Windsor County, VT Homes

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  /46

  $570,000

  Sold Nov 21, 2025

  167 Pettiner Hill Rd, Ludlow, VT 05149

  • 4 Beds
  • 3 Baths
  • 1,476 Sq Ft
  • Built 1970

  Last Sold Summary

  • 5% Below List Price
  • $386/SF
  • 21 Days On Market

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

  167 Pettiner Hill Rd, Ludlow, VT 05149
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  /27

  Est $971,322

  Not Listed For Sale

  7 Golf Ave, Woodstock, VT 05091

  • 5 Beds
  • 3 Baths
  • 3,579 Sq Ft
  • Built 1832

  7 Golf Ave, Woodstock, VT 05091

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty
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  /26

  $240,000

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft

  574 Willard Rd Unit 2C, Quechee, VT 05059

  Welcome to Quechee Hollow 2C, nestled in the picturesque town of Quechee, Vermont. This newly renovated two bedroom, one bath condominium offers a perfect blend of mountain comfort and convenience. The inviting and very cozy living room features a wood-burning fireplace, creating the perfect setting to relax, and warm up after a day on the slopes, or enjoying the outdoors. The upstairs includes

  Amy Tissera Four Seasons Sotheby's Int'l Realty

  574 Willard Rd Unit 2C, Quechee, VT 05059
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  /53

  $160,000

  Sold Aug 29, 2025

  399 Twitchell Settlement, Rochester, VT 05767

  • Land
  • 23.8 Acres
  • $6,723 per Acre

  Last Sold Summary

  • 11 Days On Market

  Current Estimated Value $439,113

  Last Listing Agent Nick Sicard EXP Realty

  399 Twitchell Settlement, Rochester, VT 05767
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  /36

  Est $600,065

  Not Listed For Sale

  24 High St, Woodstock, VT 05091

  • 5 Beds
  • 2 Baths
  • 2,996 Sq Ft
  • Built 1840

  24 High St, Woodstock, VT 05091

  Last Sold Summary

  • 325 Days On Market

  Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty
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  /19

  $155,000

  • 1 Bed
  • 1 Bath
  • 880 Sq Ft

  308 Route 100 S, Ludlow, VT 05149

  Here’s your chance to own your own home instead of renting. This would work well for one or two people. Currently there is a large room with beautiful natural light, picture window and a woodstove. This space can be used as living room/bedroom. The kitchen is another large room that could be divided for a separate bedroom and still have room for an eat-in kitchen. There is a full bath. There is a

  Betty McEnaney Diamond Realty

  308 Route 100 S, Ludlow, VT 05149
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  /53

  $874,000

  Sold Mar 16, 2026

  559 Crimson Hawk Rd, Plymouth, VT 05056

  • 4 Beds
  • 3.5 Baths
  • 2,667 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Below List Price
  • $328/SF
  • 39 Days On Market

  Current Estimated Value $888,014

  Last Listing Agent Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  559 Crimson Hawk Rd, Plymouth, VT 05056
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  /39

  Est $769,958

  Not Listed For Sale

  6 Highland Ave, Woodstock, VT 05091

  • 1 Bed
  • 1 Bath
  • 1,052 Sq Ft
  • Built 1930

  6 Highland Ave, Woodstock, VT 05091

  Last Sold Summary

  • 97 Days On Market

  Last Listing Agent John Wetmore Wetmore Real Estate
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  /55

  $1,625,000

  • 3 Beds
  • 3 Baths
  • 4,922 Sq Ft

  55 County Rd, Windsor, VT 05089

  Sited on a knoll with lovely views in every direction, this spacious, sun filled Contemporary home was built to last! Using the finest materials, commercial grade mechanics, and custom millwork, this home imbues quality throughout.An impressive fireplace with a wood burning insert anchors the Great Room with sweeping walls of windows integrating indoor and outdoor spaces, and French doors

  Danny Kogut Williamson Group Sothebys Intl. Realty

  55 County Rd, Windsor, VT 05089
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  /23

  $281,500

  Sold Aug 19, 2025

  860 Murphy's Rd Unit 3E, Quechee, VT 05059

  • 2 Beds
  • 1.5 Baths
  • 1,100 Sq Ft
  • Built 1982

  Last Sold Summary

  • 1% Above List Price
  • $256/SF
  • 2 Days On Market

  Last Listing Agent Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

  860 Murphy's Rd Unit 3E, Quechee, VT 05059
• 

  

