You are viewing West Windsor VT Homes between $0 and $30000000 dollars.
$3,250,000 $1,012 per sq.ft. West Windsor VT Home »
Price Change! Reduced by $100,000 down 3% on June 28th 2026
5 Beds | 5 Baths | Total Sq. Ft. 3212 | Acres: 98
Listed on Wednesday Apr 15, 2026
Description: 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, enrolled in Current Use. The main floor offers a new kitchen which boasts a beautiful 11' quartzite island & counters. Dining & Family Room with soapstone woodstove, Living Room with a new Rumford Fireplace with rod iron & glass doors for efficiency. A large Sunroom with slate floor, more than an entry it's a nice transitional space to enjoy, 3 BR/3 BA and a Sitting area on the 2nd floor with a tranquil view of the back fields. 2 additional BRs and a half bath on the 3rd floor. All new wiring, plumbing, new Bosch propane furnace supplies radiant heat, triple pane, Anderson low-E4 windows, sheetrock, DaVinci slate-like rubber roof & cherry floors. Fully insulated, extremely efficient. Custom built trim, wide baseboards, wainscoting & cabinets. 200+ year old pine boards from the house were used to craft bathroom vanities, 3rd floor stairs & beautiful doors. Outdoor amenities include in ground pool, gardens & lovely stone patio. A large-3600 sq ft former dairy barn with new wiring & FHA furnace & oil tank. Now used as a garage, workshop & abundant storage space offers ENDLESS possibilities! See Listing Details & 60 images.
$1,450,000 $1,066 per sq.ft. West Windsor VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1360 | Acres: 103.1Listed on Tuesday Jun 9, 2026
Description: They say land remembers. On Rush Meadow Road--where rolling fields meet the quiet rhythm of the seasons--there is a place that has been held, cared for, and passed down for over a century. This 103-acre estate is not something that was assembled. It was lived. Worked. Protected. For generations, it operated as a dairy farm, and the land still reflects that stewardship--lush hayfields, a ready-to-tap sugarbush, rich soil for gardening and beautiful solar exposure across every acre. It's the kind of property that continues to give, year after year. At its heart sits a classic Vermont farmhouse with 3 bedrooms and 1.5 baths, grounded by its traditional woodshed ell and surrounded by substantial garage and equipment space. It's practical, authentic, and full of quiet character--equally suited as a full-time residence or a welcoming guest house. To the west, the land opens into sweeping fields with one of the most compelling building sites in the region--long-range views stretching to Mt. Ascutney, expansive and uninterrupted. Whether you envision a private compound, a retreat, or preserving the land as it has been for generations, the setting invites something meaningful. Consider your dream home resting at the height of the land, the beginning to your own heritage. Moments from Brownsville, with easy access to trails across Ascutney Mountain, coffee at local favorites like the Butcher & Pantry, and the culture of Woodstock just 25 minutes down the road, this property offers both connection and complete escape. This is not simply a farm. It is a legacy--waiting for its next chapter See Listing Details & 44 images. Includes a Virtual Tour
$1,345,000 $265 per sq.ft. Village of Brownsville in Town of West Windsor VT Home »
7 Beds | 6 Baths | Total Sq. Ft. 5774 | Acres: 5.51Listed on Wednesday Jun 3, 2026
Description: With sweeping views of Mount Ascutney, this exceptional home offers the Vermont lifestyle so many buyers dream of. A place where family and friends gather, traditions begin, and every season brings new adventures. Thoughtfully expanded over time, it blends two living spaces into one inviting home, offering generous room to be together while providing comfort and privacy for everyone. The newer addition features an open concept kitchen, dining, and living area anchored by a custom stone fireplace and dramatic floor to ceiling windows framing the mountain views. A sun-filled deck invites morning coffee, summer entertaining, or cozy après ski evenings. The primary suite is a private retreat with its own deck, ensuite bath, walk in closet, and dedicated office. The original wing offers four additional bedrooms, a kitchen, living area, and its own deck, creating an ideal space for guests or extended family. Whether enjoyed as one expansive residence, configured for private guest accommodations, or explored for its income-producing rental potential, the flexible layout adapts to a variety of lifestyles. Located in the heart of Brownsville. Just minutes from Mount Ascutney's trails and outdoor recreation, and within easy reach of Woodstock, Okemo, Killington, and the Upper Valley, this is a rare opportunity to own a true Vermont retreat where unforgettable memories are made all year long, with the added flexibility of potential rental income when you're away. See Listing Details & 32 images. Includes a Virtual Tour
$1,325,000 $519 per sq.ft. West Windsor VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 2554 | Acres: 26.72Listed on Wednesday Apr 29, 2026
