1,747

Windsor, VT Homes

Section Image
  • 00 Snow Ln, Windsor, VT 05089
    00 Snow Ln, Windsor, VT 05089
    00 Snow Ln, Windsor, VT 05089
    /41

    $90,000

    Sold Oct 30, 2025

    00 Snow Ln, Windsor, VT 05089

    • Land
    • 1.23 Acres
    • $73,171 per Acre

    Last Sold Summary

    • 8% Below List Price
    • 149 Days On Market

    Last Listing Agent John Bassette Bassette Real Estate Group

    00 Snow Ln, Windsor, VT 05089
    • 26 Main St, Windsor, VT 05089
      26 Main St, Windsor, VT 05089
      26 Main St, Windsor, VT 05089
      /36

      Est $862,742

      Not Listed For Sale

      26 Main St, Windsor, VT 05089

      • 9 Beds
      • 8.5 Baths
      • 6,232 Sq Ft
      • Built 1815
      26 Main St, Windsor, VT 05089

      Last Sold Summary

      • 731 Days On Market

  • 74 Union St, Windsor, VT 05089
    74 Union St, Windsor, VT 05089
    74 Union St, Windsor, VT 05089
    /25

    $329,000

    $10K PRICE DROP Under Contract
    • 4 Beds
    • 2 Baths
    • 2,142 Sq Ft

    74 Union St, Windsor, VT 05089

    Discover space, flexibility, and everyday convenience in this charming 4-bedroom, 2-bath home in the heart of Windsor. Thoughtfully designed with a spacious floor plan, the main living area features warm hardwood floors and abundant natural light, creating a bright and welcoming atmosphere throughout. The formal dining area flows seamlessly into the living room, perfect for both everyday living

    Chelsea Bevis KW Vermont Woodstock

    74 Union St, Windsor, VT 05089
  • 473 Taylor Dr, Windsor, VT 05089
    473 Taylor Dr, Windsor, VT 05089
    473 Taylor Dr, Windsor, VT 05089
    /36

    $426,000

    Sold Jan 23, 2026

    473 Taylor Dr, Windsor, VT 05089

    • 4 Beds
    • 2.5 Baths
    • 1,832 Sq Ft
    • Built 2003

    Last Sold Summary

    • $233/SF
    • 2 Days On Market

    Current Estimated Value $435,596

    Last Listing Agent Leila Tarantelli KW Coastal and Lakes & Mountains Realty/Hanover

    473 Taylor Dr, Windsor, VT 05089
    • 25 Main St, Windsor, VT 05089
      25 Main St, Windsor, VT 05089
      25 Main St, Windsor, VT 05089
      /40

      Est $462,325

      Not Listed For Sale

      25 Main St, Windsor, VT 05089

      • 4 Beds
      • 2 Baths
      • 3,146 Sq Ft
      • Built 1796
      25 Main St, Windsor, VT 05089

      Last Sold Summary

      • 151 Days On Market

  • 505 Back Mountain Rd Unit 14, Windsor, VT 05089
    505 Back Mountain Rd Unit 14, Windsor, VT 05089
    505 Back Mountain Rd Unit 14, Windsor, VT 05089
    /26

    $110,000

    $9K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 240 Sq Ft

    505 Back Mountain Rd Unit 14, Windsor, VT 05089

    This beautifully crafted 2024 "Incredible Tiny Home" built by Amish Artisans, is ready for its next owner. Thoughtfully designed for efficiency and comfort, the home features a convenient kitchen, a spacious bathroom, and a loft sleeping area with stairs for easy access. A mini-split system provides both heating and cooling, ensuring year-round comfort. Step outside to enjoy the well-built

    Jenna Luce RE/MAX Upper Valley

    505 Back Mountain Rd Unit 14, Windsor, VT 05089
  • 32 Clough Ave, Windsor, VT 05089
    32 Clough Ave, Windsor, VT 05089
    32 Clough Ave, Windsor, VT 05089
    /22

    $292,500

    Sold Aug 28, 2025

    32 Clough Ave, Windsor, VT 05089

    • 3 Beds
    • 1.5 Baths
    • 1,606 Sq Ft
    • Built 1920

    Last Sold Summary

    • $182/SF
    • 2 Days On Market

    Current Estimated Value $300,866

    Last Listing Agent Susan Bellville Bellville Realty

    32 Clough Ave, Windsor, VT 05089
    • 4 Kiniry St, Windsor, VT 05089
      4 Kiniry St, Windsor, VT 05089
      4 Kiniry St, Windsor, VT 05089
      /20

