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West Windsor, VT Homes for Sale

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  • /44

    $600,000

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

    789 Hammond Hill Rd, West Windsor, VT 05089

    “The Hideaway House”. . . An Oasis of Tranquility. Nestled away in a bowl of woods & set back over 200 feet from the road, this 3-bedroom, 3-full-bath home with attached 2-car garage & extremely high-speed fiber optic Internet offers sanctuary-like privacy situated on 5.52 hillside acres in fashionable West Windsor, VT. This welcoming residence is secluded serenity at its best & is located in

    Agent Photo

    Ross Doody

    Century 21 Highview Realty

    (802) 461-4869

    789 Hammond Hill Rd, West Windsor, VT 05089
  • /55

    $669,000

    • 3 Beds
    • 3.5 Baths
    • 2,391 Sq Ft

    3440 Route 44, West Windsor, VT 05037

    This well cared for contemporary home has only been used as a second home for the original owners. The house takes advantage of the southwest exposure to be able to bring the outside in with the use of large palladium windows and multiple French doors. Some of the interior features include 3 woodburning fireplaces ,wide pine floors ,vaulted ceilings ,and skylights. The floor plan has an easy

    Carol Wood Williamson Group Sothebys Intl. Realty

    3440 Route 44, West Windsor, 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

    Story Jenks LandVest, Inc/Woodstock

    325 Cemetery Rd, West Windsor, VT 05089
  • /35

    $621,000

    • 3 Beds
    • 3 Baths
    • 2,915 Sq Ft

    1643 Hammond Hill Rd, West Windsor, VT 05089

    Discover your homestead dream on 8 acres of beautiful land that’s been incredibly loved and improved upon in the last 18 years. The classic farmhouse has hardwood floors, big kitchen, dining room and spacious living with den, 2 bathrooms and 2 bedrooms. In addition, this unique property now has a 2 car garage and living space above it that includes large office and1-BR apt for guests, family or

    Daniel Preston KW Vermont Woodstock

    1643 Hammond Hill Rd, West Windsor, VT 05089
  • /36

    $525,000 Open Sun 10AM - 12PM

    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft

    65 Bergland Ln, West Windsor, VT 05089

    Delayed showings begin at the Open House on Sunday, June 29th from 10 AM to 12 PM!Tucked at the end of a quiet road, this charming contemporary home sits on over 10 acres with a private pond, open meadow, and wooded privacy. Sunshine pours into the bright living spaces, and the back deck offers a perfect spot to relax and overlook the water. A backyard chicken coop can keep you stocked with

    Holly Hall Hall Collins Real Estate Group

    65 Bergland Ln, 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 tubing hill and take in all the action just outside your door!This vibrant community offers an unbeatable lifestyle with access to approximately 1,300 acres of outdoor fun, including

    Allison Griep KW Vermont Woodstock

    295 Hotel Rd Unit 10/10A, Brownsville, VT 05037
  • /30

    $544,000

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

    586 Ski Tow Rd, Brownsville, VT 05037

    Adorable & Turn-key 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, extensive

    Dana Waters Dark Horse Realty

    586 Ski Tow Rd, Brownsville, VT 05037
  • /48

    $215,000

    • 3 Beds
    • 3 Baths
    • 1,600 Sq Ft

    295 Hotel Rd Unit 17, Brownsville, VT 05037

    OWN FOR LESS THAN YOU CAN RENT!! Spacious and bright end unit condo on Ascutney Mountain. Fireplaced living room, dining area with balcony, kitchen and even an entry enclave. 3 bedrooms with 3 full baths. 1 bed/bath on 1st floor. 2 bedrooms, 2 baths, multiple closets and a sitting area on the upper level. The advantage of the 3rd floor is that you get the loft area, cathedral ceilings and some

    Crystal Moses Crystal Moses

    295 Hotel Rd Unit 17, Brownsville, VT 05037
  • /60

    $1,597,000

    • 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
  • /59

    $289,500

    • 2 Beds
    • 1 Bath
    • 996 Sq Ft

    1084 Rush Meadow Rd, West Windsor, VT 05037

    Attractive two bedroom, 1 bath ranch style home on a serene 1.08-acre parcel nestled along scenic Rush Meadow Road in West Windsor. Right in the heart of Horse Country! The kitchen has upgraded cabinetry and there is overflow third bedroom space in the lower level that can be turned into home office or den usage. This gently sloping lot offers a harmonious blend of open lawn and pleasant

