Woodstock, VT Homes

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  /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 $783,735

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

  339 Gully Rd, Woodstock, VT 05091
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  /40

  Est $1,463,148 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,329 Sq Ft

  282 Fletcher Hill Rd, Woodstock, VT 05091

  282 Fletcher Hill Rd, Woodstock, VT 05091
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  /24

  $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. Seven miles into Woodstock Village.

  Matthew Spittle Vermont Horse Country Real Estate

  0 South Rd, Woodstock, VT 05071
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  /17

  $86,500 Sold May 16, 2025

  132 Riverbend Way, Woodstock, VT 05091

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 2011

  Last Sold Summary

  • 13% Below List Price
  • $77/SF
  • 86 Days On Market

  Last Listing Agent Jenna Luce RE/MAX Upper Valley

  132 Riverbend Way, Woodstock, VT 05091
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  /40

  Est $2,214,056 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,604 Sq Ft

  26 The Green, Wood Stock, VT 05091

  26 The Green, Wood Stock, VT 05091
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  /50

  $895,000 Under Contract

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

  100 Pomfret Rd, Woodstock, VT 05091

  Charming, Unique, and Ideally Located! Welcome to 100 Pomfret Road—a beautifully updated farmhouse set on four level, picturesque acres just a short walk from Mt. Tom, Billings Farm, and the heart of downtown Woodstock. This rare find blends timeless character with everyday convenience in a peaceful, brookside setting. Inside, you’ll find a sun-drenched home featuring four bedrooms, two full

  Keri Cole Williamson Group Sothebys Intl. Realty

  100 Pomfret Rd, Woodstock, VT 05091
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  /25

  $525,000 Sold Oct 16, 2025

  19 Prospect St, Wood Stock, VT 05091

  • 2 Beds
  • 2 Baths
  • 1,482 Sq Ft
  • Built 1970

  Last Sold Summary

  • $354/SF
  • 2 Days On Market

  Last Listing Agent Katie McFadden RE/MAX North Professionals

  19 Prospect St, Wood Stock, VT 05091
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  /34

  Est $542,581 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,196 Sq Ft

  1782 South Rd, Woodstock, VT 05091

  1782 South Rd, Woodstock, VT 05091
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  /42

  $1,250,000

  • 4 Beds
  • 2.5 Baths
  • 2,668 Sq Ft

  513 Deer Brook Way Unit Lot 16, Woodstock, VT 05091

  This traditional New England Colonial, designed and custom built by Vermont Vernacular Builders, is sited to capture idyllic all-around mountain views and southern light. The spacious four-bedroom home features wide board floors, exposed beams, and a sun-filled chef’s kitchen and den. New Thor stainless steel 48" propane range installed October 2025.Privately set on over 8 acres, the property

  Chris Crowe Quechee Lakes Real Estate Center

  513 Deer Brook Way Unit Lot 16, Woodstock, VT 05091
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  /43

  $2,350,000 Sold Dec 08, 2025

  2 Pleasant St, Woodstock, VT 05091

  • 4 Beds
  • 3.5 Baths
  • 3,998 Sq Ft
  • Built 1821

  Last Sold Summary

  • 10% Below List Price
  • $588/SF
  • 21 Days On Market

  Last Listing Agent David Donegan Snyder Donegan Real Estate Group

  2 Pleasant St, Woodstock, VT 05091
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  /33

  Est $534,263 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,059 Sq Ft

  11 Church St Unit 2, Woodstock, VT 05091

  11 Church St Unit 2, Woodstock, VT 05091
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  /49

  $785,000

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft

  37 South St, Woodstock, VT 05091

  New price! Welcome to this beautifully renovated residence in the vibrant heart of Woodstock Village. Enjoy unparalleled convenience with a short stroll to the Elementary School, Woodstock Inn, the picturesque Green, and an array of charming shops, restaurants, and bakeries that define village living. Nestled directly across from Vail Field, this home offers easy access to playgrounds, ball

  Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  37 South St, Woodstock, VT 05091
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  /42

  $1,580,000 Sold Dec 30, 2024

  33 River St, Woodstock, VT 05091

  • 4 Beds
  • 4 Baths
  • 4,378 Sq Ft
  • Built 1886

  Last Sold Summary

  • 7% Below List Price
  • $361/SF
  • 79 Days On Market

  Current Estimated Value $1,504,749

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  33 River St, Woodstock, VT 05091
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  /38

  Est $1,437,592 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,350 Sq Ft

  2876 Hartland Hill Rd, Woodstock, VT 05091

  2876 Hartland Hill Rd, Woodstock, VT 05091
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  /9

  $275,000

  • Land
  • 0.43 Acre
  • $639,535 per Acre

  1054 W Woodstock Rd, Woodstock, VT 05091

  Ideally located parcel across West Woodstock Road from the Woodstock Farmers Market and 500 yards from the entry to Woodstock Union Middle & High School. Public water and sewer available with access off Prosper Road near the junction of US Road Route 4/West Woodstock Road. Building plans available. Multi-unit housing development potential in zero vacancy environment.

