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West Windsor, VT Homes for Sale

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  • /57

    $535,000

    • 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,

    Agent Photo

    John Bassette

    Bassette Real Estate Group

    (802) 802-3094

    298 Jenneville Rd, Windsor, VT 05089
  • /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
  • /32

    $299,900

    • 3 Beds
    • 2.5 Baths
    • 1,614 Sq Ft

    127 Mountains Edge Rd Unit 211, Brownsville, VT 05037

    Immaculate end-unit condominium offering the ease of single-floor living at its finest. Thoughtfully maintained and move-in ready, this home impresses from the moment you walk in- tasteful finishes throughout create a polished, welcoming atmosphere. Newer windows flood the space with natural light, and a new heating system ensures year-round comfort. The primary suite features a beautifully

    Katie Ladue Gilbert BHHS Verani Upper Valley

    127 Mountains Edge Rd Unit 211, Brownsville, VT 05037
  • /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
  • /22

    $279,900

    • Land
    • 9.4 Acres
    • $29,777 per Acre

    320 W Rowe Hill Rd, West Windsor, VT 05037

    On VAST trail, great trail location close to GMHA & Ascutney Outdoors, ride your horse, bike or sled from your door. A rare opportunity to shape a home or getaway that fits your lifestyle on 9.4 acres on class 4 road. The sellers have used all quality materials in a wonderful 24'x34' unfinished pole building, road upgrades to the property are done, state WW permit allows for 3 BR septic system,

    Dana Waters Dark Horse Realty

    320 W Rowe Hill Rd, West Windsor, VT 05037
  • /19

    $95,000

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft

    1500 Brownsville-Hartland Rd, West Windsor, VT 05089

    Here's a chance to own your own property in West Windsor. This 3/4 +/- acre of land abuts one side up to Beaver Brook and you get views of Mt. Ascutney on the other side. This older mobile home with basement, offers the perfect opportunity for an investor. Restore the homes vintage charm or you could modernize the site with a new mobile unit. This was constructed as a 2-bedroom 1 bath home. One

    Ann Jacques Century 21 Highview Realty

    1500 Brownsville-Hartland Rd, West Windsor, VT 05089
  • /59

    $930,000

    • 4 Beds
    • 2.5 Baths
    • 2,352 Sq Ft

    567 Churchill Rd, Brownsville, VT 05037

    Discover a truly rare opportunity to own an extraordinary piece of Vermont countryside. This 4-bedroom, 3-bath home is set on 80 acres of pristine woodland with nearly a full mile of road frontage for exceptional accessibility and future potential. Lovingly held by the same family for over 60 years, the property is rich in history, with classic stone wall boundary lines that echo its past. This

    Julie Davis KW Vermont Woodstock

    567 Churchill Rd, Brownsville, VT 05037
  • /24

    $474,800

    • 3 Beds
    • 2 Baths
    • 1,480 Sq Ft

    586 Ski Tow Rd, Brownsville, VT 05037

    Adorable partially furnished 3 bedroom, 2 bath home on landscaped 1.53 acres corner lot in the heart of Ascutney Mt Resort! Many upgrades including Bosch High Efficiency Propane Boiler, Mitsubishi heat pump/AC, Rinnai on demand hot water heater, new well tank & centrifuge filtration system, new fireplace & chimney with Woodstock soapstone woodstove flanked by custom cabinets on each side. Decks,

    Dana Waters Dark Horse Realty

    586 Ski Tow Rd, Brownsville, VT 05037
  • /26

    $309,000

    • 3 Beds
    • 3 Baths
    • 1,594 Sq Ft

    70 Mountains Edge Rd Unit 606, West Windsor, VT 05037

    Tucked away from the other buildings, this unique three-bedroom, three-bath condominium offers a peaceful setting with wooded views from all three private balconies. Thoughtfully remodeled, the home features newer hardwood flooring, updated carpeting, and tastefully renovated bathrooms. The open-concept main level includes a comfortable kitchen with a breakfast bar, a dedicated dining area, and

    Gerry Stark RE/MAX Upper Valley

    70 Mountains Edge Rd Unit 606, West Windsor, VT 05037
  • /36

    $310,000

    • 3 Beds
    • 2.5 Baths
    • 1,824 Sq Ft

    70 Mountains Edge Rd Unit 603, West Windsor, VT 05037

    This inviting condo offers the perfect blend of comfort, convenience, and year-round outdoor access. Step right outside your back door to enjoy scenic hiking and biking trails, while world-class skiing and snowboarding are just moments away. This unique home features two separate floors, ideal for flexible living. The first floor offers its own private entrance, along with dedicated bedrooms and

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    70 Mountains Edge Rd Unit 603, West Windsor, VT 05037
  • /60

    $3,350,000

    • 5 Beds
    • 5 Baths
    • 3,212 Sq Ft

    166 Jewett Rd, Brownsville, VT 05037

    Stately hilltop home built by Silas Banister c.1800, recently undergone a complete restoration. Quality materials & craftsmanship throughout. It has gorgeous views of nearby Ascutney Mountain & long-range views of NH. The property consists of 98 acres made up of fields, hard & softwoods, trails, a large sugarbush (potential for a future boiling operation). Conserved by Upper Valley Land Trust,

    Dana Waters Dark Horse Realty

    166 Jewett Rd, Brownsville, VT 05037

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.

Frequently Asked Questions

What is the average home price in West Windsor, VT?
Homes for sale in West Windsor, VT have an average home price of $696,045.
How many homes have sold over the last 12 months in West Windsor, VT?
14 homes have sold in West Windsor, VT over the last 12 months.
What are the most popular zip codes in West Windsor, VT?
The most popular zip codes in West Windsor, VT include 05037, 05089, 05048, 05151 and 05153.
How much do you need to make to afford a house in West Windsor?
The median home price in West Windsor is $404,950. If you put a 20% down payment of $81,000 and had a 30-year fixed mortgage with an interest rate of 6.23%, your estimated principal and interest payment would be $1,990 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $85K a year to afford the median home price in West Windsor. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in West Windsor, VT?
West Windsor, VT has highly rated public and private schools. Some of the best schools in West Windsor based on Niche Grades are Cavendish Town Elementary School, Albert Bridge School and Hartland Elementary School. Browse all the schools in West Windsor, VT to learn more.

Home Trends in West Windsor, VT

Housing Trends

Median Sale Price
$525,000
Median Single Family Sale Price
$515,000
Median Townhouse Sale Price
$494,000
Median 2 Bedroom Sale Price
$189,945
Median 1 Bedroom Sale Price
$140,500
Average Price Per Sq Ft
$339
Number of Homes for Sale
5
Last 12 months Home Sales
14
Months of Supply
4.30
Median List Price
$404,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
25%
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