Set on a generous corner lot across from Motta Field, 26 Winslow Street offers space, light, and classic Provincetown character just three blocks from Town Hall. This 3-bedroom, 2-bath single-family home enjoys open views of the Pilgrim Monument and a central yet residential setting. Built in the 1920s as a Sears Catalogue home with Tudor Revival lines, the property has been thoughtfully updated and expanded while preserving its charm. The main level features a welcoming whitewashed foyer, a living room with a propane fireplace and reading nook, an office alcove, a formal dining room with built-in hutch, an updated galley kitchen, and a full bathroom. A main-floor bedroom includes two walk-in closets. Off the kitchen, a bright four-season sunroom opens to a redesigned, fenced backyard with western exposure, hot tub, outdoor shower, and multiple entertaining areas. Upstairs are two spacious bedrooms and a full bath. Additional highlights include a +/- 400 sf finished basement/entertainment room, A/C, hardwood floors, a detached garage suitable for parking, a gym, an artist studio, or an ADU, and on-site parking for 2-3 cars. This well-maintained home is Guest Favorite on Airbnb.