You are viewing Windsor Area VT Homes between $500000 and $1000000 dollars.
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
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.
$535,000 $108 per sq.ft. Windsor VT Home »
6 Beds | 4 Baths | Total Sq. Ft. 4933 | Acres: 0.48Listed on Wednesday May 13, 2026
Description: Come see and appreciate this recently rejuvenated and extraordinary home that includes 6 bedrooms and 4 bathrooms as well as a 2 car garage! Located just off the downtown village area, this unique property features historical charm and character with vintage woodwork, custom wood floors, high ceilings, spacious rooms and the nooks and crannies a classic home has to offer! Relax on the rear porch or enjoy the private yard and great family room that overlook the nearby pond providing a peaceful retreat at the end of a long day! See Listing Details & 36 images.
