Windsor, VT Homes

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  /16

  $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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  /21

  $1,800 per month

  77 Union St

  2 Beds

  77 Union St, Windsor, VT 05089

  77 Union 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 $249,554

  Last Listing Agent Don Chabot Town and Country Realty

  59 Weston Heights, Windsor, VT 05089
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  /20

  Not Listed For Sale

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

  51 River St, Windsor, VT 05089

  51 River St, Windsor, VT 05089
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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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  /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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  /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

  Last Listing Agent Evan Russell Real Broker LLC

  1 Dorrance St, Windsor, VT 05089
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  /14

  Est $122,000 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  17 Fairview Terrace, Windsor, VT 05089

  17 Fairview Terrace, Windsor, VT 05089
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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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  /10

  $2,400 per month

  • 2 Beds
  • 1 Bath
  • 1,275 Sq Ft
  • Condo for Rent

  2460 US Route 5 N, Windsor, VT 05089

  Duplex set back from road on Route 5, Windsor, VT. Town of Windsor, stores, restaurants, post office, rec center, bank within walking distance/short drive. Easy commute to Interstate 91.

  2460 US Route 5 N, 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

  Last Listing Agent Derek Greene Derek Greene

  5 Clough Ave, West Windsor, VT 05089
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  /38

  Est $303,479 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 955 Sq Ft

  87 Kennedy Dr, Windsor, VT 05089

  87 Kennedy Dr, Windsor, VT 05089
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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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  /18

  $2,150 per month

  • 1 Bed
  • 1 Bath
  • 864 Sq Ft
  • House for Rent

  3819 Vt-44, Windsor, VT 05089

  An unfurnished, one-bedroom home built in 2020. This charming "little green house" is located on a private lot with a two-car garage and a relaxing 8x20 farmhouse porch. It also features a small office space, radiant heating, central vacuum system, air exchanger, and a full heated basement. Heat and hot water are included. Conveniently located near hiking/biking trails, skiing, Brownsville

  3819 Vt-44, 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 $334,503

  Last Listing Agent Katie Ladue Gilbert KW Vermont Woodstock

  77 Taylor Dr, Windsor, VT 05089
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  /17

  Est $232,300 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,064 Sq Ft

  93 Weston Heights, Windsor, VT 05089

  93 Weston Heights, Windsor, VT 05089
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  /57

  $595,000

  • 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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  /10

  $2,400 per month

  • 2 Beds
  • 1 Bath
  • 1,275 Sq Ft
  • Condo for Rent

  2460 US Route 5 N, Windsor, VT 05089

  Duplex set back from road on Route 5, Windsor, VT. Town of Windsor, stores, restaurants, post office, rec center, bank within walking distance/short drive. Easy commute to Interstate 91.

  2460 US Route 5 N, 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 $247,077 Not Listed For Sale

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

  1092 Weeden Hill Rd, Windsor, VT 05089

  1092 Weeden Hill Rd, Windsor, VT 05089
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  /36

  $129,000

  • 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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  /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 $244,507

  Last Listing Agent Kevin Holmes Blue Slate Realty

  338 Us Route 5 S, Windsor, VT 05089
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  /29

  Est $292,709 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,142 Sq Ft

  74 Union St, Windsor, VT 05089

  74 Union St, 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
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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

  Last Listing Agent Robert Balewicz Evergreen Realty of Vermont

  16 Day St, Windsor, VT 05089
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  /18

  Est $232,664 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,514 Sq Ft

  159 State St, Windsor, VT 05089

  159 State St, Windsor, VT 05089
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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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  /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 KW Vermont Woodstock

  30 Union St, Windsor, VT 05089
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  /25

  Est $261,937 Not Listed For Sale

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

  153 State St, Windsor, VT 05089

  153 State St, 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
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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

  Last Listing Agent Katie Ladue Gilbert KW Vermont Woodstock

  96 Dairy Ln, Windsor, VT 05089
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  /32

  Est $366,131 Not Listed For Sale

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

  18 Pine St, Windsor, VT 05089

  18 Pine St, Windsor, VT 05089
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  /30

  $139,000

  • 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

  Katie Ladue Gilbert KW Vermont Woodstock

  66 Country Skyline Blvd, 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 $213,988

  Last Listing Agent Katie Ladue Gilbert KW Vermont Woodstock

  66 Union St, Windsor, VT 05089
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  /39

  Est $395,048 Not Listed For Sale

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

  1670 Marton Rd, Windsor, VT 05089

  1670 Marton Rd, 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

  Last Listing Agent Katie Ladue Gilbert KW Vermont Woodstock

  58 Morningside Dr, Windsor, VT 05089
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  /4

  Est $200,666 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft

  17 Maple St, Windsor, VT 05089

  17 Maple St, 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 $297,274

  Last Listing Agent Katie Ladue Gilbert KW Vermont Woodstock

  8 Old Mill Pond Rd, Windsor, VT 05089
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  /23

  Est $178,976 Not Listed For Sale

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

  149 Main St, Windsor, VT 05089

  149 Main St, 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 $361,223

  Last Listing Agent Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

  32 Ascutney St, Windsor, VT 05089

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