8

Windsor, VT Houses for Sale

Section Image
  • /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
  • /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
  • /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

Why Live in Windsor

Windsor, nestled in the shadow of Mount Ascutney and along the Connecticut River, is a historic township with around 3,500 residents. Known as the "birthplace of Vermont," it offers a mix of outdoor recreation, shops, and dining options in its small downtown area. The neighborhood has seen an influx of younger residents since 2020, drawn by the remote work lifestyle. Homes vary from late 1700s and mid-1800s builds to Cape Cods and ranch-style homes from the 1930s to 1950s. Properties range from smaller lots in town to expansive country lots with dense woods or open farmland. Windsor's crime rate is lower than the national average. Outdoor enthusiasts can enjoy Paradise Park's trails, Mount Ascutney's revived recreational facilities, and canoeing or kayaking with Great River Outfitters. Downtown Windsor features Artisans Park with Harpoon Brewery, Silo Distillery, and more, while Windsor Station Restaurant and Barroom offers a unique dining experience in an old train depot. The Autumn Moon Festival and a year-round farmers market add to the local charm. Windsor School serves pre-kindergarten through 12th grade. The town is well-connected with Interstate 91, U.S. Route 5, and daily Amtrak service, with Claremont, New Hampshire, just 10 miles away.

Home Trends in Windsor, VT

Housing Trends

Median Sale Price
$275,000
Median Single Family Sale Price
$274,500
Median Townhouse Sale Price
$728,250
Average Price Per Sq Ft
$195
Number of Homes for Sale
8
Last 12 months Home Sales
30
Months of Supply
3.20
Median List Price
$299,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
8%
How to Buy a Home How to Finance a Home How to Sell a Home