12

West Windsor, VT Houses for Sale

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  • /42

    $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
  • /48

    $1,275,000

    • 4 Beds
    • 3 Baths
    • 3,332 Sq Ft

    204 High Ridge Rd, Brownsville, VT 05037

    This hidden gem is one of the best kept secrets in West Windsor. Sited at the end of a private road with rolling green lawns, and a tree top view of Mount Ascutney, this lovingly stewarded home was impeccably constructed and orchestrated with flowing wide open, bright spaces. The perfect home for full or part time living, and entertaining. The living room is anchored by a painted brick Rumford

    Danny Kogut Williamson Group Sothebys Intl. Realty

    204 High Ridge Rd, 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
  • /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
  • /51

    $995,000

    • 4 Beds
    • 3.5 Baths
    • 2,730 Sq Ft

    1777 Bible Hill Rd, Brownsville, VT 05037

    This tidy, well orchestrated Custom Timber Frame Cape is the perfect package! You will love the beautiful, bright spaces that connect seamlessly for every day living and entertaining. Tasteful updates and improvements throughout, this house was designed with convenience in mind. Gleaming hardwood floors run through the main and second level. The roomy country kitchen has soapstone counters, and

    Danny Kogut Williamson Group Sothebys Intl. Realty

    1777 Bible Hill Rd, Brownsville, VT 05037
  • /49

    $625,000

    • 3 Beds
    • 3 Baths
    • 2,680 Sq Ft

    1643 Hammond Hill Rd, West Windsor, VT 05089

    Welcome to your private 8-acre homestead retreat in West Windsor, where nature, comfort, and self-sufficiency come together for everyday adventure. Explore wooded trails, swim in your own peaceful pond, or sip your morning brew on the sunny coffee deck. Evenings shine around the single fire pit, while a handcrafted treehouse brings out the kid in everyone.Grow your own food with raised garden

    Eric Johnston Four Seasons Sotheby's Int'l Realty

    1643 Hammond Hill Rd, West Windsor, VT 05089
  • /33

    $329,000

    • 3 Beds
    • 2 Baths
    • 864 Sq Ft

    1159 Ski Tow Rd, Brownsville, VT 05037

    Located near the end of a country cul-de-sac at Ascutney Mountain this Split entry has 3BR/2BA it is configured as two units with separate entries & 2 kitchens but has been used as a single-family home, as well. It has 2 nice brick fireplaces; one with a VT Castings woodstove insert, the other has a wood stove hook up. Recent updates include a new Rinnai direct vent propane heater, 2 Tesla Power

    Dana Waters Dark Horse Realty

    1159 Ski Tow Rd, Brownsville, VT 05037
  • /60

    $3,650,000

    • 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
  • /55

    $629,000

    • 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
  • /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
  • /59

    $289,500

    • 2 Beds
    • 1 Bath
    • 816 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. Bathroom was upgraded as well. Nothing to do! This gently sloping lot offers a

    John Bassette Bassette Real Estate Group

    1084 Rush Meadow Rd, West Windsor, VT 05037
  • /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, 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
$800,000
Median Single Family Sale Price
$800,000
Median Townhouse Sale Price
$189,945
Median 2 Bedroom Sale Price
$189,945
Median 1 Bedroom Sale Price
$140,500
Average Price Per Sq Ft
$202
Number of Homes for Sale
0
Last 12 months Home Sales
12
Months of Supply
0.00
Median List Price
$925,000
Median Change From 1st List Price
14%
Median Home Sale Price YoY Change
98%
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