Woodstock, VT Homes

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  $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
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  /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
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  /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
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  $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
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  $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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  $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
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  /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
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  /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
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  $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
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  /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
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  /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
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  /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
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  $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
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  /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
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  $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
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  /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
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  $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
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  Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  5770 Stage Rd, Woodstock, VT 05091

  5770 Stage Rd, Woodstock, VT 05091
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  /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
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  /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
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  $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
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  /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
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  /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
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  /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
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  $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
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  /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
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  /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
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  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
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  /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
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  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
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  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
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  /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
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  /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

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