40 Simmons Drive, Woodstock

Originally built by the developer of Simmons Drive as his personal home, this spacious Woodstock property offers a rare combination of Village convenience, mountain views, and a peaceful park-like setting.

Situated on a quiet no-outlet street, it's just a five-minute stroll to Good Night restaurant, Tinker Street shopping, cafés, galleries, and everything the Village of Woodstock has to offer, all while enjoying a backyard shaded by mature trees and bordering Andy Lee Field, with no residential neighbors directly behind you.
The home offers three bedrooms, though it lives comfortably as four, with plenty of additional flexible space. An enclosed porch and wood-burning stove add warmth and character, while skylights bring natural light into the sunroom. Opening directly onto the deck, the sunroom offers an exciting opportunity to create a generous primary suite.
Downstairs, an additional flex room can serve as an office, exercise room, creative space, or extra storage. A two-car garage provides even more room for storage and projects, while the backyard offers space to gather around the fire pit beneath the trees.

Lovingly maintained and improved over the years, the home has seen numerous important updates, including bathrooms updated in 2019, a 200-amp electrical service, a furnace rebuilt in 2025, an approximately five-year-old oil tank, a main roof approximately nine years old, and fencing and decking improvements completed in 2019.

Big enough for all your friends, flexible enough for the way you actually want to live, and just minutes from the heart of Woodstock by any means of travel.

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