      Est $265,084

      Not Listed For Sale

      4 Kiniry St, Windsor, VT 05089

      • 4 Beds
      • 1.5 Baths
      • 1,400 Sq Ft
      • Built 1938
      4 Kiniry St, Windsor, VT 05089

      Last Sold Summary

      • 26 Days On Market

  • 273 Route 5 N, Windsor, VT 05089
    273 Route 5 N, Windsor, VT 05089
    273 Route 5 N, Windsor, VT 05089
    /38

    $413,900

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,888 Sq Ft

    273 Route 5 N, Windsor, VT 05089

    Motivated seller! Price drop! A rare piece of Vermont history, thoughtfully preserved for modern living. Dating to 1790, this distinguished brick and frame Colonial stands as a testament to early New England craftsmanship — and it's ready for its next chapter. Meticulously maintained over the centuries and updated where it counts, this two-story home offers the warmth of wide-plank hardwood and

    Allison Griep BHHS Verani Upper Valley

    273 Route 5 N, Windsor, VT 05089
  • 9 Main St, Windsor, VT 05089
    9 Main St, Windsor, VT 05089
    9 Main St, Windsor, VT 05089
    /29

    $200,001

    Sold Aug 28, 2025

    9 Main St, Windsor, VT 05089

    • 4 Beds
    • 1.5 Baths
    • 2,310 Sq Ft
    • Built 1890

    Last Sold Summary

    • $87/SF
    • 17 Days On Market

    Current Estimated Value $291,332

    Last Listing Agent Linda Benoit Highland Realty

    9 Main St, Windsor, VT 05089
    • 242 Huntington Dr, Windsor, VT 05089
      242 Huntington Dr, Windsor, VT 05089
      242 Huntington Dr, Windsor, VT 05089
      /19

      Est $320,034

      Not Listed For Sale

      242 Huntington Dr, Windsor, VT 05089

      • 3 Beds
      • 1 Bath
      • 1,110 Sq Ft
      • Built 1971
      242 Huntington Dr, Windsor, VT 05089

      Last Sold Summary

      • 5 Days On Market

  • 3440 Route 44, West Windsor, VT 05037
    3440 Route 44, West Windsor, VT 05037
    3440 Route 44, West Windsor, VT 05037
    /55

    $548,000

    Under Contract
    • 3 Beds
    • 3.5 Baths
    • 2,391 Sq Ft

    3440 Route 44, West Windsor, VT 05037

    Views of Mt. Ascutney from this well cared for contemporary home that has only been used as a second home for the original owners. The house takes advantage of the southwest exposure to be able to bring the outside in with the use of large palladium windows and multiple French doors. Some of the interior features include 3 woodburning fireplaces ,wide pine floors ,vaulted ceilings ,and skylights.

    Carol Wood Williamson Group Sothebys Intl. Realty

    3440 Route 44, West Windsor, VT 05037
  • 31 Maple St, Windsor, VT 05089
    31 Maple St, Windsor, VT 05089
    31 Maple St, Windsor, VT 05089
    /36

    $215,000

    Sold Oct 06, 2025

    31 Maple St, Windsor, VT 05089

    • 3 Beds
    • 1.5 Baths
    • 1,900 Sq Ft
    • Built 1900

    Last Sold Summary

    • 22% Below List Price
    • $113/SF
    • 56 Days On Market

    Current Estimated Value $234,654

    Last Listing Agent Tara Reeves Vermont Real Estate Company

    31 Maple St, Windsor, VT 05089
    • 39 Huntington Dr, Windsor, VT 05089
      39 Huntington Dr, Windsor, VT 05089
      39 Huntington Dr, Windsor, VT 05089
      /39

      Est $380,892

      Not Listed For Sale

      39 Huntington Dr, Windsor, VT 05089

      • 3 Beds
      • 1 Bath
      • 1,080 Sq Ft
      • Built 1967
      39 Huntington Dr, Windsor, VT 05089

      Last Sold Summary

      • 74 Days On Market

  • 108 Cubb Ct, Windsor, VT 05089
    108 Cubb Ct, Windsor, VT 05089
    108 Cubb Ct, Windsor, VT 05089
    /15

    $96,232

    New Construction
    • 2 Beds
    • 2 Baths
    • 777 Sq Ft

    108 Cubb Ct, Windsor, VT 05089

    Welcome to 132 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

    Kate Barry EXP Realty

    108 Cubb Ct, Windsor, VT 05089
  • 38 Jarvis St, Windsor, VT 05089
    38 Jarvis St, Windsor, VT 05089
    38 Jarvis St, Windsor, VT 05089
    /18

