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Windsor, VT Houses for Sale

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  • /36

    $250,000

    • 3 Beds
    • 1.5 Baths
    • 1,900 Sq Ft

    31 Maple St, Windsor, VT 05089

    Discover classic Vermont charm in this 3-bedroom, 1.5-bathroom home located on a quiet, tree-lined street just steps from downtown Windsor. This home is perfect for those who appreciate historic charm and are ready to make it their own. Inside, you’ll find a welcoming layout and abundant natural light. The first floor features a full bathroom, laundry, spacious living and dining areas, and an

    Tara Reeves Vermont Real Estate Company

    31 Maple St, Windsor, VT 05089
  • /55

    $629,000

    • 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 maintenance-free manufactured cedar-tone shingles on the entire house and workshop shed. The kitchen

    Danny Kogut Williamson Group Sothebys Intl. Realty

    3361 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
  • /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
  • /29

    $199,900

    • 4 Beds
    • 1.5 Baths
    • 2,310 Sq Ft

    9 Main St, Windsor, VT 05089

    A Grand Old Home Full of Character and PotentialWhat a beauty this home once was—and can be again! Brimming with historic charm, this spacious residence is just waiting for someone to restore it to its full glory. From the high ceilings and rich pecan woodwork to the elegant crown moldings and soapstone countertops, the original details create a timeless backdrop for your

    Linda Benoit Highland Realty

    9 Main St, Windsor, VT 05089

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.

Home Trends in Windsor, VT

Housing Trends

Median Sale Price
$540,000
Median Single Family Sale Price
$540,000
Average Price Per Sq Ft
$409
Number of Homes for Sale
0
Last 12 months Home Sales
13
Months of Supply
0.00
Median List Price
$574,900
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
126%
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