Windsor, VT Homes

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  $96,232 New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  517 Back Mountain Rd, Windsor, VT 05089

  Welcome to 517 Back Mountain Rd., 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

  517 Back Mountain Rd, Windsor, VT 05089
• Explore Windsor

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  /2

  $1,525 per month

  27 Maple Street

  2 Beds

  27 Maple St, Windsor, VT 05089

  27 Maple St, Windsor, VT 05089
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  /23

  $255,000 Sold Jul 01, 2025

  59 Weston Heights, Windsor, VT 05089

  • 4 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1942

  Last Sold Summary

  • $253/SF
  • 90 Days On Market

  Current Estimated Value $261,601

  Last Listing Agent Don Chabot Town and Country Realty

  59 Weston Heights, Windsor, VT 05089
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  /20

  Not Listed For Sale

  51 River St, Windsor, VT 05089

  • 4 Beds
  • 4 Baths
  • 2,509 Sq Ft
  • Built 1875

  51 River St, Windsor, VT 05089

  Last Sold Summary

  • $92/SF
  • 20 Days On Market

  Last Sold Price $230,000

  Last Listing Agent Ara Cardew BHG Masiello Keene
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  /16

  $390,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,620 Sq Ft

  181 Banister Rd, Windsor, VT 05089

  Over 10 acres of beautiful fields and pasture with long range views and stone walls lining the property. Mature trees dot the perimeter and a lovely stream runs along the roadside. There is a multilevel functioning barn with water and electricity and a small gated paddock off to the side. Located in the heart of Horse Country, this would be and ideal equestrian property or a great place to raise

  Dan Noble Snyder Donegan Real Estate Group

  181 Banister Rd, Windsor, VT 05089
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  /41

  $315,000 Sold Nov 21, 2025

  1 Dorrance St, Windsor, VT 05089

  • 2 Beds
  • 1.5 Baths
  • 1,649 Sq Ft
  • Built 1945

  Last Sold Summary

  • 4% Below List Price
  • $191/SF
  • 7 Days On Market

  Current Estimated Value $307,796

  Last Listing Agent Evan Russell Real Broker LLC

  1 Dorrance St, Windsor, VT 05089
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  /14

  Est $185,000 Not Listed For Sale

  17 Fairview Terrace, Windsor, VT 05089

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1950

  17 Fairview Terrace, Windsor, VT 05089

  Last Sold Summary

  • 47% Above List Price
  • $164/SF
  • 5 Days On Market

  Last Sold Price $126,000

  Last Listing Agent Berna Rexford Four Seasons Sotheby's Int'l Realty
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  /11

  $87,826 New Construction

  • 1 Bed
  • 1 Bath
  • 643 Sq Ft

  23 Cubb Ct, Windsor, VT 05089

  Welcome to 23 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 1 bedroom, 1 bathroom, and 643 sq. ft. (13'4"x48) 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

  23 Cubb Ct, Windsor, VT 05089
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  /24

  $60,000 Sold Dec 18, 2025

  5 Clough Ave, West Windsor, VT 05089

  • 3 Beds
  • 1 Bath
  • 1,392 Sq Ft
  • Built 1920

  Last Sold Summary

  • 25% Below List Price
  • $43/SF
  • 13 Days On Market

  Current Estimated Value $165,000

  Last Listing Agent Derek Greene Derek Greene

  5 Clough Ave, West Windsor, VT 05089
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  /38

  Est $349,890 Not Listed For Sale

  87 Kennedy Dr, Windsor, VT 05089

  • 3 Beds
  • 1.5 Baths
  • 955 Sq Ft
  • Built 1942

  87 Kennedy Dr, Windsor, VT 05089

  Last Sold Summary

  • 13% Above List Price
  • $325/SF
  • 2 Days On Market

  Last Sold Price $310,000

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley
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  /11

  $98,995 New Construction

  • 3 Beds
  • 2 Baths
  • 880 Sq Ft

  84 Cubb Ct, Windsor, VT 05089

  Welcome to 84 Cubb Court, , Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-66 model manufactured home offers 3 bedrooms, 2 bathrooms, and 880 sq. ft. (13'4"x66) 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

  84 Cubb Ct, Windsor, VT 05089
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  /30

  $335,000 Sold Jun 02, 2025

  77 Taylor Dr, Windsor, VT 05089

  • 8 Beds
  • 4 Baths
  • 5,088 Sq Ft
  • Built 1860

  Last Sold Summary

  • 7% Below List Price
  • $66/SF
  • 126 Days On Market

  Current Estimated Value $358,984

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

  77 Taylor Dr, Windsor, VT 05089
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  /17

  Est $258,074 Not Listed For Sale

  93 Weston Heights, Windsor, VT 05089

  • 3 Beds
  • 1 Bath
  • 1,064 Sq Ft
  • Built 1942

  93 Weston Heights, Windsor, VT 05089

  Last Sold Summary

  • 32% Above List Price
  • $184/SF
  • 11 Days On Market

  Last Sold Price $195,500

  Last Listing Agent Amy Messina Town and Country Realty
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  /57

