Main Content

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
851 Riverside Park Road Woodstock, VT 05091
$2,450,000
4 Beds 1 | 3 Baths 5,573 SqFt Listing No. 5025630 Property Type: House camera Virtual Tour camera (60)
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
61 Academy Circle Woodstock, VT 05071
$3,500,000
6 Beds 2 | 4 Baths 5,433 SqFt Listing No. 5002873 Property Type: House camera Virtual Tour camera (40)
Details
18 The Green Woodstock, VT 05091
$3,500,000
6 Beds 2 | 6 Baths 5,142 SqFt Listing No. 5056336 Property Type: House camera Virtual Tour camera (42)
Details
2 Pleasant Street Woodstock, VT 05091
$2,600,000
4 Beds 3 | 1 Baths 3,998 SqFt Listing No. 5057220 Property Type: House camera Virtual Tour camera (43)
Details
4945 South Road Woodstock, VT 05071
$1,950,000
5 Beds 3 | 1 Baths 3,502 SqFt Listing No. 5028924 Property Type: House camera Virtual Tour camera (43)
Details
10 College Hill Road Woodstock, VT 05091
$1,895,000
5 Beds 3 | 2 Baths 4,214 SqFt Listing No. 5031704 Property Type: House camera Virtual Tour camera (35)
Details
2706 East Woodstock Road Woodstock, VT 05091
$1,800,000
4 Beds 2 | 2 Baths 5,000 SqFt Listing No. 5020106 Property Type: House camera (60)
Details
39 Elm Street #B Woodstock, VT 05091
$1,749,000
3 Beds 1 | 3 Baths 3,294 SqFt Listing No. 5047468 Property Type: Condo camera Virtual Tour camera (48)
Details
7 North Street Woodstock, VT 05091
$1,745,000
2 Beds 1 | 2 Baths 2,106 SqFt Listing No. 5043657 Property Type: House camera Virtual Tour camera (59)
Details
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
 851 Riverside Park Road, Woodstock, VT 05091
camera VIRTUAL TOUR camera (60)
price

$2,450,000

beds

4 4 Beds

baths

1 | 3 1 | 3 Baths

lot size

5,573 SqFt 5,573 SqFt

listing no.

5025630 Listing No. 5025630

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (60)

 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)

 61 Academy Circle, Woodstock, VT 05071
camera VIRTUAL TOUR camera (40)
price

$3,500,000

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)

 18 The Green, Woodstock, VT 05091
camera VIRTUAL TOUR camera (42)
price

$3,500,000

beds

6 6 Beds

baths

2 | 6 2 | 6 Baths

lot size

5,142 SqFt 5,142 SqFt

listing no.

5056336 Listing No. 5056336

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (42)

 2 Pleasant Street, Woodstock, VT 05091
camera VIRTUAL TOUR camera (43)
price

$2,600,000

beds

4 4 Beds

baths

3 | 1 3 | 1 Baths

lot size

3,998 SqFt 3,998 SqFt

listing no.

5057220 Listing No. 5057220

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (43)

 4945 South Road, Woodstock, VT 05071
camera VIRTUAL TOUR camera (43)
price

$1,950,000

beds

5 5 Beds

baths

3 | 1 3 | 1 Baths

lot size

3,502 SqFt 3,502 SqFt

listing no.

5028924 Listing No. 5028924

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (43)

 10 College Hill Road, Woodstock, VT 05091
camera VIRTUAL TOUR camera (35)
price

$1,895,000

beds

5 5 Beds

baths

3 | 2 3 | 2 Baths

lot size

4,214 SqFt 4,214 SqFt

listing no.

5031704 Listing No. 5031704

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (35)

 2706 East Woodstock Road, Woodstock, VT 05091
camera (60)
price

$1,800,000

beds

4 4 Beds

baths

2 | 2 2 | 2 Baths

lot size

5,000 SqFt 5,000 SqFt

listing no.

5020106 Listing No. 5020106

property type

House Property Type: House

gallery photos

camera (60)

 39 Elm Street #B, Woodstock, VT 05091
camera VIRTUAL TOUR camera (48)
price

$1,749,000

beds

3 3 Beds

baths

1 | 3 1 | 3 Baths

lot size

3,294 SqFt 3,294 SqFt

listing no.

5047468 Listing No. 5047468

property type

Condo Property Type: Condo

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (48)

 7 North Street, Woodstock, VT 05091
camera VIRTUAL TOUR camera (59)
price

$1,745,000

beds

2 2 Beds

baths

1 | 2 1 | 2 Baths

lot size

2,106 SqFt 2,106 SqFt

listing no.

5043657 Listing No. 5043657

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (59)

 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)


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 3, 2025, 9:25 PM ET
Real Estate IDX Powered by iHomefinder
Skip to content