Woodstock Town, VT Homes

/46
$8,000,000
- 3 Beds
- 3.5 Baths
- 6,096 Sq Ft
115 Eastman Rd, South Woodstock, VT 05071

Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

Keri Cole Williamson Group Sotheby's International Realty

115 Eastman Rd, South Woodstock, VT 05071
/53
$798,000 Sold Oct 31, 2025

392 Gully Rd, Woodstock, VT 05091
- 2 Beds
- 2 Baths
- 1,308 Sq Ft
- Built 2019
Last Sold Summary
- $610/SF
- 28 Days On Market
Current Estimated Value $777,151

Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

392 Gully Rd, Woodstock, VT 05091

/48
Est $937,772 Not Listed For Sale

5274 W Woodstock Rd, Woodstock, VT 05091
- 2 Beds
- 2 Baths
- 2,058 Sq Ft
- Built 1972
5274 W Woodstock Rd, Woodstock, VT 05091

Last Sold Summary
- 22% Below List Price
- $581/SF
- 15 Days On Market
Last Sold Price $1,195,000

Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

/49
$1,595,000
- 5 Beds
- 3.5 Baths
- 3,648 Sq Ft
1522 Barnard Rd, Woodstock, VT 05091

Just 2 miles from Woodstock Village, this gracious brick cape on 6 open acres offers space, comfort, and classic Vermont charm. The expanded chef’s kitchen opens to a gracious gathering room ideal for entertaining, while 3 fireplaces—wood-burning, brick, and gas-ready—provide cozy warmth throughout. Upstairs, find 3–4 bedrooms including one with its own fireplace, plus a private guest room or

Keri Cole Williamson Group Sothebys Intl. Realty

1522 Barnard Rd, Woodstock, VT 05091
/40
$1,625,000 Sold Sep 29, 2025

441 Spruce Way, Woodstock, VT 05091
- 4 Beds
- 3 Baths
- 2,619 Sq Ft
- Built 1986
Last Sold Summary
- 2% Below List Price
- $620/SF
- 6 Days On Market
Current Estimated Value $1,657,350

Last Listing Agent John Snyder Snyder Donegan Real Estate Group

441 Spruce Way, Woodstock, VT 05091

/39
Est $1,036,603 Not Listed For Sale

433 Cowdrey Path, Woodstock, VT 05091
- 4 Beds
- 4 Baths
- 3,507 Sq Ft
- Built 1986
433 Cowdrey Path, Woodstock, VT 05091

Last Sold Summary
- 6% Above List Price
- $278/SF
- 207 Days On Market
Last Sold Price $975,000

Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

/60
$2,395,000 Pending
- 6 Beds
- 5 Baths
- 3,645 Sq Ft
1362 Barnard Rd, Woodstock, VT 05091

Gilbert’s Hill, the very best of Vermont living - Iconic, 112-acre estate with a storybook history as the first “modern” ski run in the US. Located two miles from the village center of Woodstock, the “prettiest small town in America", experience rural peace with convenient access to great restaurants and shops. Turnkey, fully-restored Vermont farmstead - a picturesque family compound with 7

Chris Lang

1362 Barnard Rd, Woodstock, VT 05091
/22
$618,500 Sold Oct 03, 2025

187 Dana Rd, Woodstock, VT 05091
- 3 Beds
- 1.5 Baths
- 1,468 Sq Ft
- Built 1955
Last Sold Summary
- 8% Below List Price
- $421/SF
- 108 Days On Market
Current Estimated Value $654,016

Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

187 Dana Rd, Woodstock, VT 05091

/35
Est $599,384 Not Listed For Sale

93 Blackbriar Rd, Woodstock, VT 05091
- 2 Beds
- 1 Bath
- 1,146 Sq Ft
- Built 1950
93 Blackbriar Rd, Woodstock, VT 05091

Last Sold Summary
- 1% Above List Price
- $519/SF
- 38 Days On Market
Last Sold Price $595,000

