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Woodstock

What To Know About Woodstock, Vermont

Widely recognized as "one of the prettiest small towns in America," Woodstock, Vermont was chartered in 1761, more than 15 years before the United States of America signed the Declaration of Independence.

As the Shire Town of Windsor County, Woodstock became a hub for all things related to Vermont business and the law with the county court seated on the Village Green and early entrepreneurs flocking to the opportunity that the land provided. Some of the earliest manufacturers, craftsmen, and artisans, started their trades in Woodstock and the small village quickly became one of the largest towns in the state.

Historic and architecturally important buildings surrounding the central square, known as The Green, include the 1880s pink sandstone Norman Williams Public Library. Just north, Billings Farm & Museum is a functioning dairy farm, with an 1890 farmhouse and exhibits re-creating 19th-century farm life. Hiking and snowshoeing trails lace the Marsh-Billings-Rockefeller National Historical Park. World-class recreational amenities in the area include skiing, hiking, fishing, and golf.

Today, Woodstock continues to honor its history and sense of place through a strong connection to conservation and the farm-to-table movement. Local artisans of all kinds add to a culture that celebrates a combination of historic American charm, outdoor recreation, boutique shopping, fine dining, and a thriving year-round community. Woodstock area real estate includes charming homes on compact lots in the village, and farms and larger parcels outside of town. Scroll down to explore Woodstock VT real estate and find current homes for sale; and on the HT Blog here.



Min. Price
Max. Price
Beds
Baths

355 Greene Road
Woodstock, VT 05071
$18,000,000

7 Beds


5 | 5 Baths


12,520 SqFt


Listing No. 5066210





Property Type: House


camera
Virtual Tour


camera
(59)

Details

115 Eastman Road
Woodstock, VT 05071
$8,000,000

3 Beds


3 | 1 Baths


5,384 SqFt


Listing No. 5039451





Property Type: House


camera
Virtual Tour


camera
(47)

Details

412 Skyland Lane
Woodstock, VT 05091
$6,750,000

4 Beds


4 | 1 Baths


5,087 SqFt


Listing No. 5044620





Property Type: House


camera
Virtual Tour


camera
(48)

Details

249 Sawyer Road
Woodstock, VT 05091
$3,300,000

3 Beds


1 | 4 Baths


3,682 SqFt


Listing No. 5072035





Property Type: House


camera
Virtual Tour


camera
(28)

Details

61 Academy Circle
Woodstock, VT 05071
$2,950,000

6 Beds


2 | 4 Baths


5,433 SqFt


Listing No. 5002873





Property Type: House


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Virtual Tour


camera
(40)

Details

41 Pleasant Street
Woodstock, VT 05091
$2,599,000

9 Beds


11 Baths


5,993 SqFt


Listing No. 5062350





Property Type: House


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Virtual Tour


camera
(54)

Details

39 Elm Street #B
Woodstock, VT 05091
$1,600,000

3 Beds


1 | 3 Baths


3,294 SqFt


Listing No. 5076786





Property Type: Condo


camera
(48)

Details

1522 Barnard Road
Woodstock, VT 05091
$1,595,000

5 Beds


3 | 1 Baths


3,648 SqFt


Listing No. 5050043





Property Type: House


camera
Virtual Tour


camera
(49)

Details

7 Slayton Terrace
Woodstock, VT 05091
$1,495,000

4 Beds


1 | 2 Baths


2,532 SqFt


Listing No. 5049535





Property Type: House


camera
Virtual Tour


camera
(41)

Details

26 Mt Peg Road #D
Woodstock, VT 05091
$1,195,000

3 Beds


3 | 1 Baths


2,385 SqFt


Listing No. 5065225





Property Type: Condo


camera
Virtual Tour


camera
(31)

Details

26 Mt Peg Road #A
Woodstock, VT 05091
$1,195,000

3 Beds


3 | 1 Baths


2,592 SqFt


Listing No. 5065227





Property Type: Condo


camera
Virtual Tour


camera
(32)

Details

513 Deer Brook Way
Woodstock, VT 05091
$1,195,000

4 Beds


2 | 1 Baths


2,668 SqFt


Listing No. 5077012





Property Type: House


camera
Virtual Tour


camera
(57)

Details

 355 Greene Road, Woodstock, VT 05071


camera
VIRTUAL TOUR


camera
(59)

price

$18,000,000

beds

7
7 Beds

baths

5 | 5
5 | 5 Baths

lot size

12,520 SqFt
12,520 SqFt

listing no.

