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Windsor Homes for Sale

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  • /15

    $209,000 Open Sun 11AM - 1PM

    • 1 Bed
    • 1.5 Baths
    • 1,056 Sq Ft

    14 Central St, Windsor, VT 05089

    Discover this incredibly efficient, modern home in downtown Windsor, fully updated in 2018. This turn-key property offers comfort, convenience, and contemporary living.Step inside to find all main living areas thoughtfully located on the second floor. The primary bedroom boasts an oversized, ensuite bathroom with a spacious walk-in shower, providing a private oasis. The kitchen is a

    David White OwnerEntry.com

    14 Central St, Windsor, VT 05089
  • /30

    $299,000

    • 2 Beds
    • 1 Bath
    • 1,332 Sq Ft

    2505 County Rd, Windsor, VT 05089

    Here's a hidden gem for you in the heart of Vermont's magical, tranquil and picturesque countryside. Situated on 22 acres of forest and field sits a modest ranch home that is simplistic in style but overflowing with warmth and contentment. Loved for 40k+ years, it will be hard to turn over to its next denizen. The home is a time capsule of 70's charm and with some updating, can be enhanced

    Leila Tarantelli KW Coastal and Lakes & Mountains Realty/Hanover

    2505 County Rd, Windsor, VT 05089
  • /55

    $669,000

    • 3 Beds
    • 3.5 Baths
    • 2,391 Sq Ft

    3440 Route 44, West Windsor, VT 05037

    This well cared for contemporary home has only been used as a second home for the original owners. The house takes advantage of the southwest exposure to be able to bring the outside in with the use of large palladium windows and multiple French doors. Some of the interior features include 3 woodburning fireplaces ,wide pine floors ,vaulted ceilings ,and skylights. The floor plan has an easy

    Carol Wood Williamson Group Sothebys Intl. Realty

    3440 Route 44, West Windsor, VT 05037
  • /39

    $635,000

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

    3361 County Rd, Windsor, VT 05089

    Enjoy privacy and lovely views from this well executed contemporary home overlooking copious gardens and mature plantings to a spectacular pond with an arched footbridge (spotlights highlight the bridge after dark) to access your own little island. Beautiful updates throughout the home include new cedar shingles on the entire house, garage and workshop shed. The kitchen features custom oak

    Danny Kogut Williamson Group Sothebys Intl. Realty

    3361 County Rd, 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
  • /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

    $239,000

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

    66 Union St, Windsor, VT 05089

    PRICE JUST IMPROVED!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,

    Katie Ladue Gilbert KW Vermont Woodstock

    66 Union St, 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
  • /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

    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

Frequently Asked Questions Why Live in Windsor

Is Windsor a good place to live?
Windsor is a good place to live. Windsor is considered very car-dependent and somewhat bikeable. Windsor is a neighborhood with a crime score of 2, making it safer than the average neighborhood in the U.S. Windsor has 7 parks for recreational activities. It has a median age of 45. The average household income is $68,403 which is below the national average. College graduates make up 27.1% of residents. A majority of residents in Windsor are home owners, with 39.7% of residents renting and 60.3% of residents owning their home. A local real estate agent serving Windsor can help you decide if this neighborhood is the right one for you. Learn more on our Windsor neighborhood guide.
Is Windsor, VT a safe neighborhood?
Windsor, VT is safer than the average neighborhood in the United States. It received a crime score of 2 out of 10.
How much do you need to make to afford a house in Windsor?
The median home price in Windsor is $299,000. If you put a 20% down payment of $59,800 and had a 30-year fixed mortgage with an interest rate of 6.77%, your estimated principal and interest payment would be $1,550 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $66K a year to afford the median home price in Windsor. The average household income in Windsor is $68K.
What are the best public schools in Windsor?
The best public schools that serve Windsor are:
  • Windsor School has a C+ Niche grade, a student teacher ratio of 13:1 and an average review score of 3.2.
What are the most popular zip codes in Windsor, Windsor, VT?
The most popular zip codes in Windsor, Windsor, VT include 05149, 05001, 05751, 03743 and 03773.
What are the most popular neighborhoods near Windsor, Windsor, VT?
The most popular neighborhoods near Windsor, Windsor, VT are West Claremont, North End, West Side, Maple Avenue District and South Woodstock.

Home Trends in Windsor, VT

Housing Trends

Median Sale Price
$274,500
Median Single Family Sale Price
$272,000
Median Townhouse Sale Price
$728,250
Average Price Per Sq Ft
$195
Number of Homes for Sale
7
Last 12 months Home Sales
28
Months of Supply
3.00
Median List Price
$299,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
14%
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