Luxury homes for sale & real estate in Windsor County, VT

Luxury Home for sale in Windsor County, VT:

Welcome to Trail’s End - an oasis of peace and tranquility suffused with the restorative power of nature. Set amidst lush gardens and rolling lawns, this gorgeous timber frame house blends traditional looks with modern sensibilities and amenities, offering comfortable, light-filled, and highly functional spaces throughout. The beautifully appointed main floor primary bedroom features a spacious en-suite bathroom with a tiled shower and large soaking tub, plus a large walk-in closet and laundry. The rest of the main floor comprises a living room with soaring ceilings and a fireplace, dining area, office, chef's kitchen, screened-in porch, mudroom and half-bath. The second floor include

Luxury Home for sale in Windsor County, VT:

This spacious, bright, impeccably maintained hilltop retreat checks all the boxes, with stunning long-range views to both the southeast and northwest. Open concept kitchen with granite counters, maple cabinetry, pantry, excellent quality stainless steel appliances, and mudroom entry. Private deck and porch for outdoor entertaining. The living room is anchored by a brick wood-burning fireplace, and French doors opening to a generous dining room with an expansive view to the east. Oak plank floors run throughout the main level. Primary bedroom ensuite with huge walk-in closet, and a private deck. There are two additional bedrooms on the main level. Heading downstairs, there’s a spaciou

Luxury Home for sale in Windsor County, VT:

Settle into the farmers porch with a morning coffee and watch the seasons change across the Vermont hills. Inside, every detail speaks to quality craftsmanship — thoughtful appointments, warm finishes, and a layout designed for real family life. The yard has plenty of room for kids to run, explore, and make the kind of memories that bring families back to Vermont generation after generation. Built with efficiency in mind, this home is highly fuel efficient — keeping Vermont winters cozy without the utility sticker shock. A whole-home generator means you're covered when the nor'easters roll in, because up here, that's just smart living. The location is the cherry on top. You're j

Luxury Home for sale in Windsor County, VT:

Circa 1799 Vermont cape, thoughtfully restored and expanded to over 7,300 finished square feet on 12.5 private acres, minutes to Silver Lake and Woodstock village. Five bedrooms, nine baths, and a layout that balances everyday living with the ability to host. Original materials carry throughout, including wide pine floors, skim-coat plaster walls, hand-carved paneling, and period hardware, giving the house a consistent, grounded feel across old and new spaces. The 24' x 24' kitchen is designed for real use, anchored by an eight-foot Atlantic granite island and equipped with Sub-Zero, Wolf, and DCS appliances, dual Bosch dishwashers, and a walk-in pantry with tiled counters, extensive storag