Woodstock, VT

Woodstock VT Real Estate

25Results

Woodstock - Picture perfect in every season, Woodstock is the quintessential Vermont town. Real estate architecture is Late Georgian, Federalist style and Greek revival on houses that line the main streets and The Green. This town is beautiful and has been a recreational VT real estate escape for well over a century. Woodstock boasts the only US National Park in Vermont, Marsh-Billings-Rockefeller National Historic Park. Billings Farm and Museum, a National Historic Landmark, includes a working dairy farm and 1890 house that hosts regular educational programs throughout the year. Learn more about Woodstock VT. 

Price High to Low
355 Greene Road Woodstock VT 05071

$14,900,000

Woodstock, VT

355 Greene Road

  • 7 Beds
  • 10 Baths
  • 183.7 Acres
  • 12,520 SqFt
  • 241 Days on Market
MLS#: 5066210

$6,750,000

Woodstock, VT

412 Skyland Lane

  • 4 Beds
  • 5 Baths
  • 63.88 Acres
  • 5,087 SqFt
  • 376 Days on Market
MLS#: 5044620

$6,673,000

Woodstock, VT

2358 Long Hill Road

  • 5 Beds
  • 4 Baths
  • 465 Acres
  • 4,165 SqFt
  • 31 Days on Market
MLS#: 5089158

$3,300,000

Woodstock, VT

249 Sawyer Road

  • 3 Beds
  • 5 Baths
  • 2.37 Acres
  • 3,682 SqFt
  • 182 Days on Market
MLS#: 5072035
New Listing

$3,100,000

Woodstock, VT

66 Hollow Farm Road

  • 5 Beds
  • 6 Baths
  • 105.1 Acres
  • 4,843 SqFt
  • 19 Days on Market
MLS#: 5091062

$2,950,000

Woodstock, VT

61 Academy Circle

  • 6 Beds
  • 6 Baths
  • 2 Acres
  • 5,433 SqFt
  • 717 Days on Market
MLS#: 5002873
New Listing

$2,950,000

Woodstock, VT

5798 South Road

  • 5 Beds
  • 7 Baths
  • 32 Acres
  • 4,510 SqFt
  • 2 Days on Market
MLS#: 5094600

$2,599,000

Woodstock, VT

41 Pleasant Street

  • 9 Beds
  • 11 Baths
  • 0.46 Acres
  • 5,993 SqFt
  • 267 Days on Market
MLS#: 5062350

$2,500,000

Woodstock, VT

114 Oak Ridge Way

  • 4 Beds
  • 4 Baths
  • 17.65 Acres
  • 5,127 SqFt
  • 40 Days on Market
MLS#: 5087228

$1,895,000

Woodstock, VT

2394 Fletcher Hill Road

  • 2 Beds
  • 3 Baths
  • 14.9 Acres
  • 2,944 SqFt
  • 55 Days on Market
MLS#: 5084536
Active Under Contract

$1,495,000

Woodstock, VT

3090 South Road

  • 3 Beds
  • 3 Baths
  • 5 Acres
  • 2,650 SqFt
  • 28 Days on Market
MLS#: 5089519
New Listing

$1,395,000

Woodstock, VT

1522 Barnard Road

  • 5 Beds
  • 4 Baths
  • 6.2 Acres
  • 3,648 SqFt
  • 28 Days on Market
MLS#: 5089552

Woodstock Real Estate

After you have checked out the listings below, contact me online or give me a call at 802-457-2244 and we can talk about a new home in Vermont!

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Copyright 2026 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, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated June 15, 2026 12:40 PM EDT