  $565,000

  • 4 Beds
  • 2 Baths
  • 2,212 Sq Ft

  298 Jenneville Rd, Windsor, VT 05089

  PRICE REDUCED! Welcome to "Valley Brook Farm", an historic cape in the middle of horse country on 12.92 acres with barns, rolling & level pasture, a swimming pond, and brook. Located in the heart of the nationally renowned Green Mountain Horse Association trail network. Nestled on scenic & bucolic Jenneville Road, this c. 1820 cape offers the warmth of wide pine floors, post-and-beam character,

  John Bassette Bassette Real Estate Group

  298 Jenneville Rd, Windsor, VT 05089
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  /17

  $40,000 Sold Oct 06, 2025

  138 Ascutney St, Windsor, VT 05089

  • 2 Beds
  • 1 Bath
  • 434 Sq Ft
  • Built 1952

  Last Sold Summary

  • 4% Above List Price
  • $92/SF
  • 6 Days On Market

  Last Listing Agent DJ Chabot Town and Country Realty

  138 Ascutney St, Windsor, VT 05089
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  /26

  Est $239,336 Not Listed For Sale

  1092 Weeden Hill Rd, Windsor, VT 05089

  • 3 Beds
  • 1.5 Baths
  • 1,452 Sq Ft
  • Built 1863

  1092 Weeden Hill Rd, Windsor, VT 05089

  Last Sold Summary

  • 79% Above List Price
  • $92/SF
  • 35 Days On Market

  Last Sold Price $134,000

  Last Listing Agent Geoff Eckler Real Broker LLC
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  $450,000 Under Contract

  • 3,700 Sq Ft

  64 State St, Windsor, VT 05089

  Windsor’s income-producing potential meets turnkey ease in this updated five-unit multifamily, perfectly positioned in Vermont’s historic “Birthplace ofVermont” along the Connecticut River and at the base of Mount Ascutney. With four one-bedroom units and one two-bedroom, the property offers a flexible mix of traditional tenancy and high-demand furnished rentals in a market supported by

  Katie Ladue Gilbert BHHS Verani Upper Valley

  64 State St, Windsor, VT 05089
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  /11

  $240,000 Sold Jul 21, 2025

  338 Us Route 5 S, Windsor, VT 05089

  • 6 Beds
  • 2 Baths
  • 2,504 Sq Ft
  • Built 1840

  Last Sold Summary

  • $96/SF
  • 7 Days On Market

  Current Estimated Value $252,368

  Last Listing Agent Kevin Holmes Blue Slate Realty

  338 Us Route 5 S, Windsor, VT 05089
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  /25

  Est $247,884 Not Listed For Sale

  153 State St, Windsor, VT 05089

  • 4 Beds
  • 1.5 Baths
  • 1,600 Sq Ft
  • Built 1830

  153 State St, Windsor, VT 05089

  Last Sold Summary

  • 34% Above List Price
  • $116/SF
  • 10 Days On Market

  Last Sold Price $185,000

  Last Listing Agent Don Chabot Town and Country Realty
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  /20

  $259,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,176 Sq Ft

  3 Cherry St, Windsor, VT 05089

  Classic Vermont character meets everyday convenience in this sweet in-town New Englander. Set in the heart of Windsor, this three-bedroom, one-bath home puts you steps from local shops, dining, and all the charm of one of Vermont's most historic villages. Inside, a fireplace anchors the living space, offering the kind of warmth that makes a New England winter something to look forward to. The

  Katie Ladue Gilbert BHHS Verani Upper Valley

  3 Cherry St, Windsor, VT 05089
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  /26

  $94,900 Sold Dec 04, 2025

  16 Day St, Windsor, VT 05089

  • 2 Beds
  • 1 Bath
  • 660 Sq Ft
  • Built 1930

  Last Sold Summary

  • $144/SF
  • 4 Days On Market

  Current Estimated Value $157,244

  Last Listing Agent Robert Balewicz Evergreen Realty of Vermont

  16 Day St, Windsor, VT 05089
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  /32

  Est $331,163 Not Listed For Sale

  18 Pine St, Windsor, VT 05089

  • 3 Beds
  • 1.5 Baths
  • 1,721 Sq Ft
  • Built 1868

  18 Pine St, Windsor, VT 05089

  Last Sold Summary

  • 10% Below List Price
  • $215/SF
  • 4 Days On Market

  Last Sold Price $370,000

  Last Listing Agent Dana Waters Dark Horse Realty
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  /26

  $119,000

  • 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
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  /32

  $350,000 Sold May 30, 2025

  30 Union St, Windsor, VT 05089

  • 4 Beds
  • 4.5 Baths
  • 3,990 Sq Ft
  • Built 1900

  Last Sold Summary

  • 19% Below List Price
  • $88/SF
  • 232 Days On Market

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

  30 Union St, Windsor, VT 05089
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  /39

  Est $394,529 Not Listed For Sale

  1670 Marton Rd, Windsor, VT 05089

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • Built 1957

  1670 Marton Rd, Windsor, VT 05089

  Last Sold Summary

  • 13% Above List Price
  • $249/SF
  • 7 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley
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  /38

