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Windsor, VT Homes for Sale

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  • /25

    $147,500

    • 3 Beds
    • 2 Baths
    • 1,742 Sq Ft

    7 Stardust Cir, Windsor, VT 05089

    Welcome to this spacious and well-maintained double-wide home located in a desirable age-restricted community in Weathersfield, Vermont. Offering 3 comfortable bedrooms and 2 bathrooms, this home provides an ideal blend of functionality and ease of living. The open-concept living and dining area is perfect for entertaining or relaxing, while the primary suite offers a private bath and generous

    Katie Ladue Gilbert KW Vermont Woodstock

    7 Stardust Cir, Windsor, VT 05089
  • /21

    $350,000

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

    205 Channing Dr, Windsor, VT 05089

    Welcome to this inviting 2-bedroom, 1.5-bath ranch-style home located just a short distance from Main Street in Windsor, VT. Set on a manageable and sunny .29-acre lot, this home offers convenient single-level living with a bright, open-concept kitchen and living area—perfect for relaxing or entertaining. A spacious back enclosed porch extends your living space, ideal for enjoying Vermont’s

    Katie Ladue Gilbert KW Vermont Woodstock

    205 Channing Dr, Windsor, VT 05089
  • /25

    $289,900

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

    1471 County Rd, Windsor, VT 05089

    Nestled in a peaceful rural setting, this roomy 4-bedroom, 3-bathroom home offers incredible potential for those looking to create their dream country home. While the property is in need of some work, it features a generous layout and sits on a little over an acre, which allows for plenty of space to enjoy the beautiful setting. The home features hardwood floors, vinyl windows, a pellet stove, as

    Jenn Boyer Coldwell Banker Homes Unlimited

    1471 County Rd, Windsor, VT 05089
  • /36

    $325,000

    • 4 Beds
    • 2 Baths
    • 2,452 Sq Ft

    358 Us Route 5 S, Windsor, VT 05089

    Charming Duplex in the Heart of Windsor – Ideal for Owner-Occupants or Investors! Discover a fantastic opportunity to own a versatile, income-producing duplex in the vibrant and historic town of Windsor. Perfectly suited for an owner-occupant looking to offset their mortgage with rental income—or a savvy investor seeking solid returns—this well-maintained property offers both comfort and cash

    Daniel Preston KW Vermont Woodstock

    358 Us Route 5 S, Windsor, VT 05089
  • /36

    $325,000

    • 2,452 Sq Ft

    358 Us Route 5 S, Windsor, VT 05089

    Charming Duplex in the Heart of Windsor – Ideal for Owner-Occupants or Investors! Discover a fantastic opportunity to own a versatile, income-producing duplex in the vibrant and historic town of Windsor. Perfectly suited for an owner-occupant looking to offset their mortgage with rental income—or a savvy investor seeking solid returns—this well-maintained property offers both comfort and cash

    Daniel Preston KW Vermont Woodstock

    358 Us Route 5 S, Windsor, VT 05089
  • /18

    $255,000

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

    66 Union St, Windsor, VT 05089

    Welcome to this beautifully maintained New Englander nestled in the historic town of Windsor — Vermont's first capital and a gem of the Upper Valley. This classic 3-bedroom, 2-bath home blends timeless charm with thoughtful updates, offering a perfect retreat in a vibrant, small-town setting.Located within walking distance to Windsor’s shops, restaurants, schools, and the picturesque Connecticut

    Katie Ladue Gilbert KW Vermont Woodstock

    66 Union St, Windsor, VT 05089
  • /54

    $950,000

    • 3 Beds
    • 2.5 Baths
    • 2,488 Sq Ft

    158 Rice Rd, Windsor, VT 05089

    This gorgeous post and beam home overlooks 10+ acres of rolling pasture framed by a mixture of hard and soft woods. Expansive 9' ceilings and light-filled rooms highlight the perfect confluence of natural wood and traditional building styles, all emphasized by first-class details including soapstone countertops, slate tile and stainless steel appliances - including a professional grade gas range.

