Luxury Properties for sale in the Windsor County (VT)

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

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

Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this...

Presented by Carol Wood | Williamson Group 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

A rare in-village offering, 7 Slayton Terrace combines walkability, views, and beautifully renovated interiors—just steps from the heart of Woodstock. Sited on an oversized...

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

Perched above the Connecticut River Valley with sweeping views to the New Hampshire mountains, this meticulously maintained five bedroom, four and a half bath home offers a rare...

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

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

Over $244,000 price adjustment and $120,000 income, this one you should consider owning. fully furnished too. timbers in the sky Featured in Log and Timber Home Living magazine,...

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

Nestled on a 3-acre private lot at Hawk Resort in Vermonts Lakes Region, this expansive custom residence offers an exceptional mountain retreat. Thoughtfully designed across four...

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

The Richmond House Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a proud brick Federal distinguished by its softly weathered...

Presented by Derek Cosentino | Four Seasons 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