Windsor
Vermont

Homes on 5+ Acres for Sale in Windsor County, VT

57Results

Windsor County homes on five acres or more include farmhouses, mountain-view homes and private retreats across east central Vermont. Browse Vermont homes with acreage, create a free account to save this search and receive alerts, or call CENTURY 21 Highview Realty at 603-542-7766 to speak with an agent.

Newest
New Listing
2141 Twenty Mile Stream Road Cavendish VT 05153

$1,300,000

Cavendish, VT

2141 Twenty Mile Stream Road

  • 5 Beds
  • 4 Baths
  • 23.13 Acres
  • 2,893 SqFt
  • 10 Days on Market
MLS#: 5112138
Active Under Contract

$319,000

Bethel, VT

1715 Dearing Road

  • 3 Beds
  • 2 Baths
  • 10 Acres
  • 1,876 SqFt
  • 12 Days on Market
MLS#: 5111814
New Listing

$449,000

Springfield, VT

50 John Nourse Road

  • 3 Beds
  • 2 Baths
  • 15.3 Acres
  • 2,100 SqFt
  • 18 Days on Market
MLS#: 5110953
Active Under Contract

$329,500

Cavendish, VT

2949 Route 131

  • 2 Beds
  • 1 Bath
  • 15 Acres
  • 1,052 SqFt
  • 21 Days on Market
MLS#: 5110657
New Listing

$950,000

Weathersfield, VT

888 Skyline Drive

  • 3 Beds
  • 2 Baths
  • 51.3 Acres
  • 2,020 SqFt
  • 24 Days on Market
MLS#: 5110174
Active Under Contract

$537,000

Weathersfield, VT

1778 Goulden Ridge Road

  • 3 Beds
  • 2 Baths
  • 10.1 Acres
  • 2,104 SqFt
  • 24 Days on Market
MLS#: 5110160
New Listing

$675,000

West Windsor, VT

793 Blood Hill Road

  • 2 Beds
  • 2 Baths
  • 43 Acres
  • 1,536 SqFt
  • 29 Days on Market
MLS#: 5109455

$595,000

Bethel, VT

1720 Macintosh Hill Road

  • 3 Beds
  • 2 Baths
  • 23.65 Acres
  • 1,752 SqFt
  • 32 Days on Market
MLS#: 5108684
Active Under Contract

$550,000

Cavendish, VT

312 Tierney Road

  • 3 Beds
  • 3 Baths
  • 5.42 Acres
  • 2,240 SqFt
  • 34 Days on Market
MLS#: 5108500

$2,499,000

Hartford, VT

3398 Jericho Road

  • 5 Beds
  • 6 Baths
  • 5.37 Acres
  • 4,462 SqFt
  • 35 Days on Market
MLS#: 5108462

$755,500

Springfield, VT

844 Greeley Road

  • 3 Beds
  • 3 Baths
  • 10.1 Acres
  • 4,280 SqFt
  • 35 Days on Market
MLS#: 5108458

$2,250,000

Cavendish, VT

226 Hoey Road

  • 4 Beds
  • 5 Baths
  • 77.68 Acres
  • 3,860 SqFt
  • 35 Days on Market
MLS#: 5108457

Acreage Homes in East Central Vermont

Windsor County is Vermont’s largest county by area, stretching from Hartford and Quechee through Woodstock and Windsor to Springfield and the Okemo region around Ludlow. Homes on larger parcels here include classic farmhouses with barns, contemporary homes with mountain views and log homes on wooded land. Interstates 89 and 91 cross the county’s eastern side. CENTURY 21 Highview Realty can help evaluate land, access and systems. Related searches include houses for sale in Windsor County and cape-style homes in Windsor County.

Frequently Asked Questions

Which towns are in Windsor County, Vermont?
Windsor County includes Hartford, Woodstock, Windsor, Springfield, Ludlow, Chester, Bethel, Royalton and other towns.
Is Windsor County the largest county in Vermont?
By land area, yes. Windsor County is the largest county 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 October 9, 2026 8:53 PM EDT