    $139,000

    Sold Jun 10, 2026

    38 Jarvis St, Windsor, VT 05089

    • 1 Bed
    • 1 Bath
    • 768 Sq Ft
    • Built 2018

    Last Sold Summary

    • $181/SF
    • 6 Days On Market

    Current Estimated Value $135,987

    Last Listing Agent Chelsea Bevis KW Vermont Woodstock

    38 Jarvis St, Windsor, VT 05089
    • 69 Morningside Dr, Windsor, VT 05089
      69 Morningside Dr, Windsor, VT 05089
      69 Morningside Dr, Windsor, VT 05089
      /39

      Est $324,032

      Not Listed For Sale

      69 Morningside Dr, Windsor, VT 05089

      • 3 Beds
      • 2 Baths
      • 1,242 Sq Ft
      • Built 1988
      69 Morningside Dr, Windsor, VT 05089

      Last Sold Summary

      • 30 Days On Market

  • 11 Cubb Ct, Windsor, VT 05089
    11 Cubb Ct, Windsor, VT 05089
    11 Cubb Ct, Windsor, VT 05089
    /16

    $96,232

    New Construction
    • 2 Beds
    • 2 Baths
    • 777 Sq Ft

    11 Cubb Ct, Windsor, VT 05089

    Welcome to 11 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

    Kate Barry EXP Realty

    11 Cubb Ct, Windsor, VT 05089
  • 205 Channing Dr, Windsor, VT 05089
    205 Channing Dr, Windsor, VT 05089
    205 Channing Dr, Windsor, VT 05089
    /21

    $310,000

    Sold Sep 05, 2025

    205 Channing Dr, Windsor, VT 05089

    • 2 Beds
    • 1.5 Baths
    • 1,391 Sq Ft
    • Built 1964

    Last Sold Summary

    • 11% Below List Price
    • $223/SF
    • 43 Days On Market

    Current Estimated Value $318,003

    Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

    205 Channing Dr, Windsor, VT 05089
    • 37 Morningside Dr, Windsor, VT 05089
      37 Morningside Dr, Windsor, VT 05089
      37 Morningside Dr, Windsor, VT 05089
      /34

      Est $400,220

      Not Listed For Sale

      37 Morningside Dr, Windsor, VT 05089

      • 3 Beds
      • 2 Baths
      • 1,638 Sq Ft
      • Built 1986
      37 Morningside Dr, Windsor, VT 05089

      Last Sold Summary

      • 33 Days On Market

  • 84 Cubb Ct, Windsor, VT 05089
    84 Cubb Ct, Windsor, VT 05089
    84 Cubb Ct, Windsor, VT 05089
    /11

    $98,995

    Sold May 14, 2026

    84 Cubb Ct, Windsor, VT 05089

    • 3 Beds
    • 2 Baths
    • 880 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Above List Price
    • $112/SF
    • 305 Days On Market

    Last Listing Agent Kate Barry EXP Realty

    84 Cubb Ct, Windsor, VT 05089
    • 2768 Hunt Rd, Windsor, VT 05089
      2768 Hunt Rd, Windsor, VT 05089
      2768 Hunt Rd, Windsor, VT 05089
      /32

      Est $1,105,265

      Not Listed For Sale

      2768 Hunt Rd, Windsor, VT 05089

      • 3 Beds
      • 2.5 Baths
      • 2,736 Sq Ft
      • Built 2006
      2768 Hunt Rd, Windsor, VT 05089

      Last Sold Summary

      • 21 Days On Market

  • 2085 Us Route 5 S, Windsor, VT 05089
    2085 Us Route 5 S, Windsor, VT 05089
    2085 Us Route 5 S, Windsor, VT 05089
    /27

    $327,000

    Sold Sep 26, 2025

    2085 Us Route 5 S, Windsor, VT 05089

    • 3 Beds
    • 1 Bath
    • 1,560 Sq Ft
    • Built 1933

    Last Sold Summary

    • 12% Above List Price
    • $210/SF
    • 4 Days On Market

    Current Estimated Value $331,392

    Last Listing Agent Josh Gray Real Broker LLC

    2085 Us Route 5 S, Windsor, VT 05089
    • 54 Hillside Dr, Windsor, VT 05089
      54 Hillside Dr, Windsor, VT 05089
      54 Hillside Dr, Windsor, VT 05089
      /21