Last Listing Agent David Donegan Snyder Donegan Real Estate Group

/46
$1,425,000
- 5 Beds
- 3.5 Baths
- 3,440 Sq Ft
4946 South Rd, South Woodstock, VT 05071

Iconic 1854 Gothic Revival home, known as the Lilac Cottage is located in the heart of South Woodstock Village, just a short stroll to The Ransom Tavern at Kedron Valley Inn, The South Woodstock Store, and Kedron Pond. Many new state of the art updates and improvements throughout this versatile, turn-key home, all honoring and highlighting the period detail. The rooms are spacious, bright and

Danny Kogut Williamson Group Sothebys Intl. Realty

4946 South Rd, South Woodstock, VT 05071
/60
$1,650,000 Sold Nov 08, 2025

2334 South Rd, Woodstock, VT 05091
- 3 Beds
- 2.5 Baths
- 5,422 Sq Ft
- Built 1972
Last Sold Summary
- 25% Below List Price
- $304/SF
- 94 Days On Market
Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

2334 South Rd, Woodstock, VT 05091

/40
Not Listed For Sale

318 Ebbin Lockwood Way, Woodstock, VT 05071
- 3 Beds
- 3.5 Baths
- 6,047 Sq Ft
- Built 1970
318 Ebbin Lockwood Way, Woodstock, VT 05071

Last Sold Summary
- $455/SF
- 495 Days On Market
Last Sold Price $2,750,000

Last Listing Agent Story Jenks LandVest, Inc/Woodstock

/26
$3,300,000
- 3 Beds
- 4.5 Baths
- 3,682 Sq Ft
249 Sawyer Rd, Woodstock, VT 05091

Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, proximity to town, and access to endless outdoor recreation opportunities. Enjoy the convenience of living close to the shops, cafes, and restaurants of Woodstock, while being tucked away in your own world above. The 3-bedroom primary

Andrew Bustin LandVest, Inc/Woodstock

249 Sawyer Rd, Woodstock, VT 05091
/39
$613,000 Sold Sep 10, 2025

5851 South Rd, Woodstock, VT 05071
- 3 Beds
- 2.5 Baths
- 1,958 Sq Ft
- Built 1920
Last Sold Summary
- 19% Below List Price
- $313/SF
- 302 Days On Market
Last Listing Agent Carol Wood Williamson Group Sothebys Intl. Realty

5851 South Rd, Woodstock, VT 05071

/40
Est $906,980 Not Listed For Sale

3090 South Rd, Woodstock, VT 05091
- 5 Beds
- 5 Baths
- 2,375 Sq Ft
- Built 1884
3090 South Rd, Woodstock, VT 05091

Last Sold Summary
- 22% Above List Price
- $312/SF
- 343 Days On Market
Last Sold Price $742,162

Last Listing Agent John Wetmore Wetmore Real Estate

/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
/44
$1,700,000 Sold Aug 15, 2025

2090 Randall Rd, Woodstock, VT 05091
- 3 Beds
- 2.5 Baths
- 2,423 Sq Ft
- Built 2007
Last Sold Summary
- 6% Below List Price
- $702/SF
- 177 Days On Market
Current Estimated Value $1,767,030

Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

2090 Randall Rd, Woodstock, VT 05091

/37
Est $1,205,905 Not Listed For Sale

326 Hall Cir, Woodstock, VT 05091
- 4 Beds
- 3 Baths
- 1,949 Sq Ft
- Built 1988
326 Hall Cir, Woodstock, VT 05091

Last Sold Summary
- 3% Above List Price
- $603/SF
- 31 Days On Market
Last Sold Price $1,175,000

Last Listing Agent Carol Wood Williamson Group Sothebys Intl. Realty

/57
$1,195,000
- 4 Beds
- 2.5 Baths
- 2,668 Sq Ft
513 Deer Brook Way, Woodstock, VT 05091

