Windsor, VT Homes

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  /57

  $535,000

  $100K PRICE DROP Under Contract

  • 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
• Explore Windsor

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  /15

  Starting at $1,950 Per Month

  • 3 Beds

  8 Union St, Windsor, VT 05089

  8 Union St.

  8 Union St, Windsor, VT 05089
• 

  

  

  /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 $314,706

  Last Listing Agent Evan Russell Real Broker LLC

  1 Dorrance St, 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

  • 20 Days On Market
• 

  

  

  /50

  $1,399,000

  $49K PRICE INCREASE

  • 4 Beds
  • 3.5 Baths
  • 4,000 Sq Ft

  145 the Plateau, Windsor, VT 05089

  "The Plateau", originally part of the Kennedy Biscuit Co. (Nabisco) family estate, is nestled on a plateau at the end of a private road which greets you with open fields, mature trees, beautiful gardens, and a protected front-and-center view of Mt. Ascutney to the West and the Connecticut River to the East. This private peaceful setting includes an inground pool for those hot summer days, and two

  Dan Noble Snyder Donegan Real Estate Group

  145 the Plateau, Windsor, VT 05089
• 

  

  /6

  Starting at $1,950 Per Month

  • 2 Beds

  18 State St, Windsor, VT 05089

  welcome to this generously sized two bedroom apartment, perfect for those seeking comfort and convenience. Located on State Street, this unit offers a great in-town location, just a short walk to restaurants, schools, and shopping.The main level features a large kitchen with brand new fixtures including a breakfast bar and complemented by a separate dining room, ideal for family meals or

  18 State St, Windsor, VT 05089
• 

  

  /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 $189,224

  Last Listing Agent Derek Greene Derek Greene

  5 Clough Ave, West Windsor, VT 05089
• 

  

  /14

  Est $177,333

  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

  • 5 Days On Market
• 

  

  /14

  $225,000

  • 3 Beds
  • 1 Bath
  • 1,095 Sq Ft

  24 Cherry St, Windsor, VT 05089

  Offers are in: Best and Final Offers due Monday 7/13/26 at 6pm Looking for an affordable way into homeownership? This ranch features 3 bedrooms and 1 full bath, this single-level home is perfect for first-time buyers or downsizers. Cozy up in the living room next to the fireplace or relax on the covered porch with your morning coffee. The easy, one-floor layout means low-maintenance living at a

  Allison Griep BHHS Verani Upper Valley

  24 Cherry St, Windsor, VT 05089
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  /12

  $1,500

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Condo for Rent

  14 James Foster Rd Unit A, West Windsor, VT 05089

  Newly renovated, 1-Bedroom, 1-Bath Apartment located on a secluded cul-de-sac near Hartland Four Corners, very convenient to Rte 91. Sunny entry room features large slider doors that lead out into garden area with views of Mt. Ascutney. Spacious Living Room, Galley Kitchen with Stainless-Steel refrigerator and electric stove, Large Bathroom with new vanity and extra-large Storage/Pantry. Brand

  14 James Foster Rd Unit A, West 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
• 

  

  /26

  Est $250,237

  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

  • 35 Days On Market
• 

  

  /36

  $510,000

  $25K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 4,933 Sq Ft

  2 Pine St, Windsor, VT 05089

  Come see and appreciate this recently rejuvenated and extraordinary home that includes 6 bedrooms and 4 bathrooms as well as a 2 car garage! Located just off the downtown village area, this unique property features historical charm and character with vintage woodwork, custom wood floors, high ceilings, spacious rooms and the nooks and crannies a classic home has to offer! Relax on the rear porch

  Susan Bellville Bellville Realty

  2 Pine St, Windsor, VT 05089
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  /8

  $1,325 Per Month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  9 State St Unit 3C, Windsor, VT 05089

  9 State St Unit 3C, 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 $250,420

  Last Listing Agent Kevin Holmes Blue Slate Realty

  338 Us Route 5 S, Windsor, VT 05089
• 

  

  /25

  Est $282,889

  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

  • 10 Days On Market
• 

  

  /16

  $96,232

  New Construction Under Contract

  • 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
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  /2

  $1,950 Per Month

  • 3 Beds
  • 1 Bath
  • Charming Home Near Downtown Windsor

  35 River St, Windsor, VT 05089

  Welcome to 35 River Street, a charming home located in the heart of Windsor. This spacious property offers a flexible layout with multiple living areas, abundant natural light, and classic character throughout.The home features hardwood flooring, generous room sizes. Enjoy the comfort of a covered porch and a location close to downtown shops, restaurants, and local

  35 River 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 $141,694

  Last Listing Agent Robert Balewicz Evergreen Realty of Vermont

  16 Day St, Windsor, VT 05089
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  /30

  Est $291,314

  Not Listed For Sale

  43 River St, Windsor, VT 05089

  • 4 Beds
  • 1.5 Baths
  • 2,116 Sq Ft
  • Built 1850

  43 River St, Windsor, VT 05089

  Last Sold Summary

  • 34 Days On Market
• 

  

  /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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  /18