      Est $281,690

      Not Listed For Sale

      54 Hillside Dr, Windsor, VT 05089

      • 3 Beds
      • 1 Bath
      • 1,000 Sq Ft
      • Built 1957
      54 Hillside Dr, Windsor, VT 05089

      Last Sold Summary

      • 10 Days On Market

  • 68 Jarvis St Unit 70, Windsor, VT 05089
    68 Jarvis St Unit 70, Windsor, VT 05089
    68 Jarvis St Unit 70, Windsor, VT 05089
    /41

    $165,000

    Sold Jan 23, 2026

    68 Jarvis St Unit 70, Windsor, VT 05089

    • 3 Beds
    • 1 Bath
    • 1,602 Sq Ft
    • Built 1917

    Last Sold Summary

    • $103/SF
    • 48 Days On Market

    Current Estimated Value $174,375

    Last Listing Agent Karolina Burtt EXP Realty

    68 Jarvis St Unit 70, Windsor, VT 05089
    • 2446 Us Route 5 N, Windsor, VT 05089
      2446 Us Route 5 N, Windsor, VT 05089
      2446 Us Route 5 N, Windsor, VT 05089
      /26

      Est $390,748

      Not Listed For Sale

      2446 Us Route 5 N, Windsor, VT 05089

      • 4 Beds
      • 2 Baths
      • 2,289 Sq Ft
      • Built 1890
      2446 Us Route 5 N, Windsor, VT 05089

      Last Sold Summary

      • 24 Days On Market

  • 14 Central St, Windsor, VT 05089
    14 Central St, Windsor, VT 05089
    14 Central St, Windsor, VT 05089
    /15

    $210,000

    Sold Aug 06, 2025

    14 Central St, Windsor, VT 05089

    • 1 Bed
    • 1.5 Baths
    • 1,056 Sq Ft
    • Built 1920

    Last Sold Summary

    • $199/SF
    • 7 Days On Market

    Current Estimated Value $221,238

    Last Listing Agent David White OwnerEntry.com

    14 Central St, Windsor, VT 05089
    • 3 Fitch Ct, Windsor, VT 05089
      3 Fitch Ct, Windsor, VT 05089
      3 Fitch Ct, Windsor, VT 05089
      /18

      Est $237,340

      Not Listed For Sale

      3 Fitch Ct, Windsor, VT 05089

      • 2 Beds
      • 2 Baths
      • 1,665 Sq Ft
      • Built 1940
      3 Fitch Ct, Windsor, VT 05089

      Last Sold Summary

      • 20 Days On Market

  • 3361 County Rd, Windsor, VT 05089
    3361 County Rd, Windsor, VT 05089
    3361 County Rd, Windsor, VT 05089
    /39

    $500,000

    Sold Dec 19, 2025

    3361 County Rd, Windsor, VT 05089

    • 3 Beds
    • 2.5 Baths
    • 1,452 Sq Ft
    • Built 1971

    Last Sold Summary

    • 21% Below List Price
    • $344/SF
    • 137 Days On Market

    Current Estimated Value $510,409

    Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

    3361 County Rd, Windsor, VT 05089
    • 159 Estey Ln, Windsor, VT 05089
      159 Estey Ln, Windsor, VT 05089
      159 Estey Ln, Windsor, VT 05089
      /27

      Est $283,000

      Not Listed For Sale

      159 Estey Ln, Windsor, VT 05089

      • 2 Beds
      • 2 Baths
      • 1,154 Sq Ft
      • Built 1957
      159 Estey Ln, Windsor, VT 05089

      Last Sold Summary

      • 6 Days On Market

  • 2545 County Rd, Windsor, VT 05089
    2545 County Rd, Windsor, VT 05089
    2545 County Rd, Windsor, VT 05089
    /20

    $230,000

    Sold Nov 24, 2025

    2545 County Rd, Windsor, VT 05089

    • 3 Beds
    • 2 Baths
    • 2,289 Sq Ft
    • Built 2001

    Last Sold Summary

    • 20% Below List Price
    • $100/SF
    • 0 Days On Market

    Current Estimated Value $273,415

    Last Listing Agent Chelsea Bevis KW Vermont Woodstock

    2545 County Rd, Windsor, VT 05089
    • 28 Enright Ave, Windsor, VT 05089
      28 Enright Ave, Windsor, VT 05089
      28 Enright Ave, Windsor, VT 05089
      /29

