You are viewing West Windsor VT Homes between $500000 and $1000000 dollars.
Under Contract
$548,000 $229 per sq.ft. Village of Brownsville in Town of West Windsor VT Home »
3 Beds | 4 Baths | Total Sq. Ft. 2391 | Acres: 1.49Listed on Friday May 15, 2026
Description: Views of Mt. Ascutney from this well cared for contemporary home that 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 flow. The charming kitchen leads into a spacious dining room with fireplace. The living room with stunning fireplace leads out to a large deck for outdoor dining. Off of the living room the cozy family room features a wall of built-in bookcases. The downstairs bedroom complete with private bath opens onto the spacious screened in porch. The primary bedroom is upstairs. It features a built in king sized bed with drawers for extra storage, walk in closets ,and full bath. also on the second floor is another bedroom and bath with walk in shower. The grounds of mature gardens, antique apple trees , blueberry, raspberry bushes ,and original stone walls that border the north and east boundaries create a magical setting. There is ample land to add a garage. Easy access to the Upper Valley with all of the amenities including shopping , Dartmouth College , and world class Dartmouth Medical Center. Woodstock, named by many magazines one of the prettiest small towns in America is less than 25 minutes away.5 hrs to NYC 2 hrs to Boston. See Listing Details & 55 images.
$599,000 $250 per sq.ft. West Windsor VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 3200 | Acres: 3.2Listed on Saturday May 2, 2026
Description: This is one of those homes you simply have to experience in person. The views alone are worth the visit. Perched above the valley with commanding, panoramic views of Mount Ascutney, this exceptional custom-built home offers a front-row seat to some of Vermont's most breathtaking scenery. From sunrise over the mountains to spectacular evening sunsets, every window showcases a landscape that changes beautifully with the seasons. Designed for comfortable everyday living and effortless entertaining, this thoughtfully crafted four-bedroom, three-bath home features the convenience of a first-floor primary suite, while three spacious upstairs bedrooms provide room for family, guests, or dedicated home office space. The finished walkout lower level adds even more flexibility with a bonus bedroom, expansive recreation room, and the potential for an in-law suite, guest quarters, or private workspace with its own entrance. Step outside onto the impressive 900-square-foot deck, where you'll enjoy outdoor dining, morning coffee, and unforgettable gatherings overlooking the mountains and valley below. The spacious yard offers plenty of room for gardening, recreation, or simply enjoying Vermont's abundant wildlife. A charming, well-built chicken coop adds a touch of country living and farmhouse appeal. Built with efficiency in mind, the home's passive solar greenhouse roof system captures and stores natural heat, helping reduce energy costs while embracing sustainable Vermont living. Located in the highly desirable West Windsor community, you'll enjoy easy access to Mount Ascutney, Ascutney Outdoors, miles of hiking and biking trails, the renowned VAST snowmobile trail system, and world-class skiing at Okemo and Killington. The villages of Woodstock, Brownsville, and the Upper Valley are all within easy reach, making this an ideal year-round residence or Vermont getaway. Custom homes with this level of craftsmanship, flexible living space, and truly unforgettable views are rare. See Listing Details & 58 images.
$645,000 $303 per sq.ft. West Windsor VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 2515 | Acres: 10.27Listed on Thursday Jul 9, 2026
Description: Quietly sited off a private secluded road, sits a finely hand-crafted family home and outbuildings on 10.27 acres. The lot features an open yard, gardens, stone walls, woodland trails & nearby brooks. The main house features post and beam construction with sweeping cathedral ceilings, 2 bedrooms, 1.5 baths, a loft, finished lower level, and many custom-built features. The kitchen is well appointed with custom cabinetry and stone counters. A stand-out bonus feature comprises a detached 2 bedroom in-law or rental apartment above an 1150 sq. foot office/woodworking shop prefect for hobbies or a commercial home business. This property is perfectly sited in close proximity to State Forest for hiking, biking trails on Mt Ascutney, easy access to Interstate 91, Woodstock VT, Hanover NH, Dartmouth, and all recreation. See Listing Details & 35 images.