5066210
Listing No. 5066210

property type

House
Property Type: House

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(59)

 115 Eastman Road, Woodstock, VT 05071


camera
VIRTUAL TOUR


camera
(47)

price

$8,000,000

beds

3
3 Beds

baths

3 | 1
3 | 1 Baths

lot size

5,384 SqFt
5,384 SqFt

listing no.

5039451
Listing No. 5039451

property type

House
Property Type: House

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(47)

 412 Skyland Lane, Woodstock, VT 05091


camera
VIRTUAL TOUR


camera
(48)

price

$6,750,000

beds

4
4 Beds

baths

4 | 1
4 | 1 Baths

lot size

5,087 SqFt
5,087 SqFt

listing no.

5044620
Listing No. 5044620

property type

House
Property Type: House

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(48)

 249 Sawyer Road, Woodstock, VT 05091


camera
VIRTUAL TOUR


camera
(28)

price

$3,300,000

beds

3
3 Beds

baths

1 | 4
1 | 4 Baths

lot size

3,682 SqFt
3,682 SqFt

listing no.

5072035
Listing No. 5072035

property type

House
Property Type: House

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(28)

 61 Academy Circle, Woodstock, VT 05071


camera
VIRTUAL TOUR


camera
(40)

price

$2,950,000

beds

6
6 Beds

baths

2 | 4
2 | 4 Baths

lot size

5,433 SqFt
5,433 SqFt

listing no.

5002873
Listing No. 5002873

property type

House
Property Type: House

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(40)

 41 Pleasant Street, Woodstock, VT 05091


camera
VIRTUAL TOUR


camera
(54)

price

$2,599,000

beds

9
9 Beds

baths

11
11 Baths

lot size

5,993 SqFt
5,993 SqFt

listing no.

5062350
Listing No. 5062350

property type

House
Property Type: House

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(54)

 39 Elm Street #B, Woodstock, VT 05091


camera
(48)

price

$1,600,000

beds

3
3 Beds

baths

1 | 3
1 | 3 Baths

lot size

3,294 SqFt
3,294 SqFt

listing no.

5076786
Listing No. 5076786

property type

Condo
Property Type: Condo

gallery photos


camera
(48)

 1522 Barnard Road, Woodstock, VT 05091


camera
VIRTUAL TOUR


camera
(49)

price

$1,595,000

beds

5
5 Beds

baths

3 | 1
3 | 1 Baths

lot size

3,648 SqFt
3,648 SqFt

listing no.

5050043
Listing No. 5050043

property type

House
Property Type: House

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(49)

 7 Slayton Terrace, Woodstock, VT 05091


camera
VIRTUAL TOUR


camera
(41)

price

$1,495,000

beds

4
4 Beds

baths

1 | 2
1 | 2 Baths

lot size

2,532 SqFt
2,532 SqFt

listing no.

5049535
Listing No. 5049535

property type

House
Property Type: House

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(41)

 26 Mt Peg Road #D, Woodstock, VT 05091


camera
VIRTUAL TOUR


camera
(31)

price

$1,195,000

beds

3
3 Beds

baths

3 | 1
3 | 1 Baths

lot size

2,385 SqFt
2,385 SqFt

listing no.

5065225
Listing No. 5065225

property type

Condo
Property Type: Condo

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(31)

 26 Mt Peg Road #A, Woodstock, VT 05091


camera
VIRTUAL TOUR


camera
(32)

price

$1,195,000

beds

3
3 Beds

baths

3 | 1
3 | 1 Baths

lot size

2,592 SqFt
2,592 SqFt

listing no.

5065227
Listing No. 5065227

property type

Condo
Property Type: Condo

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(32)

 513 Deer Brook Way, Woodstock, VT 05091


camera
VIRTUAL TOUR


camera
(57)

price

$1,195,000

beds

4
4 Beds

baths

2 | 1
2 | 1 Baths

lot size

2,668 SqFt
2,668 SqFt

listing no.

5077012
Listing No. 5077012

property type

House
Property Type: House

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(57)

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real Page 4/19 PrimeMLS-016 Rev. R Effective 09/16/2025 - PrimeMLS Confidential estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers? personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information.
Mortgage calculator source: iHomefinder. Schools info source: GreatSchools. WalkScore source: WalkScore. Line Graph details: iHomefinder. Market Report Source: iHomefinder with data from PrimeMLS, Inc.
PrimeMLS data last updated at March 18, 2026, 5:01 AM ET

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