  Laird Bradley Williamson Group Sothebys Intl. Realty

  1054 W Woodstock Rd, Woodstock, VT 05091
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  /39

  $730,000 Sold Sep 26, 2025

  17 Golf Pond, Woodstock, VT 05091

  • 3 Beds
  • 2.5 Baths
  • 1,850 Sq Ft
  • Built 1987

  Last Sold Summary

  • 6% Below List Price
  • $395/SF
  • 43 Days On Market

  Last Listing Agent Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

  17 Golf Pond, Woodstock, VT 05091
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  /40

  Est $428,362 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,374 Sq Ft

  1880 South Rd, Woodstock, VT 05091

  1880 South Rd, Woodstock, VT 05091
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  /40

  $725,000

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

  3914 South Rd, Woodstock, VT 05091

  This South Woodstock contemporary residence was designed by the original architect-owner to showcase Vermont’s changing seasons and capture views of the Kedron Brook as it wanders through the property past small meadows tucked in along the banks. The home can be accessed privately at grade level through the heated garage and mudroom, while guests enter via a covered entry to the upper level.

  Laird Bradley Williamson Group Sothebys Intl. Realty

  3914 South Rd, Woodstock, VT 05091
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  /36

  $1,300,000 Sold Nov 20, 2025

  13 College Hill Rd, Woodstock, VT 05091

  • 4 Beds
  • 3.5 Baths
  • 3,192 Sq Ft
  • Built 1985

  Last Sold Summary

  • 4% Below List Price
  • $407/SF
  • 12 Days On Market

  Last Listing Agent Dail Frates Snyder Donegan Real Estate Group

  13 College Hill Rd, Woodstock, VT 05091
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  /44

  Est $474,185 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 768 Sq Ft

  2115 E Woodstock Rd, Woodstock, VT 05091

  2115 E Woodstock Rd, Woodstock, VT 05091
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  /58

  $549,000

  • Land
  • 20.2 Acres
  • $27,178 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

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  00 Long Hill Rd, Woodstock, VT 05071
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  /33

  $776,000 Sold Aug 25, 2025

  3 Hathorn Hill St Unit 3, Woodstock, VT 05091

  • 3 Beds
  • 3 Baths
  • 2,552 Sq Ft
  • Built 1984

  Last Sold Summary

  • 1% Above List Price
  • $304/SF
  • 6 Days On Market

  Current Estimated Value $777,506

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  3 Hathorn Hill St Unit 3, Woodstock, VT 05091
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  /26

  Est $1,361,707 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,443 Sq Ft

  76 Grove Hill Rd, Woodstock, VT 05091

  76 Grove Hill Rd, Woodstock, VT 05091
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  /42

  $425,000

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft

  1079 Fletcher Hill Rd, Woodstock, VT 05071

  This charming 2-bedroom ranch house offers a nice layout for main floor living. Features include a sunroom entrance, two bedrooms, a full bath, laundry room, and a main living/dining area with a kitchen, all within a rural setting with ample natural light, local views, and a deck. Recent updates include a primary bedroom ensuite featuring a custom walk-in shower and double sinks, new flooring, a

  Terry Davis Williamson Group Sothebys Intl. Realty

  1079 Fletcher Hill Rd, Woodstock, VT 05071
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  /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
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  /37

  Est $3,342,064 Not Listed For Sale

  • 6 Beds
  • 6.5 Baths
  • 4,700 Sq Ft

  592 Quinn Rd, Woodstock, VT 05091

  592 Quinn Rd, Woodstock, VT 05091
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  /33

  $595,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,555 Sq Ft

  35 Mountain Ave, Woodstock, VT 05091

  Prime In-Village location on Mountain Avenue just steps to Faulkner Park, The Mt Tom trail system and Woodstock Rec Center. This classic New England duplex (eastern side) home serves perfectly as a full time residence, or an easy keep as a second home. Through a classic covered porch enter the foyer with gleaming hardwood floors and high ceilings. The spacious living room has a propane stove, and

  Danny Kogut Williamson Group Sothebys Intl. Realty

  35 Mountain Ave, Woodstock, VT 05091
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  /55

  $1,145,000 Sold Aug 15, 2025

  2 Maple St, Woodstock, VT 05091

  • 4 Beds
  • 3.5 Baths
  • 2,710 Sq Ft
  • Built 2020

  Last Sold Summary

  • 5% Above List Price
  • $423/SF
  • 5 Days On Market

  Current Estimated Value $1,089,632

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  2 Maple St, Woodstock, VT 05091
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  /40

