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5 on this page| № | Name | Category | Address | Record |
|---|---|---|---|---|
| 01 | Quest Haven Books & Comics An independent bookstore and comic shop on the west side of the square, also serving specialty sodas. | Bookstore | 104 N 1st AveWinterset, IAWinterset Courthouse Square Commercial Historic District | Listed · independent · address on record |
| 02 | Urban Taproom and Grill A casual taproom and grill with wood-fired pizza, burgers, and a rotating beer selection. | Bar | 1511 N John Wayne DrWinterset, IAWinterset Courthouse Square Commercial Historic District | Listed · independent · address on record |
| 03 | The Bakery Unlimited An award-winning scratch bakery known for its apple fritters, ranked among the top donut shops nationally. | Bakery | 119 N John Wayne DrWinterset, IAWinterset Courthouse Square Commercial Historic District | Listed · independent · address on record |
| 04 | Petite Cafe A small cafe just off the downtown square serving locally roasted coffee and grab-and-go baked goods. | Coffee Shop | 106 W Court AveWinterset, IAWinterset Courthouse Square Commercial Historic District | Listed · independent · address on record |
| 05 | Urban on the Square A casual restaurant on the downtown square offering seasonal menus, wine, and specialty cocktails. | Restaurant | 69 E Jefferson StWinterset, IAWinterset Courthouse Square Commercial Historic District | Listed · independent · address on record |