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Newest Homes for Sale in Windsor, VT

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  • /14

    $225,000

    • 3 Beds
    • 1 Bath
    • 1,095 Sq Ft

    24 Cherry St, Windsor, VT 05089

    Offers are in: Best and Final Offers due Monday 7/13/26 at 6pm Looking for an affordable way into homeownership? This ranch features 3 bedrooms and 1 full bath, this single-level home is perfect for first-time buyers or downsizers. Cozy up in the living room next to the fireplace or relax on the covered porch with your morning coffee. The easy, one-floor layout means low-maintenance living at a

    Allison Griep BHHS Verani Upper Valley

    24 Cherry St, Windsor, VT 05089
  • /43

    $1,495,000

    • Land
    • 48.11 Acres
    • $31,075 per Acre

    1 US Route 5 Rd, Hartland, VT 05048

    48.11 Acres of Spectacular Vermont Land with Panoramic Views!Discover a rare opportunity to own 48.11 acres of exceptional Vermont countryside in the heart of the Connecticut River Valley, often referred to as Vermont's "Shenandoah Valley" for its scenic beauty. This remarkable property offers breathtaking 180-degree views to the east and south, creating an unforgettable setting for a dream

    Charles Bacon Quechee Lakes Real Estate Center

    1 US Route 5 Rd, Hartland, VT 05048
  • /55

    $1,625,000

    • 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
  • /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

    $510,000

    $25K 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
  • /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
  • /38

    $413,900

    $10K PRICE DROP
    • 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
  • /26

    $110,000

    $9K 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
  • /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
  • /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

Frequently Asked Questions

What is the average home price in Windsor, VT?
Homes for sale in Windsor, VT have an average home price of $369,381.
Are home prices dropping in Windsor?
Yes, home prices in Windsor are down 22% in the last 12 months.
How many homes have sold over the last 12 months in Windsor, VT?
29 homes have sold in Windsor, VT over the last 12 months.
What is the average household income in Windsor, VT?
The average household income in Windsor, VT is $68K.
What are the most popular zip codes in Windsor, VT?
The most popular zip codes in Windsor, VT include 05089, 05037, 05048, 03745 and 03781.
How much do you need to make to afford a house in Windsor?
The median home price in Windsor is $292,500. If you put a 20% down payment of $58,500 and had a 30-year fixed mortgage with an interest rate of 6.49%, your estimated principal and interest payment would be $1,480 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. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Windsor is $68K.
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 Price Trends

Median Sale Price
$290,000
Median Single Family Sale Price
$257,750
Median Townhouse Sale Price
$500,000
Median 2 Bedroom Sale Price
$299,000
Median 1 Bedroom Sale Price
$139,000
Average Price Per Sq Ft
$212
Number of Homes for Sale
8
Last 12 months Home Sales
29
Months of Supply
3.30
Median List Price
$292,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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