North Pomfret, 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
/36
$860,000 Sold Aug 11, 2025

61 Putnam Rd, Bridgewater Corners, VT 05035
- 4 Beds
- 1 Bath
- 2,330 Sq Ft
- Built 1865
Last Sold Summary
- 22% Below List Price
- $369/SF
- 367 Days On Market
Current Estimated Value $874,082

Last Listing Agent Geoff Eckler Real Broker LLC

61 Putnam Rd, Bridgewater Corners, VT 05035

/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

/32
$1,295,000 Under Contract
- 2 Beds
- 3.5 Baths
- 2,280 Sq Ft
33 Mountain Ave, Woodstock, VT 05091

Welcome to 33 Mountain Avenue – a mid-century modern gem poised perfectly on the edge of Faulkner Park and at the foot of Mt. Tom and once part of the Marianne Faulkner Estate. The spacious one-level design provides a seamless connection between the indoor and outdoor living space which includes two ensuite bedrooms, living/dining room with fireplace, kitchen, family room, office and attached one

Mary Mayhew Snyder Donegan Real Estate Group

33 Mountain Ave, 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 $777,151

Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

392 Gully Rd, 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

/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
/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 $623,018

Last Listing Agent Nan Carroll Coldwell Banker LIFESTYLES - Hanover

4 Stanton St, 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

/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
/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

/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

/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

/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

/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
/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 $687,297

Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

13 Golf Ave, 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

/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
/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

/27
Est $1,034,422 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
- 88% Above List Price
- $154/SF
- 47 Days On Market
Last Sold Price $550,000

Last Listing Agent Gretchjen Smith 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
/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

/37
Est $895,358 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
- 4% Below List Price
- $519/SF
- 14 Days On Market
Last Sold Price $935,000

Last Listing Agent Marni Rieger KW Vermont-Killington

/43
$1,600,000
- 4 Beds
- 3 Baths
- 6,014 Sq Ft
15 Central St, Woodstock, VT 05091

15 Central Street is one of the finest commercial locations in Woodstock with two of the most creative and successful businesses as the anchor tenants. The property has adapted to changes of the course of its long history of uses including residential shop owner, a barber shop, a dance & pool hall, law office, architectural services and a variety of mercantile endeavors. Notably, the building

Laird Bradley Williamson Group Sothebys Intl. Realty

15 Central St, Woodstock, 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

/38
Est $589,800 Not Listed For Sale

39 South St, Woodstock, VT 05091
- 2 Beds
- 1.5 Baths
- 1,020 Sq Ft
- Built 1869
39 South St, Woodstock, VT 05091

Last Sold Summary
- 24% Above List Price
- $466/SF
- 83 Days On Market
Last Sold Price $475,000

Last Listing Agent Holly Hall Hall Collins Real Estate Group

/41
$1,495,000
- 4 Beds
- 2.5 Baths
- 2,532 Sq Ft
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 Sothebys Intl. Realty

7 Slayton Terrace, Woodstock, VT 05091
/42
$435,000 Sold Apr 01, 2025

773 Hale Hollow Rd, Plymouth, VT 05056
- 2 Beds
- 2 Baths
- 1,514 Sq Ft
- Built 1969
Last Sold Summary
- $287/SF
- 10 Days On Market
Current Estimated Value $486,544

Last Listing Agent Lorien Kelly Kelley Real Estate, Inc.

773 Hale Hollow Rd, Plymouth, VT 05056

/27
Not Listed For Sale

37 South St, Woodstock, VT 05091
- 3 Beds
- 2 Baths
- 1,660 Sq Ft
- Built 1900
37 South St, Woodstock, VT 05091

Last Sold Summary
- 36% Above List Price
- $331/SF
- 4 Days On Market
Last Sold Price $550,000

Last Listing Agent Jennifer Falvey KW Vermont Woodstock

/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
/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 $1,940,202 Not Listed For Sale

2 Border Ln, Woodstock, VT 05091
- 4 Beds
- 6 Baths
- 3,997 Sq Ft
- Built 1984
2 Border Ln, Woodstock, VT 05091

Last Sold Summary
- 10% Below List Price
- $538/SF
- 29 Days On Market
Last Sold Price $2,150,000

Last Listing Agent Jennifer Falvey KW Vermont Woodstock

/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
/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

/39
Est $3,572,648 Not Listed For Sale

3 Church St, Woodstock, VT 05091
- 10 Beds
- 15 Baths
- 10,206 Sq Ft
- Built 1831
3 Church St, Woodstock, VT 05091

Last Sold Summary
- 10% Above List Price
- $319/SF
- 345 Days On Market
Last Sold Price $3,255,000

Last Listing Agent Story Jenks LandVest, Inc/Woodstock

/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
/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 $430,598

Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

37 Atwood Ave, Woodstock, VT 05091

/40
Est $1,557,281 Not Listed For Sale

26 River St, Woodstock, VT 05091
- 6 Beds
- 4 Baths
- 3,719 Sq Ft
- Built 1845
26 River St, Woodstock, VT 05091

Last Sold Summary
- 42% Above List Price
- $296/SF
- 102 Days On Market
Last Sold Price $1,100,000

Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

/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

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