  /37

  Est $903,725

  Not Listed For Sale

  13 High St, Woodstock, VT 05091

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1900

  13 High St, Woodstock, VT 05091

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Marni Rieger KW Vermont-Killington
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  /27

  $175,000

  $35K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 675 Sq Ft

  2940 Route 103 Unit 158, Cavendish, VT 05142

  A Rare Find...1 bedroom condominium at Castle Point, only 3 miles to Okemo Mountain Resort.This condo can be rented out or used whenever you like, it is a full ownership property and fully furnished. It is located in the back away from the hotel lobbies, but has access to the pool and gym facilities. On the first floor the condo has an open living room with a gas fireplace, dining room, and a

  Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

  2940 Route 103 Unit 158, Cavendish, VT 05142
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  /26

  $577,000

  Sold May 21, 2026

  19 Kettlebrook Rd Unit D5, Ludlow, VT 05149

  • 2 Beds
  • 2 Baths
  • 1,349 Sq Ft
  • Built 1984

  Last Sold Summary

  • 17% Below List Price
  • $428/SF
  • 281 Days On Market

  Current Estimated Value $586,139

  Last Listing Agent Andre Menard Mary W. Davis Realtor & Assoc., Inc.

  19 Kettlebrook Rd Unit D5, Ludlow, VT 05149
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  /38

  Est $602,962

  Not Listed For Sale

  39 South St, Woodstock, VT 05091

  • 2 Beds
  • 1.5 Baths
  • 1,020 Sq Ft
  • Built 1869

  39 South St, Woodstock, VT 05091

  Last Sold Summary

  • 83 Days On Market

  Last Listing Agent Holly Hall Hall Collins Real Estate Group
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  /40

  $800,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,649 Sq Ft

  58 Harrison Ln Unit K-102, Ludlow, VT 05149

  Winterplace at Okemo Mountain, where comfort, convenience, and year-round adventure come together for your slopeside retreat. Step inside to a welcoming mudroom, perfectly designed to keep all your ski gear organized after a day on the mountain. From there, the home opens into a bright and inviting living space, ideal for gathering with family and friends. The open-concept layout features a

  Joseph Karl William Raveis Real Estate Vermont Properties

  58 Harrison Ln Unit K-102, Ludlow, VT 05149
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  /57

  $845,000

  Sold Sep 26, 2025

  903 Old County Rd, Cavendish, VT 05142

  • 3 Beds
  • 3.5 Baths
  • 2,906 Sq Ft
  • Built 2002

  Last Sold Summary

  • $291/SF
  • 187 Days On Market

  Current Estimated Value $819,783

  Last Listing Agent Frank Provance Diamond Realty

  903 Old County Rd, Cavendish, VT 05142
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  /30

  Est $853,336

  Not Listed For Sale

  1 Border Ln, Woodstock, VT 05091

  • 3 Beds
  • 1.5 Baths
  • 1,368 Sq Ft
  • Built 1966

  1 Border Ln, Woodstock, VT 05091

  Last Sold Summary

  • 185 Days On Market

  Last Listing Agent Dan Noble Snyder Donegan Real Estate Group
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  /32

  $1,295,000

  $50K PRICE DROP

  • 7 Beds
  • 6 Baths
  • 5,774 Sq Ft

  310 Pierce Hill Rd, West Windsor, VT 05089

  With sweeping views of Mount Ascutney, this exceptional home offers the Vermont lifestyle so many buyers dream of. A place where family and friends gather, traditions begin, and every season brings new adventures. Thoughtfully expanded over time, it blends two living spaces into one inviting home, offering generous room to be together while providing comfort and privacy for everyone.The newer

  Gary Coger Four Seasons Sotheby's Int'l Realty

  310 Pierce Hill Rd, West Windsor, VT 05089
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  /35

  $300,000

  Sold Feb 02, 2026

  90 Webster Rd, Hartland, VT 05048

  • 2 Beds
  • 1 Bath
  • 1,058 Sq Ft
  • Built 1969

  Last Sold Summary

  • 12% Below List Price
  • $284/SF
  • 2 Days On Market

  Current Estimated Value $301,667

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

  90 Webster Rd, Hartland, VT 05048
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  /39

  Est $3,534,364

  Not Listed For Sale

  3 Church St, Woodstock, VT 05091

  • 10 Beds
  • 15 Baths
  • 10,206 Sq Ft
  • Built 1831

  3 Church St, Woodstock, VT 05091

  Last Sold Summary

  • 345 Days On Market

  Last Listing Agent Story Jenks LandVest, Inc/Woodstock

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