Main Content

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

249 Sawyer Road
Woodstock, VT 05091
$3,750,000

3 Beds


1 | 4 Baths


3,865 SqFt


Listing No. 5018393





Property Type: House


camera
Virtual Tour


camera
(54)

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

4945 South Road
Woodstock, VT 05071
$2,250,000

5 Beds


3 | 1 Baths


3,502 SqFt


Listing No. 5028924





Property Type: House


camera
Virtual Tour


camera
(40)

Details

2334 South Road
Woodstock, VT 05091
$2,200,000

3 Beds


2 | 1 Baths


5,422 SqFt


Listing No. 5043416





Property Type: House


camera
(59)

Details

20 The Green
Woodstock, VT 05091
$1,995,000

3 Beds


1 | 2 Baths


2,688 SqFt


Listing No. 5033342





Property Type: House


camera
Virtual Tour


camera
(57)

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
$1,850,000

4 Beds


2 | 2 Baths


5,000 SqFt


Listing No. 5020106





Property Type: House


camera
(60)

Details

15 Central Street
Woodstock, VT 05091
$1,550,000

4 Beds


0 | 3 Baths


6,014 SqFt


Listing No. 5031244





Property Type: House


camera
Virtual Tour


camera
(43)

Details

11 College Hill Road
Woodstock, VT 05091
$1,390,000

5 Beds


2 | 2 Baths


3,953 SqFt


Listing No. 5038647





Property Type: House


camera
(52)

Details

4 River Street
Woodstock, VT 05091
$995,000

2 Beds


0 | 3 Baths


2,176 SqFt


Listing No. 5042622





Property Type: House


camera
Virtual Tour


camera
(37)

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)

 249 Sawyer Road, Woodstock, VT 05091


camera
VIRTUAL TOUR


camera
(54)

price

$3,750,000

beds

3
3 Beds

baths

1 | 4
1 | 4 Baths

lot size

3,865 SqFt
3,865 SqFt

listing no.

5018393
Listing No. 5018393

property type

House
Property Type: House

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(54)

 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)

 4945 South Road, Woodstock, VT 05071


camera
VIRTUAL TOUR


camera
(40)

price

$2,250,000

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
(40)

 2334 South Road, Woodstock, VT 05091


camera
(59)

price

$2,200,000

beds

3
3 Beds

baths

2 | 1
2 | 1 Baths

lot size

5,422 SqFt
5,422 SqFt

listing no.

5043416
Listing No. 5043416

property type

House
Property Type: House

gallery photos


camera
(59)

 20 The Green, Woodstock, VT 05091


camera
VIRTUAL TOUR


camera
(57)

price

$1,995,000

beds

3
3 Beds

baths

1 | 2
1 | 2 Baths

lot size

2,688 SqFt
2,688 SqFt

listing no.

5033342
Listing No. 5033342

property type

House
Property Type: House

virtual tour


camera
VIRTUAL TOUR

gallery photos


camera
(57)

 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

$1,850,000

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)

 15 Central Street, Woodstock, VT 05091


camera
VIRTUAL TOUR


camera
(43)

price

$1,550,000

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)

 11 College Hill Road, Woodstock, VT 05091


camera
(52)

price

$1,390,000

beds

5
5 Beds

baths

2 | 2
2 | 2 Baths

lot size

3,953 SqFt
3,953 SqFt

listing no.

5038647
Listing No. 5038647

property type

House
Property Type: House

gallery photos


camera
(52)

 4 River Street, Woodstock, VT 05091


camera
VIRTUAL TOUR


camera
(37)

price

$995,000

beds

2
2 Beds

baths

0 | 3
0 | 3 Baths

lot size

2,176 SqFt
2,176 SqFt

listing no.

5042622
Listing No. 5042622

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 May 28, 2025, 9:02 PM ET

Real Estate IDX Powered by iHomefinder

Skip to content