Under Contract
$775,000 $245 per sq.ft. West Windsor VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 3168 | Acres: 2.5Listed on Tuesday Jul 7, 2026
Description: Located in the heart of Sheddsville-West Windsor's earliest settlement, this lovingly stewarded historic Greek Revival Farmhouse imbues the true character of the Vermont vernacular. Improved over the centuries to accommodate modern living, all while preserving the the period detail and charm with original pine plank floors, 6/6 sash windows and hewn beams. The home was well built of solid and sound plank construction, providing insulation throughout. The beautiful Great Room addition is anchored by a handsome wood burning fireplace with custom cherry mantel, and connects to the exterior spaces through French doors stepping out to a covered porch and a spacious deck overlooking a sweeping level lawn, mature maple trees, established perennial beds, and a firepit at the edge of a four-season stream. Open concept eat in kitchen with farmer sink and butcher block counters, formal dining room, library- TV room, study with a half bathroom. Two mudrooms complete the main level. Moving upstairs, there's a generous primary bedroom ensuite with a wood stove, a laundry room, three additional bedrooms and a shared bathroom. Leased Tesla back up battery provides peace of mind in the event of a power outage. The ample three-bay barn can be used as parking, equipment storage, workshop, or for farm animals. Extensive dirt road, and trail systems (ideal for equine interests, hiking, cycling) are just out side your door. Easy access to all recreation, Interstate, Woodstock, Hanover NH. 2.25 Hours to Boston. 4.5 hours to NYC. Showings begin with an Open House on Saturday July 11 from 11:00 to 12:30 See Listing Details & 42 images. Includes a Virtual Tour
$824,900 $366 per sq.ft. West Windsor VT Home »
3 Beds | 3 Baths | Total Sq. Ft. 3392 | Acres: 3.03Listed on Wednesday Mar 18, 2026
Description: Experience the best of Vermont living in this custom-built home in desirable West Windsor, where thoughtful craftsmanship, energy efficiency, and four-season recreation come together. Designed and built by its original builder, this home offers exceptional quality, low-maintenance living, and comfortable year-round enjoyment. Whether you're searching for a primary residence, a Vermont vacation home, or the perfect mountain retreat, you'll appreciate the generous sleeping spaces that easily accommodate family and guests. After a day of skiing, snowmobiling, hiking, mountain biking, or exploring, gather around the cozy fireplace and soak in the peaceful mountain views that make this property feel like a true escape. Outdoor enthusiasts will love the location, with easy access to Ascutney Outdoors, Mount Ascutney State Park, and the renowned VAST snowmobile trail system. World-class skiing at Okemo Mountain Resort and the charming villages of Woodstock and Brownsville are just a short drive away, making this an ideal home base for every season. A spacious two-car garage provides ample storage for vehicles, outdoor gear, and recreational equipment. Set in one of Vermont's most sought-after communities, known for its scenic beauty, outdoor adventure, and welcoming small-town charm, this exceptional property offers the perfect balance of privacy, convenience, and lifestyle. If you've been dreaming of owning a Vermont mountain home where every season brings a new adventure, this is the one you've been waiting for. See Listing Details & 44 images. Includes a Virtual Tour
Under Contract
$930,000 $395 per sq.ft. Village of Brownsville in Town of West Windsor VT Home »
Waterfront on Pond _Unnamed4 Beds | 3 Baths | Total Sq. Ft. 2352 | Acres: 80
Listed on Wednesday Apr 15, 2026
Description: 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 charming raised ranch blends comfort and space, perfectly positioned to take in breathtaking views of Mount Ascutney. Surrounded by natural beauty and abundant wildlife, outdoor enthusiasts will appreciate the close proximity to the VAST Trail System and Mount Ascutney Ski Area, offering year-round recreation right at your doorstep. Ideally situated less than 15 minutes from the Green Mountain Horse Association, under 2 hours from Manchester-Boston Regional Airport, and just under 2.5 hours from Boston, Massachusetts. Whether envisioned as a private retreat, a legacy estate, or an investment with room to grow, this remarkable property seamlessly blends heritage, scenery, and endless possibility. See Listing Details & 59 images. Includes a Virtual Tour