  Est $864,664 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,844 Sq Ft

  917 Carlton Hill Rd, Woodstock, VT 05091

  917 Carlton Hill Rd, Woodstock, VT 05091
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  /42

  $3,500,000

  • 6 Beds
  • 8 Baths
  • 5,142 Sq Ft

  18 The Green, Woodstock, VT 05091

  Conveniently located on the southwest side of the picturesque Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town’s finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication, functionality, modern comfort

  Danny Kogut Williamson Group Sothebys Intl. Realty

  18 The Green, Woodstock, VT 05091
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  /39

  $740,000 Sold Oct 21, 2025

  1082 Greengate Rd, Woodstock, VT 05091

  • 3 Beds
  • 2.5 Baths
  • 1,878 Sq Ft
  • Built 1992

  Last Sold Summary

  • 5% Below List Price
  • $394/SF
  • 32 Days On Market

  Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

  1082 Greengate Rd, Woodstock, VT 05091
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  /40

  Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 6,799 Sq Ft

  587 Old River Rd, Woodstock, VT 05091

  587 Old River Rd, Woodstock, VT 05091
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  /60

  $1,750,000

  • 4 Beds
  • 3.5 Baths
  • 5,000 Sq Ft

  2706 E Woodstock Rd, Woodstock, VT 05091

  INVESTMENT & RESIDENTIAL OPPORTUNITY - Rare historic building (The Taftsville Country Store - Woodstock VT) available for owner occupancy with multiple additional income units in the village of Taftsville. Just five minutes to the quintessential downtown New England Village of Woodstock! Property includes storefront space (approved for restaurant, café, or retail store), Post Office (with current

  John Bassette Bassette Real Estate Group

  2706 E Woodstock Rd, Woodstock, VT 05091
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  /14

  $245,000 Sold Jan 21, 2025

  1340 Oxbow Rd, Woodstock, VT 05091

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft
  • Built 2017

  Last Sold Summary

  • 18% Below List Price
  • $445/SF
  • 24 Days On Market

  Last Listing Agent Ara Cardew BHG Masiello Keene

  1340 Oxbow Rd, Woodstock, VT 05091
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  /38

  Est $817,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft

  506 Westerdale Rd, Woodstock, VT 05091

  506 Westerdale Rd, Woodstock, VT 05091
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  /27

  $650,000 Under Contract

  • Land
  • 77.7 Acres
  • $8,366 per Acre

  0 Mecawee Rd, Woodstock, VT 05091

  Spectacular 77+ acre parcel on sought after Mecawee Rd. with a perfect combination of level, sloping and hilly terrain. There are multiple building sites including a large cleared area set back off the road with a driveway in place and utilities (electric & fiber optic) at the street. This past Fall, the Sellers went to great lengths to clear the land all the way down to the road opening up

  Dan Noble Snyder Donegan Real Estate Group

  0 Mecawee Rd, Woodstock, VT 05091
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  /54

  $1,300,000 Sold Nov 05, 2025

  687 S Perry Rd, Woodstock, VT 05091

  • 5 Beds
  • 4.5 Baths
  • 4,617 Sq Ft
  • Built 1970

  Last Sold Summary

  • 26% Below List Price
  • $282/SF
  • 107 Days On Market

  Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

  687 S Perry Rd, Woodstock, VT 05091
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  /6

  Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,310 Sq Ft

  7 Hathorn Hill Unit 7, Woodstock, VT 05091

  7 Hathorn Hill Unit 7, Woodstock, VT 05091
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  /54

  $2,599,000

  • 9 Beds
  • 11 Baths
  • 5,993 Sq Ft

  41 Pleasant St, Woodstock, VT 05091

  This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont’s most beloved communities. Woodstock is often hailed as “the prettiest small town in America,” and for good reason. The village is a vibrant resort town with

  Jennifer Falvey KW Vermont Woodstock

  41 Pleasant St, Woodstock, VT 05091
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  /41

  $1,075,000 Sold Jul 15, 2025

  119 English Mills Way, Woodstock, VT 05091

  • 5 Beds
  • 4.5 Baths
  • 4,698 Sq Ft
  • Built 1985

  Last Sold Summary

  • 26% Below List Price
  • $229/SF
  • 353 Days On Market

  Current Estimated Value $1,004,417

  Last Listing Agent John Wetmore Wetmore Real Estate

  119 English Mills Way, Woodstock, VT 05091

Showing Results 81 - 120, Page 3 of 18