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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. 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
687 South Perry Road Barnard, VT 05091
$1,690,000
5 Beds 3 | 2 Baths 4,617 SqFt Listing No. 5044731 Property Type: House camera Virtual Tour camera (54)
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
15 Central Street Woodstock, VT 05091
$1,395,000
4 Beds 0 | 3 Baths 6,014 SqFt Listing No. 5031244 Property Type: House camera Virtual Tour camera (43)
Details
16 Church Street Woodstock, VT 05091
$1,295,000
4 Beds 2 | 1 Baths 3,089 SqFt Listing No. 5057977 Property Type: House camera (40)
Details
1782 Randall Road Woodstock, VT 05091
$1,185,000
4 Beds 3 Baths 2,785 SqFt Listing No. 5052613 Property Type: House camera Virtual Tour camera (37)
Details
616 Rose Hill Road Woodstock, VT 05091
$985,000
3 Beds 1 | 1 Baths 2,760 SqFt Listing No. 5049901 Property Type: House camera Virtual Tour camera (57)
Details
72 Oak Ridge Way Woodstock, VT 05091
$985,000
3 Beds 1 | 2 Baths 1,920 SqFt Listing No. 5049347 Property Type: House camera Virtual Tour camera (54)
Details
19 Church Street Woodstock, VT 05091
$950,000
5 Beds 3 | 2 Baths 3,486 SqFt Listing No. 5045415 Property Type: House camera Virtual Tour camera (27)
Details
509 Church Hill Woodstock, VT 05091
$945,000
3 Beds 1 | 2 Baths 2,150 SqFt Listing No. 5044870 Property Type: House camera Virtual Tour camera (55)
Details
100 Pomfret Road Woodstock, VT 05091
$945,000
4 Beds 2 | 1 Baths 2,044 SqFt Listing No. 5044013 Property Type: House camera Virtual Tour camera (50)
Details
403 Horseshoe Way Woodstock, VT 05071
$845,000
2 Beds 1 | 1 Baths 1,714 SqFt Listing No. 5045520 Property Type: House camera Virtual Tour camera (37)
Details
 687 South Perry Road, Barnard, VT 05091
camera VIRTUAL TOUR camera (54)
price

$1,690,000

beds

5 5 Beds

baths

3 | 2 3 | 2 Baths

lot size

4,617 SqFt 4,617 SqFt

listing no.

5044731 Listing No. 5044731

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (54)

 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)

 15 Central Street, Woodstock, VT 05091
camera VIRTUAL TOUR camera (43)
price

$1,395,000

beds

4 4 Beds

baths

0 | 3 0 | 3 Baths

lot size

6,014 SqFt 6,014 SqFt

listing no.

5031244 Listing No. 5031244

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (43)

 16 Church Street, Woodstock, VT 05091
camera (40)
price

$1,295,000

beds

4 4 Beds

baths

2 | 1 2 | 1 Baths

lot size

3,089 SqFt 3,089 SqFt

listing no.

5057977 Listing No. 5057977

property type

House Property Type: House

gallery photos

camera (40)

 1782 Randall Road, Woodstock, VT 05091
camera VIRTUAL TOUR camera (37)
price

$1,185,000

beds

4 4 Beds

baths

3 3 Baths

lot size

2,785 SqFt 2,785 SqFt

listing no.

5052613 Listing No. 5052613

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (37)

 616 Rose Hill Road, Woodstock, VT 05091
camera VIRTUAL TOUR camera (57)
price

$985,000

beds

3 3 Beds

baths

1 | 1 1 | 1 Baths

lot size

2,760 SqFt 2,760 SqFt

listing no.

5049901 Listing No. 5049901

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (57)

 72 Oak Ridge Way, Woodstock, VT 05091
camera VIRTUAL TOUR camera (54)
price

$985,000

beds

3 3 Beds

baths

1 | 2 1 | 2 Baths

lot size

1,920 SqFt 1,920 SqFt

listing no.

5049347 Listing No. 5049347

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (54)

 19 Church Street, Woodstock, VT 05091
camera VIRTUAL TOUR camera (27)
price

$950,000

beds

5 5 Beds

baths

3 | 2 3 | 2 Baths

lot size

3,486 SqFt 3,486 SqFt

listing no.

5045415 Listing No. 5045415

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (27)

 509 Church Hill, Woodstock, VT 05091
camera VIRTUAL TOUR camera (55)
price

$945,000

beds

3 3 Beds

baths

1 | 2 1 | 2 Baths

lot size

2,150 SqFt 2,150 SqFt

listing no.

5044870 Listing No. 5044870

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (55)

 100 Pomfret Road, Woodstock, VT 05091
camera VIRTUAL TOUR camera (50)
price

$945,000

beds

4 4 Beds

baths

2 | 1 2 | 1 Baths

lot size

2,044 SqFt 2,044 SqFt

listing no.

5044013 Listing No. 5044013

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (50)

 403 Horseshoe Way, Woodstock, VT 05071
camera VIRTUAL TOUR camera (37)
price

$845,000

beds

2 2 Beds

baths

1 | 1 1 | 1 Baths

lot size

1,714 SqFt 1,714 SqFt

listing no.

5045520 Listing No. 5045520

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (37)


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 September 5, 2025, 7:19 PM ET
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