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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. Select the Property Search tab to explore Woodstock VT real estate and find current homes for sale; and on the HT Blog here.



Min. Price
Max. Price
Beds
Baths

234 Randall Road
Woodstock, VT 05091
$845,000

2 Beds


1 Baths


600 SqFt


Listing No. 4913852





Property Type: House


camera
(14)

Details

25 Linden Hill Street
Woodstock, VT 05091
$795,000

3 Beds


1 | 1 Baths


1,694 SqFt


Listing No. 5028831





Property Type: House


camera
Virtual Tour


camera
(48)

Details

339 Gully Road
Woodstock, VT 05091
$775,000

4 Beds


1 | 2 Baths


2,688 SqFt


Listing No. 5037463





Property Type: House


camera
(40)

Details

17 Golf Avenue
Woodstock, VT 05091
$775,000

3 Beds


1 | 2 Baths


1,850 SqFt


Listing No. 5043286





Property Type: House


camera
Virtual Tour


camera
(39)

Details

13 Slayton Terrace
Woodstock, VT 05091
$755,000

3 Beds


0 | 3 Baths


1,550 SqFt


Listing No. 5033279





Property Type: House


camera
Virtual Tour


camera
(33)

Details

294 Barberry Hill Road
Woodstock, VT 05091
$679,000

3 Beds


2 | 1 Baths


2,128 SqFt


Listing No. 5042200





Property Type: House


camera
(34)

Details

5851 South Road
Woodstock, VT 05071
$659,000

3 Beds


2 | 1 Baths


1,958 SqFt


Listing No. 5014012





Property Type: House


camera
Virtual Tour


camera
(39)

Details

187 Dana Road
Woodstock, VT 05091
$657,500

3 Beds


1 | 1 Baths


1,468 SqFt


Listing No. 5033694





Property Type: House


camera
Virtual Tour


camera
(19)

Details

1613 West Woodstock Road
Woodstock, VT 05091
$549,999

3 Beds


1 | 1 Baths


1,344 SqFt


Listing No. 5022904





Property Type: House


camera
(46)

Details

85 Townhouse Way #14
Woodstock, VT 05091
$495,000

2 Beds


1 | 2 Baths


2,091 SqFt


Listing No. 5039259





Property Type: Condo


camera
Virtual Tour


camera
(28)

Details

11A Prospect Street
Woodstock, VT 05091
$489,500

2 Beds


1 | 1 Baths


930 SqFt


Listing No. 5037971





Property Type: Condo


camera
Virtual Tour


camera
(26)

Details

442 E Woodstock Road #4A
Woodstock, VT 05091
$239,000

2 Beds


0 | 1 Baths


1,190 SqFt


Listing No. 5035698





Property Type: Condo


camera
(6)

Details

 234 Randall Road, Woodstock, VT 05091


camera
(14)

price

$845,000

beds

2
2 Beds

baths

1
1 Baths

lot size

600 SqFt
600 SqFt

listing no.

4913852
Listing No. 4913852

property type

House
Property Type: House

gallery photos


camera
(14)

 25 Linden Hill Street, Woodstock, VT 05091


camera
VIRTUAL TOUR


camera
(48)

price

$795,000

beds

3
3 Beds

baths

1 | 1
1 | 1 Baths

lot size

1,694 SqFt
1,694 SqFt

listing no.

5028831
Listing No. 5028831

property type

House
Property Type: House

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(48)

 339 Gully Road, Woodstock, VT 05091


camera
(40)

price

$775,000

beds

4
4 Beds

baths

1 | 2
1 | 2 Baths

lot size

2,688 SqFt
2,688 SqFt

listing no.

5037463
Listing No. 5037463

property type

House
Property Type: House

gallery photos


camera
(40)

 17 Golf Avenue, Woodstock, VT 05091


camera
VIRTUAL TOUR


camera
(39)

price

$775,000

beds

3
3 Beds

baths

1 | 2
1 | 2 Baths

lot size

1,850 SqFt
1,850 SqFt

listing no.

5043286
Listing No. 5043286

property type

House
Property Type: House

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(39)

 13 Slayton Terrace, Woodstock, VT 05091


camera
VIRTUAL TOUR


camera
(33)

price

$755,000

beds

3
3 Beds

baths

0 | 3
0 | 3 Baths

lot size

1,550 SqFt
1,550 SqFt

listing no.

5033279
Listing No. 5033279

property type

House
Property Type: House

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(33)

 294 Barberry Hill Road, Woodstock, VT 05091


camera
(34)

price

$679,000

beds

3
3 Beds

baths

2 | 1
2 | 1 Baths

lot size

2,128 SqFt
2,128 SqFt

listing no.

5042200
Listing No. 5042200

property type

House
Property Type: House

gallery photos


camera
(34)

 5851 South Road, Woodstock, VT 05071


camera
VIRTUAL TOUR


camera
(39)

price

$659,000

beds

3
3 Beds

baths

2 | 1
2 | 1 Baths

lot size

1,958 SqFt
1,958 SqFt

listing no.

5014012
Listing No. 5014012

property type

House
Property Type: House

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(39)

 187 Dana Road, Woodstock, VT 05091


camera
VIRTUAL TOUR


camera
(19)

price

$657,500

beds

3
3 Beds

baths

1 | 1
1 | 1 Baths

lot size

1,468 SqFt
1,468 SqFt

listing no.

5033694
Listing No. 5033694

property type

House
Property Type: House

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(19)

 1613 West Woodstock Road, Woodstock, VT 05091


camera
(46)

price

$549,999

beds

3
3 Beds

baths

1 | 1
1 | 1 Baths

lot size

1,344 SqFt
1,344 SqFt

listing no.

5022904
Listing No. 5022904

property type

House
Property Type: House

gallery photos


camera
(46)

 85 Townhouse Way #14, Woodstock, VT 05091


camera
VIRTUAL TOUR


camera
(28)

price

$495,000

beds

2
2 Beds

baths

1 | 2
1 | 2 Baths

lot size

2,091 SqFt
2,091 SqFt

listing no.

5039259
Listing No. 5039259

property type

Condo
Property Type: Condo

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(28)

 11A Prospect Street, Woodstock, VT 05091


camera
VIRTUAL TOUR


camera
(26)

price

$489,500

beds

2
2 Beds

baths

1 | 1
1 | 1 Baths

lot size

930 SqFt
930 SqFt

listing no.

5037971
Listing No. 5037971

property type

Condo
Property Type: Condo

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(26)

 442 E Woodstock Road #4A, Woodstock, VT 05091


camera
(6)

price

$239,000

beds

2
2 Beds

baths

0 | 1
0 | 1 Baths

lot size

1,190 SqFt
1,190 SqFt

listing no.

5035698
Listing No. 5035698

property type

Condo
Property Type: Condo

gallery photos


camera
(6)

Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real 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.
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 May 30, 2025, 9:08 PM ET

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