500 Route 169

Woodstock, CT 06281

Set high on historic Woodstock Hill, this distinctive 19th-century property offers a rare combination of history, character, exceptional views, flexible living spaces, guest accommodations, gardens, and opportunity. Offering approximately 2,500 square feet, this beautifully maintained home features five bedrooms and three-and-a-half baths, along with multiple living areas and a beautiful sitting porch overlooking the surrounding landscape. The home has been thoughtfully adapted to accommodate both private living and hospitality, creating flexibility for a variety of lifestyles. Two separate, thoughtfully furnished guest suites provide an established short-term rental opportunity and have enjoyed strong bookings. Guests have included parents visiting their children attending Woodstock Academy and Pomfret School, families attending weddings and local events, and visitors seeking to experience the beauty and charm of Woodstock. The grounds offer another exceptional dimension. Flower-growing areas, gardens, and a flower stand have been developed by the current owners during their first year on the property, building upon their longstanding experience with gardening and growing. The property offers an exciting opportunity to continue and expand the flower-growing vision, create a garden-based business, or explore the possibility of a future studio or shop, subject to applicable approvals. The elevated Woodstock Hill setting provides exceptional views and a peaceful sense of place, while the beautiful sitting porch offers a wonderful spot to enjoy morning coffee, afternoon gardens, or the changing seasons. Inside, historic character is complemented by comfortable living spaces and the flexibility today's buyers are seeking. The combination of a private residence, separate guest accommodations, gardens and open grounds creates possibilities rarely found in one Woodstock property. Whether you envision a beautiful primary residence, continuing the guest accommodations, expanding the flower-growing operation, or simply creating a special Woodstock retreat, this property offers the opportunity to make it your own. A truly special opportunity to own a piece of historic Woodstock Hill-where history, views, hospitality, gardens, and possibility come together.

Listing courtesy of June Cazeault of Hope Real Estate Group, Inc. Office Phone: (508) 943-4333 Broker Contact: (860) 377-2044



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Last checked: 2026-11-08 12:28 AM UTC.