rd, Woodstock, VT 05091
    • /37

      Est $937,976 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,344 Sq Ft

      1075 Barber Hill Rd, Woodstock, VT 05091

      1075 Barber Hill Rd, Woodstock, VT 05091
  • /49

    $875,000 Sold May 16, 2025

    19 Linden Hill St, Woodstock, VT 05091

    • 3 Beds
    • 3.5 Baths
    • 2,034 Sq Ft
    • Built 1992

    Last Sold Summary

    • $430/SF
    • 19 Days On Market

    Last Listing Agent Holly Hall Hall Collins Real Estate Group

    19 Linden Hill St, Woodstock, VT 05091
    • /40

      Est $430,240 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,457 Sq Ft

      1176 W Woodstock Rd, Woodstock, VT 05091

      1176 W Woodstock Rd, Woodstock, VT 05091
  • /42

    $627,500 Sold Oct 28, 2025

    11 1/2 Church St Unit 4, Woodstock, VT 05091

    • 2 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • Built 1900

    Last Sold Summary

    • 3% Below List Price
    • $404/SF
    • 3 Days On Market

    Last Listing Agent Susan Hickey Snyder Donegan Real Estate Group

    11 1/2 Church St Unit 4, Woodstock, VT 05091
    • /40

      Est $1,982,914 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,502 Sq Ft

      2018 Church Hill Rd, Woodstock, VT 05091

      2018 Church Hill Rd, Woodstock, VT 05091
  • /26

    $480,000 Sold Aug 15, 2025

    11A Prospect St, Woodstock, VT 05091

    • 2 Beds
    • 1.5 Baths
    • 930 Sq Ft
    • Built 1860

    Last Sold Summary

    • 2% Below List Price
    • $516/SF
    • 98 Days On Market

    Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

    11A Prospect St, Woodstock, VT 05091
    • /39

      Est $1,536,253 Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 3,962 Sq Ft

      268 Willow Brook Rd, Woodstock, VT 05091

      268 Willow Brook Rd, Woodstock, VT 05091
  • /8

    $110,000 Sold Mar 21, 2025

    1028 Fairbanks Turn, Woodstock, VT 05091

    • Land
    • 0.97 Acre
    • $113,402 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 162 Days On Market

    Last Listing Agent Heather Ashline BHHS Verani Upper Valley

    1028 Fairbanks Turn, Woodstock, VT 05091
    • /36

      Est $2,268,271 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,163 Sq Ft

      587 College Hill Rd, Woodstock, VT 05091

      587 College Hill Rd, Woodstock, VT 05091
  • /2

    $1,175,000 Sold Jan 29, 2025

    6453 South Rd, Woodstock, VT 05071

    • 3 Beds
    • 3 Baths
    • 2,660 Sq Ft
    • Built 2014

    Last Sold Summary

    • 30% Below List Price
    • $442/SF
    • 186 Days On Market

    Current Estimated Value $1,137,492

    Last Listing Agent Story Jenks LandVest, Inc/Woodstock

    6453 South Rd, Woodstock, VT 05071
    • /39

      Est $1,414,188 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 3,380 Sq Ft

      113 Prosper Rd, Woodstock, VT 05091

      113 Prosper Rd, Woodstock, VT 05091
    • /35

      Est $781,845 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,200 Sq Ft

      295 Mecawee Rd, Woodstock, VT 05091

      295 Mecawee Rd, Woodstock, VT 05091
    • /40

      Est $1,105,057 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,331 Sq Ft

      11 College Hill Rd, Woodstock, VT 05091

      11 College Hill Rd, Woodstock, VT 05091
    • /40

      Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 5,632 Sq Ft

      1862 Long Hill Rd, Woodstock, VT 05071

      1862 Long Hill Rd, Woodstock, VT 05071

Showing Results 161 - 200, Page 5 of 18

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