Woodstock, VT Homes

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  /40

  Est $655,471 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft

  3256 South Rd, Woodstock, VT 05091

  3256 South Rd, Woodstock, VT 05091
• 

  

  

  /19

  $695,000

  • Land
  • 60.57 Acres
  • $11,474 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
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  /52

  $1,320,000 Sold Jul 25, 2025

  11 College Hill Rd, Woodstock, VT 05091

  • 5 Beds
  • 3.5 Baths
  • 3,953 Sq Ft
  • Built 1919

  Last Sold Summary

  • 5% Below List Price
  • $334/SF
  • 85 Days On Market

  Current Estimated Value $1,137,177

  Last Listing Agent Zoe Hathorn Washburn Snyder Donegan Real Estate Group

  11 College Hill Rd, Woodstock, VT 05091
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  /40

  Est $658,341 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,904 Sq Ft

  588 Kendall Rd, Woodstock, VT 05091

  588 Kendall Rd, Woodstock, VT 05091
• 

  

  

  /43

  $6,100,000 Pending

  • 6 Beds
  • 6 Baths
  • 8,264 Sq Ft

  37 Maxham Rd, Woodstock, VT 05091

  Hawk Gate Farm is a 352-acre estate, roughly square in shape, in the hills of South Pomfret. This storied landscape—once five independent farmsteads—embodies the evolution of rural New England from its earliest post-colonial roots to the present day. At its heart stands the Isaac Newton House, a c.1790 Federal-style brick Cape with preserved period detail. Features include finely crafted

  Story Jenks LandVest, Inc/Woodstock

  37 Maxham Rd, Woodstock, VT 05091
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  /40

  $575,000 Sold May 09, 2025

  105 Happy Valley Rd, Woodstock, VT 05091

  • 3 Beds
  • 1 Bath
  • 1,700 Sq Ft
  • Built 1848

  Last Sold Summary

  • 17% Below List Price
  • $338/SF
  • 274 Days On Market

  Current Estimated Value $565,826

  Last Listing Agent John Bassette Bassette Real Estate Group

  105 Happy Valley Rd, Woodstock, VT 05091
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  /24

  Est $473,052 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,034 Sq Ft

  708 E Woodstock Rd, Woodstock, VT 05091

  708 E Woodstock Rd, Woodstock, VT 05091
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  /32

  $72,999

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  185 Riverbend Way, Woodstock, VT 05091

  Start your Vermont dream with this affordable 3-bedroom, 2-bath mobile home just minutes from downtown Woodstock, VT. Located in a quiet, private community with stunning mountain views and direct river frontage on the Ottauquechee, this home is a rare opportunity to enjoy scenic living at a budget-friendly price. Perfect as a first home, vacation getaway, or investment, this property is also

  Mendi Michael Engel & Völkers Okemo

  185 Riverbend Way, Woodstock, VT 05091
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  /24

  $482,500 Sold Dec 11, 2025

  51 Terrace St, Woodstock, VT 05091

  • 2 Beds
  • 2 Baths
  • 1,237 Sq Ft
  • Built 1870

  Last Sold Summary

  • 4% Below List Price
  • $390/SF
  • 3 Days On Market

  Last Listing Agent Dan Noble Snyder Donegan Real Estate Group

  51 Terrace St, Woodstock, VT 05091
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  /40

  Est $1,369,248 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,042 Sq Ft

  612 Church Hill Rd, Woodstock, VT 05091

  612 Church Hill Rd, Woodstock, VT 05091
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  /60

  $950,000

  • 3 Beds
  • 3 Baths
  • 2,794 Sq Ft

  34 Midsomer Meadows Ln, Woodstock, VT 05091

  Welcome to Starry Hill, a fully furnished Airbnb rental, handcrafted, solid-timber Colonial privately nestled on 18.9 tranquil acres just 5 miles North of Woodstock, built over 4 years by a family of loggers and master craftsmen. This exceptional home features Eastern white pine walls, hemlock structural beams, and pine ceilings/flooring sourced from the property. Warm, inviting living spaces