      Est $264,770

      Not Listed For Sale

      28 Enright Ave, Windsor, VT 05089

      • 3 Beds
      • 1 Bath
      • 1,080 Sq Ft
      • Built 1925
      28 Enright Ave, Windsor, VT 05089

      Last Sold Summary

      • 14 Days On Market

  • 255 Channing Dr, Windsor, VT 05089
    255 Channing Dr, Windsor, VT 05089
    255 Channing Dr, Windsor, VT 05089
    /20

    $350,000

    Sold Aug 29, 2025

    255 Channing Dr, Windsor, VT 05089

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft
    • Built 1996

    Last Sold Summary

    • $293/SF
    • 1 Day On Market

    Current Estimated Value $361,272

    Last Listing Agent Lisa Baldwin Coldwell Banker LIFESTYLES - Hanover

    255 Channing Dr, Windsor, VT 05089
    • 17 Dewey Ave, Windsor, VT 05089
      17 Dewey Ave, Windsor, VT 05089
      17 Dewey Ave, Windsor, VT 05089
      /56

      Est $201,293

      Not Listed For Sale

      17 Dewey Ave, Windsor, VT 05089

      • 3 Beds
      • 1 Bath
      • 1,523 Sq Ft
      • Built 1935
      17 Dewey Ave, Windsor, VT 05089

      Last Sold Summary

      • 139 Days On Market

  • 2505 County Rd, Windsor, VT 05089
    2505 County Rd, Windsor, VT 05089
    2505 County Rd, Windsor, VT 05089
    /30

    $299,000

    Sold Sep 30, 2025

    2505 County Rd, Windsor, VT 05089

    • 2 Beds
    • 1 Bath
    • 1,332 Sq Ft
    • Built 1974

    Last Sold Summary

    • $224/SF
    • 11 Days On Market

    Current Estimated Value $319,690

    Last Listing Agent Leila Tarantelli KW Coastal and Lakes & Mountains Realty/Hanover

    2505 County Rd, Windsor, VT 05089
    • 39 Dairy Ln, Windsor, VT 05089
      39 Dairy Ln, Windsor, VT 05089
      39 Dairy Ln, Windsor, VT 05089
      /40

      Est $347,597

      Not Listed For Sale

      39 Dairy Ln, Windsor, VT 05089

      • 2 Beds
      • 1.5 Baths
      • 936 Sq Ft
      • Built 1992
      39 Dairy Ln, Windsor, VT 05089

      Last Sold Summary

      • 8 Days On Market

  • 64 State St, Windsor, VT 05089
    64 State St, Windsor, VT 05089
    64 State St, Windsor, VT 05089
    /41

    $425,000

    Sold May 05, 2026

    64 State St, Windsor, VT 05089

    • 3,700 Sq Ft
    • Built 1880

    Last Sold Summary

    • 6% Below List Price
    • $115/SF
    • 1 Day On Market

    Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

    64 State St, Windsor, VT 05089
    • 40 Village Green, Windsor, VT 05089
      40 Village Green, Windsor, VT 05089
      40 Village Green, Windsor, VT 05089
      /37

      Est $369,182

      Not Listed For Sale

      40 Village Green, Windsor, VT 05089

      • 6 Beds
      • 5 Baths
      • 3,176 Sq Ft
      • Built 1800
      40 Village Green, Windsor, VT 05089

      Last Sold Summary

      • 8 Days On Market

  • 1471 County Rd, Windsor, VT 05089
    1471 County Rd, Windsor, VT 05089
    1471 County Rd, Windsor, VT 05089
    /25

    $290,000

    Sold Aug 25, 2025

    1471 County Rd, Windsor, VT 05089

    • 4 Beds
    • 2.5 Baths
    • 2,196 Sq Ft
    • Built 1975

    Last Sold Summary

    • $132/SF
    • 14 Days On Market

    Current Estimated Value $322,065

    Last Listing Agent Jenn Boyer Coldwell Banker Homes Unlimited

    1471 County Rd, Windsor, VT 05089
    • 3223 County Rd, Windsor, VT 05089
      3223 County Rd, Windsor, VT 05089
      3223 County Rd, Windsor, VT 05089
      /39

      Est $709,977

      Not Listed For Sale

      3223 County Rd, Windsor, VT 05089

      • 4 Beds
      • 2 Baths
      • 2,238 Sq Ft
      • Built 1801
      3223 County Rd, Windsor, VT 05089

      Last Sold Summary

      • 38 Days On Market

Showing Results 41 - 80, Page 2 of 18

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