Windsor County, VT Homes

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  $1,700,000 Sold Aug 15, 2025

  2090 Randall Rd, Woodstock, VT 05091

  • 3 Beds
  • 2.5 Baths
  • 2,423 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $702/SF
  • 177 Days On Market

  Current Estimated Value $1,657,301

  Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

  2090 Randall Rd, Woodstock, VT 05091
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  /39

  Est $244,213 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,354 Sq Ft

  21 Cherry St, Windsor, VT 05089

  21 Cherry St, Windsor, VT 05089
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  $895,000

  • 3 Beds
  • 2.5 Baths
  • 2,048 Sq Ft

  358 Cowdrey Path, South Woodstock, VT 05071

  This beautifully renovated, truly move-in-ready home has been thoughtfully updated throughout — including a brand-new kitchen, refreshed flooring, modernized bathrooms, fresh interior paint, a new garage door, an automatic full-house generator, and more. The property is offered FULLY TURNKEY, with nearly all furniture and furnishings conveying with the sale (artwork excluded). Privately sited in

  John Snyder Snyder Donegan Real Estate Group

  358 Cowdrey Path, South Woodstock, VT 05071
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  $55,000 Sold Aug 29, 2025

  420 Qtr III Jackson Gore Inn, Ludlow, VT 05149

  • 1 Bath
  • 496 Sq Ft
  • Built 2003

  Last Sold Summary

  • 15% Below List Price
  • $111/SF
  • 413 Days On Market

  Last Listing Agent Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

  420 Qtr III Jackson Gore Inn, Ludlow, VT 05149
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  /17

  Est $300,832 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,550 Sq Ft

  109 Morningside Dr, Windsor, VT 05089

  109 Morningside Dr, Windsor, VT 05089
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  $869,000 Under Contract

  • 5 Beds
  • 5 Baths
  • 3,886 Sq Ft

  3961 Hartland Hill Rd, Woodstock, VT 05091

  This lovely,expanded Cape sits just a half mile from Woodstock Village's East End.Surrounded by rolling green fields and wooded hillsides-this home offers a beautiful country setting less than a mile to village shopping, schools, dining and recreation. Updated with modern finishes to enhance accessibility and one level living-while maintaining the warm, country charm. First floor features a

  Tambrey Vutech KW Vermont Woodstock

  3961 Hartland Hill Rd, Woodstock, VT 05091
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  /40

  $2,750,000 Sold Feb 13, 2025

  318 Ebbin Lockwood Way, Woodstock, VT 05071

  • 3 Beds
  • 3.5 Baths
  • 6,047 Sq Ft
  • Built 1970

  Last Sold Summary

  • 20% Below List Price
  • $455/SF
  • 495 Days On Market

  Last Listing Agent Story Jenks LandVest, Inc/Woodstock

  318 Ebbin Lockwood Way, Woodstock, VT 05071
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  Est $278,506 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  6 Buena Vista Ct, Windsor, VT 05089

  6 Buena Vista Ct, Windsor, VT 05089
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  $599,000

  • 4 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  5100 Route 100, Plymouth, VT 05056

  (Das Grünebergehaus) The Green Mountain House. First time offered on market since 1978. This gorgeous farmhouse, circa 1831, has been lovingly maintained & updated over the current owner's term of ownership. Previously owned by the Coolidge Family. During the years of Calvin Coolidge's presidency this home was used as a guest house for political figures to come & stay while visiting President

  Marni Rieger KW Vermont-Killington

  5100 Route 100, Plymouth, VT 05056
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  /60

  $700,000 Sold Nov 14, 2025

  104 Spruce Ln, Ludlow, VT 05149

  • 2 Beds
  • 2 Baths
  • 1,644 Sq Ft
  • Built 1988

  Last Sold Summary

  • 7% Below List Price
  • $426/SF

  Last Listing Agent Michael Normyle Mary W. Davis Realtor & Assoc., Inc.

  104 Spruce Ln, Ludlow, VT 05149
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  /30

  Est $292,228 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,008 Sq Ft

  333 Brook Rd, Windsor, VT 05089

  333 Brook Rd, Windsor, VT 05089
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  $375,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  400 Melody Ln, Springfield, VT 05156

  This home truly checks all the boxes and what could be better than deciding on a new home just in time for the holidays? Thoughtfully set back from the road, the property offers expansive front and back yards, creating a sense of privacy and space. The two-car garage features automatic openers and an impressive workshop above with power. It is currently used for woodturning, but equally ideal for

  Franchesca Collins Hall Collins Real Estate Group

  400 Melody Ln, Springfield, VT 05156
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  /29

  $440,000 Sold Jun 30, 2025

  210 Hanover St, White River Junction, VT 05001

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft
  • Built 1965

  Last Sold Summary

  • 4% Above List Price
  • $305/SF
  • 76 Days On Market

  Current Estimated Value $434,281

  Last Listing Agent Jill Harlow Coldwell Banker LIFESTYLES - Hanover

  210 Hanover St, White River Junction, VT 05001
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  /40

  Est $355,238 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,161 Sq Ft

  49 Valley View Trace, Windsor, VT 05089

  49 Valley View Trace, Windsor, VT 05089
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  $59,000

  • Land
  • 3.15 Acres
  • $18,730 per Acre

  1003 Quarry Hill Rd, Rochester, VT 05767

  Undeveloped land parcel ready for you to utilize as a permanent home site or a camp spot. A blank canvas with access by truck or large SUV. Very near the Mountain Biking trail system and easy access onto paved town road. With tree clearing, this property can provide a great view of the Green Mt Range.

  Patricia Harvey Xsell Realty LLC

  1003 Quarry Hill Rd, Rochester, VT 05767
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  $695,000 Sold Dec 23, 2025

  36 Lower IV Unit 48A, Ludlow, VT 05149

  • 4 Beds
  • 2.5 Baths
  • 1,844 Sq Ft
  • Built 1987

  Last Sold Summary

  • 10% Below List Price
  • $377/SF
  • 165 Days On Market

  Last Listing Agent Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

  36 Lower IV Unit 48A, Ludlow, VT 05149
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  /20

  Est $191,986 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,439 Sq Ft

  146 Ascutney St, Windsor, VT 05089

  146 Ascutney St, Windsor, VT 05089
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  $599,000

  • 3 Beds
  • 3 Baths
  • 2,898 Sq Ft

  354 Grout Rd, Perkinsville, VT 05151

  Stunning contemporary home on 6+ acres. Great proximity to the Upper Valley/RT 91 and only 12 miles to skiing at Okemo! Sit in the panoramic south facing dining room and take in the Black River and local mountain views. Your own Vermont paradise! Quiet dead end road. This 1973 residence has a 2008 addition and has been transformed over the years. Many upgrades and updates, some just completed!

  Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  354 Grout Rd, Perkinsville, VT 05151
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  $263,000 Sold Dec 31, 2024

  690 Little Ascutney Rd, Perkinsville, VT 05151

  • 4 Beds
  • 4 Baths
  • 1,896 Sq Ft
  • Built 1964

  Last Sold Summary

  • 1% Below List Price
  • $139/SF
  • 15 Days On Market

  Current Estimated Value $326,566

  Last Listing Agent Linda Benoit Highland Realty

  690 Little Ascutney Rd, Perkinsville, VT 05151
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  Est $207,073 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 696 Sq Ft

  141 Ascutney St, Windsor, VT 05089

  141 Ascutney St, Windsor, VT 05089

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