  John Bassette Bassette Real Estate Group

  34 Midsomer Meadows Ln, Woodstock, VT 05091
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  /37

  $975,000 Sold Jan 10, 2025

  828 Deerbrook Way, Woodstock, VT 05091

  • 4 Beds
  • 3 Baths
  • 2,944 Sq Ft
  • Built 1994

  Last Sold Summary

  • 1% Below List Price
  • $331/SF
  • 28 Days On Market

  Current Estimated Value $950,902

  Last Listing Agent Stan Butler Four Seasons Sotheby's Int'l Realty

  828 Deerbrook Way, Woodstock, VT 05091
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  /14

  Est $670,522 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,656 Sq Ft

  16 Pomfret Rd, Woodstock, VT 05091

  16 Pomfret Rd, Woodstock, VT 05091
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  /48

  $795,000

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

  598 E Woodstock Rd, Woodstock, VT 05091

  Discover the charm of historic Woodstock, Vermont in this spacious, light-filled home just minutes from the village green. Blending timeless New England character with modern comfort, this property offers an abundance of space and versatility — ideal as a full-time residence or a relaxing ski-season getaway.This inviting home features hardwood floors, custom cherry built-ins, and two fireplaces,

  Erika Smith RE/MAX Upper Valley

  598 E Woodstock Rd, Woodstock, VT 05091
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  /37

  $925,000 Sold Jul 31, 2025

  4 River St, Woodstock, VT 05091

  • 2 Beds
  • 2.5 Baths
  • 2,176 Sq Ft
  • Built 1847

  Last Sold Summary

  • 7% Below List Price
  • $425/SF
  • 68 Days On Market

  Current Estimated Value $891,759

  Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

  4 River St, Woodstock, VT 05091
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  /15

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 934 Sq Ft

  13 Park View Way Unit 31, Woodstock, VT 05091

  13 Park View Way Unit 31, Woodstock, VT 05091
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  /59

  $18,000,000

  • 7 Beds
  • 10 Baths
  • 12,520 Sq Ft

  355 Greene Rd, Woodstock, VT 05071

  Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and

  Chris Lang

  355 Greene Rd, Woodstock, VT 05071
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  /28

  $239,000 Sold Sep 11, 2025

  42 Heritage Condo Way Unit 16, Woodstock, VT 05091

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

  Last Sold Summary

  • 4% Below List Price
  • $293/SF
  • 15 Days On Market

  Last Listing Agent Franchesca Collins Hall Collins Real Estate Group

  42 Heritage Condo Way Unit 16, Woodstock, VT 05091
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  /22

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,013 Sq Ft

  7 Park View Way Unit 32, Woodstock, VT 05091

  7 Park View Way Unit 32, Woodstock, VT 05091
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  /24

  $3,300,000

  • 3 Beds
  • 4.5 Baths
  • 3,682 Sq Ft

  249 Sawyer Rd, Woodstock, VT 05091

  Tucked away just minutes from the shops, cafes, and restaurants of Woodstock Village, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, family gatherings, and endless outdoor recreation opportunities nearby. The 3-bedroom primary residence is perfectly sited to overlook Woodstock’s iconic Mount Tom and the Marsh-Billings Musuem, Vermont’s only National

