Woodstock, VT Homes

/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

(802) 347-9544

41 Pleasant St, Woodstock, VT 05091
/12
$1,995 per month
- 1 Bed
- 1 Bath
- 1,200 Sq Ft
- Apartment for Rent
36 Happy Valley Rd, Woodstock, VT 05091

This charming first-floor, one-bedroom apartment is located in the grand and historic Four Pillars, a classic Greek Revival home, in the quaint and peaceful hamlet of Taftsville, just outside the village of Woodstock, Vermont. The apartment features high ceilings, large sun-filled windows, and beautiful hardwood floors throughout. The spacious kitchen is fully equipped with modern appliances,

Gail Childs Covered Bridge RE

36 Happy Valley Rd, Woodstock, VT 05091
/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 $758,277

Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

392 Gully Rd, Woodstock, VT 05091

/39
Est $736,850 Not Listed For Sale

6 Highland Ave, Woodstock, VT 05091
- 1 Bed
- 1 Bath
- 1,052 Sq Ft
- Built 1930
6 Highland Ave, Woodstock, VT 05091

Last Sold Summary
- 80% Above List Price
- $390/SF
- 97 Days On Market
Last Sold Price $410,000

Last Listing Agent John Wetmore Wetmore Real Estate

/28
$995,000
- 3 Beds
- 3.5 Baths
- 2,584 Sq Ft
26 Mount Peg Rd Unit C, Woodstock, VT 05091

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

Mary Mayhew Snyder Donegan Real Estate Group

26 Mount Peg Rd Unit C, Woodstock, VT 05091
/25
$3,200 per month
- 2 Beds
- 2 Baths
- 1,536 Sq Ft
- Apartment for Rent
21 Central St, Woodstock, VT 05091

Offered for lease is a luxury apartment in the very heart of Woodstock Village! The elevated location, above the hub of central village shopping, presents captivating views of village activity, as well as distant hills. The owners started with a blank slate, in a previously vacant space and have provided all of the benefits of wall to wall new construction. State of the art mechanical systems

John Wetmore Wetmore Real Estate

21 Central St, Woodstock, VT 05091
/36
$655,000 Sold Nov 24, 2025

4 Stanton St, Woodstock, VT 05091
- 4 Beds
- 2.5 Baths
- 2,124 Sq Ft
- Built 1901
Last Sold Summary
- 18% Above List Price
- $308/SF
- 7 Days On Market
Current Estimated Value $609,874

Last Listing Agent Nan Carroll Coldwell Banker LIFESTYLES - Hanover

4 Stanton St, Woodstock, VT 05091

/50
Est $1,312,882 Not Listed For Sale

1075 Westerdale Rd, Woodstock, VT 05091
- 3 Beds
- 3.5 Baths
- 2,584 Sq Ft
- Built 1985
1075 Westerdale Rd, Woodstock, VT 05091

Last Sold Summary
- 3% Above List Price
- $493/SF
- 72 Days On Market
Last Sold Price $1,275,000

Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

/31
$1,195,000
- 3 Beds
- 3.5 Baths
- 2,385 Sq Ft
26 Mount Peg Rd Unit D, Woodstock, VT 05091

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

Mary Mayhew Snyder Donegan Real Estate Group

26 Mount Peg Rd Unit D, Woodstock, VT 05091
/59
$1,625,000 Sold Oct 24, 2025

7 North St, Woodstock, VT 05091
- 2 Beds
- 3 Baths
- 2,106 Sq Ft
- Built 1880
Last Sold Summary
- 12% Below List Price
- $772/SF
- 111 Days On Market
Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

7 North St, Woodstock, VT 05091

/35
Not Listed For Sale

378 Fletcher Hill Rd, South Woodstock, VT 05071
- 4 Beds
- 1 Bath
- 1,424 Sq Ft
- Built 1971
378 Fletcher Hill Rd, South Woodstock, VT 05071

Last Sold Summary
- $334/SF
- 144 Days On Market
Last Sold Price $475,000

Last Listing Agent John Wetmore Wetmore Real Estate

/41
$1,495,000
- 4 Beds
- 1.5 Baths
7 Slayton Terrace, Woodstock, VT 05091

A rare in-village offering, 7 Slayton Terrace combines walkability, views, and beautifully renovated interiors—just steps from the heart of Woodstock. Sited on an oversized .79-acre lot overlooking Billings Farm, this 4-bedroom home offers the space and flexibility rarely found so close to the village center. The main house features a stunning new kitchen with high-end finishes and beautifully

Keri Cole Williamson Group Sotheby's International Realty

7 Slayton Terrace, 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 $1,591,365

Last Listing Agent John Snyder Snyder Donegan Real Estate Group

441 Spruce Way, Woodstock, VT 05091

/24
Not Listed For Sale

29 Heritage Condos Unit 29D, Woodstock, VT 05091
- 1 Bed
- 1 Bath
- 856 Sq Ft
- Built 1984
29 Heritage Condos Unit 29D, Woodstock, VT 05091

Last Sold Summary
- $269/SF
- 3 Days On Market
Last Sold Price $230,000

Last Listing Agent Franchesca Collins Hall Collins Real Estate Group

/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
/32
$700,000 Sold May 30, 2025

13 Golf Ave, Woodstock, VT 05091
- 2 Beds
- 2 Baths
- 1,520 Sq Ft
- Built 1880
Last Sold Summary
- $461/SF
- 0 Days On Market
Current Estimated Value $673,918

Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

13 Golf Ave, Woodstock, VT 05091

/48
Est $1,131,632 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
- 5% 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

/32
$1,195,000
- 3 Beds
- 3.5 Baths
- 2,592 Sq Ft
26 Mount Peg Rd Unit A, Woodstock, VT 05091

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

Mary Mayhew Snyder Donegan Real Estate Group

26 Mount Peg Rd Unit A, 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 $603,522

Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

187 Dana Rd, Woodstock, VT 05091

/39
Est $1,109,340 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
- 14% Above List Price
- $278/SF
- 207 Days On Market
Last Sold Price $975,000

Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

/31
$995,000
- 3 Beds
- 3.5 Baths
- 2,584 Sq Ft
26 Mount Peg Rd Unit B, Woodstock, VT 05091

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

Mary Mayhew Snyder Donegan Real Estate Group

26 Mount Peg Rd Unit B, Woodstock, VT 05091
/34
$2,210,000 Sold Sep 24, 2025

15 Hathorn Hill Street Extension, Woodstock, VT 05091
- 4 Beds
- 3.5 Baths
- 3,564 Sq Ft
- Built 2009
Last Sold Summary
- 1% Above List Price
- $620/SF
- 68 Days On Market
Last Listing Agent John Snyder Snyder Donegan Real Estate Group

15 Hathorn Hill Street Extension, Woodstock, VT 05091

/35
Est $595,591 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
- $519/SF
- 38 Days On Market
Last Sold Price $595,000

Last Listing Agent David Donegan Snyder Donegan Real Estate Group

/55
$915,000 Under Contract
- 3 Beds
- 3 Baths
- 2,150 Sq Ft
509 Church Hill Rd, Wood Stock, VT 05091

Enjoy in-town ease of living combined with Vermont country charm. This well maintained , efficient home provides first floor living with an additional lower floor ensuite bedroom /sitting area with direct access to lovely grounds and gardens.The light filled home is in excellent condition and is surrounded by fabulous perennial gardens, mature maple trees, raspberry and blueberry bushes ,

Carol Wood Williamson Group Sothebys Intl. Realty

509 Church Hill Rd, Wood Stock, VT 05091
/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

/34
Not Listed For Sale

5 Mountain Ave Unit 4, Woodstock, VT 05091
- 2 Beds
- 2.5 Baths
- 1,590 Sq Ft
- Built 1880
5 Mountain Ave Unit 4, Woodstock, VT 05091

Last Sold Summary
- $550/SF
- 12 Days On Market
Last Sold Price $875,000

Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

/45
$1,299,000
- 8 Beds
- 5 Baths
- 3,814 Sq Ft
7030 U S 4, Bridgewater, VT 05034

Situated between historic Woodstock Vermont and the ski slopes of Killington, 7030 US Route 4 provides easy access to the best amenities of the area. The Property has two separate spaces, a standalone two-level garage with ample storage area below, and sits on 6 acres with direct river access. The "Apartment” first floor has an open design with a kitchen, living area, and tucked away bathroom.

Eric Benvenuti

7030 U S 4, Bridgewater, VT 05034
/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
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

/60
$1,300,000 Under Contract
- 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
/48
$705,000 Sold Nov 26, 2025

25 Linden Hill St, Woodstock, VT 05091
- 3 Beds
- 2 Baths
- 1,694 Sq Ft
- Built 1910
Last Sold Summary
- 11% Below List Price
- $416/SF
- 217 Days On Market
Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

25 Linden Hill St, Woodstock, VT 05091

/34
Not Listed For Sale

7429 Us Route 4, Bridgewater, VT 05034
- 3 Beds
- 2 Baths
- 1,700 Sq Ft
- Built 1800
7429 Us Route 4, Bridgewater, VT 05034

Last Sold Summary
- $253/SF
- 25 Days On Market
Last Sold Price $430,000

Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

/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
/30
$405,000 Sold Feb 17, 2026

37 Atwood Ave, Woodstock, VT 05091
- 2 Beds
- 1 Bath
- 768 Sq Ft
- Built 1960
Last Sold Summary
- 16% Below List Price
- $527/SF
- 152 Days On Market
Current Estimated Value $410,445

Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

37 Atwood Ave, Woodstock, VT 05091

/27
Est $921,981 Not Listed For Sale

7 Golf Ave, Woodstock, VT 05091
- 5 Beds
- 3 Baths
- 3,579 Sq Ft
- Built 1832
7 Golf Ave, Woodstock, VT 05091

Last Sold Summary
- 68% Above List Price
- $154/SF
- 47 Days On Market
Last Sold Price $550,000

Last Listing Agent Gretchjen Smith 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
/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 $1,699,354

Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

2090 Randall Rd, Woodstock, VT 05091

/37
Est $857,905 Not Listed For Sale

13 High St, Woodstock, VT 05091
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
- Built 1900
13 High St, Woodstock, VT 05091

Last Sold Summary
- 8% Below List Price
- $519/SF
- 14 Days On Market
Last Sold Price $935,000

Last Listing Agent Marni Rieger KW Vermont-Killington

/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
/57
$1,710,000 Sold Dec 05, 2025

20 The Green, Woodstock, VT 05091
- 3 Beds
- 2.5 Baths
- 2,688 Sq Ft
- Built 1826
Last Sold Summary
- 14% Below List Price
- $636/SF
- 139 Days On Market
Current Estimated Value $1,747,990

Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

20 The Green, Woodstock, VT 05091

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