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.
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Listing No.
5066210
Listing No.
5039451
Listing No.
5044620
Listing No.
5002873
Listing No.
5056336
Listing No.
5072035
Listing No.
5062350
Listing No.
5066205
Listing No.
5020106
Listing No.
5031244
Listing No.
5049535
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$18,000,000
7 7 Beds
5 | 5 5 | 5 Baths
12,520 SqFt 12,520 SqFt
5066210 Listing No. 5066210
House Property Type: House
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$8,000,000
3 3 Beds
3 | 1 3 | 1 Baths
5,384 SqFt 5,384 SqFt
5039451 Listing No. 5039451
House Property Type: House
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$6,750,000
4 4 Beds
4 | 1 4 | 1 Baths
5,087 SqFt 5,087 SqFt
5044620 Listing No. 5044620
House Property Type: House
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$3,500,000
6 6 Beds
2 | 4 2 | 4 Baths
5,433 SqFt 5,433 SqFt
5002873 Listing No. 5002873
House Property Type: House
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$3,500,000
6 6 Beds
2 | 6 2 | 6 Baths
5,142 SqFt 5,142 SqFt
5056336 Listing No. 5056336
House Property Type: House
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$3,300,000
3 3 Beds
1 | 4 1 | 4 Baths
3,682 SqFt 3,682 SqFt
5072035 Listing No. 5072035
House Property Type: House
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$2,599,000
9 9 Beds
11 11 Baths
5,993 SqFt 5,993 SqFt
5062350 Listing No. 5062350
House Property Type: House
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$2,395,000
6 6 Beds
1 | 4 1 | 4 Baths
3,645 SqFt 3,645 SqFt
5066205 Listing No. 5066205
House Property Type: House
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$1,750,000
4 4 Beds
2 | 2 2 | 2 Baths
5,000 SqFt 5,000 SqFt
5020106 Listing No. 5020106
House Property Type: House
(60)
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$1,600,000
4 4 Beds
0 | 3 0 | 3 Baths
6,014 SqFt 6,014 SqFt
5031244 Listing No. 5031244
House Property Type: House
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$1,495,000
4 4 Beds
1 | 2 1 | 2 Baths
2,532 SqFt 2,532 SqFt
5049535 Listing No. 5049535
House Property Type: House
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$1,425,000
5 5 Beds
2 | 2 2 | 2 Baths
3,440 SqFt 3,440 SqFt
5071895 Listing No. 5071895
House Property Type: House
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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.