  Andrew Bustin LandVest, Inc/Woodstock

  249 Sawyer Rd, Woodstock, VT 05091
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  /39

  $410,000 Sold Apr 01, 2025

  6 Highland Ave, Woodstock, VT 05091

  • 1 Bed
  • 1 Bath
  • 1,052 Sq Ft
  • Built 1930

  Last Sold Summary

  • 9% Below List Price
  • $390/SF
  • 97 Days On Market

  Current Estimated Value $733,864

  Last Listing Agent John Wetmore Wetmore Real Estate

  6 Highland Ave, Woodstock, VT 05091
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  /27

  Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,666 Sq Ft

  2411 Chateauguay Rd, Woodstock, VT 05091

  2411 Chateauguay Rd, Woodstock, VT 05091
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  /60

  $230,000

  • 1 Bed
  • 1 Bath
  • 856 Sq Ft

  42 Heritage Condo Way Unit 14D, Woodstock, VT 05091

  Welcome to your Woodstock affordable retreat! This inviting, end-unit, two-level townhouse in the sought-after Heritage Condominium community is nestled on a dead-end road just minutes west of the historic village of Woodstock. This bright 856 sq/ft two-level home offers an open-concept first floor with a carpeted living/dining area warmed by Empire gas heat (plus electric backup). From this

  John Bassette Bassette Real Estate Group

  42 Heritage Condo Way Unit 14D, Woodstock, VT 05091
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  /44

  $1,900,000 Sold Sep 05, 2025

  51 Watkins Way Unit 2, Woodstock, VT 05091

  • 3 Beds
  • 2.5 Baths
  • 3,227 Sq Ft
  • Built 2021

  Last Sold Summary

  • $589/SF
  • 0 Days On Market

  Current Estimated Value $1,853,163

  Last Listing Agent John King Real Broker LLC

  51 Watkins Way Unit 2, Woodstock, VT 05091
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  /28

  Est $1,486,068 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,836 Sq Ft

  4411 Church Hill Rd, Woodstock, VT 05091

  4411 Church Hill Rd, Woodstock, VT 05091
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  /7

  $325,000

  • Land
  • 8 Acres
  • $40,625 per Acre

  1 Carlton Hill Rd, Woodstock, VT 05091

  Sweet Spot - 8 acre building lot located within minutes of the Woodstock Village Green! Driveway is in place and a lovely building site has been cleared and power is at site. Wonderful opportunity to build your Vermont getaway or primary residence. Enjoy access to four season recreation, Marsh-Billings-Rockefeller National Park, theatre, arts, dining, shopping and a short commute to all

  Mary Mayhew Snyder Donegan Real Estate Group

  1 Carlton Hill Rd, Woodstock, VT 05091
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  /40

  $2,425,000 Sold Aug 15, 2025

  739 Westerdale Rd, Woodstock, VT 05091

  • 4 Beds
  • 4.5 Baths
  • 5,017 Sq Ft
  • Built 2003

  Last Sold Summary

  • $483/SF
  • 0 Days On Market

  Current Estimated Value $2,630,291

  Last Listing Agent John Snyder Snyder Donegan Real Estate Group

  739 Westerdale Rd, Woodstock, VT 05091
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  /40

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,411 Sq Ft

  1106 Church Hill Rd, Woodstock, VT 05091

  1106 Church Hill Rd, Woodstock, VT 05091
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  /58

  $825,000 Under Contract

  • 4 Beds
  • 4 Baths
  • 3,184 Sq Ft

  256 Barnard Rd, Woodstock, VT 05091

  Discover the charm of historic Woodstock in this beautifully maintained late-1800s residence, set on just over an acre of flat, open lawn and ideally located within walking distance to the village. Bordering the scenic Billings Farm & Museum, this 4-bedroom home blends timeless New England character with thoughtful modern updates.Inside, you’ll find light-filled living spaces, a

  Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

  256 Barnard Rd, Woodstock, VT 05091
• 

  

  /31

  $684,000 Sold Oct 10, 2025

  13 Slayton Terrace, Woodstock, VT 05091

  • 3 Beds
  • 3 Baths
  • 1,550 Sq Ft
  • Built 1920

  Last Sold Summary

  • 13% Below List Price
  • $441/SF
  • 162 Days On Market

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  13 Slayton Terrace, Woodstock, VT 05091
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  /26