  $2,900 Per Month

  • 3 Beds
  • 1 Bath
  • Beautiful Furnished Home with Cozy Rustic Finishes

  69 Belknap Ln, Windsor, VT 05089

  Welcome to this warm and inviting fully furnished 3-bedroom, 1-bath home that blends rustic charm with modern comfort. The spacious open-concept kitchen and dining area features beautiful wood accents, generous cabinet storage, and a functional layout ideal for both everyday living and entertaining. The living room offers a bright and comfortable space filled with natural light—perfect for

  69 Belknap Ln, Windsor, VT 05089
• 

  

  /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 $409,638

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

  96 Dairy Ln, Windsor, VT 05089
• 

  

  /36

  Est $330,785

  Not Listed For Sale

  4 Old Mill Pond Rd, Windsor, VT 05089

  • 3 Beds
  • 4 Baths
  • 2,052 Sq Ft
  • Built 1989

  4 Old Mill Pond Rd, Windsor, VT 05089

  Last Sold Summary

  • 294 Days On Market
• 

  

  /43

  $875,000

  Under Contract

  • 2 Beds
  • 2 Baths
  • 1,820 Sq Ft

  860 Yale Heights Rd, Windsor, VT 05089

  This impeccably orchestrated cottage style contemporary home was crafted by Ennis Builders in 2006 with an eye to meticulous detail. The sweeping cherry spiral staircase, beautiful stonework and superior fit and finish imbue a quality of workmanship that reflects throughout the home. The main level features an open-concept kitchen with maple butcher block counters, and quality stainless steel

  Danny Kogut Williamson Group Sothebys Intl. Realty

  860 Yale Heights Rd, Windsor, VT 05089
• 

  

  /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 $230,838

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

  66 Union St, Windsor, VT 05089
• 

  

  /32

  Est $349,797

  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

  • 4 Days On Market
• 

  

  /41

  $560,000

  Pending

  • 3 Beds
  • 3 Baths
  • 2,368 Sq Ft

  93 Belaski Rd, Windsor, VT 05089

  Exceptional Cape in Historic Windsor: Pool, Views & In-Law Suite Welcome home to this impeccably maintained Cape-style residence, where timeless charm meets modern elegance. Set against breathtaking protected views of Mt. Ascutney, this stunning 3-bedroom, 3-bath property is a rare find in one of Vermont's most storied communities. The heart of the home is a beautifully appointed, ultra-modern

  Katie Ladue Gilbert BHHS Verani Upper Valley

  93 Belaski Rd, Windsor, VT 05089
• 

  

  /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 $398,542

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

  58 Morningside Dr, Windsor, VT 05089
• 

  

  /4

  Est $217,692

  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

  • 29 Days On Market
• 

  

  /60

  $299,000

  • 2 Beds
  • 1 Bath
  • 1,152 Sq Ft

  466 Estey Ln, Windsor, VT 05089

  Embrace the ultimate Vermont lifestyle with this 1950s ranch, perfectly situated on 6.8 sprawling acres of versatile land at 466 Esty Lane in Windsor. Combining nostalgic mid-century charm with extraordinary future potential, this property is an absolute dream for investors, developers, or anyone looking to build their ideal country homestead. The existing home offers 1,152 square feet of

  Francis Duffy

  466 Estey Ln, Windsor, VT 05089
• 

  /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 $321,380

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

  8 Old Mill Pond Rd, Windsor, VT 05089
• 

  

  /23

  Est $209,962

  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

  • 82 Days On Market
• 

  

  /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
• 

  

  /16

  $347,000

  Sold Apr 30, 2026

  181 Banister Rd, Windsor, VT 05089

  • 3 Beds
  • 1 Bath
  • 1,620 Sq Ft
  • Built 1987

  Last Sold Summary

  • 20% Below List Price
  • $214/SF
  • 315 Days On Market

  Current Estimated Value $352,010

  Last Listing Agent Dan Noble Snyder Donegan Real Estate Group

  181 Banister Rd, Windsor, VT 05089
• 

  

  /40

  Est $515,922

  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

  • 2 Days On Market
• 

  

  /38

  $975,000

  Under Contract

  • 2 Beds
  • 2 Baths
  • 1,282 Sq Ft

  5 Maple Heights, Windsor, VT 05089

  5 MAPLE HEIGHTS- Simply stunning newer construction home with long range easterly views. This Scandinavian-inspired design built by Ambrose Custom Builders sits on a private hilltop in an ideal private setting with 8+ acres. The finish quality of the home is premium across the board. A large central great room has dramatic cathedral ceilings featuring Baltic Birch paneling, oversized windows to

  David Donegan Snyder Donegan Real Estate Group

  5 Maple Heights, Windsor, VT 05089
• 

  /2

  $340,000

  Sold Sep 05, 2025

  672 County Rd, Windsor, VT 05089

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1988

  Last Sold Summary

  • $227/SF
  • 0 Days On Market

  Current Estimated Value $356,586

  Last Listing Agent Katie Ladue Gilbert BHHS Verani Upper Valley

  672 County Rd, 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
• 

  

  /10

  $229,000

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  29 National St, Windsor, VT 05089

  Take a look at this rare chance to own a BRAND NEW home in the heart of Windsor. Built for efficiency, the house features a raised foundation to keep it out of the flood zone for extra peace of mind. The layout is practical and spacious, offering an open-concept first floor and large bedrooms upstairs.You are within walking distance to the Amtrak station and downtown, and our local Moover

  Chelsea Bevis KW Vermont Woodstock

  29 National St, Windsor, VT 05089

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