5

West Windsor, VT Houses for Sale

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  • 789 Hammond Hill Rd, West Windsor, VT 05089
    789 Hammond Hill Rd, West Windsor, VT 05089
    789 Hammond Hill Rd, West Windsor, VT 05089
    /48

    $500,000

    • 3 Beds
    • 3 Baths
    • 1,826 Sq Ft

    789 Hammond Hill Rd, West Windsor, VT 05089

    "The Hideaway House - A Private Sanctuary”: This light-filled contemporary retreat located high on a hill in fashionable West Windsor is the quintessential "Goldilocks" Vermont property. It offers a private woodland sanctuary where quiet tranquility and architectural highlights meet. Tucked into a secluded 5.52-acre wooded bowl and set back over 200 ft. from the road, this tasteful 3BR/3BA home

    Agent Photo

    Ross Doody

    Century 21 Highview Realty

    (802) 523-2984

    789 Hammond Hill Rd, West Windsor, VT 05089
  • 117 Horseshoe Dr, Brownsville, VT 05037
    117 Horseshoe Dr, Brownsville, VT 05037
    117 Horseshoe Dr, Brownsville, VT 05037
    /44

    $849,900

    • 3 Beds
    • 3 Baths
    • 3,392 Sq Ft

    117 Horseshoe Dr, Brownsville, VT 05037

    Experience Vermont living at its finest in this custom-built home, thoughtfully designed by the builder for exceptional energy efficiency and year-round comfort. Perfect as a relaxing getaway, this property offers expansive sleeping spaces ideal for hosting family and friends. Spend your days exploring the nearby VAST Trail system or Ascutney Mountain, and your evenings unwinding by the

    Katie Ladue Gilbert BHHS Verani Upper Valley

    117 Horseshoe Dr, Brownsville, VT 05037
  • 290 Village Ln, Brownsville, VT 05037
    290 Village Ln, Brownsville, VT 05037
    290 Village Ln, Brownsville, VT 05037
    /15

    $325,000

    • 2 Beds
    • 2 Baths
    • 1,604 Sq Ft

    290 Village Ln, Brownsville, VT 05037

    Privately sited at the end of a quiet dead end road on beautiful Mt. Ascutney, this cozy 2 BR, 2 BA Chalet style home is an ideal-low maintenance vacation home, or an efficient starter. LR/DR with cathedral ceiling anchored by a sweeping fieldstone fireplace, with woodstove insert; and a spiral staircase leading to a loft-perfect for your home office. Kitchen with built ins, and updated

    Danny Kogut Williamson Group Sothebys Intl. Realty

    290 Village Ln, Brownsville, VT 05037
  • 320 W Rowe Hill Rd, West Windsor, VT 05037
    320 W Rowe Hill Rd, West Windsor, VT 05037
    320 W Rowe Hill Rd, West Windsor, VT 05037
    /20

    $279,900 New Construction

    • 1,308 Sq Ft

    320 W Rowe Hill Rd, West Windsor, VT 05037

    Wonderful unfinished 24'x34' pole building, a rare opportunity to shape a home or getaway that fits your lifestyle perfectly on 9.4 tranquil acres on W Rowe Hill Rd. On VAST trail, great trail location for year round recreation. Close to GMHA & Ascutney Outdoors, ride your horse, bike or sled right from your door! A short drive to Okemo or Killington. Easy access to I91 and the Upper Valley.

    Dana Waters Dark Horse Realty

    320 W Rowe Hill Rd, West Windsor, VT 05037
  • 298 Jenneville Rd, Windsor, VT 05089
    298 Jenneville Rd, Windsor, VT 05089
    298 Jenneville Rd, Windsor, VT 05089
    /57

    $565,000

    • 4 Beds
    • 2 Baths
    • 2,212 Sq Ft

    298 Jenneville Rd, Windsor, VT 05089

    PRICE REDUCED! Welcome to "Valley Brook Farm", an historic cape in the middle of horse country on 12.92 acres with barns, rolling & level pasture, a swimming pond, and brook. Located in the heart of the nationally renowned Green Mountain Horse Association trail network. Nestled on scenic & bucolic Jenneville Road, this c. 1820 cape offers the warmth of wide pine floors, post-and-beam character,

    John Bassette Bassette Real Estate Group

    298 Jenneville Rd, Windsor, VT 05089
Vermont Windsor County West Windsor

Houses for Sale in West Windsor, VT

Why Live in West Windsor

West Windsor, Vermont, is a rural township located approximately 9 miles from the New Hampshire border and the Connecticut River. The area is characterized by its wooded landscapes and farmland surrounding Mount Ascutney, the tallest mountain in Windsor County. The community spirit is evident in local establishments like the Brownsville Butcher & Pantry and the volunteer-run ski area on the mountain. Nearby towns such as Woodstock and Windsor provide essential shopping and dining options, with larger stores available in West Lebanon and Claremont, New Hampshire. Housing in West Windsor includes ranch-style homes and secluded estates, with properties often featuring expansive yards and outbuildings. The median price for a single-family home is about $610,000, and the area has a low crime risk compared to the national average. Mount Ascutney offers recreational activities including hiking trails and a state park, with trails like the Summit Loop and Bicentennial Trail accessible to residents. Annual events such as the Vermont 100 race, Flow State Mountain Bike Festival, and West Windsor Music Festival highlight the town's outdoorsy culture. The local Albert Bridge School serves younger students, while older students attend Windsor School. Dining options include Brownsville Butcher & Pantry's café and the Maple Kitchen at the Holiday Inn Mount Ascutney Resort. Main roads like Vermont Route 44 and Vermont Route 106 connect West Windsor to nearby towns, with additional amenities and healthcare available in Windsor, about 6 miles away. Amtrak services Windsor, and Burlington International Airport is roughly 105 miles from West Windsor.

Learn more about living in West Windsor

Home Trends in West Windsor, VT

On average, homes in West Windsor, VT sell after 45 days on the market compared to the national average of 55 days. The median sale price for homes in West Windsor, VT over the last 12 months is $525,000, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$525,000
Median Single Family Sale Price
$515,000
Median Townhouse Sale Price
$457,500
Median 2 Bedroom Sale Price
$189,945
Median 1 Bedroom Sale Price
$140,500
Average Price Per Sq Ft
$334
Number of Homes for Sale
5
Last 12 months Home Sales
14
Months of Supply
4.30
Median List Price
$499,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
How to Buy a Home How to Finance a Home How to Sell a Home

In West Windsor, there are currently 5 houses for sale, offering an array of options for potential buyers. With houses priced between $279,900 to $849,900, there's a range to accomodate every budget. As of April, 2026 the median home price in West Windsor is $499,900, while the average sale price is $790,710, offering insights into the local housing market. On average, houses spend 45 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in West Windsor, VT and find the perfect place to call home.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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