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,250 Sq Ft

  317 Bridgewater Hollow Road Extension Unit 7-035, Woodstock, VT 05091

  317 Bridgewater Hollow Road Extension Unit 7-035, Woodstock, VT 05091
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  /8

  $650,000 Under Contract

  • Land
  • 2.41 Acres
  • $269,710 per Acre

  2 Highland Ave, Woodstock, VT 05091

  An extraordinary opportunity to acquire a private building parcel overlooking the Marsh Billings Rockefeller National Park, Billing's Farm to the Connecticut River Valley in Woodstock Village. The secluded, elevated parcel combines an early homesite and a productive hayfield mowed by a family member within living memory. The access is level and intersects Highland Avenue with an extended line of

  Laird Bradley Williamson Group Sothebys Intl. Realty

  2 Highland Ave, Woodstock, VT 05091
• 

  

  /31

  $475,000 Sold Jun 16, 2025

  85 Townhouse Way Unit 18, Woodstock, VT 05091

  • 2 Beds
  • 3 Baths
  • 2,091 Sq Ft
  • Built 1978

  Last Sold Summary

  • 2% Below List Price
  • $227/SF
  • 29 Days On Market

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  85 Townhouse Way Unit 18, Woodstock, VT 05091
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  /40

  Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,152 Sq Ft

  21 Townhouse Way, Woodstock, VT 05091

  21 Townhouse Way, Woodstock, VT 05091
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  /60

  $1,300,000

  • 4 Beds
  • 5 Baths
  • 3,195 Sq Ft

  125 Shurtleff Ln, Woodstock, VT 05091

  Beautifully sited just a short walk from Woodstock Village, this 2015 custom-built home blends modern comfort with timeless Vermont charm. Thoughtfully designed for everyday living and entertaining, the main level features an open, light-filled layout, a well-appointed kitchen, and seamless access to a sunny three-season room overlooking the landscaped grounds. The sought-after first-floor

  Keri Cole Williamson Group Sothebys Intl. Realty

  125 Shurtleff Ln, Woodstock, VT 05091
• 

  

  /18

  $230,000 Sold Oct 15, 2025

  56 Heritage Condo Way Unit 9, Woodstock, VT 05091

  • 1 Bed
  • 1 Bath
  • 856 Sq Ft
  • Built 1989

  Last Sold Summary

  • 8% Below List Price
  • $269/SF
  • 40 Days On Market

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  56 Heritage Condo Way Unit 9, Woodstock, VT 05091
• 

  

  /20

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,045 Sq Ft

  12 Linden Hill St, Woodstock, VT 05091

  12 Linden Hill St, Woodstock, VT 05091
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  /42

  $1,499,000

  • Land
  • 4.57 Acres
  • $328,009 per Acre

  458 Woodstock Rd, Wood Stock, VT 05091

  It has been said that the highest and best use of this landmark Woodstock property would be a combination of constructing multiple residential units, in the private rear acreage, and commercial development, of the highly visible Route 4 road frontage. There is no question of the unlimited potential! Highly visible! Well located, on the East End entrance route to Woodstock Village! This property

  John Wetmore Wetmore Real Estate

  458 Woodstock Rd, Wood Stock, VT 05091
• 

  

  /35

  $1,650,000 Sold Nov 24, 2025

  10 College Hill Rd, Woodstock, VT 05091

  • 5 Beds
  • 4.5 Baths
  • 4,214 Sq Ft
  • Built 1916

  Last Sold Summary

  • 17% Below List Price
  • $392/SF
  • 79 Days On Market

  Last Listing Agent John Snyder Snyder Donegan Real Estate Group

  10 College Hill Rd, Woodstock, VT 05091
• 

  

  /17

  Est $1,124,264 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,798 Sq Ft

  4651 Cloudland Rd, Woodstock, VT 05091

  4651 Cloudland Rd, Woodstock, VT 05091

Showing Results 121 - 160, Page 4 of 18