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Windsor, VT Houses for Sale

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  • /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

    $500,000

    $35K 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

    Open Sun 10AM - 12PM
    • 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
  • /16

    $299,000

    • 2 Beds
    • 1 Bath
    • 1,152 Sq Ft

    319 Back Mountain Rd, Windsor, VT 05089

    Welcome to 319 Back Mountain Road in Windsor, Vermont, a comfortable 2-bedroom ranch situated on approximately one acre in a peaceful country setting. The home features an updated kitchen and a spacious living and dining area with plenty of natural light, creating a warm and inviting space for everyday living and entertaining. A metal roof and updated heating system add to the home's practicality

    Kate Cassidy Four Seasons Sotheby's Int'l Realty

    319 Back Mountain Rd, 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

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.

Single Family Home Price Trends

Median Home Price
$272,000
Median 3-Bedroom Home Price
$271,000
Median 4-Bedroom Home Price
$400,000
Median 5-Bedroom Home Price
$115,000
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