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West Windsor, VT Houses for Sale

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  • /41

    $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 KW Vermont Woodstock

    117 Horseshoe Dr, Brownsville, VT 05037
  • /24

    $1,495,000

    • 7 Beds
    • 6 Baths
    • 5,774 Sq Ft

    310 Pierce Hill Rd, West Windsor, VT 05089

    Unique Two-Home Property with Stunning Mountain Views.Discover this exceptional property featuring two connected homes, seamlessly blending contemporary design with functionality. Originally built in 1975 and expanded in 2000, this unique residence offers a total of 7 bedrooms, perfect for multi-generational living or as a rental opportunity.The newer side of the home showcases beautiful

    Gary Coger Four Seasons Sotheby's Int'l Realty

    310 Pierce Hill Rd, West Windsor, VT 05089
  • /25

    $207,000

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

    295 Hotel Rd Unit 10/10A, Brownsville, VT 05037

    This spacious walk-up condominium features 3 bedrooms and 3 full baths, with an inviting open-concept living and dining area anchored by a cozy fireplace. Step out onto your private deck overlooking the property.This vibrant community offers an unbeatable lifestyle with access to approximately 1,300 acres of outdoor fun, including mountain biking, hiking, cross-country skiing,

    Allison Griep KW Vermont Woodstock

    295 Hotel Rd Unit 10/10A, Brownsville, VT 05037
  • /60

    $1,450,000

    • 6 Beds
    • 5.5 Baths
    • 4,225 Sq Ft

    515 Shattuck Hill Rd Unit 515, 513 & 511, Reading, VT 05062

    Nestled in the tranquil hills of West Windsor, Vermont, Rock Haven Estate is a remarkable 33.49-acre country sanctuary offering three separate luxury homes, set along a private drive & surrounded by nature’s beauty. Whether you're looking for a full-time residence with income-generating opportunities or a private family compound, Rock Haven Estate is a rare find! The Rock House - Hilltop Elegance

    Kate Jarvis Williamson Group Sothebys Intl. Realty

    515 Shattuck Hill Rd Unit 515, 513 & 511, Reading, VT 05062
  • /46

    $1,325,000

    • 4 Beds
    • 2 Baths
    • 2,554 Sq Ft

    325 Cemetery Rd, West Windsor, VT 05089

    Farm at Gaelic Crossing is an equestrian property set on 26.72± acres, has dramatic views of Mount Ascutney and, after summer showers, the frequent and magical appearance of rainbows—often even double rainbows—across the wide, open sky. This updated c.1842 New England Cape offers 2,554 square feet of finished living space, including four bedrooms—two conveniently located on the first floor. Wide

    Story Jenks LandVest, Inc/Woodstock

    325 Cemetery Rd, West Windsor, VT 05089
  • /19

    $299,999 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 right from your door! A short drive to Okemo or Killington. Easy access to I91 and the Upper Valley. Check out the views at the

    Dana Waters Dark Horse Realty

    320 W Rowe Hill Rd, West Windsor, VT 05037
  • /60

    $635,000

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

    298 Jenneville Rd, Windsor, VT 05089

    Welcome to "Valley Brook Farm", a 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, and sun-filled

    John Bassette Bassette Real Estate Group

    298 Jenneville Rd, Windsor, VT 05089

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.

Home Trends in West Windsor, VT

Housing Trends

Median Sale Price
$525,000
Median Single Family Sale Price
$515,000
Median Townhouse Sale Price
$925,000
Median 2 Bedroom Sale Price
$189,945
Median 1 Bedroom Sale Price
$140,500
Average Price Per Sq Ft
$340
Number of Homes for Sale
4
Last 12 months Home Sales
10
Months of Supply
4.80
Median List Price
$520,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
30%
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