Set on a sun-bathed hillside between Woodstock Village and the renowned slopes of Killington and Pico, this custom-built Colonial captures what buyers seek most in Vermont: privacy, craftsmanship, and striking mountain views that feel close enough to touch. Thoughtfully designed by the respected Vermont Vernacular Builders, the home reflects classic regional architecture with refined proportions,

Keri Cole Williamson Group Sothebys Intl. Realty

513 Deer Brook Way, Woodstock, VT 05091
/24
$629,500 Sold Sep 12, 2025

40 Pomfret Rd, Woodstock, VT 05091
- 3 Beds
- 1.5 Baths
- 1,650 Sq Ft
- Built 1885
Last Sold Summary
- $382/SF
- 17 Days On Market
Current Estimated Value $632,015

Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

40 Pomfret Rd, Woodstock, VT 05091

/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
- $907/SF
- 121 Days On Market
Last Sold Price $4,205,000

Last Listing Agent Story Jenks LandVest, Inc/Woodstock

/47
$8,000,000
- 3 Beds
- 3.5 Baths
- 5,384 Sq Ft
115 Eastman Rd, Woodstock, VT 05091

Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

Keri Cole Williamson Group Sothebys Intl. Realty

115 Eastman Rd, Woodstock, VT 05091
/50
$1,275,000 Sold Apr 02, 2025

1075 Westerdale Rd, Woodstock, VT 05091
- 3 Beds
- 3.5 Baths
- 2,584 Sq Ft
- Built 1985
Last Sold Summary
- 9% Below List Price
- $493/SF
- 72 Days On Market
Current Estimated Value $1,374,473

Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

1075 Westerdale Rd, Woodstock, VT 05091

/30
Est $1,284,289 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
- 14% Above List Price
- $408/SF
- 28 Days On Market
Last Sold Price $1,125,000

Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

/57
$817,000 Under Contract
- 3 Beds
- 2 Baths
- 2,760 Sq Ft
616 Rose Hill Rd, Woodstock, VT 05091

This is a rare opportunity to own 10.1 acres of land in a coveted area of Woodstock that includes a 1988 Frizzell Builders house and a detached oversized garage with a second floor for storage . The property was part of the King Farm which is now in Vt. Land Trust as conserved land , until it was split off in the late 1980's when the Colby family came into ownership and built the existing house

Carol Wood Williamson Group Sothebys Intl. Realty

616 Rose Hill Rd, Woodstock, VT 05091
/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 $659,390

Last Listing Agent Scott Monahan Williamson Group Sothebys Intl. Realty

144 Butternut Ln, Woodstock, VT 05091

/40
Not Listed For Sale

5798 South Rd, Woodstock, VT 05071
- 5 Beds
- 6 Baths
- 3,910 Sq Ft
- Built 1850
5798 South Rd, Woodstock, VT 05071

Last Sold Summary
- $512/SF
- 193 Days On Market
Last Sold Price $2,000,000

Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

/11
$190,000
- 2 Beds
- 1.5 Baths
- 1,200 Sq Ft
99 Safford Commons Way, Woodstock, VT 05091

These 1200 sq. ft., 2-bedroom, 1.5-bathroom condos are being sold for less than half of their fair market value! Available for immediate move-in, each condo has an open-concept kitchen, dining room, and living room, which are on the airy and light-filled second floor. There is a small deck off the living room. The two cozy bedrooms are on the first floor. Electricity bills will be offset by solar

Jane Darrach Martha E. Diebold/Hanover

99 Safford Commons Way, Woodstock, VT 05091
/40
$750,000 Sold May 01, 2025

6963 South Rd, Woodstock, VT 05071
- 2 Beds
- 1.5 Baths
- 1,840 Sq Ft
- Built 1970
Last Sold Summary
- 6% Below List Price
- $408/SF
- 43 Days On Market
Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