    Terry Davis Williamson Group Sothebys Intl. Realty

    158 Rice Rd, Windsor, VT 05089
  • /27

    $57,000

    • Land
    • 0.67 Acre
    • $85,075 per Acre

    00 Snow Ln, Windsor, VT 05089

    Lovely residential neighborhood with easy access to I-91. This easy access building lot (Parcel #3) sits on a short private roadway with convenient hookups to town water and sewer. Power and internet is also at the street and easily available. Property is located on the school bus route and is a great location for families. Land is relatively flat and should be easy building. Good expansion

    John Bassette Bassette Real Estate Group

    00 Snow Ln, Windsor, VT 05089
  • /29

    $55,000

    • Land
    • 0.56 Acre
    • $98,214 per Acre

    00 Snow Ln, Windsor, VT 05089

    Lovely residential neighborhood with easy access to I-91. This perfect building lot (Parcel #2) sits on a short private roadway with convenient access to town water and sewer. Power and internet is at the street and easily available. Property is located on the school bus route and is a great location for families. The land is relatively flat and should be an easy building location. Good expansion

    John Bassette Bassette Real Estate Group

    00 Snow Ln, Windsor, VT 05089
  • /41

    $98,000

    • Land
    • 1.23 Acres
    • $79,675 per Acre

    00 Snow Ln, Windsor, VT 05089

    Lovely residential neighborhood with easy access to I91. These two separate and contiguous building lots sit on a small private road and have town water and sewer access on the edge of the property. Power is also on-site. This listing is for 1.23 acres that are divided into two separate buildable lots of Parcel #2 which is .56 acres (MLS #5036196), and Parcel #3 which is .67 acres (MLS #5036198).

    John Bassette Bassette Real Estate Group

    00 Snow Ln, Windsor, VT 05089
  • /16

    $410,000

    • 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
  • /3

    $590,000

    • 17 Beds
    • 2,768 Sq Ft

    1185 U S 5 S, Windsor, VT 05089

    Introducing a prime investment opportunity nestled on 1.44 acres of picturesque countryside just moments away from the convenience of town living. Whether you're a seasoned investor seeking a lucrative addition to your portfolio or a newcomer to the world of real estate investment, this 8-unit property presents an attractive proposition. With its idyllic location, modern updates, and reliable

    Katie Ladue Gilbert KW Vermont Woodstock

    1185 U S 5 S, Windsor, VT 05089
  • /4

    $195,000

    • 5 Beds
    • 3.5 Baths
    • 4,011 Sq Ft

    70-74 State St, Windsor, VT 05089

    The Stephen Jacob House is an extremely important historic residence in a town known for its historic architecture. Built in 1784 in the Georgian/Federal style, the residence was sited on the rise of State Street from the Village of Windsor. It's commanding presence was embellished with cornice dentil detailing and possibly a Palladian window. Having been used for many purposes over the years,

    Wade Treadway Wade I Treadway Real Estate

    70-74 State St, Windsor, VT 05089
  • /2

    $379,000

    • 7 Beds
    • 4 Baths
    • 3,894 Sq Ft

    102-104 State St, Windsor, VT 05089

    INVESTMENT PROPERTY. 4 UNITS, 1 1-bedroom unit & 3 2-bedroom units. Separate basement for each unit. Recent improvement includes, new roof, replaced plywood, foam board and membrane, at a cost of $70,600.00. Heat is separate pellet stoves for each unit, also an oil-fired steam system if needed for backup. Electric is separate, tenants pay electric. Landlord pays heat. Minimum of 48-hour required

    Don Chabot Town and Country Realty

    102-104 State St, Windsor, VT 05089

Why Live in Windsor

Located in the shadow of Mount Ascutney and on the banks of the Connecticut River, which separates Vermont from New Hampshire, Windsor is a township of about 3,500 residents as of the 2020 census. Known as the “birthplace of Vermont,” it's where the Constitution of the Vermont Republic was signed in 1777; Vermont would become a U.S. state in 1791. Windsor remained the state capital until 1805. Now, the area is known for for a mix of outdoor recreation opportunities, shops and restaurants in its small downtown area — and for a unique fall festiv ...

Frequently Asked Questions

What is the average home price in Windsor, VT?
Homes for sale in Windsor, VT have an average home price of $367,281.
How many homes have sold over the last 12 months in Windsor, VT?
33 homes have sold in Windsor, VT over the last 12 months.
What are the most popular zip codes in Windsor, VT?
The most popular zip codes in Windsor, VT include 05001, 05149, 03743, 03773 and 05751.
How much do you need to make to afford a house in Windsor?
The median home price in Windsor is $307,000. If you put a 20% down payment of $61,400 and had a 30-year fixed mortgage with an interest rate of 6.84%, your estimated principal and interest payment would be $1,610 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $69K a year to afford the median home price in Windsor.
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 Weathersfield School, Cornish Elementary School and Hartland Elementary School. Browse all the schools in Windsor, VT to learn more.

Home Trends in Windsor, VT

Housing Trends

Median Sale Price
$277,000
Median Single Family Sale Price
$279,250
Median Townhouse Sale Price
$1,085,750
Average Price Per Sq Ft
$188
Number of Homes for Sale
5
Last 12 months Home Sales
33
Months of Supply
1.80
Median List Price
$307,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
16%
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