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Windsor, VT Homes for Sale

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  • /60

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    1268 County Rd, Windsor, VT 05089

    Pull off County Road and the gravel goes quiet under the tires as 16.35 acres in Windsor, Vermont open in grass, timber, and sky. Hubbard Brook moves through the land with water over stone, cool in the shade and bright where the light finds it, and a snowmobile trail crosses the acreage when winter takes the fields. I-91 sits close enough that the Upper Valley is an easy reach. That is 1268

    Agent Photo

    Vin Morris

    BHHS Verani Upper Valley

    1268 County Rd, Windsor, VT 05089
  • /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
  • /36

    $490,000

    $45K 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
  • /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
  • /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
  • /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
  • /10

    $189,000

    $40K PRICE DROP
    • 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
  • /26

    $99,000

    $20K 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
  • /4

    $125,000

    $10K PRICE DROP
    • Land
    • 5.05 Acres
    • $24,752 per Acre

    000 Marton Rd, Windsor, VT 05089

    Special private land offering, rare 5 acre parcel, abutting a bird sanctuary: 850 acres of protected Windsor Grasslands State of Vermont Wildlife Management area. Additional acreage is available. Perk tests, test pits done. Off a public, quiet dirt road. Lovely maples, and a brook, add to its beauty. An outstanding opportunity for those seeking rural privacy, yet minutes from downtown Windsor,

    John MacGovern Dark Horse Realty

    000 Marton Rd, 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
  • /43

    $1,249,000

    $246K PRICE DROP
    • Land
    • 48.11 Acres
    • $25,961 per Acre

    1 US Route 5 Rd, Hartland, VT 05048

    48.11 Acres of Spectacular Vermont Land with Panoramic Views!Discover a rare opportunity to own 48.11 acres of exceptional Vermont countryside in the heart of the Connecticut River Valley, often referred to as Vermont's "Shenandoah Valley" for its scenic beauty. This remarkable property offers breathtaking 180-degree views to the east and south, creating an unforgettable setting for a dream

    Charles Bacon Quechee Lakes Real Estate Center

    1 US Route 5 Rd, Hartland, VT 05048

Why Live in Windsor

Windsor, Vermont, nestled by Mount Ascutney and the Connecticut River, is a historic township with a population of around 3,500. Known as the “birthplace of Vermont,” it boasts a rich history, including the signing of the Vermont Republic Constitution in 1777. The area offers a mix of outdoor recreation, shops, and restaurants in its small downtown. Outdoor enthusiasts can explore Paradise Park with its trails around Lake Runnemede, or enjoy activities at Mount Ascutney, which features a J-Bar lift, rope tow, and tubing run. Great River Outfitters provides canoe and kayak tours on the Connecticut River, and the Path of Life Sculpture Garden adds a unique touch. Windsor’s downtown area includes Artisans Park, home to Harpoon Brewery, Silo Distillery, and other local businesses. Windsor Station Restaurant and Barroom offers dining in a historic train depot setting. The Autumn Moon Festival and a year-round farmers market add to the community's vibrant atmosphere. Housing options range from historic homes dating back to the late 1700s to mid-20th-century Cape Cods and ranch-style homes, with expansive country lots available outside the town center. Windsor is safer than the national average, making it a practical choice for families and individuals alike. The town is well-connected with Interstate 91, U.S. Route 5, and daily Amtrak service. Nearby Claremont, New Hampshire, is about 10 miles away, and Burlington International Airport is approximately 100 miles from Windsor.

Windsor, VT Home Prices

Windsor, VT
Median Home Price
$312,000
Median Sale Price
$313,500
+13% YoY
Avg. Price per Square Foot
$242
Median Single Family Price
$288,500
Median Townhouse Price
$487,500
Total Active Listings
11 listings
Market Conditions
3 Months of Supply
Seller's Market

Frequently Asked Questions

What is the average home price in Windsor, VT?
Homes for sale in Windsor, VT have an average home price of $443,908.
How many homes have sold over the last 12 months in Windsor, VT?
28 homes have sold in Windsor, VT over the last 12 months.
What is the average household income in Windsor, VT?
The average household income in Windsor, VT is $68K.
What are the most popular zip codes in Windsor, VT?
The most popular zip codes in Windsor, VT include 05089, 05048, 03745, 03781 and 05037.
How much do you need to make to afford a house in Windsor?
The median home price in Windsor is $312,000. If you put a 20% down payment of $62,400 and had a 30-year fixed mortgage with an interest rate of 6.95%, your estimated principal and interest payment would be $1,650 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $71K a year to afford the median home price in Windsor. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Windsor is $68K.
How are the schools in Windsor, VT?
Windsor, VT has highly rated public and private schools. Some of the best schools in Windsor based on Niche Grades are Hartland Elementary School, Weathersfield School and Cornish Elementary School. Browse all the schools in Windsor, VT to learn more.
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