W Windsor Brownsville Area VT
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$599,000 | $250 per sq.ft.
84 Old Barn Lane
4 Beds | 3 Baths | Total Sq. Ft. 3200 | Acres: 3.2
This is a MUST SEE to appreciate! Breathtaking Views of Mt. Ascutney & the Valley Beyond! Welcome to this stunning custom-built 4-bedroom, 3-bath home where every window frames a masterpiece. Sweeping, panoramic views of majestic Mt. Ascutney and the rolling hillsides create an awe-inspiring backdrop you'll never tire of -- whether sipping morning coffee or watching the sunset paint the peaks gold on a 900 square foot deck. The thoughtfully designed layout offers the ease of first-floor primary suite living, complete with privacy and convenience. Upstairs, three additional bedrooms provide ample space for family, guests, or a dedicated home office. The finished walk-out basement adds exceptional versatility with a bonus bedroom and a spacious recreation room -- perfect for entertaining, a home gym, or separate entrance in-law suite. Step outside and enjoy the large, open yard -- ideal for outdoor entertaining, gardening, or simply soaking in the surrounding natural beauty with wildlife in abundance. Charming, well-built chicken coop adds both function and farmhouse character to your yard. Passive solar greenhouse roof system allows a heat sink to offset your fuel costs. A rare opportunity to own a truly custom home where quality craftsmanship meets one-of-a-kind scenery. Properties with views like this don't come along often -- don't miss your chance to make it yours! See
MLS Property & Listing Details & 58 images.
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$645,000 | $303 per sq.ft.
221 Dunkel Road
4 Beds | 3 Baths | Total Sq. Ft. 2515 | Acres: 10.27
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
MLS Property & Listing Details & 35 images.
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Under Contract
![WEST WINDSOR VT Home for sale $$775,000 | $245 per sq.ft.]()
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$775,000 | $245 per sq.ft.
1393 Sheddsville Road
4 Beds | 3 Baths | Total Sq. Ft. 3168 | Acres: 2.5
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
MLS Property & Listing Details & 42 images. Includes a Virtual Tour
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Under Contract
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$930,000 | $395 per sq.ft.
567 Churchill Road
4 Beds | 3 Baths | Total Sq. Ft. 2352 | Acres: 80
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
MLS Property & Listing Details & 59 images. Includes a Virtual Tour
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$1,325,000 | $519 per sq.ft.
325 Cemetery Road
4 Beds | 2 Baths | Total Sq. Ft. 2554 | Acres: 26.72
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
MLS Property & Listing Details & 46 images. Includes a Virtual Tour
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$1,345,000 | $265 per sq.ft.
310 Pierce Hill Road
7 Beds | 6 Baths | Total Sq. Ft. 5774 | Acres: 5.51
Set against sweeping views of Mount Ascutney, this distinctive property offers the kind of Vermont escape buyers rarely find--private, spacious, and designed for gathering. Thoughtfully expanded over time, the home seamlessly blends two living spaces, creating an ideal setting for hosting extended family and friends while still offering comfort and privacy for all. The newer portion of the home is centered around light and connection, with an open-concept living, dining, and kitchen area anchored by a custom stone fireplace and framed by floor-to-ceiling windows that capture the mountain views. Step out onto the sun-drenched deck--perfect for morning coffee, après-ski evenings, or summer entertaining. The primary suite offers a peaceful retreat with its own private deck, ensuite bath, walk-in closet, and dedicated office space. The original wing of the home provides additional room for guests, featuring four bedrooms, kitchen and its own living area, as well as direct access to a second deck overlooking the surrounding landscape--creating a natural separation that makes hosting effortless. Whether used as a single expansive home or configured to offer private guest accommodations, the layout supports a range of lifestyles--from weekend retreats to extended stays. Located in the heart of Brownsville, just moments from the trails and outdoor recreation of Mount Ascutney, this property offers four-season appeal. Enjoy easy access to the charm of nearby Woodstock, as well as skiing at Okemo and Killington, and the cultural and dining destinations of the Upper Valley. A rare opportunity to create a true Vermont getaway--designed for connection, relaxation, and year-round enjoyment. See
MLS Property & Listing Details & 32 images. Includes a Virtual Tour
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$3,250,000 | $1,012 per sq.ft.
Price Change! reduced by $100,000 down 3% on June 28th 2026
166 Jewett Road
5 Beds | 5 Baths | Total Sq. Ft. 3212 | Acres: 98
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
MLS Property & Listing Details & 60 images.
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