  $424,000

  • 4 Beds
  • 2.5 Baths
  • 2,888 Sq Ft

  273 Route 5 N, Windsor, VT 05089

  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 softwood floors, the peace of

  Allison Griep BHHS Verani Upper Valley

  273 Route 5 N, Windsor, VT 05089
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  /38

  $400,000 Sold Dec 19, 2025

  96 Dairy Ln, Windsor, VT 05089

  • 4 Beds
  • 2.5 Baths
  • 2,272 Sq Ft
  • Built 1992

  Last Sold Summary

  • 13% Below List Price
  • $176/SF
  • 85 Days On Market

  Current Estimated Value $400,274

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

  96 Dairy Ln, Windsor, VT 05089
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  /4

  Est $223,557 Not Listed For Sale

  17 Maple St, Windsor, VT 05089

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft
  • Built 1850

  17 Maple St, Windsor, VT 05089

  Last Sold Summary

  • 17% Above List Price
  • $186/SF
  • 29 Days On Market

  Last Sold Price $190,800

  Last Listing Agent Justin Ranney Coldwell Banker Homes Unlimited
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  /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
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  /18

  $219,000 Sold Sep 02, 2025

  66 Union St, Windsor, VT 05089

  • 3 Beds
  • 2 Baths
  • 1,743 Sq Ft
  • Built 1856

  Last Sold Summary

  • 14% Below List Price
  • $126/SF
  • 56 Days On Market

  Current Estimated Value $227,460

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

  66 Union St, Windsor, VT 05089
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  /23

  Est $197,062 Not Listed For Sale

  149 Main St, Windsor, VT 05089

  • 2 Beds
  • 2.5 Baths
  • 1,165 Sq Ft
  • Built 1795

  149 Main St, Windsor, VT 05089

  Last Sold Summary

  • 79% Above List Price
  • $94/SF
  • 82 Days On Market

  Last Sold Price $110,000

  Last Listing Agent Amy Messina Town and Country Realty
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  /39

  $615,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,468 Sq Ft

  223 Taylor Dr, Windsor, VT 05089

  This lovely home has plenty of sunny light filled space. Home features a large kitchen/eating area, with a formal-sized dining room, and spacious living room. First floor primary bedroom, and three more bedrooms upstairs. Main level laundry and lots of storage space in the basement.Two car garage with electric car charger.Recent improvements include paved driveway,mini splits and lifetime

  Ara Cardew BHG Masiello Keene

  223 Taylor Dr, Windsor, VT 05089
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  /28

  $395,900 Sold Nov 13, 2025

  58 Morningside Dr, Windsor, VT 05089

  • 3 Beds
  • 1.5 Baths
  • 1,680 Sq Ft
  • Built 1957

  Last Sold Summary

  • 1% Below List Price
  • $236/SF
  • 17 Days On Market

  Current Estimated Value $382,770

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

  58 Morningside Dr, Windsor, VT 05089
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  /40

  Est $461,779 Not Listed For Sale

  29 Main St, Windsor, VT 05089

  • 4 Beds
  • 3 Baths
  • 3,024 Sq Ft
  • Built 1840

  29 Main St, Windsor, VT 05089

  Last Sold Summary

  • 5% Below List Price
  • $160/SF
  • 2 Days On Market

  Last Sold Price $485,000

  Last Listing Agent Kate Jarvis Williamson Group Sothebys Intl. Realty
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  /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
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  /2

  $305,000 Sold Aug 26, 2025

  8 Old Mill Pond Rd, Windsor, VT 05089

  • 3 Beds
  • 5 Baths
  • 1,754 Sq Ft
  • Built 1989

  Last Sold Summary

  • $174/SF
  • 0 Days On Market

  Current Estimated Value $308,265

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

  8 Old Mill Pond Rd, Windsor, VT 05089
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  /36

  Est $871,018 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

  • 12% Above List Price
  • $124/SF
  • 731 Days On Market

  Last Sold Price $775,000

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley
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  $139,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,549 Sq Ft

  66 Country Skyline Blvd, Windsor, VT 05089

  Comfortable Living in a Peaceful Vermont 55+ Community Discover relaxed, low-maintenance living in this spacious 3-bedroom, 2-bathroom double-wide home nestled in a sought-after age-restricted community in Weathersfield, Vermont. Thoughtfully maintained and move-in ready, this home welcomes you with an open-concept living and dining area—perfect for hosting gatherings or enjoying quiet evenings

  Mike Hickey KW Vermont Woodstock

  66 Country Skyline Blvd, Windsor, VT 05089
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  /2

  $365,000 Sold May 15, 2025

  32 Ascutney St, Windsor, VT 05089

  • 4 Beds
  • 3 Baths
  • 1,998 Sq Ft
  • Built 1919

  Last Sold Summary

  • 3% Above List Price
  • $183/SF
  • 0 Days On Market

  Current Estimated Value $386,661

  Last Listing Agent Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

  32 Ascutney St, Windsor, VT 05089
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  /40

  Est $441,117 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

  • 4% Above List Price
  • $135/SF
  • 151 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Dan Noble Snyder Donegan Real Estate Group

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