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Windsor, VT Homes for Sale

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  • /36

    $139,000

    • 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
  • /38

    $435,000

    • 4 Beds
    • 2.5 Baths
    • 2,272 Sq Ft

    96 Dairy Ln, Windsor, VT 05089

    Before the leaves have fallen, the PRICE on this one has! Nestled on 1.34 picturesque acres in historic Windsor, this classic 4-bedroom Colonial blends timeless charm with comfortable living. Set back from the road, the home offers privacy and space to enjoy Vermont’s natural beauty while being just minutes from town amenities, schools, and I-91.Inside, you'll find a traditional floor

    Katie Ladue Gilbert KW Vermont Woodstock

    96 Dairy Ln, Windsor, VT 05089
  • /55

    $598,000

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

    3440 Route 44, West Windsor, VT 05037

    Views of Mt. Ascutney from this well cared for contemporary home that 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.

    Carol Wood Williamson Group Sothebys Intl. Realty

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

    $575,000

    • 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
  • /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
  • /16

    $390,000

    • 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
  • /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
  • /16

    $96,232 New Construction

    • 2 Beds
    • 2 Baths
    • 777 Sq Ft

    11 Cubb Ct, Windsor, VT 05089

    Welcome to 11 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

    Kate Barry EXP Realty

    11 Cubb Ct, Windsor, VT 05089
  • /11

    $87,826 New Construction

    • 1 Bed
    • 1 Bath
    • 643 Sq Ft

    23 Cubb Ct, Windsor, VT 05089

    Welcome to 23 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 1 bedroom, 1 bathroom, and 643 sq. ft. (13'4"x48) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

    Kate Barry EXP Realty

    23 Cubb Ct, Windsor, VT 05089
  • /16

    $96,232 New Construction

    • 2 Beds
    • 2 Baths
    • 777 Sq Ft

    517 Back Mountain Rd, Windsor, VT 05089

    Welcome to 517 Back Mountain Rd., Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

    Kate Barry EXP Realty

    517 Back Mountain Rd, Windsor, VT 05089
  • /11

    $98,995 New Construction

    • 3 Beds
    • 2 Baths
    • 880 Sq Ft

    84 Cubb Ct, Windsor, VT 05089

    Welcome to 84 Cubb Court, , Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-66 model manufactured home offers 3 bedrooms, 2 bathrooms, and 880 sq. ft. (13'4"x66) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

    Kate Barry EXP Realty

    84 Cubb Ct, 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.

Frequently Asked Questions

What is the average home price in Windsor, VT?
Homes for sale in Windsor, VT have an average home price of $355,452.
How many homes have sold over the last 12 months in Windsor, VT?
42 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 05089, 05037, 03745, 03781 and 05048.
How much do you need to make to afford a house in Windsor?
The median home price in Windsor is $295,750. If you put a 20% down payment of $59,200 and had a 30-year fixed mortgage with an interest rate of 6.35%, your estimated principal and interest payment would be $1,470 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $63K 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
$278,250
Median Single Family Sale Price
$274,500
Median Townhouse Sale Price
$821,500
Average Price Per Sq Ft
$199
Number of Homes for Sale
6
Last 12 months Home Sales
42
Months of Supply
1.70
Median List Price
$295,750
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
2%
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