6963 South Rd, Woodstock, VT 05071

/40
Est $1,409,914 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
- 6% Below List Price
- $644/SF
- 92 Days On Market
Last Sold Price $1,500,000

Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

/11
$779,000
- Land
- 6.46 Acres
- $120,588 per Acre
0 Barnard Rd Unit 20.002, Woodstock, VT 05091

A truly unique 6 acre parcel of land conveniently located in the heart of Woodstock! Tremendous development potential! Zoning allows both COMMERCIAL and RESIDENTIAL use! The 6 acres visually divide into 2 components with 2 diverse personalities. The 1st component is an extraordinary private building lot in the heart of Woodstock! Access to this 4 acre component initially leads through a pleasant

John Wetmore Wetmore Real Estate

0 Barnard Rd Unit 20.002, Woodstock, VT 05091
/51
$1,300,000 Sold Jul 02, 2025

608 Fletcher Hill Rd, Woodstock, VT 05091
- 4 Beds
- 3.5 Baths
- 4,228 Sq Ft
- Built 1980
Last Sold Summary
- 13% Below List Price
- $307/SF
- 91 Days On Market
Current Estimated Value $1,377,111

Last Listing Agent Sandy Reavill Real Broker LLC

608 Fletcher Hill Rd, Woodstock, VT 05091

/32
Est $545,872 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
- 4% Above List Price
- $477/SF
- 1 Day On Market
Last Sold Price $525,000

Last Listing Agent Katherine Burns William Raveis Real Estate Vermont Properties

/11
$149,000 Under Contract
- Land
- 3.54 Acres
- $42,090 per Acre
00 Carlton Hill Rd Unit 27, Woodstock, VT 05091

Discover the beauty of Vermont from this diverse 3.5-acre parcel along Carlton Hill Road, set in a peaceful rural location amid a neighborhood of substantial properties. With level access from a well-maintained town road, this land offers an inviting blend of convenience and natural charm. Just minutes from the vibrant shops, dining, and cultural attractions of Woodstock Village, the property

Sandy Reavill Real Broker LLC

00 Carlton Hill Rd Unit 27, Woodstock, VT 05091
/24
$230,000 Sold Mar 26, 2025

29 Heritage Condos Unit 29D, Woodstock, VT 05091
- 1 Bed
- 1 Bath
- 856 Sq Ft
- Built 1984
Last Sold Summary
- $269/SF
- 3 Days On Market
Last Listing Agent Franchesca Collins Hall Collins Real Estate Group

29 Heritage Condos Unit 29D, Woodstock, VT 05091

/38
Est $1,349,621 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
- 14% Below List Price
- $469/SF
- 112 Days On Market
Last Sold Price $1,570,000

Last Listing Agent Carol Wood Williamson Group Sothebys Intl. Realty

/40
$3,500,000
- 6 Beds
- 6 Baths
- 5,433 Sq Ft
61 Academy Cir, Woodstock, VT 05071

Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The

Carol Wood Williamson Group Sothebys Intl. Realty

61 Academy Cir, Woodstock, VT 05071
/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

/40
Est $455,687 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
- 30% Above List Price
- $255/SF
- 18 Days On Market
Last Sold Price $349,900

Last Listing Agent Daniel Pol Killington Pico Realty

/45
$725,000 Under Contract
- 5 Beds
- 3 Baths
- 3,028 Sq Ft
137 Laughlin Rd, Woodstock, VT 05091

Charming property located just minutes from historic Woodstock Green. The main house first floor features 3 bedrooms/ 1bath with formal dining room, living room and kitchen on first level anchored by an expansive deck for entertaining or enjoying the afternoon sun. Handsome hardwood floors throughout, stainless appliances in the kitchen accented with granite countertops. The lower level is walk

Gretchjen Smith Williamson Group Sothebys Intl. Realty

137 Laughlin Rd, Woodstock, VT 05091

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