Description: 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 pine and maple floors run throughout, adding classic farmhouse character. The equestrian amenities are outstanding: a 3,024-square-foot stable with seven spacious stalls, a heated tack room, wash stall, bathroom, and laundry area. The 100' x 200' riding arena features a state-of-the-art, eco-friendly footing made from recycled sneakers, offering outstanding drainage, low dust, and excellent footing. Outdoor facilities also included are a round pen, four grass paddocks, and one dirt paddock. Quiet gravel roads invite walking and riding, with access to the Green Mountain Horse Association trail system. A stream winds along the property's West border, while apple and pear trees provide seasonal bounty. High-speed internet ensures fast connectivity. Ascutney Outdoors, with 40 miles of trails for horseback riding, mountain biking, skiing, and hiking, is nearby, and the popular Brownsville Butcher and Pantry is less than two miles away. (Horses not included) See Listing Details & 46 images. Includes a Virtual Tour
$1,325,000 $729 per sq.ft. West Windsor VT Home »
2 Beds | 2 Baths | Total Sq. Ft. 1817 | Acres: 5.4Listed on Friday Jun 5, 2026
Description: Constructed in 2025, and located in the desirable Rush Meadow region of West Windsor, this impeccably orchestrated Yankee Barn Post and Beam home features superb materials, old world craftsmanship and detailed fit and finish. Custom milled cabinetry and built-ins throughout. The rooms are filled with natural light with stunning bucolic views from every window. The home is centered by a dramatic floating staircase leading to the loft area. Red oak flooring runs throughout. The open concept kitchen is suited with top quality appliances, and a center island with a rich walnut edged yellow birch countertop. The first level Primary ensuite has a dressing room with laundry, and bathroom with a walk in shower and soaking tub. Up the stairs, there's a spacious area for TV Room, or office and a guest bedroom. The walk-out lower basement level is spacious with high ceilings- perfect opportunity for future expansion. The home connects seamlessly to exterior spaces with a stone terrace and a screened porch, both situated to highlight the lovely pastoral views to Mt Ascutney, and beyond. State of the art mechanicals with central AC. Convenient to trail network, all recreation, Woodstock, Hanover NH and Interstate. See Listing Details & 38 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
$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
$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
$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.
$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.
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.
Under Contract
$474,800 $321 per sq.ft. Village of Brownsville in Town of West Windsor VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1480 | Acres: 1.53Listed on Thursday Apr 16, 2026
Description: 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, extensive perennial gardens, pond, vegetable garden area & fruit trees. Outbuildings for various storage needs. Automatic/timed lighting on granite posts line the driveway. At Ascutney Outdoors; walk to hiking & mountain biking, skiing & tubing just outside your door! Selling due to job situation. Ascutney Mountain has protective covenants including rights of 1st refusal. See Listing Details & 24 images.
$339,000 $262 per sq.ft. West Windsor VT Home »
Price Change! Reduced by $10,000 down 3% on July 1st 2026
3 Beds | 2 Baths | Total Sq. Ft. 1292 | Acres: 10.49
Listed on Tuesday May 5, 2026
Description: Great Locatons! Manufactured Modular home on 10.47acres with 3 stall barn with hayloft, tack room, water & electricity; older fencing remains. Home has mudroom entry, utility room, & corrugated metal roof. It's been completely rewired, insulated, 3 Mitsubishi mini-splits, soapstone woodstove, GE kitchen appliances, flooring. There will be flooring & other building materials left onsite. Work remaining on interior- some flooring & taping, all trim & painting. Exterior needs siding. Estimates to finish upon request. Great area for outdoor recreation, close to GMHA & Ascutney Outdoors, 30 minutes to Okemo. 45 to Killington. See Listing Details & 28 images.
$265,000 West Windsor VT Home »
Price Change! Reduced by $14,900 down 6% on June 17th 2026
0 Beds | 0 Baths | Total Sq. Ft. 0 | Acres: 9.4
Listed on Thursday Mar 26, 2026
Description: 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 your horse, bike or sled 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 height of the land or sit by the babbling brook as you plan the completion of this project. The sellers have used all quality materials in the building, road upgrades and culverts to the property are done, state WW permit allows 3 BR septic system, costs available for installation of septic, electric or solar power. Electridc now installed to neighboring lot. See Listing Details & 19 images.
