217 south main street

One of Wolfeboro’s most distinctive buildings sits proudly on South Main Street, right in the heart of town. Under the same ownership for nearly a century, this 1870 octagonal landmark—one of only five in New Hampshire—is now ready for its next chapter: a bold and beautiful residential transformation. Ideally located between Brewster Academy and Huggins Hospital and just a short stroll to Lake Winnipesaukee and downtown shops, this corner-lot gem blends walkable convenience with architectural character that can’t be replicated. Currently zoned commercial, the property allows for a variety of residential uses with appropriate approvals—single-family, duplex, multi-family, ADU, B&B, in-home daycare, dormitory, or even a private museum. With both interior and exterior access to the second floor—including a separate entrance via exterior staircase—it’s easy to envision two distinct living spaces for multigenerational use or long-/short-term rental income. The first floor was renovated in 2019 with bright, open spaces, while the upper level retains its original charm and awaits your vision. Outside, enjoy mature trees, ample parking, and endless potential. 217 South Main isn’t just a home—it’s a legacy waiting to be lived in.