137 South Street

Iconic Windham Landmark - Jimmy O'Connor's Pub Here's your chance to own a beloved piece of Windham history! Jimmy O'Connor's Pub has been a cherished local institution for nearly 50 years — a cozy, Irish-inspired pub that has welcomed generations of locals, second-home owners, and travelers alike. With its authentic atmosphere and warm hospitality, this family-owned gem has become a true staple in the community. Located in an A+ spot on South Street — directly across from the Windham Golf Course and Little League fields, and just quarter mile to Windham Mountain Club — this high-visibility property sits within the town's designated commercial corridor, offering endless possibilities for its next chapter. Recent updates include a new roof (just 2 years old) and a state-of-the-art Ansul hood system in the kitchen. The property is served by municipal sewer and has ample parking for 20+ cars. A spacious backyard with level terrain is perfect for outdoor dining, events, or even future expansion. Whether you're looking for a lifestyle change, envision a farm-to-tap bistro, or want to carry on the pub's legacy — this is a rare opportunity to reinvigorate a beloved business in the heart of Windham. A place with heart, history, and potential- view now! Adding to the potential, additional land available purchase. Ask agent for details.