Luxury homes for sale in the Windsor County (VT)

Nestled in the tranquil hills of West Windsor, Vermont, Rock Haven Estate is a remarkable 33.49-acre country sanctuary offering three separate luxury residences, set along a...

Presented by Kate Jarvis | Williamson Group Sotheby's International Realty

Upper Farm — Circa 1799, large antique cape nestled on 12 acres with a stream, multiple ponds, and stunning waterfalls overlooking a large meadow. Beautiful, extensive gardens for...

Presented by Gretchjen Smith | Williamson Group Sotheby's International Realty

Iconic 1854 Gothic Revival home, known as the Lilac Cottage, is in the heart of South Woodstock Village, just a short stroll to The Ransom Tavern at Kedron Valley Inn, The South...

Presented by Daniel Kogut | Williamson Group Sotheby's International Realty

A rare opportunity to own a private, tranquil 6.7 ac farm that is just a short stroll to the Quechee Club and all amenities. Built in 1975 to the highest standard, and sited to...

Presented by Daniel Kogut | Williamson Group Sotheby's International Realty

Built over the course of two years and completed in 2023, this nearly new custom timberframe home showcases exceptional craftsmanship and fine attention to detail. Privately sited...

Presented by Teresa DiNapoli | Four Seasons Sotheby's International Realty

The ultimate family compound, award nominated video tour. This fully furnished and equipped luxury property is located in Andover, Vermont, set on 384 acres in the iconic Green...

Presented by Steve Stettler | Four Seasons Sotheby's International Realty

Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest...

Presented by Keri Cole | Williamson Group Sotheby's International Realty

This meticulously maintained five-bedroom, four-and-a-half-bath home offers sweeping views of the Connecticut River Valley and New Hampshire mountains. Thoughtfully designed for...

Presented by Karen DeMas | Four Seasons Sotheby's International Realty

Beautifully sited just a short walk from Woodstock Village, this 2015 custom-built home blends modern comfort with timeless Vermont charm. Thoughtfully designed for everyday...

Presented by Keri Cole | Williamson Group Sotheby's International Realty

Timbers in the sky Featured in Log and Timber Home Living magazine, this one-of-a-kind Vermont timber frame retreat, built in 2022, blends dramatic architecture with refined...

Presented by Freddie Ann Bohlig | Four Seasons Sotheby's International Realty

Serena Lodge was inspired by the legendary William Rockefeller estate in the Adirondacks, known as The Point, and thoughtfully designed to reflect its inviting look and warm,...

Presented by Debra Staniscia | Four Seasons Sotheby's International Realty

Once a tavern for travelers and a stagecoach stop in the early 1800s, 1607 Massey Road stands as a testament to Vermonts enduring spirit. This distinguished 1810 Federal style...

Presented by Patrick Kelley | Four Seasons Sotheby's International Realty

Located in historic Shedds Ville, in the heart of West Windsor, this bright, spacious contemporary home features generous bright rooms that flow seamlessly for entertaining and...

Presented by Daniel Kogut | Williamson Group Sotheby's International Realty

Discover the possibilities with this beautifully crafted three bedroom, three and one half bath home and versatile Post and Beam barn/studio, set between Woodstock and Silver Lake...

Presented by Eric Johnston | Four Seasons Sotheby's International Realty

Escape to this enchanting circa 1830 Colonial, a quintessential Vermont country retreat perfectly positioned at the edge of Weston Village with breathtaking Green Mountain views....

Presented by Lee Brown | Four Seasons Sotheby's International Realty