11

Windsor, VT Homes for Sale

Section Image
  • /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
  • /13

    $229,000

    • 2 Beds
    • 1 Bath
    • 1,008 Sq Ft

    15 National St, Windsor, VT 05089

    Experience the rare opportunity to own a BRAND NEW home, located in the heart of Windsor. This home seamlessly blends efficiency with style, featuring a thoughtfully elevated foundation designed to sit securely out of the flood zone for total peace of mind. The interior offers open living on the first level, and generous sized bedrooms upstairs, maximizing all the available space. The exterior

    Chelsea Bevis KW Vermont Woodstock

    15 National St, Windsor, VT 05089
  • /43

    $875,000

    • 2 Beds
    • 2 Baths
    • 1,820 Sq Ft

    860 Yale Heights Rd, Windsor, VT 05089

    This impeccably orchestrated cottage style contemporary home was crafted by Ennis Builders in 2006 with an eye to meticulous detail. The sweeping cherry spiral staircase, beautiful stonework and superior fit and finish imbue a quality of workmanship that reflects throughout the home. The main level features an open-concept kitchen with maple butcher block counters, and quality stainless steel

    Danny Kogut Williamson Group Sothebys Intl. Realty

    860 Yale Heights Rd, 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
  • /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
  • /10

    $229,000

    • 2 Beds
    • 1 Bath
    • 1,008 Sq Ft

    29 National St, Windsor, VT 05089

    Take a look at this rare chance to own a BRAND NEW home in the heart of Windsor. Built for efficiency, the house features a raised foundation to keep it out of the flood zone for extra peace of mind. The layout is practical and spacious, offering an open-concept first floor and large bedrooms upstairs.You are within walking distance to the Amtrak station and downtown, and our local Moover

    Chelsea Bevis KW Vermont Woodstock

    29 National St, Windsor, VT 05089
  • /25

    $329,000

    • 4 Beds
    • 2 Baths
    • 2,142 Sq Ft

    74 Union St, Windsor, VT 05089

    Discover space, flexibility, and everyday convenience in this charming 4-bedroom, 2-bath home in the heart of Windsor. Thoughtfully designed with a spacious floor plan, the main living area features warm hardwood floors and abundant natural light, creating a bright and welcoming atmosphere throughout. The formal dining area flows seamlessly into the living room, perfect for both everyday living

    Chelsea Bevis KW Vermont Woodstock

    74 Union St, Windsor, VT 05089
  • /26

    $119,000

    • 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

    $413,900

    • 4 Beds
    • 2.5 Baths
    • 2,888 Sq Ft

    273 Route 5 N, Windsor, VT 05089

    Motivated seller! Price drop! A rare piece of Vermont history, thoughtfully preserved for modern living. Dating to 1790, this distinguished brick and frame Colonial stands as a testament to early New England craftsmanship — and it's ready for its next chapter. Meticulously maintained over the centuries and updated where it counts, this two-story home offers the warmth of wide-plank hardwood and

    Allison Griep BHHS Verani Upper Valley

    273 Route 5 N, Windsor, VT 05089
  • /15

    $96,232 New Construction

    • 2 Beds
    • 2 Baths
    • 777 Sq Ft

    108 Cubb Ct, Windsor, VT 05089

    Welcome to 132 Cubb Court, 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

    108 Cubb Ct, 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

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 $319,711.
Are home prices dropping in Windsor?
Yes, home prices in Windsor are down 20% in the last 12 months.
How many homes have sold over the last 12 months in Windsor, VT?
39 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, 03781, 05151 and 05048.
How much do you need to make to afford a house in Windsor?
The median home price in Windsor is $289,000. If you put a 20% down payment of $57,800 and had a 30-year fixed mortgage with an interest rate of 6.3%, your estimated principal and interest payment would be $1,430 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $61K a year to afford the median home price in Windsor. Learn how much home you can afford with our Home Affordability Calculator.
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 Hartland Elementary School, Weathersfield School and Cornish Elementary School. Browse all the schools in Windsor, VT to learn more.

Home Trends in Windsor, VT

Housing Trends

Median Sale Price
$274,000
Median Single Family Sale Price
$259,000
Median Townhouse Sale Price
$399,500
Average Price Per Sq Ft
$193
Number of Homes for Sale
6
Last 12 months Home Sales
39
Months of Supply
1.80
Median List Price
$289,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-7%
How to Buy a Home How to Finance a Home How to Sell a Home