    John Bassette Bassette Real Estate Group

    1084 Rush Meadow Rd, West Windsor, VT 05037
  • /16

    $410,000

    • Land
    • 10 Acres
    • $40,196 per Acre

    181 Banister Rd, West Windsor, VT 05037

    Over 10 acres of beautiful fields and pasture with long range views and stone walls lining the property. Mature trees dot the perimeter and a lovely stream runs along the roadside. There is a multilevel functioning barn with water and electricity and a small gated paddock off to the side. Located in the heart of Horse Country, this would be and ideal equestrian property or a great place to raise

    Dan Noble Snyder Donegan Real Estate Group

    181 Banister Rd, West Windsor, VT 05037
  • /16

    $410,000

    • 3 Beds
    • 1 Bath
    • 1,620 Sq Ft

    181 Banister Rd, Windsor, VT 05089

    Over 10 acres of beautiful fields and pasture with long range views and stone walls lining the property. Mature trees dot the perimeter and a lovely stream runs along the roadside. There is a multilevel functioning barn with water and electricity and a small gated paddock off to the side. Located in the heart of Horse Country, this would be and ideal equestrian property or a great place to raise

    Dan Noble Snyder Donegan Real Estate Group

    181 Banister Rd, Windsor, VT 05089
  • /46

    $1,665,000

    • 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
  • /19

    $325,000 New Construction

    • 1,308 Sq Ft

    320 W Rowe Hill Rd, West Windsor, VT 05037

    Wonderful unfinished 24'x34' pole building originally planned to be a stable with an efficiency apartment above now permitted to be a 2 bedroom, 2 bath residence on 9.4 tranquil acres on W Rowe Hill Rd. Sellers say zoning will permit either style.Check out the views at the height of the land or sit by the babbling brook as you plan the completion of this project. The sellers have used all quality

    Dana Waters Dark Horse Realty

    320 W Rowe Hill Rd, West Windsor, VT 05037

Why Live in West Windsor

West Windsor is a rural township in Vermont, approximately 9 miles from the New Hampshire border and the Connecticut River. The area is characterized by woods and farmland surrounding the village of Brownsville, near Mount Ascutney, the tallest mountain in Windsor County. The community has a strong outdoorsy spirit, evident in local attractions like the volunteer-run ski area and the annual 100-mile race. Nearby towns such as Woodstock and Windsor provide essential shopping and dining options, with larger stores available in West Lebanon and Claremont, New Hampshire. Homes in West Windsor range from ranch-style properties to large estates with mountain views, often situated on expansive farmland or among tall trees. The crime rate is lower than the national average, contributing to the area's appeal. Mount Ascutney offers recreational activities, including hiking trails and a state park, with trails like the Summit Loop and Bicentennial Trail accessible to residents. The community hosts events such as the Vermont 100 race, Flow State Mountain Bike Festival, and West Windsor Music Festival. Brownsville Butcher & Pantry serves as a local hub, offering produce, seafood, and café meals. Main roads include Vermont Route 44 and Vermont Route 106, connecting residents to nearby towns. Windsor, about 6 miles east, provides additional amenities, including a supermarket and dining options like Windsor Station Restaurant & Bar. Amtrak service is available in Windsor, and Burlington International Airport is about 105 miles away.

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 $570,709.
How many homes have sold over the last 12 months in West Windsor, VT?
24 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 05149, 05001, 05751, 03743 and 03773.
How much do you need to make to afford a house in West Windsor?
The median home price in West Windsor is $499,000. If you put a 20% down payment of $99,800 and had a 30-year fixed mortgage with an interest rate of 6.77%, your estimated principal and interest payment would be $2,590 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $111K a year to afford the median home price in West Windsor.
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, Weathersfield School and Albert Bridge School. Browse all the schools in West Windsor, VT to learn more.

Home Trends in West Windsor, VT

Housing Trends

Median Sale Price
$400,000
Median Single Family Sale Price
$525,000
Median Townhouse Sale Price
$610,500
Median 1 Bedroom Sale Price
$140,500
Average Price Per Sq Ft
$263
Number of Homes for Sale
9
Last 12 months Home Sales
24
Months of Supply
4.50
Median List Price
$499,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
3%
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